Much of Silicon Valley has spent years pursuing large rounds and active AI deals. Meanwhile, Stacy Brown-Philpot runs Cherryrock Capital like a throwback to the early days of venture capital, writing small Series A and B checks to founders routinely overlooked by larger companies.
The former CEO of TaskRabbit and a 10-year Google veteran founded Cherryrock a year ago after seeing what she called a persistent gap. Access to capital for “underinvested entrepreneurs” building software companies at critical stages of growth.
“When I left TaskRabbit, I took some time to figure out what my next steps were, and I saw a gap in the market for access to capital, especially for underinvested entrepreneurs,” Brown-Philpot told TechCrunch. She originally planned to become a VC when she came to the Bay Area 25 years ago, even writing an essay for Stanford Business School about it. After 10 years at Google and successfully leading TaskRabbit to IKEA, she finally returned to her original plan.
She went back there for a reason. Before launching Cherryrock, Brown-Philpot was a member of the Investment Committee of the SoftBank Opportunity Fund, a $100 million vehicle launched in 2020 to support underrepresented entrepreneurs. The experience proved that there is no shortage of overlooked founders.
SoftBank is moving away from diversity-focused initiatives and selling its Opportunity Fund to its leadership team in late 2023. Meanwhile, Brown-Philpot doubled down and launched his own fund. By the time she closed Cherryrock’s debut fund in February 2025, she already had over 2,000 companies in her pipeline.
Cherryrock is targeting 12 to 15 investments in its first fund. This is a focused approach that stands in sharp contrast to seed funds that place dozens of bets or larger funds that write nine-figure checks. Brown-Philpot is also taking her time. A year after announcing the fund, she and her team, which includes co-founder Saydeah Howard, who spent nine years at venture firm IVP, have backed just five companies and are about a third of the way to their goal. In an era where many funds compete to deploy capital as quickly as they raise it, Brown-Philpot’s measured speed is another throwback to previous generations of VCs.
Brown-Philpot’s focus on “underinvested” founders (a word she chooses carefully in today’s political climate) means supporting entrepreneurs who may not fit the typical Silicon Valley mold.
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When asked directly about the current political climate in which DEI has become a lightning rod, Brown-Philpot was unfazed. “The pitch doesn’t change at all,” she said. “If you look at the people who have decided to support Cherryrock, like JPMorgan and Bank of America… these are financial institutions that expect to generate revenue. As investors, our job 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 of them have backed away from explicit diversity commitments under pressure from the Trump administration. But Brown-Philpot may have an unexpected advantage.
California’s new diversity reporting law requires VC firms with California ties to report demographic data on the founding teams of their portfolio companies by the first deadline in April. Unlike some corporate diversity initiatives that have faced legal challenges, the law focuses on transparency rather than mandates and requires reporting but not quotas. For companies like Cherryrock, which already tracks and prioritizes investments in diverse founders, compliance is, as Brown-Philpot puts it, “table stakes.” “You achieve what you measure up to.”
Brown-Philpot’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 into both corporate buyers and next-generation entrepreneurs. At Stanford, she watches students explore questions about the impact of AI on employment. “What I see on campus is students finding ways to plan their careers and create opportunities for themselves,” she said.
Her portfolio reflects her thesis. One of the investments is Coactive AI, led by Cody Coleman, an MIT graduate who holds advanced degrees in philosophy and engineering from MIT and Stanford. The company provides multimodal AI infrastructure to the media and entertainment industry, a sector currently under intense scrutiny due to controversy over AI-generated content. Cherryrock led Coactive’s Series B with Emerson Collective.
Another investment is Vitable Health, founded by Thiel Fellow and Y Combinator graduate Joseph Kitonga. The Philadelphia-based company provides on-demand primary care-based health insurance to employers and hourly workers. Brown-Philpot is an independent company and is someone I have come to know well as CEO of TaskRabbit over the past few years. Kitonga is “exactly the kind of founder we want to support,” Brown-Philpot said. “He does what he says he will do.” Brown-Philpot first invested in Vitable’s seed stage through its work with SoftBank Opportunity Fund.
When asked about her operating philosophy, Brown-Philpot said she is pragmatic about exits. “It’s very difficult to go public,” she said. “Most companies are acquired rather than listed.” It’s a refreshingly honest look at an industry that often overpromises on IPO prospects. She points to TaskRabbit’s sale of IKEA as evidence that the right acquisitions can create lasting value.
Brown-Philpot’s priorities for 2026 are simple. “We are actively deploying capital.” She is looking for Series A and B companies that have achieved product-market fit at scale, allowing founders to define what that means. While discussing the future of diversity initiatives in the broader venture ecosystem, she focuses on finding great founders wherever they are.
“I’m from Detroit,” she says. “Hard things are hard, but we know how to do hard things.”
