Podcst
Episode 483: Mark Cuban's Cold Email Empire: How $750K Investments Turn Into Billion-Dollar Returns by Jen Cohen and Habit Nest

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

from Habits and Hustle

by Jen Cohen and Habit Nest

Published: Fri Sep 12 2025

Show Notes

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?"

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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