Investing

Investing here means valuation, not prediction. The frame is Mauboussin’s: identify situations where market price and intrinsic value diverge measurably, then size positions to the conviction that the gap will close. Not “where is the S&P going next year.” More “is this asset worth what it costs, and on what assumptions.”

Valuation coverage includes Everything is a DCF Model, applying Mauboussin’s framework across asset classes, and the a16z vs AQR debate over whether AI’s trillion-dollar infrastructure bets will generate proportional returns. The SaaSpocalypse paradox examines how the market simultaneously prices AI capex failure and software disruption.

Market structure posts cover passive investing’s structural fragility, prediction market adverse selection, and the Kalshi debate over where speculation ends and investment begins.

Historical case studies include Michael Burry’s newsletter for dot-com parallels, Buffett’s retirement as a case study in capital allocation, and personal 2026 portfolio allocation as a worked example of thesis-driven positioning.

19 articles

Adjacent topics: Quantitative Finance, Macro, Economics.