We’re bringing back one of our favorite conversations from the Leap Academy podcast with digital marketing expert and entrepreneur Neil Patel.

Neil’s story shows how hard work, persistence, and learning from failure lead to success. As a teenager, he started businesses, including building websites, but struggled with ineffective marketing agencies. This pushed him to learn digital marketing, and by 16, he helped a client make $20M, marking the start of his career. After facing challenges with his earlier ventures, he shifted from starting businesses to acquiring and turning underperforming ones into successes. Now, as the founder of NP Digital, he runs a global marketing company that helps businesses grow. In this episode, Neil talks with Ilana about his journey, the strategies behind his success, and how businesses can overcome challenges and scale in today’s competitive market.

Neil Patel is a New York Times bestselling author, digital marketing expert, and the founder of one of the top 100 most brilliant companies, according to Entrepreneur Magazine. With over 15 years of experience, Neil has been instrumental in helping businesses grow their online presence and revenue.

In this episode, Ilana and Neil will discuss:

(00:00) Introduction

(01:11) The Power of Hard Work Over Privilege

(01:39) From Teenage Hustle to Launching His First Website

(08:01) Learning Digital Marketing After Agency Failures

(08:55) Helping a Client Reach $20M in Revenue at Age 16

(10:17) Attending College Due to Family Expectations

(11:55) How Experimentation Reveals Your True Strengths

(14:26) Lessons from Surviving Legal Battles at Kissmetrics

(19:53) Businesses That Found Success Despite Their Flaws

(22:35) Balancing Personal and Corporate Branding for Success

(25:24) Shifting from Building to Acquiring Businesses

(27:10) Neil’s Strategy for Improving Acquired Businesses

(31:15) Why “Renting Your Dreams” Can Lead to Future Success

(33:29) How Consistency and Networking Create Opportunities

(35:48) Empowering and Trusting Your Team for Results

(37:44) Hiring Experts to Reduce Risk and Drive Growth

(40:57) Neil Patel's Digital Marketing Services

Neil Patel is a New York Times bestselling author, digital marketing expert, and the founder of one of the top 100 most brilliant companies, according to Entrepreneur Magazine. Recognized as a top influencer by The Wall Street Journal and one of Forbes' top marketers, Neil has helped companies like Amazon, Microsoft, and Google grow through marketing. He is also the co-founder of NP Digital, a leading marketing agency. With over 15 years of experience, Neil has been instrumental in helping businesses grow their online presence and revenue.

Connect with Neil:

Neil’s Website: https://neilpatel.com/

Neil’s LinkedIn: https://www.linkedin.com/in/neilkpatel/

Neil’s YouTube: https://www.youtube.com/neilpatel

Resources Mentioned:

NP Digital: https://npdigital.com/

Neil’s Book, Hustle: The Power to Charge Your Life with Money, Meaning, and Momentum: https://www.amazon.com/Hustle-Power-Charge-Meaning-Momentum/dp/1623367166

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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:

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LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/

Instagram ▶️ https://www.instagram.com/ilanagolanleap

Website ▶️ https://www.leapacademy.com/

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:

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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.

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

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.

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

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:

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

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 Profile
https://x.company/astro-teller

Astro Teller on LinkedIn
https://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

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Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy

LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/

Instagram ▶️ https://www.instagram.com/ilanagolanleap

Website ▶️ https://www.leapacademy.com/

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/