loader from loading.io

Character, Competence, and Commitment with Kyle Skalisky

Million Dollar Relationships

Release Date: 01/23/2026

Why Phone Service Should Be Free with Derek Ting show art Why Phone Service Should Be Free with Derek Ting

Million Dollar Relationships

What if the frustration of a college student with a phone bill became the seed of a company serving 10 million people? Derek Ting is a multifaceted entrepreneur and filmmaker, known as the co-founder and CEO of telecom company TextNow, offering free mobile services, and also as an actor, director, and writer of action films like Agent Recon, starring alongside Chuck Norris. A native of New York with roots in Hong Kong, he splits his time between LA and HK, blending tech innovation with entertainment.. In this episode, Derek shares the relationships that shaped his path, from a mother who...

info_outline
A Second Chance to Make a First Impression with Tino Dietrich show art A Second Chance to Make a First Impression with Tino Dietrich

Million Dollar Relationships

What if a near-death experience was the thing that finally showed you what your life was really for? Tino Dietrich is a visionary entrepreneur, Inc. 500 honoree, and certified Mindvalley coach with a track record of building and scaling global businesses. As the founder and CEO of SNYDER Americas, he is spearheading the U.S. expansion of a premium German-engineered golf ball brand, disrupting the industry with innovation and precision. Tino also leads the Dietrich Institute, a coaching and consulting powerhouse dedicated to empowering high-achieving professionals to master personal growth,...

info_outline
How Relationships Built a Career and a Campaign with Frank Carone show art How Relationships Built a Career and a Campaign with Frank Carone

Million Dollar Relationships

What if the most powerful business strategy you could ever use isn't a strategy at all, but a lifelong commitment to showing up for people? Frank Carone is a seasoned legal and political strategist and the founder of Oaktree Solutions, where he guides businesses, nonprofits, and entrepreneurs through complex challenges at the intersection of law, regulation, and politics. With over three decades of experience as a lawyer and litigator, Frank has built a reputation for navigating the most intricate corridors of power in New York and beyond. Frank served as Chief of Staff to New York City Mayor...

info_outline
Building a Billion-Dollar Nonprofit Constellation with Ryan Dewey Smith show art Building a Billion-Dollar Nonprofit Constellation with Ryan Dewey Smith

Million Dollar Relationships

What if the secret to saving a mission wasn't a merger but building something big enough to protect it? In this episode, Ryan Dewey Smith shares how frustration with traditional merger models led him to incorporate Inperium on January 12, 2016, from a firehouse office in Reading, Pennsylvania. What started as a bold experiment in nonprofit consolidation has since grown into a constellation of 34 companies across 20 states, approaching $1 billion in annualized revenue and serving roughly 300,000 people a month. Inperium operates as a behind-the-scenes parent organization providing capital, HR,...

info_outline
From Burnout to Breakthrough: The Power of the V/I Duo with Clayton Stenson show art From Burnout to Breakthrough: The Power of the V/I Duo with Clayton Stenson

Million Dollar Relationships

What if the most important relationship in your business isn't with your biggest client but with the person sitting right next to you in the leadership seat? In this episode, Clayton Stenson shares how 17 years of working alongside visionary entrepreneurs became the foundation for his life's work: helping Visionary/Integrator duos build healthier partnerships so their companies can scale without costing them their families or their sanity. Clayton is the founder of Unity Guides, a fractional integrator, and a coach who has spent the last four years helping visionary entrepreneurs and their...

info_outline
The Relationship That Changed Everything with Ryan Ellefsen show art The Relationship That Changed Everything with Ryan Ellefsen

Million Dollar Relationships

What if the person who transformed your entire career is also someone you haven't spoken to in seven years? In this episode, Ryan Ellefsen shares how he helps businesses take credit cards, lower processing fees, and protect their revenue as VP of EasyPay Direct, a merchant services company he recently joined after 20 years in the industry. EasyPay serves coaches, consultants, speakers, and internet marketers,  processing payments for names like Tony Robbins, Grant Cardone, and Frank Kern across 34 US locations. Ryan built his career expertise under the mentorship of Steve Thorne, CEO of...

info_outline
How Emotional Healing Drives Workplace Success with Susan Winchester show art How Emotional Healing Drives Workplace Success with Susan Winchester

Million Dollar Relationships

What if workplace conflict is not something to avoid, but the very path to healing and high performance? In this episode, Susan Winchester shares how a 36-year corporate HR career evolved into a purpose-driven executive coaching and consulting practice focused on emotional intelligence, leadership effectiveness, and workplace healing. Susan served in senior HR leadership roles for global organizations including Kellogg's, Federal Reserve Bank of Chicago, Rockwell Automation, and Applied Materials. After retiring from corporate life at 60, she transitioned into her own consulting and executive...

info_outline
Honesty as a Business Strategy with Don Williams show art Honesty as a Business Strategy with Don Williams

Million Dollar Relationships

What if honesty is the only sales strategy you ever needed? In this episode, Kevin sits down with Don Williams, founder of Don Williams Global and a sales and leadership coach with over 30 years of experience. Don works primarily with founder-led businesses under $100 million, helping them grow their top line fast. He started selling at 19, became the top rep out of 450 within months, and has since worked with more than half of the Fortune 500. His core belief has never changed: the foundation of all sales and leadership is trust, and the only way to build it is to be trustworthy. The...

info_outline
Building on YouTube with Mary Ann Bautista and Matthew Pierce show art Building on YouTube with Mary Ann Bautista and Matthew Pierce

Million Dollar Relationships

What if the content you created in 2006 is still making you money today? In this episode, Kevin sits down with Mary Ann Bautista and Matthew Pierce, co-founders of Turbo Rank, in the first-ever two-guest interview on the show. With 30 years of direct response marketing behind them across TV, radio, and podcasting, they now specialize in helping mid-market businesses turn YouTube into a discoverable, revenue-generating channel. What makes their story remarkable is that they built Turbo Rank without ads, without outside funding, and without starting from zero. A client relationship they started...

info_outline
Playing The Long Game with Scott Rammage show art Playing The Long Game with Scott Rammage

Million Dollar Relationships

What if the connection that saves your life was nine years in the making, and you had no idea it was coming? In this episode, Scott Rammage shares how a chain of relationships built over nearly a decade led him to the doctor who restored his health when no one else could. Scott is the owner of HireVP, a virtual professionals agency that recruits, places, and fully supports experienced overseas staff for business owners across the U.S. and Australia. He spent 17 years learning the hard way what it costs to try to do everything yourself, losing money and time with his family in the process,...

info_outline
 
More Episodes

What if witnessing 10 deaths in 23 years changed your view on life?

In this episode, Kyle Skalisky shares how he helps teams build cultures of trust, respect, and accountability through his company Wyld Sky Aerospace and Management Consulting. After 23 years as a fighter pilot (F-15, F-16 aggressor, and F-18 in operational flight tests) and 15 years in the aerospace industry doing flight tests, Kyle recently stepped down as president and CEO of Check Six Aero Solutions to focus on giving back. His book "A Skyless Traveled: A Maverick Life of Leadership, Resilience, and the Pursuit of Purpose" shares lessons learned from the cockpit about building exceptional teams. Kyle believes good teams need three things: character (how people treat those who can do nothing for them), competence (people who can get the job done and are willing to learn), and commitment to the mission. He also wrote the book for his six and four-year-old sons, wanting to leave something showing what their father did for 50 years before they were born.

Kyle reveals three relationships that shaped him: meeting President Ronald Reagan at his Air Force Academy graduation in 1984, whose speech about being solution-oriented rather than a naysayer set the tone for his career; his parents who married at 16, had six kids by 29, and just celebrated their 72nd wedding anniversary teaching him dedication and never giving up on people; and his best friend Malibu, a talented pilot who died at 30 when he hit the ground during a Red Flag exercise. Witnessing 10-11 deaths in 23 years of flying changed Kyle's perspective—he stopped worrying about what people thought and started pursuing what brought joy, realizing that if no one will remember it in five years, it's just not that important.

 

[00:04:20] From CEO to Giving Back

  • Recently stepped down as president and CEO of Check Six Aero Solutions

  • Now runs Wyld Sky Aerospace and Management Consulting

  • Wrote book "A Skyless Traveled: A Maverick Life of Leadership, Resilience, and the Pursuit of Purpose"

  • Serves wonderful wife Dr. Kyra Carpenter and two boys Wilder (6) and Colt (4)

[00:06:00] Why Write the Book

  • Experience is great but people never get opportunity to pass it on to next generation

  • All people's stories are wonderful, wishes more could tell them

  • Wants to lift up next generation that will follow

  • Wrote book for his 6 and 4-year-old boys as older father

[00:06:40] Leaving a Legacy

  • Doesn't know how long he gets to be with boys growing up

  • Wanted to leave something showing 50 years before they were born

  • Show what their father did and what he believed in

  • Pass message down to true legacy: children and family

[00:07:20] Growing Up in Wenatchee, Washington

  • Parents married at 16, had six children by 29

  • Didn't have much but knew wanted to do something bigger

  • Didn't fly on airplane until 17 years old, senior in high school

  • First flight was to Air Force Academy physical at Whidbey Island

[00:08:00] The First Flight That Changed Everything

  • Had state playoff baseball game that afternoon across state

  • Local orchardist Jim Wade flew him in Cessna 172

  • Flying over Cascade Mountains, seeing Mount Rainier was transformative

  • Changed into uniform in car, was third batter, hit three-run homer off future major leaguer

[00:09:00] Air Force Academy and Finding His Passion

  • Second time flying was leaving for US Air Force Academy (only way to get to college)

  • Got exposed to things small town guy never traveled beyond family station wagon

  • Found passion for flying airplanes at young age

  • Stumbled into it with no idea it would be 23 years as fighter pilot

[00:10:00] Fighter Pilot Career

  • Flew F-15 operationally around the world for 23 years

  • Was F-16 aggressor (adversary/bad guy that trains combat pilots)

  • Did exchange tour with US Navy, flew F-18 in operational flight tests

  • Retired after 23 years, went to Raytheon

[00:10:40] Entrepreneurial Years

  • Owned Great Harvest Bread company franchise (had a bakery)

  • Co-owner of pro indoor football league team in Spokane

  • Taught him when it's your own money, think more about spending it

  • Helped when managing other people's money at Raytheon and Mitsubishi

[00:13:20] Proudest Moment: The Team That Didn't Need Me

  • At Raytheon, experimental R&D test airplane transitioning from single customer

  • Customer said they don't want exclusive use anymore, won't pay for it

  • Five year task to redefine mission, vision, create new organization

  • After five years: "This team doesn't need me anymore, they can do this without me"

[00:14:40] From One Program to 15

  • Had to go out and advertise capability to other Raytheon programs

  • Restructured team to support multiple test projects instead of just one

  • Asset went from supporting one program to 15-16 programs

  • Worth billions of dollars in sales to Raytheon

[00:15:40] Mitsubishi: Six Months of Success

  • Mitsubishi trying to certify new regional jet, program having problems

  • Took over program management and flight test team

  • Program for previous 5 years never met schedule or been on budget

  • Within first month, for next 6 months straight met schedule and under budget

[00:17:00] Refocusing the Team

  • Just through refocusing team, aligning tasks to priorities

  • Giving people clear idea of what they did and why important to mission

  • Aligned the focus and became best flight test team in business

  • Better than Boeing, Airbus, Bombardier, Embraer or any large OEMs

[00:19:00] Character, Competence, and Commitment

  • Good teams have people full of character (how they treat those who can do nothing for them)

  • Team needs competence (people who can get job done, willing to learn and improve)

  • Third C is commitment to what they're doing

  • Finding right people with all three is when you will succeed

[00:21:20] Meeting President Ronald Reagan

  • Air Force Academy graduation 1984, Reagan handed him diploma

  • Speech that day embodied how Kyle wanted to live his life

  • Not enough to be naysayer pointing out everything wrong

  • Have to be person who can bring forward solutions

[00:22:40] Reagan's Impact

  • Shaped views about what was valuable throughout life

  • Optimistic but understood reality, charismatic but not fake

  • Had guiding principles but willing to change

  • Genuinely liked people (important for any leader)

[00:24:00] His Parents' Influence

  • Parents are who really had impact on who he became

  • Never made it feel like they gave up something for kids

  • Felt true blessing was getting to have kids in their lives

  • Father was athlete of year, worked morning job, bartended at night while in college

[00:25:40] 72 Years Together

  • Parents both 88 years old, just had 72nd wedding anniversary

  • Even when times are hard, don't give up on people, work through it

  • Father didn't become major league player but channeled into coaching

  • Oldest brother became professional baseball player with Philadelphia Phillies

[00:27:00] Learning to Live in the Moment

  • Finding joy means learning to live in the moment

  • Let go of past but learn lessons, don't let it define you

  • Don't be so focused on future that you forget what's in front of you

  • Take opportunities that may take you on detour in life

[00:28:20] Losing Malibu

  • Best friend Jim "Malibu" Reynolds was academy graduate, talented flyer

  • Designed and built own aerobatic airplane, flew in air shows

  • Made mistake on range in Red Flag exercise, hit ground and died at 30

  • Changed Kyle at 30 years old, realized it can all end very quickly

[00:29:40] 10 Deaths in 23 Years

  • Saw at least 10-11 deaths in 23 years of flying

  • Changed how he looked at things and approached them

  • Before worried about everything, how people thought of him

  • Now: if no one will remember in 5 years, it's just not that important

[00:33:00] The Squadron Bar Ritual

  • Friday nights not just about drinking, it's a ritual

  • Chance to bond with people going through similar experience

  • Way to relax, find friendship and bonding in non-retribution way

  • Learned more in one-on-one conversations than formal meetings

 

KEY QUOTES

"I wrote a book because I have those six and four-year-old boys. I am an older father and I don't know how long I get to be with those boys growing up. I wanted to leave something to show for those 50 years before they were born, what their father did and what I believed in." - Kyle Skalisky

"Good teams have people full of character. You can't define that on a resume. It's how people treat those who can do nothing for them. But you also have to have competence. Then the third C is commitment." - Kyle Skalisky

CONNECT WITH KYLE SKALISKY 

🌐 Website: https://www.wyldsky-consulting.com 

📘 Facebook: https://www.facebook.com/kyle.skalisky 

💼 LinkedIn: https://www.linkedin.com/in/kyle-skalisky 

📚 Book: "A Skyless Traveled: A Maverick Life of Leadership, Resilience, and the Pursuit of Purpose" (available on Amazon)

 

Thanks for tuning in!

If you liked my show, please LEAVE A 5-STAR REVIEW, like, and subscribe!

Find me on:

Apple Podcasts | Spotify |  iHeart Radio | Stitcher