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From Answer Engines to Work Mechanisms: The AI Inflection on Wall Street
8/21/26 8/21/26

From Answer Engines to Work Mechanisms: The AI Inflection on Wall Street

Brett Caughran and Khe Hy on the work AI just made economic for investors, and why assembly is the hard part now: Codex, MCP, headless RMS, knowledge graphs.

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Intelligent Alpha CEO: Letting AI Run the Portfolio
8/14/26 8/14/26

Intelligent Alpha CEO: Letting AI Run the Portfolio

Intelligent Alpha CEO Doug Clinton on grading frontier models a B+ analyst, why the model matters less than the data you feed it, and where humans still add something.

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Daloopa CEO Thomas Li: The Magic Isn’t in the Model
8/7/26 8/7/26

Daloopa CEO Thomas Li: The Magic Isn’t in the Model

Daloopa CEO Thomas Li on what separates a reliable MCP from a brittle one, why data consumption on his platform grew over 100x in a year, and where AI in Excel still breaks.

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Hudson Labs CEO Kris Bennatti: Financial AI Still Gets the Numbers Wrong
7/24/26 7/24/26

Hudson Labs CEO Kris Bennatti: Financial AI Still Gets the Numbers Wrong

Hudson Labs CEO Kris Bennatti tested the top models on real filings and found the wrong number about 30% of the time. Her answer: a no-hallucination guarantee no one else in financial AI will make.

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Fable Is Here, But Is It Actually Better? | Invest with AI Vibe Check
7/17/26 7/17/26

Fable Is Here, But Is It Actually Better? | Invest with AI Vibe Check

Two daily power users still won't say the models got meaningfully better in six months. Then Fable shipped. Brett and Khe run the vibe check: evals, the Bridgewater judgment layer, and why skepticism is up.

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Canary CEO & Ex-Tiger Global PM: How Bad AI Is Leaving Alpha on the Table
7/10/26 7/10/26

Canary CEO & Ex-Tiger Global PM: How Bad AI Is Leaving Alpha on the Table

Joe O'Donnell ran the short book at Tiger Global for nearly a decade. His claim as Canary's CEO: so many investors are misusing AI that there's more alpha available today than there has been in a long time.

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Deploying AI on the Buyside: A 20-Year Engineer's Playbook
7/3/26 7/3/26

Deploying AI on the Buyside: A 20-Year Engineer's Playbook

Matt Stockton has spent 20 years architecting data infrastructure for firms deploying AI. His read: the model is rarely the hard part. Writing down your own process is 80% of the work, and most firms skip it.

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Stoic Point Co-Founder: AI is Bringing Back the Lean Hedge Fund
6/26/26 6/26/26

Stoic Point Co-Founder: AI is Bringing Back the Lean Hedge Fund

Raj Shah co-founded Stoic Point after a partnership at Light Street. He runs a two-person fund resourced like a firm ten times its size, and says he's more worried about AI replacing him than the juniors everyone else is fretting over.

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Implied CEO on the Limits and Capabilities of AI for Investing
6/19/26 6/19/26

Implied CEO on the Limits and Capabilities of AI for Investing

Ying Hua ran money at Citadel and Balyasny before founding Implied. Her case: the foundation labs won't eat finance, because domain knowledge is the piece they won't build. Brett and Khe get into data, dashboards, and what stays human.

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6/8/26 6/8/26

The AI Shift in Investing: From Chatbots to Agents (What Changed for Investors)

Brett Caughran and Khe Hy on what actually changed in 2026: the shift from chatbots to agent workflows, where AI helps in investment research today, and the limits that are still real.

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