Much of Silicon Valley has spent years chasing mega-rounds and buzzy AI deals. Meanwhile, Stacy Brown-Philpot is running Cherryrock Capital like a throwback to venture capital’s earlier days, 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 crucial 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, particularly for underinvested entrepreneurs,” Brown-Philpot told TechCrunch. She’d 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 to IKEA, she’s finally back to that original plan.

She circled back to it for a reason. Before launching Cherryrock, Brown-Philpot was a member of the investment committee for the SoftBank Opportunity Fund, a $100 million vehicle started in 2020 to back underserved entrepreneurs. That experience proved 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. By the time she closed Cherryrock’s debut fund in February 2025, she already had more than 2,000 companies in her pipeline. 

Cherryrock is targeting 12 to 15 investments from its first fund — a concentrated approach and stark contrast to the seed funds that make dozens of bets, or massive funds that write nine-figure checks. Brown-Philpot’s also taking her time; a year after announcing the fund, she and her team, including cofounder Saydeah Howard, who spent nine years at the venture firm IVP, have backed just five companies, putting them about a third of the way toward their goal. In an era when many funds race 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 backing entrepreneurs who might not fit the typical Silicon Valley mold.

When asked directly about the current political environment, where DEI has become a lightning rod, Brown-Philpot is unfazed. “It doesn’t change the pitch 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 who expect to generate a return. Our job as investors is to do just that.”

In addition to those investors, Cherryrock’s LP roster includes Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates’s Pivotal Ventures. Some of these have stepped back from explicit diversity pledges amid pressure from the Trump administration. Yet Brown-Philpot may find herself in an unexpectedly advantageous position. 

A new diversity reporting law in California requires VC firms with a California nexus to report demographic data on their portfolio companies’ founding teams, with 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 firm like Cherryrock that’s already tracking and prioritizing investments in diverse founders, compliance is “table stakes,” as Brown-Philpot puts it. “You accomplish what you measure.”

Brown-Philpot’s perspective is informed by her vantage point across multiple institutions. Beyond Cherryrock, she sits on the boards of HP, StockX, and Stanford University — roles that give her insight into both enterprise buyers and the next generation of founders. At Stanford, she’s watching students navigate questions about AI’s impact on employment. “What I see on campus is the students are charting 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 grad 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 controversies around AI-generated content. Cherryrock led Coactive’s Series B alongside Emerson Collective.

Another bet is Vitable Health, founded by Joseph Kitonga, a Thiel Fellow and Y Combinator alum. The Philadelphia-based company provides on-demand, primary care-based health insurance to employers and hourly workers – the kind of population Brown-Philpot came to know well as the CEO of TaskRabbit during its last years as a standalone company. Kitonga “is the exact kind of founder that we want to back,” Brown-Philpot said. “He does what he says he’s going to do.” Brown-Philpot first invested at 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 do get acquired.” It’s a refreshingly honest take in an industry that often overpromises on 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 are actively deploying capital.” She’s looking for Series A and B companies that have achieved product-market fit at scale, letting founders define what that means. And while the broader venture ecosystem debates the future of diversity initiatives, she is 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.”