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 “underinvested 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, which was access to capital, particularly for underinvested entrepreneurs,” Brown-Philpot told TechCrunch. She’d originally come to the Bay Area 25 years ago, planning to become a VC and even writing her Stanford Business School essay about it. After spending a decade at Google and leading TaskRabbit to a successful exit to IKEA, she’s finally back to that original plan.
She circled back to it for a reason. Before launching Cherryrock, Brown-Philpot was a member of the investment committee for the SoftBank Opportunity Fund, a $100 million vehicle started in 2020 to back underserved entrepreneurs. That experience proved there was no shortage of overlooked founders.
SoftBank itself sold the Opportunity Fund to its leadership team in late 2023, divesting from the diversity-focused initiative. Brown-Philpot, meanwhile, doubled down, and launched her own fund. By the time she closed Cherryrock’s debut fund in February 2025, she already had more than 2,000 companies in her pipeline.
Cherryrock is targeting 12 to 15 investments from its first fund — a concentrated approach and stark contrast to …