By Panayiotis Constantinou, Contributor
For a rising number of modern athletes, the finish line isn’t the end—it’s the launchpad. In an era where brand partnerships, equity deals, and angel investing are reshaping the post-sport landscape, the question is no longer if athletes should invest—but how.
But startup investing is no playground. While headlines celebrate athletes turning thousands into millions, there’s a quieter reality: for every unicorn, there are a dozen flops. Winning as an investor requires more than capital. It demands discernment, discipline, and the humility to ask tough questions.
Let’s walk through how athletes can – and do – successfully evaluate startups and early-stage ventures, not just as fans or celebrities, but as strategic investors.
1 | Invest in What You Understand
When Kevin Durant launched Thirty Five Ventures, his team made one thing clear: they weren’t chasing hype. They invested in industries Durant already had affinity with—media, sports tech, consumer products—and turned insider knowledge into strategy. One early win? Postmates, which netted him a reported 10x return after Uber acquired it.
Why it worked:
- Durant understood the lifestyle and market the product served.
- His team knew how to spot consumer behavior shifts before they hit Wall Street.
Lesson: don’t chase trends you can’t explain. If you wouldn’t use the product—or at least understand who does—you probably shouldn’t be funding it.
2 | Evaluate the Founders, Not Just the Idea
Andre Iguodala (of NBA and tech investing fame) once said he evaluates startup founders the same way he evaluates teammates: “Do they have the grit? Are they coachable? Can they handle pressure?” His early investment in Zoom – yes, that Zoom – wasn’t just about the product. It was about the leadership.
In early-stage investing, the product might pivot, but the founder is the constant.
So, ask:
- Do they have experience in the space?
- Have they failed before—and what did they learn?
- Are they full-time committed, or just testing the waters?
A mediocre idea with a brilliant founder can still win. The reverse rarely does.
3 | Know Where You Add Value – And Where You Don’t
When Naomi Osaka invested in the skincare brand Kinlò, she wasn’t just cutting a check. The brand focused on melanin-rich skin and sun care, an area she was deeply connected to both personally and publicly. Her visibility, voice, and story added immediate traction to the product launch.
If you’re a public figure:
- Ask how your name will be used. Equity is fine; exploitation is not.
- Clarify whether you’re a silent investor or expected to promote.
- Never substitute brand power for due diligence.
You can be the difference-maker—but only if you’re aligned with the brand’s mission and market.
4 | Ask About the Exit
One of the most overlooked questions in startup investing is also the most important: How do I get my money back?
Carmelo Anthony, through his firm Melo7 Tech Partners, has been vocal about backing companies with clear exit potential. Whether via IPO, acquisition, or revenue share, his team focuses on startups that can eventually generate real returns—not just headlines.
Key filters:
- Is this company likely to be acquired? If so, by whom?
- Are they building to sell, scale, or stay private long-term?
- What’s the timeframe for potential return?
Excitement is easy. Liquidity is rare. Make sure you know the path before you write the cheque.
5 | Diversify—and Expect Losses
Baron Davis once joked that startup investing is “like the NBA playoffs—you need a deep bench, because most players won’t make it to the Finals.” The same goes for your portfolio.
Even the best investors expect most early-stage bets to fail. But with smart diversification—10 to 15 small positions across industries—you increase your odds of backing a winner.
Remember:
- Only invest what you can afford to lose.
- Track each investment carefully: updates, milestones, and financials.
- Use syndicates or venture funds if you’re new—it spreads risk and gives access to vetted deals.
Don’t swing for the fences with every dollar. Singles and doubles build just as much wealth over time.
Final Word: Invest Like a Pro—On and Off the Field
Athletes are uniquely positioned to thrive in the venture world. They know how to bet on potential, how to train for the long game, and how to recover from losses. But winning as an investor isn’t about flash—it’s about fundamentals.
Start with what you know. Partner with founders who treat their vision like a championship run. Be honest about your role, your risk tolerance, and your reason for investing.
The startup world doesn’t promise guarantees—but it rewards those who ask the right questions, at the right time, with the right people. And that, in the end, is a mindset every great athlete already understands. Read our previous article about Your Life Plan.
The Money Smart Athlete® Blog is established and run by the Sports Financial Literacy Academy® (SFLA). Through its education programs, the SFLA has the vision to financially educate and empower athletes of all ages to become better people, not just better athletes. For more information on our courses, our SFLA Approved Trainer Program®, and how they can benefit you and your clients, please get in touch with us at [email protected] .