Leap Academy with Ilana Golan

By Ilana GolanBusiness Entrepreneurship Education Self-Improvement Careers

Leap Academy with Ilana Golan episodes

October 13 The Remarkable Story of Stacy Brown-Philpot Outgrowing Her Circumstances | Ep. 174
Founders and executives: Stacy Brown-Philpot traces her path from Detroit to Google, TaskRabbit CEO, and a $172M debut venture fund.

Stacy spent nearly a decade at Google, growing from a 14-person team to leading over 1,000 people in India. She later became CEO of TaskRabbit and sold it to IKEA after launching it into four new countries.

To build Cherryrock Capital, she met 366 investors over two years and closed 83 of them, including Goldman Sachs, JP Morgan, and the Ford Foundation. Her core advice: find the investor who fits your stage, then ask how they will help you win.

LinkedIn: https://www.linkedin.com/in/stacyphilpot/
Cherryrock Capital: https://www.cherryrockcapital.com/

#VentureCapital #CareerAdvice #WomenInVentureCapital #FirstTimeFundManager #StacyBrownPhilpot
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
1 hr 7 min
October 06 The Emotional Story of Carleigh Bodrug’s EXPLOSIVE PlantYou Success | Ep. 173
This episode is dedicated to food creators and entrepreneurs: how Carleigh Bodrug built PlantYou into a bestselling cookbook brand while privately grieving her mother's lung cancer death.

Carleigh grew PlantYou to 13 million followers while filming recipe videos from chemo waiting rooms. She signed her second book deal two weeks before her mom's diagnosis and kept the ordeal off social media.

Her debut cookbook sold out in two days and hit the New York Times list. She also covers the infographic photo formula, her Reels pivot, and why her 225,000-person email list beats any algorithm.

LinkedIn: https://ca.linkedin.com/in/carleigh-bodrug-29193850
Instagram: https://www.instagram.com/plantyou/
PlantYou: https://plantyou.com/about/
Books: https://www.hachettebookgroup.com/contributor/carleigh-bodrug/

#PlantYou #FoodEntrepreneur #PlantBasedCooking #BestsellingCookbook #CarleighBodrug
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
51 min
September 29 Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | EP53
We’re bringing back one of our favorite conversations from the Leap Academy podcast with Shopify President Harley Finkelstein. Harley Finkelstein didn’t set out to be an entrepreneur. He had no choice. With his father out of the picture, he had to pay for university and support his mother and sisters. So, he turned to his go-to problem-solving tool: entrepreneurship. Starting a t-shirt business changed his life, eventually leading him to Shopify, where he became one of their first merchants and later, its president. In this episode, Harley shares his incredible journey, highlighting key lessons on how entrepreneurship can solve real-life problems and the power of adapting quickly in a fast-changing world.Harley Finkelstein is the President of Shopify. He is also an entrepreneur, lawyer, and investor. He is one of the “Dragons” on CBC’s Next Gen Den and has been recognized among Canada’s Top 40 Under 40 and Fortune’s 40 Under 40. In this episode, Ilana and Harley will discuss: 00:00 Introduction 01:11 Early Entrepreneurial Ventures 07:44 College Years and T-Shirt Business 14:14 Transition to Shopify 19:39 Challenges and Growth at Shopify 45:56 COVID-19 Impact and Adaptation 49:31 Black Friday and Cyber Monday Insights 53:27 Mentorship and Personal Growth 56:31 Encouragement for Aspiring Entrepreneurs 59:57 Conclusion and Final Thoughts Harley Finkelstein is an entrepreneur, lawyer, and President of Shopify. He is an advisor to Felicis Ventures and a notable investor. He has been recognized as Canadian Angel Investor of the Year and among Canada's Top 40 Under 40. Connect with Harley: Harley’s Website: harleyf.com Harley’s LinkedIn: Harley Finkelstein on LinkedIn Harley’s Twitter: @harleyf 📲 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/
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
54 min
September 22 Neil Patel: From Crushing Failures to Building a Global Marketing Empire | EP62
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
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
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
44 min
September 15 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/
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
1 hr 3 min
September 08 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/
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
1 hr 25 min
September 01 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/
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
54 min
August 25 Lovesac Founder Shawn Nelson: The Entrepreneurial Mindset That Built a Billion-Dollar Brand | EP169
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/
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
1 hr 3 min
August 18 Manu Sai Bakshi: From Starting Over to Recruiting Wall Street’s Top Talent | EP168
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.
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
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🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
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📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
1 hr 2 min
August 11 From Losing Everything to Startup of the Year: Ilana Golan’s 5 Shifts to Reinvent Yourself | E167
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
Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.

🧠 Start with a free strategy call with Ilana.

🎓 Watch the free masterclass on building multiple income streams.

👇 Like what you hear? Comment below and let us know what resonated!
---------------
🎧 PODCAST | Leap Academy with Ilana Golan
Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
▶️ https://www.leapacademy.com/podcast
---------------

📲 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/

🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek
28 min

About Leap Academy with Ilana Golan

From the publisher's feed

Leap Academy with Ilana Golan is a podcast for ambitious professionals who know they're capable of more and want their next move to be bigger, whether that's a C-suite role, a board seat, an…