Divot #24: From Detroit to Silicon Valley: Faith, Grit & Leading With Purpose in Tech & Venture
Nov 12, 2025
Stacy Brown Philpott, founder of Cherry Rock Capital and former CEO of TaskRabbit, reflects on her inspiring journey from a challenging upbringing in Detroit to leading teams at tech giants. She discusses lessons in grit and faith, breaking barriers to attend Wharton, and managing teams at scale. Stacy dives into the complexities of transitioning from COO to CEO, shares insights on investing in underrepresented founders, and emphasizes the importance of integrity in leadership. Her narrative is a powerful reminder that success can coexist with values and family.
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Episode notes
Run Efficient, Honest Board Meetings
- Board members should read materials in advance and reserve meetings for real discussion rather than presentations.
- Avoid surprises, ask questions over answers, and use executive sessions to gauge board health.
Why She Founded Cherry Rock
- Stacy built Cherry Rock because she couldn't find a VC firm with her desired collaborative culture and values.
- She learned VC mechanics at General Catalyst and SoftBank then created a firm reflecting her principles.
Lead With Meaningful Series A Checks
- Lead Series A/B rounds for under-invested founders and write meaningful checks to reach the next big milestone.
- Provide capital plus networks and operational support to avoid early shortfalls that stall growth.