Mark Cuban says he only felt successful for the first time at age 28: My dad ‘broke down in tears and started sobbing’

Billionaire investor Mark Cuban vividly remembers the moment he finally felt successful — because he spent so many years beforehand trying to stave off being flat broke.

In his 20s, Cuban shared a three-bedroom apartment with five roommates and used grocery store hacks to pinch pennies. Fired from a tech sales job, he started a software company called MicroSolutions that gained momentum quickly — $15,000 in revenue in its first two months, Cuban recently told GQ — until his secretary stole $82,000 from its bank account, leaving just $2,000 behind.

Roughly a year later at age 28, after rebuilding his startup nearly from the ground up, Cuban reached a personal milestone that told him he’d finally made it.

The turning point “was probably when I had $100,000 in the bank,” Cuban, now 65, said. “I remember telling my buddy Dave Winslow, we’re sitting at a bar and telling him, being so proud. And telling my dad who just broke down in tears and started sobbing.”

Adjusted for inflation, Cuban’s $100,000 in personal savings would be worth roughly $280,000 today. That’s more than the average American household has in savings — $41,600, according to 2019 Federal Reserve data.

It’s also a lot less than the net worth Americans say they need to feel wealthy: at least $2.2 million on average, financial services company Charles Schwab’s annual Modern Wealth Survey recently found.

For Cuban, the $100,000 benchmark was a sign that his finances and startup were finally stable, especially following his secretary’s theft a year prior.

Losing so much money overnight “was f—ed up, but [it was] the best thing that ever happened to us, because it made us get our s— together,” Cuban told Barstool Sports’ “Pardon My Take” podcast in 2020.

His turnaround strategy was simple: He put his head down and worked. At the time, he spent most days reading Cisco router manuals and “sitting in my house testing and comparing new technologies,” he wrote in a 2004 blog post.

The effort paid off when Cuban sold MicroSolutions for $6 million in 1990 to CompuServe, a now-defunct internet services company. The deal made Cuban a millionaire at age 32 — a career milestone he topped seven years later, when he sold his next company Broadcast.com to Yahoo for $5.7 billion in 1997.

“There’s a huge difference between being a millionaire and a billionaire,” Cuban told GQ. “After I sold my first company, I had like $2.5 million dollars in the bank [and] I still kept a budget. I still have that budget, actually.”

Disclosure: CNBC owns the exclusive off-network cable rights to “Shark Tank,” which features Mark Cuban as a panelist.

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