Former TaskRabbit CEO Launches Cherryrock Capital to Fund Underrepresented Tech Entrepreneurs

While much of the venture capital industry has been pursuing mega-rounds and high-profile AI deals, Stacy Brown-Philpot is taking a contrarian approach with Cherryrock Capital. The firm focuses on writing smaller Series A and B checks to founders frequently overlooked by larger investment firms.

The former TaskRabbit CEO and Google veteran launched Cherryrock Capital approximately one year ago after identifying a persistent market gap: access to capital for underinvested entrepreneurs building software companies during critical growth stages.

From Silicon Valley Vision to Reality

Brown-Philpot arrived in the Bay Area 25 years ago with aspirations of becoming a venture capitalist, even dedicating her Stanford Business School application essay to the topic. After spending a decade at Google and successfully leading TaskRabbit through its acquisition by IKEA, she has returned to her original career objective.

Prior to establishing Cherryrock, Brown-Philpot served on the investment committee for the SoftBank Opportunity Fund, a $100 million vehicle launched in 2020 to support underserved entrepreneurs. This experience validated the abundance of overlooked founder talent in the market. When SoftBank divested from the diversity-focused initiative in late 2023, Brown-Philpot doubled down on her conviction and launched her own fund.

Strategic Investment Approach

By February 2025, Cherryrock had closed its debut fund with a pipeline exceeding 2,000 companies. The fund targets 12 to 15 investments—a concentrated portfolio strategy that contrasts sharply with seed funds making dozens of bets or mega-funds writing nine-figure checks.

Brown-Philpot's deployment strategy is deliberately measured. One year post-announcement, she and her team, including cofounder Saydeah Howard (formerly nine years at IVP), have completed five investments, representing approximately one-third of their target allocation. This disciplined pace represents a return to traditional venture capital methodologies in an era of rapid capital deployment.

LP Base and Market Position

Cherryrock's limited partner roster includes prominent financial institutions:

"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," Brown-Philpot stated.

Regulatory Landscape and Compliance

California's new diversity reporting law requires VC firms with California nexus to report demographic data on portfolio companies' founding teams, with initial compliance deadlines in April. The legislation emphasizes transparency over mandates, requiring reporting without imposing quotas.

For Cherryrock, which already tracks and prioritizes investments in diverse founders, compliance represents standard operating procedure. "You accomplish what you measure," Brown-Philpot noted.

Portfolio Companies

Brown-Philpot's investment thesis is reflected in her portfolio selections:

1. Coactive AI
Founded by Cody Coleman (MIT graduate with advanced degrees in philosophy and engineering from MIT and Stanford), Coactive provides multimodal AI infrastructure to the media and entertainment vertical. Cherryrock led the Series B round alongside Emerson Collective.

2. Vitable Health
Founded by Joseph Kitonga (Thiel Fellow and Y Combinator alumnus), the Philadelphia-based company delivers on-demand, primary care-based health insurance solutions to employers and hourly workers. "He is the exact kind of founder that we want to back," Brown-Philpot said. "He does what he says he's going to do."

Strategic Perspective and Exit Philosophy

Beyond Cherryrock, Brown-Philpot serves on the boards of HP, StockX, and Stanford University—positions providing insight into both enterprise procurement patterns and emerging founder talent.

Regarding exit strategies, Brown-Philpot maintains a pragmatic stance: "It's very difficult to go public. Most companies don't go public, they do get acquired." She references TaskRabbit's acquisition by IKEA as evidence that strategic acquisitions can generate substantial value creation.

2026 Priorities

Brown-Philpot's focus for 2026 is straightforward: "We are actively deploying capital." The firm seeks Series A and B companies that have demonstrated product-market fit at scale, allowing founders to define their own success metrics.

"I'm from Detroit," she concludes. "Hard things are hard, but we know how to do hard things."