Investing in the Underdogs: How This Executive is Embracing Overlooked Founders in the Evolving VC Industry

Investing in Overlooked Entrepreneurs: The Story of Stacy Brown-Philpot and Cherryrock Capital

In the fast-paced world of Silicon Valley, where mega-rounds and AI deals dominate the headlines, Stacy Brown-Philpot is taking a different approach. As the former TaskRabbit CEO and Google veteran, she founded Cherryrock Capital with a mission to support underinvested entrepreneurs at the critical growth stage.

After identifying a gap in the market for capital access, particularly for founders who are often overlooked by larger firms, Brown-Philpot set out to make a difference. Drawing on her experience as a member of the investment committee for the SoftBank Opportunity Fund, she saw firsthand the abundance of talented but underrepresented founders.

While SoftBank divested from the Opportunity Fund in 2023, Brown-Philpot saw an opportunity to double down and launch her own fund. By early 2025, Cherryrock had closed its debut fund with a strong pipeline of over 2,000 companies. The fund’s focus is on making 12 to 15 strategic investments, a deliberate strategy that sets it apart from seed funds or large-scale investors.

With a measured approach to investing, Cherryrock has backed five companies so far, led by Brown-Philpot and her team, including seasoned investor Saydeah Howard. The fund’s emphasis on underinvested founders has resonated in today’s diverse landscape, where inclusivity is a key priority.

When addressing the current political climate and the focus on diversity, Brown-Philpot remains steadfast in her commitment to supporting founders who bring unique perspectives to the table. With backing from institutions like JPMorgan, Bank of America, and Goldman Sachs Asset Management, Cherryrock is well-positioned to deliver returns while championing diversity in the startup ecosystem.

As California introduces new diversity reporting laws for VC firms, Cherryrock’s proactive approach to tracking and prioritizing investments in diverse founders aligns with the industry’s evolving standards. For Brown-Philpot, transparency and accountability are essential in driving meaningful change.

With a broad perspective gained from her roles on various boards, including HP and Stanford University, Brown-Philpot is attuned to the evolving landscape of entrepreneurship. Her investments in companies like Coactive AI and Vitable Health reflect her commitment to supporting innovative solutions in industries like media, entertainment, and healthcare.

Looking ahead to the future, Brown-Philpot’s focus remains on deploying capital effectively, targeting Series A and B companies with proven product-market fit. While the venture capital world debates the future of diversity initiatives, she remains dedicated to finding and supporting exceptional founders, regardless of their background or location.

For Brown-Philpot, the road ahead may be challenging, but her Detroit roots have taught her that perseverance pays off. As she continues to navigate the dynamic world of venture capital, her unwavering belief in backing underrepresented entrepreneurs sets Cherryrock Capital apart as a beacon of inclusivity and innovation.