If you've read every business book
For operators who've worked through the standard founder canon and want the orthogonal books — philosophy, fiction, and history that recur in serious operator reading lists for non-obvious reasons.
- 01
Finite and Infinite Games
PickJames P. Carse · 1986
A 160-page philosophical aphorism collection that half the technology industry quietly references.
Read if you are an operator who has read every business book and wants something genuinely different.
essay collection<200pintermediate - 02
From Third World to First
PickLee Kuan Yew · 2000
The best book ever written by a head of state — and the closest thing to a nation-building case study founders should read.
Read if you are a founder operating at long time horizons and want a model of multi-decade thinking.
memoir350p+intermediate - 03
Mutiny on the Bounty
Charles Nordhoff · James Norman Hall · 1932
A 1932 novel about a doomed sea voyage that is, at heart, the cleanest case study in print on the collapse of organizational authority.
Read if you lead teams and want a case study in how legitimacy is lost gradually then suddenly.
narrative350p+beginner - 04
The Art of War
Sun Tzu · 1963
The most overcited business book of the last century. Read the actual 70-page text once and never need to read it again.
Read if you want to inoculate yourself against the corporate misappropriation of classical military strategy.
essay collection<200pintermediate - 05
The Republic
Plato · 1955
The 2,400-year-old book that every leadership book is downstream of and almost no one reads in the original.
Read if you want to read at least one Western philosophical primary source before you die.
essay collection350p+advanced