In a changing venture capital landscape, this CEO is doubling down on overlooked founders

Many Silicon Valley insiders have spent years chasing mega-deals and buzzy AI deals. Meanwhile, Stacy Brown Philpott runs Cherryrock Capital like a throwback to the earlier days of venture capital, writing smaller Series A and B checks to founders who were routinely overlooked by larger firms.

The former CEO of TaskRabbit and a decade-long Google veteran launched Cherryrock a year ago after seeing what she calls a persistent gap: access to capital for “underinvested entrepreneurs” in building software companies at a crucial growth stage.

“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, especially for entrepreneurs who were underinvested,” Brown-Philpott told TechCrunch. She originally came to the Bay Area 25 years ago, planning to become a venture capitalist, and even wrote an essay on the subject for Stanford University Business School. After spending a decade at Google and leading TaskRabbit to a successful exit from IKEA, she finally returned to that original plan.

It came back to her for a reason. Before launching Cherryrock, Brown-Philpot was a member of the investment committee for SoftBank Opportunity Fund, a $100 million vehicle launched in 2020 to support disadvantaged entrepreneurs. This experience proved that there is no shortage of overlooked founders.

SoftBank itself sold the Opportunity Fund to its leadership team in late 2023, moving away from the diversity-focused initiative. Meanwhile, Brown-Philpot redoubled her efforts and launched her own fund. By the time it closed Cherryrock’s first fund in February 2025, it already had more than 2,000 companies in the 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 also takes her time; A year after announcing the fund, she and her team, including co-founder Lady Howard, who spent nine years at the venture firm’s IVP, have backed just five companies, putting them about a third of the way toward their goal. In an era when many funds are racing to deploy capital almost as quickly as they raise it, Brown-Philpot’s measured pace is another throwback to an earlier generation of venture capital funds.

Brown-Philpott’s focus on “non-investment” founders — a careful choice of words in today’s political climate — means backing entrepreneurs who may not fit the typical Silicon Valley mold.

When asked directly about the current political environment, where DEI has become a lightning rod, Brown-Philpott was unfazed. “It doesn’t change the playing field at all,” she said. “When we look at the people who have decided to back CherryRock, like JP Morgan and Bank of America… these are financial institutions that expect to deliver returns. Our job as investors is to do just that.”

In addition to these investors, Cherryrock’s LP list includes Goldman Sachs Asset Management, MasMutual, Top Tier Capital Partners, and Melinda Gates’ Pivotal Ventures. Some of them have backed away from their explicit pledges to diversity amid pressure from the Trump administration. However, Brown-Philpott may find itself in an unexpectedly advantageous position.

new Diversity Reporting Act In California, venture capital firms with a California connection are required to report demographic data on the founding teams of their portfolio companies, with the first deadline being in April. Unlike some corporate diversity initiatives that have faced legal challenges, the law It focuses on transparency rather than mandates, and requires reporting, not quotas. For a company like Cherryrock that already tracks and prioritizes investments in a diverse group of founders, compliance is “stakes on the table,” Brown-Philpott said. “You accomplish what you measure.”

Brown-Philpott’s perspective draws from her vantage point across many institutions. In addition to 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 University, she watches students answer 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,” she said.

Her portfolio reflects her thesis. One investment is Coactive AI, led by Cody Coleman, an MIT alumnus with advanced degrees in philosophy and engineering from MIT and Stanford. The company provides multimedia AI infrastructure for the media and entertainment sector, a sector that is now under intense scrutiny following controversy over AI-generated content. Cherryrock led Coactive’s Series B series alongside Emerson Collective.

The other bet is Vital healthfounded by Joseph Kitonga, a Thiel colleague and Y Combinator alumnus. The Philadelphia-based company provides on-demand primary care-based health insurance to employers and hourly workers — a demographic Brown-Philpott knew well when she was CEO of TaskRabbit during its final years as an independent company. Brown-Philpott said Kitonga is “exactly the kind of founder we want to support.” “He does what he says he’s going to do.” Brown-Philpot first invested in Vitable’s seed stage through its work with SoftBank Opportunity Fund.

When asked about her operating philosophy, Brown-Philpott was realistic about exits. “It’s very difficult to go public,” she said. “Most companies don’t go public, they get acquired.” It’s an honest and fun take on an industry that often overpromises its IPO prospects. She points to the sale of TaskRabbit to IKEA as evidence that the right acquisition can create lasting value.

As for 2026, Brown-Philpott’s priority is simple: “We are actively deploying capital.” It looks for Series A and Series B companies that have achieved product-market fit at scale, allowing founders to define what that means. As the broader venture ecosystem debates the future of diversity initiatives, it is focused on finding great founders, wherever they are.

“I’m from Detroit,” she says. “Difficult things are hard, but we know how to do hard things.”