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by Ilana Golan
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- 1 weeks ago54 min
Tim Draper: How I Spot Billion-Dollar Companies Before Anyone Else | E158
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: Introduction Early Lessons on Money, Risk, and Capitalism Leaving Home at 13 and Learning to Figure It Out Venture Capital Roots and Family Background Taking a $6 Million Loan and Betting on Himself Spotting Billion-Dollar Companies Before Anyone Else The Viral Growth Strategy Behind Hotmail How Skype Changed Global Communication Forever Navigating the Dot-Com Crash Will AI and Crypto Follow the Same Boom Cycle? The Power of Listening to Your Gut as an Entrepreneur 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
- 2 weeks ago57 min
Kickstarter Co-Founder: How Yancey Strickler Built a $7B Platform That Transformed Crowdfunding | E157
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: Introduction From Music Households to Manhattan Bylines The Side Project That Changed Everything The Ladder Vouch System That Launched Kickstarter Why Showing Up as an Open Box Wins Every Room The Day Two Projects Hit a Million Dollars at Once The New Definition of Work in the Age of AI Building the Legal Blueprint for the Artist Economy Why the Private Internet Is Where the Real World Lives 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
- 3 weeks ago1h 2m
Elena Cardone: Overcoming Trauma and Loss to Build a $5 Billion Business | E156
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: Introduction The House Fire That Changed Everything How Your Mind Works Against You to Self-Sabotage Moving to Hollywood and Discovering Its Dark Sides How Trauma Almost Cost Her the Right Man The 2008 Crisis and a Marriage Breaking Point How a Nightly Game Built a Billion-Dollar Mindset The Hidden Cost of Believing Money Is Evil Why Great People Attack Your Weaknesses Elena’s Plan to Build Global Influence 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
- 3 weeks ago1h 4m
The Dark Truth About Venture Capital: Confessions of a Unicorn Founder | Ra'anan Cohen | E155
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: Introduction The Biggest False Beliefs On Entrepreneurship The Impact of Imposter Syndrome on Ra'anan's Career Quitting a Stable Job to Start a Company Raising Capital with No Credentials The $10M Mistake That Cost Him Everything How a Pizza Night Sparked a Billion-Dollar Idea Raising Capital the Second Time: The Stealth Mode Strategy Different Types of Modern Investors Why Startups Are Marathons, Not Rollercoasters When to Make Life-Changing Decisions (and When Not To) Redefining Success: The Multi-Bucket Life Philosophy 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
- Apr 14, 202656 min
9x Founder Kim Perell: How I Turned a $10K Loan Into a $235M Company | E154
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: Introduction Growing Up in the Shadow of Her Twin Sister Learning Risk and Failure from Entrepreneur Parents How Getting Fired Led to a Career Pivot Her Grandma’s Life-Changing $10K Loan Using The 70% Rule to Make Business Decisions The Four Pillars of Business Success Selling Her Business for $20 Million Building a Money Mindset The Dangers of Failing to Pivot Or Make Mistakes Teaching Your Children Resilience 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
- Apr 7, 20261h 3m
How Basecamp's CEO Lost 30% of His Team, Faced Backlash, and Came Back Stronger | Jason Fried | E153
Jason Fried didn’t follow the startup rules most founders swear by. He rejected venture capital, refused to chase growth at all costs, and chose to stay small on purpose. What started as a scrappy web design agency turned into Basecamp, a multi-million-dollar business built on profitability, simplicity, and conviction. In this episode, Jason joins Ilana to challenge everything you think you know about scaling a business. He also opens up about how a single leadership decision caused 30% of his company to quit overnight, and how staying principled ultimately made the company stronger. Jason Fried is the co-founder and CEO of 37signals, the company behind Basecamp and HEY. For over 27 years, he has grown Basecamp into a multi-million dollar business without ever taking venture capital or chasing aggressive growth targets. In this episode, Ilana and Jason will discuss: Introduction Lessons from Selling Stereo Equipment as a Kid Starting 37signals from Scratch Pivoting to Software Through Basecamp The Perks of Being a Small Company The Policy That Made 30% of the Company Quit Surviving the Backlash and Rebuilding the Team Building Thicker Skin as a Leader How to Incorporate AI Without Getting Carried Away How Basecamp Is Reinventing Itself with Version 5 Why Jason Won’t Advise His Younger Self Q&A: How to Decide Your Next Career Move Jason Fried is a co-founder and CEO of 37signals, the makers of Basecamp. He is a bestselling author of Rework and It Doesn’t Have to Be Crazy at Work. Known for his contrarian approach to entrepreneurship, Jason emphasizes simplicity, profitability, and long-term thinking. For over 27 years, he has grown Basecamp into a multi-million dollar, fully profitable business without ever taking venture capital or chasing aggressive growth targets. Connect with Jason: LinkedIn: linkedin.com/in/jason-fried X: https://x.com/jasonfried Resources Mentioned: Jason’s Books: Rework: https://www.amazon.com/Rework-Jason-Fried/dp/0307463745 It Doesn't Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780 37signals’ Website: https://37signals.com Basecamp’s Website: https://basecamp.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
- Mar 31, 20261h 1m
Qualcomm CMO Don McGuire: How to Stay Relevant, Resilient, and Ready for Change | E152
Don McGuire did not build his career through a straight line. He lost elections as a kid, moved every few years, started over again and again, and had to learn resilience early. After graduating from college, he was still unsure what to do, but a leap into the early cellular industry launched a career that would take him from sales to marketing and ultimately, the CMO seat at Qualcomm. In this episode, Don chats with Ilana about how to stay in control of your career in a world changing at the speed of AI. He shares why resilience matters more than ever, how to spot the right time to leap, and what it takes to stay relevant in a crowded job market. Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, with over 25 years of experience across service providers, semiconductors, and technology marketing. In 2025, he was named one of Forbes’ World’s Most Influential CMOs. In this episode, Ilana and Don will discuss: Introduction The Early Experiences That Built Don’s Resilience His Love for Marketing and Journey Into Tech The Transition From Sales to Marketing Why You Must Stay in Control of Your Own Destiny Startup Lessons, Consulting, and Selling Yourself Knowing When It Was Time to Leap Back Into Corporate The Crisis That Forced Qualcomm to Tell Its Story The One Trait Gen Z and Gen Alpha Need Most How to Stand Out in an AI-Driven Job Market Why Portfolio Careers and Side Skills Matter What Excites Don Most About Qualcomm’s Future Q&A: How to Break the “I Can’t Get a Job” Mindset Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, where he oversees global marketing as the company expands beyond mobile into automotive, computing, AI, and other growth areas. Before joining Qualcomm, he held senior leadership roles at Intel and other major wireless and technology companies. In 2025, he was named one of Forbes’ World’s Most Influential CMOs. Connect with Don: Don’s LinkedIn: linkedin.com/in/donnymac Resources Mentioned: Qualcomm: https://www.qualcomm.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
- Mar 24, 202652 min
What It Takes to Scale a Company Without Breaking It | Mike Seckler, Justworks CEO | E151
In the late 1990s, Mike Seckler started a company with little experience, plenty of curiosity, and no idea what was coming. Then the dot-com bubble burst. Almost overnight, capital disappeared. Companies collapsed. And Mike faced one of the hardest decisions of his career: laying off a third of his team to keep the company alive. That moment changed how he builds companies and leads today as CEO of Justworks. In this episode, Mike joins Ilana to share the real lessons behind building and scaling through uncertainty and how founders can avoid the leadership mistakes that derail most companies. Mike Seckler is the President and CEO of Justworks, an HR platform helping over 14,000 small businesses manage payroll, benefits, compliance, and workforce management. In this episode, Ilana and Mike will discuss: Introduction From History and Geology Student to Entrepreneur The Early Days of Founding Employease Navigating the Dot Com Crash as a Founder Selling to ADP and Starting a New Venture Joining Justworks: From Board Member to COO Lessons from Transitioning to Justworks’ CEO The Biggest Blindspots for Small Businesses How to Beat Founder Loneliness Adapting to a Rapidly Evolving Market Justworks: Empowering Small Businesses for Growth Review and Q&A: BREAD Productivity Framework Mike Seckler is a serial entrepreneur who has built and scaled multiple companies over the past two decades. Before joining Justworks, he co-founded Employease, an HR outsourcing firm that was eventually acquired by ADP, and later co-founded Euclidean Technologies, a company applying machine learning to public market investing. Today, as CEO of Justworks, Mike leads a platform serving thousands of small businesses and helping founders navigate the complexities of building and scaling their teams. Connect with Mike: Mike’s LinkedIn: linkedin.com/in/mikeseckler Resources Mentioned: Justworks Website: https://www.justworks.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
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About Leap Academy with Ilana Golan
The Leap Academy Podcast with Ilana Golan is all about honest and inspiring conversations about what it really takes to leap to bigger things, amazing careers, and craft the life you want.Stories and tips you won't find anywhere else.Ilana speaks with some of the world's most influential people, experts, and thinkers who created incredible careers, massive impact, built a reputation, and an extraordinary life.Together we discover the untold truths, the emotions, and important lessons that enabled them to reinvent themselves & leap. We take our audience on a journey that will not only inspire but also teach concrete lessons on how to leap careers: fast-track to leadership, jump to entrepreneurship, build a personal brand, portfolio career, and much more.
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