#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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ANECDOTE

Detroit Roots And Family Drive

Stacy Brown-Philpot grew up in a crowded West Side Detroit home filled with Motown, strong women, and community support.
Her mother researched schools and opportunities, enabling Stacy to attend Cass Tech and pursue education as a route forward.

INSIGHT

Faith Fuels Resilience

Stacy credits faith and community for resilience and seeing good in scarce circumstances.
Believing "the Lord will make a way" gave her peace during hard moments and motivated perseverance.

ANECDOTE

Getting To Wharton Against The Odds

Stacy applied to Wharton after seeing it listed as a top business program in her high-school counseling office.
She secured grants, scholarships, and campus jobs to cover tuition and made Penn work financially.

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Before leading global teams and raising more than $170 million to back exceptional founders, this journey started in a crowded home on the West Side of Detroit filled with Motown, discipline, and faith.

In this conversation, she shares how she went from Detroit public schools to Cass Tech and Wharton, then entered Silicon Valley and scaled teams from 14 to more than 1,000 at Google. From global leadership assignments to becoming a first-time CEO, she breaks down the lessons behind leading with conviction, humility, and principle.

She reflects on navigating high-stakes decisions, building trust at the executive level, and helping guide a major strategic transaction with one of the world’s most iconic companies. From serving on public company boards to investing at the Series A and B stage, she explains how operating experience shapes venture judgment and why she built a fund designed to support underestimated talent at scale.

A masterclass in purpose-driven leadership, discipline, and belief, proving that success does not require sacrificing values, family, or faith, and that building with integrity is not a weakness, but a competitive advantage.

Follow Stacy - X (Twitter): https://x.com/sbp04
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — Growing Up in Detroit: Faith, Family & Strong Women
2:18 — Motown Culture, Community & Early Joy
4:01 — Hard Things Young: Grit & Gratitude in Scarcity
5:47 — “God Will Make a Way”: Faith in Difficult Moments
6:58 — Two Things Can Be True: Effort vs Surrender
8:32 — Education as Escape: Earning a Shot at Cass Tech
10:12 — Wharton Dreams Without a Roadmap
12:45 — Breaking Into Tech & Entering Silicon Valley
16:22 — From 14 to 1,000 Employees: Learning to Lead at Scale
19:06 — Leading in India: Humility, Culture & Listening
22:54 — Becoming CEO: Pressure, Confidence & Faith
28:30 — The IKEA Deal: Inside a Transformational Acquisition
33:44 — How Great Boards Really Work (No Surprises Rule)
48:10 — Building Cherry Rock Capital & Investing With Purpose
50:20 — How She Chooses Founders & Helps Them Scale
1:11:26 — Mind Over Matter: Overcoming Hard Seasons
1:12:12 — Marriage Strength & Building a Life Together
1:12:42 — Legacy: Faith, Kids, Meaning & Life’s Real Scorecard

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Hashtags:
#Leadership #SiliconValley #WomenInTech #TaskRabbit #Google #VentureCapital #FaithInBusiness #Entrepreneurship #FounderMindset #ScalingStartups