Capital Allocators

Matthew Dicks — bestselling author, award-winning storyteller, and 58-time Moth StorySLAM champion — teaches Ted Seides why storytelling is a learnable skill, not a gift, and how institutional investors can use storytelling to communicate with boards and stakeholders more effectively.

Stephen Gilmore, CIO of the largest public pension fund in the US ($500B+ AUM), discusses the unique challenges of managing public money under political scrutiny, media attention, and regulatory constraints that private investors never face.

Josh Wolfe of Lux Capital discusses deep tech investing, the directional arrows of technological progress, and why the most important investments are in companies solving problems that most people don't know exist yet.

Tyler Cowen argues that university endowments are poorly positioned for AI disruption: their largest asset (the university brand) could be devalued if AI makes education widely accessible, and their portfolios are over-indexed to the pre-AI economy.

Chris Mayer discusses his research on stocks that returned 100x. The common traits: small starting size, high returns on capital, long runway for growth, and — most critically — shareholders who held through enormous volatility without selling.

Josh Wolfe discusses Lux Capital's increasing defense technology investments with Ted Seides. He argues that geopolitical instability has made defense tech a decades-long investment theme and that venture-backed startups are disrupting legacy defense contractors.

Seides examines the explosive growth of family offices — now managing $6T+ globally. He argues they have structural advantages (no redemptions, infinite time horizon, aligned incentives) but often lack the governance and expertise of institutional investors.

Seides evaluates the risk parity strategy (allocating based on risk contribution rather than dollar amount) popularized by Bridgewater's All Weather fund. The concept is elegant but real-world implementation has been challenged by the correlation regime change of 2022.

Bobby Jain discusses leaving Millennium Management to launch Jain Global with over $5 billion — one of the largest hedge fund launches in history. The conversation covers multi-strategy investing, risk management, and building a culture of intellectual honesty.

Permanent Equity founder Brent Beshore explains his approach to acquiring and operating small businesses forever — no exit strategy, no leverage, no MBA playbook. He argues the best businesses are boring ones with loyal customers and stable cash flows.

Seides evaluates the endowment model (heavy allocation to alternatives: PE, hedge funds, venture, real estate) 20 years after David Swensen popularized it. The verdict: it works for Yale-caliber allocators but has been disastrous for smaller endowments that lack the access and expertise.

Seides examines the private markets boom and whether PE/VC returns are real or an artifact of smoothed valuations and survivorship bias.

Shake Shack founder Danny Meyer explains his philosophy of 'enlightened hospitality' to Ted Seides — the idea that taking care of employees first creates a cascade: happy employees create happy customers, happy customers create happy investors. Seides draws parallels to institutional investing.

Katelin Holloway discusses building the culture at Reddit, transitioning to venture capital with Alexis Ohanian at Seven Seven Six, and why people-first investing produces better returns than spreadsheet-first investing.

Naval Ravikant discusses wealth creation with Ted Seides. He argues that wealth is built through leverage (code, media, capital, labor) applied to good judgment, and that the best way to develop judgment is through diverse experience and voracious reading.

Former 76ers GM Sam Hinkie discusses how he applied investing principles to sports management. His 'Trust the Process' strategy was a long-term play that required enduring years of losing — and the organizational courage to ignore short-term pressure.

Seides shares his due diligence framework for evaluating investment managers: process over performance, culture over credentials, and alignment over assets.

Jim O'Shaughnessy revisits the thesis of his classic book with Ted Seides: quantitative value and momentum strategies still outperform, but the edge has narrowed because more capital chases the same factors.

Howard Marks discusses his evolving thinking on risk with Ted Seides. His key insight: risk is not volatility (as academics define it) but the probability of permanent capital loss. And the riskiest moment is when everyone thinks there's no risk.

Ted Seides reflects on his famous bet with Warren Buffett: that a portfolio of hedge funds would outperform the S&P 500 over 10 years. Buffett won decisively (S&P 500 returned 125% vs hedge funds' 36%). Seides shares the hard-won lessons about fees, indexing, and humility.

David Morehead manages Baylor's $2.2 billion endowment with a small team, demonstrating that endowment size doesn't determine investment quality — process discipline does.

Amy Falls, CIO overseeing Northwestern's $14.2 billion endowment, discusses portfolio construction, manager selection, and the unique challenges of running an institutional portfolio during market uncertainty.

Tom Steyer — founder of Farallon Capital, climate activist, and former presidential candidate — discusses the intersection of investing and impact. How he went from pure profit maximization to believing that climate investing is both the moral imperative and the best risk-adjusted opportunity.