How to avoid selling winners too early

How do the best family offices consistently spot power-law opportunities and avoid the trap of “fake busy” work? In this episode, I’m joined with William (Bill) Brown, CIO of the Terrace Tower Group, about the lessons he learned working for billionaire Leonard Stern, how he helped evolve a legacy real-estate portfolio into a globally diversified family office, and what pattern recognition looks like across trades like the Big Short, crypto, and private credit. We discuss how Bill thinks about decision-making, mental models, productivity, and the mindset required to survive long enough to capture asymmetric upside.

Highlights:

• Lessons from working under Leonard Stern — focus on what truly matters.
• Why “don’t confuse activity with progress” became a lifelong principle.
• How Stern gathered insights by walking the office and challenging ideas in real time.
• The importance of taking leaders on a journey, not presenting decisions once.
• Batting average vs. slugging percentage — finding your investing style. (Ichiro vs. Aaron Judge)
• Behind the scenes of the Big Short trade — identifying early signals.
• Navigating months of drawdowns and conviction challenges.
• How to know whether you’re the “dumbest person in the room” and avoid confirmation bias.
• Why the best ideas often come from “other herds” and cross-network pattern recognition.
• Crypto pattern recognition — spotting the signal when two very different founders agree.
• How Terrace Tower built a diversified global portfolio from a real-estate foundation.
• Using private credit to replace income after a major asset sale. “Fake busy” vs. deep work — designing days for real thinking.
• Staying in the game long enough to benefit from power-law outcomes.

Guest Bio:

William “Bill” Brown is the Chief Investment Officer of Terrace Tower Group, a global family office originating from the Westfield legacy. Bill oversees the group’s non-real-estate portfolio, spanning public equities, private equity, venture capital, and private credit. Before joining Terrace Tower in 2010, Bill worked in investment banking and spent his early career at Salomon Brothers. His investing philosophy is shaped by decades of experience working with the Stern family and managing multi-asset portfolios across cycles.

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Stay Connected with Bill Brown:

LinkedIn: https://www.linkedin.com/in/william-brown-1a48593/ Terrace Tower Group: https://www.ttgroup.co/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. david@weisburdcapital.com.

(0:00) Introduction (0:12) Leonard Stern's investment philosophy and unique work habits (2:16) Leonard Stern's idiosyncratic bets and discussion on risk (4:49) Jeff Bezos and asymmetry in business (5:23) Introduction to and expansion of the big short trade (13:30) Evaluating complex trades as a family office (15:18) Cultivating the right investment mindset (18:53) Early investments in crypto and avoiding busy work (23:02) Energy management and strategic networking (25:10) The importance of not overthinking and perfection in investing (27:03) Resisting the temptation to sell too early (29:13) The importance of staying in the game and imagination in investing (33:19) Terrace Tower Group's current focus and portfolio execution (42:02) Advice for younger self and focusing on what matters (46:42) Closing remarks