Beyond A Million
Brad Weimert, founder of Easy Pay Direct, interviews world-class entrepreneurs to explore tactics & strategies to build 8, 9, and 10-figure brands. Learn more at: https://beyondamillion.com/ All business is the same… but nobody really feels that way. The truth is – the BUILDING blocks of business are consistent across the board. Marketing, Sales, Operations, Finance, and Taxes... Apply to all businesses. With more than 30,000 businesses flowing through Easy Pay Direct (and the data behind them), Brad Weimert has found a litany of world-class experts to break down what’s working - and what’s not. With clients like Tony Robbins, Dean Graziosi, Hal Elrod and Grant Cardone, Easy Pay Direct is an amazing pool of knowledge and experience to pull from. Watch, Listen, and learn while you hear experts pull back the curtain and share cutting-edge marketing strategies, the latest sales techniques, the operational tools and tactics that make it all work, and the tax strategies that keep your money in your pocket. Whether you’re pushing through your first startup and learning the ropes, you’re an established 8 or 9-figure brand, or you’ve made an exit and are thinking about your next chapter… Beyond a Million will stretch your mind. Be sure to follow us wherever you get your podcasts so you never miss a new episode!
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238: He Built an 8-Figure Software Company AI Still Can’t Replace with Dean Guida
07/23/2026
238: He Built an 8-Figure Software Company AI Still Can’t Replace with Dean Guida
Dean Guida started Infragistics at 23 to build UX/UI tools for professional software developers. Thirty-seven years later, the company operates across six countries, its software is used by more than two million developers, and its customers span the entire S&P 500—including Fidelity, Morgan Stanley, Exxon, Intuit, and Bank of America. But AI can now generate functional software in minutes. So what prevents a company like Infragistics from becoming obsolete? I wanted to understand which parts of software AI will commoditize, where lasting competitive moats will still exist, and why Dean believes the idea that software is disappearing has been dramatically oversold. We also talk about how he built a multi-8-figure company without outside capital, why he might raise money if he started again today, and what founders need to build once grit alone is no longer enough to scale. Watch on YouTube: Let’s Connect: | | | | |
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237: How to Build Category-Defining Brands in Any Industry with Jim Donnelly
07/16/2026
237: How to Build Category-Defining Brands in Any Industry with Jim Donnelly
Today I’m talking to Jim Donnelly, a founder who has built and scaled businesses across travel, real estate, wellness, and longevity medicine. He built an online travel community with 300,000+ members that later rolled into Travelocity. He developed luxury real estate that still holds Charlotte’s record for price per square foot. He co-founded Restore Hyper Wellness and helped scale it to 225+ locations. Now, he’s building Humanaut Health, a longevity medicine company with $10M-per-clinic potential. But the interesting part isn’t just what Jim has built. It’s how he keeps moving into completely different industries and finding the opportunity before everyone else sees it. A lot of founders fail when they jump categories because they assume the same playbook will work again. Jim sees it differently. He’s clear about what transfers from one business to the next, what doesn’t, and why the best opportunities are often hiding inside big categories that already exist. We get into how he builds brands people actually care about, why he’d rather have fewer customers who love him than more customers who only like him, and the biggest lessons he learned after raising $140M in private equity. Watch on YouTube: Let’s Connect: | | | | |
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236: Geoff Woods on Why Most Founders Are Using AI All Wrong
07/09/2026
236: Geoff Woods on Why Most Founders Are Using AI All Wrong
Today I’m talking with Geoff Woods, author of The AI-Driven Leader and founder of AI Leadership, about why so many founders are using AI on the wrong problems. Geoff helped drive Jindal Steel & Power’s market cap from $750M to $12B in four years, and one of his points really stuck with me: you don’t get beyond a million because you write great emails. But that’s exactly how a lot of entrepreneurs are using AI right now. Writing emails, cleaning up inboxes, building random agents, and mistaking activity for leverage. That’s the trap. AI can make you feel productive while you point all that horsepower at work that doesn’t actually move the business forward. Geoff walks through what it looks like to flip that: using AI as a strategic thought partner instead of an errand boy, why most leaders are skipping steps they haven’t earned yet, and how to think about AI in a way that improves decision-making, focus, and team performance. Geoff also shares what he learned helping scale a multi-billion-dollar company, why letting the right fires burn is part of leadership, and the move his assistant made to rewrite her own job description and 100x her role. If you’ve been treating AI like a faster Google, this conversation will reframe what it can actually do for you as a founder. Watch on YouTube: Let’s Connect: | | | | |
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235: Bootstrapping a $100M Supplement Brand with Matt Gallant
07/02/2026
235: Bootstrapping a $100M Supplement Brand with Matt Gallant
Today I’m talking to Matt Gallant, co-founder of BioOptimizers, a supplement company generating $10M a month with a larger mission to help people live healthier for longer. Matt started with a simple realization: if he could get great at marketing, he could build a business in almost any category. That belief eventually led him into health, supplements, and BioOptimizers—but not without some hard-earned lessons along the way. We talk about the moment the business nearly fell apart, how Matt thinks about creating maximum customer value, timeless marketing principles, and the question he believes every entrepreneur needs to ask as markets get more crowded and customers become harder to win. Watch on YouTube: Let’s Connect: | | | | |
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234: Cameron Herold Shares the Hiring Mistakes Costing Founders Millions
06/25/2026
234: Cameron Herold Shares the Hiring Mistakes Costing Founders Millions
Today, Cameron Herold (Founder of COO Alliance) is back on the podcast to talk about one of the biggest reasons companies stop scaling: bad hiring. We get into why impressive resumes can be misleading, how to tell if someone has actually done the work, and the hiring mistakes that quietly cost companies years of progress. Cameron also breaks down why most entrepreneurs are never properly trained to interview, how he thinks about screening for culture, and what founders miss when they rely too heavily on resumes, references, and gut feel. We also talk about the side of entrepreneurship people rarely admit in real time: burnout, loneliness, identity, alcohol, retirement, and what happens when the business stops giving you the same hit it used to. Watch on YouTube: Let’s Connect: | | | | |
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233: From a 9-Figure Exit to a $10 Billion Data Center with Jason Van Gaal
06/18/2026
233: From a 9-Figure Exit to a $10 Billion Data Center with Jason Van Gaal
AI isn’t just creating a software boom, it’s creating an infrastructure crisis. As demand for AI explodes, the real bottleneck isn’t chips or models anymore. It’s power, cooling, permitting, and the ability to build data centers fast enough to keep up. Jason Van Gaal has spent more than a decade solving exactly that problem. After building and exiting multiple data center companies — including one of the largest Canadian tech exits of 2019 — Jason is now taking on his biggest project yet: building a $10 billion AI data center campus in Alberta powered by its own energy infrastructure. In this episode, we break down the future of AI infrastructure, why data centers are becoming power companies, the realities of scaling massive industrial projects, and what Jason learned from building, exiting, and starting over again. Key Takeaways with Jason Van Gaal From Two Exits to a $10B Swing Hire People Better Than Yourself Cutting Build Time to 120 Days Financing 400% Growth Without Imploding How He Invests After the Exit Why He Came Out of Retirement Why Alberta Won the Build Busting the Data Center Water Myth Noise, Infrasound, and Tinfoil Hats What Happens If Approvals Fail Why He Stays in His Lane Why Scaling Fast Is a Trap Learning Just in Time vs Just in Case Watch on YouTube: Let’s Connect: | | | | |
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232: AI, Acquisitions, and the Cost of Scaling a $1B Company with Bill Tyndall
06/11/2026
232: AI, Acquisitions, and the Cost of Scaling a $1B Company with Bill Tyndall
Today I’m talking to Bill Tyndall, who helped build Electric AI from an idea into a company approaching a billion-dollar valuation, raised $211M across eight funding rounds, and now serves as CEO of Techvera. Bill has spent his career building companies around automation, IT, cybersecurity, and digital transformation. But his biggest lesson isn’t just about AI. It’s about capacity. We get into why AI is a capacity multiplier—not a magic fix—how companies create artificial bottlenecks inside their own operations, and why clean data, better routing, strong documentation, and faster adoption may matter more than simply throwing new tools at the problem. Bill also opens up about the founder side of the journey: what it felt like to take money off the table, why a big exit didn’t create the happiness he expected, and how he now thinks about purpose, delegation, acquisitions, identity, and building a healthier company. Key Takeaways with Bill Tyndall (01:55) Business vs. Purpose (03:07) Will AI Kill Managed Service Providers? (04:40) Running a Business Like a Football Team (06:44) The Injury That Ended the NFL Dream (09:21) Why a "Boring" Industry Attracted $211M (14:50) What an MSP Actually Does (Plain English) (19:32) Artificial Capacity Constraints - $17M to $38M in 1 Year (23:22) Building Faster With AI Tools (26:38) Why He Walked Away From a $1 Billion Company (31:09) When Money Doesn’t Fix Happiness (37:25) How to Avoid Regret After An Exit (39:17) Effective Delegation (41:55) The Problem with Roll-Ups (46:12) Acquisition Integration Challenges (49:28) The First 120 Days After an Acquisition (51:22) Returning To The CEO Seat (54:38) AI As A Capacity Multiplier (58:11) AI Governance & Control (01:00:10) Advice For Young Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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231: The New Rules of Building a $100M Company with Roger Neel
06/04/2026
231: The New Rules of Building a $100M Company with Roger Neel
Roger Neel sold his SaaS company at $100M+ ARR, took three hours off, and dove straight into a health tech startup backed by Google Ventures and Dexcom. In this conversation, Roger breaks down the full arc — from founding Mavenlink in the teeth of the 2008 financial crash, to grinding through 13 years of customer base churn, fundraising rounds, and eventually selling to PE. He also shares what he'd do completely differently if he were starting today with AI tools at his disposal to build a 9-figure business. We get into his framework for evaluating whether a business is actually defensible (he calls it the 3 Ds), why most SaaS companies don't need a moat until they're past $10M, what really happens when you sell to a PE firm, and how a regulatory curveball nearly killed his new company Signos right before launch. Key Takeaways with Roger Neel (01:48) Building A $100M Company In The AI Era (04:03) The Origin Story Of Mavenlink (07:01) The Future Of SaaS And Custom Software (09:25) The Three Ds: Demand, Differentiation, Defensibility (17:18) Why He Jumped Into Health Tech (19:26) Finding Your Actual Passion In Business (21:51) How Signos Revolutionized Continuous Glucose Monitoring (27:27) When A Regulatory Shift Breaks Your Model (33:16) Bootstrapping Vs. Raising Capital (38:09) The 13-Year Growth Arc To Exit (41:54) Going Up Market Faster With AI (46:43) Selling To PE: How The Deal Actually Works (48:48) Why Keep Raising Instead Of Selling Earlier (50:24) PE vs. IPO (51:02) Picking The Right PE Firm (58:03) Advice For Raising Capital Today (59:30) AI Tools Entrepreneurs Should Be Using Watch on YouTube: Let’s Connect: | | | | |
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230: The Brutal Truth About Starting a Podcast in 2026 with John Lee Dumas
05/28/2026
230: The Brutal Truth About Starting a Podcast in 2026 with John Lee Dumas
John Lee Dumas has published a podcast episode every single day for 14 years, leading to more than 5,000 episodes of Entrepreneurs on Fire. He records seven interviews in a single day each week, built a multimillion-dollar media business around the show, and put together 12 straight years of $100K+ months in net profit. But when I asked him what he’d do if he were starting a podcast today, he didn’t hesitate. He said he would never launch an interview show. In fact, he called interview podcasts a waste of time for 99% of people making them today. Bold statement from someone who built his entire empire on one. So what would he do instead? He already tested it. John launched a second show built around a completely different model, and within months it was generating 5-figures a month while dominating a highly specific niche audience. In this episode, he breaks down exactly how he built it, and why he thinks it's the only kind of show worth starting in 2026. Key Takeaways with John Lee Dumas (00:47) Daily Podcasting for 14 Years (02:22) Creating a Great Interview Using AI (04:31) Publishing His Monthly Revenue for Years (07:20) The One Word Most Entrepreneurs Never Learn (10:11) Compare And Despair (12:01) Why Most Podcasts Are Garbage (13:31) Advice for Starting a Podcast 2026 (21:27) How Have His Monetization Channels Changed? (22:39) A $39 Journal Did $453K In 33 Days (24:45) F.O.C.U.S. — His Framework For Everything (27:25) Advantages of Living in Puerto Rico (30:43) What He Learned from the Military (32:50) His #1 Advice For New Entrepreneurs Watch on YouTube: https://youtu.be/6Mqu2jtox9c Let’s Connect: | | | | |
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229: Biking 2,000 Miles in 13 Days to Raise $1 Million with Matt King
05/21/2026
229: Biking 2,000 Miles in 13 Days to Raise $1 Million with Matt King
Today I’m talking to Matt King, CEO of GoBundance, host of The Matt King Show, and Chief of Staff for a family office managing high-level investments and operators. Matt is about to ride a bike 2,000 miles from Mexico to Canada while giving away $1 million to people in overlooked communities across America. We get into how he thinks about balance, why he believes entrepreneurs should stop chasing net worth and focus more on cash flow, and what he’s learned reviewing financial statements from ultra-high-net-worth investors. We also talk about how GoBundance scaled from a small mastermind into a 900-member community without destroying the culture, the investing mistakes he sees over and over again, and why the best operators are usually the people willing to admit they don’t have all the answers. Key Takeaways with Matt King (02:11) The Highest-ROI Skill (03:14) Why Balance Is Overrated (06:31) Prioritizing What Matters (08:52) Scaling Without Killing Culture (13:58) Genuine Contribution (19:20) What Great Investors Do Differently (23:48) Managing High-Ego Entrepreneurs (25:48) How Family Offices View Risk (31:23) The Red Flags That Kill Deals (35:33) Riding 2,000 Miles & Raising $1M (49:46) Play Calling for Your Life (52:03) Non-Negotiable Recovery Habits (53:46) Empowering Kids with Core Values (55:37) The Amputee Who Wouldn't Quit (57:18) Advice for New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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228: How Tommy John Became a 9-Figure Underwear Brand with Tom Patterson
05/14/2026
228: How Tommy John Became a 9-Figure Underwear Brand with Tom Patterson
Today, I’m talking with Tom Patterson, founder of Tommy John, the underwear brand that turned a frustrating problem into a 9-figure business. Tom started the company after getting tired of undershirts constantly coming untucked while working in medical sales. What began as a simple fix turned into one of the biggest direct-to-consumer apparel success stories of the last 15 years. In this conversation, we break down how Tommy John bootstrapped its way to over $100M in revenue before taking meaningful outside capital, why Howard Stern and Kevin Hart became game-changing growth channels, and what founders misunderstand about building premium consumer brands today. Tom also shares lessons on raising capital, balancing wholesale with direct-to-consumer, building a company with your spouse, and why experience can actually become a disadvantage in fast-changing markets. Key Takeaways (01:27) Leveraging Howard Stern’s Audience (03:08) Pioneering Podcast/Radio Marketing (04:25) Starting Tommy John with $100 and a Sketch (07:27) How Useful is a Patent? (11:12) Evolve and Innovate (13:49) AI’s Future In Product Development (15:04) How to Defend Against Knockoffs (18:01) Wholesale Vs DTC Margins Explained (21:33) Why Women Became 30% of Sales (26:26) How Tommy John Financed Growth (30:47) Kevin Hart’s Unexpected Partnership (33:08) The Kobe Bryant Deal That Fell Apart (36:05) Selling A Minority Stake (38:20) Running A Business With Your Spouse (42:36) Experience Can Be Your Worst Enemy (44:38) Handing Off The CEO Role (46:53) Avoiding The Post-Exit Crisis (48:24) Lifestyle Businesses Are Changing (50:23) The Truth About Raising Venture Capital (52:06) Advice For New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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227: Dan Brisse: From Pro Snowboarder to $500M in Real Estate
05/07/2026
227: Dan Brisse: From Pro Snowboarder to $500M in Real Estate
Dan Brisse won back-to-back X Games gold medals as one of the most dangerous urban snowboarders on the planet—jumping off parking garages, rooftops, and rails for a living. But while he was at the peak of his career, he was watching his heroes lose their homes, their wives, and their minds. So he did something different. He started investing. In this episode, Dan breaks down how he went from living on peanut butter and jelly sandwiches to co-founding Granite Towers—a real estate company that manages nearly $500M across 3,300+ apartment units. We get into how he protects downside in every deal, why multifamily real estate quietly compounds wealth, and what his exact investing criteria looks like today. We also get into hiring on core values, why urgency is a red flag in any investment, and the one piece of advice he's giving his 13-year-old son about building wealth. Key Takeaways with Dan Brisse (00:00) Intro (02:25) From Gold Medals to $500M AUM (02:41) The Snowboard Lesson That Saves Him Millions (03:40) His Mental Checklist Before a Crazy Jump (06:10) How Risk in Sports Translates to Real Estate (9:15) Why Most Pro Athletes Go Broke (14:19) Why Losing Is the Best Motivator (16:51) The Passive Income Mindset Shift (20:10) From Duplex to Real Estate Empire (24:39) Lessons in Real Estate Investing (35:56) Understanding Cap Rates & NOI (41:43) Criteria for Evaluating Real Estate Deals (49:40) Analyzing Real Estate Submarkets (53:45) What to Look for in a General Partner (58:43) How to Attract A-Players (01:04:47) Business With a Purpose (01:07:12) The #1 Habit Every Pro Athlete Needs (1:08:26) Advice to New Entrepreneurs (1:09:32) Would He Do It All Over Again? Watch on YouTube: Let’s Connect: | | | | |
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226: How He Scaled to $30M ARR (While Living a Life of Extreme Adventure) with Jonathan Ronzio
04/30/2026
226: How He Scaled to $30M ARR (While Living a Life of Extreme Adventure) with Jonathan Ronzio
I’m sitting down with Jonathan Ronzio, who scaled Trainual from an idea to $30M ARR—while building a company known for its culture and still finding time to climb mountains, run marathons, and live a full life outside of work. What stood out to me in this conversation is how intentional he’s been about building systems—not just in the business, but in his life. We talk about why most founders document the wrong things early, how structure actually creates freedom, and how AI is completely reshaping how companies build, sell, and operate. We also get into how he thinks about balance versus alignment, what changes (and what doesn’t) after raising capital, and why the most defining moments in business are usually the ones you never planned for. If you’re trying to scale without becoming consumed by your business, there’s a lot here worth paying attention to. Key Takeaways (00:00) Introduction (01:28) Summiting Aconcagua vs Closing a Series B (03:01) What Is Trainual and Why It Exists (03:52) The #1 Thing SaaS Founders Document Too Late (04:59) When to Create Company Core Values? (06:48) Why Structure Actually Creates Freedom (09:57) Which Processes Deserve SOPs? (11:43) How AI Transformed Trainual's Product Roadmap (15:16) Will AI Kill SaaS? His Honest Take (18:49) Figure Out How to Disrupt Your Business (20:38) Agentic AI and the New Outbound Playbook (22:34) The Exact AI Tech Stack His Team Uses (26:05) Data Security in the Age of AI (30:11) $400K in Credit Card Debt for FB Ads (32:27) Balance vs. Alignment (34:31) Why Daymond John Joined the Cap Table (38:05) Cultural Practices That Actually Work (39:48) Project Management & Communication Tools (43:36) How to Define Culture at Scale (46:30) Mountaineering Lessons That Made Him a Better Leader (53:08) Living an Adventurous Life (58:50) Obsessive Compulsive Creative Disorder (59:43) Advice for Founders Torn Between Focus and Exploration Watch on YouTube: Let’s Connect: | | | | |
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225: Selling for 10x by Building What Customers Have to Buy with Will Caldwell
04/23/2026
225: Selling for 10x by Building What Customers Have to Buy with Will Caldwell
You don’t need to create demand if demand is mandated. That’s the insight Will Caldwell used to build and sell his company. Will discovered that inside the mortgage industry, banks are legally required to buy flood certificates on every loan. So, he started Snap — a platform that makes it faster and cheaper for banks to do exactly that. Then he partnered with Intercontinental Exchange, the $95 billion company that owns the New York Stock Exchange, plugged into their existing infrastructure, scaled quickly, and eventually sold 51% of the company for 10x. In this episode, we break down how to build within regulated industries, tap into existing demand, and scale without chasing customers. Key Takeaways (00:00) Small Teams Beat Large Companies (01:52) Why “Fat Cats Don’t Hunt” (03:13) Starting His First Tech Company (06:09) Knowing When to Shut Down a Business (06:51) Turning a $100 Compliance Headache Into a Startup (09:03) Finding Opportunity in Regulated Industries (16:58) AI Underwriting (21:09) Scaling via Strategic Partnerships (24:00) Selling 45 Banks in One Month (30:56) Selling to Intercontinental Exchange for 10x (32:31) Why He Sold Only 51% of the Company (36:10) Don’t Build the Tech Until You Have THIS (37:44) What Post-Exit Life is Like (38:41) What Will is Investing In Right Now (40:00) Advice for Entrepreneurs Starting Today (40:27) Books That Have Shaped His Thinking Watch on YouTube: Let’s Connect: | | | | |
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224: How One Consulting Client Led to an 8-Figure SaaS Product with Chris Taylor
04/16/2026
224: How One Consulting Client Led to an 8-Figure SaaS Product with Chris Taylor
Today I’m talking with Chris Taylor, an entrepreneur who turned a consulting engagement with Nissan into a software company serving half the automotive industry—then sold the business for multiple eight figures without ever raising outside capital. In this conversation, Chris shares how a consulting project with Nissan became the foundation of his company, how that journey ultimately led to an acquisition, and the earn-out lessons every founder should understand before selling their business. We also talk about building culture, why founder communities like YPO and EO can accelerate growth, and how AI is changing the economics of software and services. Key Takeaways with Chris Taylor (00:00) Intro (01:23) Bootstrapping vs Venture Capital (02:17) Is Every Growth Stage Equally Hard? (04:26) Why Founder Communities Change Everything (09:41) Is SaaS Dead in the Age of AI? (12:30) Why Outcome-Based Billing Could Kill SaaS Seats (15:28) How Chris Got Nissan to Fund His Next Startup (23:09) Turning Consulting Into a Scalable Product (33:11) Why Everything in Business Is Negotiable (40:43) The Real Path to Getting Acquired (48:30) Building Culture in an Unconventional Office (59:20) Earn-Out Lessons Every Founder Should Know Watch on YouTube: Let’s Connect: | | | | |
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223: Turning a Luggage Problem Into a $32M Apparel Brand with Dan Demsky
04/09/2026
223: Turning a Luggage Problem Into a $32M Apparel Brand with Dan Demsky
Today I’m talking to Dan Demsky, who turned the frustration of trying to pack light while traveling into an 8-figure e-commerce business. He discovered that merino wool clothing lets you pack far fewer items for a trip. The problem was, most of the brands were focused on outdoor gear—not something everyday travelers would actually wear. So Dan and his buddies built , a fully remote apparel brand doing $32M a year. In this episode, you’ll hear how they used crowdfunding to validate product-market fit and scale without investors, how tariffs nearly wiped out their business overnight, and what it actually takes to run a fully remote team. Key Takeaways with Dan Demsky (00:00) Starting an Apparel Brand (04:23) Crowdfunding as Product-Market Validation (05:27) Ecommerce’s Hardest Problem (06:52) When Tariffs Nearly Killed their Business (13:09) 30% Repeat Buyers in 30 Days (15:29) Using Crowdfunding as a Growth Engine (28:20) Running a Fully Remote Team (39:41) Should You Do Business with Best Friends? (51:17) Advice to New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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222: From Selling Weed to $1B in Real Estate Sales with Suneet Agarwal
04/02/2026
222: From Selling Weed to $1B in Real Estate Sales with Suneet Agarwal
Suneet Agarwal got raided by federal marshals in his underwear, lost everything from his cannabis business, sat on the couch breeding bulldogs for two years, and then built the #1 real estate team in California, selling more than $1B in a single year. In this episode we unpack that journey. We dig into the realities of building culture in a commission-based business, why personal brand is the biggest opportunity right now, and how AI-driven content helped Suneet build and sell a high-ticket coaching business. Key Takeaways with Suneet Agarwal (00:00) Intro (01:41) From Hippie Dispensary to Real Business (05:50) The Federal Raid That Took Everything (08:06) Home Invaded With a Gun to His Head (12:12) From Breeding Bulldogs to $1B in a Single Year (17:47) Are Real Estate Agents Overpaid? (22:44) Building Culture With 1099 Contractors (25:01) Leading from the Front (28:12) Are Real Estate Brokerages Dying? (30:22) Will AI Replace Real Estate Agents? (30:28) Launching One Of The First ChatGPT Courses (34:27) Using AI To Scale Content Creation (37:53) Will AI Kill the Coaching Industry? (38:43) Selling a Coaching Company Built on Organic (42:25) Straight To High-Ticket Offers (47:00) The Personal Brand Gold Rush (48:41) 95% AI Content That Doesn't Feel Like Slop (51:22) Advice for New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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221: How Jack Zimmermann Built 7 Hospitality Brands in One of the Hardest Industries
03/26/2026
221: How Jack Zimmermann Built 7 Hospitality Brands in One of the Hardest Industries
Opening a night club or restaurant looks fun from the outside, but behind the scenes it’s one of the most operationally complex businesses you can start. That’s why I was interested in speaking with Jack Zimmermann. After managing a team of over 200 people at XS in Las Vegas during its $100M peak, he returned to Austin to build Nova Hospitality, a portfolio of hospitality concepts including TenTen, Devil May Care, The Well, Mayfair, Neptune Sushi, LZR, and Coffee & Chill Austin. Most founders in this space struggle to make even a single concept work, and somehow Jack’s been able to start and scale 7. I wanted to find out how he decides which concepts to launch, how he funds them, and how he manages the risk and pressure that comes with leading hundreds of people. You don’t have to be a restaurateur to get value from this one. Let’s get into it! Key Takeaways with Jack Zimmermann (00:00) Running A $100M Vegas Nightclub (06:16) Why Clubs Must Constantly Find New Customers (07:00) Running Multiple Hospitality Concepts Successfully (11:02) The Shift In Alcohol Consumption (13:11) Taking Big Swings in Austin (15:07) New Locations vs Brand New Concepts (19:58) Using Partnerships To Expand Faster (22:27) Why Hospitality is So Hard (25:04) Staying Healthy in the Hospitality Industry (26:20) Letting Your Team Put Out the Fires (28:06) Funding Through Strategic Partnerships (31:42) How To Build A Hospitality Concept (36:47) What He Personally Refuses To Delegate (40:50) Leadership Advice That Stuck (41:45) Non-Negotiable Operating Principle (42:55) Where Austin Hospitality Is Headed (47:05) Advice For New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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220: Michael Chu on The Client Retention System That Prints Profit (LTV Framework)
03/19/2026
220: Michael Chu on The Client Retention System That Prints Profit (LTV Framework)
Today, I’m joined by Michael Chu — a five-time 7-figure founder who’s built over $100M in sales by focusing on one thing: retention. He believes churn isn’t a marketing problem, it’s a transformation problem. If you don’t change who your clients become, they won’t stay. In this episode, we break down the identity shifts, expectation gaps, and retention frameworks that turn short-term customers into long-term profit. And stay to the end, because we also unpack why retention in the AI era won’t be built on information, but on something far harder to replicate. Key Takeaways (00:00) Intro (01:13) Who Is Actually Qualified to Coach Anybody? (03:57) Why Great Sales Reps Fail As Managers (07:28) Teaching to Learn vs. Teaching Once You've Learned (09:57) Will AI Kill the Coaching Industry? (13:24) How He Went from 2 Clients to $250K/Month with No Ads (21:17) The First 72 Hours That Determine Customer LTV (26:20) Why McDonald's Never Gets Chargebacks (31:53) The Somatic Session That Unlocked $100K Months (38:18) LTV Built on Transformation, Not Revenue (44:01) The Framework for Employee and Client Retention (46:27) Why Belonging Beats Curriculum in the AI Era (50:45) The Framework Behind Every Great Training Watch on YouTube: Let’s Connect: | | | | |
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219: How He Built & Sold Two Companies for $550M with Ben Reubenstein
03/12/2026
219: How He Built & Sold Two Companies for $550M with Ben Reubenstein
Ben Rubenstein has built and sold two companies: Yodle for $342M and OpCity for $210M. In this episode, we break down the operating decisions behind those outcomes. We talk about when venture capital accelerates growth and when it can quietly kill your business. Ben explains why ideas are worthless without execution, how he scaled a 1,000-person sales organization, and the hiring filters that consistently produced top performers. We also get into culture, retention, speed-to-lead systems, and the strategic decisions that position companies for 9-figure exits. If you're building and thinking about capital, hiring, churn, or long-term optionality, this conversation is a masterclass in how experienced operators think. Key Takeaways 02:10 When to Raise VC? 04:25 Ideas Are Worthless 09:36 The 3 Traits of Elite Salespeople 14:13 Culture Doesn’t Happen by Accident 24:35 How to Sell – Scripts vs Talk Tracks 25:17 Yodel – From Air Mattress to $342M 29:27 Op City – Selling for Real Estate Brokerages 32:41 Are Real Estate Agents Overpaid? 38:45 Calling Leads within 4 Seconds 42:57 The Algorithm That Became their Competitive Moat 45:25 Why Most Founders Can’t Scale 46:43 Setting Expectations with Your Team 48:38 Hiring Top Talent 53:34 9-Figure Exit Strategies 58:30 The 80/20 Rule That Saves Startups 01:01:02 Setpoint – Private Capital for Asset-Backed Innovators 01:06:45 Advice to New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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218: Tom Shipley on Building Bigger Exits Through Acquisitions & Rollups
03/05/2026
218: Tom Shipley on Building Bigger Exits Through Acquisitions & Rollups
Private equity doesn’t scale the way most founders do. They buy growth. They acquire profitable businesses, combine them, and increase the value of the whole thing so they can sell at a much higher multiple. Today’s guest, Tom Shipley, is a serial entrepreneur and M&A strategist who built acquisition platforms applying that same strategy to founder-led businesses. In this episode, we unpack the mechanics behind scaling through acquisitions and rollups, how combining businesses can dramatically increase enterprise value, and why so many founders stall at $1–2M in EBITDA without positioning their companies for a meaningful exit. If you’ve ever wondered whether buying businesses is a distraction or a legitimate growth lever, this episode will change how you think about scale. Let’s dive in. Key Takeaways (00:00) Intro (01:54) The Two Biases That Destroy Acquisitions (05:00) The 4 Foundations of Business Growth (07:12) The AVA Roll-Up Story (Lessons Learned) (15:27) How to 4X Your Business Value (Multiple Expansion Explained) (19:11) How Acquisitions Outperform Organic Growth (21:26) The Roll-Up Mistake That Kills the Model (27:43) Add Zeros: How to Think Exponentially (30:51) When to Use Acquisitions as a Tool for Growth (39:27) Tom’s Playbook for Acquiring Businesses (54:55) What Is DealCon? (58:49) Turns $1–2M EBITDA Owners Into PE Deals (01:05:14) Advice to New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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217: How $100M DTC Brands Actually Measure Growth with Lomi Founder, Gareth Everard
02/26/2026
217: How $100M DTC Brands Actually Measure Growth with Lomi Founder, Gareth Everard
In this episode, , founder of and co-creator and former CMO of ($100M+ in 2 years), explains why revenue growth can be misleading and what serious DTC operators track instead. We unpack Gareth’s 4-lever framework for building a profitable eCommerce business, how to calculate allowable CAC before you truly know LTV, and why relying on future LTV assumptions can quietly break your financial model. We also get into his preference for funding via revenue over venture capital, why bundling often beats subscriptions, and the launch mechanics that helped Lomi generate $3M in its first 72 hours on Indiegogo. Key Takeaways (00:00) Intro (01:27) Crowdfunding Vs. Venture Capital Funding (03:25) Why Revenue Growth Can Kill a DTC Brand (06:45) The Real Math Behind SaaS vs. DTC Valuations (14:18) The 4 Levers of eCommerce (22:54) Why He Won’t Build Below 80% Gross Margin (26:23) Difficult Business Models (30:26) Is the Subscription Model the Right Move? (35:40) When Bundles Beat Subscriptions for LTV (39:50) How Lomi Did $3M in 72 Hours (43:48) Using Crowdfunding for Product Feedback (Carefully) (47:04) Contribution Margin Creates Optionality Watch on YouTube: Let’s Connect: | | | | |
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216: Amy Jo Martin on Quitting Her Job to Multiple 8-Figure Companies
02/19/2026
216: Amy Jo Martin on Quitting Her Job to Multiple 8-Figure Companies
Amy Jo Martin built one of the first social media agencies because Shaq told her to. True story. Seven years later, she shut it down. Not because it failed, but because it worked in a way that locked her into a life she didn’t want. Walking away gave her the freedom to decide what to build next. Since then, she’s scaled multiple 8-figure companies, written bestselling books, and hosts the Why Not Now? podcast where she’s interviewed countless celebrities. This conversation is packed with value for entrepreneurs building at every stage. We also go deep on what building a social media agency in 2009 can teach us about AI today — and what that means if you’re building anything right now. Key Takeaways with Amy Jo Martin (00:00) Intro (01:25) Social Media in 2009 vs AI Today (04:18) The Only Metric That Actually Matters (06:38) Shaq Told Me to Quit My Job (11:39) Is AI a Trampoline or a Trap? (15:32) Why the Agency Model Keeps Breaking (19:18) Can AI Improve Your Relationships? (23:34) The LinkedIn Hack That Replaces Hours of Biz Dev (28:03) This Kills The Traditional Brainstorm Meeting (31:20) Taking Tony Hsieh’s Money (34:44) Why She Shut Down a Profitable Company (38:34) When Personal Brand Becomes a Liability (43:24) Why AI Won’t Save Bad Marketing (45:52) The Real AI Problem Is Organizational Culture (51:06) The Renegade Reinvention Experiment (57:41) Can AI Help You Feel More Alive? (01:06:25) Action Creates Clarity (01:07:49) Don’t Raise Money Too Early Watch on YouTube: Let’s Connect: | | | | |
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215: Brian Luebben's Path from $750K to $10M in 3 Years
02/12/2026
215: Brian Luebben's Path from $750K to $10M in 3 Years
Two years ago, Brian Luebben was doing $750K a year. Now he’s posting million-dollar months. In this conversation, we break down what actually changed. It wasn’t a new tactic or growth hack. It was a shift in how he thinks about goals. That might sound a little woo-woo, but Brian explains why most entrepreneurs unknowingly limit their own growth, and outlines how a single shift in your thinking could completely alter the trajectory of your business. Not only does this conversation challenge how you think about growth, it also unpacks the operational decisions he made that supported the jump from sub-seven figures to a true eight-figure business. Key Takeaways with Brian Luebben 00:00 From $750K to $10M in 3 Years 04:34 The 3 People You Need to Be Around 09:55 Cashflow Investing vs Equity Investing 14:20 2 Frameworks from a $250M Mentor 17:45 Alex Hormozi Discipline 20:27 Long-Form Content To Scale Impact 22:51 How Career Capital Translates to Entrepreneurship 26:56 The Hires That Led to Million Dollar Months 32:00 Course Creation vs. Community Building 39:22 Expectations Matter More Than Price 44:52 Buy Businesses Then Learn To Run Them 49:53 Holding On Too Long Gets Expensive 56:33 Passive Income Is Mostly A Lie 59:18 Earn Your Summer 01:04:29 The Two Week Vacation Test Watch on YouTube: Let’s Connect: | | | | |
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214: Why Most Content Fails (And How The Algorithm Decides What Wins) with Pedro Jerez
02/05/2026
214: Why Most Content Fails (And How The Algorithm Decides What Wins) with Pedro Jerez
If you’re running content and ads without proof of what converts, you’re gambling. Today I’m talking with Pedro Jerez, an entrepreneur and growth strategist who’s led marketing for multiple 8- and 9-figure companies and spent years as a top 1% sales closer inside Tony Robbins’ organization. Pedro breaks down how a single, well-built offer can scale past 9-figures — and how to validate it in days, not months — instead of burning time and money on ideas that don’t convert. We get into the biggest content mistakes entrepreneurs make, the one metric algorithms use to decide what gets distribution, and how to use organic content to pressure-test creative before you ever spend on paid. Then we go deeper — what working for Tony Robbins was really like, the inner work most founders avoid, and how to shift from just making money to building businesses that align with how you want to live and lead. Key Takeaways with Pedro Jerez 01:45 Launching Too Many Offers Kills Scale 02:47 Validate Offers In Days, Not Months 03:51 Creative Is The Real Growth Lever 05:38 Media Buying Is Losing Its Edge 07:39 How Algorithms Decide What Content Wins 10:21 Which Platforms Should You Be On? 11:31 The Real Customer Buying Journey 14:00 Use AI To Pressure-Test Your Priorities 15:32 Reverse Engineer Where Demand Already Exists 18:17 Organic Content Predicts Paid Performance 19:25 How Targeting Actually Works In 2026 22:02 Fast Experiments Create Real Leverage 24:32 Consciously Rewire Your Reality 39:06 Tony Robbins Gave Him Frameworks, But Not Identity 44:27 Most People Underestimate What Mastery Takes 48:53 Obsessing Over Making Things Better 53:09 Move At The Speed Of Alignment 59:31 Miserable Millions to a Business that has Soul 01:05:37 What is Hum? 01:10:06 Advice for New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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213: The Proven Formula That’s Driven Over $1 BILLION in Sales with Jeff Walker
01/29/2026
213: The Proven Formula That’s Driven Over $1 BILLION in Sales with Jeff Walker
Today, I’m talking with Jeff Walker—the creator of Product Launch Formula® and the pioneer behind the modern launch model that’s driven over $1B+ in documented sales—to break down why product launches fail… According to Jeff, it almost always comes down to one thing: the offer. Not only does Jeff break down where failed launches miss the mark, but we pull on that thread to explore how launches have evolved over the years. What no longer works? What role does AI play? And how can entrepreneurs adapt as buyers get smarter and attention gets harder to earn? Jeff’s been doing online business for nearly 30 years, and he’s watched tools, platforms, and tactics come and go—and still, he continues to produce results while others chase what’s new. This episode is not only about launches, it’s about what actually holds up when you’re building a business over the long game. Check it out! Key Takeaways 00:00 Why Most Launches Fail 01:23 The Offer Is The #1 Lever 02:59 What Takes a Launch from Good to Great? 04:16 Delivering Value Before Reveal 05:28 The Origin of Product Launch Formula 14:43 The Core Elements of Product Launch Formula 20:10 What Launch Tactics No Longer Work? 25:54 The Challenge Model vs. Product Launch Formula 27:19 Why People Still Swear by the Product Launch Formula 31:20 Making a Difference in Peoples Lives 34:22 The Role AI Now Plays with PLF 37:33 Adventures as a Relationship Amplifier 47:21 Why Jeff’s Leaving His Business to His Kids 48:21 Designing Wealth Around Freedom 56:45 Advice for New Entrepreneurs Watch on YouTube: Let’s Connect: | | | | |
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How High-Performers Decide What to Ignore (Behind the Scenes with Stu McLaren)
01/26/2026
How High-Performers Decide What to Ignore (Behind the Scenes with Stu McLaren)
For a long time, being in rooms (masterminds, events, paid groups) were incredibly valuable for me. That’s where relationships were built, perspective expanded, and a lot of growth came from. But lately, I’ve been wrestling with whether that value still outweighs the cost—time, energy, relationships, broken routines, stepping away from the business, and more. And I know I’m not the only entrepreneur who struggles with this. That’s why I’m sharing this unreleased, behind-the-scenes footage from my interview with Stu McLaren. In it, Stu explains the exact rules he’s put in place to keep himself from being pulled in a hundred different directions when everything looks like a good opportunity. For him, this was critical, because without those rules, he knew he’d end up making WAY more money as an entrepreneur, but only at the cost of his family. This conversation completely reframed how I decide what to say yes to. And I think it’ll resonate if you’re wrestling with the same thing. Enjoy! Key Takeaways (00:00) Intro (01:00) Is Being In the Room Still Worth It? (01:47) The Cost of Being Away from Family (04:45) Why Travel Breaks Productivity (06:01) Calling BS On Nomad Efficiency (09:03) Stu’s Framework for Deciding What to Say YES to (14:26) Why Rules Create Freedom Watch on YouTube: Let’s Connect: | | | | |
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212: The Recurring Revenue Model Used by 20,000+ Entrepreneurs with Stu McLaren
01/22/2026
212: The Recurring Revenue Model Used by 20,000+ Entrepreneurs with Stu McLaren
If your revenue resets every month, growth is harder to predict, and harder to scale. That’s why so many companies are moving toward a membership model. A lot of businesses assume recurring revenue doesn’t apply to them. Today’s guest has spent nearly two decades proving that assumption wrong. Stu McLaren has helped more than 20,000 entrepreneurs to launch, grow, and scale membership-based businesses across nearly every industry imaginable—and in this conversation, he breaks down how to identify where recurring revenue already exists in your business and how to structure it into a membership that actually works. Stu also shares the single biggest factor that determines whether members stay or leave in the first 30 days. Don’t miss it! Key Takeaways (00:00) Intro (00:45) Why Predictable Revenue Lowers Founder Stress (02:40) Why “Passive Income” Is A Misleading Idea (03:16) How To Tell If A Membership Will Actually Work (06:26) You Only Need One Signal To Move Forward (07:31) Why Subscriptions And Memberships Are The Same (14:43) Turning One-Time Buyers Into Monthly Revenue (17:34) The Real Reason Members Quit In 3–6 Months (23:03) What Actually Matters In The First 30 Days (24:12) Why Retention Is A Customer Experience Problem (48:44) How To Lock In Retention By Highlighting Wins (59:03) The Mindset That Keeps Entrepreneurs Moving Watch on YouTube: Let’s Connect: | | | | |
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211: How a “Boring” Business Sold for 2x Market Value with Will Duke
01/15/2026
211: How a “Boring” Business Sold for 2x Market Value with Will Duke
Physical security is a brutally competitive, commoditized industry. Most companies look the same, act the same, and sell for the same. Will Duke did things differently. And when it came time to sell, buyers lined up. He didn’t just exit the core business. Along the way, Will built an internal software platform to manage and track thousands of security devices for customers. That platform eventually became its own SaaS company, and both businesses were sold as part of the same exit, at roughly double market value. In this episode, we break down how he differentiated in a crowded market, what actually mattered during the sale, and his repeatable process for investing smartly after an exit. If you want to understand what actually drives valuation, and why buyers were willing to pay a premium for Will’s business, this episode is definitely worth your time. Key Takeaways (00:00) Intro (00:45) Building a Business Over 20 Years (03:00) Selling Outcomes, Not Security Hardware (08:19) Using Data to Differentiate (14:00) The SaaS Tool that Became a Competitive Advantage (21:45) Video Surveillance for Small Business Owners (26:20) Advice for Entrepreneurs Exiting a Business (31:02) Exiting Two Companies at the Same Time (33:46) How to Use AI Before Talking to Attorneys (35:39) Maximizing Exit Value Through Culture & Core Values (43:07) Learning How to Invest Post-Exit (46:12) A Repeatable System for Vetting Investments Watch on YouTube: Let’s Connect: | | | | |
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210: How to Build a Luxury Brand That Attracts the Ultra Wealthy with Larry Walshe
01/08/2026
210: How to Build a Luxury Brand That Attracts the Ultra Wealthy with Larry Walshe
Today, I’m sitting down with Larry Walshe, founder of , a global event design firm producing large-scale, luxury weddings and private events for ultra-high-net-worth families, celebrities, and royal households. While Larry’s roots are in floristry, his work goes far beyond flowers. His studio designs fully customized experiences—shaping the creative vision, transforming spaces, and defining how guests experience an event—while bringing together specialized artisans from around the world to execute complex, high-stakes productions. In this episode, Larry breaks down what it actually takes to build and protect a premium brand at the top end of the market, how he orchestrates massive productions with a small team, and why learning to say no early was essential to attracting the right clients and scaling without lowering the bar. If you’re building a service business or premium brand and want a clearer sense of what it takes to operate at the highest level, this conversation offers a grounded look at how that kind of work actually gets done. Key Takeaways 00:00 Intro 00:55 Why Saying No Builds a Luxury Brand 03:28 Don’t Chase Revenue That Dilutes Your Brand 07:08 Consistency Is the Real Competitive Edge 08:20 Why High-End Clients Pay 10X More 13:07 Defining the Client You Actually Want 17:24 How to Shift Into a Higher-Paying Client Category 19:37 Inside Multimillion-Dollar Events 22:10 Running Global Operations With a Small Team 26:23 Becoming the Creative Director, Not the Doer 33:01 Managing Clients Who Want the Wrong Thing 35:03 The Sales Approach That Works at the Top End 40:02 When to Walk Away From Work 45:04 Handling Last-Second Client Demands 52:00 The Non-Negotiable's of Elite Client Work 57:15 Larry’s Advice for Founders Moving Upmarket Watch on YouTube: Let’s Connect: | | | | |
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