Serena Williams has spent the better part of the past two decades dominating the world of women's tennis. But even she can't defeat Father Time. Next year will be her 25th as a professional. While Williams remains at the very top of her sport, it's an inescapable fact that, with every tournament, her career on the court is inching ever closer to its inevitable denouement.

What's next? Lots of things, probably. Williams is a superstar athlete, sure. But she's also an author, fashion designer, actress and activist. In 2017, she gave birth to her first child. She has always stayed busy. And in recent years, Williams has been focused more and more on a side gig that seems to be attracting more and more star athletes: investing as a venture capitalist.

This April, she officially unveiled Serena Ventures, a firm that's been operating in stealth since way back in 2014. In the time since, it's built a portfolio that includes some of the hottest tech startups in Silicon Valley. The eponymous firm has also established some of the outlines of its strategy: It's displayed a clear pattern of investing in companies that are led by women or provide products aimed primarily at women, and it's also been active backing companies in the retail and food sectors.

Let's take a closer look at what sorts of businesses are drawing the attention of the tennis legend.
 
Williams in 2015, keeping her eye on the ball. (Tatiana/CC BY-SA 2.0)

Women investing in women

The clearest trendline emerging in Serena Ventures' activity is a desire to challenge the gender gap in VC by investing in the sorts of companies and founders that have far too often been overlooked or avoided by the old boy's club of Silicon Valley.

That includes names like The Wing, an operator of co-working spaces and social clubs aimed at women that's raised more than $100 million in VC funding to date, reaching a $375 million valuation last December. Founded in 2016 by Audrey Gelman and Lauren Kassan, the business claims an illustrious string of backers in addition to Serena Ventures, including Sequoia, Airbnb, WeWork and several members of the US women's national soccer team.

Williams and her firm are also investors in Billie, another female-founded company that sells razors and other body-care products aimed at women. It raised a $25 million round in January. Lola, which delivers tampons, pads and other reproductive healthcare products to women, is also part of the Serena Ventures portfolio; it raised a reported $24 million during 2018 at a $104 million valuation.

The list goes on. Floravere has raised cash from Serena Ventures to support its business of selling wedding dresses directly to consumers. Mayvenn has brought in funding from the firm to support its hair extensions and other beauty products. And HoneyLove has turned to the firm to back its line of shapewear for women.

A seat at the table

Serena Ventures is also clearly interested in the future of food. By far the biggest name it's backed in the space is Impossible Foods, a maker of plant-based protein products that raised $300 million this May at a $2 billion valuation—a round that closed as one of the company's biggest rivals, Beyond Meat, was seeing its stock price skyrocket after a red-hot IPO.
 
The Impossible Burger in action (Courtesy of Impossible Foods)

The firm is also an investor in multiple meal delivery companies. One is Daily Harvest, which provides fresh fruits, vegetables and other organic ingredients to customers on a weekly or monthly basis. Another is Gobble, which delivers meal kits that are designed to be able to be prepared in 15 minutes or less. That particular deal is an example of Serena Ventures keeping its business in the family: Gobble is also backed by Initialized Capital, the firm led by Alexis Ohanian, Williams' husband and a co-founder of Reddit.

For smaller stomachs, Serena Ventures is a backer of Little Spoon, which runs a delivery service for organic baby food. For canine stomachs, the firm is an investor in Ollie, a provider of customized meal plans for dogs. And for the wellness-inclined, there's the similarly named Olly, a seller of vitamins, protein bars and related products.

Reaching into retail

Williams has long been linked to the world of fashion, both on and off the court. Her tennis attire has made headlines throughout her career, including a skin-tight black catsuit she donned at the 2018 French Open that was subsequently banned by the French Tennis Federation. And Williams is also a designer in her own right, including her own lines of sportswear, eveningwear and handbags.

That interest has manifested in some of Serena Ventures' investments. The firm is a backer of Rockets of Awesome, which makes bright and flashy clothes for kids, as well as Neighborhood Goods, an emerging department store chain that sells apparel from a rotating group of different brands, many of them born on the internet. Last year, Williams launched her latest clothing line at the company's flagship store in Plano, TX.

Serena Ventures is also an investor in Brandless, a paradoxically named company that sells a range of  food, household goods and other products under its own label. Last summer, the company pulled in a $240 million investment led by the SoftBank Vision Fund. And just last month, Serena Ventures took part in a $9.6 million funding for Retail Zipline, a developer of tools that help retail stores improve their communication with upper management, valuing the business at $38.4 million.

The best of the rest

It doesn't fit neatly into any of the above categories, but we'd be remiss not to mention that Serena Ventures holds a stake in Coinbase, a breakout star of the bitcoin era that was valued at more than $8 billion last October. Williams' investment wasn't publicly known until she announced the launch of her namesake firm this April. That same month, Serena Ventures backed a $45 million Series C for Tonal, a Peloton-type company that sells a wall-mounted fitness system and screen rather than a stationary bike—the sort of company you might expect a professional athlete to invest in.

The firm's other notable portfolio companies include MasterClass, which sells online classes in a variety of disciplines; Williams herself offers a tennis lesson on the site. There's also Andela, which was valued at $700 million in January. The startup operates mainly in Africa, working to connect software developers from the continent with tech companies around the world. Last but not least, Williams sits on the board of directors at SurveyMonkey, which makes software for online surveys.

Taken as a whole, it's a big enough collection of companies to keep any venture firm busy. Let alone one that's led by a woman whose primary job is still winning Grand Slams.

Featured image via Roberto Faccenda/CC BY-SA 2.0

*This article has been updated to more accurately describe Brandless' range of products. 
 

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