A Shift in Venture Capital Focus
While much of Silicon Valley has focused on massive funding rounds and buzzy AI deals, Stacy Brown-Philpot, a former CEO of TaskRabbit and a decade-long veteran at Google, is taking a different approach with her venture capital firm, Cherryrock Capital. She is concentrating on smaller Series A and B investments, specifically targeting founders whom larger firms often overlook. This strategy harks back to an earlier era of venture capital, emphasizing foundational growth and underinvested entrepreneurs.
Identifying a Market Gap
Brown-Philpot launched Cherryrock Capital a year ago after observing a persistent gap in the market: access to crucial growth-stage capital for what she describes as "underinvested entrepreneurs" building software companies. Her journey to venture capital was a long-held ambition, dating back to her Stanford Business School days. After leading TaskRabbit to a successful acquisition by IKEA, she circled back to her original aspiration.
Leveraging Past Experience
Prior to founding Cherryrock, Brown-Philpot gained valuable experience as part of the investment committee for the SoftBank Opportunity Fund. This $100 million initiative, launched in 2020 to support underserved entrepreneurs, confirmed her belief in the abundance of overlooked talent. While SoftBank later divested from the fund, Brown-Philpot doubled down on her vision, launching her own firm. By the time she closed Cherryrock's debut fund in February 2025, she had an extensive pipeline of over 2,000 companies.
A Concentrated and Deliberate Approach
Cherryrock Capital aims to make 12 to 15 investments from its first fund, a stark contrast to seed funds that make numerous bets or larger funds that deploy enormous checks. Brown-Philpot and her team, including co-founder Saydeah Howard, who has extensive experience at IVP, are taking a measured approach. A year after announcing the fund, they have backed only five companies, moving deliberately towards their investment goals. This patient deployment of capital is another characteristic reminiscent of earlier venture capital practices.
Focus on "Underinvested" Founders
Brown-Philpot's deliberate choice of the term "underinvested" founders highlights her commitment to backing entrepreneurs who may not fit the conventional Silicon Valley mold. She remains unfazed by the current political climate surrounding diversity, equity, and inclusion (DEI). "It doesn't change the pitch at all," she stated. "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."
Strong Investor Backing
Cherryrock's Limited Partner (LP) roster includes prominent institutions such as JPMorgan, Bank of America, Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Melinda Gates's Pivotal Ventures. Despite some institutions stepping back from explicit diversity pledges due to political pressures, Brown-Philpot's firm is positioned advantageously. California's new diversity reporting law, requiring VC firms with a California nexus to report demographic data on founding teams, aligns perfectly with Cherryrock's existing practices. Brown-Philpot notes that for Cherryrock, compliance is "table stakes" because "you accomplish what you measure."
Informed Perspective and Diverse Investments
Brown-Philpot's broad perspective, gained from her roles on the boards of HP, StockX, and Stanford University, provides insight into both enterprise needs and emerging founders. She observes students at Stanford grappling with AI's impact on employment, noting their drive to create opportunities. Her portfolio reflects this forward-thinking approach. For instance, Cherryrock co-led the Series B investment in Coactive AI, a company providing AI infrastructure for the media and entertainment sector, led by MIT graduate Cody Coleman. Another notable investment is Vitable Health, founded by Thiel Fellow and Y Combinator alum Joseph Kitonga. This Philadelphia-based company offers on-demand primary care-based health insurance to employers and hourly workers, a demographic familiar to Brown-Philpot from her TaskRabbit tenure. She previously invested in Vitable Health at the seed stage through her work with the SoftBank Opportunity Fund.
Pragmatic Approach to Exits
When discussing exit strategies, Brown-Philpot offers a pragmatic view. "It's very difficult to go public," she acknowledged. "Most companies don't go public; they do get acquired." She points to TaskRabbit's acquisition by IKEA as an example of how a well-suited acquisition can create enduring value, a realistic perspective in an industry often focused on IPO potential.
Looking Ahead to 2026
For 2026, Brown-Philpot's primary focus is straightforward: "We are actively deploying capital." She is seeking Series A and B companies that have demonstrated product-market fit at scale, allowing founders to define their own metrics for success. While the broader venture capital landscape navigates the complexities of diversity initiatives, Brown-Philpot remains dedicated to identifying exceptional founders, regardless of their background or location. "I'm from Detroit," she states. "Hard things are hard, but we know how to do hard things."
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