Revisiting one of our most-downloaded episodes, Tom Bilyeu shares his powerful journey from self-doubt to self-mastery. His early years were shaped by fear of failure, a lack of direction, and doubts from those around him. After struggling to break into the film industry, he joined a startup with the goal of getting rich, but found himself unhappy and in a strained marriage. Taking a leap of faith, Tom walked away from millions to pursue something more meaningful. This gave rise to Quest Nutrition, a billion-dollar company creating nutritious, great-tasting products. Yet, for Tom, wealth was never the endgame. He launched Impact Theory, a media company designed to impact lives positively. In this episode, Tom shares with Ilana the key moments that shaped his career, the philosophies that drive him, and how he defines true success.

Tom Bilyeu is a billion-dollar entrepreneur, motivational speaker, co-founder of Quest Nutrition, and founder of Impact Theory. Through his content, he inspires millions by sharing tips on overcoming self-doubt, developing the right mindset, and building resilience for success.

In this episode, Ilana and Tom discuss:

(01:15) Introduction
(01:43) Facing Doubts and Rejection
(04:21) How Neuroscience Changed His Mindset
(06:28) Why People Struggle to Make Progress
(07:59) Learning the Power of Discipline in Film School
(12:46) Tom’s Guide to Finding Your Next Step
(15:25) Walking Away from $2 Million to Save His Marriage
(17:14) Building Quest Nutrition with the Right Team
(22:00) Why Tom Launched Quest Nutrition
(24:37) The Key to Surviving Entrepreneurship
(26:19) Strategies for Thriving in Competitive Markets
(30:20) Solving What Others Say Can't Be Done
(31:16) Conquering Fear Through Hard Work
(36:20) The Journey from Quest to Impact Theory
(40:15) Using Entertainment to Inspire Young Minds
(45:24) Lessons from Childhood that Built Tom’s Resilience
(48:06) Two Beliefs to Unlock Your Potential
(49:44) Letting Go of Ego to Grow

Connect with Tom:

Tom’s Website: https://tombilyeu.com
Tom’s YouTube: youtube.com/c/TomBilyeu
Tom’s Twitch: www.twitch.tv/tombilyeu

Leap Academy:

Ready to make the LEAP in your career? There is a NEW way for professionals to advance their careers and make 5–6 figures of extra income in record time.

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In one of our most popular episodes, Amy Porterfield had a dream job working with Tony Robbins, one of the world’s top motivational speakers and business strategists. But deep down, she wanted to be her own boss. During a high-level meeting, she realized she was on the wrong side of the table, watching entrepreneurs build wealth instead of becoming one. With no plan, no clients, and no backup, she left corporate life and built a $100 million online business. In this episode, Amy joins Ilana to share how she overcame imposter syndrome, depression, and anxiety to create a balanced life and the mindset shift that took her from employee to multimillion-dollar entrepreneur.

Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship.

In this episode, Ilana and Amy will discuss:

(00:00) Introduction 

(01:44) Entrepreneurial Lessons from Childhood

(03:35) Landing a Dream Job with Tony Robbins

(07:46) The Three Biggest Lessons from Working with Tony

(11:51) The Moment That Made Her Quit Corporate

(14:48) Overcoming Imposter Syndrome and Depression

(21:24) Finding Strength in Support Systems

(24:24) How to Transition from Employee to Entrepreneur

(27:32) Navigating the First Two Years in Business

(29:21) Redefining Success to Avoid Burnout

(35:20) Handling Hate and Criticism Online

(38:19) Shifting Your Money Mindset to Scale Faster

(43:35) Creating and Selling Profitable Digital Courses

(46:05) Why Mistakes Are the Key to Growth

Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She runs a $100 million company teaching entrepreneurs how to create, market, and sell profitable digital courses. As the host of the Online Marketing Made Easy podcast and bestselling author of Two Weeks Notice, she has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship.

Connect with Amy:

Amy’s Website: amyporterfield.com 

Amy’s LinkedIn: linkedin.com/in/amyporterfield

Resources Mentioned:

Amy’s Book, Two Weeks Notice: Find the Courage to Quit Your Job, Make More Money, Work Where You Want, and Change the World: https://www.amazon.com/Two-Weeks-Notice-Courage-Change/dp/1401969879 

The Let Them Theory: A Life-Changing Tool That Millions of People Can't Stop Talking About by Mel Robbins: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369 

Leap Academy:

Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time.

Check out our free training today at leapacademy.com/training

On our most replayed episode, Gary ‘Vee’ Vaynerchuk talks about how being scrappy wasn’t just a choice for him; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia. Overcoming the financial, mental, and emotional hurdles of entrepreneurship, he built his company into a multi-million-dollar media empire. In this episode, Gary joins Ilana to reveal the mindset and strategies you need to overcome obstacles and build your own multi-million-dollar business.

Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early.

In this episode, Ilana and Gary will discuss:

(00:00) Introduction 

(01:40) VaynerMedia's Scrappy Beginnings

(06:56) Why Businesses Fail Financially

(10:01) Navigating Tough Business Days

(17:21) The Risk of Over-Transparency in Leadership

(19:44) Dealing with Failure and Public Ridicule

(22:10) GaryVee’s Dream of Owning the New York Jets

(26:06) The Role of DNA and Accountability in Success

(28:35) Finding Joy in Entrepreneurship

(31:02) How to Build a Personal Brand as an Employee

(32:30) Empowering Employees with Honest Feedback

(34:27) Embracing Change and Executing Relentlessly

Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early.

Connect with Gary:

Gary’s Website: ⁠garyvaynerchuk.com⁠ 

Gary’s LinkedIn: ⁠linkedin.com/in/garyvaynerchuk⁠ 

Resources Mentioned:

Gary’s Book, Day Trading Attention: How to Actually Build Brand and Sales in the New Social Media World: ⁠https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591⁠ 

GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire: ⁠https://podcasts.apple.com/us/podcast/garyvee-from-earning-%242-an-hour-to-running-a/id1701718200?i=1000689595539⁠ 

Leap Academy:

Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time.

Check out our free training today at⁠ leapacademy.com/training

As a kid struggling with ADHD and financial instability, David watched his family nearly lose their home before taking a door-to-door sales job as a broke college student. He was terrible at it at first, but instead of quitting, he became obsessed with learning sales, systems, and business psychology. That mindset helped him build and sell four companies, scale across 5,000 cities in 34 states, and turn one of the world’s most overlooked industries into a $500 million empire. In this episode, David joins Ilana to share the sales lessons, leadership principles, and mindset shifts that helped him build through rejection, near-bankruptcy moments, and why some of the biggest opportunities today are hiding inside “boring” businesses.

David Royce is the chairman of AP Environmental, one of North America's largest residential pest control companies. Starting from door-to-door sales as a college student, he built and sold four companies, reaching over 5,000 cities across 34 states and a $500M valuation at exit.

In this episode, Ilana and David will discuss:

(00:00) Introduction

(04:58) The “Problem Kid” Who Built a $500M Business  

(13:22) Sales Skills Every Entrepreneur Needs

(17:06) Taking the Leap to Build His Own Business

(21:17) Surviving the Early Business Chaos

(29:02) Biggest Lessons from Tony Hsieh

(33:52) How Scaling Exposes Every Weakness

(37:45) The Failure That Forced David to Evolve

(41:39) How Bankruptcy Changed His Definition of Success

(45:34) “Boring” Businesses That Build Real Wealth

(54:37) The Power of Risks in Creating Bigger Lives

David Royce is a four-time exit founder and chairman of AP Environmental, one of North America's largest residential pest control companies. Starting from door-to-door sales, he built and sold four companies over the course of his career. His third company sold for a reported $135M, and his fourth, AP Environmental, reached a reported $500M valuation at exit, operating in over 5,000 cities across 34 states. 

Connect with David:

David’s LinkedIn: linkedin.com/in/david-royce-22539425  

Aptive Website: aptivepestcontrol.com/  

Resources Mentioned:

Delivering Happiness - A Path to Profits, Passion, and Purpose by Tony Hsieh: https://www.amazon.in/dp/145550890X. 

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

Mark Tluszcz had the career most people would chase: a top consulting job, rapid success, and a clear path forward. But eight years in, he made a move very few would dare to make. He left his high-paying job to start his own firm, faced hundreds of rejections while raising capital, and built Mangrove Capital from scratch. That same contrarian mindset led him to back companies others overlooked, becoming an early investor in Skype and later Chairman of Wix. In this episode, Mark joins Ilana to share how he invested early in Skype, spotted Wix before it became a global company, and why he turned down a $400 million acquisition offer. He also breaks down how to build conviction, embrace rejection, and find opportunities where others see risk.

Mark Tluszcz is the co-founder and CEO of Mangrove Capital Partners and chairman of Wix, one of the world's leading website-building platforms. He is widely regarded as one of Europe's most influential venture capitalists, known for his early investments in Skype and Wix.

In this episode, Ilana and Mark will discuss:

(00:00) Introduction

(05:36) Growing Up Across Multiple Cultures

(09:09) Leaving Corporate Consulting to Build His Own Firm

(13:58) Building Mangrove Capital During the Internet Boom

(20:54) How to Keep Going After Hundreds of Nos

(27:25) How Skype Evolved Beyond Music

(36:47) Staying Humble After a Massive Win

(43:08) Discovering Wix and Rethinking Venture Capital

(50:33) Turning Down a $400M Deal: The Wix Story

(57:41) Building Resilience Through Honest Conversations

(01:01:14) Spotting the Next Wave of AI Opportunity

(01:10:57) The Founder Mindset That Actually Lasts

Mark Tluszcz is the co-founder and CEO of Mangrove Capital Partners, a Luxembourg-based venture capital firm he built from the ground up after leaving Arthur Andersen in 2000. He was one of the first investors in Skype, where Mangrove’s $2 million investment reportedly returned $200 million, and he has served as chairman of Wix, where an $8 million investment reportedly yielded $700 million.

Connect with Mark:

X: x.com/marktluszcz 

Mark’s Instagram:  instagram.com/marktluszcz/ 

Mark’s LinkedIn: linkedin.com/in/mark-tluszcz-a024b51 

Mark’s Blog: https://www.daretodreambeyond.com/ 

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

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