In this episode of Masters of Scale, host Jeff Berman interviews Stacy Brown-Philpot, former CEO of TaskRabbit and now a venture capitalist at Cherryrock Capital, about her transition from an operator to an investor. Stacy shares her experiences and lessons learned, including taking a silent retreat to gain clarity after leaving TaskRabbit, her decision to launch her own fund focused on underinvested entrepreneurs, and the challenges of raising capital. She discusses her investment in CoActive, her approach to being a board member, and her optimistic view on the role of humans in the age of AI, emphasizing the importance of asking the right questions and providing support to founders.
