Much of Silicon Valley has spent years chasing big rounds and buzzy AI deals. Meanwhile, Stacy Brown-Philpot runs Cherryrock Capital like a throwback to the earlier days of venture capital, writing smaller Series A and B checks to founders who are often overlooked by larger firms.
The former TaskRabbit CEO and decade-long Google veteran launched Cherryrock a year ago after seeing what he calls a persistent gap: access to capital for “underinvested entrepreneurs” building early-stage software companies.
“When I left TaskRabbit, I took some time to figure out what was next, and I saw this gap in the market, which was access to capital, particularly for entrepreneurs who didn’t have investment,” Brown-Philpot told TechCrunch. She had originally come to the Bay Area 25 years ago, planning to become a VC and even writing her Stanford Business School essay about it. After spending a decade at Google and leading TaskRabbit to a successful exit from IKEA, he finally returned to that original plan.
He went back to it for a reason. Prior to 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 underserved entrepreneurs. This experience proved that there was no shortage of overlooked founders.
SoftBank itself sold the Opportunity Fund to its leadership team in late 2023, divesting from the diversity-focused initiative. Brown-Philpot, meanwhile, doubled down and launched her own fund. When Cherryrock’s debut fund closed in February 2025, it already had more than 2,000 companies in its pipeline.
Cherryrock is targeting 12 to 15 investments from its first fund — a focused approach and a stark contrast to seed funds that make dozens of bets or mega funds that write nine-figure checks. Brown-Philpot is also taking her time. A year after announcing the fund, she and her team, including co-founder Saydeah Howard, who spent nine years at venture capital firm IVP, have backed just five companies, putting them about a third of the way to their goal. At a time when many funds struggle to deploy capital nearly as fast as they raise it, Brown-Philpot’s measured pace is another throwback to an earlier generation of VCs.
Brown-Philpot’s focus on uninvested founders — a careful choice of words in today’s political climate — means supporting entrepreneurs who might not fit the typical Silicon Valley mold.
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When asked directly about today’s political environment, where PPC has become a lightning rod, Brown-Philpot remains unfazed. “It doesn’t change the playing field at all,” he said. “When we look at the people who have decided to back Cherryrock, like JPMorgan and Bank of America … these are financial institutions that expect to make a profit. 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 of them have backed away from clear commitments to diversity amid pressure from the Trump administration. However, Brown-Philpot may find itself in an unexpectedly advantageous position.
A new one diversity reporting law in California requires VC firms with ties to California to report demographic data on the founding teams of their portfolio companies, with the first deadline in April. Unlike some corporate diversity initiatives that have faced legal challenges, the law it focuses on transparency rather than mandates, requiring reporting but not quotas. For a company like Cherryrock that already tracks and prioritizes investments across founders, compliance is “table stakes,” as Brown-Philpot puts it. “You get what you measure.”
Brown-Philpot’s perspective is shaped by her advantage in many institutions. Beyond Cherryrock, she sits on the boards of HP, StockX, and Stanford University — roles that give her insight into both business buyers and the next generation of founders. At Stanford, he watches students explore questions about the impact of artificial intelligence on employment. “What I see on campus is students charting a path and finding a way to create opportunities for themselves,” he said.
Her portfolio reflects her thesis. One 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 to the media and entertainment industry, a sector now under intense scrutiny following controversy surrounding AI-generated content. Cherryrock led Coactive’s Series B alongside Emerson Collective.
Another bet is Sustainable Healthfounded by Thiel Fellow and Y Combinator Joseph Kitonga. The Philadelphia-based company provides on-demand, primary care-based health insurance to employers and hourly workers – the kind of population Brown-Philpot has gotten to know well as CEO of TaskRabbit over the past few years as a standalone company. Kitonga “is exactly the kind of founder we want to support,” Brown-Philpot said. “It does what it says it’s going to do.” Brown-Philpot first invested in Vitable’s early stage through its partnership with the SoftBank Opportunity Fund.
When asked about her operating philosophy, Brown-Philpot is realistic about exits. “It’s very difficult to come out in public,” she said. “Most companies don’t go public, they get bought out.” It’s a refreshingly candid take on an industry that often overpromises about 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 developing capital.” It looks for Series A and B companies that have achieved product-to-market fit at scale, leaving the founders to define what that means. And while the broader business ecosystem debates the future of diversity initiatives, this one is focused on finding great founders, wherever they are.
“I’m from Detroit,” he says. “Hard things are hard, but we know how to do hard things.”
