The Dark Truth About Venture Capital: Confessions of a Unicorn Founder | Ra'anan Cohen | E155

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

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: (00:00) Introduction  (03:18) Lessons from Selling Stereo Equipment as a Kid (06:58) Starting 37signals from Scratch (14:13) Pivoting to Software Through Basecamp   (16:41) The Perks of Being a Small Company (27:24) The Policy That Made 30% of the Company Quit  (31:45) Surviving the Backlash and Rebuilding the Team (39:21) Building Thicker Skin as a Leader (42:43) How to Incorporate AI Without Getting Carried Away (45:15) How Basecamp Is Reinventing Itself with Version 5 (48:56) Why Jason Won’t Advise His Younger Self (54:07) 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

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: (00:00) Introduction (03:14) The Early Experiences That Built Don’s Resilience (10:46) His Love for Marketing and Journey Into Tech (18:00) The Transition From Sales to Marketing (20:18) Why You Must Stay in Control of Your Own Destiny (23:25) Startup Lessons, Consulting, and Selling Yourself (27:43) Knowing When It Was Time to Leap Back Into Corporate (31:45) The Crisis That Forced Qualcomm to Tell Its Story (38:16) The One Trait Gen Z and Gen Alpha Need Most (40:33) How to Stand Out in an AI-Driven Job Market (45:02) Why Portfolio Careers and Side Skills Matter (48:03) What Excites Don Most About Qualcomm’s Future (53:05) 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

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: (00:00) Introduction  (02:42) From History and Geology Student to Entrepreneur (07:05) The Early Days of Founding Employease (09:08) Navigating the Dot Com Crash as a Founder (14:53) Selling to ADP and Starting a New Venture (17:23) Joining Justworks: From Board Member to COO (24:37) Lessons from Transitioning to Justworks’ CEO (26:00) The Biggest Blindspots for Small Businesses (31:58) How to Beat Founder Loneliness (36:34) Adapting to a Rapidly Evolving Market (42:03) Justworks: Empowering Small Businesses for Growth (44:49) 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

When Bill Gurley wanted to break into Wall Street, there were no job postings waiting for him. So he flew to New York, knocked on doors, and asked strangers for meetings. That hustle launched a career that would eventually take him to Silicon Valley, where he became one of the most respected venture capitalists in tech. In this episode, Bill joins Ilana to reveal the unconventional lessons that shaped his journey. From chasing curiosity to designing your own career path, he explains how anyone can create opportunities, stand out in a crowded field, and build a career that actually excites them. Bill Gurley is a Silicon Valley venture capitalist and a longtime partner at Benchmark Capital, a Silicon Valley venture capital firm. He has invested in and served on the boards of major companies, including Uber, OpenTable, Zillow, Nextdoor, and Stitch Fix. In this episode, Ilana and Bill will discuss: (00:00) Introduction  (03:14) Where Bill Gurley’s Tech Curiosity Began (05:09) Transitioning from Engineering to Finance (08:25) Breaking Into Wall Street Without a Job Posting (14:24) The Question That Made Him Quit Wall Street (19:59) Making a Pivot to Venture Capital (24:41) The Best Way to Get Into Venture Capital (26:50) How to Know If You’re in the Right Career (30:30) The Role of Experimentation in Career Growth (33:20) How to Stand Out in a Competitive Job Market (37:29) Why Location Can Make or Break Your Career (40:50) Breaking Free From the “Safe Career” Pressure (48:30) The 5–5–5 Rule for Career Experiments Bill Gurley is a venture capitalist, technology investor, and general partner at Benchmark Capital, best known for his early investment in companies like Uber. Before venture capital, he worked as an engineer at Compaq and later as a Wall Street technology analyst. Throughout his career, Bill has been known for identifying transformative companies early and for his widely read blog Above the Cloud. His new book, Running Down a Dream, offers a practical guide to building a fulfilling career Connect with Bill: Bill’s X (Twitter): x.com/bgurley  Bill’s Website: abovethecrowd.com  Resources Mentioned: Bill’s Book, Runnin' Down a Dream: How to Thrive in a Career You Actually Love: https://www.amazon.com/dp/0593799666  One Up On Wall Street: How to Use What You Already Know to Make Money in the Market by Peter Lynch: https://www.amazon.com/dp/0743200403  Range: Why Generalists Triumph in a Specialized World by David Epstein: https://www.amazon.com/dp/0735214484  Greenlights by Matthew McConaughey: https://www.amazon.com/dp/0593139135  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

Nir Eyal grew up clinically obese, ashamed of his body, and convinced that food controlled him. He tried every diet: low-fat, keto, vegetarian, and intermittent fasting. Each one worked until it didn’t. What finally changed his life wasn’t a meal plan; it was his belief. When he believed a plan would work, it worked. When that belief cracked, the weight returned. And he realized this pattern doesn’t just apply to weight; it shows up in every area of life. In this episode, Nir joins Ilana to reveal the hidden force behind your success or stagnation. He unpacks the science of belief, how it shapes what you see, feel, and do, and the practical framework to break limiting beliefs before they break you. Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer known for his work on habit formation, psychology, and human behavior. As an entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!. In this episode, Ilana and Nir will discuss: (00:00) Introduction  (03:14) Childhood and Weight Loss Struggles (07:34) Why Affirmations and Vision Boards Don’t Work (09:18) Facts vs Faith vs Beliefs (10:59) His Journey from Founder to Bestselling Author (16:01) The Power of Belief in Success and Failure  (24:49) The ‘Messy Middle’: Knowing When to Persist vs Quit (32:06) Skills Gap vs Belief Gap in Leaders and Teams (34:0) The Four Questions to Rewire a Limiting Belief (46:51) Q&A: Crafting a Memorable Pitch Story Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer. He is the author of Hooked and Indistractable, which have sold over one million copies worldwide and been translated into more than 30 languages. His latest book, Beyond Belief, explores how hidden beliefs shape our limitations and how to replace them to unlock personal and professional growth. An entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!. Connect with Nir: Nir’s Website: http://nirandfar.com Nir’s Instagram: instagram.com/neyal99 Nir’s LinkedIn: linkedin.com/in/nireyal Resources Mentioned: Nir’s Books: Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Breakthrough Results: https://www.amazon.com/dp/0593852036 Indistractable: How to Control Your Attention and Choose Your Life: https://www.amazon.com/dp/194883653X Hooked: How to Build Habit-Forming Products: https://www.amazon.com/dp/1591847788 Nir’s 30-Day Belief Transformation Journal: nirandfar.com/beyond-belief 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

Dr. Amy Shah did everything she was supposed to do. Ivy League education. Elite medical training. Multiple board certifications. On paper, her life looked like a success. But behind the accolades, she was exhausted, disconnected, and running on stress. Then a near-fatal car accident forced her to confront a hard truth. The life she built was slowly breaking her body and mind. In this episode, Amy joins Ilana to share how a personal health crisis became the catalyst for a complete reinvention. She opens up about leaving the traditional medical path without burning the boats, building a science-backed wellness platform, and why women are being failed by modern healthcare. Dr. Amy Shah is a double board-certified physician and nutrition specialist. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine. In this episode, Ilana and Dr. Amy will discuss: (00:00) Introduction  (03:30) How a Near-Fatal Accident Became a Wake-Up Call (09:51) From Traditional Medical Path to a Wellness Brand (13:08) Building a Personal Brand Despite Pushback (17:13) The Power of Having a Supportive Network (21:47) How Dr. Amy Built a Powerful Portfolio Career (23:51) Understanding Women's Health: The 30-30-3 Framework (26:41) The Science of Probiotics and Gut Health (30:24) The 4-3-2-1 Movement Framework for Peak Health (37:32) Managing Stress and Cortisol Levels (43:42) Building a Personal Brand and Finding Your Path (47:17) Her Immigrant Roots and Its Impact (51:44) Review and Q&A: Beating Ageism in Your Career Journey Dr. Amy Shah is a double board-certified physician and nutrition specialist. She is the bestselling author of I’m So Effing Hungry and I’m So Effing Tired. Her latest book, Hormone Havoc, offers a science-backed guide to navigating the complexities of perimenopause and menopause. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine. Connect with Dr. Amy: Dr. Amy’s Website: https://amymdwellness.com  Dr. Amy’s Instagram: instagram.com/dramyshah  Resources Mentioned: Dr. Amy’s Books,  Hormone Havoc: A Science-Backed Protocol for Perimenopause and Menopause: Sleep Better. Think Better. Feel Better: https://www.amazon.com/dp/0063420856  I'm So Effing Hungry: Why We Crave What We Crave – and What to Do About It: https://www.amazon.com/dp/0063285118  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

The world tells leaders they must be everything: visionary, innovator, operator, executor. Patrick Lencioni tried, but it nearly crushed him. He wasn’t exhausted from effort; he was exhausted from misalignment. He discovered what most high performers never admit: trying to be everything is the fastest path to burnout. That insight became The Six Types of Working Genius, a simple framework reshaping how teams work by aligning people with the work that gives them energy. In this episode, Patrick joins Ilana to break down the Six Types of Working Genius and show how aligning your strengths can transform your career, your team, and your fulfillment at work. Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity. In this episode, Ilana and Patrick will discuss: (00:00) Introduction  (02:46) Patrick’s Early Life and Career Beginnings (08:31) Joining Oracle and Pitching Ideas (12:36) Turning Down a Job Offer from Steve Jobs (15:40) The Decision to Start the Table Group (20:18) Navigating the Hard Moments in Entrepreneurship (23:30) Short Attention Spans as a Bestselling Author  (28:06) The Birth and Impact of Working Genius  (34:48) Applying Working Genius to Career Choices (41:05) W-I-D-G-E-T: The Six Types of Working Genius (54:57) Healing Childhood Scars and Understanding Self (59:15) Q&A: The Keys to Building a Portfolio Career Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. He has written 13 books with over 7 million copies sold worldwide, including The Five Dysfunctions of a Team. He is also the creator of The 6 Types of Working Genius, a framework that helps teams identify the work that energizes them and improves performance. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity. Connect with Patrick: Patrick’s LinkedIn: linkedin.com/in/patrick-lencioni-orghealth Patrick’s Instagram: instagram.com/patricklencioniofficial Resources Mentioned: Patrick’s Books:  The Five Temptations of a CEO: https://www.amazon.com/dp/B0062OAEWM The Five Dysfunctions of a Team: https://www.amazon.com/dp/0787960756 The 6 Types of Working Genius: A Better Way to Understand Your Gifts, Your Frustrations, and Your Team: https://www.amazon.com/dp/B09XGPCM36 Working Genius Website: https://www.workinggenius.com Take the Working Genius Assessment: https://www.workinggenius.com/about/assessment  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon