In a changed VC landscape, this exec is doubling down on overlooked founders

For years, much of Silicon Valley has been consumed by mega-rounds and the loudest AI deals. Stacy Brown-Philpot is taking a different approach. Through Cherryrock Capital, she’s leaning into a more old-school venture style — writing smaller Series A and Series B checks for founders that bigger firms routinely pass over.

The former TaskRabbit CEO and longtime Google executive launched Cherryrock a year ago after noticing what she describes as a stubborn, persistent gap: growth-stage funding for “underinvested entrepreneurs” building software companies at the moment when access to capital can make or break momentum.

“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-Philpotsaidd. She first moved to the Bay Area 25 years ago with the intention of becoming a VC, even writing about that goal in her Stanford Business School essay. After a decade at Google and then leading TaskRabbit through its successful exit to IKEA, she’s now returned to the path she originally set out to follow.

She came back to it with a specific reason. Before starting Cherryrock, Brown-Philpot served on the investment committee for the SoftBank Opportunity Fund, a $100 million fund created in 2020 to back underserved entrepreneurs. That work convinced her the issue wasn’t a lack of talent or companies — it was the lack of capital reaching overlooked founders.

SoftBank sold the Opportunity Fund to its leadership team in late 2023, stepping away from the diversity-focused effort. Brown-Philpot moved in the opposite direction. She doubled down and launched her own fund. By the time she closed Cherryrock’s first fund in February 2025, she already had more than 2,000 companies in her pipeline.

Cherryrock is aiming for 12 to 15 investments from the debut fund — a concentrated strategy that stands in clear contrast to seed funds that place dozens of smaller bets or giant firms that can write nine-figure checks. Brown-Philpot is also deliberately moving at a slower pace. A year after announcing the fund, she and her team — including cofounder Saydeah Howard, who spent nine years at venture firm IVP — have backed only five companies, putting them around a third of the way toward their target. In a market where many funds rush to deploy capital quickly after raising it, her measured pace feels like another throwback to an earlier venture playbook.

Her focus on “underinvested” founders — language chosen carefully in today’s political climate — centres on entrepreneurs who may not match the standard Silicon Valley mould.

When asked directly about the current political environment, where DEI has turned into a flashpoint, Brown-Philpot doesn’t appear rattled. “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 that expect to generate a return. Our job as investors is to do just that.”

Alongside those backers, Cherryrock’s limited partners include Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates’s Pivotal Ventures. Some of those institutions have scaled back explicit diversity commitments amid pressure from the Trump administration. Even so, Brown-Philpot may end up in an unexpectedly favourable position.

A new diversity reporting law in California requires VC firms with a California nexus to report demographic information on the founding teams of their portfolio companies, with the first deadline arriving in April. The law is structured around transparency rather than mandates, requiring reporting but not quotas — a key distinction from some corporate diversity initiatives that have faced legal challenges. For a firm like Cherryrock, which already tracks and prioritises investments in diverse founders, compliance is “table stakes,” as Brown-Philpot puts it. “You accomplish what you measure.”

Brown-Philpot’s outlook is shaped by her vantage point across multiple institutions. In addition to running Cherryrock, she sits on the boards of HP, StockX, and Stanford University — roles that give her a direct window into enterprise buyers, consumer trends, and the next generation of founders. At Stanford, she’s watching students work through questions about how AI will reshape 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 in action. 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 media and entertainment—a sector facing heightened 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. Based in Philadelphia, the company offers on-demand, primary care-based health insurance for employers and hourly workers — a population Brown-Philpot came to know well during her final years leading TaskRabbit as an independent 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.” She first invested in Vitable at the seed stage through her work with the SoftBank Opportunity Fund.

When asked about her operating philosophy, Brown-Philpot is notably direct about exits. “It’s very difficult to go public,” she said. “Most companies don’t go public; they do  get acquired.” It’s a clear-eyed view in an industry that often sells big IPO dreams. She points to TaskRabbit’s sale to IKEA as evidence that the right acquisition can still create long-term value.

Looking ahead to 2026, Brown-Philpot says the priority is straightforward: “We are actively deploying capital.” She’s focused on Series A and B companies that have reached product-market fit at scale, while letting founders define what that means for their businesses. And as the broader venture world debates the future of diversity initiatives, she’s staying locked in on her core work — finding strong founders, wherever they are. “I’m from Detroit,” she says. “Hard things are hard, but we know how to do hard things.”