Table of Contents
Former TaskRabbit CEO Stacy Brown-Philpot shares how a six-day silent retreat led to launching Cherry Rock Capital and her approach to investing in underrepresented entrepreneurs.
Key Takeaways
- Brown-Philpot took six months off after selling TaskRabbit to IKEA, saying no to everything to find clarity
- A six-day silent retreat helped her discover what she truly wanted: investing in the next generation of entrepreneurs
- Cherry Rock Capital raised $172 million over two years, focusing on underinvested entrepreneurs who lack traditional Silicon Valley networks
- The fund's name honors her grandmother, who nicknamed her "cherry pie" and serves as the family's rock
- Brown-Philpot emphasizes asking better questions rather than giving advice as a board member
- She advocates for founders to carefully consider when they actually need a board versus feeling pressured to create one
- The transition from quarterly operational thinking to 10-year investment horizons required significant mental adjustment
- Negative feedback from her Detroit upbringing typically motivates rather than discourages her efforts
The Power of Saying No and Finding Clarity
After successfully selling TaskRabbit to IKEA in August 2020, Stacy Brown-Philpot made a counterintuitive decision that would shape her entire future. Rather than immediately jumping into the next exciting opportunity, she committed to saying no to everything for six months. This wasn't easy for someone who had spent her career as a second child in a Detroit household of seven people, never truly experiencing solitude.
The turning point came through a six-day silent retreat at Half Moon Bay, suggested by her coach Joe Hudson. Initially resistant and afraid of what might happen during extended alone time, Brown-Philpot discovered something profound. For the first two days, her exhausted body simply slept, recovering from years of executive stress and the intensity of selling a company. When she finally stopped falling asleep during meditation sessions, clarity emerged.
This centeredness revealed what she truly wanted rather than what others expected of her. Despite numerous offers to become CEO of public and private companies, serve on prestigious boards, or fulfill society's expectations for a successful Black female executive, the retreat helped her focus on her own aspirations. The world didn't collapse during her absence, and her body finally got the rest it desperately needed.
Building Cherry Rock Capital from Vision to Reality
The fund's name carries deep personal significance, combining her grandmother's nickname for her ("cherry pie") with the matriarch's role as the family's rock. At 96 years old, Brown-Philpot's grandmother represents the foundation of success she wants to provide for entrepreneurs. This personal connection drives Cherry Rock Capital's mission of becoming the foundation of success for the next generation of underinvested entrepreneurs.
Launching a venture fund in January 2023 meant facing widespread discouragement about market timing. Everyone warned that this was the worst possible time to raise capital, advice that proved questionable given subsequent market conditions. However, Brown-Philpot's Detroit upbringing had taught her that negative feedback often serves as motivation rather than deterrent. When people said she couldn't do something, her instinct was to prove them wrong rather than accept limitations.
The fundraising process took two years, concluding in January 2025 with $172 million raised from institutional investors including JP Morgan, Ford Foundation, Mass Mutual, and Goldman Sachs. This timeline aligned with typical first-time fund experiences, though Brown-Philpot initially hoped to complete the process in half that time. The extended timeline reflected the relationship-building nature of institutional fundraising, where processes can take three to nine months depending on existing connections.
From Operator to Investor: Navigating the Transition
The shift from running TaskRabbit with quarterly objectives and OKRs to thinking about 10-year value creation required fundamental mental recalibration. As an operator, Brown-Philpot had focused on immediate execution and measurable short-term results. Venture investing demanded patience and long-term vision, evaluating entrepreneurs and opportunities through entirely different lenses.
Her 20-year operating background at Google and TaskRabbit provided crucial advantages in understanding founder challenges. When someone advised her to gain operating experience before entering venture capital during business school at Stanford, she thought it would take a few years. Instead, it stretched into two decades of invaluable experience that now informs her investment decisions and founder support.
The SoftBank Opportunity Fund provided her first meaningful venture experience during her transition period. Launched after George Floyd's murder with $100 million in funding, the initiative allowed her to test her interest in venture capital while maintaining the flexibility to explore other options. This experience confirmed her passion for meeting founders, discussing innovative ideas, and helping entrepreneurs navigate challenges she had personally faced.
Investment Philosophy and Portfolio Approach
Cherry Rock Capital's first investment exemplifies Brown-Philpot's relationship-driven approach. She discovered Coactive through a LinkedIn message to founder Cody Coleman, a Stanford PhD who had written his dissertation on what became his company's core technology. Despite not having a fund at the time, she personally invested in the company's Series A round, spending a year building a relationship and understanding Coleman's vision.
When Coactive's Series B opportunity arose, Cherry Rock Capital co-led the round with Emerson Collective. The multimodal AI company helps businesses organize and analyze video and image data to improve customer relationships. Coleman's prescient timing impressed Brown-Philpot—he closed his A round just before ChatGPT launched and transformed the AI landscape, having anticipated the market shift through his academic research.
The fund actively seeks board seats, contrary to many venture capitalists who prefer observer roles to avoid governance responsibilities. Brown-Philpot's experience on HP's board and as TaskRabbit's CEO taught her that the best board members ask insightful questions rather than dispensing advice. She understands the multidimensional nature of CEO responsibilities and avoids the trap of suggesting immediate solutions without understanding underlying complexities.
Board Dynamics and Founder Relationships
Brown-Philpot's board philosophy centers on empowering CEOs through strategic questioning rather than directive advice. Her experience transitioning from TaskRabbit COO to CEO while serving on HP's board provided crucial insights into effective governance. She learned that board members who attend quarterly meetings cannot fully grasp the daily operational realities that CEOs navigate continuously.
This understanding shapes her current approach with portfolio companies. Rather than telling founders what to do, she focuses on asking questions that help them think differently about challenges and opportunities. She also emphasizes asking founders how she can best support them, recognizing that different situations require different types of assistance—whether advice, support, or simply active listening.
For founders building their first boards, Brown-Philpot advises careful consideration of timing and necessity. Not every seed-stage company requires a formal board structure. The decision should align with specific needs: go-to-market expertise, partnership development, leadership team building, or institutional capital requirements that mandate board representation. The board should serve clear strategic purposes rather than exist because of perceived expectations.
Addressing Market Gaps and Future Vision
Cherry Rock Capital specifically targets underinvested entrepreneurs who lack traditional Silicon Valley networks and connections. Brown-Philpot identified this gap through her own experience and observations of talented founders who struggled to access capital despite strong business fundamentals. The fund provides not just financial resources but also operating expertise and network access that many entrepreneurs need to scale successfully.
The pipeline of underinvested entrepreneurs proves abundant when investors commit to seeking them out and doing the necessary work. Brown-Philpot discovered this during her SoftBank Opportunity Fund experience, where intentional outreach and relationship-building revealed numerous high-quality opportunities that traditional venture networks had overlooked.
Looking forward, Brown-Philpot remains optimistic about artificial intelligence's role in business while emphasizing the continued importance of human involvement. Her perspective echoes her previous "keeping humans in the equation" philosophy from her TaskRabbit days. While AI achieves impressive accuracy rates, the gap between 99.9% and 100% accuracy still requires human oversight for critical business decisions.
Personal Growth and Continuous Learning
Brown-Philpot's commitment to personal development continues through reading, meditation, and learning from her children, who she recognizes as sources of innovative thinking. This openness to learning from unexpected sources reflects the humility and curiosity that drive successful venture investing.
Her journey from saying no to everything to launching Cherry Rock Capital demonstrates the power of creating space for reflection and authentic decision-making. The silent retreat provided clarity about her true aspirations versus external expectations, enabling her to build something aligned with her values and vision rather than simply fulfilling others' ideas of what she should do.
The transition from operator to investor required not just new skills but fundamental shifts in thinking, timeline orientation, and relationship dynamics. Brown-Philpot's success in navigating this transition while maintaining her authenticity and values provides a blueprint for other accomplished operators considering similar career pivots.
