Leap Academy with Ilana Golan

Епизоде

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  CEO of MyFitnessPal Mike Fisher: He Applied for 1 Job, Then Became CEO | EP172 15.09.2026 1ч 5мин

  Mike Fisher’s career has taken him from West Point and flying helicopters in the U.S. Army to leading technology teams at PayPal, serving as CTO of Etsy, and ultimately becoming CEO of MyFitnessPal. In this episode, Mike joins Ilana to unpack the leadership lessons behind that unconventional journey. He shares what the military taught him about giving feedback, building trust, and learning from mistakes, and what he had to unlearn when he transitioned into the tech world. Mike also explains why nearly every major opportunity in his career came through the “hidden market,” why professionals should focus on building skills rather than chasing titles, and what stepping into the CEO seat taught him about imposter syndrome and leading through uncertainty. Plus, Mike shares what ultramarathons have taught him about pushing through dark moments, why great leaders need extraordinary willpower, and why he believes AI could ultimately create entirely new opportunities for entrepreneurs and professionals. Chapters 00:00 Trailer & Introduction 02:58 The Hidden Market: Why Your Best Opportunities Aren’t on Job Boards 04:05 What West Point Taught Mike About Leadership 06:57 Why Great Teams Debrief Their Mistakes 08:12 Learning Leadership the Hard Way as an Army Pilot 10:19 The Helicopter Accident That Changed How Mike Led 14:27 Leaving the Military for a Career in Tech 16:01 The Boss Who Changed the Trajectory of Mike’s Career 19:13 What Mike Had to Unlearn From the Military 20:58 How to Get People to Follow You Without a Title 22:56 Why Great Leaders Tell Great Stories 25:58 The Hidden Job Market & Why Your Network Matters 28:18 Why Weak Ties Can Lead to Your Biggest Opportunities 28:46 How to Make Sure People Remember You 29:04 From Consultant to CTO of Etsy 31:04 The Power of Extreme Focus 35:30 Stop Chasing Titles, Build Skills Instead 37:04 How the Hidden Market Led Mike to MyFitnessPal 38:33 Becoming CEO: What Changes at the Top 41:30 Imposter Syndrome at the CEO Level 44:56 Find the Skill You Can Always Fall Back On 45:27 What Ultramarathons Teach You About Leadership 47:51 “We Do Hard Things”: Transforming Etsy 50:27 Finding Your Reserve Tank in the Darkest Moments 53:09 Why You Should Never Go Through Hard Things Alone 53:28 “You Signed Up for This” 55:06 How to Rise Above the Noise in Your Career 56:08 Why Rejection Should Be Treated Like an Experiment 57:55 Mike’s Take on AI, Jobs & the Future of Work 59:58 Could a One Person Billion Dollar Company Already Exist? About Mike Fisher Mike Fisher is the CEO of MyFitnessPal and a technology executive whose career spans the military, entrepreneurship, consulting, and some of the most recognized technology companies in the world. A West Point graduate, Mike served as a U.S. Army aviation officer and helicopter pilot before transitioning into technology. His career has included leadership roles at PayPal, co-founding AKF Partners, and serving as CTO of Etsy, where he helped lead major technology and organizational transformations. Outside of work, Mike is an ultramarathoner and writes about leadership, technology, and business through his Substack, Fish Food for Thought. 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/
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  Peloton Co-Founder Tom Cortese: Building an $8.1B Brand & Knowing When to Walk Away | EP171 08.09.2026 1ч 27мин

  Tom Cortese helped turn an idea that investors rejected hundreds of times into Peloton—an $8.1 billion public company that completely changed the way millions of people exercise. But his story isn’t just about building Peloton. It’s also about knowing when to walk away from something that has become part of your identity and having the courage to start again.In this episode, Tom joins Ilana to share the real story behind Peloton—from starting the company with just $400,000 and getting rejected by investors to selling the first bikes, building an incredibly loyal community, and eventually taking the company public. Tom also opens up about the difficult decision to leave Peloton, why he realized he was the one who needed to go, and what it took to separate himself from a company that had been intertwined with nearly every part of his life. Now, he’s starting over—this time partnering with Chipotle founder Steve Ells to rethink fast food with Counter Service. Tom shares why leaving Peloton made this next chapter possible and what building something from scratch all over again has taught him about success, failure, identity, and reinvention. Chapters 00:00 From 400+ No’s to an $8.1 Billion Company 01:45 What Philosophy Taught Tom About Building Community 05:50 Why Your Career Doesn't Need to Follow a Straight Line 09:40 The Hidden Market: How Relationships Create Opportunities 12:00 The Opportunity That Turned Tom Into a Product Manager 15:05 Proust: Building a Great Product That Wasn’t a Great Business 18:49 How Tom Handled His First Startup Failure 21:58 The Night John Foley Pitched Him Peloton 25:53 Turning Boutique Fitness Into a Subscription Business 27:21 Starting Peloton With an Idea That Seemed Impossible 29:51 What Exactly Is Peloton? 31:19 Building Hardware, Software, Content & Community at Once 33:39 Start With the Customer Experience 36:20 When SoulCycle Banned the Peloton Founders 37:16 How Peloton Started With Just $400,000 39:40 Raising $5 Million After Investors Said No 43:33 How Tom Kept Going Through Rejection 45:41 Turning the Vision Into Something Investors Could Believe In 47:41 Building Peloton’s First Bike in Taiwan 50:50 Selling the First Bikes Through Kickstarter 52:45 How Peloton’s Community Took on a Life of Its Own 53:15 From 5,000 Bikes to an $8.1 Billion IPO 54:43 The Community That Changed Peloton 58:24 The Hardest Decision: Knowing It Was Time to Leave 1:02:20 “The Odd Man Out Was Me” 1:05:47 Separating His Identity From Peloton 1:08:35 Starting Over With Chipotle Founder Steve Ells 1:11:13 Why Tom Jumped Into the Fast Food Industry 1:13:21 The Problem Counter Service Is Trying to Solve 1:20:08 Why Leaving Peloton Made This Next Chapter Possible 1:23:51 What to Expect From Counter Service 1:27:29 Success, Failure & How Other People Tell Your Story 1:31:20 Dealing With the “Rise and Fall of Peloton” Narrative 1:33:28 What Tom Would Tell His Younger Self 1:35:02 What’s Next for Counter ServiceAbout Tom Cortese ABOUT TOM Tom Cortese is the co-founder of Peloton and CEO of Counter Service. Tom helped build Peloton from its earliest days, developing the product and experience that combined hardware, software, content, and community into a new category of connected fitness. The company grew from an initial $400,000 investment to a public company valued at more than $8 billion at its IPO. After stepping away from Peloton, Tom began exploring what his next chapter could look like. That journey ultimately connected him with Chipotle founder Steve Ells, and today the two are building Counter Service, a technology-driven restaurant concept focused on bringing better food, smarter operations, and a new approach to fast service. 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 Ilana’s free Leap Academy training: leapacademy.com/training 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/
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  Sir Richard Harpin: How He Turned £50K Into a £4 Billion Business | EP170 01.09.2026 55мин

  Sir Richard Harpin put £50,000 of his life savings into a business that nearly collapsed—twice. That company eventually became HomeServe, serving millions of customers globally before being sold for more than £4 billion. In this episode, Richard joins Ilana to share the lessons behind that extraordinary journey, from finding the business model that saved HomeServe with his final £10,000 to learning how to scale internationally, hire leaders better than himself, and stay focused when entrepreneurs are naturally drawn to the next big idea. Richard also shares lessons from his book, How to Make a Billion in Nine Steps, including why copying a proven model can be smarter than inventing something new, why every entrepreneur needs a “not-to-do” list, and the two mistakes he sees holding ambitious founders back. Chapters 00:00 Introduction 01:30 From £50K to a £4 Billion Exit 03:49 Richard’s First Business at Age Five 05:47 What Working at Procter & Gamble Taught Him 07:40 The Problem That Inspired HomeServe 08:37 Losing His Life Savings & Nearly Going Broke 10:12 Why Richard Refused to Give Up 11:19 Finding an Investor When the Business Was Struggling 12:40 The Final £10K That Changed Everything 15:14 Perseverance vs. Knowing When to Quit 16:26 Hiring His Replacement to Scale the Business 17:24 Taking HomeServe International 20:08 Evolution, Not Revolution 23:06 Why Direct Mail Still Works 24:59 Why You Need a “Not-to-Do” List 26:08 How Founders Can Avoid Shiny Object Syndrome 27:46 How Far Is Too Far From Your Core Business? 29:29 Scaling HomeServe Into a Global Business 32:14 Knighthood & Helping the Next Generation of Entrepreneurs 35:10 The Nine Steps Richard Wishes He Knew Earlier 37:42 Why Entrepreneurs Need Both a Coach and a Mentor 39:30 Stop Fixing Your Weaknesses—Build Around Your Strengths 40:52 What Holds High Achievers Back 42:52 Why Founders Need the Courage to Hire Expensive Talent 44:08 When to Bring in an Investor 45:44 You Don’t Need an Original Business Idea 46:26 Why Buying a Business May Be Smarter Than Starting One 47:35 Did Richard Ever Buy the Helicopter? About Sir Richard Harpin Sir Richard Harpin is the co-founder of HomeServe, the international home repairs and improvements business he helped grow from a struggling startup into a global company serving millions of customers. HomeServe was ultimately acquired in a deal valuing the company at more than £4 billion. Today, Richard focuses on helping the next generation of entrepreneurs build and scale successful businesses. He is also the author of How to Make a Billion in Nine Steps, where he shares the lessons he wishes he had known at the beginning of his entrepreneurial journey. 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/
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  Lovesac Founder Shawn Nelson: The Entrepreneurial Mindset That Built a Billion-Dollar Brand | EP168 25.08.2026 1ч 4мин

  At 18 years old, Shawn Nelson had a crazy idea: build a beanbag so massive it could fill an entire room. That idea eventually became Lovesac, a publicly traded furniture company and major consumer brand. In this episode, Shawn joins Ilana to share the real journey behind building Lovesac, from taking risks and learning as he went to winning Richard Branson’s The Rebel Billionaire and leading a company at scale. They also dive into what failure teaches us, why success never means you’ve “arrived,” how Shawn gets through the hardest days, and why his philosophy is to maintain top ambition with infinite patience. Chapters 00:00 – Introduction 04:06 – The Idea That Started Lovesac 07:10 – Stop Talking and Start Doing 13:24 – Big Vision, Flexible Execution 17:57 – Risk, Debt & the Fear of Failure 22:36 – Winning Richard Branson’s The Rebel Billionaire 29:11 – Lessons From Richard Branson & Virgin 32:07 – Why You Never Really “Arrive” 40:38 – What Failure Teaches You About Success 43:56 – Taking Lovesac Public & Leading at Scale 50:35 – How Shawn Gets Through the Hard Days 54:16 – The Reality of Entrepreneurship 56:24 – Building Your Career Safety Net & Personal Brand 1:00:59 – Lessons Shawn Wishes He Knew Earlier 1:03:27 – Top Ambition, Infinite Patience 1:05:30 – Redefining What Success Really Means 1:07:58 – Finding Your Personal “Why” 1:09:03 – The Truth Behind the Highlight Reel About Shawn Nelson Shawn Nelson is the founder and CEO of Lovesac, the publicly traded furniture company he started at just 18 years old. He is an entrepreneur, inventor, and winner of Richard Branson’s The Rebel Billionaire. Shawn is also the author of Let Me Save You 25 Years: Mistakes, Miracles, and Lessons from the Lovesac Story, where he shares lessons from more than two decades of building, nearly losing, and ultimately growing Lovesac into the brand it is today. Connect with Shawn Lovesac: Lovesac.com Book & Podcast: Let Me Save You 25 Years Social: @ShawnOfLovesac Leap Academy Ready to make the LEAP in your career? There is a new way for professionals to fast-track their careers and leap into bigger opportunities. Get started with Ilana’s free career training at leapacademy.com/training. 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/
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  Manu Sai Bakshi: From Starting Over to Recruiting Wall Street’s Top Talent | EP167 18.08.2026 1ч 4мин

  Manu Sai Bakshi arrived in New York with $2,500, a new wife, and a degree that wasn’t recognized in the U.S. Within weeks, he was applying for a job at Macy’s in Herald Square. That humbling beginning eventually led Manu into the hedge fund world, where he spent nearly a decade learning how the industry identifies and hires elite talent before launching Preeminence Advisors during COVID. In this episode, Manu joins Ilana to break down what separates great portfolio managers from mediocre ones, why reputation matters more than a quick fee, and how taking the harder path can become your greatest competitive advantage. Chapters 00:00 – Introduction 04:38 – What Is a Hedge Fund? Breaking It Down Simply 07:26 – From IBM to Macy’s: Manu’s First Days in New York 11:13 – The Differentiator: Cold Calling When No One Else Would 14:52 – Almost Fired—and Already Planning His Own Firm 18:24 – The Moment That Proved He Could Place Portfolio Managers 22:32 – What Makes a Great Portfolio Manager 25:17 – Why Reputation Is Everything 33:26 – Launching His Own Firm During COVID 37:22 – Building the First Client: Knock Their Socks Off 42:21 – How People Actually Become Portfolio Managers 46:40 – Manu’s Favorite Interview Questions and Red Flags 48:48 – The Biggest Hiring Mistakes Hedge Funds Make 53:47 – Q&A: How Do You Keep Going When You Feel Defeated? About Manu Sai Bakshi Manu Sai Bakshi is the Founder and CEO of Preeminence Advisors, a boutique search firm specializing in placing elite portfolio managers at multibillion-dollar hedge funds. After immigrating from India, Manu built his career from the ground up before spending nearly a decade leading recruiting inside a systematic hedge fund. Today, he works with senior hedge fund leaders as both a recruiter and strategic talent advisor. Leap Academy Ready to make the LEAP in your career? There is a new way for professionals to fast-track their careers and leap into bigger opportunities. Get started with Ilana’s free career training at leapacademy.com/training.
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  From Losing Everything to Startup of the Year: Ilana Golan’s 5 Shifts to Reinvent Yourself 11.08.2026 30мин

  Ilana Golan knows what it feels like to lose everything. After climbing from the Air Force to Intel to VP in a Silicon Valley startup, she thought she had made it. But when a trusted co-founder cut her out of their new business overnight, she was left with nothing. No job, no company, no income, and a shattered ego. That collapse became the turning point, forcing Ilana to ask who she was without the titles and what kind of life she truly wanted to build. In this episode, Ilana breaks down the five shifts you need to reinvent your career and the blueprint she used to bounce back from failure, build one of the fastest-growing startups, and land opportunities with leaders like Richard Branson and GaryVee. Ilana Golan is a serial entrepreneur, keynote speaker, investor, and host of the LEAP Academy podcast. As the founder of LEAP Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. In this episode, Ilana discusses: (00:00) Introduction (01:11) The Startup Collapse That Changed Everything (04:24) Losing Her Identity and Rebuilding From Scratch (06:22) Launching LEAP Academy and Reaching Startup of the Year (09:10) Reinvention as the Must-Have Skill of Our Era (10:09) The Power of Adaptability: IQ vs. EQ vs. AQ (11:29) The Five Shifts to Fast-Track Your Career (18:30) Commanding Authority: The Three Types of Branding (23:17) Creating a Portfolio Career for Freedom and Wealth Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana: Ilana’s Website: leapacademy.com Ilana’s LinkedIn: linkedin.com/in/ilanagolan Ilana’s Email: [email protected] 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. Join us for our free challenge August 11- 13th! https://workshops.leapacademy.com/challenge
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  Milk Bar CEO Christina Tosi: How a Home Baker Built One of America's Most Beloved Brands | E165 04.08.2026 1ч 16мин

  Christina Tosi didn’t have a clear five-year plan when she graduated from college. She tried different majors, worked odd jobs, and kept searching for the thing that felt like hers. Baking became the answer she could not ignore. With relentless persistence, she went from a hostess stand to New York restaurant kitchens, proving herself one dessert at a time. That same drive eventually turned a tiny laundromat space into Milk Bar, the dessert empire known for bold flavors, nostalgic treats, and joyful care packages shipped across the country. In this episode, Christina joins Ilana to share how experimentation leads to clarity, why failure is essential to mastery, and what it really takes to build a business rooted in creativity, community, and joy. Christina Tosi is the founder and CEO of Milk Bar, the iconic dessert brand known for its bold, nostalgic treats like the Compost Cookie and cereal milk soft serve. She is a two-time James Beard Award winner and New York Times bestselling author. In this episode, Ilana and Christina will discuss: (00:00) Introduction (05:53) How Childhood Baking Sparked a Career (10:04) Testing Different Paths Until One Felt Right (17:56) The Embarrassing Failure That Fueled Her (22:04) Finding Mentors and Moving to New York (28:10) The Simple Networking Move That Opened Doors (31:17) The Cookie That Put Milk Bar on the Map (38:00) Turning Failure Into Fuel for Growth (45:04) Building Milk Bar in a Tiny Laundromat (49:47) Pushing Through Criticism, Burnout, and COVID (1:03:10) The Shift from Pastry Chef to CEO (1:08:11) Why Discomfort Can Become Your Edge (1:16:43) Betting on Yourself Before You Feel Ready Christina Tosi is the founder and CEO of Milk Bar, a nationally beloved dessert brand with locations across the U.S. She is a two-time James Beard Award winner, TED speaker, and New York Times bestselling author of seven cookbooks. Christina also created Bake Club, a free online baking community launched during COVID that continues to bring bakers together around the world. Connect with Christina: Website: christinatosi.com/  Christina’s LinkedIn: linkedin.com/in/christina-tosi   Christina’s Instagram: instagram.com/christinatosi/  Christina’s YouTube: youtube.com/christinatosi  Resources Mentioned:Bake Club: bakeclub.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 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/
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  Google X's Astro Teller: Why the Biggest Breakthroughs Start with Failure | EP167 28.07.2026 1ч

  What does it really take to solve impossible problems? In this episode of Leap Academy with Ilana Golan, Ilana sits down with Astro Teller, CEO of Google X (Alphabet's Moonshot Factory), to uncover the mindset, leadership principles, and innovation frameworks behind some of the world's most groundbreaking technologies—including Waymo, Wing, and Google Brain. Astro shares why the biggest breakthroughs begin with embracing failure, how Google X celebrates shutting down projects that aren't working, and why successful innovators focus on solving the hardest problem first instead of chasing easy wins. From reinventing careers to building billion-dollar ideas, this conversation is packed with practical lessons on taking smarter risks, overcoming fear, and creating a process that leads to extraordinary results. Whether you're an entrepreneur, leader, or simply looking to future-proof your career, this episode will challenge the way you think about success, innovation, and what's possible. 00:00 Introduction 03:30 Meet Astro Teller & the Mission Behind Google X 05:15 How Astro Became CEO of Google's Moonshot Factory 07:30 What Makes a True Moonshot? 10:25 Why Google X Celebrates Failure 15:40 Rethinking Risk: Reward vs. Risk Ratio 19:10 The Reality of Building Breakthrough Innovation 21:45 How Waymo Went from Impossible to Reality 26:45 Wing: Reinventing Delivery with Autonomous Drones 29:20 The "Monkey vs. Pedestal" Framework 34:45 Building a Moonshot Mindset 39:00 The Origins of Google Brain & Today's AI Revolution 43:10 The Future of AI, Recycling & Manufacturing 45:15 Advice for Anyone Reinventing Their Career 47:20 Astro's Personal Journey & Lessons from Failure 52:10 Becoming a Ferocious Learner 54:25 Why Great Innovation Is Built by Teams 56:01 Final Thoughts Dr. Astro Teller is the CEO of Google X, Alphabet's Moonshot Factory, where he leads teams creating breakthrough technologies designed to solve some of humanity's biggest challenges. Since joining Google, Astro has helped launch world-changing innovations including Waymo, Wing, Google Brain, and Tapestry, while developing Google's unique approach to moonshot thinking and breakthrough innovation. Before Google, Astro was a successful entrepreneur, scientist, inventor, Stanford faculty member, and author. Today, he is recognized as one of the world's foremost voices on innovation, leadership, and the future of technology. Connect with Astro Google X (Alphabet's Moonshot Factory)https://x.company Astro Teller – Google X Profilehttps://x.company/astro-teller Astro Teller on LinkedInhttps://www.linkedin.com/in/astroteller 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 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/
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  The Corporate Ladder Is On Fire: How David Rogier Built MasterClass and What He’d Build Now | E165 21.07.2026 58мин

  At 16, his grandmother fled Kraków after the Nazis killed her father, worked a New York factory floor beside her mother, and applied to every medical school in the state three years running before one finally said yes — then told her second-grade grandson that education is the only thing nobody can ever take away from him.Years later, David Rogier quit his venture capital job with no idea what he wanted to build, and his boss wrote him a check for $500,000 and told him to go think of something; the dark, formless year that followed became MasterClass, whose holding company still carries his grandmother's nickname. Launch day brought so few sales that he went home and cried, and by day four it was obvious he had a real business on his hands. In this conversation, David breaks down how he got Hollywood's biggest names to say yes, why he believes degrees and résumés are quickly becoming worthless, and the three kinds of jobs he thinks will actually survive AI. David Rogier is the founder and CEO of MasterClass, the platform that put instruction from Martin Scorsese, Christina Aguilera, Steph Curry, and dozens of other world-class practitioners into the hands of millions of learners. He built it from a single $500,000 check and has since launched MasterClass Executive, an AI-native alternative to the traditional MBA created in collaboration with OpenAI and the University of Chicago Booth School of Business. IN THIS EPISODE, ILANA AND DAVID WILL DISCUSS: (00:00) Introduction (01:34) The Grandmother Who Survived Kraków and Became a Doctor (05:39) Stuttering, Teasing, and Parents Who Raised the Bar (07:15) Quitting His Job and Getting Handed a $500,000 Check (08:48) The Dark Year: What Happens When You Have No Constraints (12:58) The Three Things That Had to Be True for MasterClass to Work (14:33) The Lost Art of Opening Doors and Influencing People (19:46) Launch Day: No Calls, Almost No Sales, and a Lot of Tears (21:18) What Scorsese, Steph Curry, and Christina Aguilera Do Differently (23:53) Why “Hire Great People and Get Out of Their Way” Is Terrible Advice (27:28) The AI Study That Compressed 18 Months of School Into 18 Hours (34:16) The Skills That Matter Now: Learning Velocity, Execution, People (39:28) The Three Types of Jobs That Survive AI (44:39) Burning the Corporate Ladder: Rebuilding the MBA for $2,500(49:16) What He'd Tell His Younger Self (51:52) Q&A: My Network Feels Crowded — How Do I Get Real Introductions? CONNECT WITH DAVID ROGIER David's Company Website: https://www.masterclass.com David's LinkedIn: https://www.linkedin.com/in/drogier/ RESOURCES MENTIONED MasterClass: https://www.masterclass.com Chris Voss's MasterClass on Negotiation: https://www.masterclass.com/classes/chris-voss-teaches-the-art-of-negotiation LEAP Episode with Chris Voss: https://podcasts.apple.com/us/podcast/leap-academy-with-ilana-golan/id1701718200?i=1000673141824 LEAP Episode with Tom Bilyeu: Tom Bilyeu: https://www.youtube.com/watch?v=rZ4EGDsKudk 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 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/
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  Tom Bilyeu: How I Proved Everyone Wrong and Built a Billion-Dollar Brand | E62 14.07.2026 57мин

  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.comTom’s YouTube: youtube.com/c/TomBilyeuTom’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. Check out our free training today at leapacademy.com/training
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  Amy Porterfield: Why I Quit My Dream Job to Become an Entrepreneur | EP 89 07.07.2026 51мин

  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
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  GaryVee on Building an Unstoppable Mindset | E115 30.06.2026 39мин

  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
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  From Blue Collar Hustles to Billion Dollar Businesses: The Journey of David Royce 23.06.2026 55мин

  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
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  From Skype to Wix: Mark Tluszcz’s Formula for Turning Bold Bets into Billion-Dollar Successes | E163 16.06.2026 1ч 15мин

  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
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  Self-Made Billionaire: How John Paul DeJoria Built Paul Mitchell with $700 | E162 09.06.2026 1ч 9мин

  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
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  Former WWE President: The Hard Decisions That Built a Global Media Business | George Barrios | E161 02.06.2026 1ч 12мин

  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
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  The Lean Startup: Eric Ries Reveals the #1 Mistake New Founders Make | E160 26.05.2026 1ч 16мин

  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
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  Entrepreneur Magazine’s Jason Feifer: How to Build a Career Beyond Your Job Title | E159 19.05.2026 1ч 1мин

  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
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  Tim Draper: How I Spot Billion-Dollar Companies Before Anyone Else | E158 12.05.2026 54мин

  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
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  Kickstarter Co-Founder: How Yancey Strickler Built a $7B Platform That Transformed Crowdfunding | E157 05.05.2026 57мин

  When Yancey Strickler moved to New York, he was broke, freelancing for $50, and chasing a writing career. Little did he know, his gift for building on the internet would soon change the world of crowdfunding. A chance encounter with a friend and a half-baked idea about crowd-funded concert tickets led to the founding of Kickstarter, a platform that has raised over $7 billion for creative projects worldwide. In this episode, Yancey joins Ilana to discuss his journey from freelancing on a shoestring budget to building a billion-dollar platform and what it took to survive the hardest moments. He also explains his bold plan to help artists participate in capitalism. Yancey Strickler is the co-founder and former CEO of Kickstarter, the platform that raised over $7 billion for more than 200,000 creative projects. He now runs Metalabel, a studio building tools for creative cooperation. In this episode, Ilana and Yancey will discuss: (00:00) Introduction  (03:11) From Music Households to Manhattan Bylines (06:28) The Side Project That Changed Everything (13:34) The Ladder Vouch System That Launched Kickstarter (18:57) Why Showing Up as an Open Box Wins Every Room (26:31) The Day Two Projects Hit a Million Dollars at Once (33:40) The New Definition of Work in the Age of AI (36:28) Building the Legal Blueprint for the Artist Economy (43:09) Why the Private Internet Is Where the Real World Lives (49:38) Q&A: How to Open Doors to New Connections Yancey Strickler is a writer, serial entrepreneur, and the co-founder of Kickstarter, the global crowdfunding platform that has raised billions for creative projects.  He's the author of This Could Be Our Future and The Dark Forest Anthology of the Internet and the co-host of the New Creative Era podcast. Before Kickstarter, Yancey was a music critic for outlets like Pitchfork and Spin. Today, he leads two bold projects: A Corp, a legislative effort to provide artists with real economic infrastructure, and DFOs, a platform reimagining the private internet.  Connect with Yancey Yancey’s Website: https://www.ystrickler.com Yancey’s LinkedIn: https://www.linkedin.com/in/yancey-strickler-486b4557/  Yancey’s Instagram: https://www.instagram.com/ystrickler/  Yancey’s X: https://x.com/ystrickler  Resources Mentioned: Yancey’s Books, This Could Be Our Future: A Manifesto for a More Generous World: https://www.amazon.com/This-Could-Our-Future-Manifesto/dp/0525560823  The Dark Forest Anthology of the Internet: https://www.amazon.com/Dark-Forest-Anthology-Internet/dp/B0D14NN1DN  On the Creative Life: Conversations Toward a New Creative Era: https://squad.metalabel.com/onthecreativelife?ref=ystrickler.com&variantId=1  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