The Learning Leader Show With Ryan Hawk
As Kobe Bryant once said, “There is power in understanding the journey of others to help create your own.” That’s why the Learning Leader Show exists—to understand the journeys of other leaders so that we can better understand our own. This show is full of learnings taught by world-class leaders—personal stories of successes, failures, and lessons learned along the way. Our guests come from diverse backgrounds—CEOs of multi-billion dollar companies, best-selling authors, Navy SEALs, and professional athletes. My role in this endeavor is to talk to the most thoughtful, accomplished, and intentional leaders in the world so that we can learn from them as we each create our own journeys.
info_outline
668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel
12/29/2025
668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel
Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Brian Kelly is the founder of The Points Guy, which he built from a side hustle blog into a travel media empire that he sold for $28 million. At 42, he's now an angel investor in 15+ companies, including Bilt (valued at $11 billion). In this conversation, he shares lessons on manifestation, selling too early, building yourself into the brand, and why vulnerability beats wins in interviews. Key Learnings (in Brian's words) In 1995, I was 12 years old, and I was great with computers, so I started booking all of my dad’s travel for work. He’d pay me $10 per booking. Then it turned into points, when my dad showed me all the American and US Air miles he had. “If you can figure out how to use all of them, we can go on a family trip.” And the rest is history. That was my first real, oh wait, this points thing is amazing. Points were a way for us to live a fabulous lifestyle. I grew up thinking we were poor, but I really wanted to live a fabulous life. My parents were very humble and did not spend money lavishly. For me I always wanted to travel. When I was a kid, I would spin the globe and be like, This is where I'm going. I would actually research Oman. Somehow genetically, I got this gene of I need to be rich and travel the world. I used to call Mercedes, get all of their glossy pamphlets for all their new cars, and I would cut them out and stick them on my wall. Manifesting alone won't make you wealthy, but visioning helps. I do believe being able to visualize what it looks like and taste it and get close to it helps you take the smaller steps to actually achieve it. When I think of my investments, I actually envision what they're gonna be. I envision that they're multi-billion-dollar companies. I believe it unlocks a level of pushing you to reach these mini steps that you can't see throughout the process. I started The Points Guy in 2010, but there were already Titan bloggers. I for sure felt imposter syndrome, but I saw that what they lacked was creativity. Points and miles are very clinical. Very few people were translating that for an audience. I knew I had an opportunity. I'm in my twenties, living in New York City. I'm gonna explain what everyday people need to know. Building a media brand became my moat. No one else in the points world was doing media. Doing media's frightening. While it was scary going on TV the first couple times (I almost fainted), I knew that each time I did it, I got better. That was the moat I would build. I would build The Points Guy into a brand more so than any of the others who had come before me. I saw from the beginning to double and triple down on that strategy of building something that's more than just a blog, but a lifestyle that people want to achieve. "I made a million bucks in my first six months of just blogging, but using affiliate links." In 2011, within six months of learning about affiliate marketing, I made six figures a month using the credit card links in my blog. I was still working at Morgan Stanley. My mom was like, this sounds too good to be true. You can't leave Morgan Stanley. I was making like $300,000 a month in affiliate. Meanwhile, at Morgan Stanley, my salary is $70,000 a year. But it didn't pay right away. My parents actually lent me $10,000 just to pay my rent. I remember where I was in Madrid when that first Chase deposit of $490,000 hit from months of back pay on the blog. I sold for $28 million because I thought the industry would collapse. When Bankrate offered me $28 million in May 2012, I kind of had this negative mindset over where the industry was going. About a hundred blogs started when people knew they could make money on affiliates. Most bloggers have zero business sense. They were writing stuff like, "Cancel your Amex, cancel your Chase, cancel, cancel. Then get new cards." I saw this really bad business sense, very shortsighted greediness. I'm watching this thinking they're gonna pull the rug. Do I regret selling? Yes, the company is way more than what I sold it for. But at the time, you always have to remember what the landscape was. We're coming out of the recession. There were still a lot of weak indicators. Building myself into the brand gave me leverage. I had a three and a half year earnout. Over that time, the business really started to grow, but then I realized, well, I am also the business. So, the more press I did, when I negotiated with that parent company to stay on, they paid me a lot of money and still a cut of the business to grow it as CEO. It's kind of crazy to think 13 years after selling, I'm still here. But because I built myself as a core part of the business as The Points Guy, I've been able to stay on with less risk, getting paid well to do what I love. I'm more of the brand visionary, the consumer person. I'm very much an ideas person. When we're speaking with our longtime clients or pitching new ones, that's really where my special sauce is used and not in the day-to-day. People are not mind readers. In 2020, I had this breakdown where I thought I would actually leave. I went to the owners, and I was like, I just can't do it anymore. They said, “Brian, we've been waiting for you to say that. You don't need to be CEO. We have plenty of smart people.” It was this aha moment. I think in life we often think polar, black or white. That's advice I give to people. Whether it's your parent company, your boss, your mentor, people are not mind readers. While there is risk to leveling with someone and saying, "Hey, this role is just killing me," more often than not in my career, the more vulnerable I was, the more it turned out to be such a blessing. Check Your Spam Email Frequently: In 2011, I was featured in the New York Times, but the email came to my spam email. At that time, the narrative that points were dead, blackout dates, etc. I was the only blogger putting a positive spin on points. And I tried to do it in an informative and fun way. I’m 6’7”, so putting my personal angle on my travel reviews had a huge impact on being the face of this industry. As a founder, I was a tough boss because it was so personal. If I look back at my time as CEO, I still took it very personally. I do take the integrity of this site. As we expand, we can't forego quality. In hindsight, I didn't highlight enough of the wins. I would focus too much on mistakes. That's advice I would give if I could do it all back over again, to just be much more positive reinforcement over negative. Founders need someone who can check them. You need to have someone around you, a leadership team, someone that can check you. I didn't have that for a very long time, and that's my fault. Making sure you have good people on your team that can be honest with you, and you create an environment of inviting that feedback and not freaking out when they give it to you, is important. I know I would be a much different CEO today if I did it again. Stop BSing in the interview process. Too many people take jobs not knowing what is going on whatsoever at the company. Far too many senior executives walk into positions and they're like, oh wait a minute. I like to be brutally honest in the interview process. Truth-telling is the beginning of having a great relationship because I want you to understand exactly what's in front of you. If you don't want to take it, that's so much better than hiring a senior exec and six months later, you just lost a year. Stop telling me the wins. In the interview process, stop telling me the wins because anyone can make their job look successful. "Oh, 200% ROI, this, that the other." In an interview, you're not gonna be able to fact-check any of this. We all know people can cherry-pick the data. It's really just diving deep into vulnerable moments about their leadership, the challenges as leaders they had with their teams. I'll tell them my challenges when I was CEO. I want people to be real and allow me to understand how they think, the type of leader they are. Charismatic people can trick you. The problem is that very charismatic people can trick you easily. I've been blinded by a great interview, especially when you're exhausted as a CEO and then someone's bantering with you. You're like, oh, that was fun. But I've hired plenty of people who are all talk. I don't want personality hires. I'm the personality. My engineering team, I really need people to ship updates. I still wake up in the middle of the night asking if my bills are paid. I still have imposter syndrome about “is this crazy what I've built?” It's for sure not about the car, but I will say investing in a home that's beautiful and makes you feel really good is important. For a long time, I was traveling a lot. I never put roots down, and I always felt like I was in transit. Now I have this beautiful farm with animals and horses in New Hope, Pennsylvania. It takes my blood pressure down immediately. Angel investing has basically become an addiction. In 2020, I opened up a space where I decided I wanted to have kids even though I was single, and also started investing and advising in relevant companies. The first one was Encore Jane, who was building Built, a credit card loyalty platform for renters. I'd always thought, how cool would it be to earn points on rent? I said, You're crazy, but if it does work, it'll be massive. Built is now at $11 billion valuation. I'll make more money now, probably on Built than I will at The Points Guy, which is wild to me. I have probably about 15 other companies I put my personal money in. I love it because I can help advise founders on everything I've done, and help open doors. Using that to build wealth has become an addiction. Relentlessness is what I see in leaders who sustain excellence. I am amazed at Encore's ability to push. If he's got 10 major things impacting his business, most CEOs will start with one or two, put the others on the back burner. He will relentlessly push for excellence. I don't wanna work for Encore, but to be in the room and strategize, every time I leave a meeting with him it keeps me fresh and active. Find mentors, not just companies. For recent college grads, find people, even at a company where you might not see your future. Find someone at that company that you connect with. If you're looking for a job, interview until you find that hiring manager that you feel is on an upward rise and that you can learn from. We often focus too much on the line of work or the company. Stop focusing on that and look at that manager or the CMO whose organization you would join. If they've done amazing things, get in right away and start networking. Put time on the CMO or CEO's calendar. Be bold. Every senior executive loves to see people come in with eagerness to learn. Show up and do extracurriculars at work. Go to the lunch and learn with the senior executive and actually get face time with them. Make sure they know your name. Those are the things that matter because when it comes time for compensation and reviews, the senior person may not work with you day-to-day, but they're like, oh yeah, that's the person I really like. They are a future leader. That's how you get ahead. Even if that boss leaves to another company, they might take you. Reflection Questions Brian says manifesting alone won't make you wealthy, but visioning what it looks like helps you take the smaller steps to achieve it. What specific vision do you have for your future that you could make more tangible (like his Mercedes pictures on the bedroom wall)? How might making it more concrete change your daily actions? He emphasizes that in interviews, he wants people to stop telling him the wins and instead dive deep into vulnerable moments about their leadership and challenges with their teams. If you were in an interview tomorrow, what's one vulnerable leadership moment you could share that would demonstrate how you think rather than just what you've accomplished? Brian realized he needed to tell his parent company, "I just can't do it anymore" as CEO, and they responded with relief, offering him a better role. What conversation are you avoiding right now because you assume the answer will be no, when the other person might actually be waiting for you to speak up? More Learning Hypergrowth Leadership Let Go of the Need of Approval Live Your Rich Life
/episode/index/show/learningleadershow/id/39509880
info_outline
667: Nick Gray - How to Host World-Class Events, Why Leaders Need a Personal Website, Writing Like You Talk, Mastering Introductions, the Viral Tokyo Trip, & Adding Value Before Taking It
12/22/2025
667: Nick Gray - How to Host World-Class Events, Why Leaders Need a Personal Website, Writing Like You Talk, Mastering Introductions, the Viral Tokyo Trip, & Adding Value Before Taking It
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Nick Gray is the author of The Two-Hour Cocktail Party and founder of Museum Hack. He's mastered the art of hosting events that strengthen networks and build genuine connections. In this conversation, he shares practical systems for hosting gatherings, why every leader needs a personal website, and lessons learned from his viral blind date trip to Tokyo. The Learning Leader Show Key Learnings Two Great Ice Breaker Questions: What’s a compliment that someone has given you that you’ve never forgotten about? If you could teach any class about a topic that you’re an expert on, what would it be? The power of a network is real: As a leader, you're probably hiring people regularly or looking for investors. By hosting simple, lightweight meetups or dinner parties, or happy hours once a quarter, you can strengthen your network, build it, and keep those loose connections or weak ties warm. Mix professional and personal contacts: For me, a really boring event would be all work people. Look for occupational diversity. If you're hosting a work event, invite some other random folks who you know are gonna be good conversationalists and add to the energy. Don't reach for the top shelf first. Most important advice for leaders: do not invite your most impressive contact to your very first happy hour or meetup. Your first party should be for your neighbors, the parents of kids at your school, those LinkedIn connections, high school buddies you haven't seen in a while. Your first party should be a comfortable meetup for 15 to 22 people that you host at your home with just cocktails, not a dinner party. Then slowly, once a quarter, you'll be adding more people to it and filtering your list. Collect RSVPs to ensure attendance. New hosts are absolutely terrified that nobody will arrive. As long as you get a minimum of 15 people to show up, your party will generally be a success. Use platforms like Partiful or Mixily (not Paperless Post or Evite) to get people to RSVP, let them know what to expect, and send reminder messages. Ten days before, send a reminder message hyping up the party. About a week before, send another reminder message with a little dossier of who the attendees are. Write something little: "Ryan Hawk hosts a podcast. He wrote a book. He lives in Ohio. Ask him about the ski trip he went on with his family." This serves to make anxious people or socially awkward feel like they're welcome and they have a conversational access point. Practical hosting tips on event day: Label your trash cans and your bathrooms. As people arrive, greet and welcome every single person, and make them a name tag. Write it out right in front of them, first name only. Do not pre-write your name tags. Force collisions through structured activities. Your job as a leader is to go through life collecting the interesting people that you meet and helping them meet each other. Can you become a connector? One way to be a connector is to host these meetups and force the collisions. Lead two or three rounds of introductions at your meetup. Make a little announcement 30 minutes after it starts: "There are so many interesting people here. I want you all to meet each other. We're gonna split into small groups. It might seem silly, but I promise the purpose tonight is for you to talk to as many new people as possible. We're gonna split into small groups of three or four people, and you're gonna go around and tell your life story in two minutes." End on time, especially for weekday events: Host from 6:30 to 8:30 PM with a hard stop on Tuesday or Wednesday nights. People appreciate having an end time because they have responsibilities. Having that end time makes them more likely to RSVP yes and actually attend. “I get more compliments on my party ending on time, and they leave with a positive experience, so they want to return for another.” Why every leader needs a personal website. If you have a blue check verified on Instagram, if you post at least once a month on LinkedIn, you probably need your own personal website. It's proactive reputation management. People are out there searching for you on Google and on ChatGPT. It may not happen every single day, but it probably happens every week. Whether it's parents of your kids at school, whether it's new employees, people are googling you. You want to have a personal website to put your best foot forward and make a good impression. Carrd.co to create a simple homepage or cloudflare to set up your domain name. Keep it simple: You don't need a Gary Vee type page. Your page can look like a Google Doc. Feed these large language models your story and bio. My website is plain text, simple homepage. I used to have a fancy design site. Now I'm like, dude, it doesn't matter. 80% of my visitors are on their cell phone and just want to read some text and have some links. The that changed everything. The viral Tokyo blind date trip taught me I was ready to share my life with someone. I ended up meeting my wife a couple of months after this experience because I realized I was ready. From a business perspective, one of the most interesting things while that was happening and for about a week afterwards: anyone would accept my phone call. My callbacks were instantaneous. My dial to answer fast. People were reaching out from everywhere. I was like, whoa, is this what it's like to be a celebrity? "I came back to Texas after the trip, ready to truly settle down and find a relationship and meet my now wife." Write like you talk: The best book about storytelling is . Don't try to write a LinkedIn post that says "I'm happy to announce." Would you actually say that to someone? No, you wouldn't. Say it like you talk. Advice on Blind Introductions: Use a double opt-in intro. Reach out to one person first, “Hey, are you taking new clients before I connect you with a friend?” Get both parties' permission, separately - then send the email. Give yourself a Free Day: Dan Sullivan suggests one free day a quarter from work. Make it a weekday, and even get a burner phone so you can’t check your work text/emails, so you’re completely disconnected from work. The keys to being a great host/MC: does such a great job talking about the theory of being a good leader. The host that doesn’t do a great job is the one who’s too cool to care. Give explicit instructions to people. You are a ring leader for an event, and you’re in charge of everyone’s energy levels and keeping the show on the road. Add value before taking value. Never send someone a message, "I'd love to pick your brain," or "I'm looking for a mentor." That is take, take, take. Think about how you can add value first. When you add value first to people, it's some sort of law of reciprocity. They're much more likely to want to help you out or do something in return. Advice for new grads in the AI era: AI and new tools are eating into the ability for companies to hire low-level employees that do grunt work. Learn how to use the tools themselves. Work with small businesses and entrepreneurs where you can make a difference. Develop a writing practice: Matthew Dicks has this activity called where every night you write down some note, some anecdote, something that stuck out for you. It gives you ideas about things to write about. Use AI as an editor, not a writer: Don't outsource your thinking to AI. Use the tools, understand how to use them, but don't outsource your thinking. It'll spit back something decent, but you don't want to outsource your thinking, especially as a leader. Reflection Questions Nick says your first party should be for neighbors, school parents, and LinkedIn connections you haven't seen in a while (not your most impressive contacts). Who are 15-20 people in your life that fall into this "comfortable but haven't connected recently" category that you could invite to a simple cocktail party? He emphasizes "add value before you take value" and never says "I'd love to pick your brain." Think about someone you want to connect with. What's one specific way you could add value to them first before asking for anything in return? Nick hosts events once a quarter to keep weak ties warm instead of trying to have individual coffee meetings with everyone. What's one relationship-building activity you're currently doing inefficiently that could be replaced with a group gathering? Additional Learning The Art of Gathering Unreasonable Hospitality Change Your Life Through The Power Of Storytelling Audio Timestamps 02:06 Icebreakers and Personal Stories 02:55 The Art of Hosting Events 08:27 Practical Tips for Successful Gatherings 20:16 Mastermind Events and Personal Websites 25:36 The Importance of a Personal Website 26:47 Crafting an Engaging Bio 29:27 The Viral Tokyo Trip 37:04 Living an Interesting Life 41:57 The Art of Hosting and MC’ing 44:50 Advice for New Graduates 46:35 The Power of Writing and Storytelling 49:07 EOPC
/episode/index/show/learningleadershow/id/39434290
info_outline
666: Angie Hicks (Founder of Angie's List) - The Power of Selling Door-to-Door, Executive Presence, Being Told She Was 'Too Nice,' and Her 2-Question Career Filter That Kept Her at One Company for 30 Years
12/15/2025
666: Angie Hicks (Founder of Angie's List) - The Power of Selling Door-to-Door, Executive Presence, Being Told She Was 'Too Nice,' and Her 2-Question Career Filter That Kept Her at One Company for 30 Years
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Angie Hicks, co-founder of Angie’s List (now called Angi). She started the company at just 23, going door-to-door as a self-described introvert and non-salesperson, and turned it into a national platform trusted by millions. During our conversation, we discuss what it takes to lead with authenticity and build lasting impact. Key Learnings Lead by listening and showing up. Whether it’s knocking on doors as a 23-year-old or meeting employees during office hours as CEO, Angie reminds us that being present, paying attention, and seeking feedback is the heart of leadership. Focus on people and learning. Angie’s career filter is simple: Do I like the people I’m working with? Am I learning new things? If yes, keep going. If not, it’s time to reconsider. Excellence isn’t just about results. It’s about the environment and growth around you. Take your work seriously, but not yourself. Confidence, humility, and authenticity go hand in hand. Angie shows us that you can be ambitious and driven without losing sight of the human side of leadership. From Angie... My co-founder, Bill Osterle, came to me when I was a senior in college and said, "Hey, I've got a crazy idea. Your parents are gonna hate it. But why don't we start a business?" I talked to my parents, talked to my friends, and then I ended up talking to my grandfather who was incredibly conservative. He grew up in the Depression, very fiscally responsible. "What do you have to lose? You're 22, your parents aren't going to let you starve, and you're not trying to support a family, so why don't you try it?" I was so taken aback by his response that that comment was probably what pushed me over the edge. I think young people can do this a lot, as we tend to overthink decisions. Sometimes people see things in you that you don't see in yourself, and you've gotta have a little faith. What better time to have a little faith than when you're young and carefree? Work hard, and things will come your way. We started in 1995. It was an offline world. We started as a call-in service and a monthly newsletter. The first name of the company was Columbus Neighbors. We left it like that for a year, and people just didn't get it. They thought the newsletter was the list. We decided to do a rebranding nine months in. We had two options: The List or Jackie's List (Jackie was the mother of one of our investors who knew everybody). At the last minute, Bill said maybe it should be Angie's List. “She does answer the phone.” Going door to door was hard. There was a lot of crying, I will be honest. I was selling something that wasn't concrete. “Hey, so when you need a plumber, you're gonna call me and I'm gonna help you find a plumber. And then when you hire someone, you're gonna tell me about it.” I viewed it as a numbers game. I need to knock on so many doors every day, and that's just what I'm going to do. Hopefully, if I stay on my pitch and I knock on enough doors, I will sell the right number of memberships. If I was selling one or two memberships a day, that's great. No business was gonna be built on me selling one or two memberships a day, but that's where we were. Sometimes you have to do the hard stuff. Sometimes you have to do the stuff you're not good at, and you have to figure out ways to work around it. Because no matter what you do in your career, there's gonna be stuff you don't love. I broke it down by like, I'm gonna do it for these two hours. I'm a believer in the you can do anything for a year philosophy. I could do anything for an hour a day. So you have to kind of disconnect and treat it that way, as this is like taking my medicine. But you do win every once in a while. And it is fun when you win. It is fun when you sell something. The day Patty gave me her church directory was the best day ever. You gotta celebrate the little wins as well in life. Starting a business is a long journey. It is more of a marathon than a sprint. There's usually not this burst of momentum where everything rolls your way. It's building blocks along the way. If you don't celebrate those little wins and you only focus on, oh, I'm not gonna be happy until we're at 10,000 members, that could be years. You need things to keep you going every day. Patty lived near Bill, so she kinda liked him too, but I think there was a little bit of entrepreneur in Patty. Patty needed nothing from us. She had lived in Columbus her entire life. She had renovated a 1920s house. All she was able to do was give. She knew everybody. But I think she just loved the spirit. You don't know whether that's door seven, door one, door 57, you don't know. But there is typically a breakthrough. Staying true and persistent, you know, there probably weren't a lot of women starting businesses going door to door in 1995, and Patty was like, look, she's got some gumption. She's tackling a business that in many ways is a man's world. Construction is a man's world. Whether that's starting a business or finding the right boss, or finding the right position, that same lesson is the same. I talk to young people, I say, Hey, you can do marketing anywhere. There's any company you can do marketing. When it comes to me... Go where you're gonna be with somebody who believes in you. That's gonna invest in you, because that's actually what's gonna change your trajectory. It's not the name on the company that's gonna change your trajectory. It's actually who's got your back, who's coaching you, that's going to make the biggest difference. The next inflection point for me was when we opened in Cleveland the year after that. It was the first market we had opened from scratch. I remember I went one morning and picked up the newspaper, picked up the Plain Dealer at the bagel shop across the street from my office. And there it was, our little two-by-three ad that said, "Tired of lousy service" with some clip art. I was so excited. I was like, This is amazing. We're in Cleveland. This is gonna be so great. And then I remember telling Bill, "We're gonna get so many calls." And he's like, "We're gonna get so many calls." And I don't think we got any calls that day. The transition from individual contributor to leading others was a horrible transition. It's actually really hard. I tell people that all the time because if you think about who do we promote in companies, we promote really strong individual performers. The skills that make us really good individual performers do not necessarily make us good leaders, managers, et cetera, because it's actually a whole different skillset. I was that overachiever kind of controller, let me just do it type person. You have to actually train yourself to not do those things because no one's ever going to be successful and learn if you're just over there stepping in. The early days when I was young and trying to manage people, not good. Not good at all. I ended up leaving for a year and a half to go to business school. I was pretty burnt out on the business, and I probably would've left the business had I not gone. It gave me a chance to reflect on where I've been and step back. Now I understand, I'm not in the pressure cooker. I can see where I've mistepped. I left when I was 25, three years in. The business had gotten big enoug,h and we decided to bring in a CEO because the 22- 23-year-old was kinda like, maybe we need some leadership here. My co-founder joined full-time at that point and came in as CEO. I joke around, I'm like, take a break. I was still keeping the books. The TV commercial was a hundred thousand dollars, which I had to convince our board on. I was like, look, either we try this or we just close Cleveland because there is no scenario here that we're gonna build a business with door-to-door sales at the rate we're moving. We basically took everything on Cleveland, which was $100,000. I would've been devastated had it failed. People started calling. I was so excited. Then all of a sudden it just kinda went bananas. You realize there's a lot of people with this problem. Doors slammed in my face at that point, not as much of an issue. And then we ended up being in Boston and Washington, and a bunch of other cities. Every time we'd go to a city, I'd fly in, and I would open the paper, and I would get all happy. The TV commercials themselves were funny because I can't do anything for fun anymore without seeing myself in the commercial. I did the first one, and they're like, listen, we're just gonna, we're not gonna tell anybody. It's just gonna go on, you know, we're just gonna do it really quietly. I was like, great. Okay, fine. And then it kind of took off. I had young kids at the time. I wouldn't let us advertise on kids' shows. There was never us on Disney Channel or Nickelodeon because I didn't want that. But the kids would see me on TV. You know, they would see me doing interviews. It happened for them at such a young age that they just kind of thought that's what parents did. I remember one of my kids coming home in middle school and being like, I can't believe you didn't tell me you were famous because it was finally, the friends had grown up enough that they were like, you know who her mom is, right? I became a little more closed off in my personal life as I became more public. Kids deserve to grow up in a world where they get to be kids and not have to deal with that stuff. In our little town, people were like, Oh yeah, she just lives here. And it became not a thing. It became more relevant to me when I was traveling. I started doing office hours. I did it on Fridays leading into the lunchtime, which, let's be honest, was probably one of the squishiest times of productive work. I was with a group of CEOs the other day, and I actually suggested, just try a little. It doesn't have to be a big thing. Just try a little and see where it takes you. The meetings were anything. It was career advice. What should I do? They might have ideas for the business. Hey, we should go into this line. I remember talking one day to our head of legal, and I was like, you know, I don't get open-door media requests anymore. And she kind of chuckled, and she said, That's because you have them all the time. You allow problems to come to you before they're big problems, so they become less of a thing. I'd rather people bring their concerns internally first and listen to 'em and address 'em when you can. They always come internally first, whether it's from an employee, whether it's from a customer. It's just how we handle those things as to whether they blow up into something bigger. I always tried to give them something in return. They come to talk to me and I'd introduce 'em to someone who would help. I'd open a door for them. To this day, I still love talking to customers. I think we live in a very digital age, and I feel like we don't talk to one another very much. People like people. They need to feel heard and have things resolved. I took that office hours idea, and now I do it with customers, so any pro can sign up and talk to me. Gives me a chance to understand, get a pulse on what's going on. The people on the front line are the ones who are making your brand. The marketing team might make some great social posts and some great TV ads. But many times, the people who are manning the phones or your chats are the ones that are leaving a more lasting impression on your brand than anything else. How do you bring the voice of the customer into the organization? Not everybody in our company is a homeowner. How do you make sure they can understand the customer? What's life like as a small business owner, as a pro? What's it like for a homeowner when something goes awry on their worst day? How do I bring those stories to life? I had to convince myself that it was a good use of time. Busy people who have lots of responsibility are active doers, overachievers, to sit back and talk and listen feels like, Okay, am I moving the needle? It feels a bit too squishy. That's why I would treat it just like some of the other things. I will give it an hour a week. Let's see what happens there. I could see the payoff. I can't go spend 30% of my time doing this, but there is a portion of time that I do dedicate. Feedback is a gift and something you should seek out. But yeah, it doesn't always feel great. One of the hardest pieces of advice I got came at a time when we were actually trying to do a transaction. They said, "You have an executive presence issue." And I was like, what? They said, "You're too nice to everybody. It doesn't help the company." I can't tell you how much that comment just killed me. But then I went out and got an executive coach, and I reflected on it. In many ways, it made me a better CEO. I learned that I could be me and I could still be nice and I could be kind, but there are moments I have to be clear. When I'm looking to promote someone or hire someone, knowing your stuff is super important. You don't want this person, who says, I'm the one who always knows the answer. You want someone who can learn from their team. I spent most of my career running marketing, and marketing moves fast. Some of the youngest members of the team are teaching me more things over the years than even some of the more seasoned marketing people. How are you constantly having a view about learning and staying smart in the trade? The ability to just be a good partner or work with people is important. Your job's not to come in and knock down walls. It's actually to build relationships because you can't do everything yourself. How are you at building cross-department relationships? My advice to recent grads: One of my favorites, take your work very seriously. Be good at what you do. Don't always be looking for that next thing that you gotta go tackle. Do what's in front of you first. Don't take yourself too seriously. You come out, you're like, Oh, I have all of these credentials. I should therefore be able to do these things. Sometimes the envelopes need stuffed and we might all do that together. So don't take yourself too seriously. We're gonna do this together. Be open to feedback and to helping others. Don't be afraid when people suggest things that seem totally counter. I think sometimes we get too rigid in our plans. I use Angie's List as an example. I was supposed to be a consultant. I was supposed to go be a business consultant, but then Bill comes in and says, hey, what about this? I could have easily been a business consultant and had a nice life. But I chose that door. A lot of times, people get a little too narrow in their focus and miss opportunities. So stay open to that. For me, it's all about the people you work with. Working with people that you're learning from, that believe in you, that's all that matters. I overindex there. People ask me, how are you still doing this after 30 years? I ask myself two questions, and if I can answer yes to those two questions, I'm in. If I answer no, I'm out. The two things are: Do I like the people I'm working with, and am I learning new things? When you're as long in your career as I am, you have to dedicate time and effort to learning new things so that you don't become that person that is like, we do this because we've always done it this way. Which I think is just like the worst line ever. Reflection Questions Angie's grandfather asked, "What do you have to lose?" when she was 22 and hesitating about starting a business. What decision are you currently overthinking that you might need to just take a leap on while you're young (or young enough) and the risk is manageable? S She says the skills that make us really good individual performers don't necessarily make us good leaders. If you've recently been promoted or are leading others, what specific "doer" habits do you need to let go of so your team can learn and succeed? Angie stayed at Angi for 30 years by asking herself two questions: "Do I like the people I'm working with?" and "Am I learning new things?" How would you honestly answer those two questions about your current role? If the answer to either is no, what does that tell you?
/episode/index/show/learningleadershow/id/39336815
info_outline
665: Pat Lencioni - Five Dysfunctions of a Team, Fear-Based Success, Working Genius, Anticipating Objections, and The Hidden Cost of Proving Yourself
12/08/2025
665: Pat Lencioni - Five Dysfunctions of a Team, Fear-Based Success, Working Genius, Anticipating Objections, and The Hidden Cost of Proving Yourself
Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Patrick Lencioni is the founder of The Table Group and a bestselling author of 14 books, including The Five Dysfunctions of a Team and The 6 Types of Working Genius. Behind his achievements (valedictorian, straight A's, business success) were childhood wounds that drove him to prove himself. Key Learnings "I think I'm really good at anticipating people's objections." I think about what they might be thinking and what I need to put out there. Whether talking interpersonally, giving a speech, writing a book, or on a podcast, I like to think about what the other person might be objecting to. Lean into empathy. I always felt like I needed to prove myself in order to be successful and to feel safe. That's not healthy. "When people tell you they got straight A's and were the valedictorian, the student body president, and got accepted to all the schools they wanted to get into, there's a wound there." Based on my personality type, I shouldn't have done all those things, but it was out of the need to prove myself. Which wasn’t healthy for me. My parents had a hard time being affirming because of their own lives. It wasn't until I was 55 years old that a friend who's a psychologist said, "You, my friend, have childhood wounds you've never dealt with." I got good Christian counseling and realized that the way I grew up, I wasn't supposed to grow up that way. It’s common in athletes & CEOs to feel like they haven’t done enough. They need to do more. "You're a noun, not a verb. You are enough, and you're not defined by what you do." Great achievements come out of fear, but "true greatness is best when it's only in the things that you're meant to be great at, and that you're doing it out of freedom and passion and love, not out of fear of failure." I remember seeing Tiger Woods on the Tonight Show when he was four years old. He was being groomed to be a golfer when he was four. It's best in life when we discover who God means us to be, then we do the things we're supposed to do and we're okay with not being good at the things we're not supposed to. Are we too affirming now as parents? People who are pretty darn good at everything it's usually because they're doing something out of fear. When I was a kid, my parents came from World War II and the Depression. It was like, hey, you got a roof over your head. There was a lot of suffering, and they weren't really attuned to that. Now we are hyper worried of our own kids suffering. No, suffering is actually good. They need to know they're loved and safe, but they're not gonna be protected from what is necessary for their development. The mistake I made was, oh no, I don't want them to feel like I did. Thankfully at my age, I'm now interacting with my mostly adult children and explaining to them what I did wrong. The Teammate Trifecta - How should we use it?: When I wrote The Five Dysfunctions of a Team right after 9/11, I thought, “That's the book on teamwork.” Then we realized you need The Ideal Team Player (humble, hungry, and smart) to hire people that fit on teams. Years later, we came up with Working Genius: Are they in the right seat? 3 steps to building a team: Don't let people on the bus if they're not humble, hungry, and smart. Make sure you have them in the right chair based on their gifts. Then teach them the Five Dysfunctions. Pat’s Two Working Geniuses: Invention and Discernment "Invention means I love to come up with ideas out of nothing. Discernment means I love evaluating things, curating things. God wired me to do that kind of thing.” When people say, "Pat, we have five minutes, and we need a new idea," I just take a deep breath and smile. One man's trash is another man's treasure. Every new idea I've come up with has been in the field, working with people. I asked Jim Collins, "Jim, you do all this research with data. I go into a room with leaders and just think, What's going on here?" He said, "Pat, that's just as valid as what I do. That's called field research and face validity." What is Pat terrible at? Finishing things. People say, “Well you finished 14 books.” And that’s because I had the help of others to make me finish those. I got a 4.0 in high school. That wasn't my personality. I went to every class in college, never blew off classes. My personality is the kind that should blow off classes that don't matter. But I was so afraid of failing and disappointing my parents and teachers that I did anything they asked. That was not natural; that was fear-based. Can we use fear as useful fuel? "You can use it in the short term, but if you're doing it in your life, no." "We should celebrate what other people are better than we are at things. We should literally celebrate what we suck at." If we have two kids and one's creative and the other's disciplined, we tell the creative one to be more disciplined and the disciplined one to be more creative. No. We have to say, understanding that you're not creative is good for you. That's not who you're meant to be. The hardest thing about being a parent is constantly asking yourself, “Am I pushing them too hard or not enough?” The hardest question you ask yourself as a parent is, “Am I pushing my kids too hard or not hard enough?” This question also applies to yourself. In Working Genius, should I work on my working frustrations? The short answer is no. Working Genius is all about knowing what you love to do. Enablement and Tenacity are my working frustrations, and so many of those things fall into parenting. I'd say to my wife, "Hey, Laura, let's outsource some of these things." Out of fear and guilt, she said no because she felt like she'd be a bad mother. Outsource the work you don't enjoy, and when you have to do it, try your best and don't feel guilty with the result. The electrical company turned off our power for not paying the bill. We need to accept our deficiencies and need to be able to laugh at the things we're not good at. Ryan’s Learning Leader Team: When your whole team has Tenacity as their working genius, your team loves to finish things. You will never be flaky. You might stick to something that needs to be changed way before it needs to be. In my company, we're always up for a change in plans, but not great at following through. If your team doesn't have Wonder and Invention, force yourself to borrow from others outside the organization to get new ideas. The Five Dysfunctions of a Team Vulnerability-based trust changes everything in teams. Eric Spoelstra uses Five Dysfunctions with the Miami Heat. He started when they acquired LeBron James. He said, "I don't know what offense we're gonna run this year, but I know we're gonna use the Five Dysfunctions." I love it in basketball, especially because you see them on the court. When people can be so vulnerable that they can say it was my fault, or I need help, or I'm sorry I was kind of a jerk yesterday at practice, it changes everything. But when you have a player who doesn't admit when they made a mistake or who blames everybody else, the ceiling of that team being great is so low. Humble, Hungry, Smart has been a great tool for athletic teams. I define it: no ego, it's about the team (humble). Hungry means I go above and beyond. Smart means I have emotional intelligence. I have the team members say, "Which of those three is your lowest?" It is crazy how people will call out. The goalie said, "I'm not smart. I yell at guys on the field, and I demean them. I gotta get better." Another kid said, "I need to be hungrier. I don't do the workouts at home." Pat phrases it this way when meeting with athletic teams. "Okay, everybody, look around at your teammates and think about the thing they want to get better at. If you want to be a good teammate, when you see your teammate doing the thing he just admitted he wants to get better at, you need to call him out on it." Once people start to have that language, it's amazing how they're coaching each other. And if as a coach yourself, I think you should tell people, "When I was a player, this was mine." They're gonna go, hey, if the coach admits that, I'll do it too. For leaders with Enablement & Tenacity as top geniuses, how do they avoid burnout? You have to be willing to start with "I am prone to burnout if you guys aren't aware of what's going on." The people with enablement and tenacity will say, "I'll just do it," and then they do. We had 12 employees and only one had Tenacity. We said we are going to kill her because every time we have to get something done, we're gonna say, "Jackie will finish." When people have enablement and tenacity, they and everybody else need to say, let's not abuse them. How do we assess a company in a short amount of time without focusing on their financials? When I go into a company, I find out what their meetings are like. If there's no disagreement and they're not exhausted at the end of a meeting, that's a red flag. If good people are leaving an organization, that's a massive red flag. I like going around and checking interactions. Is there an intensity with people together? Or are they alone and quiet? Also, keep an eye on customer reviews. What are the customers saying? There are two extremes of humility problems: arrogance on one end, and lack of confidence on the other. I first identified humility as a problem when I saw a CEO who didn't care about his company's results, but if he went on TV and answered questions about why they didn't meet their numbers, he would make jokes and make others laugh. If he was happy from that versus getting the results they needed, that's an issue. What specific traits do leaders need to have to get hired? A leader has to simultaneously believe they are no more important than the people they lead. They also have to accept the fact that their behaviors and words ARE more important than others in the company. "The one thing the leader has to do is break the tie." This past Friday, I was in a meeting trying to deal with a strategic issue between two great people. I dropped a curse word and said, "Listen, I'm pulling the CEO card right now. I don't do it all that often, but since I am the CEO, this is where we're going." Because I don't pull it every time, people are glad to have a CEO that will do that. If you're doing it every time, you lose credibility. Advice for young professionals: I wrote a book called The Motive, and what I say to leaders when they're young is: make sure your motive for being a leader is about sacrificing and suffering for others. "I want to help this organization, or I want to be the kind of person that takes on more than others for their good." Leadership is a lonely and selfless thing. It's wonderful, but the personal economics of leadership are not good. If you don't sign up for that, don't be a leader. Too many people say, I want to be a leader. And if you really scratch below the surface, they'll say, I think it would make me feel important, I'd get attention, maybe I'd make money, I'd have power. When that's your motive for being a leader, you're not gonna be a great leader. Reflection Questions Pat says people who were perfect students (straight A's, valedictorian, student body president) often have childhood wounds driving them. What in your past might be driving your current achievements? Are you operating from freedom and passion, or from fear and the need to prove yourself? He teaches his kids' sports teams to identify which of Humble, Hungry, or Smart is their lowest, then hold each other accountable when they see teammates struggling with that area. What would you identify as your lowest, and who in your life could you invite to call you out when you're not living up to it? Pat says the motive for leadership should be "sacrificing and suffering for others," not feeling important or controlling what you work on. If you're honest about why you want to lead (or why you currently lead), what's really driving you? Would people who report to you say you're other-motivated or personally motivated?
/episode/index/show/learningleadershow/id/39257840
info_outline
664: David Adelman - 664: David Adelman - Campus Apartments CEO and 76ers Co-Owner on Losing a Big Bet, Bar Mitzvah Real Estate Deals, His Grandfather's Holocaust Survival Story, and Building Philadelphia's New Arena
12/01/2025
664: David Adelman - 664: David Adelman - Campus Apartments CEO and 76ers Co-Owner on Losing a Big Bet, Bar Mitzvah Real Estate Deals, His Grandfather's Holocaust Survival Story, and Building Philadelphia's New Arena
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: David Adelman is the CEO of Campus Apartments, founder of Darco Capital, and co-owner of the Philadelphia 76ers. During our conversation, we discussed how losing a basketball bet at age 11 changed his life, investing his bar mitzvah money in real estate, becoming CEO at 25, his grandfather's Holocaust survival story, and why it gives him perspective on struggle, embracing failure, the trade-offs of building something excellent, and what he looks for when hiring leaders. Key Learnings "Why not me? Why not now?" David's mantra cuts through all the overthinking and excuses we make. When he saw other people building national real estate portfolios, he didn't wonder if it was possible—he asked why he couldn't do it. Stop waiting for permission. Stop waiting for the perfect moment. Ask yourself: why not me? Why not now? Make mistakes, just not the same one twice. David doesn't expect perfection from himself or his team. He expects learning. Fail fast, fail forward, but don't repeat the same failure. That's not growth—that's negligence. Embrace the suck, but evolve through it. David's grandfather survived the Holocaust after his wife and children were murdered. He escaped, joined the resistance, and rebuilt his life from nothing. When David thinks about that, he says: "No matter what, I don't know struggle." That's perspective. Most of what we call struggle is just discomfort. Understanding that doesn't make your challenges disappear... It makes them manageable. If your grandfather could survive the unthinkable, you can handle the hard day in front of you. At age 11, David challenged family friend Alan Horwitz to a basketball game and made a wager. Horwitz didn't let the kid win, and David lost his basketball, football, and baseball glove. To get them back, he had to go to Campus Apartments every Saturday to sweep sawdust and stack lumber. This losing bet became his entry into a billion-dollar career. At 13, David gambled his $2,000 bar mitzvah money by investing it with Horwitz in a building at 45th and Pine Streets in Philadelphia - a property his company still owns today. By age 17, he bought his first solely owned investment property. David was accepted into Temple University Beasley School of Law but chose to become a Property Manager at Campus Apartments instead. At age 25 in 1997, he became CEO of Campus Apartments. His grandfather, Sam Wasserman, was captured by the Nazis in 1942 and taken to the Sobibor concentration camp, where his wife and two children were immediately executed. Wasserman escaped during an organized revolt, joined the resistance, was wounded in battle, and was cared for by a woman named Sophie, who became his second wife. David said, "I feel a deep connection to him and what he went through. It's more like a sense of duty to honor him." David says, "I bet on jockeys, not horses. I ask, 'If the thing fails, would we support them again?' To be clear, a lot of our [investments] are going to fail.' He learned the hard way: "Friends would say, 'Here's a deal, put in X amount,' so you know, it's $250,000 or $500,000 or $1 million. I realized very quickly that it's probably a money-losing prospect to just invest in a friend of a friend's idea or because someone at your country club is investing in it." "It's called working off your debt." I literally lost everything to my “Uncle” Alan in 30 minutes when I was 11. My baseball glove, football, basketball, even my bank book. Every Saturday, I had to stack lumber and sweep sawdust to get one item back. Two years later, at my Bar Mitzvah, my parents asked if I wanted to give my gift money to my grandfather, who was good at picking stocks. I said no, I want to give it to Uncle Alan and buy real estate. At 13, I drove around with him, picked the biggest building he owned, handed him $2,000, and became a partner. My grandfather was in Poland with a wife and two kids when the Nazis rounded him up. There were two lines. One for men, one for women, and children. He never saw his wife and kids again. He escaped from the Sobibor prison camp, became a freedom fighter, got shot, and was in a hospital recovering when a woman checking on her brother saw this lonely soldier and went over to check on him. That was my grandmother. My mother was born in a displaced persons camp after the war. "No matter what, when I'm getting the crap kicked out of me in business or anything else, I don't know struggle." I think about my grandfather and what he went through. "That guy knew pressure and made it through the other side. So I have to stop being a little bitch about it and lean in." Uncle Alan always said, "Whatever you do in life, it shouldn't feel like work." I have never said I'm going to work. I say I'm going to the office. Now, am I tired sometimes? A hundred percent. Did I miss a lot of stuff with my kids? Absolutely, and I have deep regret over that. With success and money comes a price, too. Becoming a CEO at 25. "Why not me and why not now?" I live my life by this mantra. In the 1990s, no one was doing student housing at large scale nationally. I saw this white space, and I'm like, fuck it, let's do it. "I'm not afraid to fail. And I think if you're not afraid to fail, it's a freedom." "Embrace the suck." Not everything's gonna be fun. Some things are hard. But sometimes when you push through them, you get to another side. Sometimes you don't, and pulling the plug is okay if it's not working. I've gotten good at understanding that a business might be a great opportunity, a great idea, at the wrong time. When building something…If you aren't willing to make sacrifices earlier in your career and build that foundation for the future, being an entrepreneur might not be for you. I made choices to miss things with my wife and kids. Were all those things I missed worth it? Probably not. My daughters are 21 and 23 now, and I missed a lot of their early growing up. Four years ago, I apologized to my older one, and she said, "You know what, we remember this dad more than that dad." "It's never too late to make a change." After you've done okay financially, it has to be about something else. The guys and women I roll with—"it's not about money. You either are wired to get up and work hard every day and do it, and it has to be about something else." It could be about providing opportunities for the people who work with you, or solving complex problems, or creating a business you're excited about. "I don't think I'm the smartest guy in the room." You have to be open to learning. I continue to want to learn about other people's businesses. If I meet somebody, I'm like, tell me about that business. If you have that inquisitive mind, some guy tells me he's in the widget business, and I'll think of ten things they should try to do. "I am never too embarrassed to say I don't know something." When we were selecting architects and contractors for the arena, I spoke to owners of the newest stadiums. Just lessons learned about the process. When I mentor kids, I tell them most people are afraid to say "I don't know" or "I don't understand." "If you're embarrassed for looking stupid, isn't it worse if you don't know what you're doing down the road because you didn't ask?" "People don't know how to listen anymore. People wait to talk." They don't listen. When I have dinner with my youngest daughter, I hand her my phone so I won't be on it. I want to be there, I want to be attentive. Why are you wasting time meeting with people if you're not gonna listen to them? "Make lots of mistakes. Just don't make the same one twice." Try hard. Don't be afraid to put yourself out there. The worst thing that happens is someone says no. I met my wife in a bar, literally in line for pizza. Turns out she was the school teacher two different women had told me I needed to call. The funny part is my buddy was talking to her best friend. He married her, I married Hailey, and our kids are best friends. When it comes to sales. "Don't bullshit people. That's my number one goal." People can tell. Even at an early age, I had the humility to say I don't know everything. Here's my business plan, here's why I think I can scale Campus Apartments across the country when that wasn't being done. When I'm hiring or promoting leaders, I look for three things. One is trust—I need to trust them. Two is creating an open line of communication. Three, "I don't think you're a successful leader or CEO if you're not willing to listen." There are a lot of dictator type CEOs. That's not me. Some of them work. "I don't manage from fear, I manage from bringing in opinions." For me, it's about having people who, in their individual swim lanes, are better at those jobs than you are. The DeSean Jackson situation taught me about leading with curiosity. He made some anti-Semitic comments, and people came to me saying we need to cancel him. "Before I get there, I actually just want to find out what his intent was." The things he said were based on him being uninformed about the hurtfulness of those words. Not only was he willing to understand that, but he said, "Can you take me to your Holocaust memorial and actually educate me?" He came with his mom, no press. "It would be nice to take a moment before you're ready to convict somebody and actually have a conversation." When I'm looking at investments, I really have to understand the product. I joke, “Do my kids at least understand it?” Number two: Who's the founder? People matter. I ask myself, if this thing goes bad, and as long as the guy's not a crook, would I invest with them again? "I have to be more than just money in the deal." I like knowing when my influence and input can help make a difference. I think it's strategic thinking, introductions, and being a sounding board. The hardest part about being a founder is that they're afraid to tell investors bad news. "Bad news doesn't get better with time." Advice to young professionals. "Try to get noticed for the right reasons." Show up and go to work. Go get coffee when you see your boss's boss there. Don't be afraid to introduce yourself. Ask lots of questions. Be the person who says, "Could you explain that to me?" Folks in my position really respect that. "Don't be afraid to put out a bad idea." I hate working from home because I think people are screwed by the opportunity to interact with people and better their career and learn things. You're robbed of chance encounters, of overhearing conversations, of learning by proximity. We're building this arena in downtown Philly, not taking any city capital, and doing good things for the city. We came together with Comcast who owns the Flyers. "It's gonna be the best live entertainment venue in the world, located in Philadelphia." We're opening in 2030 with a WNBA team. For those counting Philly out, you're wrong—we're doing great shit here. Reflection Questions David's grandfather survived the Holocaust, which gives David a profound perspective on what real pressure and struggle actually look like. What experiences in your own life or family history could you draw on to reframe the "struggles" you face in your work or personal life? He lives by the mantra "Why not me? Why not now?" and says that not being afraid to fail is a freedom. What opportunity are you currently overthinking or waiting on "permission" for? What would change if you asked yourself those two questions right now? David regrets missing parts of his daughters' childhoods while building his businesses, but his daughter told him, "We remember this dad more than that dad." Meaning it's never too late to make a change. What relationship in your life needs you to show up differently, and what's one concrete thing you could change this week? More Learning From The Learning Leader Show - Mastermind Talks – How To Be Wise Beyond Your Years Reflection Questions, Humble Confidence, Building Trust Time Stamps: 01:51 David Edelman's Early Lessons in Business 03:58 Investing at a Young Age 06:12 Family History and Holocaust Survival 09:53 Balancing Ambition and Family 18:17 Sustaining Excellence and Learning from Others 25:38 The Art of Listening and Being Present 26:16 Lessons from Childhood and Parenting 26:47 The Story of Meeting My Wife 28:23 The Importance of Taking Risks 29:52 Sales and Leadership Philosophy 30:54 Building a Nationwide Business 32:07 Hiring and Promoting Leaders 35:34 Handling Controversy with Compassion 38:15 Investment Strategies and Favorite Ventures 41:36 The Future of Philadelphia's Arena Project 44:05 Advice for Young Professionals 46:45 EOPC
/episode/index/show/learningleadershow/id/39154435
info_outline
663: Priya Parker - The Art of Gathering with Purpose: Power, Preparation, Magical Questions, and the Psychology of Bringing People Together
11/24/2025
663: Priya Parker - The Art of Gathering with Purpose: Power, Preparation, Magical Questions, and the Psychology of Bringing People Together
Go to for full show notes Join tens of thousands of leaders pursuing excellence: This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: Priya Parker is a master facilitator, conflict resolution expert, and author of the bestselling book The Art of Gathering: How We Meet and Why It Matters. Priya has spent decades facilitating difficult conversations in boardrooms, communities, and conflict zones. In this conversation, she reveals the mechanics of meaningful gathering and why most of us are doing it wrong. Key Learnings A facilitator is interested in the life of a group. I think of facilitation as working with people who are interested in the infrastructure of three or more people who need to come together and are ideally changed for the better by what transpires between them. A facilitator thinks deeply about how to set up the conditions to increase the likelihood that transformation happens. Great facilitators are obsessed with language. There's listening to make someone feel heard, but the difference between green facilitators and seasoned ones is an obsession and ability to hear, recall, and play with language. You have to understand what people are actually saying and be able to reflect it back in ways that unlock new meaning. Understanding power is essential to facilitation. You need to know how decisions are being made, who is talking more than others, when to allow for that, and what your own relationship is to holding the group. When do you shut up? When do you pull people out? When do you push back? All of this is fundamentally about understanding power dynamics. I'm a third-generation ostrich. On both sides of my family, when conflict arises, we stick our heads in the sand. Nothing to see here, folks. But I've cultivated the ability to hold heat. Even now, when facilitating a reckoning and the heat rises, my palms still get sweaty, I can feel my heart racing, blood rushing to my cheeks. But I've learned how to stay present with that discomfort. Counterintuitively, having deep empathy for people who want to flee makes me more effective. "90% of the success of what happens in the room, and as a facilitator, happens before anybody arrives." This is what my mentor Randa Slim taught me, and it's absolutely true. The construction of the house happens before anyone gets there. Dr. Hal Saunders changed everything for me. He was an American diplomat who served five presidential administrations and was part of the Camp David Accords. After leaving government, he realized that while governments can create peace treaties, people's perceptions of each other on the ground haven't necessarily changed. He trained me as a teenager in sustained dialogue, and I learned facilitation the way it should be learned—through apprenticeship. Even in his seventies and eighties, he always believed he had something to learn. The first questions people ask you signify what they value. When I arrived at the University of Virginia, people kept asking, "What are you?" I learned quickly that they meant racially. My mother, an anthropologist, had taught me that the first questions a community asks reveal what matters most to them. Race was clearly very important there. I made myself a conflict resolution facilitator. Growing up between two vastly different households—toggling every two weeks between a vegetarian, Buddhist home where the word "God" was never mentioned and an evangelical Christian home where we never ate before saying Grace. I became deeply interested in when and why and how people come together, what they think of as normal, how they create and change cultures, and how they come apart. Your highest real estate is when people are together in the same place at the same time. Wasting time in the room figuring out what to say or do is actually wasting everyone's time. A huge part of preparing for any gathering is figuring out what the right conversation is for this group to have, and how to equip them to have it well. Think of military pre-mission briefs. They're really good at setting mission objectives. This is the goal, this is what we're striving for. Then they debrief afterward to learn and do better next time. That same discipline applies to any gathering, whether it's a leadership retreat or hosting dinner at your house. Every gathering is a social contract. You're creating a temporary constitution. At a dinner party, there's an implicit rule: bring a bottle of wine. People find out they've broken the constitution when someone says, "Wow, they didn't even bring a housewarming gift." We have all these implicit norms, and in diverse groups... Which is every group, not just racially, but people with different assumptions about how things work—you need to make the contract explicit. Elizabeth Stewart ran a startup networking organization and wanted it to be a true community, not just a shark tank for pitches. She created a pop-up rule: you can't talk about what you're selling. No pitches. Super counterintuitive for a networking night, but it created exactly what she wanted... Trust and long-lasting relationships rather than transactional encounters. The rule signified what she was trying to create. Using your power as a host means protecting your guests. You're temporarily equalizing people so they can coordinate group life. Gathering is fundamentally a coordination problem: helping people understand what the rules are, protecting them, and connecting them. There are moments when you should surprise people. If a team is stuck in a 50-year-old institution that's always done things the same way, and they'll die institutionally if they don't change, maybe the purpose is to build their skills for discomfort and navigating uncertainty. In that case, maybe you don't tell them the full roadmap because the practice itself is learning to navigate the unknown. Making things explicit and transparent equalizes the room. Showing the roadmap is deeply beneficial, particularly to people with less power and knowledge. For newer people who don't know how things work, for people with other obligations like tending to an elderly parent or being a student athlete with fixed schedules, transparency helps level the playing field. But it may not always be your purpose. Before you default to a dinner party, ask what you actually need. If the goal is to laugh hysterically and create memories with friends you don't see enough, a dinner party might not be the best form. Maybe you should play kickball in the park, stage a made-up pickleball championship, go to a morning rave, or take a party bus to a concert. We're so boxed into thinking about how adults must hang out. When hosting dinner parties, keep the menu relatively simple. Increase the meaning dial and it decreases the pressure on food quality. Think about food that tells a story. The invitation matters deeply. I could send an invitation: "Come enjoy my best attempts at Ruth's BLTs." My grandmother's recipe that takes me back to childhood. I tell the story in the email, narrow the expectations, and create a social contract. This is for BLTs. If you're a vegetarian, you can take out the bacon. And please don't bring your mushroom penne, not in this context. Then I ask: bring a story of a dish that takes you back to childhood. The whole night plays itself. Magical questions are questions everyone in the group is interested in answering, and everyone would be interested in hearing each other's answers. It's a magical equation. It's subjective and relative to each group. My seven-year-old daughter once asked at dinner: "What's the naughtiest thing you've ever done that was worth it?" We laughed and shared for two hours. My son asked my elderly father: "What's the meanest thing you ever did to anybody before the age of 15?" That caveat, before age 15, temporarily equalized everyone at the table. Testing and practicing are how you develop the muscle. I test questions on my team, I think through social arithmetic: what do these specific people have in common, what don't they have in common, what's the right level of vulnerability? I ask my community on Instagram and Substack to share their magical questions. Someone from Brazil sent me: "Would you rather spend 10 minutes on the moon or one year traveling through Europe?" It inspires heated debates in his friend group. My favorite question for virtual groups: "What was the first concert you ever went to, and who took you?" People pause, then you see a waterfall of answers—Bonnie Raitt, Madonna, New Kids on the Block. Everyone's interested in seeing everyone else's answers. You realize who's here, you see there's someone behind everyone (my sister, my mother, my college girlfriend), and you increase the likelihood that people realize these are real humans. Creating psychological togetherness on Zoom is my single most important skill. During the pandemic, I lost all my physical facilitation tools. I couldn't chase someone into the bathroom to convince them to come back, couldn't use my body to signal it's time to quiet down. I was just a little green square. Magical questions became my most powerful tool for creating psychological togetherness when people aren't in the same room. Ryan's champagne question works because it's visceral and emotional. "We're meeting exactly one year from today and popping bottles, what are we celebrating?" That's not "what's your goal for the year." That's boring. You pop champagne for something that matters emotionally. It's a somatic, physical question that forces people to think big because you're not popping champagne about something boring. The responsibility of gathering is about both connection and power. Particularly in work contexts, you can ask questions that are too vulnerable or that aren't appropriate. You need to protect your guests by ensuring questions relate to the purpose of the convening. Asking "what's a core experience from your early life that connects to why you do the work you do today?" helps people understand motivations without crossing lines. Questions can open up the world. They're a sequence of words that, if you ask them in a specific way, can fundamentally change what's possible. Being genuinely curious and fascinated about people and their stories and life experiences will change your life. Full stop. Writing The Art of Gathering let me articulate what deeply frustrated me about gatherings and try to convince other people it should frustrate them too. What's been beautiful is that people are starting to get fed up with mediocre gatherings and expect better of how we spend our time together. They're realizing we can change it with some thought, some temerity, some bumping around. The pandemic made the book even more relevant. The paperback came out in April 2020, when gathering was banned, which was super awkward. But by taking gathering from us, we began to see it. We began to see that this thing we took for granted shapes our lives—how we wed, fight battles in court, host funerals, host galas. People started asking first-order questions: when and where and why should we meet, and who decides? That's a powerful question to be asking. Anyone can gather. Many of the hundred gatherers I interviewed for the book identified as introverts, loners, people on the outside of things, people with social anxiety. As one person said, "I create the gatherings I wish existed in the world. And other people seem to like it." Reflection Questions What gathering in your life, whether a team meeting, family dinner, or community event, would be transformed if you paused to clearly define its purpose before diving into logistics and form? Think about a group you're part of where people come from different backgrounds and assumptions. What explicit "social contract" or ground rules could you create to help everyone understand how to show up and what's expected? What's a magical question you could ask in your next gathering that everyone would be interested in answering and everyone would want to hear each other's responses to? More Learning From The Learning Leader Show - Mastermind Talks – How To Be Wise Beyond Your Years Reflection Questions, Humble Confidence, Building Trust
/episode/index/show/learningleadershow/id/39065015
info_outline
662: Nicholas Thompson - The Atlantic CEO on Growing Up With a "Precariously Insecure" Genius Father, Hiring Leaders with an Edge, How Running Builds Discipline, and Why Moving at an Uncomfortable Pace Built a Million-Subscriber Media Empire
11/17/2025
662: Nicholas Thompson - The Atlantic CEO on Growing Up With a "Precariously Insecure" Genius Father, Hiring Leaders with an Edge, How Running Builds Discipline, and Why Moving at an Uncomfortable Pace Built a Million-Subscriber Media Empire
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: Nicholas Thompson is the CEO of The Atlantic and former editor-in-chief of WIRED. He's the author of the best-selling book (and one of my favorites of the year), The Running Ground. Nick shares why great leaders must balance being decisive with staying open to being wrong, how to build teams that challenge your thinking without creating chaos, and why the most important skill for the next decade is knowing what questions only humans can answer. Key Learnings Consistency Over Intensity Creates Results - If you go out there every day, six or seven days a week, and a couple days you push yourself really hard, you get faster. There's no two ways about it. If you don't do that, you don't get faster. It's a very good reminder that you can get a lot done if you just go and allot time to pushing yourself. Recommendation letter written by the Stanford faculty about Nick's dad to be a Rhodes Scholar: “Scotty Thompson is the kind of young man that comes along only once in approximately ten years. I cannot recall ever having known a student who possessed the same combination of intelligence, creativity, energy, drive, and dedication. He has attempted more, achieved more, than anyone we have studied– including some who now hold high office. He is generally conceded among those who have observed the student body since World War II to be the outstanding leader of the era. I think it likely that in the entire history of Stanford campus life, he has had no near rival since Herbert Hoover as an undergraduate.” Also about Nick's Dad: Tracy Bennett, one of his graduate students, said, “He was flamboyant, gently endearing, annoyingly arrogant, piercingly intelligent, entertaining, and more. I’d never met a man, nor had a professor, who was clearly so brilliant and at the same time so precariously insecure.” His grandfather, Frank Thompson, placed second in the Southern California extemporaneous speaking contest held at Whittier College. First place was Richard Nixon. Parenting — “Nothing makes me more worried about failure than parenting.” “Parenting is suffused with regrets, confusion, and mistakes. But when I run by, I know my children are rooting for me to succeed with infinite love and enthusiasm.” Running hard... Pushing yourself. Why do it? “Discipline builds discipline. Discipline is cumulative.” Sometimes You Have to Trick Yourself - I ran 10:48 because the track was bigger than I thought, and I didn't realize how fast I was going. If I had known I was running at a 5:23 pace, I would've shut down. My body would've started to hurt. Sometimes you can't let yourself know what you're actually doing, or you'll get scared. Hiring at The Atlantic - The people he hires at The Atlantic share four must-have attributes: A spirit of generosity. A force of ideas. They're relentlessly hard workers. And they have an edge: an anxiety about getting great work done. That last one stuck with me. The best people aren't just talented... They're driven by a productive anxiety to do work that matters. Becoming CEO of The Atlantic: The Search & Selection: The Atlantic conducted a yearlong search after President Bob Cohn left in fall 2019. When owners Laurene Powell Jobs and David Bradley announced Thompsont in December 2020, they said "Nick is singular; we've seen no one like him" and that he brought "a surround-sound coverage of relevant experience." Move at an Uncomfortable Pace - You don't get anything you want by being comfortable. If you're working in a way that feels easy and setting deadlines where everything seems smooth, you're not growing, you're not learning, you're not getting there. That's a lesson from running, and it's a good lesson for work. Set Audacious Goals - We're setting two extremely big goals at The Atlantic. Our projections don't suggest we're going to hit them. But the same was true last time when I said we're gonna get profitable and a million subscribers in three years. We got there. Sometimes having a really big goal motivates you and forces all the tough choices. Continuous Forward Motion Matters Most - When I realized yesterday's marathon was going badly, I kept telling myself: continuous forward motion. Sometimes the goal becomes just finishing. It's better to make a full drop in pace and hold that than to slowly slide backwards every mile once you know you won't hit your goal. Every Extra Word Is an Opportunity to Lose People - Every extra word, every extra thought, every extra detail that doesn't propel the story needs to be removed. This book is 75,000 words, but there's 60,000 words I cut. Is this sentence absolutely essential? No? It's gone. That's storytelling, and that's leadership communication. The Cocktail Party Test for Storytelling - If you describe what you're writing at a cocktail party, do people come towards you or walk away? I can talk about my 2005 cancer diagnosis and 2007 marathon, and people lock in. I talk about my 2009 marathon, and no one cares. Test what has emotional resonance with your friends. Write and Speak To Help People SEE a Movie - When somebody's reading, they're visualizing it in their mind's eye. Can you see it? Can you feel it? If you can't run a movie in your head about what I'm writing, it shouldn't be on the page. Help them visualize it—the little white house in Concord, walking around Walden Pond. Hiring: Spirit of Generosity and Force of Ideas - Spirit of generosity means can they work with people? Will they be territorial or figure out what's best for the org? Force of ideas means are you smart and sharp? I also want edge—a little bit of productive paranoia. Not complacent, but kind to everybody. Discipline Can Show Up in Different Ways - My editor-in-chief hasn't run a mile in 25 years. Is he disciplined? Hell yeah. Works all the time, focused on every sentence. You can have mental discipline without physical discipline. I try to get the most out of different kinds of people with different strengths. Keep Going - This is the hardest time to graduate because of AI and uncertainty. Find things you're passionate about and really focus on them. My twenties weren't great professionally. I found journalism, but I wasn't good at it yet. Keep pushing, and eventually things turn out for the best. Reflection Questions What would happen if you moved at an uncomfortable pace in your most important work? Where are you setting deadlines that feel too easy and smooth? Are you ruthlessly cutting everything that doesn't propel your story forward? What sentence, meeting, or project exists simply because it always has, not because it's essential? Former Episodes Referenced - The Comfort Crisis - Main Street Millionaire - Be So Good They Can't Ignore You Time Stamps: 02:05 Nick's NYC Marathon Experience 03:35 Nick's Father's Legacy 11:43 Running and Leadership 17:08 Overcoming Cancer and Running Again 19:24 The Importance of Setting “Stretch” Goals 21:30 Marathon Challenges and Lessons 27:09 The Warrior Athlete and Early Lessons 28:54 Nick's Role as CEO of The Atlantic 29:30 Unique Talents for a CEO Role 30:42 Balancing Multiple Interests 32:30 Writing 'The Running Ground' 37:37 Crafting a Compelling Story 41:24 Storytelling Tips for Leaders 44:15 Hiring the Right People 51:55 Running and Parenting 54:06 Advice for New Graduates 56:07 EOPC
/episode/index/show/learningleadershow/id/38992500
info_outline
661: Suzy Welch - How to Identify Your Core Values, Close the Authenticity Gap, and Live with Purpose
11/10/2025
661: Suzy Welch - How to Identify Your Core Values, Close the Authenticity Gap, and Live with Purpose
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Suzy Welch is known for co-founding the Jack Welch Management Institute and writing bestsellers like 10-10-10: A Life Transforming Idea. Her career includes roles as an editor-in-chief for Harvard Business Review, a crime reporter, and a professor. She teaches at NYU and is the best-selling author of Becoming You. Key Learnings Purpose Requires Realism, Not Just Passion - Everyone wants to be the drummer in Disturbed, but that guy's good at drumming. My whole methodology is about realism. You have to know what your values are, what your interests are, but you better be good at it or forget it. Otherwise, it's a hobby. Values Are Choices, Not Virtues - Most people confuse values and virtues. Virtues are things like integrity, courage, and thankfulness... Behaviors we all should have more of. Values are choices about how you want to live, work, and relate. It's a value if it would drive who you married, what job you took, and where you went on vacation. There are 16 Measurable Values - Values exist on a continuum like a DNA profile. Scope reflects how exciting a life you want. Radius is how much you want to change the world systemically. Belovedness is how important an intimate relationship is to you. Work centrism is whether you love work for work's sake or if it's just a means to an end. Men Over 32 Value Romantic Relationships Most - We just got data showing that for men over the age of 32, belovedness is their number one value. It's much lower for women. Only 50% of people have family centrism in their top five values—we assume everyone shares our values, but they don't. Your Authenticity Gap Reveals Your Pain - You could hold the value of scope as number one, but not be able to live it right now because of your job or family situation. That gap between what you value and what you're living—we call that your authenticity gap. If you've got a big one, you know it because it hurts. Gen Z's Top Value Is Self-Care - 75% of Gen Z have self-care, wellbeing, pleasure, and leisure as their top value. Their top three are self-care, authentic self-expression, and helping others. Meanwhile, hiring managers want achievement, scope, and work centrism. The overlap is 2%. Aptitudes Are Your Brain's Dominant Hand - We have nine cognitive aptitudes preset by age 15. Are you a generalist or a specialist? A future focuser or a present focuser? A brainstormer or someone who comes up with one fully baked idea per year? It's painful to be a generalist in a specialist job. Your Personality Is How The World Experiences You - Your personality is not the list of adjectives you write about yourself. It's how the world experiences you. When I did my 360 feedback, people said I was the hurricane, not the calm at the center. I had to learn to communicate better the thoughts I had, and learn to be less chaotic. Everyone Writes Themselves As The Hero - A police lieutenant once told me: everyone writes the story of their life with themselves at the center as the hero. No matter what story we tell ourselves, we always cast ourselves as the hero. That's why self-awareness is so hard and why we need testing, not just self-reflection. The Aperture Problem: Kids Only Know Five Jobs - When kids come out of high school, they only know about five jobs, two of which are their parents. By college it goes up to seven. By grad school, MBAs are thinking about two or three options—banking, consulting, or tech. There are 135 industries and thousands of types of work nobody tells them about. Great Leaders Don't Do It For The Money - I've been blessed to know many of the greatest leaders. They're doing it for love of people, excitement, work, or impact. I've never met a great leader who was doing it for the money. Jensen Huang and Jeff Bezos are examples—clarity, vision, excellence in everything, no shortcuts. Better To Be The Author Than The Editor - When you're ambitious, you end up surrounded by voices and can become the editor of your life. You have to become the author. Paint a self-portrait of yourself standing still so that when you start running, you know where you're going and why. Reflection Questions What would the 5 people closest to you say about how you show up? Would their description match how you see yourself, or do you have a self-awareness gap you haven't addressed? If you mapped your actual daily behaviors against your stated top values, would they align? Or are you living someone else's version of success while calling it your own? Are you the author of your life or the editor? Whose voices are loudest in your head when making big decisions, and have you given yourself permission to write your own story? Former Episodes Referenced - How Originals Impact the World - How to Build Credibility, Solve Problems, & Multiply Your Impact - Answering Life’s Great Question
/episode/index/show/learningleadershow/id/38898170
info_outline
660: James Clear (Live at Ohio University!) - The Four Laws of Behavior Change, Systems vs Goals, Building Better Habits, Mastering the Two-Minute Rule, Having a Great Marriage, & The Plateau of Latent Potential
11/03/2025
660: James Clear (Live at Ohio University!) - The Four Laws of Behavior Change, Systems vs Goals, Building Better Habits, Mastering the Two-Minute Rule, Having a Great Marriage, & The Plateau of Latent Potential
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: James Clear is the author of one of the most influential books of our generation, Atomic Habits. He’s sold over 25 million copies worldwide and has helped millions of people transform their lives through the power of small changes. We brought the podcast to the campus of Ohio University, where we recorded live in front of 250 of the most impressive college students I've ever met. Notes: I loved the Morgan Housel moment - It was cool to see James' reaction to it (you can watch it on ). Morgan said, “I have absolutely not a single cell of envy for him. Because he is the nicest guy you will ever meet. You will not meet a nicer human than James Clear. You will not meet someone as successful as he is and as humble as he is. He is a saint in my life. And because of that, I adore every bit of this guy, so I cannot envy him. I am just inspired by his success, full stop." We should all strive to be that for the people in our lives. Your WHO - “Every opportunity in life comes through a person. Relationships are usually the most important thing. If you want to achieve more, there is a relationship that can unlock better results. If you want to make a meaningful contribution, helping others is a great way to do it. If you sim Willpower – 'People with tremendous self-control aren't that different from those who struggle. They're simply better at structuring their lives in a way that doesn't require heroic willpower.' It's not about determination, it's about design. That's liberating. Fall in Love with the Process - "When you fall in love with the process rather than the product, you don’t have to wait to give yourself permission to be happy. You can be satisfied anytime your system is running. And a system can be successful in many different forms, not just the one you first envision." Make It Obvious, Easy, Attractive, Satisfying - The four laws of behavior change: make good habits obvious and bad habits invisible, make good habits easy and bad habits difficult, make good habits attractive and bad habits unattractive, make good habits satisfying and bad habits unsatisfying. Use the Two-Minute Rule - Scale any habit down to something that takes two minutes or less. Want to read more? Read one page. Want to run a marathon? Put on your running shoes. The goal is to master showing up and make the entry point as easy as possible. Standardize Before You Optimize - You can't improve a habit that doesn't exist. Master the art of showing up before worrying about optimization. Build consistency first, then work on increasing the dose or improving performance. Track Your Habits Visually - I use a paper clip strategy: start each day with 120 paper clips in one jar, move one to another jar each time I complete a writing session. Visual tracking provides clear evidence of progress and makes the habit satisfying. Habits Need to Match Your Personality - There's no one-size-fits-all approach. Morning people and night owls need different strategies. Work with your natural tendencies, not against them. Choose habits and contexts that align with who you already are. Create Commitment Devices - Make bad habits difficult through commitment devices. I had my assistant change my social media passwords every Monday and only give them back on Fridays. This eliminated mindless scrolling during my productive work hours. Focus on Systems, Not Goals - Winners and losers have the same goals. The difference is their systems. Goals are about the results you want to achieve; systems are about the processes that lead to those results. Fall in love with the process, not the outcome. Build Habits That Align With Your Desired Identity - I wanted to be a writer, so I wrote every Monday and Thursday for years. Eventually, I had proof. I couldn't deny I was a writer because of the body of work I'd created. Your habits are how you embody your identity. The Plateau of Latent Potential - We expect progress to be linear, but it's not. Habits often appear to make no difference until you cross a critical threshold. You need to persist long enough to get through the plateau and break through to the other side. Reduce Friction for Good Habits - I want to work out more, so I lay out my workout clothes the night before. When I wake up, they're the first thing I see. The easier you make the habit, the more likely you are to do it. Increase Friction for Bad Habits - Want to watch less TV? Unplug it after each use and put the remote in another room. The added friction makes the bad habit less appealing and gives you a moment to make a better choice. Automate Good Decisions - Technology can lock in good behavior. I set up automatic transfers to my investment account. Once the system is in place, the good behavior happens without requiring willpower or decision-making energy. Student Questions On Building Habits in College - The mess of college is actually useful because you're forced to figure out who you are. Use this time to experiment with different habits and see what sticks. You have more flexibility now than you will later in life. On Breaking Bad Habits - Trying to eliminate a bad habit without replacing it with something else is really hard. The more sustainable approach is habit substitution. If you want to stop scrolling social media, replace it with reading for five minutes instead. On Staying Consistent - Never miss twice. Missing once is an accident; missing twice is the start of a new habit. Elite performers aren't consistent because they're more disciplined—they have better strategies for getting back on track quickly when life happens. On Finding Your Purpose - I think the idea of finding your purpose is misleading. You don't find your purpose; you build it through the habits you practice daily. Your life is essentially a collection of your habits, so if you want a different life, build different habits. On Overcoming Setbacks - After my accident, I had to redefine what success looked like. Sometimes progress means recovering what you lost rather than reaching new heights. Focus on what you can control today rather than what you wish you could control. On Reading and Learning - I read across many disciplines because insights often come from connecting ideas from different fields. Read widely, take notes, and revisit those notes regularly. The goal isn't to finish books—it's to find ideas that change how you think. On Building a Writing Practice - I published twice per week for years before anything took off. Most people overestimate what they can accomplish in one year and underestimate what they can accomplish in ten years. Show up consistently and let time do the heavy lifting. Reflection Questions Are you focused on achieving goals or building systems? What's one process you could improve this week that would make your desired outcomes more likely? What's one habit you want to build? Can you make it so easy that you can't say no—something that takes two minutes or less? How can you design your environment to make this habit obvious and attractive? Which of your current habits align with the identity you want to build? What small votes can you cast today through your actions to prove to yourself who you want to become? Former Episodes Referenced - Becoming an Optimist, Creating Your System, & Setting Up Your Future Self - The Simple Formula For Happiness, Betting on Others, & Gaining Independence & Purpose - Becoming a Super Communicator - Building Your Culture, Solving Hard Problems, & Winning The Learning Contest - Asking Better Questions, Taking Action, & Doing A+ Work Episode Timestamps: 02:20 High Praise from Morgan Housel 04:08 Winning the St. Gallen Symposium & James’ College Experience 07:00 The Strategy Behind Writing Atomic Habits 13:58 Designing Your Environment for Success 31:05 The Art of Building Genuine Relationships 39:00 Clarifying Your Thoughts Through Writing 40:11 Applying Atomic Habits to Leadership 41:04 Mental Performance Techniques from a Navy SEAL 43:31 Balancing Success and Personal Life 47:56 The Importance of Reflection and Review 51:10 Adapting Habits in Different Environments 55:19 Habits for Short-Term Goals vs Long-Term Goals 01:04:27 Using Feedback for Habit Building 01:07:55 Internal Dialogue While Building Habits 01:13:28 The Influence of Others on Forming Your Habits 01:17:01 EOPC
/episode/index/show/learningleadershow/id/38806235
info_outline
659: Derek Sivers - Not Waiting for Permission, Hell Yeah or No, Leadership Lessons From The Dancing Guy, & Why The Standard Pace is for Chumps
10/26/2025
659: Derek Sivers - Not Waiting for Permission, Hell Yeah or No, Leadership Lessons From The Dancing Guy, & Why The Standard Pace is for Chumps
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Derek Sivers is the founder of CD Baby and author of "Hell Yeah or No" and "Useful Not True." He shared how he graduated from Cal Berkeley in two years instead of four because the "standard pace for chumps" - a lesson that shaped his entire career of institutional skepticism and unconventional thinking. From creating viral shipping emails to understanding why explorers make bad leaders, Derek shares why being busy means being out of control, how your first thought is an obstacle to your best work, and why you can't predict what the world will want from you until you try everything and listen closely to what it's telling you. Notes: No Speed Limit – Most things are paced so the slowest person can keep up. If you're driven and motivated, you can go so much faster than the standard pace. I graduated from Berkeley in two years by learning four semesters of harmony in one hour. "The standard pace is for chumps. You can do so much better than that." Question the Standard Process – When someone says you must go through usual channels or something will take a certain time, assume there's probably a hack. Develop institutional skepticism - there's usually a better way than how most people do it. Create Opportunities, Don't Wait for Them – You don't have to wait until a company is hiring. If you can see how to benefit them, walk in and show them what you can do for free first. Alan Tepper made Warner Brothers more money than anyone that year by just showing up with a plan. Make Everything Valuable to Others – The starving artist spends all their time on work valuable to them but not to others. Use money as a neutral measure - if you can make money with your art, it ensures what you're doing is valuable to other people. "It's almost impossible to predict what the world will want from you... Keep yourself out there and listen closely to what the world is telling you it wants from you." Stand Out by Being Different – Don't imitate what everyone else is doing. I wrote a silly shipping email in 10 minutes that became one of the most viral emails ever mentioned in business books. Ask yourself constantly: What has nobody done before? The First Follower Creates the Movement – We focus on the shirtless dancing guy, but the first follower is what made everything happen. Until then, people kept their distance from the freak. If you find someone doing something great, follow them and show others how to follow. Every Sentence Must Matter – My books are 90-100 pages, but start as 1,000-page rough drafts. I spend 1-2 years full-time chopping every sentence that doesn't absolutely need to be there. "I'm not gonna put a single sentence out into the world that doesn't need to be there." Make every word count - eliminate everything that doesn't add value. Hell Yeah or No is Context-Dependent – This tool is for when you're overwhelmed with options and need to raise the bar. Straight out of college, say yes to everything because opportunities are like lottery tickets. Once something rewards you, then say no to other things and double down. Busy Means Out of Control – "Busy to me implies out of control. You're busy if you've let other people shove shit into your schedule." Leave space instead of filling it - that time to think is what creates valuable insights others don't have time to develop. Your First Thought is an Obstacle – Don't honor the thought that came first. In brainstorming, acknowledge the first idea, then keep going - don't stop at two or three. Even silly ideas can seed great ones you'd never reach without that stepping stone. All Beliefs Are a Myth – People worshiped Zeus for centuries; now we call it mythology. But we say our own beliefs are true while others' are superstitions. I expected China to be awful from American news, but found it wonderful - question what you've been told. Use Prejudice as Your Compass – If you notice you're prejudiced against something, that's exactly what you should explore. Burning Man sounds awful to me; therefore, I should probably go. Steer into your biases to overcome them and gain new perspectives. Explorers Make Terrible Leaders – Explorers try everything and change direction constantly, which frustrates teams. Leaders go in a straight line to a clear destination, unwavering in mission even if the path changes. I loved changing my mind, which made me a bad leader until I learned the difference. Set projects with clear missions, even if you're personally exploring other things. Try Everything Until the World Says Yes – I had a booking agency, a record label, a recording studio, and my own music - all failures. Then, a side project to help friends (CD Baby) took off. You can't predict what the world wants from you, so try many things and listen closely to what it's telling you. Reflection What "standard pace" are you accepting in your business or career that you could actually accelerate if you questioned it? Where have you assumed something has to take a certain amount of time just because that's how it's always been done? Are you spending time on work that's valuable to you but not to others? How could you test whether what you're creating actually solves problems people are willing to pay for? Are you acting more like an explorer or a leader right now? If you're constantly changing direction, how could you set clearer missions for your projects while keeping your personal explorations separate? Resources & References Derek's Content: Derek's and "" (First Follower) TED Talk - Derek Sivers "" essay Former Episodes Referenced - Chasing Your Curiosity - The Creative Process of a Comedian - Confidence, Curiosity, Connection Episode Timestamps 02:20 Early Life Lessons from Kimo Williams 05:21 Corporate Lessons and Unconventional Paths 09:10 The Power of Adding Value 13:57 Viral TED Talk: Leadership Lessons from the Dancing Guy 22:03 The 'Hell Yeah or No' Philosophy 27:29 The CD Baby Experience 28:02 Starting an Online Record Store 29:10 Creating a Unique Shipping Notice 30:01 The Viral Impact of Creativity 32:53 The Importance of Regular Writing 35:17 Questioning Assumptions and Beliefs 36:23 Exploring New Perspectives 40:41 The Explorer vs. The Leader 48:21 Advice for Aspiring Leaders Resources: Read: Read: Read: To Follow me on X:
/episode/index/show/learningleadershow/id/38724860
info_outline
658: Dave Berke - From Top Gun to Extreme Ownership: Managing Ego, Building Humility, Emotional Detachment, Agile Planning, and Leading Teams Through Chaos
10/19/2025
658: Dave Berke - From Top Gun to Extreme Ownership: Managing Ego, Building Humility, Emotional Detachment, Agile Planning, and Leading Teams Through Chaos
Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: Dave Berke is a retired US Marine Corps Officer, TOPGUN Instructor, and now a leadership instructor and speaker with Echelon Front, where he serves as Chief Development Officer. As a F/A-18 pilot, he deployed twice from the USS John C Stennis in support of combat operations in Iraq and Afghanistan. He spent three years as an Instructor Pilot at TOPGUN where he served as the Training Officer, the senior staff pilot responsible for the conduct of the TOPGUN course. Notes: July 2001: Plans Don't Survive Contact - Dave's Top Gun graduation exercise as flight lead. Wingman yells, "Showtime one-one break right!" - an F-5 snuck into formation. Dave was staring at the radar instead of looking out, had to fall out of formation, and ended up at the back instead of leading from the front. Mission successful, but nothing like he planned. Dave: "The outcome was still really good... except it was nothing like I thought it was going to be." Lesson: You're planning for the success of the outcome, not how you're going to do it. The most important attribute in a leader is humility. To be effective, you must be able to listen, learn, be flexible, and admit you’re wrong sometimes. One of the biggest issues they deal with when working with leaders is ego and/or the inability to be humble. As leaders, we need to be self-aware enough to realize when our ego is getting the best of us. And surrounding ourselves with people who will help us know when that is happening as well. Be Fluid with Plans, Deliberate with Outcomes - Be really fluid and loose with plans, but deliberate about aligning the team on outcomes. Dave grew up as a control freak, OCD planner. Dave: "In life, it's just not how life works... If you can align on the mission and outcome, and you are very open-minded that there are a lot of different ways to get there, you're far more likely to be successful." The military saying, "The enemy gets a vote." Ryan's quarterback coach after an interception: "He's on scholarship too, you know?" Process: How You Create It Matters Most - Process is important, but how you create it matters most. If you agree on the outcome, the conversation should be less about agreement, more about "When you talk about step one, what are you thinking? How does this lead to step two?" The process has to be organic. When you create it, you're more likely to maneuver around challenges. Book Dedication: Chris and Kat - Book dedicated to Corporal Chris Leon and his mother, Kat. Chris was a radio operator on Dave's 13-man Anglo team. June 20, 2006, Chris was killed by an enemy sniper in Iraq - first Anglican Marine killed there. Dave's son is Matthew Leon Burke - took Chris's last name. Chris's mom Kat is Aunt Kat to Dave's family. Dave: "I always say I really deep down wish I didn't know Kat, because that would've meant Chris came home and life just went on. But that's not what happened." Chris taught bravery. Kat taught strength. Top Gun Reality: It's About the Team - 1986 Top Gun most impactful movie on Dave's life at 14. But the movie depicts a lone wolf. Marine Corps teaches: Your contribution to the team matters most. A really good pilot who's self-centered will do more damage than a slightly less capable pilot who's a real team player. Dave: "If there's ever a team sport, it's going into combat... It's not about you. It's about the team." Trust: Action, Not Description - Echelon codifies relationships: Trust, respect, listening, influence. Trust is the cornerstone. Dave: "If you don't trust me, I could be good at so many things. If there is a trust gap, there's going to be a problem in the relationship and team." Trust is action you take. Ego: The Universal Challenge - When Echelon works with companies, challenges are almost always connected to ego. Dave: "Our egos tend to wreak havoc at each level of organization." From birth, the ego drives us down the wrong path. When debating plans, ego says, "You're right, he's wrong." Building good leadership is managing egos. Dave: "Humility is the most important attribute in a leader. All the attributes, humility is number one, and we don't waffle on that." Humility Enables Everything Else - Dave worked with the biggest, toughest SEALs. Attribute most critical to success: humility. Ability to listen, learn, be flexible, change, admit you're wrong, and go with someone else's plan. It even affects fitness. Humility touches everything. Doesn't diminish other attributes, but allows you to strengthen them. Teaching Humility: Subordinate Your Ego - You can’t tell someone with a big ego to be humble. Dave: "The biggest challenge with someone else's ego is not their ego. It's your ego's response to it." Most counterintuitive thing: If you clash with Ryan, Dave has to subordinate his ego to Ryan's. Lower your ego: "Hey Ryan, I've been pushing back hard, I realize I'm not listening." Natural reaction: Ryan's ego starts to drop. Over time, collaborate more. You connect success to the ability to control the ego. Dave: "Humility is the measurement of how much control you have over your ego." What you give is usually what you get. It's reciprocal. Care About Team More Than Yourself - When your people see you working hard to clear paths or block an egomaniac boss, they'll run through walls for you. Outcome of a good relationship: You care about the team, the team cares about you. That selfless act shows you care about them more than yourself. Dave: "That's how you show that you care about them more than yourself, and that's what a leader's job is, to care about the team more than you care about yourself. That's parenting, that's marriage." Extreme Ownership - Book Extreme Ownership changed Dave's understanding. When you take ownership, take ownership of everything. Caveat: Not things you literally don't control. But you have ownership over everything, even just how you react. After Chris was killed, Dave said, "That's war, nothing we can do." Problem: When he embraced it wasn't his responsibility, it meant he didn't have as much to change. Should have asked: "What is everything we can do to make sure this doesn't happen again?" The tendency is to undershoot ownership. Try to take it to the extreme. If you can take ownership of everything you can control, you get more influence over the outcome. Detachment: A Superpower - Dave: "Detachment is a superpower" - (1) almost nobody can do it, and (2) if you can, it’s massively influential. Detachment is being in control of emotions. When overwhelmed with priorities and pressures, you tend to get emotional. When you react emotionally, you make bad decisions. Learn the skill of detaching - not to be devoid of emotion (we're human), but don't let emotions dictate. Get Away from Problems to See What's Causing It - When a problem occurs at work, you tend to focus on it, go into it. It seems good but is often wrong. You should get away from it, detach. Getting away lets you look around and see what's really causing it. Military example: The enemy is shooting at you; the tendency is to focus on that. Usually bad because they're hoping you do - then they send a flanking maneuver. If you detach, step back, you'll see the flanking maneuver coming. Be able to see the future - that's the superpower. Know Your Red Flags - Intervene Early - You have to understand where you are escalating your emotions. Know your personal red flags. Most people don't go zero to 100. Long day, flight delayed, bad meeting - little things tick up, so zero is actually 4 or 5, which means dirty dishes put you to 7. When Dave gets frustrated, traps tighten up. Some people's nose turns red. If you're at level 8 and someone says, "calm down," it makes it worse. But if at level 1 or 2 and you intervene, you're in control. What an adult does: "I'm an emotional guy, but I have awareness of where I am. If I'm a 4, I gotta intervene then." If at level 10, detaching is not gonna happen. That's the difference between kids and adults. Dave: "You are much more likely to have a hard time controlling your emotions, ironically, with people you care about the most." Quotes: "You're planning for the success of the outcome, not how you're going to go about doing that, because things get in the way." "Humility is the most important attribute in a leader. All the attributes. Humility is number one, and we don't waffle on that." "The biggest challenge with someone else's ego is not their ego. It's your ego's response to it." "Detachment is a superpower." "You are much more likely to have a hard time controlling your emotions, ironically, with people you care about the most." 01:16 Introducing Dave Burke 02:21 Dave Burke's Top Gun Experience 05:23 Lessons Learned from Military to Everyday Life 07:56 The Importance of Flexibility in Leadership 13:07 The Need to Lead: Dedication and Personal Stories 16:58 The Realities of Teamwork in Combat and Business 21:03 Building Trust and Relationships in Teams 26:04 The Role of Humility in Effective Leadership 31:03 Understanding Ego and Humility 31:50 Subordinating Your Ego 33:38 Challenges of Teaching Humility 34:07 Personal Experiences with Ego 39:20 The Power of Ownership 42:57 Detachment as a Superpower 52:58 Advice for Young Leaders 57:26 Conclusion and Key Takeaways
/episode/index/show/learningleadershow/id/38568850
info_outline
657: Helen Lewis - Why Genius Is a Myth, Edison Needed Teams, Self-Promoters Are Overrated, Conspiracy Theories, Shakespeare Needed Luck, and How To Build an Excellent Career
10/12/2025
657: Helen Lewis - Why Genius Is a Myth, Edison Needed Teams, Self-Promoters Are Overrated, Conspiracy Theories, Shakespeare Needed Luck, and How To Build an Excellent Career
Go to for full show notes This is brought to you by . If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Helen Lewis is a staff writer at The Atlantic and author of The Genius Myth: Great Ideas Don't Come from Lone Geniuses. Notes: Shakespeare: Talent + Luck + Timing - William Shakespeare died in 1616 at age 52, celebrated but not yet immortal. His icon status required massive luck: friends published the First Folio (saving King Lear), then 50 years later, Charles II reopened England's theaters after Puritan closures and needed content. Companies turned to Shakespeare's IP, adapting his work (including changing tragedies to happy endings). Helen: "If anyone deserves to be called a genius, it's him. But he died as a successful man of his age. Scenius Over Genius - Brian Eno coined "scenius" - places that are unusually productive and creative. Shakespeare moved from Warwickshire to London for the theaters and playwrights. Helen: "You don't just have to be Leonardo, you also need Florence... Where do you find the coolest, most interesting bleeding edge of your field?" Modern example: Joe Rogan's Comedy Mothership in Austin created an alternative to LA/NYC for comedians like Shane Gillis and Tony Hinchcliffe. Ryan: "Put yourself in rooms where you feel like the dumbest person... force you to rise up, think differently, work harder." Tim Berners-Lee vs. Elon Musk - Tim Berners-Lee invented the World Wide Web. Has knighthood, lives an ordinary life, kids named Alice and Ben. Most people have never heard of him. Elon Musk has a lot of children, talks about his genes needing to live on, and lives a very public life. Helen: "We overrate the self-promoters, the narcissists. We demand oddness and specialness... We don't call modest people geniuses because they're too normal." Elizabeth Holmes (Theranos) and Sam Bankman-Fried (FTX) exploited this - looked like a genius (Steve Jobs cosplay, messy math prodigy) but stood on houses of cards. Trauma and the "I'll Show You" Engine - Matthew Parris wrote Fracture after noticing how many "great lives" had traumatic childhoods - loss of parents, being unloved, bullied. Helen: "I don't think that's necessarily genius in objective achievement. It's more like a hunger for recognition or fame... a kind of 'I'll show all of you' engine." Stephen Hawking on IQ - Stephen Hawking: "I have no idea. People who boast about their IQ are losers." The Flynn Effect shows average IQ rose over the 20th century through better nutrition, schooling, and living conditions. Higher IQ correlates with better outcomes. But at the top end, every IQ point ≠ is one success point. Christopher Langan (the highest IQ guy) thinks he has a theory to overturn Einstein, and that Bush did 9/11 to cover it up. No history of achievement. Helen: "Smart people don't always prosper. You need the gears that connect the engine to the wheels on the road." Conspiracy Theories: Narcissism as Driver - Narcissism is the most correlated personality trait with conspiracy thinking. Helen: "The sheeple, the NPCs think this, but I alone have seen the truth. It positions you as the protagonist of reality." The Internet is a "confirmation bias engine." But conspiracies are sometimes true (Epstein's corrupt plea deal), which is why conspiracy thinking persists. Researcher Karen Stenner's solution: Get back to depoliticized conspiracies like Bigfoot, crop circles, Area 51 - harmless things that got people outside instead of "shoot up a pizza restaurant." The Beatles: Finiteness Creates Legend - Psychologist Han Isaac said geniuses should either die before 30 or live past 80. Middle is "eh." The Beatles had both: a short career that ended definitively, then John Lennon was shot at 40, frozen in time. Paul McCartney lives on, performs at Glastonbury with John's vocals. Craig Brown: "The Rolling Stones just go on and on, but there's never as much of the Beatles as you want." Quality Over Quantity - Helen: "Incentive now is producing constantly for algorithms... That's neither fun nor produces the best work." Early career: say YES. Later career: "The most important thing you can say is no." Her metric: "Can I say honestly, that was the best I could do? I didn't cut corners. That's the metric." Podcast: advised to do 2-3 episodes weekly for rankings, has been doing weekly for 10.5 years. Shows that went daily? He stopped listening. "I'm gonna increase the quality bar, not the quantity." Robert Greene: "Do not speak unless you can improve upon the silence." Improving the Silence - "My dad's not the loudest at family gatherings, doesn't have the most words, but when he speaks, we all stop and listen. That's who you want to be." Applies to meetings: people vomit garbage to show how smart they are instead of waiting for something valuable. When you speak, people should want to listen. Thomas Edison: Execution Over Ideas - The Light bulb wasn't Edison's conceptual innovation - the idea dated to Humphrey Davy. What was incredible: Edison made it work (vacuum seal, filament) and created the New York power grid. Helen: "Lots of people can have the idea that a man should be an ant. Not everybody can write the Ant-Man screenplay and have it produced." His Menlo Park lab lasted because he worked with brilliant people on problems they cared about. Logbook shows assistants' names on breakthroughs - collaborative. We underrate logistics and execution. Most "light bulb moments" are actually slow, incremental, contested creations. Why Helen Chooses Teams Over Independence - Could go independent on Substack for more money. Works at The Atlantic for: resources, legal support, editorial integrity, and colleagues she doesn't want to let down. Helen: "You must have people in your life, you think, I wanna do work that they like. Finding those people who make you your best version of yourself." Ryan connects to athletics: "Being surrounded by people better than me forces me to raise my game. That's why we want to be part of a great team." Sample First, Specialize Later - High achievers have "hot streak" later, but sample early - trying different things, learning transferable skills. Helen: "Take the first job at a publication you could learn from. Even if not wildly interested, if it's good and they'll hold you to high standards, do it. Your second job is infinitely easier to get than your first." Work Around People Who Care - Helen: "If you work somewhere where no one cares, it's very hard. You can't care on your own. You'll become infected by the apathy around you." Nothing is more boring than a job you don't care about. Don't Wait to Live - Some devote long hours to something for money, promising they'll retire at 30 and then live. Helen: "What if you spent all that time chasing something and then you get hit by a truck? Don't wait for it. Just try and enjoy what you're doing right now." Quotes: "You don't just have to be Leonardo, you also need Florence." "We overrate the self-promoters and underrate the humble achievers." "Smart people don't always prosper. You need the gears that connect the engine to the wheels." "The most important thing you can say is no." "Do not speak unless you can improve upon the silence." - Robert Greene "You can't care on your own. You'll become infected by the apathy around you." It’s funny that we have come to use the phrase ‘lightbulb moment’ to describe a momentary flash of inspiration, because the birth of the lightbulb was slow, incremental, and highly contested.
/episode/index/show/learningleadershow/id/38481375
info_outline
656: Dakota Meyer - Medal of Honor, The Battle of Ganjgal, Leadership Under Fire, The Loyalty Question, and What America Needs Right Now
10/05/2025
656: Dakota Meyer - Medal of Honor, The Battle of Ganjgal, Leadership Under Fire, The Loyalty Question, and What America Needs Right Now
Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Guest: Dakota Meyer, a United States Marine Corps veteran and Medal of Honor recipient. At just 21 years old, Dakota's actions during the Battle of Ganjgal in Afghanistan saved many lives when he repeatedly went against his orders and drove into a Taliban ambush zone to rescue trapped soldiers. He became the first living Marine in more than 40 years to receive the Medal of Honor. Today, he's a firefighter, entrepreneur, and New York Times bestselling author. Dakota is dedicated to developing leaders who can handle crisis and complexity. In our conversation, you'll hear why Dakota believes his most heroic day was actually his greatest failure, what he was feeling the day he received the Medal of Honor from President Obama, and his practical blueprint for bringing our divided country together. Notes: The Three-Phase Life Cycle - Dakota's framework for wisdom: "You have an obstacle you face. You have to get through that obstacle and become better from it. And then the third piece is you have to share how you got through that obstacle." Leadership vs. Responsibility - "Leaders are just people too. You can lead from anywhere in an organization... Leadership comes in many forms." True leadership means choosing where your loyalty lies - with the people you're responsible for or with protecting your own position. September 8th, 2009: Leadership Failure - Dakota frames his Medal of Honor actions as "an absolute story of leadership failure at its best" - multiple levels of leaders avoiding responsibility while he went against orders to save his teammates. The Loyalty Question - "Where does their loyalty lie? Is it in the people that trust them to lead them and to protect them? Or is it in the organization in order for themselves to keep getting promoted?" This fundamental choice defines every leader. Risk vs. Results - "Organizations and leaders today are so risk-averse that risk comes before results... You can't be successful, do hard things, and stay comfortable and be safe. In no world does that exist." Mental Health Reality Check - Dakota challenges current mental health approaches: "We're giving people no hope because we're trying to accommodate their emotions and not bring them back to reality and logic." He distinguishes between trauma that needs addressing and self-induced mental health issues through poor choices. Love as Choice, Not Emotion - "Love is not an emotion. Love is a choice... If you love me, you're going to always help me be the best version of me. That doesn't always feel good." Accountability and Fatherhood - As a father of two daughters: "I can't be anything that I wouldn't let anybody else be to them... You set the bar for what they're gonna accept and what they're not gonna accept." The Civil War Warning - "America doesn't need a Civil War. What we need is to vote, to lead, to speak up in schools, to teach our kids history, truth, kindness with strength, and how to disagree without violence." The Ambush - When his team walked into an ambush, promised support assets (air support, mortars, quick reaction force) weren't available due to rules of engagement restrictions. When Lieutenant Johnson called for artillery support, saying, "If you don't give me these rounds right now, we're going to die," the response was "Try your best." The Decision to Act - Dakota requested permission to help multiple times and was denied each time. He finally went against orders with his driver, Staff Sergeant Rodriguez Chavez, making four or five trips into the valley over six hours to evacuate wounded and recover bodies. The Human Cost - Dakota describes the helplessness of watching Afghan soldiers get "mowed down" while running toward his vehicle for rescue. He performed basic life-saving measures, loaded wounded in trucks with the dead on the bottom and living on top for triage priority, and ultimately recovered some of his fallen teammates. The Immediate Aftermath - Dakota put his teammates in body bags, flew them home, then immediately returned to cleaning his truck and helping Afghan soldiers with their dead. He went back to his base alone - the only survivor of his four-man team. Mental Health Crisis - Dakota developed a destructive cycle: daily drinking (depressant), massive caffeine intake to compensate, creating anxiety and amplifying trauma. He was surrounded by people who only wanted to discuss trauma and war stories, preventing healing. Suicide Attempt - Dakota reached a breaking point where he held a gun to his head, but it wasn't loaded. This became his turning point - he made a commitment to either "rack it back and go ahead and do it, or go out and find a way to get through this and start living a life worthy of their sacrifices." The Path Forward - Recovery came through accountability rather than accommodation. Dakota emphasizes that while trauma needed addressing, he was "amplifying and feeding the problem, not the solution" through his choices. Real vs. Perceived Heroism - Dakota challenges the hero narrative: "I am an example of the potential that's in every human being... If they believe in a cause that's bigger than themselves, and they love people so much that they're willing to do whatever it takes to stop the suffering." Daily Character Building - "You don't just wake up and do the hard thing. It starts every day. Do you get up when you say you're gonna get up? Do you do what you say?" The Medal of Honor action was simply "upholding my end of the deal to my teammates and to my country." Being a Great Dad - Dakota sets an extremely high bar as a dad: "I believe that if your daughters start dating shitty and weak men, it's because you are a shitty and weak man." He sees fatherhood as the ultimate accountability. Unity through Truth - His current focus: "I just want to bring people together... I wanna put hope back in the world through truth." He believes in finding common ground with anyone through genuine connection and curiosity. Education vs. Knowledge - Dakota distinguishes between theoretical education and practical knowledge: "There's a difference between education and knowledge... those who can't do, they teach. We need more that have done teaching." The Power of Love - His core philosophy centers on love as action, not emotion: "Love is limitless... there's no expiration date" compared to hate and negativity, which "there's an expiration date on." Practical Application Leadership Loyalty Test - Before making decisions, ask where your primary loyalty lies: with those you lead or with your own advancement Risk-Taking Framework - Understand that meaningful results require accepting risk and discomfort Mental Health Approach - Address trauma while taking responsibility for choices that amplify problems Daily Character Development - Build integrity through small daily commitments before facing major challenges Connection Over Division - Seek common ground through curiosity and questions rather than attacking opposing viewpoints
/episode/index/show/learningleadershow/id/38392715
info_outline
655: Morgan Housel - The Simple Formula For Happiness, Betting on Others, Gaining Independence & Purpose, Family Vacation Secrets, The Art of Spending Money, & The Death Bed Lesson Every Leader Needs to Hear
09/28/2025
655: Morgan Housel - The Simple Formula For Happiness, Betting on Others, Gaining Independence & Purpose, Family Vacation Secrets, The Art of Spending Money, & The Death Bed Lesson Every Leader Needs to Hear
Go to for full show notes The Learning Leader Show with Ryan Hawk Morgan Housel is the New York Times Bestselling author of The Psychology of Money, Same As Ever, and The Art of Spending Money. His books have sold over 10million copies and have been translated into more than 60 languages. This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Notes: Morgan dedicated The Art of Spending Money to "Kellie the Unicorn" (his sister Kellie) after she was diagnosed with colon cancer and asked him to fulfill her long-running joke request. Sometimes book dedications "mean nothing to the reader, but they can mean everything to the author." People Who Bet on You - Brian Richards (Motley Fool boss) bet on Morgan when he didn't have to, providing unconditional support for a mediocre college writer. Craig Shapiro (Collaborative Fund) pursued Morgan for months to join his tiny VC firm as a full-time blogger when it wasn't a business necessity. What money can’t buy - Morgan once heard a story from a priest that he'll never forget… It’s from a priest who delivers the last rites in hospitals. He described the difference between what kids say to their parents when they’re about to die. The priest tells them to tell their parents what they’re most grateful for… In families with lots of problems, the kids usually talk about something that costs money. In the best families, the ones with solid relationships, the kids say the same thing every time. “Thank you for believing in me.” Making vs. Spending Money - "There are literally tens of thousands of books written on how to make money... There are virtually no books written about how to spend money." Most people assume spending needs no guidance, but wealthy people often demonstrate this isn't true. The Internal vs. External Scoreboard - Donald Crowhurst (fake sailor who killed himself seeking external validation) vs. Bernard Moitessier (expert sailor who quit before winning to avoid attention and live authentically). Modern society pushes us toward Crowhurst's external validation while we actually want Moitessier's internal satisfaction. The simplest formula for a pretty nice life: independence plus purpose. The independence to do what you want, and the wisdom to want to do meaningful things. Chuck Feeney's Wealth Example - The duty-free store billionaire first lived the stereotypical rich lifestyle, realized he didn't like it, then chose to live modestly and give away $10 billion. "I was happy when I was giving money away, and I was not happy when I wasn't giving money away." Every Dollar of Debt - "Every dollar of debt that you have is a piece of your future that someone else owns." Debt narrows the range of outcomes you can endure in an unknowable future. Money and Happiness Research - Recent studies show that earning more money only helps if you're already happy, joyful, and content. For depressed, anxious people, more money doesn't improve well-being. "It leverages whoever you are in either direction." What Money Can't Buy - The book is "40% about how to spend money to make yourself happier and 60% about realizing what money cannot do for you." Relationships, health, and personal fulfillment must come first. “Comedians are the best thought leaders because they understand how the world works, but they want to make you laugh rather than making themselves feel smart.” "Nobody gives a shit about anything other than how you make them feel." Vacation - Morgan realized while building sandcastles with his kids on the beach in Maui (10/10 experience) that building Legos at home with them was almost as good (9/10). The real value was "uninterrupted time with my family," which required travel to avoid daily distractions but pointed to what actually mattered. Ambition - Morgan's career drive crystallized while kayaking past $25 million mansions on Lake Washington in 2010: "I need to work harder. I want one of those one day." This wasn't envy but ambition - though he notes the line between inspiration and envy is thin, especially once you know the person. A high savings rate is not "saving" but is "purchasing independence." Each saved dollar buys freedom to handle life's unknowable future without someone else's schedule dictating his choices. Why Spending Is Complicated People try to fill emotional holes with material purchases Society tells us what we should like, which may not align with our actual preferences We chase peer comparison rather than personal satisfaction We overestimate the social rewards of nice possessions The Independence Framework Save money not for retirement but for freedom to handle uncertainty Debt narrows your options when life throws curveballs Independence means being able to do what you want, with whom you want, for as long as you want The Internal Scorecard "No one's watching. No one's thinking about you." When people notice your possessions, they're either imagining themselves having them or envying you for them Neither response gives you the social validation you're seeking Use money to buy independence rather than others' admiration Relationship Investments Focus on what creates "uninterrupted time with people you love" Consider how purchases enable deeper connections (bigger kitchen for family dinners) vs. impressing others Remember that belief and support matter more than material provision Purpose Morgan's purpose became clear the moment he became a father: "There. That's it... I don't matter anymore. That's the only thing that matters right there." Purpose can be parenthood, work, religion, or community, but it needs to be bigger than yourself. "Comedians are the best thought leaders because they understand how the world works, but they want to make you laugh rather than making themselves feel smart." They deliver profound psychological and social insights while focusing on how they make you feel, not their own status. Regret -- Gerontologist Carl Pillemer interviewed 1,000 Americans aged 90-100. Not a single one said, "I wish I earned more money" or "I wish I worked harder." Nearly all said "I wish I spent more time with my kids" and "I wish I were nicer to my spouse." Inspiration vs. Envy -- Morgan credits James Clear as inspiration for "The Psychology of Money" and describes him as incredibly successful yet humble and kind. This creates pure inspiration without envy, unlike other successful writers whose personalities trigger competitive feelings.
/episode/index/show/learningleadershow/id/38343515
info_outline
654: Jake Tapper - The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can't Ignore You
09/21/2025
654: Jake Tapper - The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can't Ignore You
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. The Learning Leader Show with Ryan Hawk Guest: Jake Tapper is an award-winning broadcaster and chief Washington correspondent, currently anchoring The Lead with Jake Tapper every day on CNN. He’s also the #1 New York Times best-selling author of 7 books, including The Outpost (which was later made into a movie), Original Sin, and most recently Race Against Terror. Notes: Be So Good They Can’t Ignore You. Jake: I’m in control of how hard I work. It is our responsibility to work so hard that we become the obvious choice for the job or the promotion. Be So Good They Can’t Ignore You. "I had to be so good that even though maybe on a broadcasting level I wouldn't be the number one pick... they had to give it to me." The one leadership skill that is massively important to develop… Don’t insulate yourself with “yes” people. You have to have truth tellers in your life. Who are your foxhole friends? Who are the people who are willing and able to tell you the truth? Who are the ones who love you and care about you enough to let you know when you’ve messed up? Those people are gold. We all need them. Rejection: Dr. Seuss was rejected by 47 publishers. Rejection is part of life. You have to stay in the game for a chance to win it. Keep going. And nobody will give you a job to be nice. What value do you bring to a company? How will you make your boss's life better? You get hired to solve a problem, not because someone wants to be nice. Pinned tweet since 2017 – "To see what is in front of one’s nose needs a constant struggle." -- George Orwell. A reminder to see obvious truths being obscured by spin or wishful thinking. "You Can Always Tell Them No" - Ted Koppel's crucial advice to young Jake about maintaining journalistic integrity and not compromising values for opportunities. This became a career-defining principle that Jake still follows 20 years later. The Jar Jar Binks Theory of Leadership - Successful leaders often remove critics from their inner circle, creating dangerous echo chambers. "Great people often achieve as much as they can to the point that they are able to remove from their inner circle anyone who tells them they're being an asshole or making a wrong decision." Constructive vs. Destructive Criticism - Jake learned to distinguish between useful feedback and personal attacks: "Very few of my critics are people that I actually care what they think... folks who understand I'm just trying to be a good faith operative here." Curiosity as Career Driver - Deep curiosity drove Jake from reading microfiche about MASH as a kid to investigating complex stories as an adult: "I find something interesting and I wanna find out everything I can about it." Rejection as Constant Reality - Even at his career peak, Jake faces daily rejection: "I get rejected every day... it doesn't matter that I've had New York Times bestsellers before... it's part of life." Humility Enables Learning - Accepting expertise gaps allows growth: "Having the humility to accept that I am not an expert on any particular thing... I'm a journalist, which means I try to be an expert on whatever I'm covering at that moment." Leadership Lessons From Powerful People The Inner Circle Problem: Leaders systematically remove critics until surrounded only by yes-people, creating dangerous blind spots. Jake witnessed this pattern with Joe Biden (surrounded by aides and family who weren't honest about his declining acuity) and across industries. The Solution: Intentionally maintain truth-tellers in your inner circle who care about you personally but will challenge you professionally. Creating Truth-Telling Environments: Jake encourages healthy disagreement with executive producers, acknowledges power imbalances that make criticism harder for junior staff, and creates indirect channels for feedback ("some people on the staff think..."). The Criticism Paradox: Public leaders face constant harsh criticism, making them naturally defensive. Understanding this context helps leaders distinguish between constructive feedback that improves performance versus personal attacks that serve no purpose. Following Curiosity Despite Opposition Jake's major works were all advised against by professionals: The Outpost (no military expertise) The Atlantic story of freeing a wrongly imprisoned man Biden book (started the day after the election, despite uncertainty) Key Insight: "Every single one of them, people were telling me not to do it... It's been following my curiosities even when people told me I'm not interested in that." The Hard Work Advantage: Jake couldn't compete on appearance or natural broadcasting ability, so he outworked everyone: broke stories constantly, used blogs when he couldn't get on air, and made himself impossible to ignore through sheer output. Dealing with Rejection Expect constant rejection even at a career peak Don't take rejection personally unless there's constructive feedback Use rejection as data, not judgment of worth Keep creating regardless of immediate acceptance The Wave Metaphor: Like Tom Hanks in Cast Away, timing the waves - "every code can be cracked" if you persist and find the right timing. Key Elements for Writers: Strong structure: "Act one, chase your hero up a tree. Act two: throw rocks at your hero. Act three, get your hero out of the tree." Good editor who pushes back - be willing to "kill your darlings" Life Philosophy The Acceleration Mindset: At 56, Jake is speeding up output: "I don't know how much longer I have this window where people are paying attention... relevance is ephemeral... when it leaves, it looks fucking brutal." For Young People: "So much of life is rejection... You cannot stop it... don't take it personally." Focus on developing skills and delivering value: "Nobody will give you a job to be nice... They'll do it because you have something they want." Time Sacrifice Awareness: Success requires acknowledging costs: "What I cried about is the stuff I missed that I wasn't there for because I was chasing a story or on assignment." Time Stamps: 02:46 Jake’s Dedication to Influential Figures 05:05 Hot Mic Moment in Alaska 06:59 Preparing for Big Interviews & When to Follow Up 09:01 Dealing with Criticism 12:07 The Story Behind Jake’s Pinned Tweet 13:48 Race Against Terror: The New Book 18:29 Balancing Multiple Roles 20:47 Chasing Your Own Curiosity 23:58 Sacrifices for Career Success 29:00 The Importance of Humility in Leadership 31:08 Surrounding Yourself with Truth Tellers 34:18 Healthy Tension in Team Dynamics 37:15 Understanding the Pressure on Public Figures 40:09 Empathy in Leadership 45:17 Balancing Career and Family 49:00 Advice for Aspiring Journalists and Writers 52:01 The Reality of Rejection and Hard Work 57:26 The Importance of Structure and Editing in Writing 01:01:16 End of the Podcast Club
/episode/index/show/learningleadershow/id/38227820
info_outline
653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders
09/14/2025
653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Sukhinder Singh Cassidy is the CEO of Xero. Xero is a cloud-based accounting software designed for small businesses. They did $2.1 billion in revenue last year. Over the past 25 years, Sukhinder has had leadership roles at Google, Amazon, and StubHub. Notes: Key Learnings Strategic CEO Job Search Criteria – Sukhinder had four non-negotiables: macro tailwinds/good market, customer she could be passionate about, strong business model, and a role where she could "learn for miles" for 5-8 years. Only two companies met her criteria in 18 months of searching. "Sell, Interview, Sell" Hiring Process – First meeting is 50% selling the opportunity to attract top talent. Only after candidates lean in do you shift to intensive interviewing with leadership team exposure. The Virtuous Cycle Framework – Customer at the top, supported by "high purpose, high performance, high people" culture. "It's an 'and,' not an 'or'" - you don't get to choose just one element. Back-Channeling is Critical – Reference checking happens throughout the entire interview process, not just at the end. "The most important thing is not just front channel... it's all the back channel." Values Alignment Over Pure Qualifications – "Go where my values fit and my strengths are valued." Cultural fit becomes the deciding factor in close hiring calls, not competence. The Layoff Leadership Test – Six weeks after joining, Sukhinder laid off 900 people based on McKinsey benchmarking. Showed consistency between the outside-in analysis presented to the board and transparent communication to employees. Portfolio of Bets Strategy – Balance growth, profitability, and customer happiness through diversified initiatives ranging from "safe moves" to "flyers," with clear probability assessments. Consistency as Culture Foundation – "Culture means consistency of message and what's important." Authenticity through change, not resistance to change. The 10-Slide CEO Interview Deck Framework: Vision statement (destination in 2-3 years) Outside-in market analysis Competitive landscape SWOT analysis of current position Five key strategic moves Implementation approach ("the how") Estimated outcomes with probability ranges Practical Application: Job Search Strategy – Define 4-5 non-negotiable criteria upfront. Be willing to wait for roles that truly meet your standards rather than taking "the job before the job." Interview Preparation – Always build a comprehensive thesis deck even if not requested. Use it to clarify your own thinking and demonstrate strategic capability. Hiring Excellence – Spend equal time selling the opportunity and evaluating candidates. Use diverse interview panels and back-channel extensively throughout the process. Cultural Leadership – Be consistent in messaging across all stakeholders (board, investors, employees). Authenticity enables trust during periods of change. Strategic Planning – Frame initiatives as a portfolio of bets with clear probability assessments. Balance growth, profitability, and customer satisfaction rather than optimizing for one. Leadership Hiring Process: The CEO interviews top 2-3 levels even without hiring authority Diverse interviewer panels with "bar raisers" Business problem-solving presentations in the final rounds Multiple leadership team interactions before the final decision Life Lessons: Patience in Career Progression – Sometimes the right opportunity requires waiting. Sukhinder was frustrated during 18 months of searching but found the perfect fit. Preparation Separates Candidates – The depth of strategic thinking demonstrated in final presentations often determines CEO selections. Culture Survives Through Consistency – Not avoiding change, but maintaining consistent values and communication approach through inevitable changes. Leadership Requires Tough Decisions – Laying off 900 people six weeks into the role, but doing it transparently and based on clear data/analysis. Value Creation Through Alignment – Finding roles where your strengths are valued and values align creates exponentially better outcomes than pure skill matching. Systems Thinking Builds Trust – Sharing appropriate "behind the scenes" context helps teams understand difficult decisions and builds long-term credibility. Early Career Focus – "Do great work for great people." Find talented leaders to apprentice under and work exceptionally hard to maximize learning. Authenticity Enables Performance – Being genuine about challenges and changes builds stronger relationships than trying to maintain artificial stability. Strategic Communication – Frame personal asks in terms of organizational benefits. Make it about solving their problems, not your desires. The Xero Transformation: Financial Performance: $2.1B revenue, 21% YoY growth while maintaining profitability Cultural Approach: "High purpose, high performance, high people" - no choosing between them Strategic Moves: Pricing/packaging optimization, sales motion transformation, customer experience reimagining (new dashboard with 3000+ customer inputs) Leadership Philosophy: Provide a "systems view" to employees, share investor-level insights appropriately, and maintain authenticity during difficult decisions
/episode/index/show/learningleadershow/id/38142610
info_outline
652: Arthur Brooks - The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy
09/07/2025
652: Arthur Brooks - The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy
Apply to be in my next Learning Leader Circle - This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Notes: Key Learnings The Mad Scientist Emotional Profile – High achievers typically have both high positive and high negative affect. "Hustlers, hard workers, strivers, entrepreneurs, ambitious people, they're in that quadrant of high positive, high negative affect." This creates intensity but requires management of negative emotions. Dangerous Negative Affect Management – People try to manage high negative affect through alcohol, excessive internet use/pornography, and workaholism. "The isms, the addictions, they're almost all negative affect management techniques." Two Best Ways to Manage Negative Affect: Faith, Spirituality, Philosophy - "Every day, go deep" into transcendent practices Physical Exercise - "Go pick up heavy things" - resistance training moderates negative emotions Arthur's 4:30 AM Protocol – Wakes at 4:30, works out 4:45-5:45, attends mass 6:30-7:00, then has high-protein breakfast with dark coffee at 7:45 for 4 hours of peak creative focus. "I get four hours of creative concentration with maximum dopamine." Exercise Reduces Unhappiness, Doesn't Create Happiness – "Working out hard... moderates negative affect. It makes you less unhappy" rather than directly increasing positive emotions. The Failure Journal Method – Write down failures/disappointments, return after 3 weeks to note learnings, return after 2 more months to identify good things that resulted. This installs learning in the prefrontal cortex rather than letting it "float around limbically." Early Success Can Be Dangerous – Scholars rejected for early research grants outperformed those with early success. "Much better is when you do the work and build yourself up... be a wholesaler before you become a retailer." Management Doesn't Provide Flow – "There's one kind of job where you don't get flow, and that's management... you're getting jerked from thing to thing to thing." Being CEO was "satisfying, but not enjoyable." Intelligence Must Serve Others – "Intelligence is just another gift... whether or not it makes you happier depends on whether or not you're using it to make other people happier." Denigrating others for lower intelligence indicates misusing your gift. The Arrival Fallacy – Olympic gold medalists often experience depression after winning because positive emotion comes from progress toward goals, not achieving them. "Your positive emotion doesn't exist to give you a permanent good day." Two Midlife Crisis Solutions: Focus on what age gives you rather than takes away Choose subtraction over addition - appreciate what you no longer have to do Making Changes Stick Requires Three Elements: Understand the science - Know why something works Change your habits - Actually implement different behaviors Teach it - Explain it to others to cement learning in the prefrontal cortex The Happiness Formula – "Use things, love people, worship the divine" instead of the natural impulses to "love things, use people, and worship yourself." Multi-generational Living Benefits – Arthur lives with adult children and grandchildren: "The research is clear that the closer you are to your grandchildren... the better it is for everybody." Quotes: "I get four hours of creative concentration with maximum dopamine in my prefrontal cortex... ordinarily I would get an hour and a half, two hours of real clarity." "The isms, the addictions, they're almost all negative affect management techniques." "Working out hard... makes you less unhappy. The research is very clear." "Being the boss isn't that fun. It just isn't." "I have carefully accounted for all of my days of happiness. They add up to 14." (Emir of Cordoba) "What's first prize in a pie eating contest? The answer is pie. So I hope you like pie." "Beware the corner office boys. Beware the corner office." "Use things, love people, worship the divine." "Watch one, do one, teach one." (Harvard Medical School) "Don't trust your impulses. Your impulses are to love things, use people, and worship yourself." Life Lessons Develop Daily Discipline Early - A Consistent morning routine with exercise and spiritual practice creates optimal brain chemistry for peak performance throughout the day. Manage High Achievement Personality - If you're a driven person, recognize you likely have high negative affect that needs healthy management through exercise and transcendent practices. Reframe Career Setbacks - Early failures often build stronger foundations than early successes. Use disappointments as learning opportunities through systematic reflection. Question Management Ambitions - Consider whether you enjoy management or just want the status/money. Management roles inherently provide less flow and enjoyment. Use Intelligence to Serve Others - Your cognitive gifts should lift others up, not put them down. Intelligence without service leads to unhappiness. Focus on Progress, Not Arrival - Derive satisfaction from forward momentum in meaningful work rather than achieving specific goals that won't provide lasting happiness. Embrace What Age Gives - In life transitions, focus on new capabilities and freedoms rather than what you're losing or leaving behind. Teach What You Learn - The most effective way to cement new habits and insights is to explain them to others. Teaching accelerates your own learning. Choose Subtraction - Happiness often comes from eliminating negative elements (bad meetings, toxic relationships) rather than adding more positive ones. Build Multi-Generational Relationships - Prioritize time with family across generations. The research strongly supports benefits for all parties. Exercise for Mental Health - View physical training as medication for negative emotions rather than just physical fitness. Cultivate Transcendent Practices - Whether religious, philosophical, or spiritual, daily engagement with something larger than yourself moderates negative emotions and provides meaning. Time Stamps: 00:10 Arthur's Fitness and Health Routine 02:01 Link Between Fitness and Happiness 04:03 Managing Negative Emotions 06:23 Morning Routines 13:24 The Importance of Failure 22:26 The Reality of Promotions and Leadership 27:56 The Power of Intelligence: A Double-Edged Sword 28:28 Using Gifts to Spread Happiness 29:20 The Impact of Helping Others 33:28 Avoiding the Arrival Fallacy 36:36 Redefining Retirement and Midlife 47:39 The Importance of Teaching and Learning 51:28 Life Advice 53:01 EOPC (End of the Podcast Club)
/episode/index/show/learningleadershow/id/38056375
info_outline
651: Shaka Senghor - From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free)
08/31/2025
651: Shaka Senghor - From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free)
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Shaka Sengor spent 19 years in prison for killing a man. He’s transformed his life through not making excuses and taking full ownership of his decisions. Now, he’s a New York Times best-selling author who has been called a “soul igniter” by Oprah. His latest book is called How to Be Free. Notes: The Permanence of Split-Second Decisions – At 17, shot three times on a Detroit corner. At 19, he killed a man in a conflict after creating a narrative that he would "shoot first." Sentenced to 17-40 years for second-degree murder. "I try to teach young people about understanding the permanence of a 30-second decision." Books as Portals to Freedom – Read over 1,500 books during 19-year incarceration, starting with street literature (Pimp, Black Gangster) as a gateway to philosophy (Plato, Marcus Aurelius). "Books allowed me to escape in the most literal sense... a portal into other worlds." Prison Mentors Changed Everything – Lifers became his guides: "These are men serving life sentences who came equipped with wisdom about what's on the other side... they guided me to books that shattered old narratives and opened possibilities." Reading Creates Writing Excellence – Speed-reading skill from age 8 (learned during punishments with encyclopedias) combined with voracious prison reading, led to becoming a NY Times bestselling author. "You have to be a practitioner of the craft every day." Journaling as Transformation Tool – "It was the most healing experience I've ever had to speak to my truth, speak to the pain points." Uses 20 different journals, writes everywhere - planes, shower thoughts on phone, margins of books. Hidden Prisons We All Carry – "The most powerful prisons aren't the ones made of concrete and steel. They're the ones we carry with us, built from grief, anger, shame, trauma." Everyone has internal prisons that can be opened. Vulnerability as Strength, Not Manipulation – Authentic vulnerability vs. weaponized oversharing. "Human beings have this innate ability to suss out the truth. Authenticity and vulnerability is the super unlock... being true to your center." Community Through Shared Truth – Prison taught extreme friendship criteria: "Are they willing to serve a life sentence for you or die for you?" Now applies accountability standards: showing up consistently, being loyal to family first. Violence Born from Fear – "Reactionary violence is typically born out of fear, being afraid." Prison taught him to see "the child in people" who are acting out, leading to empathy instead of escalation. Voluntary Hardship Builds Resilience – Monthly 3-day fasts in solitary confinement prepared him for food deprivation punishment. "None of us get through life without suffering... that extra hour a week can change your life's outcomes." Composure Through Self-Awareness – Developed through journaling about times he wasn't composed. "Once you've written it down, you own it. When you own it, you can control it. When you can control it, it's easy to become composed." Remove All Excuses – Florence Nightingale quote: "I never gave or took any excuse." Despite a felony record, a violent crime conviction, and 20 years in prison, he chose to "lead a great life" by removing every excuse. The Ben Horowitz Friendship – Unlikely brotherhood with VC billionaire, starting from Oprah's introduction, bonding over music and culture until 3 AM conversations. Shows authentic relationships transcend backgrounds. Quotes: "I try to teach young people about understanding the permanence of a 30-second decision." "I was in prison before I stepped foot in a cell, and I was free before they ever let me out." "The most powerful prisons aren't the ones made of concrete and steel. They're the ones we carry with us." "Books allowed me to escape... a portal into other worlds." "Once you've written it down, you own it. When you own it, you can control it." "I never gave or took any excuse." (Florence Nightingale) "Master your thinking, master your destiny." "Violence is typically born out of fear, being afraid." "If you can see the child in the person that's acting out... it equips you to have more empathy." "None of us gets through life without suffering. At some point, we're all gonna go through adversity." "I chose to lead a great life... I removed every excuse." Life Lessons: Face Your Internal Prisons – Identify the shame, anger, grief, and trauma that create mental prisons. Recognize that these have doors that can be opened through conscious work Use Reading as Escape and Growth – Books provide mental freedom regardless of physical circumstances. Start with what interests you, then expand to broader learning. Practice Voluntary Hardship – Choose difficult challenges (fasting, extra work, taking stairs) to build resilience for inevitable adversity you don't choose. Journal for Self-Awareness – Write down thoughts, patterns, and reactions to own and control them. Use various methods - handwritten, voice memos, and margins of books. Build Authentic Community – Surround yourself with people who will hold you accountable and tell you the truth. Apply the highest standards to friendship selection. Transform Fear into Empathy – When facing conflict, look for the "child" in the other person. Understanding their fear reduces your reactionary responses. Develop Composure Through Practice – Review past moments of losing control to build awareness. Use this knowledge to respond rather than react in future situations. Remove All Excuses – Whatever your circumstances, choose to pursue greatness rather than accepting limitations. The past doesn't define the future unless you let it. Share Your Truth Vulnerably – Authentic storytelling about pain and growth helps others escape their own prisons. Vulnerability is strength when used to serve others. Create Evidence of Resilience – Completing self-imposed challenges builds confidence for handling external adversities. Each victory creates proof you can handle hard things. Choose Your Narrative – You can change the story handed down to you. Reject limiting beliefs about what's possible based on background or circumstances. Apply to be part of my
/episode/index/show/learningleadershow/id/37946230
info_outline
650: Michelle "Mace" Curran - Building a World-Class Team, Running an Excellent Debrief, Rebuilding Trust, Feedback Loops, & How To Turn Fear Into Your Superpower
08/24/2025
650: Michelle "Mace" Curran - Building a World-Class Team, Running an Excellent Debrief, Rebuilding Trust, Feedback Loops, & How To Turn Fear Into Your Superpower
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. My guest: Michelle “Mace” Curran is a combat veteran, former fighter pilot, and only the second woman in history to fly as the Lead Solo for the Thunderbirds, the U.S. Air Force’s elite demonstration squadron. Now on a new mission, she’s using her story to inspire others. She is the best-selling author of The Flipside: How to Invert Your Perspective and Turn Fear Into Your Superpower. How to run "debrief" so that giving and getting feedback becomes embedded in your culture. The biggest mistake Michelle made when she became a new fighter pilot, and what you can learn from it. Early Exposure to Male-Dominated Environments – Michelle's dad took her hunting with guys starting at age 7, teaching her she "belonged in any room" she wanted to pursue. This early experience prepared her for being 1 of only 2% female fighter pilots. Parents Who Believed in Wild Dreams – Parents worked multiple jobs to afford camps (criminal justice, archaeology) whenever Michelle showed interest in something new. Taught her that opportunities weren't just possibilities - "I could go after it." The Lone Wolf Trap – When struggling in her first squadron, Michelle was afraid to ask questions because she thought it would show she didn't belong. "I wouldn't even ask questions because I felt like asking a question was just so uncomfortable." Three Years of Struggling in Silence – Despite performing well in the air, Michelle spent three years "belly crawling, pulling myself by my fingernails" because she felt pressure to represent all women perfectly. The Fresh Start Power – Moving from Japan to Texas gave her a reset: "No one here knows about my divorce. No one here knows all these struggles I've been going through." Sometimes you need a clean slate to rebuild. Curiosity + Vulnerability = Community – The breakthrough came when fellow pilots asked pointed questions beyond platitudes: "How are you actually doing?" Real curiosity that goes deeper than "let me know if you need anything." The Near Head-On Collision Story – Flying inverted at 500 mph, passing within 80 feet of another jet using only eyeballs for distance measurement. When her student pilot aimed straight at her, she had 2.5 seconds to decide whether to move or hold position. Learning from Mistakes, Not Punishing Them – After the near-collision, Michelle chose teaching over berating: "What is the most productive way we can respond to get the most learning from that?" The student learned faster because he found the boundary. The Debrief Culture Framework – Start with objectives, go through segments systematically, ask "why" five times to find root causes, create specific lesson learned, and share with the entire organization so others don't repeat mistakes. Rank Comes Off in Debriefs – Even generals sit in debriefs led by mid-level captains who are the real tactical experts. "Status comes off" - expertise matters more than hierarchy when analyzing performance. The Teaching-Learning Loop – Moving from student (year 1) to instructor (year 2) creates exponential learning: "Your students will teach you more than you probably learned when you were a student." Time Distortion Under Extreme Stress – During the near-collision, Michelle experienced "the craziest temporal distortion" where "time slows down" but "you can't do anything faster than you normally can." Build Competence First, Then Serve Others – Advice for young people: Spend 6-8 years building skills and confidence, then "reach a hand back" to mentor others. Both phases are essential for maximum impact. Quotes: "They endlessly believed in every wild dream I set my sights on." "I learned my vocabulary of profanity expanded greatly... but I also learned I could hang in that environment." "I went into it naively thinking that it didn't matter at all... and it's a little bit different as you get into the military." "There's no fear when you're present. Fear is a future thing." "Curiosity plus vulnerability equals community." "What is the most productive way we can respond at this point to get the most learning from that?" "More learning happens in the debrief than actually does during the flight itself." "The egos that people see in Hollywood around fighter pilots... what they don't show is the humility that has to happen behind the scenes." "It's not self-centered to spend that first six to eight years focused on learning and honing skills." "You get to reach a hand back... and it becomes one of the most fulfilling things for you as well." Life Lessons: Expose Children to Challenging Environments Early – Like Michelle's hunting trips, give kids experience in situations where they're the minority or outsider to build confidence. Support Wild Dreams with Action – Don't just say you believe in someone's goals - invest time and money in giving them exposure to those fields. Ask for Help Before You're Drowning – The biggest mistake is thinking asking questions shows weakness. Everyone expects beginners to have questions. Create Psychological Safety for Mistakes – Focus on learning from errors rather than punishing them. The response to mistakes determines future trust and performance. Build Debrief Culture in Your Organization – Set clear objectives, analyze systematically, find root causes, create specific action items, and share lessons broadly. Use Fresh Starts Strategically – Sometimes changing environments gives you the reset needed to implement new behaviors and shed old baggage. Go Beyond Surface-Level Check-ins – Real community comes from curiosity that goes deeper than "how are you?" Be willing to ask uncomfortable follow-up questions. Practice Temporal Awareness Under Stress – In high-stakes situations, your brain may speed up while time seems to slow down. Prepare for this distortion through practice. Separate Expertise from Hierarchy – The most knowledgeable person should lead analysis sessions, regardless of their position in the org chart. Balance Self-Development with Service – Early career should focus on building competence; mid-career should emphasize mentoring others. Accept That High Performance Requires High Standards – Like the Thunderbirds' 70-foot separation at 500 mph, excellence often means operating with minimal margin for error. Apply to be part of my
/episode/index/show/learningleadershow/id/37880725
info_outline
649: Sam Lessin - Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin's Lessons)
08/17/2025
649: Sam Lessin - Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin's Lessons)
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. My guest: Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. His career highlights include serving as a key executive at Facebook, leading product management efforts, and successfully co-founding Fin. His current role at Slow Ventures involves investing in innovative startups across various sectors, showcasing his expertise in entrepreneurship and venture capital. Notes: Key Learnings The 4:30 AM Advantage – Sam's father would be at his desk by 4:30 AM every day, saying, "It's easy to look smart if you have a several-hour head start on everyone else." Early work creates compounding advantages over time. Either Be Early or Be Late, Don't Be On Time – Father's wisdom about timing and seasons. Start your career super early to get ahead, or strategically wait and come in later. Timing matters more than perfect preparation. Joy as the Ultimate Competitive Advantage – "I just don't think that in the long run, angry people win." Look for joyful people in hiring and partnerships because joy is sustainable while anger burns out. Type Two Fun Builds Resilience – Type 1 fun is enjoyable while doing it (rollercoaster). Type 2 fun "completely sucks while you're doing it, but there's joy on the other side" (climbing mountains, marathons). Entrepreneurs need Type 2 fun experiences. Practice Voluntary Hardship – Sam ran a sub-3-hour marathon and got a pilot's license not for love of activities, but for "practice moments" of perseverance. Creates evidence that you can handle business adversity. Right Person, Right Opportunity, Right Time – Don't ask "is this a great person?" Ask, "Is it the right person at the right moment?" Success requires all three elements to align, not just talent. Write Publicly for Intellectual Receipts – "If you can't write the check, write me the thesis and timestamp it." Writing creates accountability, proves thinking ability, and builds reputation over time. Nobody Knows What They're Doing – Working at Bain taught Sam that even prestigious companies "have no idea what you're doing." This is liberating—you can figure it out too. Big Things Take Time (Slow Ventures Philosophy) – Most success isn't quick wins. Venmo took "so many turns of the crank." Be patient finding the right wind, then sail fast when you catch it. Embrace Being Wrong Most of the Time – Seed investing means "you're mostly wrong, you mostly lose money." Success comes from being very right occasionally, not being right consistently. The Solana 2000x Return Story – Put in $400K, returned 2000x to LPs. Success came from the intersection of thesis (looking for "Ethereum killer") and relationships (following Raj Gokal through multiple startups). Use Humor and Authenticity as Filters – Slow Ventures website looks like a law firm in tuxedos "on purpose." If you don't think it's funny, "you're not who we want to invest in." Writing Pushes Away Wrong People – "I really like to be not liked by the people I don't want to work with." Authentic writing attracts the right people and repels the wrong ones. Manufacturing Hardship for Privileged Kids – "Tiger Dad" sports culture might be a misguided attempt to create necessary adversity for wealthy children who lack natural hardships. I loved the throughline of this whole conversation being about his dad, working exceptionally hard, and having joy and excitement for the journey. Maybe it was the near-death experiences that his dad had that led to that mindset. Regardless, it’s something we can all learn from. We want to be around optimistic people who have joy and love for what they’re doing… Nobody knows what they’re doing. We’re all figuring it out as we go. You’ll never learn unless you go out and do the thing. Figure it out as you go. Just get started. And iterate. Learn. Try again. And keep going. Advice from Sam – Write publicly. You don’t know what you think until you get your thoughts out of your head onto the page. And if you publish them, you have a record of the journey. Also, you might attract someone to work with. That is how Jack Raines (guest on episode #539) caught Sam’s attention, and now they work together. Useful Quotes: "It's easy to look smart if you have a several-hour head start on everyone else." "I just don't think that in the long run, angry people win." "Either be early or be late, don't be on time." "The right question is, is it the right person at the right moment?" "Writing is thinking. If you can't write, you can't think." "I feel like a tenured professor of capitalism—responsible to make a lot of money over the long term by being very right every once in a while with permission to be wrong all the time." "One of the most insulting things you can call someone is a market participant." "The beauty of the internet is so big. The right people find you." "Big things take time." "Life's short. Is this really what you're spending your time on?" . Time Stamps: 00:11 Sam’s Dad's Unique Career Path 00:39 Life Lessons from My Dad 04:35 The Trade-offs of Hard Work 06:57 Betting on the Right People 07:23 The Importance of Joy in Success 10:39 Overcoming Hardships and Building Resilience 20:40 My Journey: From Harvard to Bain 26:06 Joining Facebook and Learning from Mark Zuckerberg 29:36 Balancing Joy and Competitive Spirit 30:15 The Story of Rippling and Parker 31:48 The Solana Investment Journey 34:33 The Importance of Writing and Public Thought 41:07 The Philosophy Behind Slow Ventures 52:54 Advice for Aspiring Venture Capitalists 55:46 Future Plans
/episode/index/show/learningleadershow/id/37765405
info_outline
648: Ed Latimore - Going From Zero to One, Taking Ownership, Positive Body Language, Strategic Hardship, & Hard Earned Lessons From The Hurt Business
08/10/2025
648: Ed Latimore - Going From Zero to One, Taking Ownership, Positive Body Language, Strategic Hardship, & Hard Earned Lessons From The Hurt Business
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. My Guest: Ed Latimore is a professional heavyweight boxer, best-selling author, and veteran of the U.S. Army National Guard. He earned a degree in Physics from Duquesne University. Ed has gained recognition for overcoming personal struggles with addiction and poverty. We recorded this at our 2025 Learning Leader Growth Summit in Scottsdale, Arizona. He's the author of Hard Lessons From The Hurt Business. Notes: Key Learnings The Heaviest Weight at the Gym is the Front Door – Starting is often the hardest part. "Zero to one is the hardest part" in any endeavor. Once you begin, momentum builds, but that first step requires the most effort. How You Feel is Irrelevant – "How you feel about doing something is irrelevant. If it is vital to your success, you've gotta bump to the wall a bunch of times." Discipline isn't about motivation—it's about doing what's necessary regardless of feelings. Sobriety: The Hardest Fight – 13+ years sober, describing it as "the hardest fight I've ever had." The turning point came during basic training when he built an identity completely free of alcohol for the first time in his adult life. From Being Liked to Being Respected – "When people like you, they want to party with you... When people respect you, you start getting invited back to family events." Shifted focus from seeking approval through partying to earning respect through character. The Baby Shower Revelation – Breakthrough moment when friends showed up with gifts for his unborn child, "all because he is my human." Realized people genuinely cared about him, which became the foundation for believing he mattered. Taking Ownership vs. Playing Victim – "A judge and a jury do not care about my terrible upbringing if I commit a crime." Despite growing up next to a crack house with family addiction issues, I chose accountability over excuses. Net Positive Impact Philosophy – Goal with raising children: "Make sure they are a net positive, they make things better. At the very least, let's make sure they don't mess anything up." Everyone has an impact on the world for better or worse. Practice Until You Can't Forget – Boxing taught the overlearning principle: going beyond basic competency to automatic response. "We practice until we can't forget... Either you get it or you'll make a mistake, and you probably won't make the mistake more than twice." Tolerance for Boredom Builds Excellence – "If you can be bored, you can go really far because a lot of it is just repetition of really basic things." Elite performers master fundamentals through unglamorous repetition. Body Language Shapes Internal State – "You smile, you feel happy... puff up your chest and the testosterone flows." Physical presentation affects how you feel internally and influences others around you. Fear vs. Responsibility Evolution – Early motivation came from fear of embarrassment; current motivation comes from a sense of responsibility to others. Shift from avoiding personal failure to ensuring others are taken care of. Redefining "At Your Best" – Past definition: having enough money, time, and no worries. Current definition: "Everyone in the house is taken care of." Evolution from internal satisfaction to external impact. Strategic Hardship Introduction – For teaching children without trauma: "Introduce hardships strategically and with awareness." Like weight training—incremental challenges build strength; too much too soon causes injury. Useful Quotes: "How you feel about doing something is irrelevant. If it is vital to your success, you've gotta bump to the wall a bunch of times." "The heaviest weight at the gym is the front door." "When people like you, they want to party with you... When people respect you, you start getting invited back to family events." "You have an impact on the world, for better or worse, that makes a huge difference in allowing a person to not destroy themselves." "We practice until we can't forget." "If you can be bored, you can go really far." "I've had my ego dragged through the mud a lot." "What do you want your obituary to say? I didn't just dabble." "When you're completely selfless, then you're fearless. It's the 'what's gonna happen to me' that creates the fear." "Everyone's always either walking in love or fear." "I hope my kid remembers that I was a present happy dude." Life Lessons: Discipline Over Mood – Make decisions based on necessity, not feelings. Success comes from identifying what must be done and executing consistently. Identity Building Without Vices – Spend time in environments completely free from your struggles to build new neural pathways and self-concept. Overlearning for Mastery – Practice skills beyond basic competency until they become automatic responses under pressure. Authentic Accountability – Find mentors who "live what they're yelling at you about." Real influence comes from demonstrated behavior, not just words. Incremental Challenge Builds Resilience – Introduce difficulties gradually to build strength rather than overwhelming with too much too soon. Present Moment Parenting – Model calm behavior during stressful situations because children mirror your emotional energy. External Focus Creates Fulfillment – Shift from personal satisfaction to ensuring others are taken care of for a deeper sense of purpose. Childhood Dreams Reveal True Interests – "What did you want to do when you were 10-12?" Often reveals authentic passions before social conditioning. Breaking Generational Cycles – Consciously choose different patterns than your upbringing to create better outcomes for the next generation. Humility Through Struggle – Getting "ego dragged through the mud" builds character and perspective that success alone cannot provide. Luck Recognition Builds Gratitude – "The only difference between you and me is that I was lucky." Understanding the role of circumstances builds empathy. .
/episode/index/show/learningleadershow/id/37624830
info_outline
647: Tim Ferriss - Chasing Your Curiosity, Internal vs External Scoreboards, Effectiveness over Efficiency, Winning Even if You Fail, Fame's Hidden Costs, & The Mount Rushmore of Podcasting
08/03/2025
647: Tim Ferriss - Chasing Your Curiosity, Internal vs External Scoreboards, Effectiveness over Efficiency, Winning Even if You Fail, Fame's Hidden Costs, & The Mount Rushmore of Podcasting
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. My Guest: Tim Ferriss is the author of five #1 New York Times bestsellers (including The 4-Hour Work Week, Tools of Titans, and Tribe of Mentors). His podcast, The Tim Ferriss Show, has been listened to more than a billion times. Tim was an early investor in Uber, Shopify, Twitter, Alibaba, and many others. He’s the creator of a new card game called COYOTE. Decision making - How can I win even if I lose? He viewed angel investing like his personal MBA. Instead of paying for business school, he invested in companies and learned about business by working with actual businesses. He didn’t expect to make money on those investments. That was just a bonus. Think, “How can I win even if I lose?” Tim won with those investments, regardless of whether he made money or not on them. Key Takeaways and Learnings: Parents Who Foster Curiosity – Tim's mother created a "books are always in budget" policy despite tight finances. Used remainder tables at bookstores to expose him to random, off-menu knowledge that sparked lifelong curiosity about unconventional topics. Curiosity-Driven Exploration – When Tim showed interest in marine biology, his mom found Frank Mundus (inspiration for Jaws character), arranged a meeting, and created low-cost adventures like crab fishing with chicken bones to fuel his interests. The Mask You Wear Becomes You – "Be very careful what you pretend to be" - spent years presenting as overly serious to be taken seriously, which created a recursive feedback loop. Now embraces more play and laughter to avoid burnout. Fiction and Poetry as Life Teachers – Shifted from non-fiction purist to reading more fiction/poetry. Recommends "Ozymandias" as a monthly reminder that all achievements fade: "My name is Ozymandias, king of kings. Look on my works, ye mighty and despair. Nothing beside remains." Internal vs External Scorecards – Money and fame amplify whatever's underneath, like alcohol or power. "If you have certain insecurities or paranoia, all of those are going to be amplified. If you're generous, that's also gonna be the case." Effectiveness Over Efficiency – "Effectiveness is doing the right things, efficiency is doing things well, but doing something well does not make it important." Focus on choosing the right targets rather than optimizing everything. Strategic Slack in Systems – Moved away from filling every 10 minutes. Takes 10 minutes each morning with coffee to read fiction/poetry/meditate to prove "you do not have to front flip out of bed and land in a full sprint." How to Win Even If You Fail – Project selection framework: "How can I win even if I fail?" Focus on relationships built and skills acquired that transfer beyond the project if external metrics don't pan out. The COYOTE Game Philosophy – Created a card game to address the social isolation epidemic. "People don't have a shortage of productivity advice... It's taking some steam out of the system and actually enjoying what you have worked so hard for." Social Bonds as Foundation – "It's the relationships, stupid." Countries rated happiest fundamentally come down to social ties. In-person social interactions are down 70% in certain age groups over the last 10 years. Podcasting as Relationship Building – "My goal is not to have 100% of my audience like any episode... but I do want 10% of my audience to love each episode." The personal is the most universal. Fame's Hidden Costs – With the audience size of major cities comes proportional number of unstable people. "If you have a small village, you're gonna have one village idiot... "How many crazy people are there in New York City?" "Be suspicious of what you want." Tim read me the poem by Ozymandias by Percy Bysshe Shelley "If more information were the answer, we'd all be billionaires with six-pack abs." Be a talent scout - You don’t need a huge network. A+ players in one area know A+ players in others. Seek out people who are great at what they do, regardless of what they do. Study what makes them great at that thing. Then you’ll probably meet other A+ players. Also, it’s on us to strive to be an A+ player at what we do. Be so good at whatever your thing is that other A+ players want to meet you. Tim has been very good at that. Quotes: "Be very careful what you pretend to be... the mask you wear often becomes the person you are." "Be suspicious of what you want." (Rumi) "My name is Ozymandias, king of kings. Look on my works, ye mighty and despair. Nothing beside remains." "Effectiveness is doing the right things, efficiency is doing things well, but doing something well does not make it important." "How can I win even if I fail?" "The personal is the most universal." "It's the relationships, stupid." "If more information were the answer, then we'd all be billionaires with six-pack abs." "Follow your curiosity and obsessions with great rigor. Do that and I like your chances." "The superheroes you have in your mind are nearly all walking flaws who've maximized one or two strengths." "You don't need a huge network... the super A+ players tend to know other A+ players." Life Lessons: Cultivate Childhood Curiosity – Create "always yes" policies for learning and exploration. Use constraints (like remainder tables) to discover unexpected interests. Embrace Strategic Experimentation – View life as a series of 6-12-month projects with 2-4 week experiments. Design studies to get feedback, not just chase outcomes. Balance Seriousness with Play – Taking yourself too seriously leads to burnout. Build in recovery phases and "deloading" periods across all life areas. Choose Projects for Learning – Select opportunities based on relationships you'll build and skills you'll acquire, not just potential external rewards. Start With Personal Pain Points – Best opportunities often come from solving problems you personally understand deeply, then expanding adjacent. Build Safety Nets First – Like Arnold's real estate, before acting, create financial/emotional cushions that allow you to say no and wait for right opportunities. Quality Over Quantity in Relationships – Better to have deep connections with fewer people than surface-level networks with many. Morning Rituals Create Calm – Prove to your nervous system you don't have to be frantic by taking 10 minutes each morning for something peaceful. Scratch Your Own Itch – Whether in podcasting, investing, or any pursuit, follow genuine personal interest for sustainable energy and authentic results. Prepare for Success Taxes – Fame and wealth amplify existing traits. Address insecurities and develop strong boundaries before scaling. Value Present Experience – Focus on daily energy in/out rather than constantly deferring happiness to future achievements. . Time Stamps 00:38 Tim's Childhood and Parental Influence 01:15 Curiosity and Lifelong Learning 02:56 Marine Biology and Childhood Adventures 07:06 Influence of Mentors and Teaching Aspirations 08:45 Thoughts on Parenthood and Relationships 12:11 Balancing Seriousness and Humor 25:15 Effectiveness vs. Efficiency 30:50 Creating Slack and Self-Care 34:41 The Importance of Social Bonds and Play 41:07 Meeting a Game-Changing Partner 42:13 The Importance of Analog Social Interaction 42:55 Podcasting: A Platform for Deep Connections 43:30 The Evolution and Challenges of Podcasting 43:47 The Art of Interviewing 49:18 Navigating Fame and Public Exposure 01:04:26 The Philosophy of Risk and Experimentation 01:10:27 Spotting Talent and Following Curiosity 01:20:37 Closing Thoughts and Future Endeavors
/episode/index/show/learningleadershow/id/37610830
info_outline
646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder)
07/27/2025
646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder)
Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Guest: Nick Maggiulli is the Chief Operating Officer and Data Scientist at Ritholtz Wealth Management. He is the best-selling author of Just Keep Buying: Proven Ways to Save Money and Build Your Wealth, and his latest book is called The Wealth Ladder. Nick is also the author of OfDollarsAndData.com, a blog focused on the intersection of data and personal finance. Notes: Money works as an enhancer, not a solution: Like salt enhances food flavors, money amplifies existing life experiences but has little value by itself without relationships, health, and purpose. "Money by itself is useless... without friends, family, without your health, it doesn't add much... it enhances all the other parts of life." Nick beat his dad’s friends at chess when he was 5 years old because he practiced more than they did. He got more reps. He did the work. It’s not that he was a chess prodigy. He just worked harder than his opponents did. And he still does that today. Practice creates expertise beyond intelligence: At five years old, Maggiulli could beat adults at chess not because he was smarter, but because he had more practice. Consistent effort over time can outcompete raw talent. "I could beat them, not because I was smarter than them, only because I had practiced something... In this very specific realm, I could beat them." Consistent writing builds compound advantages: Writing 10 hours every weekend for nine years created opportunities including book deals and career advancement. The discipline of regular practice compounds over time. "I've been writing for nine years... I spend 10 hours a week every single week for almost a decade now, and that helps over time." The most expensive thing people own is their ego. How do you add value when you're in a job that doesn't have a clear scoreboard (like sales)? Think... What gets accomplished that otherwise wouldn't have without you? Add value through time savings and efficiency: In roles where impact isn't immediately measurable, focus on how much time and effort you save others. Create systems that make your colleagues more efficient. "How do I save our operations team time? How do I save our compliance team time... I'm designing better oars that'll give us 10% more efficiency." Money amplifies existing happiness: Research shows that if you're already happy, more money will make you happier. But if you're unhappy and not poor, more money won't solve your problems. "If you're happy already, more money will make you happier... but if you aren't poor and you aren't happy, more money's not gonna do a thing." Ego is the most expensive thing people own: Trying to appear wealthier than you are prevents actual wealth building. Focus on substance over status symbols. "People in level three that wanna look like people in level four end up spending so much money to keep up with the Joneses." Follow your interests for long-term success: Passion sustains you through inevitable obstacles and rejection. Maggiulli wrote for three years without earning money because he genuinely enjoyed it. "Follow your interest because when you follow your interest, you're more likely to keep going when you face obstacles." The "Die with Zero" philosophy, advocated by Bill Perkins, encourages people to prioritize experiences and fulfillment over accumulating maximum wealth, suggesting spending money strategically to maximize lifetime enjoyment. Nick defines six levels of wealth based on net worth, ranging from $0 to over $100 million. These levels are: Level 1: $0-$10,000 (paycheck-to-paycheck), Level 2: $10,000-$100,000 (grocery freedom), Level 3: $100,000-$1 million (restaurant freedom), Level 4: $1 million-$10 million (travel freedom), Level 5: $10 million-$100 million (house freedom), and Level 6: $100 million+ (philanthropic freedom). Nick also notes a shift in asset allocation as one progresses through the levels. In the lower levels, a larger portion of wealth is tied up in non-income-producing assets like cars, while higher levels see a greater emphasis on income-producing assets like stocks and real estate. Wealth strategies must evolve by level: The approach that gets you to level four ($1M-$10M) won't get you to level five ($10M-$100M). Higher wealth levels typically require entrepreneurship or equity ownership. "The strategy that you use to get into level four is not going to be the strategy that gets you out." Know when "enough" is enough: Level four wealth ($1M-$10M) may be sufficient for most people. The sacrifices required to reach higher levels often aren't worth the marginal benefits. "The rational response for an American household once they get into level four is... maybe I take my foot off the gas and just enjoy life more." As a data scientist, Nick leverages data to provide business intelligence insights at Ritholtz Wealth Management, where he also serves as Chief Operating Officer. His work involves analyzing data to answer business questions, identify trends, and build predictive models. For example, he might analyze lead conversion rates, client attrition, or investment patterns to inform business decisions. Financial independence requires separate identities: Maintain individual financial accounts within marriage for independence and easier asset division. Pool resources for shared expenses while preserving autonomy. "Everyone needs to have their own accounts. They need to have their own money... especially important for women." Nick and his wife have a joint + separate bank account(s). Here's how it works: All of your income and your partner’s income flows into this joint account. That income is used to pay for all shared expenses. Any excess left in the account (above a certain threshold) can either be left in the account or distributed equally between you and your partner (to your separate accounts). Apply to be part of my
/episode/index/show/learningleadershow/id/37484150
info_outline
645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity
07/20/2025
645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity
Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Ryan Petersen is the founder and CEO of Flexport, a technology-driven global logistics company. He’s a leading voice in supply chain innovation and has been at the forefront of solving major trade and shipping challenges worldwide. Notes: “Arrogance is its own form of stupidity.” The Tweetstorm That Saved Christmas: Ryan shares the now-legendary story of how he rented a boat, brought tacos, and took another high-powered CEO with him to tour the Port of Long Beach during the supply chain crisis. His viral Twitter thread sparked immediate action, California Governor Gavin Newsom called within hours, and the policy changed shortly after. A masterclass in “doing the thing.” Frontline Obsession & Gemba Walks: Why Ryan frequently travels the world (visiting 19 countries last year) to meet employees and customers. He explains the power of Gemba walks, being physically present on the frontlines, and how it shapes his leadership. How He Runs Flexport: Ryan’s leadership playbook includes: Managing through writing. Every one of his 26 teams writes a six-page memo monthly, followed by deep conversations. Daily conversations with 30-40 employees to stay connected. Living Flexport’s values: Empower Clients, Play the Long Game, Act Like an Entrepreneur, Commit to the Vision, Ask Why 5 Times. Leadership & Decision-Making: He shares his “must-haves” for hiring leaders: Relentless Work Ethic Intellectual Curiosity Humility (“Even wise people are wrong 30% of the time.”) Reliability Charisma Lessons from Mentors: Ryan talks about advice from Paul Graham (Y Combinator) and Brian Chesky (Airbnb), including how gathering your top leaders in person sparks innovation and alignment. Hard Decisions & Mistakes: He candidly discusses Flexport’s CEO transition gone wrong, hiring Dave Clark from Amazon, and what he learned from that difficult chapter. Personal Growth & Life Philosophy: Ryan shares his approach to lifelong learning, inspired by Charlie Munger and René Girard. He emphasizes reading widely, asking questions, and choosing role models wisely. "We’re all imitative people. Choose your role models wisely." “We’re making global trade as simple and reliable as flipping a light switch.” “Even wise people are wrong 30% of the time. You must stay humble.”
/episode/index/show/learningleadershow/id/37338625
info_outline
644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People
07/13/2025
644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People
Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to Guest: Blaine Anderson is a dating coach and matchmaker. She’s helped more than 3,000 happy clients attract and build long-term relationships. Her work has been featured in the New York Times, the Wall Street Journal, Forbes, and she earned a deal with Mark Cuban on Shark Tank. Notes: Someone asked Charlie Munger… How do I get a great wife? Deserve one. The best way to find a good spouse is to deserve one, he often said. In business, this translates to working hard and behaving with integrity consistently over time. “To get what you want, you have to deserve what you want.” What is the #1 reason you don’t get a second date? You talk about yourself too much. When you go out to eat with someone, what percentage of the time are you talking? Aim to talk 30% and listen 70%. The reason we don’t get the second date or the follow-up meeting with the prospect is because we are talking too much. Pull conversational threads: Avoid rapid-fire questioning by following up on answers with related questions. Share brief personal connections to create dialogue rather than interrogation. "You want to pull the conversational thread... ask a follow-up question about that same thing. That's where you can start having a conversation." Marketing your trajectory matters: People want to know you're going places. Share your goals, dreams, and aspirations authentically to demonstrate upward momentum. "You want to find the balance of sharing things about yourself that indicate you are on an upward trajectory... from a place of getting to know one another." Nice guys need boundaries: Being overly accommodating to people you barely know signals weakness. Hold boundaries and don't put others before yourself too quickly. "The general problem with the nice guy is he's putting other people before himself, including people he doesn't know very well." Confidence must be genuine: Authentic confidence comes from actually becoming confident through mastery, not just faking body language. Get genuinely good at something. "You have to become that... get really good at something... picking something in your life and getting really good at it is gonna help you build confidence." Don't rush to the close: Whether in dating or sales, focus on building connection and trust before asking for commitment. The close is the period at the end of a long sentence. "If you approach a woman or you approach a deal and you're just trying to get to the final step... you're going to rush through a lot of the important and essential steps." High-value people are in demand: Present yourself as someone others want to be around. People are naturally drawn to those who appear sought-after by others. "We want the thing that's in demand. We want the thing that other humans recognize as high value." Genuine curiosity creates connection: Being authentically interested in others' experiences is a powerful form of respect and love. Ask questions that take conversations deeper. "Your underlying emotion is important... becoming a genuinely curious person who is interested in meeting another human." Physical fitness affects confidence: Looking and feeling good about yourself impacts how you show up in every interaction. Invest in your physical health. "You gotta feel good about how you look... who wants to partner up with a slug? Nobody." "You should always be dating your partner, whether it's your first date, your 40th date, or you've been married for 40 years."' "The close is the period at the end of a very long sentence." "Deserve one." - Charlie Munger's advice on getting a great spouse Women want 3 things - social status, to be desired, flirty/fun… They want an optimist. If things aren’t going well, look in the mirror. Take accountability. Her Twitter profile picture. Show the whites of your eyes. Smile. She has two tattoos. Omega is her middle name. Cactus for Tucson, AZ. How to build genuine confidence? Get good at something. Become an expert. Work really really hard. Be in great physical shape. It’s hard to be confident if you don’t like how you look. Sounds harsh, but it’s true. Confidence comes from evidence. Create some evidence for youself by consistently working hard and getting great at something. That confidence will ooze out of you wherever you go. Shark Tank. Scary, anxious, nervous. Did a deal with Mark Cuban. Advice - If you’re building a business, listen to what your customers want. What does your ideal client want? Build that.
/episode/index/show/learningleadershow/id/37290700
info_outline
643: Anthony Scaramucci - Getting Fired by President Trump, Working With a Life Coach, Playing Quarterback, Building Confidence + Charisma, Telling The Truth, & Finding Your Superpower
07/06/2025
643: Anthony Scaramucci - Getting Fired by President Trump, Working With a Life Coach, Playing Quarterback, Building Confidence + Charisma, Telling The Truth, & Finding Your Superpower
Go to for all show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to Anthony Scaramucci served as the White House Director of Communications for President Donald Trump from July 21 to July 31, 2017. He was at Harvard Law School with President Barack Obama and First Lady Michelle Obama. He’s the founder and managing partner of SkyBridge Capital. And he’s the founder and Chairman of the SALT conference. Leadership through service: True leadership isn't about personal glory but about making others better and helping them succeed in their roles. Derek Jeter exemplified this by never caring about personal statistics, only team success. "If you're on the team, it's not about me, right? It's about you. How am I gonna make you better? Or how am I gonna make you feel good about your role? How am I gonna get you to think that I'm here to help you?" Flexibility and decision-making under pressure: Football taught Scaramucci the importance of reading situations quickly and making audibles at the line of scrimmage - skills that translate directly to business and life leadership. "You can't just say, okay, here's the game plan, right? Because that's what Mike Tyson says, right? You have the plan until you get punched in the face, or all battle plans go by the wayside with contact with the enemy." Resilience through adversity: Getting "your ass kicked" early in life builds the resilience needed for future challenges in business and politics. Early defeats teach you how to bounce back from failure. "That's called resilience, right? You gotta get over that... That's how you gotta get your ass kicked. Here I was... and I just remember feeling so puny... So how you gotta get over that." The confidence battle starts within: The first fight in life is with yourself - believing you're good enough and worthy to compete. Henry Ford's principle applies: "If you think you can or you can't, you are right." "The first fight is with yourself. Am I good enough? Am I worthy? Can I get to the game? Can I believe in myself enough so that I'm standing next to someone else who believes in themselves that I compete?" Accountability in relationships: When Scaramucci's marriage was in crisis, taking full accountability for his mistakes rather than deflecting blame was crucial to rebuilding the relationship. "I owe my wife Deirdre, a debt of gratitude for actually really loving me because I was off the rails on a few things... she's like, Hey, I'm not having this, so if you love me, get your shit together." Life coaching vs. therapy approach: Life coaching focuses on progression and future action ("What are we doing today to be better?") rather than regression into past issues. "I feel that therapy is a regression. Life coaching is a progression... forget about the past. What the hell are you gonna do? What are we doing today to make yourself a better person?" Forgiveness as liberation: Choosing to forgive both others and yourself removes the "millstone of regret" that weighs you down and prevents forward progress. "I can take that millstone of regret and leave it behind me, take it off of my neck and leave it behind me... human frailty and not judging it is not just you judging others, but also yourself." The comfortable outsider advantage: Being comfortable with your outsider status while still being able to operate in elite circles provides authentic confidence and relatability across all social levels. "I am a comfortable outsider. I'm not an insider... but I'm comfortable with it. You know, like guys like Trump or Rudy, they're uncomfortable. Outsiders... But I'm a comfortable outsider. I don't need to do that." Intellectual curiosity + neuroplasticity: Combining genuine curiosity about others with the ability to adapt and change allows you to move successfully between different social and professional circles. "Find your superpower... I think your superpower is very similar to my superpower... intellectual curiosity. And so if you can blend intellectual curiosity with neuroplasticity, meaning you can adopt and change... then you can move in various circles." Pivot for survival: Successful businesses and careers require constant reinvention. SkyBridge's conference business and pivot to Bitcoin were survival strategies that became major successes. "We were going outta business... This was an accidental survivor strategy. This was a pivot that we were making in order to stay in business. This was not some mastermind plan."
/episode/index/show/learningleadershow/id/37236325
info_outline
642: Jim Murphy - Inner Excellence, AJ Brown, Presence, Managing Fear, Daily Goals, & Understanding Our Greatest Needs
06/29/2025
642: Jim Murphy - Inner Excellence, AJ Brown, Presence, Managing Fear, Daily Goals, & Understanding Our Greatest Needs
Go to for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to Jim Murphy is a mental performance coach for some of the most accomplished professional athletes in the world. Formerly a professional baseball player, he now focuses on helping others. You may have heard of him if you were watching the Philadelphia Eagles' playoff run last season, and star wide receiver AJ Brown was reading Jim’s book Inner Excellence on the sideline between offensive series. Notes: The first 11 days of 2025, Inner Excellence (originally published 16 years ago) sold about 25 copies… What happened on January 12? AJ Brown was shown on TV reading it in between offensive series. It then sold 200,000 copies in 20 days. Fear is a concern about the future. Give the best of what you have today. Be present. Heart, will, spirit = the deepest part of you When we’re at our best, there’s no thought of self. 5 greatest needs That we have value Love and acceptance Integrity Purpose beyond self Growth Dick Vermiel’s coaching style - Coach the person first. Then the sport (or the thing you’re doing). The same is true for any leadership role. People won’t care what you think unless they know you actually care about them. 4 Daily Goals Give the best of what you have today Be present. Fear is a future thing. Be grateful Focus on what you can control Anxiety is a mind with too many thoughts and concerns. Need to face our fears. 3 Key Areas: Belief - expand what you think is possible. Freedom - play like a kid (let it rip). Focus - Be fully present Status vs amazing experiences. Love is the most powerful force in the universe. Joy comes from love. Love can come from weaknesses. Ego - Always comparing, creates a fear of screwing up Rory McIlroy – Didn’t care if he made the cut at the US Open. Played free and made a few birdies at the end of the second round and made the cut. Jim's Dedication: “My father, Donald C. Murphy. The one who greatly influenced me to think deeply about what to love and what to let go of. I love you. See you soon.” His dad worked on the Apollo 11 mission. The first lunar landing. Grade yourself on presence. 4 daily goals. Rate them 1-10. Anxiety is a sign that someone isn’t present. Jim has always struggled with being self-centered. Be non-judgmental. Share unconditional love. Ricky Scruggs - Former teammate and roommate in pro baseball. He invited me to the desert in 2003. Led me to take the risk to leave the safety of family and friends to pursue a meaningful life. What about for those people who say your stuff is "woo-woo?" “I get paid to help people perform better. And that’s what happens when you work with me.” “My whole life, I obsessed about being a superstar, being rich and famous. What I now realize is what I’ve always wanted was to feel fully alive. I’ve realized since that what I always really wanted was to feel fully alive. That’s what Inner Excellence is about. Pursuing a full life and letting everything else be added. We’re created for relationships." Among Jim's strengths is that he listens and doesn’t judge. That’s what many people want. “I have this one client, a pro athlete. He said, ‘Jim, I smoke, I gamble, I drink. I do all these things, but I don’t think you do all those things. Do you think we can work together?’ I said, ‘If you don’t judge me for not doing those things, I won’t judge you for doing those things.’ We became great friends.” Resonance Key #3 - Love Your Opponent. “The opponent is not the enemy– they’re our partner in the dance.” – Phil Jackson
/episode/index/show/learningleadershow/id/37133390
info_outline
641: Larry Connor - The Big 6 Leadership Attributes, Building a Values-Based Culture, Becoming a Billionaire, Working on Saturdays, Flying Into Space, Diving To The Mariana Trench, & Existing To Be The Best
06/22/2025
641: Larry Connor - The Big 6 Leadership Attributes, Building a Values-Based Culture, Becoming a Billionaire, Working on Saturdays, Flying Into Space, Diving To The Mariana Trench, & Existing To Be The Best
The Learning Leader Show with Ryan Hawk Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Larry Connor is an entrepreneur, non-profit activist investor, and adventurist. In business, he is best known for founding The Connor Group, a real estate investment firm, and growing it from $0 to $5 billion in assets. Outside of work, Larry lives an adventurous life. Within a 12 month period Larry did something that had never been done before. He completed 3 dives to the deepest part of the ocean (the Mariana Trench) AND traveled to the International Space Station as an astronaut. In addition to that, Larry is a private pilot and was part of a Le Mans racing team that has won championships. “At The Connor Group, we don’t have, and never will have, a mission statement. We have culture. When you have the latter, the former is not necessary.” The culture is built on 5 core values, on which we don’t compromise: Do the right thing People count Live the Circle of Success Think long-term, not short-term Relentless pursuit of excellence “We exist, quite simply, to be the best.” “We don’t hire for experience. We don’t hire for knowledge. We don’t care where you went to school. We hire for personality traits. Especially in leadership roles. You have to have the big 6. You have to have all 6. They are: 1. Be able to motivate and inspire others. 2. Self-accountability and ability to hold others accountable in an honest, direct manner. 3. Organizational multi-tasking. The speed of the game is fast. 4. Cultural fit. 5. Grit. Doing the thing that others say are impossible. 6. Work orientation. If you want to come in at 8:30, take a 90-minute lunch, and leave at 4:30, The Connor Group is not for you. “People never outperform their own self-image. So aim high!” “Mediocre people don’t like high achievers and high achievers don’t like mediocre people.” “By definition, if you want to be exceptional, you have to be different. If you’re like everybody else, you’re going to end up like everybody else.” In 2008, Larry said, “We simply decided we weren’t going to participate in the global recession.” 3 P’s - People, Plan, Process People’s performances are measured through daily, weekly, and monthly IAMs (Individual Accountability Meetings). Clear expectations and clear management. When I asked him about becoming a billionaire, Larry immediately jumped to the impact he’s having on others. “There are far more important standards than money. How well have you treated your associates? Have you made them better people? How much have you done to help other people? Have you made a difference?” All of that is available to all of us regardless of us being a billionaire or not. The company headquarters are next door to a hangar that houses a working model of the “Wright B Flyer” - The Wright Brothers’ first production airplane.
/episode/index/show/learningleadershow/id/36865625
info_outline
640: Tony Reno (Yale University Head Football Coach) - Writing a Team Creed, Leaving it Better Than You Found It, Going to Gettysburg, Leadership Retreats, & Winning Championships
06/15/2025
640: Tony Reno (Yale University Head Football Coach) - Writing a Team Creed, Leaving it Better Than You Found It, Going to Gettysburg, Leadership Retreats, & Winning Championships
Go to for full show notes The Learning Leader Show with Ryan Hawk gives you direct access to some of the most respected coaching minds in the world. Led by HOFer Sherri Coale, Brook Cupps, Geron Stokes, and Eli Leiker. Leaders who have built winning programs, led at the highest levels, and shaped the next generation of elite performers. The Arena is a Learning Leader Circle for Coaches only. We are opening applications now for our first cohort. If you'd like to be part of it, . Once the cohort is full, we will be pausing applications. This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. In Patient Pursuit of Greatness – In the spring of 2012, General McChrystal was teaching a leadership class at Yale. That’s when he met Tony Reno. He said about the meeting, “Not many things materially affect my trajectory. But this time was different. What was different? Coach Reno.” The goal of the program: “Leave the jersey better than you found it.” The team creed, a pledge written by players on Team 142 (the 2014 squad), as they do at the start of every practice: “I vow to believe in the process, I am mentally and physically tough, I compete with passion and overcome any challenges. I stand tall alongside my family at all times, I challenge my brother, believe in him, hold him accountable. As I create my own path I always put team before myself, I strive for excellence on and off the field, I hold myself to a higher standard. I am a Yale football player.” Standards - Every player must recite the creed. The younger players are coached by the older players. The brick tradition - At each practice, one player presents his brick, then adds it to the others in the tunnel-- a visual reminder of the team’s solidarity. Reno instituted the tradition to build camaraderie through candid reflection. Hero, Hometown, Hardship, Highlight. Someone who has impacted you. One word for the season. His players went to bat for him. On December 28, Casey Gerald '09, a cornerback, and 63 other former players sent a letter endorsing Coach Reno's candidacy to athletic director Tom Beckett, and later to president Richard Levin and provost Peter Salovey. 12 days later, he earned the job. Gettysburg Retreat: Yale's football team takes an annual retreat to Gettysburg with McChrystal to focus on leadership, bonding, and team culture. Presidential Leadership - Lead people, but don’t do it for them. When his players host recruits, they will tell Coach Reno if their character aligns with being a Yale football player. Coach Reno names a player of the day for each practice. The one who lives out their values and the Yale football player creed. Life/Career advice - Help you become the best version of yourself in all you do. Make you an elite leader. Maximize you as a football player. Help you find your passion.
/episode/index/show/learningleadershow/id/36926005
info_outline
639: Katie Gatti Tassin (Money with Katie) - Building A Media Business, The Morning Brew Acquisition, Knowing Your Retirement Number, & Living Up To High Expectations
06/08/2025
639: Katie Gatti Tassin (Money with Katie) - Building A Media Business, The Morning Brew Acquisition, Knowing Your Retirement Number, & Living Up To High Expectations
The Learning Leader Show with Ryan Hawk Go to for full show notes This is brought to you by . If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Katie Gatti Tassin is the author of the "Money with Katie" newsletter and podcast, both acquired by Morning Brew in 2022. Katie provides fresh personal finance advice with a unique outlook, coupled with deep, self-taught knowledge. Before founding Money with Katie in 2020, she worked professionally in marketing and user experience design for Southwest Airlines, Dell Technologies, and Meta. She’s the author of Rich Girl Nation: Taking Charge of Our Financial Futures. Notes: If you’re not curious about it, you’re not going to give it your all. But if you are, you can become relentless. Chase your curiosity and obsessions with great rigor. That passion and love for whatever the thing is can lead to big opportunities in your life. Do you want 100% of a grape or 25% of a watermelon? Advice Katie got when she was considering accepting the offer to be acquired by Morning Brew. The importance of having a coach. Katie talked about the life-changing impact her coach, Elizabeth, has had on her. Ambitious, motivated people who have high standards need help, too. In fact, maybe as much as anyone. It’s worth it to invest in yourself and find a person to talk with 1 on 1. Parents - High expectations, straight A's or bust. Driven, hard to turn it off. The Morning Brew acquisition - Money with Katie. Worked at Meta and did Money with Katie at the same time. Left for the acquisition. Austin Rief (CEO) DM'd her on Twitter and made an offer during their first 30-minute conversation. Big lesson - Your IP is everything. Book Dedication - “To the anonymous guy who 'works in finance' that used to relentlessly comment on my nascent website in 2018, urging me to quit writing about money and 'keep it to myself. I hope you’re well." Acknowledgments - “Mom, for all those quiet days spent sitting on the floor of the Lents branch library or wandering the stacks at Barnes & Noble. Dad, for spending your time after work at the kitchen table with me every time my homework involved numbers, and for being my number one fan.” How much money do you need to be financially free? Katie breaks down the 4% rule, why it works, and how it can be personalized and optimized for each person’s retirement needs. High Standards Can Be a Double-Edged Sword – "I am an incredibly driven person because of the people who raised me... But I also have a really hard time with turning it off. I can become very narrow-minded and obsessive about the things that I'm doing." Turn Critics Into Fuel – Katie dedicated her book to an anonymous finance professional who told her to "quit writing about money" and "keep it to herself." Sometimes the best fuel comes from those who doubt you. Money Transparency in Families Creates Advantages – Katie's parents openly discussed finances, including sharing their income. "I never really thought of it as something that was taboo... made it a lot easier for me now as an adult." The Power of Life Coaching for Entrepreneurs – After initial skepticism, Katie found a life coach who told her, "You are way too in your head. You are way too concerned with the minutia. You don't even know where you wanna go yet." Intellectual Property is Everything in Negotiations – "Your intellectual property is the most valuable thing that you are negotiating over... The primary value of the thing that I'm spending 60 hours a week working on needs to be accruing to me." The 25x Rule for Financial Freedom – Based on the 4% withdrawal rule: "Once you have accumulated 25 times your annual spending... You should theoretically be able to use 4% of that amount every year, withdraw it, and live on it." Marriage Changes Everything Financially – "Marriage is the most legally significant thing you will do in your life other than die, and you don't get so much as a leaflet about how your rights have just changed." Prenups Aren't About Distrust – They're about legal protection, especially for anyone who might leave the workforce. "If you spend decades out of the workforce... You need to ensure that if your partnership ends someday... You will have a certain amount of income." Desire Drives Excellence – "If you're not curious about it, you are not going to give it your all... There is such a difference in outcomes. If I am really into something that I'm working on, it's gonna be second to none."
/episode/index/show/learningleadershow/id/36848225