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

Sep 19, 2025

Mark Cuban, billionaire entrepreneur and Shark Tank investor, dives into the challenges of hiring for startups, revealing that most entrepreneurs make critical mistakes. He candidly shares his own struggles with self-doubt and stress in high-stakes environments. Cuban also discusses the future of cryptocurrency, emphasizing the importance of clear utility for its resurgence. His bold stance on brand advertising suggests it's often a waste for new businesses. Finally, he reframes sports as an emotion-driven experience rather than just a game.

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ADVICE

Be Able To Solve Core Problems Yourself

Avoid hiring someone and then depending on them to solve core problems for you.
Learn to solve your company's core problems yourself before hiring others to execute.

INSIGHT

Know Your Core To Lead Others

Founders must master their core competency to train and set goals for hires.
If you can't do the work yourself, you won't know how to communicate expectations to your team.

ANECDOTE

Reframing The NBA Business

The NBA thought it was in the basketball business until Mark Cuban reframed it as emotion and entertainment.
He focused on fan experiences and emotional attachment to transform the product offering.

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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

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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