Leap Academy with Ilana Golan

Tim Draper didn’t become a legendary investor with billions in his account overnight; he started by taking a $6 million loan to launch his first venture fund, knowing failure was a real possibility. That decision didn’t just shape his career; it laid the foundation for backing some of the biggest companies in the world, including Hotmail, Skype, Tesla, and more. In this episode, Tim joins Ilana to break down how to spot world-changing ideas before they make sense, why most people miss their biggest opportunities, and how listening to your gut can be more powerful than logic alone. He shares the lessons behind massive wins like Hotmail, painful misses like Netflix, and the mindset required to navigate uncertainty, fear, and reinvention.

Tim Draper is a third-generation venture capitalist, founder of Draper University, and one of Silicon Valley's most legendary investors. He is a lifelong advocate for entrepreneurship, innovation, and the next generation of world-changing founders.

In this episode, Ilana and Tim will discuss:

(00:00) Introduction 

(04:11) Early Lessons on Money, Risk, and Capitalism

(08:43) Leaving Home at 13 and Learning to Figure It Out

(11:48) Venture Capital Roots and Family Background

(14:17) Taking a $6 Million Loan and Betting on Himself

(17:14) Spotting Billion-Dollar Companies Before Anyone Else

(20:11) The Viral Growth Strategy Behind Hotmail

(23:26) How Skype Changed Global Communication Forever

(29:18) Navigating the Dot-Com Crash

(34:13) Will AI and Crypto Follow the Same Boom Cycle?

(35:55) The Power of Listening to Your Gut as an Entrepreneur

(46:59) Q&A: How Do I Know What to Invest In? 

Tim Draper is a third-generation venture capitalist and founder of Draper University. He backed world-changing companies, including Hotmail, Skype, Tesla, SpaceX, Coinbase, and Robinhood. Known for spotting transformative trends before the mainstream, he's also a passionate advocate for entrepreneurship education, cryptocurrency, and celebrating innovation. His show Meet the Drapers reaches roughly 300 million people globally.

Connect with Tim

Tim’s Website: https://timothydraper.com/ 

Tim’s LinkedIn: https://www.linkedin.com/in/timothydraper/ 

Tim’s Instagram: https://www.instagram.com/timdraper/ 

Resources Mentioned:

Tim’s Book,

How to be the Startup Hero - A Guide and Textbook for Entrepreneurs and Aspiring Entrepreneurs: https://www.amazon.com/How-Startup-Hero-Textbook-Entrepreneurs/dp/1973585340/ref=cm_cr_arp_d_product_top?ie=UTF8

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

When Yancey Strickler moved to New York, he was broke, freelancing for $50, and chasing a writing career. Little did he know, his gift for building on the internet would soon change the world of crowdfunding. A chance encounter with a friend and a half-baked idea about crowd-funded concert tickets led to the founding of Kickstarter, a platform that has raised over $7 billion for creative projects worldwide. In this episode, Yancey joins Ilana to discuss his journey from freelancing on a shoestring budget to building a billion-dollar platform and what it took to survive the hardest moments. He also explains his bold plan to help artists participate in capitalism.

Yancey Strickler is the co-founder and former CEO of Kickstarter, the platform that raised over $7 billion for more than 200,000 creative projects. He now runs Metalabel, a studio building tools for creative cooperation.

In this episode, Ilana and Yancey will discuss:

(00:00) Introduction 

(03:11) From Music Households to Manhattan Bylines

(06:28) The Side Project That Changed Everything

(13:34) The Ladder Vouch System That Launched Kickstarter

(18:57) Why Showing Up as an Open Box Wins Every Room

(26:31) The Day Two Projects Hit a Million Dollars at Once

(33:40) The New Definition of Work in the Age of AI

(36:28) Building the Legal Blueprint for the Artist Economy

(43:09) Why the Private Internet Is Where the Real World Lives

(49:38) Q&A: How to Open Doors to New Connections

Yancey Strickler is a writer, serial entrepreneur, and the co-founder of Kickstarter, the global crowdfunding platform that has raised billions for creative projects.  He's the author of This Could Be Our Future and The Dark Forest Anthology of the Internet and the co-host of the New Creative Era podcast. Before Kickstarter, Yancey was a music critic for outlets like Pitchfork and Spin. Today, he leads two bold projects: A Corp, a legislative effort to provide artists with real economic infrastructure, and DFOs, a platform reimagining the private internet. 

Connect with Yancey

Yancey’s Website: https://www.ystrickler.com

Yancey’s LinkedIn: https://www.linkedin.com/in/yancey-strickler-486b4557/ 

Yancey’s Instagram: https://www.instagram.com/ystrickler/ 

Yancey’s X: https://x.com/ystrickler 

Resources Mentioned:

Yancey’s Books,

This Could Be Our Future: A Manifesto for a More Generous World:

https://www.amazon.com/This-Could-Our-Future-Manifesto/dp/0525560823 

The Dark Forest Anthology of the Internet:

https://www.amazon.com/Dark-Forest-Anthology-Internet/dp/B0D14NN1DN 

On the Creative Life: Conversations Toward a New Creative Era:

https://squad.metalabel.com/onthecreativelife?ref=ystrickler.com&variantId=1 

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

Elena Cardone’s life changed the day she watched her best friend die in a house fire. That trauma sent her spiraling into a decade of drugs and alcohol, and as more friends died in the years that followed, she believed she was next. Until one night, a dream forced her to confront the truth: she wasn’t honoring her friend’s life; she was wasting her own. That moment became the turning point that set her on a path to transforming her life and building a $5 billion empire. In this episode, Elena shares how she broke free from destructive patterns and the mindset shifts that transformed her marriage, career, and financial future.

Elena Cardone is an entrepreneur, bestselling author, speaker, and real estate investor who has built a $5 billion portfolio alongside her husband, Grant Cardone. She is the co-founder of Cardone Capital, Cardone Foundation, and Cardone Mortgage.

In this episode, Ilana and Elena will discuss:

(00:00) Introduction 

(05:39) The House Fire That Changed Everything

(08:52) How Your Mind Works Against You to Self-Sabotage

(11:21) Moving to Hollywood and Discovering Its Dark Sides

(15:56) How Trauma Almost Cost Her the Right Man

(24:15) The 2008 Crisis and a Marriage Breaking Point

(27:25) How a Nightly Game Built a Billion-Dollar Mindset

(35:41) The Hidden Cost of Believing Money Is Evil

(41:40) Why Great People Attack Your Weaknesses

(46:38) Elena’s Plan to Build Global Influence

(51:29) Q&A: How Do You Get Paid to Speak?

Elena Cardone is an entrepreneur, former actress, podcast host, and the bestselling author of Build an Empire. She is a licensed realtor leading a 500-agent organization with eXp Realty, and has built a $5 billion portfolio alongside her husband, Grant Cardone. Elena is also the co-founder of both the Grant Cardone Foundation, which helps underserved youth understand finance and business, and Cardone Mortgage, which makes homeownership more accessible across all 50 states. 

Connect with Elena:

Elena’s Website: https://elenacardone.com

Elena’s LinkedIn: https://www.linkedin.com/in/elenacardone/

Elena’s Instagram: https://www.instagram.com/elenacardone/ 

Resources Mentioned:

Elena’s Book, Build an Empire: How to Have It All:

https://www.amazon.com/Build-Empire-How-have-All-ebook/dp/B09RGHGQ4K 

Dianetics: The Modern Science of Mental Health by L. Ron Hubbard: https://www.amazon.com/Dianetics-Modern-Science-Mental-Health/dp/B001EPO4Z2

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

Ra’anan Cohen walked into the tech world with no fancy degree and no startup pedigree; just a phone call from a friend and the promise of free food and a gym membership. From day one, he felt like an outsider, constantly battling imposter syndrome. Yet, he stuck with it, learned the ropes of the startup world, and ultimately founded a billion-dollar company. In this episode, Ra’anan joins Ilana to share his wild 15-year ride: a public company on NASDAQ, a unicorn valued at $1 billion, and a board that tried to fire him at his peak. He reveals everything the startup world doesn't want you to know about the real cost of chasing unicorns.

Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was also the founder and CEO of MobileMax, which went public on NASDAQ.

In this episode, Ilana and Ra’anan will discuss:

(00:00) Introduction 

(04:30) The Biggest False Beliefs On Entrepreneurship

(06:38) The Impact of Imposter Syndrome on Ra'anan's Career

(09:16) Quitting a Stable Job to Start a Company

(12:09) Raising Capital with No Credentials

(15:34) The $10M Mistake That Cost Him Everything

(18:55) How a Pizza Night Sparked a Billion-Dollar Idea

(24:35) Raising Capital the Second Time: The Stealth Mode Strategy

(28:47) Different Types of Modern Investors

(32:52) Why Startups Are Marathons, Not Rollercoasters

(43:43) When to Make Life-Changing Decisions (and When Not To)

(45:39) Redefining Success: The Multi-Bucket Life Philosophy

(53:36) Q&A: Handling Rejection Without Losing Your Spark

Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was the founder and CEO of MobileMax, where he led the company to multimillion-dollar international sales and an IPO. Ra'anan is also the author of Confessions of a Unicorn Founder, a national bestseller in Israel, which is currently being adapted into a TV series.

Connect with Ra’anan:

Ra’anan’s Website: https://www.raanancohen.com 

Ra’anan’s LinkedIn: linkedin.com/in/raananc 

Resources Mentioned:

Ra’anan’s Book,

Confessions of a Unicorn Founder: Obsession, Greed, and the Brutal Truth Behind Chasing the Startup Dream: https://www.raanancohen.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

When Kim Perell was fired, she had to fire all her friends on the same day. The company she thought would make her a millionaire had just gone bankrupt, leaving her with no income or backup plan. Instead of giving up, she took a $10,000 loan from her grandmother to start her first company from her kitchen table. That bet led to a $20 million exit and eventually, a $235 million company. In this episode, Kim joins Ilana to share how to turn setbacks and mistakes into million-dollar breakthroughs and how to overcome the limiting beliefs holding you back. She also reveals the four pillars that helped her achieve success without burning out.

Kim Perell is a 9x founder, 3x bestselling author, and investor in 100+ companies. Kim became a multi-millionaire by the time she was 30, and sold her last company for $235 million to Singtel, while simultaneously running multi-million-dollar companies.

In this episode, Ilana and Kim will discuss:

(00:00) Introduction 

(04:08) Growing Up in the Shadow of Her Twin Sister

(07:07) Learning Risk and Failure from Entrepreneur Parents

(09:46) How Getting Fired Led to a Career Pivot

(13:31) Her Grandma’s Life-Changing $10K Loan

(16:37) Using The 70% Rule to Make Business Decisions

(18:48) The Four Pillars of Business Success

(23:50) Selling Her Business for $20 Million

(28:02) Building a Money Mindset 

(30:59) The Dangers of Failing to Pivot Or Make Mistakes

(40:13) Teaching Your Children Resilience

(45:01) Q&A: How to Chase Success Despite Fear

Kim Perell is a 9-time founder, 3-time bestselling author, top keynote speaker, and investor in over 100 companies. Her book, Mistakes That Made Me a Millionaire, offers a transformative guide to turning setbacks into million-dollar opportunities. An award-winning entrepreneur, Kim has appeared on major platforms and serves as a judge for Entrepreneur Magazine’s Elevator Pitch. She is dedicated to empowering the next generation of business leaders for success.

Connect with Kim:

Kim’s Website: https://kimperell.com/ 

Kim’s LinkedIn: https://www.linkedin.com/in/kimperell/ 

Kim’s Instagram: https://www.instagram.com/kimperell/ 

Resources Mentioned:

Kim’s Book,

Mistakes that Made Me a Millionaire: How to Transform Setbacks into Extraordinary Success: https://www.amazon.com/dp/1637747128 

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