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In the fast-paced landscape of venture capital, innovating funding strategies is vital for entrepreneurs seeking sustainable growth. Stacy Brown-Philpot’s approach at Cherryrock Capital exemplifies a return to foundational investment principles, emphasizing support for underrepresented founders navigating the growth phase of their businesses.
Drawing on her impressive background as the former CEO of TaskRabbit and a veteran of Google, Brown-Philpot launched Cherryrock Capital after identifying a significant disparity in funding availability for “underinvested entrepreneurs” developing software solutions at pivotal stages of development.
When I departed from TaskRabbit, I took time to reassess my next steps and recognized a critical gap in capital access for underinvested entrepreneurs,” Brown-Philpot explained. Having originally set her sights on venture capital while drafting her Stanford Business School application, she is finally realizing that vision after leading TaskRabbit to a successful acquisition by IKEA.
Prior to launching Cherryrock, she served on the investment committee of the SoftBank Opportunity Fund, a $100 million initiative established to support underserved entrepreneurs, which underscored the abundance of overlooked talent in the startup world.
Following the divestiture of the Opportunity Fund from SoftBank in late 2023, which dampened their focus on diversity, Brown-Philpot committed to her mission with her own fund. By the closure of Cherryrock’s inaugural fund in February 2025, she had already sifted through a pipeline of over 2,000 companies, indicative of her thorough approach to investment.
Cherryrock’s strategy involves making 12 to 15 targeted investments, a stark contrast to the sprawling seed funds making numerous smaller bets or massive funds deploying nine-figure capital. With a deliberate pace, Brown-Philpot and her co-founder Saydeah Howard, a veteran from IVP, have made five investments to date, showcasing a cautious methodology reminiscent of earlier venture capital eras.
By prioritizing funding for “underinvested” founders, a strategic choice in today’s socio-political climate, Brown-Philpot seeks to uplift entrepreneurs who may not conform to the traditional Silicon Valley archetype.
Addressing the complexities surrounding DEI in current discourse, Brown-Philpot remains unshaken: “The political atmosphere doesn’t change our focus. Our financial backers, like JPMorgan and Bank of America, expect a return on their investment, and that’s our mandate,” she asserted.
Cherryrock’s partners include esteemed investors such as Goldman Sachs Asset Management, MassMutual, and Melinda Gates’s Pivotal Ventures. Even amidst shifting diversity pledges, Brown-Philpot may leverage the situation to her advantage.
With a new California diversity reporting requirement for VC firms, Cherryrock is in a strong position due to its built-in commitment to tracking and investing in diverse founders. As Brown-Philpot succinctly puts it, “You measure what you want to accomplish.”
Her insights, shaped by her multifaceted experiences, extend beyond Cherryrock. As a board member for HP, StockX, and Stanford University, she possesses a keen understanding of both enterprise demands and emerging entrepreneurial talent. Observing students at Stanford exploring the impact of technological advancements on employment, she notes, “These students are proactively carving out opportunities for themselves.
Cherryrock’s portfolio reflects her investment thesis, featuring Coactive AI, spearheaded by Cody Coleman, an MIT alum. The firm provides essential multimodal infrastructure for the media sector, currently facing scrutiny due to controversies surrounding technology-generated content. Cherryrock led Coactive’s Series B round with Emerson Collective.
Additionally, Vitable Health, co-founded by Thiel Fellow Joseph Kitonga, has gained attention for offering on-demand, primary care-based insurance to employers and hourly workers—a demographic Brown-Philpot is intimately familiar with from her tenure at TaskRabbit. Kitonga embodies the type of founder we aspire to support,” she remarked, recalling her early investment in him through the SoftBank Opportunity Fund.
When discussing her operational strategy, Brown-Philpot pragmatically acknowledges the challenges of going public. Most companies are acquired rather than going through IPOs,” she states, delivering an honest perspective in an industry prone to overpromising on public offering potentials. She uses TaskRabbit’s sale to IKEA as a case study for how strategic acquisitions can yield significant value.
Looking ahead to 2026, her mission remains clear: “Our focus is on actively deploying capital.” She searches for Series A and B firms that have achieved scalable product-market fit, allowing founders to define that success. As the larger venture ecosystem grapples with the essence of diversity initiatives, she is committed to identifying exceptional founders, regardless of their backgrounds.
“I’m from Detroit,” she states proudly. “We know how to tackle challenging situations head-on.”
### Hustle Verdict
Our take is that Cherryrock Capital’s unique strategy signifies a crucial pivot in venture funding. By addressing the capital accessibility gap for diverse founders, Stacy Brown-Philpot not only fosters innovation but also positions her firm to harness a broader spectrum of talent. The bottom line is that entrepreneurs should pay close attention to this trend, as it heralds a shift in the landscape with profitable opportunities for businesses that align with these inclusive investment philosophies.
