Masters of Scale How to raise $172M for the underinvested, with Stacy Brown-Philpot
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Jun 19, 2025 
Stacy Brown-Philpot, former CEO of Taskrabbit and founder of Cherryrock Capital, dives into her journey of raising $172 million for underinvested entrepreneurs. She shares insights from a profound six-day silent retreat that shaped her investment strategy. The conversation highlights the challenges of fundraising and the importance of mentorship. Stacy discusses the necessity of balancing human oversight with AI advancements and underscores how strategic relationships can drive business growth. Her mission is clear: support those overlooked by traditional funding.
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Silent Retreat Clarity
- Stacy Brown-Philpot took six months off saying no to everything after leaving TaskRabbit. - She spent six days on a silent retreat, gaining unexpected clarity and self-love.
Say No to Find Yes
- Saying no to everything at times feels hard but helps clarify true purpose. - The right opportunities remain and even improve when you say no to noise.
Saying Yes with Boundaries
- Stacy struggled to say no to opportunities from trusted mentors like Sheryl Sandberg. - She joined SoftBank Opportunity Fund investment committee without becoming an employee, balancing involvement and space.