BackStartups

Book · How to decide

Fooled by Randomness

Nassim Nicholas Taleb · 2001

On the human inability to distinguish skill from luck, written by a trader with no patience for people who cannot.

Why it is here

The argument is that in domains with high randomness, outcomes tell you very little about process, and that our instinct to construct explanations for successful people is close to worthless. Angel investing is such a domain, and this book is the sharpest available statement of the problem.

It should be read directly alongside our angel legends section, which is a catalogue of extraordinary outcomes and says so. Every one of those stories has an explanatory narrative attached to it, and this book is the corrective for how much weight to give it.

The tone is combative and a lot of people find it insufferable. That is a fair reaction and it does not make the argument wrong.

Read it if

You have ever read about a successful investor and tried to work out what they did right.

Skip it if

You cannot tolerate a confrontational authorial voice — the substance is genuinely good and the delivery is an acquired taste.

Pair it withThe Power LawSebastian MallabyA financial historian on how venture capital became what it is, and why the distribution of outcomes makes it behave unlike any other asset class.

Fooled by Randomness: common questions

What does this book say about learning from successful investors?
That in a high-randomness domain the successful ones are partly a selection effect, and the explanations attached to their success are constructed afterwards. It is a direct challenge to the entire genre our angel legends section belongs to, which is why we recommend reading them together.
Which Taleb book should an angel read first?
This one. It is the shortest, the most focused on the specific problem of separating skill from luck, and the least burdened by the systems-building of the later books.