In a modified VC scenario, this factor doubles for overlooked founders

Much of Silicon Valley has spent years chasing mega-rounds and crazy AI deals. Meanwhile, Stacy Brown-Philpot is using Cherryrock Capital as a throwback to the early days of venture capital, writing small series A and B checks to founders of big firms that she often ignored.

The former TaskRabbit CEO and ten-year Google veteran launched Cherryrock last year after seeing what he calls a persistent gap: access to capital for “low-investment entrepreneurs” building software companies at a critical growth stage.

“When I left TaskRabbit, I took a moment to figure out what’s next and I saw this gap in the market, which is access to capital, especially for entrepreneurs who haven’t invested,” Brown-Philpot told TechCrunch. He had come to the Bay Area 25 years ago, planning to become a VC and write his Stanford Business School essay about it. After spending a decade at Google and leading TaskRabbit to a successful exit from IKEA, he’s finally back to that original plan.

He circled back to it for a reason. Before 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 unemployed entrepreneurs. That experience proved that there is no shortage of overlooked innovators.

SoftBank itself sold the Opportunity Fund to its leadership team in late 2023, exiting the diversification-focused program. Brown-Philpot, on the other hand, doubled down, and presented his own bag. By the time he closed Cherryrock’s first fund in February 2025, he had more than 2,000 2000 companies.

Cherryrock is looking at 12 to 15 investments in its first fund — a more focused and different approach from seed money that makes a bunch of bets, or big funds that write nine checks. Brown-Philpot also takes his time; a year after announcing the fund, he and his 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. In an era where many funds rush to invest almost as quickly as they are raised, Brown-Philpot’s limited pace is another throwback to an earlier generation of VCs.

Brown-Philpot’s focus on “thinly invested” founders — a careful choice of words in today’s political climate — means supporting entrepreneurs who may not fit the typical Silicon Valley mold.

When asked directly about the current political environment, where the DEI has become a lightning rod, Brown-Philpot is unfazed. “It doesn’t change the tone at all,” he said. “If we look at the people who have decided to support Cherryrock, like JPMorgan and Bank of America … these are financial institutions that expect to generate profits. Our job as investors is to do just that.”

In addition to those investors, Cherryrock’s LP list includes Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates’ Pivotal Ventures. Some of these have backed away from clear promises of diversity amid pressure from the Trump administration. Yet Brown-Philpot may find himself in an unexpectedly lucrative position.

A new diversity reporting law in California requires VC firms with a California nexus to report statistical data on the founding teams of their portfolio companies, with an initial deadline in April. Unlike other corporate diversity programs that have faced legal challenges, the law focuses on notifications rather than mandates, requiring reporting but not quotas. For a company like Cherryrock that already tracks and prioritizes investments for various startups, compliance is “table stakes,” as Brown-Philpot puts it. “You achieve what you measure.”

Brown-Philpot’s view is based on his point of view across multiple institutions. Beyond Cherryrock, he sits on the boards of HP, StockX, and Stanford University – roles that give him insight into both business buyers and the next generation of founders. At Stanford, he watched students navigate questions about the impact of AI on the workplace. “What I see on campus is that students plan their way and find a way to create opportunities for themselves,” he said.

His portfolio reflects his 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 for the media and entertainment industry, a sector now under intense scrutiny following controversy over AI-generated content. Cherryrock led Coactive’s Series B alongside Emerson Collective.

Another bet is Vital Health, founded by Joseph Kitonga, a Thiel Fellow and Y Combinator alum. The Philadelphia-based company offers in-demand, primary care-based health insurance to employers and hourly workers — the kind of people Brown-Philpot got to know well as CEO of TaskRabbit during its last years as a private company. Kitonga is “exactly the type of innovator we want to support,” Brown-Philpot said. “He did what he said he was going to do.” Brown-Philpot first invested in the seed stage of Vital through his work with the SoftBank Opportunity Fund.

When asked about her work philosophy, Brown-Philpot is smart about going out. “It’s very difficult to go public,” he said. “Many companies don’t succeed in society, they are acquired.” It’s a refreshingly honest 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’re spreading the big bucks.” You want series A and B companies that have achieved product market equity at scale, allowing founders to define what that means. And while the broader ecosystem is debating the future of diversity initiatives, it’s focused on finding great innovators, wherever they are.

“I’m from Detroit,” he says. “Hard things are hard, but we can do hard things.”