In the changing VC landscape, this activist is increasingly taking on the overlooked startups

Much of Silicon Valley has spent years chasing mega-rounds and buzzy AI. Meanwhile, Stacy Brown-Philpot runs Cherryrock Capital as a backer in the early days of the business, writing small Series A and B checks to startups that big companies ignore.

The former TaskRabbit CEO and Google veteran founded Cherryrock a year ago after seeing what he calls an unstoppable gap: funding for “underfunded businesses” building software companies for critical growth.

“After I left TaskRabbit, I took some time to figure out what was next and saw a gap in the market, which was an opportunity to make money, especially for entrepreneurs who don’t have a lot of money,” Brown-Philpot told TechCrunch. He came to the Bay Area 25 years ago, plans to become a VC and is also writing his thesis at Stanford Business School. After spending a decade at Google and leading TaskRabbit to a successful spin-off from IKEA, he’s back to that original plan.

He came back to it because. Before founding Cherryrock, Mr. Brown-Philpot was a member of the investment committee of the SoftBank Opportunity Fund, a $100 million vehicle launched in 2020 to support underserved businesses. That event proved that there was no shortage of overlooked innovators.

SoftBank itself sold the Opportunity Fund to its management team at the end of 2023, leaving the diversified focus. Brown-Philpot, meanwhile, doubled up, and started his bag. By the time Cherryrock closed its fund in February 2025, it already had more than 2,000 companies in its pipeline.

Cherryrock is looking at 12 to 15 ventures from its first fund — a more sustainable and different approach than seed funds that bet more, or larger 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 the IVP firm, have backed just five companies, putting them about a third of the way through. In an era where most funds rush to send money as fast as they raise it, Brown-Philpot’s speed is a throwback to an earlier generation of VCs.

Brown-Philpot’s focus on “underfunded” startups — a good choice of phrase in today’s political climate — means supporting entrepreneurs who don’t fit the mold of Silicon Valley.

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

In addition to 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 backtracked on diversity pledges amid pressure from the Trump administration. Yet Brown-Philpot may find himself in an unexpectedly lucrative position.

New different reporting rules California requires VC companies with California ties to disclose information about their startups, with a deadline of April. Unlike other business models that have faced legal challenges, the law it focuses on transparency rather than mandate, which requires reporting but not duplication. For a company like Cherryrock that is already tracking and prioritizing business for various startups, tracking is “tables,” as Brown-Philpot says. “You get what you measure.”

Brown-Philpot’s theory is confirmed by his observations in several organizations. Beyond Cherryrock, he sits on the boards of HP, StockX, and Stanford University—positions that give him exposure to both business buyers and the next generation of startups. At Stanford, he sees students exploring questions about the impact of AI on work. “What I’m seeing on campus is showing students making a plan and finding a way to create opportunities for themselves,” he said.

His history reflects his views. 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 that is now under intense scrutiny following the controversy surrounding AI-generated content. Cherryrock led Coactive’s Series B alongside Emerson Collective.

other bets are Good Healthfounded by Joseph Kitonga, a Thiel Fellow and Y Combinator alum. The Philadelphia-based company offers on-demand, managed primary care health insurance for employers and hourly workers — the kind of people Brown-Philpot got to know well as CEO of TaskRabbit during its last years as a freelance company. Kitonga “is exactly the type of innovator we want to follow,” Brown-Philpot said. “He does what he says he’s going to do.” Brown-Philpot first invested in Vitable shares through his work with the SoftBank Opportunity Fund.

When asked about his technology to use, Mr Brown-Philpot does not like output. “It’s very difficult to go public,” he said. “A lot of companies don’t go public, they get paid.” It’s a refreshingly honest take on a company that often predicts an IPO. He points to the sale of TaskRabbit to IKEA as evidence that the right acquisition can create lasting value.

As for 2026, Brown-Philpot’s priority is simple: “We’re sending money faster.” They are looking for Series A and B companies that have achieved market capitalization on a large scale, allowing the founders to define the meaning. And while the larger universe debates the future of various initiatives, they focus on finding the right startups, wherever they are.

“I’m from Detroit,” he said. “Hard things are hard, but we know how to do hard things.”