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Habits and Hustle

Episode 483: Mark Cuban's Cold Email Empire: How $750K Investments Turn Into Billion-Dollar Returns

12 Sep 2025

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Listen to the full episode: https://www.youtube.com/watch?v=ThY-UBFtGK8  What if I told you Mark Cuban has invested over $100 million in companies from complete strangers who just sent him an email? In this Fitness Friday episode, I'm sharing insights from my conversation with Mark Cuban about his unconventional investment approach and the incredible companies built from cold outreach. We discuss how Cuban manages 200+ investments with just 12 team members, why he answers every single email personally, and the remarkable stories behind two of his biggest wins: a $4 billion space company and a revolutionary pharmacy that's disrupting Big Pharma. Mark Cuban is a billionaire entrepreneur, owner of the Dallas Mavericks, and star investor on Shark Tank who has built his reputation on being accessible to anyone with a compelling business idea. What we discuss: The $750K Investment That Became Worth "A Whole Lot of Money" at $4B Valuation Why Cuban Reads Every Email and Deletes Most in Under 2 Seconds How He Manages 200 Companies with Only 12 Employees The Cold Email Strategy That Led to Cost Plus Drugs Revolution Behind the Scenes of Shark Tank: Why 75% of His Deals Actually Close The Real Reason Most Shark Tank Entrepreneurs "Ghost" Their Deals How Cuban Turns Alyssa's Cookies Into a $20M Business With Zero Advertising Why He Refuses Meetings But Responds to Strangers' Emails Within Minutes The One Question Every Entrepreneur Must Ask: "Why Didn't I Think of That?" Thank you to our sponsor: Therasage: Head over to therasage.com and use code Be Bold for 15% off  Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. 99designs by Vista: 99designs.com/jen20  – click "Claim my discount" to get $20 off your first design contest.  Momentous: Shop this link and use code Jen for 20% off  Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order 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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