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

Sep 12, 2025

Mark Cuban, billionaire entrepreneur and Shark Tank star, shares his intriguing investment strategy that has led to over $100 million in returns from cold emails. He details managing 200 investments with only 12 team members and why he personally responds to every email, including a humorous take on Alyssa's Cookies. Cuban unveils the groundbreaking pharmacy model disrupting Big Pharma and reflects on the curious nature of entrepreneurs. Tune in for insights into what makes a pitch stand out and how innovation can transform industries.

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ANECDOTE

From Living In A Car To $20M Cookie Brand

Mark Cuban received Alyssa's Healthy Cookies from Doug when Doug was living out of his car and invested to help scale them.
The product changed from large cookies to bite-sized pieces and now does nearly $20M in revenue without paid advertising.

ADVICE

Evaluate Product Before People

Look for product first because a great product sells even if the team needs work.
Ask yourself, "Why didn't I think of that?" to test whether the product is compelling and differentiated.

INSIGHT

TV Decisiveness Hides Long Conversations

Shark Tank pitches are much longer off-camera, so on-screen decisiveness reflects heavy editing.
Cuban's quick reactions on TV hide 20–120 minute real conversations and preparation.

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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?"

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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