Leap Academy with Ilana Golan

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

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/

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/