Uber, Iman Shumpert, billionaire
by Mary Spiller
November 10, 2025
The former NBA star opens up about selling his Uber shares too soon — and the lessons he learned about patience, trust, and building wealth on his own terms.
Iman Shumpert may have earned his championship ring on the court, but one of his most memorable lessons came from off it — and it cost him millions. The former NBA guard recently revisited one of his early business missteps: selling his Uber shares long before the company became a global powerhouse.
In a 2020 interview with DJ Vlad — per Basketball Network — Shumpert candidly described the decision as “idiotic,” acknowledging that impatience and the desire for a quick profit clouded his judgment. “I went for the quick flip,” he admitted. “I saw the shares climb, cashed out, and moved my profit somewhere else.”
At the time, the Illinois native was just beginning to explore investing, juggling his budding NBA career with a drive to expand into business. His early bet on Uber was smart — but selling too soon meant missing out on what became one of the most successful startups in history.
Uber, founded in 2009, now operates in more than 70 countries and has a valuation exceeding $200 billion. Had Shumpert held onto his shares, the return could have been life-changing. Instead, the former Cleveland Cavaliers champion walked away with what he calls “a lesson in patience.”
Looking back, Shumpert said the experience taught him more than just financial strategy — it reshaped his approach to trust and investment. “I always hated investing in other people’s minds… I felt like I couldn’t trust that in other people,” he said. That realization pushed him to focus on ventures where he had creative and operational control.
Though his dream of building an app to rival Uber didn’t materialize, Shumpert refuses to frame the episode as a failure. “It wasn’t a mistake,” he said. “It was just inexperience.” Over time, that experience translated into a more disciplined and self-directed approach to business.
During his decade in the NBA, Shumpert earned roughly $50 million — enough cushion to explore new opportunities and learn from missteps. Today, he treats his early errors as part of the process, using them to shape smarter, longer-term decisions.
In hindsight, Shumpert’s story isn’t just about missing a billion-dollar wave — it’s about understanding that success, whether on the court or in business, often depends on staying in the game long enough to see it through.
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