Host
August 04, 2026
Host
Managing Partner, Founder & CIO of The Witter Family Office
Host Todd S. Rich and Sherry Pryor Witter, Managing Partner, Co-founder, and CIO of the Witter Family Office explore the evolution of a single-family office built on discipline and agility. A Juilliard-trained pianist by age seven and a Wall Street intern by fourteen, Sherry shares her journey from starting her first hedge fund at 22 to co-founding the Witter Family Office in 2011 with her husband Michael, youngest grandson of Wall Street legend Dean Witter. She shares how a philosophy of service shapes every decision she makes, from portfolio construction to parenting, and why she believes each generation must make its own money.
They discuss:
→Sherry’s declaration to be of service, and how it shapes her approach to investing, philanthropy, and parenting
→Why single-family offices can remain nimble and agile
→How the Witter family’s military heritage and philanthropic legacy inform investment and giving decisions
→The “micro urgent, macro patient” mindset that now guides her decisions
Todd S. Rich: https://www.linkedin.com/in/todd-s-rich-6a091333/
Sherry Pryor Witter: https://www.linkedin.com/in/sherrypwitter/
The Witter Family Office: https://www.witter.nyc/old-home
Declaration Partners: https://www.declarationpartners.com
Meditations by Marcus Aurelius: https://a.co/d/03u3E9xF
The Daily Stoic by Ryan Holiday & Stephen Hanselman: https://a.co/d/0dfRC4K2
Topics:
(00:00:00) – Intro
(00:01:45) – Sherry’s Declaration
(00:02:36) – Daughter of a soldier
(00:06:03) – Learning discipline
(00:08:31) – Early start on Wall Street
(00:12:26) – Becoming a trader not a banker
(00:15:08) – Style drift and swinging for home runs
(00:16:15) – Starting a hedge fund at 22
(00:18:33) – The Dean Witter legacy
(00:22:49) – Gen one mindset
(00:27:32) – Crypto and AI
(00:34:40) – Why single-family office
(00:40:16) – Family office structure and governance
(00:44:50) – Philanthropy and giving back
(00:47:10) – Partnership with purpose
(00:50:35) – Health struggles and gratitude
(00:54:57) – Closing questions
Ray discusses building a lasting real estate career grounded in gratitude, and why staying engaged and purposeful matters at every stage of life.
A thoughtful conversation with Sean Plummer on how high-net-worth families invest differently from institutions—and why that difference matters.
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