Leap Academy with Ilana Golan

Ilana Golan
  • 4.8 (276)
  • Self-Improvement
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The Leap Academy Podcast with Ilana Golan is all about honest and inspiring conversations about what it really takes to leap to bigger things, amazing careers, and craft the life you want. Stories and tips you won't find anywhere else. Ilana speaks with some of the world's most influential people, experts, and thinkers who created incredible careers, massive impact, built a reputation, and an extraordinary life. Together we discover the untold truths, the emotions, and important lessons that enabled them to reinvent themselves & leap.  We take our audience on a journey that will not only inspire but also teach concrete lessons on how to leap careers: fast-track to leadership, jump to entrepreneurship, build a personal brand, portfolio career, and much more. 

  1. 2d ago

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

    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/

  2. Sep 8

    Peloton Co-Founder Tom Cortese: Building an $8.1B Brand & Knowing When to Walk Away | EP171

    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/

  3. Sep 1

    Sir Richard Harpin: How He Turned £50K Into a £4 Billion Business | EP170

    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/

  4. Aug 25

    Lovesac Founder Shawn Nelson: The Entrepreneurial Mindset That Built a Billion-Dollar Brand | EP168

    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/

  5. Aug 18

    Manu Sai Bakshi: From Starting Over to Recruiting Wall Street’s Top Talent | EP167

    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.

  6. Aug 11

    From Losing Everything to Startup of the Year: Ilana Golan’s 5 Shifts to Reinvent Yourself

    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: info@leapacademy.com 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

  7. Aug 4

    Milk Bar CEO Christina Tosi: How a Home Baker Built One of America's Most Beloved Brands | E165

    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/

  8. Jul 28

    Google X's Astro Teller: Why the Biggest Breakthroughs Start with Failure | EP167

    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 Leap Academy Podcast with Ilana Golan is all about honest and inspiring conversations about what it really takes to leap to bigger things, amazing careers, and craft the life you want. Stories and tips you won't find anywhere else. Ilana speaks with some of the world's most influential people, experts, and thinkers who created incredible careers, massive impact, built a reputation, and an extraordinary life. Together we discover the untold truths, the emotions, and important lessons that enabled them to reinvent themselves & leap.  We take our audience on a journey that will not only inspire but also teach concrete lessons on how to leap careers: fast-track to leadership, jump to entrepreneurship, build a personal brand, portfolio career, and much more. 

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