In a changed VC landscape, this exec is doubling down on overlooked founders

In a landscape where Silicon Valley often chases high-stakes investments and trendy AI projects, Stacy Brown-Philpot is steering Cherryrock Capital in a different direction. With a focus on smaller Series A and B investments, she aims to support founders who typically go unnoticed by larger venture firms. Brown-Philpot, a former CEO of TaskRabbit and seasoned executive at Google, founded Cherryrock a year ago after recognizing a persistent gap in access to capital for underrepresented entrepreneurs. "After leaving TaskRabbit, I took time to reflect and noticed this market gap regarding funding for underinvested entrepreneurs," she shared in a recent interview. Her journey into venture capital began 25 years ago when she envisioned a career in the field, even writing about it in her Stanford Business School application. After years at Google and leading TaskRabbit to a successful acquisition by IKEA, she returned to her original ambition of supporting startups. Before establishing Cherryrock, Brown-Philpot served on the investment committee for the SoftBank Opportunity Fund, a $100 million initiative launched in 2020 to empower underserved entrepreneurs. This experience highlighted the abundance of overlooked founders in the tech ecosystem. Despite SoftBank divesting from the Opportunity Fund in late 2023, Brown-Philpot pressed forward, launching her own fund. By February 2025, Cherryrock had already identified over 2,000 potential companies to consider, aiming for a targeted 12 to 15 investments from its debut fund. This focused strategy stands in stark contrast to many seed funds that make numerous smaller bets or giant funds that invest in massive rounds. In a market that often pushes for rapid capital deployment, Cherryrock is taking a more measured approach. A year following the fund's announcement, Brown-Philpot and her team, including co-founder Saydeah Howard, have invested in just five companies, a method reminiscent of earlier venture capital practices. Brown-Philpot is committed to supporting founders who don’t fit the conventional Silicon Valley mold, a mission that is particularly relevant given today's political climate around diversity, equity, and inclusion (DEI). "This doesn't alter our approach at all," she remarked. "Our investors, including major firms like JPMorgan and Bank of America, expect returns, and our role is to deliver on that." Cherryrock's investor base also includes Goldman Sachs Asset Management, MassMutual, and Melinda Gates’s Pivotal Ventures. Even as some investors retreat from explicit diversity commitments amid political pressures, Brown-Philpot is poised to thrive. California's new diversity reporting legislation will require VC firms to disclose demographic data on their portfolio companies, with the first deadline approaching in April. For Cherryrock, which already prioritizes diverse founder investments, compliance is merely standard practice. With a wealth of experience across multiple organizations, Brown-Philpot also serves on the boards of HP, StockX, and Stanford University. These roles provide her with valuable insights into emerging founders and the changing landscape of entrepreneurship. At Stanford, she observes students grappling with the implications of AI on job creation, noting their proactive approach to crafting their own futures. Among her portfolio is Coactive AI, founded by MIT graduate Cody Coleman, which offers innovative AI infrastructure for the media and entertainment industry, a sector currently scrutinized for its use of AI-generated content. Cherryrock led Coactive’s Series B funding alongside Emerson Collective. Another promising investment is Vitable Health, started by Thiel Fellow and Y Combinator alum Joseph Kitonga, which provides on-demand health insurance services. When discussing her investment philosophy, Brown-Philpot is realistic about the challenges of public offerings. "Going public is very difficult; many companies end up being acquired instead," she explained, referencing TaskRabbit's sale to IKEA as an example of how the right acquisition can create significant value. Looking ahead to 2026, her strategy is straightforward: actively deploy capital to Series A and B companies that have found their product-market fit. While the conversation around diversity initiatives continues to evolve, her focus remains on identifying outstanding founders, regardless of their backgrounds. "Coming from Detroit, I understand that difficult challenges can be overcome, and we know how to navigate tough situations," she concluded.