Jalen Rose on Missed Opportunities: Why He Wishes He Invested in Uber and Zoom

Former NBA star and current analyst Jalen Rose has openly reflected on investment decisions he wishes he had made during and after his basketball career. In recent interviews, Rose specifically named Uber and Zoom Video Communications as two companies he believes would have been transformative additions to his portfolio. His candid remarks offer insight into the mindset of athletes navigating post-sports financial planning and highlight the lasting impact of early-stage tech investments.

The Context: Athletes and Investment Regrets

Professional athletes often face unique financial challenges. Despite earning substantial incomes during their careers, the average NBA player’s career lasts just 4.5 years, according to the National Basketball Players Association. This compressed earning window makes strategic investing critical for long-term wealth preservation.

Rose, who played 13 seasons in the NBA before transitioning to broadcasting and entrepreneurship, has been vocal about the importance of financial literacy for athletes. In a 2023 interview with GQ, he stated, “I didn’t know what I didn’t know when I was coming up. Now I try to pass on those lessons.” His reflections on Uber and Zoom stem from that same desire to educate others about recognizing disruptive innovation early.

Why Uber and Zoom Stood Out to Rose

Rose did not specify exact timelines for when he wished he had invested, but both companies experienced explosive growth during the 2010s — a period when he was actively engaged in business ventures and media work.

Uber: Riding the Wave of Urban Mobility

Founded in 2009, Uber disrupted the transportation industry by leveraging smartphone technology to connect riders with drivers. By 2015, the company was operating in over 300 cities worldwide and had raised billions in venture capital. Its 2019 IPO valued the company at approximately $82 billion, according to SEC filings.

For Rose, Uber represented more than just a ride-hailing app — it was a fundamental shift in how people navigate cities. “When you see something change behavior that fast, you have to pay attention,” he noted in a 2022 panel discussion at the Milken Institute Global Conference.

Zoom: The Unexpected Essential

While Uber’s trajectory was widely anticipated by tech investors, Zoom’s rise was more unexpected — until it became indispensable. Founded in 2011 by former Cisco engineer Eric Yuan, Zoom gained traction slowly until the COVID-19 pandemic triggered a global shift to remote work and virtual communication.

In 2020, Zoom’s daily meeting participants surged from ~10 million in December 2019 to over 300 million by April 2020. Its stock price climbed from around $70 per share in early 2020 to a peak of over $500 later that year.

Rose admitted he underestimated Zoom’s staying power, assuming it would be a temporary solution. “I thought it was just a pandemic thing,” he said in a 2023 interview with CNBC Produce It. “Turns out, it’s how we work now.”

Lessons for Investors and Athletes Alike

Rose’s reflections underscore several key principles for building wealth beyond a primary career:

• Look for behavioral shifts: The most successful investments often address changes in how people live, work, or interact.
• Don’t wait for perfection: Waiting to fully understand a technology can mean missing early entry points.
• Diversify beyond the familiar: Athletes often invest in real estate, restaurants, or franchises — sectors they know. Tech requires different due diligence but offers scalable returns.
• Leverage platform access: Many athletes now use their networks to gain early access to startup opportunities through funds or advisory roles.

Rose himself has since become more active in the investment space. He co-founded the Jalen Rose Leadership Academy in Detroit and has partnered with financial literacy initiatives aimed at young athletes. While he doesn’t disclose specific portfolio details, he advocates for disciplined, long-term thinking.

The Broader Picture: Athlete Investors in Tech

Rose is not alone in regretting missed tech opportunities. Other NBA figures have shared similar sentiments:

• Kevin Durant has built a robust investment portfolio through his firm Thirty Five Ventures, including early stakes in companies like Postmates and Acorns.
• Stephen Curry invested in Snap Inc. And Lyft before their IPOs and has since launched his own venture fund, SC30.
• Retired star Kobe Bryant famously invested $6 million in BodyArmor, which was later acquired by Coca-Cola for $5.6 billion — a return he often cited as proof of athlete-led venture success.

These examples reflect a growing trend: athletes leveraging their platform, discipline and networks to participate in innovation economies. According to a 2023 Sportico analysis, over 40% of active NBA players now have some form of investment in startups or venture funds.

Looking Forward: What’s Next?

While Rose can’t change the past, he remains focused on future opportunities. He has expressed interest in areas like artificial intelligence, clean energy, and 5G-enabled infrastructure — sectors poised for transformation over the next decade.

His message to young athletes and professionals alike is clear: Pay attention to what’s changing, not just what’s big today. The next Uber or Zoom may not look like either — but it will solve a problem in a way that alters daily behavior.

Key Takeaways

• Jalen Rose wishes he had invested in Uber and Zoom due to their disruptive impact on transportation and communication.
• Both companies experienced exponential growth during the 2010s and early 2020s, driven by technological adoption and societal shifts.
• Rose uses his experience to advocate for financial literacy and proactive investing among athletes.
• His reflections highlight a broader trend of athletes engaging with venture capital and technology investing.
• Identifying early behavioral changes — not just financial metrics — can help uncover high-potential opportunities.

Frequently Asked Questions

Did Jalen Rose ever invest in Uber or Zoom?

There is no public record indicating that Jalen Rose made direct investments in Uber or Zoom. His comments reflect regret over missed opportunities, not confirmed past actions.

How much could an early investment in Uber or Zoom have returned?

An investment of $10,000 in Uber’s 2019 IPO would be worth roughly $25,000–$30,000 today (as of mid-2024), depending on timing. The same amount in Zoom at its 2020 peak could have exceeded $70,000 before declining from its highs — though long-term holders who bought earlier saw even greater gains.

What is Jalen Rose doing now to support athlete investing?

Rose promotes financial education through public speaking, media appearances, and partnerships with organizations like the National Basketball Retired Players Association. He emphasizes mentorship and access to credible financial advisors.

Are athletes getting better at tech investing?

Yes. With the rise of athlete-focused venture funds, syndicates, and educational programs, more players are gaining access to private markets and making informed early-stage investments.

Jalen Rose’s honesty about his investment regrets serves a purpose beyond personal reflection. By sharing what he wishes he had done, he helps others recognize the value of curiosity, timing, and the courage to invest in what could be — not just what is.