Book Review: Investing in AI: Six Mental Models to Tell Moats from Traps by Rob May

A personal review of Rob May and his practical mental models for investors and entrepreneurs building durable AI businesses. I was excited to read Investing in AI: Six Mental Models to Tell Moats from Traps, largely because I have been following Rob May for years through his Investing in AI newsletter. What separates Rob May from many investors, in my view, is his willingness to avoid groupthink and reason from first principles.

He looks past the prevailing narrative to ask how a business actually works, where its advantages come from, and whether those advantages can survive the next technological shift. That is where this book shines. It is the first book I have encountered that approaches AI investing quite this way. Rather than simply identifying an exciting technology or a growing market, it asks readers to re-engineer how they analyze the businesses being built around it.

The opportunity is enormous, but recognizing a promising AI capability and recognizing an investable company are two very different skills. Rob May grounds the discussion in stories that will be familiar to anyone who…