AI for Bias Detection and a Digital Shadow

Why do the world’s best CIOs make investment decisions based on gut — not spreadsheets? In this episode, I’m joined by Julia Rees Toader, CFA, Founding Partner at PrinCap and former Global Head of Portfolio Strategy at Goldman Sachs Asset Management. Julia spent a decade advising sovereign wealth funds, pensions, private banks, and ultra-wealthy families on portfolio construction, risk management, and asset allocation. She shares the biggest lessons she learned from working with the world’s top CIOs — from why diversification rarely drives behavior, to where the smartest allocators take idiosyncratic risk, to how emotions secretly influence the most sophisticated investment decisions.

Highlights:

• What Julia learned rising from intern to global head at Goldman Sachs
• The surprising truth: top CIOs make decisions based on emotions + gut, not just models
• Why diversification rarely changes behavior — and why portfolios still converge to “vibes”
• Where the best allocators take idiosyncratic risk without blowing up the portfolio
• Why ultra-wealthy families succeed by leaning into their operating-business advantages
• Home country bias: the hidden 10x overweight that destroys returns
• How to avoid behavioral traps using blind comparisons and rotating devil’s advocates
• Options-based hedging vs. fixed income — and why 60/40 is outdated
• Why avoiding losers matters as much as picking winners
• Why volatility is emotional, not mathematical — and how Julia coaches clients through drawdowns
• The biggest risk mistakes she saw in sovereign wealth funds & global pensions
• The seductive danger of storytelling in investing — from thematic equity bubbles to VC pitches
• How AI will reshape diligence, bias detection, and decision-making

Guest Bio:

Julia Rees Toader, CFA, is the Founding Partner at PrinCap, an independent investment portfolio strategy firm advising institutions, family offices, and high-net-worth individuals on asset allocation, manager selection, and strategic portfolio design.

Before founding PrinCap, Julia served as Head of Portfolio Strategy and Head of Relationship Management at Heritage Holdings, a multifamily office. She previously spent over a decade at Goldman Sachs Asset Management, where she rose from founding intern to Global Head of Portfolio Strategy, advising CIOs of sovereign wealth funds, pensions, private banks, and other large allocators around the world.

Julia began her career in M&A and business development for an early-stage medical device biotech company. She holds a degree in Mechanical Engineering and Computer Science from Princeton University and is a CFA charterholder.

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LinkedIn: https://www.linkedin.com/in/julia-rees-toader-cfa-22871030/

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Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (2:55) Emotional and qualitative considerations in taking idiosyncratic risks in portfolios (6:04) Flexibility and unique strengths of allocators (7:15) Building meaningful portfolios with high returns (8:30) Options-based hedging strategies (11:29) Overcoming behavioral biases and market timing (14:01) Addressing home country bias in investment committees (17:02) Dynamics and size of effective investment committees (19:12) Role of tax strategy and alpha in investment (22:00) Strategic value and managing portfolio fluctuations (25:18) Tools and client risk tolerance in portfolio risk assessment (28:07) Lessons from transitioning to a family office (30:40) Family office investment strategies and perspectives on risk (34:24) Outsourcing tasks and addressing personal liability in decisions (37:01) Evaluating family office dynamics and resource advantages (39:04) Incorporating AI in investment management (41:04) Timeless advice for new investors and thought experiments with AI (45:22) Market timing and asset class favorability (46:09) Closing remarks