Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups.

You know Serena Williams as one of the greatest athletes of all time. 24 Grand Slam singles titles. Four Olympic gold medals. Total dominance on the tennis court for two decades.

But here's what most people miss: Serena has been building one of the most interesting investment portfolios in venture capital. And her approach to investing offers lessons that every early-stage investor should pay attention to.

I've been studying Serena Williams investments for a while now, and there's a clear pattern in how she thinks about deploying capital. It's not about celebrity vanity investments or slapping her name on random startups. It's about leveraging her unique perspective as a Black woman athlete to identify opportunities that traditional VCs consistently miss.

Let's break down what makes her approach different and what we can learn from it.

Who is Serena Williams the investor?

Before we dive into specific investments, let's establish some context. Serena launched Serena Ventures in 2014, initially as a vehicle for her personal angel investments. Over time, it evolved into a proper venture firm.

In 2022, Serena Ventures announced a $111 million debut fund. But here's what makes it interesting: the fund focuses on companies led by women and people of color. Not as a charitable cause, but as a legitimate investment thesis.

And the results speak for themselves. By 2024, the portfolio included over 80 companies across various stages and sectors.

The thesis behind Serena Williams investments

Serena's investment approach centers on a simple but powerful observation: underrepresented founders are systematically overlooked by traditional venture capital. This creates market inefficiencies that smart investors can exploit.

The numbers back this up. Despite making up over 50% of the population, women founders received only 2% of total VC funding in 2023. Black and Latinx founders? Even less.

But here's the thing: this isn't about feel-good diversity metrics. It's about recognizing that if 98% of capital is chasing the same demographic of founders, there's probably alpha in the remaining 2%.

This is classic contrarian investing. Go where others aren't looking.

Notable companies in the Serena Ventures portfolio

Let's look at some actual Serena Williams investments and what they tell us about her strategy:

Coinbase: Serena got into Coinbase early, before crypto became mainstream. This wasn't just a lucky bet. It showed foresight about financial infrastructure and how technology could democratize access to financial services.

MasterClass: Another early investment that proved prescient. MasterClass tapped into the creator economy before "creator economy" was even a buzzword. The company understood that people would pay premium prices for direct access to world-class expertise.

Impossible Foods: Plant-based meat alternatives seemed niche when Serena invested. Now it's a massive market category. Again, she saw the trend before it became obvious to everyone else.

Propel: This one's particularly interesting. Propel provides financial services to low-income Americans, many of whom receive government benefits. Traditional VCs overlook this market because they don't understand it. Serena recognized the opportunity because she has a different perspective on which problems are worth solving.

Notice a pattern? These aren't just random bets. They're investments in companies solving real problems for underserved markets or riding emerging macro trends.

What makes Serena's approach different from traditional VCs

Most VCs claim they're looking for the best founders regardless of background. But the data shows this isn't true in practice. Traditional VCs have blind spots, and those blind spots create opportunities.

Network effects work differently for Serena: When a typical Sand Hill Road VC looks for deal flow, they tap into the same networks everyone else uses. Stanford GSB. Y Combinator. Sequoia portfolio companies. Serena has access to completely different networks. Athletes. Entertainment industry insiders. Communities that traditional VCs never reach.

This means she sees deals that others don't. And in venture capital, access to unique deal flow is one of the biggest competitive advantages you can have.

She understands different customer segments: Serena grew up in Compton. She's traveled the world. She's been a Black woman navigating predominantly white spaces her entire career. This gives her insights into customer needs that many VCs simply can't access.

When she looks at a company targeting women or people of color, she can evaluate whether the product actually resonates in a way that a partner at Andreessen Horowitz probably can't.

She's playing a different game with capital: Serena doesn't need venture returns to maintain her lifestyle. She's already wealthy from tennis. This means she can take longer-term bets and support founders through difficult periods without panicking about short-term performance metrics.

This patient capital approach aligns well with backing underrepresented founders who might take longer to scale because they face additional obstacles in fundraising and hiring.

The performance question nobody wants to ask

Here's the uncomfortable truth: we don't have full transparency on Serena Ventures' returns yet. The fund is still relatively young, and many of the investments haven't exited.

But here's what we do know: several portfolio companies have achieved significant valuations. Coinbase went public. MasterClass raised at a multi-billion dollar valuation. Impossible Foods has raised nearly $2 billion.

The early indicators look promising. And more importantly, the thesis is sound. If traditional VCs are systematically overlooking talented founders from certain demographics, then investors who don't have those blind spots should be able to generate outsized returns.

What angel investors can learn from Serena's approach

Studying Serena Williams investments has taught me several lessons that apply to early-stage investing more broadly:

1. Your unique perspective is your edge

Serena isn't trying to be Sequoia. She's leveraging her unique background and networks to find opportunities others miss. As an angel investor, you should do the same.

What industries do you understand better than most investors? What communities do you have access to? What problems have you experienced personally that you know need solving?

That's where you should focus your investments. Not on competing for the same hot deals that every other investor is chasing.

2. Thesis-driven investing beats spray-and-pray

Serena has a clear investment thesis focused on underrepresented founders. This helps her say no to deals that don't fit, even if they look promising on paper.

As angel investors, we need similar discipline. It's tempting to invest in every interesting company we see. But having a clear thesis helps us make better decisions and build more coherent portfolios.

3. Access to differentiated deal flow matters more than you think

VCs talk about this all the time, but it applies to angels too. If you're seeing the same deals as everyone else, you're probably overpaying and facing too much competition.

Serena gets unique deal flow because of who she is and the networks she's built. We need to think creatively about how we can access deal flow that others don't see.

Maybe it's through industry-specific communities. Maybe it's through geographic focus. Maybe it's through relationships with accelerators or other investors. The point is to cultivate sources of deal flow that aren't obvious to everyone.

4. Long-term thinking beats short-term optimization

Serena isn't trying to flip companies for quick returns. She's building relationships with founders and supporting them over multiple funding rounds.

This long-term approach makes her a more attractive investor to founders. And it leads to better outcomes because she's not pressuring companies to optimize for the wrong metrics.

The diversity thesis: charity or alpha?

Let's address the elephant in the room. Some people dismiss Serena's focus on underrepresented founders as politically correct virtue signaling rather than sound investment strategy.

This is lazy thinking.

The diversity thesis isn't about charity. It's about recognizing market inefficiencies and exploiting them. When capital systematically flows away from certain types of founders, it creates opportunities for investors who are willing to evaluate those founders objectively.

Research backs this up. A study by the Kauffman Foundation found that companies with at least one female founder performed 63% better than all-male founding teams. But female founders receive a fraction of the capital.

That's not a charity case. That's a market inefficiency.

Serena's impact beyond just capital

Here's something that separates great investors from merely good ones: the value they provide beyond the check they write.

Serena brings unique advantages to her portfolio companies:

Brand association: Having Serena Williams as an investor opens doors. It signals legitimacy and attracts attention from customers, press, and other investors.

Strategic advice on building brands: Serena has built one of the most valuable personal brands in sports history. She understands how to tell stories, build communities, and create emotional connections with audiences. This expertise is incredibly valuable for consumer-facing companies.

Resilience and performance mindset: Nobody understands pressure and performance like a professional athlete at Serena's level. She can help founders navigate the mental challenges of building companies and performing under stress.

Network effects: Serena has relationships across sports, entertainment, business, and culture. These connections can help portfolio companies with partnerships, customer acquisition, and talent recruitment.

This is a good reminder for all early-stage investors: the money matters, but the value you provide beyond the money often matters more.

Portfolio construction lessons from Serena Ventures

Looking at the breadth of Serena Williams investments, you can see thoughtful portfolio construction:

Stage diversification: She invests across pre-seed, seed, and later stages. This provides exposure to different risk/return profiles.

Sector diversification: The portfolio spans fintech, consumer, healthcare, enterprise software, and more. She's not overly concentrated in any single sector.

Thesis consistency with tactical flexibility: Most investments align with the core thesis around underrepresented founders. But she's willing to make opportunistic bets outside that focus when the opportunity is compelling enough.

For angel investors, this suggests we should have a clear thesis but maintain some flexibility for exceptional opportunities that fall outside our primary focus areas.

What's next for Serena Ventures?

Serena has indicated she plans to raise additional funds and scale her investment platform. The question is whether she can maintain her edge as the fund grows.

This is a common challenge in venture capital. What works at small scale doesn't always work at large scale. Unique deal flow becomes harder to find. Decision-making slows down. The temptation to compete for the same deals as everyone else increases.

But if anyone can navigate this transition, it's probably someone who spent two decades performing at the highest level under intense pressure.

The bottom line for angel investors

Serena Williams' approach to venture capital offers several lessons for early-stage investors. Focus on areas where you have unique insights and access. Build a clear investment thesis and stick to it. Think long-term rather than optimizing for quick flips. And provide value beyond just capital.

Most importantly, recognize that your differences are advantages, not obstacles. The things that make you different from typical VCs or angel investors are probably the things that will make you successful.

Looking to connect with other investors who share this operator-turned-angel mindset? Angel Squad brings together a community of early-stage investors who focus on being genuinely helpful to founders while building thoughtful portfolios. We're operators who understand what founders need because we've been in their shoes, and we work together to get access to Hustle Fund's best deals.

Whether you're writing $25k checks or $250k checks, the principles remain the same. Find your edge. Build relationships with great founders. Stay disciplined. And remember that the best investments often come from places where others aren't looking.

That's what Serena's success as an investor teaches us. And it's something every angel investor should take to heart.