This book by Jocko Willink and Leif Babin focuses on the principle of 'Extreme Ownership,' where leaders take full responsibility for their actions and decisions. The authors use their experiences in the U.S. Navy SEALs to illustrate how this mindset can lead to success in any organization. The book covers various principles such as believing in the mission, checking ego, and leading by example. It emphasizes that leaders must own all failures, develop plans to overcome them, and ensure their teams are well-conditioned and aligned with the mission. The authors also stress the importance of humility, discipline, and effective communication in leadership[1][2][4].
In this episode, I speak with T.C. Wilson, Chief Investment Officer of The Doctors Company (TDC Group), the nation's largest physician-owned medical malpractice insurer with $7 billion in assets under management. T.C. shares how he built an internal investment office, how insurance investing differs from endowment and foundation models, and why he treats surplus like an endowment portfolio.
We dive into his framework for portfolio construction, his views on innovation in asset management, the underrated value of evergreen structures, and the specific ways GPs can tailor their approach to win over insurance LPs. T.C. also shares why he’s cautious on large-cap private equity, how he thinks about downside protection, and what extreme ownership has taught him as a leader.
If you want to learn how a CIO with decades of experience invests across public and private markets with an eye toward solvency, surplus growth, and long-term resilience, you’ll want to listen to this one.
Highlights:
- T.C.’s path from Mercer to CIO of TDC Group
- Building an internal consulting-style investment team
- What makes insurance companies unique LPs
- Why surplus is treated like an endowment portfolio
- Portfolio construction: 80% non-VAR, 20% “fun stuff”
- How to think about investing as a taxable entity
- The role of rated feeder notes in optimizing statutory reporting
- What GPs often get wrong when pitching insurance allocators
- Evergreen structures and the “virtue of illiquidity”
- Why culture and leadership matter more than most realize
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Guest Bio:
T.C. Wilson is the Chief Investment Officer of The Doctors Company (TDC Group), where he oversees more than $7 billion in assets under management. He joined the firm in 2017 after serving as an external investment consultant to the company for 18 years. Prior to TDC, T.C. worked at Mercer and led an institutional consulting group focused on insurance clients. He has over 35 years of experience in investment management and is known for his deep understanding of how to balance surplus growth, solvency, and risk-adjusted returns within the insurance framework.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.
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Stay Connected: X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Thomas (T.C) Wilson: https://www.linkedin.com/in/thomas-t-c-wilson-ab70b7a/
Links:
TDC Group: https://www.tdcg.com/
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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
(0:00) Episode preview
(2:15) Capital allocation: Insurance vs. Endowments & $3.2 billion surplus impact
(4:52) Tax considerations in portfolio construction
(6:06) Traits of successful GPs and regulatory support
(10:22) Rated feeder notes and attracting insurance investors
(14:31) Evolution of asset managers and TDC Group's current strategy
(20:35) Private equity insights and evergreen fund benefits
(25:50) Investment strategy for downturns and portfolio resilience
(30:34) Illiquidity's role and criteria for new PE manager investments
(33:12) Portfolio construction vs. manager selection debate
(37:38) General partners' practices and AI's future impact on asset management
(42:11) Investor and allocator perspectives: Overrated and underrated aspects
(45:12) Extreme ownership and its influence on company success
(49:29) The significance of principles and culture in firms
(50:09) Conclusion and contact details
(50:19) Closing remarks
How I Invest with David Weisburd 