Much of Silicon Valley has spent years chasing mega-rounds and busy AI deals. Meanwhile, Stacy Brown-Philpot runs Cherryrock Capital as a throwback to the earlier days of venture capital, writing smaller Series A and B checks to founders that larger firms routinely overlook.
The former TaskRabbit CEO and decade-long Google veteran launched Cherryrock a year ago after seeing what she calls a persistent gap: access to capital for “underinvested entrepreneurs” building software companies at the critical growth stage.
“When I left TaskRabbit, I took some time off to figure out what was next and saw this gap in the market, which was access to capital, especially for underinvested entrepreneurs,” Brown-Philpot told TechCrunch. She originally came to the Bay Area 25 years ago, planned to become a VC and even wrote her Stanford Business School essay about it. After spending a decade at Google and leading TaskRabbit to a successful exit to IKEA, she’s finally back to the original plan.
She circled back to it for a reason. Prior to 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 underserved entrepreneurs. That experience showed that there was no shortage of overlooked founders.
SoftBank itself sold the Opportunity Fund to its management team in late 2023, divesting the diversity-focused initiative. Brown-Philpot, meanwhile, doubled down and launched her own fund. When she closed Cherryrock’s debut fund in February 2025, she already had more than 2,000 companies in her pipeline.
Cherryrock is aiming for 12 to 15 investments from its first fund — a concentrated approach and a stark contrast to seed funds that make dozens of bets or massive funds that write nine-figure checks. Brown-Philpot also takes her time; a year after announcing the fund, she and her team, including co-founder Saydeah Howard, who spent nine years at venture firm IVP, have backed just five companies, putting them about a third of the way toward their goal. In an era where many funds struggle to deploy capital almost as quickly as it’s raised, Brown-Philpot’s measured pace is another throwback to an earlier generation of VCs.
Brown-Philpot’s focus on “underinvested” 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 the current political environment in which DEI has become a lightning rod, Brown-Philpot is unfazed. “It doesn’t change the trajectory at all,” she said. “When we look at the people who decided to back Cherryrock, like JPMorgan and Bank of America… these are financial institutions that expect to generate a return. 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 these have backed away from explicit promises of diversity under pressure from the Trump administration. Still, Brown-Philpot may find herself in an unexpectedly advantageous position.
A new California diversity reporting law requires VC firms with a California connection to report demographic data on their portfolio companies’ founding teams by the first deadline in April. Unlike some corporate diversity initiatives that have faced legal challenges, the law focuses on transparency rather than mandates requiring reporting but not quotas. For a company like Cherryrock, which already tracks and prioritizes investments in various founders, compliance is “table games,” as Brown-Philpot puts it. “You get what you measure.”
Brown-Philpot’s perspective is based on her vantage point across multiple institutions. In addition to Cherryrock, she serves on the boards of HP, StockX, and Stanford University—roles that give her insight into both corporate buyers and the next generation of founders. At Stanford, she sees students navigating questions about AI’s impact on employment. “What I see on campus is students carving out a path and finding a way to create opportunities for themselves,” she 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 for the media and entertainment industry, a sector now under intense scrutiny following controversies surrounding AI-generated content. Cherryrock co-led Coactive’s Series B with Emerson Collective.
Another effort is Vital Health, founded by Joseph Kitonga, a Thiel Fellow and Y Combinator alum. The Philadelphia-based company offers on-demand, primary health-based health insurance to employers and hourly workers — the type of population Brown-Philpot got to know well as CEO of TaskRabbit during its last years as a freelancer. Kitonga “is the exact kind of founder that we want to support,” Brown-Philpot said. “He does what he says he’s going to do.” Brown-Philpot first invested in the seed stage of Vitable through her work with the SoftBank Opportunity Fund.
When asked about her operating philosophy, Brown-Philpot is pragmatic about exits. “It’s very difficult to go public,” she said. “Most companies don’t go public, they get acquired.” It’s a refreshingly honest picture of an industry that often overpromises IPO prospects. She points to TaskRabbit’s sale to IKEA as proof that the right acquisition can create lasting value.
As for 2026, Brown-Philpot’s priority is simple: “We employ active capital.” She looks for Series A and B companies that have achieved product-market fit at scale and lets the founders define what that means. And while the broader venture ecosystem debates the future of diversity initiatives, she’s focused 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.”