Leap Academy with Ilana Golan

John Paul DeJoria grew up with no connections, no money, and no roadmap. He sold encyclopedias door-to-door despite constant rejection, got fired from three consecutive jobs, and lived out of his car while raising his young son. Then, with just $700, he launched John Paul Mitchell Systems and built it into a billion-dollar haircare company. That same relentless spirit later helped him turn Patrón Tequila into one of the most recognized spirit brands in the world. In this episode, John Paul joins Ilana to share what it truly takes to build something from nothing, why rejection is just redirection, and why success unshared is failure.

John Paul DeJoria is a self-made billionaire, entrepreneur, and the visionary co-founder behind John Paul Mitchell Systems and Patrón Tequila. Beyond his iconic business achievements, he is a passionate philanthropist dedicated to creating a positive global impact.

In this episode, Ilana and John Paul will discuss:

(00:00) Introduction

(03:40) Growing Up in Foster Care as an Immigrant Kid

(11:20) The Navy Lessons That Shaped His Leadership

(15:23) Making It Through Sudden Homelessness

(23:23) How Getting Fired Led Him to Start Paul Mitchell

(28:22) How He Made Billions With Only $700 

(40:50) Letting Go of Fear, Failure, and Yesterday’s Mistakes

(46:14) Growing Patrón Against the Odds

(53:30) What Meeting Gaddafi Taught Him About Kindness

(56:57) The New AI Platform That’s Making Entrepreneurship Easier

(01:00:15) Why Happiness, Health, and Family Matter Most

John Paul DeJoria is a self-made billionaire, philanthropist, and co-founder of John Paul Mitchell Systems, the world’s largest privately owned salon haircare brand. He also co-founded The Patrón Spirits Company, growing it from zero distribution to over 3.5 million cases annually before its landmark sale. His upcoming memoir, Success Unshared Is Failure, details his extraordinary journey and his conviction that giving back is essential.

Connect with John Paul:

John Paul’s Website: peacelovehappinessfoundation.org

John Paul Mitchell Systems: https://www.paulmitchell.com

Resources Mentioned:

John Paul’s Book, Success Unshared is Failure: https://www.amazon.com/Success-Unshared-Failure-John-DeJoria/dp/B0FSTBMCJ8

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training

Despite his high intelligence, George Barrios nearly flunked out of both high school and college, drifting without discipline or direction. Realizing talent alone wouldn’t build the future he wanted, he cleaned up his act, became obsessive about preparation, and built a reputation for solving hard problems others avoided. That approach helped him rise through HBO and Time Warner before transforming WWE into a global media powerhouse. In this episode, George joins Ilana to share the habits that accelerated his career, the tough leadership decisions behind WWE’s growth, and the mindset shifts that helped him reinvent himself under pressure.

George Barrios is the former Co-President and CFO of WWE, where he helped transform the company into a global entertainment business. He is the founder of ISOS Capital, an investment and advisory firm focused on sports, media, and technology.

In this episode, Ilana and George will discuss:

(00:00) Introduction

(08:48) When Talent Turned Into Self-Sabotage

(13:12) The Turning Point: Meeting His Wife at UConn

(15:49) Fake It Till You Make It: Learning on the Job 

(23:17) Creating Opportunities After Rejection

(33:31) Driving Digital Growth at The New York Times

(39:38) Making Painful Decisions Under Pressure

(44:14) Transforming WWE into a Global Media Business

(50:35) The Fallout With Vince McMahon and WWE Exit

(59:27) Writing His Book and Sharing Hard Lessons

(01:05:52) Q&A: How Do I Open Doors in a Crowded Market?

George Barrios is a former Fortune 500 executive and the founder of ISOS Capital, an investment firm focused on global opportunities in sports, media, and technology. He previously served as Co-President and CFO of WWE and held leadership roles at The New York Times, HBO, and Praxair, building a track record in strategy, operations, and financial leadership. His new book, Sometimes Wrong but Never in Doubt, shares the lessons behind his unconventional path to success.

Connect with George:

LinkedIn: linkedin.com/in/georgebarrios/ 

Resources Mentioned:

George’s Book, Sometimes Wrong but Never in Doubt: How a Cuban Kid from Queens Transformed WWE: https://www.amazon.com/Sometimes-Wrong-but-Never-Doubt-ebook/dp/B0G4N4T9XV

The World is Flat: The Globalized World in the Twenty-First Century by Thomas Friedman: https://www.amazon.in/dp/0141034890 

Tony Khan: Building AEW into a Billion-Dollar Brand and Competing with Wrestling Giants: www.youtube.com/watch?v=Tqqfg-ysj0M 

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training

When Eric Ries built his first startup, he believed he had the perfect plan. But when no customers showed up, the business collapsed, exposing a costly truth: being certain does not make you right. That failure forced him to rethink his assumptions and ultimately led him to develop the Lean Startup method, a new way of building companies grounded in testing, learning, and truth. In this episode, Eric chats with Ilana about why most startups fail before they even launch, how to test ideas early to uncover what actually works, and how leaders can build companies that scale without losing their values.

Eric Ries is an entrepreneur, author, and startup strategist best known for creating The Lean Startup methodology, a framework that helps founders build businesses through rapid experimentation and continuous iteration. 

In this episode, Ilana and Eric will discuss:

(00:00) Introduction

(02:57) How His Childhood Curiosity Led Him to Computers

(08:55) Dropping Out of Yale to Chase a Startup Dream

(13:01) The Harsh Reality of the Entrepreneurship Fantasy

(14:53) Why Silicon Valley Loves Failed Startups

(19:37) Building, Scaling, and Leaving IMVU

(23:09) Reinventing Your Identity After Loss

(27:10) Tuning Out Bad Advice and Hearing What Matters

(30:40) Using Negative Feedback to Fuel Growth

(39:11) The Groundbreaking Lean Startup Philosophy

(46:13) The Worldwide Resistance to Innovation

(51:28) The Controversial Idea Behind Incorruptible

(57:18) The Entrepreneurial Near-Death Experience 

Eric Ries is an entrepreneur, author, and thought leader best known for creating the Lean Startup methodology, which transformed how startups and large companies build products. He is the founder of Long-Term Stock Exchange and has advised founders, executives, and organizations around the world on innovation, leadership, and long-term growth.

Connect with Eric:

Eric’s LinkedIn: linkedin.com/in/eries   

Eric’s X: x.com/ericries 

Resources Mentioned:

Eric’s Book, The Lean Startup: https://www.amazon.in/dp/0307887898 

Eric’s Book, Incorruptible: https://www.incorruptible.co/ 

Lean Startup Website: leanstartup.co/  

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training

Jason Feifer started his career writing about middle school dances at a tiny local newspaper, frustrated and convinced he was capable of more. Stuck in a role that wasn’t moving him forward, he quit, sat in his dumpy apartment next to a graveyard, and began cold-pitching major publications with no connections. That decision transformed his trajectory, eventually leading him to become Editor-in-Chief of Entrepreneur Magazine and a leading voice on career growth and adaptability. In this episode, Jason chats with Ilana about why doing only what’s expected of you slows your growth, how to identify opportunities, and steps to take control of your career in an unpredictable world.

Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a podcast host, book author, and keynote speaker who helps people build careers and companies they love by sharing lessons from the world's top entrepreneurs and leaders.

In this episode, Ilana and Jason will discuss:

(00:00) Introduction 

(03:48) Cold Pitches From a Bedroom Next to a Graveyard

(06:41) Developing an ‘Opportunity Set B’ Mindset

(09:51) Building Skills Strategically Across Jobs

(12:58) Renting a Title vs. Owning Your Name

(17:02) The Mission Statement That Survives Any Job Loss

(24:22) Why Jason Walked Away From His Biggest Hit

(31:51) How to Test Multiple Ventures At Once

(34:31) How a Lawsuit Accidentally Built Jason’s Success

(40:00) The Danger of Labeling Yourself

(47:47) Q&A: How Do You Become More Adaptable?

Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a role he has held for over 10 years. He is the author of Build for Tomorrow, host of the podcast Help Wanted, and a sought-after keynote speaker who has spoken for companies including Pfizer, Alibaba, Clorox, and more. Jason also advises startups, sits on multiple advisory boards, and writes the weekly newsletter One Thing Better. His work centers on adaptability, personal reinvention, and helping individuals and organizations thrive through change.

Connect with Jason

Jason’s Website: https://www.jasonfeifer.com 

Jason’s LinkedIn: linkedin.com/in/jasonfeifer 

Jason’s Instagram: https://www.instagram.com/heyfeifer/

Resources Mentioned:

Jason's Newsletter, One Thing Better: https://www.jasonfeifer.com⁠ 

Jason’s Book,

Build for Tomorrow: An Action Plan for Embracing Change, Adapting Fast, and Future-Proofing Your Career:

https://www.amazon.com/dp/059323538X

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training

Tim Draper didn’t become a legendary investor with billions in his account overnight; he started by taking a $6 million loan to launch his first venture fund, knowing failure was a real possibility. That decision didn’t just shape his career; it laid the foundation for backing some of the biggest companies in the world, including Hotmail, Skype, Tesla, and more. In this episode, Tim joins Ilana to break down how to spot world-changing ideas before they make sense, why most people miss their biggest opportunities, and how listening to your gut can be more powerful than logic alone. He shares the lessons behind massive wins like Hotmail, painful misses like Netflix, and the mindset required to navigate uncertainty, fear, and reinvention.

Tim Draper is a third-generation venture capitalist, founder of Draper University, and one of Silicon Valley's most legendary investors. He is a lifelong advocate for entrepreneurship, innovation, and the next generation of world-changing founders.

In this episode, Ilana and Tim will discuss:

(00:00) Introduction 

(04:11) Early Lessons on Money, Risk, and Capitalism

(08:43) Leaving Home at 13 and Learning to Figure It Out

(11:48) Venture Capital Roots and Family Background

(14:17) Taking a $6 Million Loan and Betting on Himself

(17:14) Spotting Billion-Dollar Companies Before Anyone Else

(20:11) The Viral Growth Strategy Behind Hotmail

(23:26) How Skype Changed Global Communication Forever

(29:18) Navigating the Dot-Com Crash

(34:13) Will AI and Crypto Follow the Same Boom Cycle?

(35:55) The Power of Listening to Your Gut as an Entrepreneur

(46:59) Q&A: How Do I Know What to Invest In? 

Tim Draper is a third-generation venture capitalist and founder of Draper University. He backed world-changing companies, including Hotmail, Skype, Tesla, SpaceX, Coinbase, and Robinhood. Known for spotting transformative trends before the mainstream, he's also a passionate advocate for entrepreneurship education, cryptocurrency, and celebrating innovation. His show Meet the Drapers reaches roughly 300 million people globally.

Connect with Tim

Tim’s Website: https://timothydraper.com/ 

Tim’s LinkedIn: https://www.linkedin.com/in/timothydraper/ 

Tim’s Instagram: https://www.instagram.com/timdraper/ 

Resources Mentioned:

Tim’s Book,

How to be the Startup Hero - A Guide and Textbook for Entrepreneurs and Aspiring Entrepreneurs: https://www.amazon.com/How-Startup-Hero-Textbook-Entrepreneurs/dp/1973585340/ref=cm_cr_arp_d_product_top?ie=UTF8

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training