Jalen Rose Regrets Missing Out on Billion-Dollar Investments

The former NBA player shares his business journey and the investments he wishes he had made early on.

Apr. 19, 2026 at 9:04pm

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A minimalist, high-contrast studio photograph featuring a modern smartphone, laptop, and abstract geometric shapes in shades of gray and blue, symbolizing the world of technology investments.Jalen Rose's missed opportunities in the tech industry serve as a cautionary tale for athletes-turned-entrepreneurs.Today in Detroit

Retired NBA player Jalen Rose reveals that he regrets not investing in companies like Uber and Zoom early on, which have since become billion-dollar businesses. Rose shares his journey into the business world, including seeking help from a financial advisor to learn about the stock market while still playing in the NBA. Despite missing out on some lucrative investments, Rose has found success in real estate, founding his own production company, and establishing a charter high school in his hometown of Detroit.

Why it matters

Rose's story highlights the challenges and opportunities that professional athletes face when transitioning into the business world. His candid admission about the investments he missed out on provides valuable insights for others looking to diversify their income streams and make smart financial decisions.

The details

Rose, who played in the NBA for 13 years, shared that he had a similar version of the ridesharing company Uber but ultimately decided against it. He also regrets not getting in on the video conferencing platform Zoom early on, saying 'that's one that I wish I would have got in on.' Rose said he got interested in investing while still playing in the NBA, seeking help from a financial advisor to learn about the stock market. He made over $102 million in his career and invested in real estate as part of his personal portfolio. Rose also founded Three Tier Entertainment, a management and production company, and recently partnered with Detroit Pistons owner Tom Gores to form the production company Same Page Entertainment. In addition to his business ventures, Rose serves as the board president of the Jalen Rose Leadership Academy, a charter high school in Detroit, and does broadcast work as an analyst for various sports media outlets.

  • Rose played in the NBA for 13 years, retiring in 2007.
  • Rose founded Three Tier Entertainment and the Jalen Rose Leadership Academy after his NBA career.
  • Rose recently partnered with Detroit Pistons owner Tom Gores to form Same Page Entertainment in 2026.

The players

Jalen Rose

A former NBA player who has become an active businessman since retiring from the game, including founding his own production company and charter high school.

Tom Gores

The owner of the Detroit Pistons, who recently partnered with Jalen Rose to form the production company Same Page Entertainment.

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What they’re saying

“I wish I would have got in for Uber early. Yeah, cause I'm a Detroiter, we're the Motor City. I have a chauffeur's license.”

— Jalen Rose, Former NBA Player

“You know the thing I'm mad that all of us missed out on? Zoom. That's one that I wish I would have got in on.”

— Jalen Rose, Former NBA Player

What’s next

Rose continues to explore new business opportunities and investments, leveraging his experience and connections in the sports and entertainment industries.

The takeaway

Jalen Rose's story serves as a cautionary tale for professional athletes and others looking to diversify their income streams, highlighting the importance of staying informed about emerging trends and being willing to take calculated risks when it comes to investing.