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

Source: TechCrunch

Overview

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 “under‑invested 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, particularly for under‑invested entrepreneurs,” Brown‑Philpot told TechCrunch.

She originally came to the Bay Area 25 years ago, planning to become a VC and even writing her Stanford Business School essay about it. After a decade at Google and leading TaskRabbit to a successful exit to IKEA, she’s finally back to that original plan.

From SoftBank Opportunity Fund to Cherryrock

Before launching Cherryrock, Brown‑Philpot was a member of the investment committee for the SoftBank Opportunity Fund, a $100 M vehicle started in 2020 to back underserved entrepreneurs. That experience proved there was no shortage of overlooked founders.

• Late 2023: SoftBank sold the Opportunity Fund to its leadership team, divesting from the diversity‑focused initiative.
• Early 2025: Brown‑Philpot closed Cherryrock’s debut fund, already having 2,000+ companies in her pipeline.

Investment Strategy

• Target: 12–15 investments from the first fund – a concentrated approach, starkly contrasting seed funds that make dozens of bets or massive funds that write nine‑figure checks.
• Pace: A year after announcing the fund, Brown‑Philpot and co‑founder Saydeah Howard (nine years at IVP) have backed five companies, roughly a third of the way to the goal.

“In an era when many funds race to deploy capital almost as quickly as it’s raised, our measured pace is another throwback to an earlier generation of VCs.”

Focus on “Under‑Invested” Founders

Brown‑Philpot’s careful wording—under‑invested rather than diverse—reflects today’s political climate. She backs entrepreneurs who might not fit the typical Silicon Valley mold.

TechCrunch Event

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. 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.”

Limited Partners

• JPMorgan
• Bank of America
• Goldman Sachs Asset Management
• MassMutual
• Top Tier Capital Partners
• Melinda Gates’s Pivotal Ventures

Some of these firms have stepped back from explicit diversity pledges amid pressure from the Trump administration. Yet Brown‑Philpot may find herself in an unexpectedly advantageous position.

California Diversity‑Reporting Law

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 2026.

• The law focuses on transparency, not quotas.
• For Cherryrock, which already tracks and prioritizes investments in diverse founders, compliance is “table stakes.”

“You accomplish what you measure,” Brown‑Philpot says.

Board Seats & Thought Leadership

Beyond Cherryrock, Brown‑Philpot sits on the boards of:

• HP
• StockX
• Stanford University

These roles give her insight into both enterprise buyers and the next generation of founders. At Stanford, she watches students grapple with 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.”

Portfolio Highlights

“He does what he says he’s going to do,” Brown‑Philpot said of Kitonga. “He is the exact kind of founder that we want to back.”

Operating Philosophy

When asked about exits, Brown‑Philpot is pragmatic:

“It’s very difficult to go public. Most companies don’t go public; they get acquired.”

This refreshingly honest take stands out in an industry that often overpromises on IPO prospects. She points to TaskRabbit’s sale to IKEA as a model of a successful exit.

Outlook for 2026

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. While the broader venture ecosystem debates the future of diversity initiatives, she remains 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.”