Serena Williams founded Serena Ventures in 2014. Forbes reported in April 2024 that the firm had invested in more than 85 companies, that 14 of those portfolio companies had reached $1bn valuations, and that 79% of its founders came from underrepresented groups, including 54% women.
Those are not the numbers of a celebrity name attached to somebody else’s fund. They are the numbers of a venture portfolio with a stated thesis, a documented hit rate and a decade of vintage behind it.
The shift that produced them is the subject here, and it is more recent and more structural than the profiles usually suggest.
1. The statistic that shaped a generation of advice was never sourced
For fifteen years, almost every conversation about athletes and money started from the same place. Sports Illustrated reported in March 2009 that 78% of former NFL players had gone bankrupt or were under financial stress within two years of retirement, and that 60% of former NBA players were broke within five years. The figures were attributed only to “a host of sources”. No study, no sample, no methodology was published alongside them.
The research that followed does not support the claim. Using federal bankruptcy court records for players drafted between 1996 and 2003, Carlson, Kim, Lusardi and Camerer found that 15.7% of NFL players had filed for bankruptcy by year 12 after retirement, and only about 1.9% within two years of retiring, in National Bureau of Economic Research Working Paper 21085, published on 13 April 2015.
Fifteen point seven percent across twelve years is a serious number and a real problem. It is also a fundamentally different problem from the one the 78% figure described. Slow attrition over a decade calls for different advice than a cliff at retirement, and the industry spent years designing for the cliff.
The same NBER study found something more uncomfortable than either figure. Bankruptcy risk was unrelated to total career earnings or to career length. Earning more, for longer, did not protect players. Whatever was going wrong was not a shortfall of income.
2. The money grew faster than the infrastructure around it
The products aimed at athletes have become more sophisticated at the same time as the sums reaching them have grown. What has not scaled at the same rate is the advisory apparatus around either.
The NFL set its 2026 salary cap at $301.2m per club, the first time above $300m and up $22m from $279.2m in 2025, the league announced in February 2026. The NBA set the 2025-26 cap at $154.647m, the maximum 10% increase its agreement permits, according to the league’s June 2025 announcement. Neither ceiling is a payment. Both mark how quickly the pool of money reaching individual players has been rising, and the advice industry has not kept pace with either of them.
3. The vehicles stopped being endorsements and started being firms
The clearest marker of the change is organisational. Athletes stopped taking equity as a favour and started building entities that raise, deploy and report.
Kevin Durant and Rich Kleiman founded Thirty Five Ventures in 2016, and the firm has backed more than 100 companies including Coinbase and Robinhood, according to Adweek. Durant, through Thirty Five Ventures, took a 5% stake in MLS club Philadelphia Union with an option for a further 5%, as NBA.com reported in June 2020.
Carmelo Anthony partnered with Isos Capital founders George Barrios and Michelle Wilson to launch Isos7 Sports Investments in February 2023, targeting $50m to $100m per investment, per PR Newswire. Cheque sizes at that level are not personal allocations. They are institutional positions requiring diligence teams, structure and co-investors.
Penny Jar Capital, founded in 2021 by Bryant Barr and Richard Scudellari with Stephen Curry as special adviser, closed its first fund in September 2021 and filed to raise a second in October 2024, as TechCrunch reported. Filing for a second fund is the part that matters. It means the first one produced enough of a story to go back out with.
4. Syndicates replaced solo bets
Otro Capital’s €200m investment in Formula 1 team Alpine Racing, announced in October 2023, brought in Patrick Mahomes, Travis Kelce, Rory McIlroy, Anthony Joshua and Juan Mata as strategic investors, according to Business Wire.
The structure is the point. Otro Capital led, negotiated and holds the operating relationship. The athletes came in as strategic investors behind a sponsor with a mandate. Nobody in that group had to underwrite a Formula 1 team on their own, and nobody had to be the one who says no.
Athletes writing individual cheques into deals brought to them by acquaintances carry a risk nobody has priced for them. Coming in behind an institutional lead does not eliminate risk. It replaces relationship-driven risk with priced risk, which is a trade most family offices made long ago.
5. Money now arrives years before the first professional contract
The timeline that all of the older advice assumed has been rewritten from the front end.
Judge Claudia Wilken approved the House v. NCAA settlement on 6 June 2025, awarding $2.576bn in back damages over ten years and allowing schools to share revenue directly with athletes up to roughly $20m per school from 1 July 2025, per the Ropes & Gray analysis. The NCAA revenue-share cap for Power 4 programmes is $21.3m per school for 2026-27, according to Opendorse.
Opendorse estimates the total name, image and likeness market reached $4.5bn in the 2026-27 academic year, 61% above its prior projection of $2.8bn, with above-cap commercial NIL accounting for roughly $735m of athlete earnings. On3 valued Texas quarterback Arch Manning at $5.4m and Ohio State receiver Jeremiah Smith at $4.2m entering the 2026 season, per Business of College Sports.
A nineteen-year-old now meets meaningful money, tax complexity and entity formation while still in college. Where that used to happen at the draft, with an agent and an advisor arriving in the same week, it now happens years earlier and often with far less structure around it.
6. The institutions arrived in sequence, and late
Morgan Stanley Wealth Management formed its Global Sports & Entertainment division on 18 November 2014, led by Drew Hawkins. Goldman Sachs launched Sports and Entertainment Solutions in 2018, specifically to address athletes’ compressed earning timelines, and it is led by Nicole Pullen Ross. UBS launched a dedicated Athletes and Entertainers segment in the United States in November 2020, headed by former NFL defensive end Adewale Ogunleye.
Serena Ventures predates all but the first of them, and the ownership stake predates every one of them: Venus and Serena Williams became limited partners in the Miami Dolphins in August 2009, the first African-American women to hold an ownership position in an NFL club, as Agence France-Presse reported that month. The athletes were building the capability before the banks packaged it, which is an unusual order of events and explains why the good athlete-led firms tend to have unusually specific theses rather than generalist mandates.
Tommy Shields, Head of Investor Relations at Onyx Reserve, a private investment firm operating in South Florida, has noticed the change in the questions rather than in the cheque sizes.
“The questions have changed more than the money has. Ten years ago the first question was what the return looks like. Now it is who else is in, what happens if the thing takes eight years instead of three, and who is on the other side of the table when it goes wrong. Those are the questions somebody asks when they have decided this is a career and not a hobby.”
7. What has not been solved
The World Economic Forum, drawing on Oliver Wyman analysis, put the global sports economy at $2.3trn and projected it to reach $3.7trn by 2030, in “Sports for People and Planet”, published on 13 January 2026. The athlete cohort now has access to more of that money than at any prior point.
The NBER finding that bankruptcy risk is unconnected to career earnings still stands, and no amount of NIL money at nineteen addresses a failure mode that has nothing to do with the size of the balance. The firms named here represent the visible top of a cohort several thousand strong, and their success does not tell us much about the median outcome for a player who spent four years in the league and now has a lump sum and no institutional relationship at all.
That median case is the one worth measuring, and nobody has published a credible number on it since 2015.