Serena Williams on winning in business

Serena Williams rebranded her venture firm from Serena Ventures to Starfire Ventures to give the organization an identity larger than her personal name while keeping the SV initials used internally. The firm now has institutional investors on its cap table, has backed approximately 16 unicorns, and roughly 70 percent of portfolio companies have women or people of color as founders. Williams frames this emphasis on underrepresented founders as a broader imperative rather than a purely financial calculation, arguing that other investors subconsciously overlook such founders rather than deliberately excluding them. She is clear that every investment must be one she believes will return the fund, not an act of philanthropy.

Her investing philosophy is approximately 90 percent systematic and 10 percent instinct, with her first investment made roughly 14 to 15 years ago. Portfolio holdings she highlighted include Teal Health, focused on at-home cervical cancer testing to address the problem of women skipping in-office procedures, and Midi Health, which she describes as a unicorn targeting women's health, a sector she says has been historically underserved despite women representing half the population. She has brought on a new partner named Beth Freer, whom she describes as the Serena Williams of VC, and now spends 90 percent of her non-parenting time on Starfire Ventures.

On deals that did not work out, Williams said she chose to pause and take Espy off the market after investor direction conflicted with her VC instincts, framing it as a deliberate choice rather than a failure and noting that outcomes she predicted did occur. Win Beauty, launched with Altas, also did not gain traction. She avoids the word failure entirely, preferring to reframe setbacks as expecting tough challenges rather than expecting to fail.

Williams has no second thoughts about becoming a spokesperson for GLP-1 treatments through Ro, saying the treatments improved her blood test results, removed her candidacy for heart disease, and helped with diabetes and inflammation. Her husband Alexis Ohanian invested in Ro before it was renamed and before she became a spokesperson. She says she and Ohanian maintain a separation between home life and investing discussions, though she notes he works approximately 20 hours a day. She now researches brands thoroughly before agreeing to partnerships and prefers to work only with brands she personally uses, contrasting this with her early Nike relationship, which she entered without the same due diligence she would apply to an investment.

Williams is invested in Angel City FC in the NWSL and is involved with the WNBA's Toronto Tempo. She referenced a panel discussion suggesting women's professional sports typically take about 30 years to reach mainstream parity, drawing a parallel between Billie Jean King's era in tennis and the sport's later mainstream status, and noting the WNBA is now approximately 30 years from its founding. She acknowledged she cannot confirm whether there is data behind the 30-year claim, only that it was stated on a panel.

Williams is not returning to tennis to win Grand Slams, describing that pursuit as a full-time job she is not willing to commit to. She originally retired to have children rather than because she had nothing left competitively. Her primary motivation for returning sporadically is to show her daughters what is possible, particularly Olympia, and she notes her two-year-old daughter Adira already says she wants to play tennis like her mother. She schedules her time to the hour across VC work, family, and tennis.

Her core advice for entrepreneurs is that hard work is consistently underestimated, overnight success stories are rare exceptions, and sustained daily effort on both easy and difficult days is the main factor required to succeed over time.