Foundations

Incerto - Nassim Taleb

Fooled by Randomness was recommended to me by a poker player, but the concepts of risk and randomness are essential to startups. The roles of investors and founder in venture investing is one of the clearest examples of ergodicity.

Marcus Aurelius - Meditations

I used to give this book away at startup competitions in Oxford.

Poor Charlie’s almanack - Charlie Munger

A deep wise book about life and business. The conceptual framework of mental models behind Berkshire Hathaway. Lots of great practical insight into human psychology.

100 Mental Models - Shane Parrish

Starting point for inspiration about mental models - “Invert, always invert!”

The Almanack of Naval Ravikant - Naval Ravikant

A neat digestions of some of the above ideas.

Thinking in Systems: A Primer - Donella Meadow

A bit dry but this is the best intro I’ve found to systems concepts.

“The Odyssey” - Building and Scaling Startups

These books and essays cover all stages, roughly in order of how you might encounter challenges.

Zero to One - Peter Thiel

“All happy companies are different: each one earns a monopoly by solving a unique problem. All failed companies are the same: they failed to escape competition.”

Pattern Breakers - Mark Maples

Powerful model for identifying breakout startups: Insight, Inflection, Founders living in the future.

Lean Analytics - Alistair Croll, Benjamin Yoskovitz

Probably getting a bit dated, but great for highlighting different classic startup business models, and which metrics are key for driving growth.

The Idea Maze - Chris Dixon

Finding your way to the right product and business model.

AARRR Pirate Metrics Framework

A simple but powerful way to analyse and drive your growth funnel.

The Cold Start Problem - Andrew Chen

I wish this book existed when I started with a marketplace startup.

Patrick Collision on Decision making

A good place to begin with which decisions require deep thought (most don’t) and how to make them.

The Hard things about Hard things - Ben Horowitz

Startups are emotionally HARD, the more you lean into the discomfort the better it will turn out.

High Growth Handbook - Elad Gil

Probably the guide book for scaling I’ve come back to most often on the journey.

Good Strategy Bad Strategy - Richard Rumelt

A decent high level guide to what a strategy actually is, and how to develop one.

The Power Law - Sebastian Mallaby

Fun history of VC industry and evolving trends. The Power Law itself is a key concept to internalise.

Startup Boards - Brad Feld

You need to build and manage your board, not the other way round.

Obviously Awesome - April Dunford

Positioning and branding are underrated competitive advantages, and key to differentiation.

Working Backwards - Colin Bryar and Bill Carr

Learn from how Amazon “built the machine”.

Andy Grove - The High Output manager

A classic on how to transition to managing at scale.

This is a good distillation of the key concepts in this essay inspired by Keith Rabois

Keith Rabois also shares a powerful concept about scaling teams in Barrels and Ammunition

5 dysfunctions of a team - Patrick Lencioni

This is a great book about teams, and in particular leadership teams working together more effectively. I’ve used it to run workshops multiple times.

Give away your legos - Molly Grahon on delegation, something Founders often have a hard time with when things take off.

Status Games “why we play and how to stop” - Loretta Graziano Breuling

Why are you doing this anyway? As things scale, and you bring in more leaders, status games will take off all over your company.

David Norris on the role of operations in scale-ups

A framework for managing organisational debt at different scaling inflection points.

David Sacks - The Cadence

How to get the Sales-Finance system, and the Product-Marketing system working together.

Ben Horowitz on Peacetime and Wartime

Is you startup in peacetime or wartime, do you have the right leaders for each, how should you decision making adjust?

Amp it up - Frank Slootman

This book fits well, if you need to reset your company, and shift into “wartime mode”

The complete M&A Handbook - Tom Tauli

While this book is a little dated, it’s a good overview of what’s going on conceptually in a Sale process. In particular how to think about role and leverage at different points.

Mastering Private Equity - Claudia Zeisberger, Michael Prahl, Bowen White

Great book about the mechanics of the PE industry and deals. Something that was quite mysterious to me. Has other useful applications in deal making.

Dangerous Books

All these books have some good ideas, but they seem to be particularly prone to misinterpretation.

Lean Startup - Eric Ries

You need to build something that users want but at early stage you can’t A/B test your way to success. You are unlikely to have sufficient volume to run statistically significant test fast enough.

Radical Candour - Kim Scott

While transparency can be powerful, and “ruinous empathy” is a real challenge, this book seems to get weaponised by leaders who want to justify toxic behaviour.

No Rules Rules - Reed Hastings

This is my favourite “dangerous book” but I think it needs caution - I’m a fan of building highly autonomous culture, but like everything this comes with trade-offs and constraints. Anarchy is not going to help you succeed.

Founder Mode - Paul Graham

I think there’s a germ here that Founder led companies are often most successful, and that Founders can have a moral authority to drive more radical strategies, and should not lose sight of detail. However this does not mean that Founders don’t need boards, should ignore everyone else, or micro-manage.

Philosophy and Startups

I’d like to write more on this, I think startup leaders can draw a lot from philosophy. Some examples of thinkers with interesting lessons for startups: Marcus Aurelius, Machiavelli, Nietzsche, Betrand Russell, Karl Popper, Carl Jung, Marsall McLuhan, Rene Girard