Famous Quote
“It doesn't matter how many times you fail. You only have to be right once.”
Why #55
Cuban sold Broadcast.com at the dot-com peak for $5.7B, transformed the Dallas Mavericks into NBA champions, became America's most famous investor on Shark Tank, and is now disrupting pharmaceutical pricing with Cost Plus Drugs.
The Story
Mark Cuban sold Broadcast.com to Yahoo for $5.7 billion in 1999, bought the Dallas Mavericks, became a Shark Tank icon, and then disrupted the pharmaceutical industry with Cost Plus Drugs — proving that a billionaire can reinvent himself across decades and industries while maintaining a common-man persona that makes him America's most relatable billionaire.
Cuban started as a bartender in Dallas, then founded MicroSolutions (a computer consulting firm) and sold it for $6 million. He used that money to co-found Broadcast.com, one of the first internet streaming companies, which Yahoo acquired for $5.7B at the peak of the dot-com bubble. Cuban famously hedged his Yahoo stock, protecting his fortune when the bubble burst.
His purchase of the Mavericks transformed the team from a league joke into a 2011 NBA champion. His confrontational sideline presence (he was fined $2M+ by the NBA) made him a cultural figure. On Shark Tank, he invested in over 85 companies and became the show's breakout star. In 2022, he launched Cost Plus Drugs, which sells medications at cost plus a 15% markup — exposing pharmaceutical pricing and attracting millions of customers.
Key Achievements
Sold Broadcast.com to Yahoo for $5.7B (1999)
Bought the Dallas Mavericks — won NBA championship (2011)
Star investor on Shark Tank — 85+ investments
Founded Cost Plus Drugs — disrupting pharmaceutical pricing
Hedged Yahoo stock after sale — protected fortune when bubble burst
Founded MicroSolutions — sold for $6M (first exit)
By the Numbers
$5.7B
Broadcast.com Exit
$2M+
NBA Fines
85+
Shark Tank Investments
Millions
Cost Plus Drugs Users
Fun Facts
He was a bartender in Dallas before starting his first tech company.
He hedged his Yahoo stock with collar contracts — when Yahoo's stock crashed 97%, Cuban kept his billions.
He has been fined more than $2 million by the NBA for arguing with referees from courtside.
He taught himself about streaming media by reading everything he could find — he had no formal tech training.
He once rented out an entire movie theater so his Mavericks players could watch a film together after a win.
Frequently Asked Questions
Who are the greatest entrepreneurs of all time?
The greatest entrepreneurs include Steve Jobs (Apple), Elon Musk (Tesla/SpaceX), Jeff Bezos (Amazon), Bill Gates (Microsoft), and Mark Zuckerberg (Meta). Each built companies that fundamentally changed how the world works — from personal computing and smartphones to e-commerce, cloud computing, and social media.
What makes someone a successful entrepreneur?
Successful entrepreneurs share several traits: the ability to identify unmet needs, willingness to take calculated risks, relentless execution, and resilience in the face of failure. They combine vision with practical problem-solving and are willing to persist long after most people would quit. Capital and credentials matter far less than most people think — resourcefulness beats resources.
Can you become an entrepreneur without a business degree?
Absolutely. Many of the greatest entrepreneurs had no business education. Steve Jobs dropped out of college. Richard Branson left school at 16. Sara Blakely was selling fax machines. Henry Ford had no formal engineering training. Jack Ma was an English teacher. What matters is not the degree — it is the ability to see an opportunity, build something people want, and persist through failure.
Get Glen's Musings
Occasional thoughts on AI, Claude, investing, and building things. Free. No spam.
Unsubscribe anytime. I respect your inbox more than Congress respects property rights.
Keep Exploring
Top 25 Famous Entrepreneurs
See the full ranked list of the greatest entrepreneurs of all time.
Read moreBillionaires & Icons
Profiles of the world's most successful investors and builders.
Read moreTop 25 Value Investors
The greatest value investors of all time, ranked.
Read moreGreatest Trades Ever
The most legendary investment decisions in financial history.
Read moreTop 25 Stock Market Books
The 25 books every investor should read.
Read moreTrack Record
Glen Bradford's documented investment returns since 2013.
Read more