Most of Silicon Valley has been chasing mega-rounds and buzzy AI deals for years. Meanwhile, Stacy Brown-Philpot runs Cherryrock Capital like a throwback to the venture capital days of yesteryear, writing smaller Series A and B checks to founders that big firms ignore.
The former CEO of TaskRabbit and a decade-long Google veteran launched Cherryrock a year ago after seeing what he called a persistent gap: access to capital for “underinvested entrepreneurs” building software companies at a critical growth stage.
“When I left TaskRabbit, I took some time to figure out what’s next and see this gap in the market, which is access to capital, especially for underinvested entrepreneurs,” Brown-Philpot told TechCrunch. He originally came to the Bay Area 25 years ago, intending to become a VC and even wrote a Stanford Business School essay about it. After spending ten years at Google and successfully leading TaskRabbit to IKEA, he finally returned to the original plan.
He circled back for a reason. Before launching Cherryrock, Brown-Philpot was a member of the investment committee for the SoftBank Opportunity Fund, a $100 million vehicle launched in 2020 to support underprivileged entrepreneurs. The experience proved that no lack of founders was overlooked.
SoftBank itself is selling its Opportunity Fund to its leadership team at the end of 2023, scrapping initiatives focused on diversity. Brown-Philpot, meanwhile, doubled down, and opened his own fund. When he closed his debut fund Cherryrock in February 2025, he already had more than 2,000 companies in the pipeline.
Cherryrock is targeting 12 to 15 investments from the first fund – a concentrated approach and in stark contrast to seed funds that make dozens of bets, or massive funds that write nine-figure checks. Brown-Philpot also took her time; a year after announcing the fund, he and his team, including cofounder Saydeah Howard, who spent nine years at venture firm IVP, have backed just five companies, putting about a third toward their goal. In an era when many funds are racing to deploy capital almost as quickly as they raise it, Brown-Philpot’s measured move is a step back for previous generations of VCs.
Brown-Philpot’s focus on “underinvested” founders — a careful choice of words in the current political climate — means backing entrepreneurs who may not fit the typical Silicon Valley mold.
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When asked directly about the current political environment, in which DEI has become a lightning rod, Brown-Philpot is not surprised. “It doesn’t change the pitch at all,” she said. “When we see people who decide to support Cherryrock, like JPMorgan and Bank of America … these are financial institutions that expect returns. Our job as investors is to do that.”
In addition to these investors, Cherryrock’s LP roster includes Goldman Sachs Asset Management, MassMutual, Top Level Capital Partners, and Melinda Gates’ Pivotal Ventures. Some of these have backed away from clear promises of diversity amid pressure from the Trump administration. But Brown-Philpot may be in an unlikely position.
A new diversity reporting law in California requires VC companies with a California nexus to report demographic data on the founding team of portfolio companies, with the first deadline in April. Unlike some corporate diversity initiatives that face legal challenges, the law focus on transparency rather than mandates, requiring reporting but not quotas. For a firm like Cherryrock that has been tracking and prioritizing investments in various founders, aligned “table tattoos,” as Brown-Philpot put it. “You accomplish what you measure.”
Brown-Philpot’s perspective is informed by her perspective on many institutions. Beyond Cherryrock, he sits on the boards of HP, StockX, and Stanford University – roles that provide insight into the next generation of corporate buyers and founders. At Stanford, he watched students explore questions about AI’s impact on the workplace. “What I see on campus is that students are making their own way and finding ways to create opportunities for themselves,” he said.
Her portfolio reflects her thesis. One such investment is Coactive AI, led by Cody Coleman, an MIT graduate with advanced degrees in philosophy and engineering from MIT and Stanford. The company provides multimodal AI infrastructure for the media and entertainment industry, a sector currently under scrutiny following controversy over AI-generated content. Cherryrock led Coactive’s Series B alongside Emerson Collective.
the other bet is Vital Healthfounded by Joseph Kitonga, Thiel Fellow and Y Combinator alum. The Philadelphia-based company provides primary care-based health insurance for employers and hourly workers — the kind of population Brown-Philpot knows well as CEO of TaskRabbit during its last years as an independent company. Kitonga “is the type of fit we want to get back,” Brown-Philpot said. “He did what he said he was going to do.” Brown-Philpot first invested in the seed stage of Vitable through his work with the SoftBank Opportunity Fund.
When asked about her operating philosophy, Brown-Philpot was pragmatic about her exit. “It’s very difficult to go public,” he said. “Most companies don’t go public, they earn.” It’s a refreshingly honest take on an industry that often overpromises on IPO prospects. He points to the sale of TaskRabbit to IKEA as proof that the right acquisition can create lasting value.
As for 2026, Brown-Philpot’s priority is simple: “We are actively using capital.” They look for Series A and B companies that have achieved product-market fit at scale, allowing founders to define what that means. And while the broader venture ecosystem debates the future of diversity initiatives, they’re focused on finding great founders, wherever they are.
“I’m from Detroit,” she said. “Difficult things are difficult, but we know how to do difficult things.”