The library
27 books and 6 films worth the time
Deal mechanics, company building, the psychology of deciding badly, and the collapses that teach more than any success story. Every entry says what it does for someone writing a small cheque — and, unusually, who should skip it.
If you read three
Start here
One for the paperwork, one for the judgement, one for what happens when nobody checks.
Venture Deals
Every clause in a term sheet, explained by two investors who got tired of founders not understanding them.
The judgementThinking, Fast and Slow
How human judgement fails, in exactly the conditions angel investing creates.
The warningBad Blood
The best diligence education on this list, and the only entry we would push on everybody.
4 entries
How the machine works
Term sheets, fund structures and the economics of venture — the books that explain the industry you are handing money to.
Venture Deals
Brad Feld & Jason Mendelson · multiple editions
The clearest explanation of how a venture financing actually works, written by two investors who got tired of founders not understanding what they were signing.
Why it is here →BookSecrets of Sand Hill Road
Scott Kupor · 2019
How a venture firm actually operates — where its money comes from, what its own investors demand of it, and why that shapes every decision it makes about your company.
Why it is here →BookThe Power Law
Sebastian Mallaby · 2022
A financial historian on how venture capital became what it is, and why the distribution of outcomes makes it behave unlike any other asset class.
Why it is here →BookAngel
Jason Calacanis · 2017
A practising angel investor on how to actually do it — deal flow, meetings, cheque sizes and the unglamorous work of being useful enough to get an allocation.
Why it is here →7 entries
How companies get built
What your founders are reading, and what they are being told to do. Useful to you precisely because it is written for them.
The Mom Test
Rob Fitzpatrick · 2013
A short book on how to talk to customers without getting useless answers — and the best possible training for how to talk to founders.
Why it is here →BookThe Hard Thing About Hard Things
Ben Horowitz · 2014
An unusually honest account of running a company through the periods when it is going badly — the part every other business book skips.
Why it is here →BookZero to One
Peter Thiel with Blake Masters · 2014
A short, argumentative book about monopoly, competition and why the interesting companies are the ones doing something nobody else is.
Why it is here →BookThe Cold Start Problem
Andrew Chen · 2021
How network effects actually get started, sustained and defended — the most rigorous available treatment of the term everybody uses loosely.
Why it is here →BookThe Lean Startup
Eric Ries · 2011
The book that made "minimum viable product" a phrase every founder uses — worth reading mostly so you can tell who has understood it.
Why it is here →BookCrossing the Chasm
Geoffrey Moore · 1991
Why products that delight early adopters so often fail to reach the mainstream — written in 1991 and still the best explanation of a failure mode angels see constantly.
Why it is here →BookHigh Growth Handbook
Elad Gil · 2018
A reference manual for the stage after product-market fit — hiring executives, managing boards, and the organisational problems that stall companies at Series A and B.
Why it is here →5 entries
How to decide
Not about startups at all. Angel investing is a judgement problem under deep uncertainty with feedback arriving a decade late, and this is the literature on that.
Thinking, Fast and Slow
Daniel Kahneman · 2011
The foundational account of how human judgement systematically fails, by the psychologist who did more than anyone to demonstrate it.
Why it is here →BookFooled 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 →BookSuperforecasting
Philip Tetlock & Dan Gardner · 2015
What research on forecasting tournaments found about who predicts well, and the habits that turn out to distinguish them.
Why it is here →BookPoor Charlie's Almanack
Charlie Munger, edited by Peter Kaufman · 2005
Collected talks and writing from Berkshire Hathaway's vice-chairman, organised around the argument that good decisions require models borrowed from many disciplines.
Why it is here →BookThe Black Swan
Nassim Nicholas Taleb · 2007
On rare, high-impact events that models do not anticipate, and the consequences of building portfolios as though they do not happen.
Why it is here →6 entries
How it actually went
First-hand accounts and company histories, including the unglamorous middle years that the retellings skip.
Founders at Work
Jessica Livingston · 2007
Interviews with founders about the earliest days of their companies, before anything worked — the period every other account skips.
Why it is here →BookShoe Dog
Phil Knight · 2016
The Nike founder on two decades of near-insolvency — a company-building memoir that happens to contain the best available account of working capital as an existential problem.
Why it is here →BookThe Everything Store
Brad Stone · 2013
A reported history of Amazon's first two decades, written by a journalist rather than a participant.
Why it is here →BookWorking Backwards
Colin Bryar & Bill Carr · 2021
Two long-serving Amazon executives on the company's internal mechanisms — the six-page memo, the written narrative, the working-backwards product process.
Why it is here →BookChaos Monkeys
Antonio García Martínez · 2016
A caustic first-hand account of building and selling a startup, and then working inside a very large technology company — the least reverent book on this list.
Why it is here →BookLoonshots
Safi Bahcall · 2019
A physicist-turned-biotech-chief-executive on why organisations stop nurturing fragile early ideas, argued through the structure of phase transitions.
Why it is here →5 entries
How it goes wrong
Long-form reporting on the failures and frauds. The best diligence education available, and the most entertaining shelf here.
Bad Blood
John Carreyrou · 2018
The definitive account of Theranos, by the journalist whose reporting brought it down — and the best diligence education on this list.
Why it is here →BookSuper Pumped
Mike Isaac · 2019
A reported account of Uber under its founding chief executive — governance failure at a company that, unlike most on this shelf, survived.
Why it is here →BookBillion Dollar Loser
Reeves Wiedeman · 2020
How WeWork reached a $47bn valuation and lost it in weeks once public-market disclosure made the economics visible.
Why it is here →BookGoing Infinite
Michael Lewis · 2023
Michael Lewis inside FTX before and during its collapse — a contested book that is more useful for what it demonstrates than for what it argues.
Why it is here →BookNumber Go Up
Zeke Faux · 2023
A reporter's sceptical tour of the crypto boom, arriving at FTX from the outside and asking the questions the insiders did not.
Why it is here →6 entries
The screening room
Documentaries, dramas and one sitcom. For the evenings when you are not going to read four hundred pages about liquidation preferences.
The Inventor: Out for Blood in Silicon Valley
Alex Gibney (dir.) · 2019
Gibney's documentary on Theranos, with footage of the company and its founder that no written account can reproduce.
Why it is here →FilmSomething Ventured
Daniel Geller & Dayna Goldfine (dirs.) · 2011
A documentary about the emergence of American venture capital, told by the people who invented it — the closest thing to a founding history of the asset class.
Why it is here →FilmGeneral Magic
Sarah Kerruish & Matt Maude (dirs.) · 2018
The story of a company that invented much of the modern smartphone a decade too early, and failed completely — the best film about timing ever made about technology.
Why it is here →FilmThe Social Network
David Fincher (dir.) · 2010
A drama rather than a documentary, and still the most watched thing ever made about founder equity disputes.
Why it is here →FilmStartup.com
Chris Hegedus & Jehane Noujaim (dirs.) · 2001
Documentary film-makers followed a dot-com startup from founding to collapse, without knowing in advance which it would be.
Why it is here →FilmSilicon Valley
HBO series · 2014–2019
A sitcom that is also, unexpectedly, the most accurate depiction of term sheets, down rounds and board dynamics ever broadcast.
Why it is here →The library: common questions
What is the best book on angel investing?
If I only read one thing here, what should it be?
Why are books about psychology and forecasting on an investing list?
Do you earn anything from these recommendations?
Then use it
Reading is the easy part
None of these will tell you what to do when a term sheet lands on a Thursday and the round closes on Monday. That is what the rest of the site is for.