A conversation with Jack Woodruff for AI Engineer.
Jack Woodruff is the founder and former CIO of the long/short equity fund Candlestick Capital and a former portfolio manager at Citadel. We sat down to talk about what AI really changes in fundamental investing, and what it doesn’t.
What We Covered
- Humans are still the bottleneck. AI turns hours of prep into minutes, but that raises the table stakes rather than replacing judgment.
- Coverage and the junior analyst. Whether one analyst could cover 400 stocks, and which parts of the job junior analysts will stop doing.
- Never trust a number you can’t audit. Why verifiability matters more than speed, and what a fund would never let an AI vendor see.
- Where edge comes from. When every fund has access to the same models, the differentiation has to come from somewhere else.
- Building a fund in 2027. Build vs. buy, how teams will be structured, and how the picture differs for small funds and giant ones.
- The overhyped idea. Why the “no-analyst hedge fund” won’t beat the best human-led funds.
Questions about AI in investing or what we’re building at Kepler? Feel free to reach out.