Venture Capital’s Quiet Revolution: How Stacy Brown-Philpot Is Rewriting the Rules of Startup Funding

In an era where Silicon Valley’s venture capital scene resembles a high-stakes poker game with billion-dollar chips flying across the table, Stacy Brown-Philpot is playing an entirely different game. The former TaskRabbit CEO and Google veteran isn’t chasing the next AI unicorn or competing for the flashiest mega-rounds. Instead, she’s quietly building Cherryrock Capital into what might be the most refreshing throwback in modern venture capital.

The Gap That Changed Everything

When Brown-Philpot stepped away from her role as TaskRabbit’s CEO after its successful acquisition by IKEA, she didn’t immediately dive into her next venture. Instead, she took time to reflect on what she’d observed throughout her career—a persistent, troubling gap in the venture capital ecosystem that had nothing to do with market cycles or technological trends.

“The access to capital for underinvested entrepreneurs was glaring,” Brown-Philpot explained to TechCrunch. This wasn’t just another Silicon Valley observation; it was personal. She had arrived in the Bay Area 25 years earlier with dreams of becoming a venture capitalist, even writing about it in her Stanford Business School application. After a decade at Google and successfully navigating TaskRabbit through its acquisition, she found herself back where she started—but with a much clearer mission.

From SoftBank to Cherryrock: A Calculated Pivot

Before launching Cherryrock, Brown-Philpot served on the investment committee for the SoftBank Opportunity Fund, a $100 million initiative launched in 2020 specifically to support underserved entrepreneurs. The experience was eye-opening. “There was no shortage of overlooked founders,” she noted. “The pipeline was there; the capital wasn’t.”

When SoftBank sold the Opportunity Fund to its leadership team in late 2023, divesting from what had become a politically charged initiative, Brown-Philpot saw her opportunity. She launched Cherryrock Capital with a clear thesis: write smaller Series A and B checks to companies that larger firms routinely overlook, particularly those led by founders who don’t fit the traditional Silicon Valley mold.

By the time Cherryrock closed its debut fund in February 2025, Brown-Philpot and her team had already reviewed more than 2,000 companies. The pipeline was real, the opportunity was clear, and the timing felt right.

The Anti-Fund: Concentrated, Patient, Purposeful

Cherryrock’s approach stands in stark contrast to the venture capital arms race. While many funds rush to deploy capital at breakneck speed—sometimes writing checks within weeks of meeting founders—Brown-Philpot is taking a more measured approach. A year after announcing the fund, Cherryrock has backed just five companies, putting them about a third of the way toward their target of 12 to 15 investments from the first fund.

This concentrated strategy is deliberate. “We’re looking for Series A and B companies that have achieved product-market fit at scale,” Brown-Philpot explained. “But we let the founders define what that means for their business.” It’s a refreshing departure from the rigid metrics and growth expectations that often dominate venture conversations.

The fund’s size and check strategy also buck current trends. While mega-funds write nine-figure checks and seed funds make dozens of bets hoping for one massive winner, Cherryrock is targeting the middle ground—the crucial growth stage where companies have proven their concept but need capital to scale.

Navigating the Political Minefield

In today’s political climate, where diversity, equity, and inclusion initiatives have become lightning rods for controversy, Brown-Philpot’s approach is both strategic and principled. She deliberately uses the term “underinvested” rather than more politically charged language, but the mission remains clear.

When pressed about the current environment, where DEI has become a contentious issue, Brown-Philpot remains unfazed. “It doesn’t change the pitch at all,” she said. “When we look at the people who decided to back Cherryrock—JPMorgan, Bank of America, Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates’s Pivotal Ventures—these are financial institutions who expect to generate a return. Our job as investors is to do just that.”

Interestingly, Brown-Philpot may find herself in an unexpectedly advantageous position. 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. Unlike some corporate diversity initiatives that have faced legal challenges, this law focuses on transparency rather than mandates, requiring reporting but not quotas.

For a firm like Cherryrock that’s already tracking and prioritizing investments in diverse founders, compliance is “table stakes,” as Brown-Philpot puts it. “You accomplish what you measure.”

The Portfolio: Real Companies, Real Problems

Cherryrock’s investments reflect Brown-Philpot’s thesis about underinvested entrepreneurs solving real problems. One standout 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 to the media and entertainment industry—a sector now under intense scrutiny following controversies around AI-generated content.

Brown-Philpot led Coactive’s Series B alongside Emerson Collective, betting on a founder who brings both technical expertise and philosophical perspective to one of tech’s most contentious areas.

Another key investment is Vitable Health, founded by Joseph Kitonga, a Thiel Fellow and Y Combinator alum. The Philadelphia-based company provides on-demand, primary care-based health insurance to employers and hourly workers—the kind of population Brown-Philpot came to know well as TaskRabbit’s CEO.

“Joseph 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 through her work with the SoftBank Opportunity Fund at the seed stage, then doubled down when Cherryrock launched.

The Detroit Mentality: Hard Things Are Hard

Brown-Philpot’s perspective is shaped by her roots. “I’m from Detroit,” she says. “Hard things are hard, but we know how to do hard things.” This mentality permeates Cherryrock’s approach—it’s not about chasing easy wins or following the crowd, but about doing the hard work of finding great companies that others overlook.

Her board positions at HP, StockX, and Stanford University give her unique insights into both enterprise buyers and the next generation of founders. At Stanford, she’s watching students navigate questions about 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,” she observed.

The Exit Reality Check

In an industry that often overpromises on IPO prospects and unicorn valuations, Brown-Philpot brings a refreshingly honest perspective on exits. “It’s very difficult to go public,” she said. “Most companies don’t go public, they do get acquired.” She points to TaskRabbit’s sale to IKEA as proof that the right acquisition can create lasting value—not just for founders and investors, but for the employees and customers who depend on the company’s continued success.

The Future: Active Deployment, Patient Capital

As 2026 approaches, Brown-Philpot’s priority is simple: “We are actively deploying capital.” She’s looking for companies that have moved beyond the initial product-market fit phase and are ready to scale. And while the broader venture ecosystem debates the future of diversity initiatives, she remains focused on finding great founders, wherever they are.

The Cherryrock model represents something rare in modern venture capital: a return to fundamentals. It’s about patient capital, concentrated bets, and a genuine belief that great companies can come from anywhere. In a world where venture capital often feels like a game of who you know and how much money you can raise, Brown-Philpot is betting on something different—that the best investments might be the ones everyone else is missing.

And if her track record is any indication, she might just be right.

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