Leap Academy with Ilana Golan

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/

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/

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/

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: 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