Episode 486: Mark Cuban: Why Most Entrepreneurs Hire Wrong (And Go Broke)

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September 19, 2025 • 30 mins

Listen to the full episode: https://www.youtube.com/watch?v=ThY-UBFtGK8 Even billionaires struggle with self-doubt. In this Fitness Friday excerpt from my conversation with Mark Cuban, he opens up about still feeling intimidated in rooms full of domain experts, why he believes most entrepreneurs hire the wrong people at the wrong time, and his surprising take on what business you're actually in. We also discuss his prediction for what will make cryptocurrency boom again and his unconventional take on why brand advertising is a waste of money for startups. Mark Cuban is a billionaire entrepreneur, owner of the Dallas Mavericks, and star investor on Shark Tank. Despite his success, he remains refreshingly honest about the psychological challenges of high-level business and the mistakes he's seen countless entrepreneurs make. What we discuss: Why Mark Cuban Still Gets Imposter Syndrome Around AI Experts The "Hamster Wheel" Hiring Mistake That Kills Startups Why He Says "You've Got to Be Able to Solve Problems Yourself" His Honest Take on Losing Money in the Voyager Crypto Collapse The Difference Between USD and USDC That Cost People Millions Why the NBA Thought They Were in the Wrong Business (And How He Fixed It) His Prediction for What Will Make Crypto Boom Again Why Brand Advertising is "Typically a Waste of Money" for Startups The Two Things Every Business Must Sell: Differentiation and Path of Least Resistance Thank you to our sponsor: Therasage: Head over to therasage.com and use code Be Bold for 15% off BiOptimizers: Want to try Magnesium Breakthrough? Go to https://bioptimizers.com/jennifercohen and use promo code JC10 at checkout to save 10% off your purchase. Timeline Nutrition: Get 10% off your first order at timeline.com/cohen Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Find more from Mark Cuban: Instagram: https://www.instagram.com/mcuban/ Find more from Jen: Website: https://www.jennifercohen.com/ Instagram: @therealjencohen Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagements

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Episode 486: Mark Cuban: Why Most Entrepreneurs Hire Wrong (And Go Broke)