Doug Clinton started with one question in late 2022: can ChatGPT beat the S&P 500? The early results were promising enough that he built a company around it. Today he runs Intelligent Alpha, where frontier models do the investment analysis and the portfolio management and he's still a partner at Deepwater, making the same calls as a human.

He, Brett, and Khe get into where the models are already good enough, why he grades them a B+ analyst and not an A, and the contrarian call on which model is actually best for stock work.

A conversation on AI for hedge funds and the buy-side: knowledge graphs, ontologies, model routing, obsolescence risk, and what it takes to build an AI-native investment process.

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Timestamps:

[00:00] Intro
[02:39] — Can ChatGPT Beat the S&P 500?
[04:11] — Why LLMs Keep Handing You $NVDA
[05:05] — Prompt Engineering to Agentic Workflows
[06:45] — Organizational Context: Every Portfolio You've Ever Built
[09:07] — Public Markets Alpha Is a Power Law Game
[10:09] — Where Human Intuition Still Beats the Model
[11:14] — The Hybrid: Part Quant Book, Part Fundamental Book
[12:30] — The Three Buckets of Data
[13:58] — Can Agents Do Channel Checks?
[14:49] — Is MCP Institutional Grade Yet?
[16:11] — Grading the Models: A B+ Analyst
[16:55] — Knowledge Graphs Are the Frontier Right Now
[18:41] — Schemas, Ontologies, and the Gray Matter
[19:21] — Taste: Getting AI From B+ to A
[20:26] — What Building an EBITDA Ontology Actually Looks Like
[24:04] — The Dev Shop Wants to Interview Your PM
[25:37] — Trade Perfection for Speed
[26:36] — We've Built a Lot of Things We No Longer Use
[28:25] — The Vendor Cycle and Controlling Your Own Destiny
[30:23] — Model Routing and the IA 500 Benchmark
[32:36] — The Contrarian Take: GPT Over Claude for Stock Work
[33:53] — Codex vs. Co-work and a Branding Problem
[37:32] — Why There's No Harvey or Rogo for Investing Yet
[40:45] — Do Funds Want the iPhone or the Android?
[43:13] — You Need Someone in Leadership Who's AI-Pilled
[45:19] — Fable Built a 10-Stock Portfolio. It's All AI.
[48:28] — Brett Updates His Skepticism
[49:09] — Advice for Building an Asset Manager With AI
[51:33] — Getting Comfortable With Uncertainty
[53:03] — Go Get Lost in the Models

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