"Had no money" — Shark Tank's Mark Cuban recalls being broke in his 20s

Shark Tank's Mark Cuban sat down with columnist Jules Terpak for an interview on her Fishbowl podcast on December 17, 2024. During their conversation, Cuban reflected on his early days as a young entrepreneur, including his time at MicroSolutions, which he eventually sold for $6 million.

He shate that he lived a humble life in his 20s. He resided in a modest $750-per-month apartment with five other roommates. Jules chimed in and wondered whether this living situation could be "suffocating," but the Shark Tank investor looked back on this time fondly.

Mark reminisced that the apartment was like a fraternity house, filled with camaraderie among the roommates. Although he acknowledged that the living conditions were far from ideal, the Shark Tank judge was grateful for the roof over his head, given his financial struggles at the time.

"Don't get me wrong. It was a sh*thole. But I'm broke, you know? And the option is, what? I didn't have any options. I mean, I literally had no money," shared Mark.

Mark recalled that to make ends meet, he took on a job as a bartender at night and later found work in business software sales.

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Shark Tank's Mark Cuban had a goal of partying around the world and meeting new people

The Shark Tank investor Mark Cuban and Jules Terpak discussed how Mark's relationship with money changed after selling MicroSolutions. Mark explained that his mindset shifted significantly, but he made a conscious effort to preserve certain values from his pre-wealth days.

Mark credited his father with teaching him that time is the most valuable asset one doesn't own. This lesson, combined with the principles outlined in the book How to Retire by the Age of 35, instilled in the Shark Tank's investor's strong desire to live frugally and save aggressively at the time.

When Mark earned $2 million from the sale of MicroSolutions, he instructed his broker to invest the funds conservatively, as if he were 60 years old. This approach allowed him to prioritize long-term financial security over short-term indulgences.

Mark's spending habits reflected his values, as he opted for practicality over luxury. He shared that he bought a lifetime pass on American Airlines and bought a modest house in a desirable neighborhood. His focus remained on having fun and enjoying life, rather than accumulating material possessions.

"And I bought a lifetime pass on American Airlines, and I still didn't live, you know, well, by the time I sold, I just bought a house, the worst house in the best neighborhood, um, but, you know, I wasn't big into that. I wasn't big into cars, and so I wanted to live like a student, just have fun. That's all I cared about," stated Mark.

Mark Cuban's attitude towards money underwent a significant transformation after selling MicroSolutions. Initially, he adopted a carefree approach as he had a goal to travel and socialize extensively. His goal was to enjoy life, not to flaunt his wealth.

However, Mark's relationship with money changed dramatically when he began interacting with a broker from Goldman Sachs. The broker recognized Cuban's expertise in technology and encouraged him to share his insights publicly. As Mark started making investment recommendations, he achieved remarkable success, even launching and selling a hedge fund within nine months.

When Mark co-founded AudioNet with Todd Wagner, he was already financially secure, having achieved "f*ck you money," which allowed him to pursue his interests freely. Initially, Mark planned to offer advice and support for the project. However, as AudioNet gained traction, he became more actively involved than he originally intended.

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You can catch Mark Cuban on Shark Tank season 16 as it will be his last season on the reality show.