Brett Caughran and Khe Hy lead a deep dive into AI for investing, joined by guests at the cutting edge of the field. Our goal is to be your Sherpa through a rapidly changing landscape by distilling what's working, what isn't working, and how you can leverage AI in your own process. Follow along as we tackle AI's biggest challenges and opportunities, one episode at a time.
Where Will Investors Find Alpha in the Age of AI? | Alistair Smallwood, Head of Applied AI at Primer
As AI becomes more deeply integrated into fundamental investing, where does human judgment still provide an edge? In this episode of Invest with AI, Brett Caughran and Alistair Smallwood, Head of Applied AI at Primer, discuss how artificial intelligence is reshaping equity research, alpha generation, and the future of fundamental investing. "And I think there'll be a real opportunity for the sharpest people in fundamental investing that really understand AI systems to identify over and unde...
21 Aug 2026
From Answer Engines to Work Mechanisms: The AI Inflection on Wall Street
It was never worth an associate's time to strip every KPI out of every SIM that crosses the desk. At $20 of tokens, it is. No guest this week. Brett Caughran and Khe Hy on the work that just became economic, and why the hard part is no longer the technology. The Mac Minis people bought to run OpenClaw mostly run Codex now, and the reason is reach: sessions on your machine are reachable from your phone. No MCP for DealCloud? The agent drives your logged-in Chrome instead. Which moves the cons...
14 Aug 2026
Intelligent Alpha CEO: Letting AI Run the Portfolio
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 m...
7 Aug 2026
Daloopa CEO Thomas Li: The Magic Isn’t in the Model
Former Point72 TMT analyst Thomas Li left the buyside to build Daloopa in 2019 with the goal of capturing market share from the data oligopoly of Bloomberg, FactSet and Cap IQ. Last year data consumption on the platform grew over 100x, and it wasn't the models that did it. He, Brett, and Khe get into what separates a reliable MCP from a brittle one, why Claude in Excel still can't handle a real buyside model, and the one layer of the analyst job he thinks is already collapsing. ------------...
24 Jul 2026
Hudson Labs CEO Kris Bennatti: Financial AI Still Gets the Numbers Wrong
Kris Bennatti and Hudson Labs are now giving a no-hallucination guarantee, something she says no other financial AI offers. The reason it's rare is the uncomfortable part: her team found state-of-the-art models return the wrong financial number about 30% of the time once you go past a few reporting periods. Kris, Brett and Khe get into why precision is still a difficult problem, how a forensic risk score turns fraud signals into a hard number, and why she thinks 2026 is "integrate or die." ...
17 Jul 2026
Fable Is Here, But Is It Actually Better? | Invest with AI Vibe Check
Fable just shipped with the promise of being Anthropic’s most capable release yet. However, daily power users Brett Caughran (Fundamental Edge) and Khe Hy (Rad Reads) still can't conclude whether models have gotten meaningfully better in the last six months. We run a round-the-horn vibe check: the eval where Fable read 10,000 minutes of Khe's calls and surfaced the one thing his business was avoiding, why complex Excel modeling still breaks, the Karpathy "knowledge wiki" for a 500-document d...
10 Jul 2026
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 almost a decade before leaving to build Canary, an AI intelligence platform now used by some of the largest hedge funds and mutual funds in the world. His take: because so many investors are misusing AI, there’s more alpha available today than there has been in a long time. He, Brett, and Khe get into the 20+ page investment reports his agents write on their own, why summarizing an earnings call is "lossy" in ways that quietly inflate your...
3 Jul 2026
Deploying AI on the Buyside: A 20-Year Engineer's Playbook
What’s the biggest hurdle in deploying AI on the buyside? After 20 years of building software, PragmaNexus Founder Matt Stockton has found that the most difficult challenge is knowing your own process well enough to write it down. As he puts it, that’s 80% of the work. He, Brett, and Khe get into the shift from "single-player" AI (one person, one laptop) to "multiplayer" AI across a whole firm, the voice-memo trick Matt uses to pull his own process out of his head, and why he tells peo...
26 Jun 2026
Stoic Point Co-Founder: AI is Bringing Back the Lean Hedge Fund
In this episode, Brett Caughran and Khe Hy sit down with Raj Shah, co-founder of Stoic Point and a former partner at Light Street, to get into how a two-person fund can run resourced like a firm ten times its size. Raj makes the case that AI lets a lean, concentrated fund compete with much larger teams and argues he's more worried about AI replacing him than the junior analysts everyone else is fretting over. We get into: How a lean fund recreates the institutional resource stack without the ...
19 Jun 2026
Implied CEO on the Limits and Capabilities of AI for Investing
Ying Hua left a PM seat at Balyasny to build Implied on a contrarian bet: the big AI labs won't win finance (but it's not for the reason you'd think). She, Brett, and Khe get into where that leaves the analyst, why Claude Code won't replace your data team, and the one part of the job she's convinced stays human. Timestamps: [00:00] Intro [00:45] — She Left a Balyasny PM Seat to Build This [01:52] — Why Bet on AI Investing in 2023? [03:45] — Will the Foundation Labs Eat...
12 Jun 2026
Investing with AI: From Chatbots to Agents (What Changed for Investors)
Welcome to episode one of Investing with AI Podcast for Financial Analysts. We’ve spent years in investing, and over the past couple years, we’ve been deep in the weeds with AI. Testing tools. Working with firms. Trying to understand what matters versus what’s just noise. For a while, most of it didn’t feel that useful but that’s starting to change rapidly. In this episode, we talk through what’s shifted, from basic chatbots to more agent-based workflows, and why that’s starting to matt...
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