Many people in Silicon Valley have spent years chasing mega-rounds and hot AI deals. Stacey Brown Philpott, meanwhile, runs CherryRock Capital like she was back in the early days of venture capital, writing small Series A and B checks to founders routinely overlooked by larger companies.
The former TaskRabbit CEO and 10-year Google veteran launched Cherryrock a year ago after seeing what she called a persistent gap in access to capital for “underinvested entrepreneurs” building software companies at critical growth stages.
“When I left TaskRabbit, I took some time to think about what to do next and realized a gap in the market, particularly the issue of access to capital for underinvested entrepreneurs,” Brown-Philpot told TechCrunch. She originally came to the Bay Area 25 years ago with plans to become a venture capitalist and even wrote an essay for Stanford Business School about it. After 10 years at Google and the successful exit of TaskRabbit to IKEA, she finally returned to her original plan.
She went back for a reason. Before launching CherryRock, Brown-Philpott was a member of the investment committee of the SoftBank Opportunity Fund, a $100 million fund established in 2020 to support underserved entrepreneurs. This experience proved that there is no shortage of overlooked founders.
SoftBank itself sold the Opportunity Fund to management at the end of 2023, separating it from its diversity-focused efforts. Meanwhile, Brown-Philpott has stepped up his game and launched his own fund. By the time she closed CherryRock's debut fund in February 2025, she already had more than 2,000 companies in the pipeline.
CherryRock aims to make 12 to 15 investments from its first fund, a focused approach that stands in stark contrast to seed funds that make dozens of bets or large funds that write nine-figure checks. Brown-Philpott is also taking his time. A year after announcing the fund, she and her team, including co-founder Cydia Howard, who spent nine years at venture firm IVP, have backed just five companies, about a third of the way to their goal. In an era when many funds compete to deploy capital nearly as quickly as they raise money, Brown Philpott's measured pace is another throwback to previous generations of VCs.
Brown Philpott's focus on “underinvested” founders means supporting entrepreneurs who may not fit the typical Silicon Valley mold, choosing his words carefully in today's political climate.
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When asked directly about the current political environment in which DEI has become a lightning rod, Brown-Philpott was unfazed. “The pitch hasn’t changed at all,” she said. “If you look at the people who decided to back Cherry Rock, like JPMorgan and Bank of America…these are financial institutions that expect to generate profits. Our job as investors is to do just that.”
In addition to these investors, Cherryrock's LP roster includes Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates' Pivotal Ventures. Some have backed away from explicit diversity pledges under pressure from the Trump administration. But Brown-Philpott may have an unexpected advantage.
California's new diversity reporting law requires VC firms affiliated with California to report demographic data on the founding teams of their portfolio companies, with an initial deadline of April. Unlike some corporate diversity efforts that have faced legal challenges, the law focuses on transparency rather than mandates, requiring reporting but not quotas. For companies like CherryRock, which already tracks and prioritizes investments in diverse founders, compliance is, as Brown-Philpott puts it, “a stake.” “You achieve what you measure.”
Brown Philpott's perspective is informed by her vantage point across multiple institutions. In addition to Cherryrock, she serves on the boards of HP, StockX, and Stanford University, providing insight to both enterprise buyers and the next generation of founders. At Stanford University, students are watching as they answer questions about the impact of AI on employment. “What we see on campus is students charting paths and finding ways to create opportunities for themselves,” she says.
Her portfolio reflects her thesis. One of the investments is Coactive AI, led by Cody Coleman, an MIT alumnus who earned advanced degrees in philosophy and engineering from MIT and Stanford. The company provides multimodal AI infrastructure to the media and entertainment industry. The industry is currently under intense scrutiny following controversy surrounding AI-generated content. Cherry Rock led Co-Active's Series B with Emerson Collective.
Another bet is Vitable Health, founded by Thiel fellow and Y Combinator alum Joseph Kitonga. The Philadelphia-based company provides on-demand, primary care-based health insurance to employers and hourly workers. Brown-Philpott is a group of people I knew well as TaskRabbit's CEO during its last years as an independent company. Mr. Kitonga is “exactly the kind of founder we want to support,” Mr. Brown-Philpott said. “He does what he says he's going to do.'' Brown-Philpot first invested in Vitable's seed stage through his work with SoftBank Opportunity Fund.
When asked about his business philosophy, Brown-Philpott is pragmatic about exits. “It's a very difficult thing to publish,” she says. “Most companies don't go public, they get acquired.” This is a refreshingly honest view of an industry that often overpromises the prospect of an IPO. She points to the sale of TaskRabbit to IKEA as proof that the right acquisition can create lasting value.
For 2026, Brown Philpott's priorities are simple. This means “actively investing capital.” She looks for Series A and B companies that have achieved product-market fit at scale and let their founders define what that means. And while the broader venture ecosystem debates the future of diversity efforts, she's focused on finding great founders everywhere.
“I’m from Detroit,” she says. “Difficult things are difficult, but we know how to do difficult things.”