Even beyond the roar of the stadium, Serena Williams, the undisputed GOAT, has channeled her legendary drive into the high-stakes world of venture capital with Serena Ventures, established in 2014. Imagine the tension as this champion of the court now navigates pitch decks, her focus as laser-sharp as her serve. In 2022, she launched her inaugural $111 million fund, a bold move to champion underrepresented founders. While building a formidable portfolio of over 60 companies, including a staggering 14 unicorns by early 2025, the journey hasn’t been without its silent battles.
Speaking to Time Magazine, published on April 16, Serena got real about the highs and lows of being a venture capitalist. Every investment is a calculated risk, a potential triumph or a quiet setback in this new arena, where her estimated $340 million net worth in 2025 fuels a different kind of game altogether. However, it’s been nearly a decade since she launched Serena Ventures. What was the hardest part of this business?
She revealed, “The biggest challenge for me in the investing role is just narrowing down who to invest in. because there’s just so many different opportunities and I want to say ‘yes’ to a lot of them because a lot of them are so intriguing and so interesting but, you know, you can’t.” With a portfolio as big as hers, isn’t it surprising she faced this conundrum?
For some context, Williams co-founded Serena Ventures in 2014 with Alison Rapport Stillman, a venture capital firm laser-focused on backing under-represented founders. Impressively, 79% of their investments are in such companies, including 54% women-led, 47% Black-led, and 11% Latino-led. Serena Ventures has invested in over 85 companies, with a remarkable fourteen achieving Unicorn status (over $1 billion valuation). So, how did she make it work? Well, she added, “So I just try to narrow it down, do due diligence to see, ‘is this company going to make it,’ and invest in them.”
Unsurprisingly, the competitive fire of the sporting world has drawn Serena Williams into its investment arena. Her initial foray ignited in 2009, when she and Venus made history as minority owners of the Miami Dolphins, shattering barriers as the first African-American women with a stake in an NFL team. The exact size of their ownership remains a tantalizing mystery, yet the team’s soaring valuation, from $1.1 billion to a staggering $5.7 billion by January 2024, hints at a shrewd early move.
Furthermore, Williams is a pivotal force behind Angel City, the dynamic women’s football club launched in 2020, joining a constellation of stars like Billie Jean King and Natalie Portman in this exciting venture.
Beyond her shrewd investments, Serena has also proven herself a formidable entrepreneur, birthing several ventures from her own vision. Imagine the unveiling of WYN Beauty in April 2024, a make-up brand infused with her signature strength and vibrancy. Or the launch of Will Perform in December 2022, a body care line crafted for peak performance. Not content with just conquering one industry, she has also marked the fashion world with clothing lines like Serena and Aneres!
But what about her first time investing? Well, it didn’t go as smoothly as one might think. In fact, Serena even admitted to making a few mistakes along the way.
Serena opens up about the peer pressure during her first time investing
In December 2024, during a chat with Andrew Ross Sorkin for the New York Times Events, Serena Williams reflected on her post-tennis career and her leap into the investment world. With an impressive 73 singles titles behind her, Serena revealed she couldn’t pick a single best investment. “We have so many that we’re so proud of. We have a unicorn in our fund already. Our fund is only a couple of years old,” she shared, clearly proud of her growing portfolio.
But she also revealed her “worst investment” – a rookie mistake from over 15 years ago when she jumped into a deal solely because other celebrities were involved. “I didn’t even know what ‘due diligence’ meant back then,” she admitted with a laugh. That company? “I can’t remember the name of that company. But it doesn’t exist,” she joked. Lesson learned, Serena said, “I learned a lot from that.”
Fast forward to April 2025, Serena’s empire is thriving with Serena Ventures, her fashion line S by Serena, and Wyn Beauty, which just celebrated its one-year anniversary on April 2. At Wyn Beauty’s recent pop-up in Los Angeles on April 11, she told People Magazine, “I’m done! I’m not launching anything else like this.” She’s happy focusing on Wyn Beauty, being a mom, and running her venture company. “That’s a lot. We’re good!” she declared, sounding content and confident in this chapter of her life.
But knowing Serena, can she really stop here? The GOAT has a knack for surprising us, always bringing something fresh and exciting whenever she closes a door. So, what do you think we could expect next? Share your thoughts in the comments below!
The post “Is This Company Going to Make It?” Serena Williams Talks Investor Doubts to TIME as She Reveals Her Success Strategies appeared first on EssentiallySports.