Stacy Brown-Philpot on TaskRabbit, Trust, and Doing Hard Things

What does it take to make a bold business change and bring the people affected along with you? On The Solve Effect, MIT Solve’s Hala Hanna talks with Stacy Brown-Philpot, former TaskRabbit CEO and founder and managing partner of Cherryrock Capital, about leadership, trust, and expanding opportunity for entrepreneurs. In this episode: Changing the TaskRabbit model: Why moving from an auction system to direct hiring raised task fulfillment from 50% to more than 90%—and sparked a backlash from Taskers. Listening through disruption: What Brown-Philpot learned about communicating change, building trust, and caring for the people who rely on a platform. Backing founders overlooked by traditional venture capital: How Brown-Philpot raised $170 million for Cherryrock Capital after more than 360 meetings—and how the firm helps underinvested founders access capital and networks to scale. Leading from her roots: The lessons Brown-Philpot carries from growing up in Detroit, including her grandmother’s advice to stand for something. Finding belonging: Why Brown-Philpot no longer feels she has to prove she belongs—and what she hopes her daughters learn from watching her. Full transcript available here. \- - - - Join our CrowdSolve mailing list for more social impact news: https://solve.mit.edu/newsletters Make sure to follow us on LinkedIn, Instagram, and Facebook.