As much of venture capital crowds into mega-rounds and headline AI bets, Stacy Brown-Philpot is steering Cherryrock Capital in a different direction — toward underinvested founders at the crucial Series A and B stages, with a patient tempo and a concentrated portfolio that recalls an earlier era of venture discipline.
A Market Reset Opens A Persistent Funding Gap
The funding environment has cooled from its 2021 peak, and the pendulum has swung back to rigorous diligence and fewer, larger winners. PitchBook-NVCA data shows U.S. deal value declined sharply in 2023 before stabilizing, while late-stage activity grew more selective. In that shakeout, founders without traditional networks or pattern-matching pedigrees feel the pinch first.
The numbers underscore the gap. Crunchbase has reported that Black founders received roughly 1% of U.S. venture dollars in 2023, and funding to Latino founders remains near the low single digits. PitchBook found all-women founding teams drew about 2% of global venture funding last year. Those figures have barely budged since 2020’s pledges, even as AI froth lifted certain categories.
Inside Cherryrock’s Focused Playbook For Growth
Brown-Philpot launched Cherryrock after identifying a consistent bottleneck: promising software startups, led by founders outside the usual mold, struggling to raise growth capital despite traction. The strategy is deliberately tight. The debut fund targets 12 to 15 investments, avoiding spray-and-pray in favor of concentrated ownership and hands-on support.
One year in, Cherryrock has backed five companies — a measured cadence that contrasts with the race-to-deploy norm. The firm’s pipeline surpassed 2,000 companies before its first close, a signal that deal flow is not the constraint. Co-founder Saydeah Howard, who spent nine years at IVP, brings late-stage rigor to A/B checks sized to fuel repeatable go-to-market motion rather than vanity burn.
Cherryrock defines target stage as “product-market fit at scale,” but lets founders evidence that with their own operating metrics: efficient net new ARR, retention quality, or unit economics tuned to sustainable growth. In a climate where distribution and sales velocity can matter as much as model breakthroughs, the firm emphasizes revenue engines over raw hype.
Portfolio Signals From AI To Accessible Care
The early portfolio reflects that thesis. Cherryrock led a round in Coactive AI, founded by Cody Coleman, which builds multimodal infrastructure for media and entertainment teams facing an explosion of unstructured data and brand-safety risk. The bet is that tooling for responsible AI at enterprise scale will be a durable picks-and-shovels business.
Another investment, Vitable Health, founded by Joseph Kitonga, offers primary care–centered coverage to employers and hourly workers — a segment often priced out of traditional plans. Brown-Philpot’s years leading TaskRabbit provided a front-row view into the needs of flexible and frontline workers, informing Cherryrock’s conviction on care models built for real-world utilization, not just enrollment.
Returns First With A Broader Investment Aperture
Brown-Philpot’s approach is intentionally framed around performance, not politics. Her LP base includes JPMorgan, Bank of America, Goldman Sachs Asset Management, MassMutual, Top Tier Capital Partners, and Pivotal Ventures — institutions that prioritize returns and governance. The message: sourcing from overlooked talent isn’t a concession; it’s an advantage in a crowded market.
A new California transparency law requires venture firms with a state nexus to report founders’ demographic data, with initial reporting deadlines approaching. Unlike quota-based regimes, this rule focuses on disclosure. For firms already measuring who they back, compliance is straightforward — and the resulting visibility may reward managers whose pipelines reflect the broader market of entrepreneurs.
Experience Across Operating Rooms And Boardrooms
Cherryrock’s edge is stitched from Brown-Philpot’s operating and governance history. The former TaskRabbit CEO and long-time Google executive also serves on the boards of HP, StockX, and Stanford University, offering line-of-sight into enterprise demand patterns, consumer behavior, and the next generation of technical founders. That multi-lens vantage point shows up in diligence on buyer intent, not just product demos.
Her investing arc includes the SoftBank Opportunity Fund, a $100 million vehicle launched to back underserved entrepreneurs and later sold to its leadership team. That work underscored a simple conclusion: the bottleneck isn’t talent or ideas; it’s access at the moments when capital is most catalytic.
Exit Realism And 2026 Priorities For Cherryrock
Cherryrock is pragmatic about outcomes. With IPO windows narrow and public markets rewarding profitability over growth at any cost, M&A remains the most common path to liquidity. Brown-Philpot has lived that arc — TaskRabbit’s sale to IKEA created an enduring strategic fit — and she evaluates portfolios with similar realism on acquirer logic and integration risk.
The 2026 plan is straightforward: continue deploying into A/B-stage software companies demonstrating repeatability, capital efficiency, and clear customer love. In a venture cycle resetting around discipline, Cherryrock is betting that the best risk-adjusted returns will come from founders others missed — not because they were unqualified, but because the industry wasn’t looking closely enough.
