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Must-Read Investment Memos

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Iconic memos and analyses from the best investors in venture history

Roelof Botha's YouTube Memo

Roelof Botha · Sequoia Capital · 2005 · YouTube

A masterclass in identifying early consumer traction. Botha saw YouTube's explosive growth in user-uploaded video at a time when most dismissed it as a piracy risk. The memo demonstrates how to build conviction around behavioral signals rather than financial metrics.

Mike Moritz's Google Memo

Mike Moritz · Sequoia Capital · 1999 · Google

Written when Google was a Stanford research project. The memo captures Moritz's framework for evaluating technical founders and assessing market timing in a crowded search market.

Peter Thiel's Facebook Investment

Peter Thiel · Founders Fund (personal) · 2004 · Facebook

The legendary $500K angel check for 10.2% of Facebook. Thiel's thesis centered on network density at Harvard and the structural advantage of starting with an exclusive, high-engagement community.

Marc Andreessen on Coinbase

Marc Andreessen · Andreessen Horowitz · 2013 · Coinbase

a16z's thesis on crypto infrastructure. The memo argues that every financial system needs a trusted exchange, and Coinbase was positioning to be the regulated on-ramp for an emerging asset class.

Bill Gurley's Uber Analysis

Bill Gurley · Benchmark · 2014 · Uber

Published as 'A Deeper Look at Uber's Dynamic Pricing Model.' Gurley's framework for understanding marketplace dynamics, network effects, and why Uber's TAM was vastly larger than the taxi market.

Bessemer's Anti-Portfolio

Various · Bessemer Venture Partners · Ongoing · Multiple

Not a single memo but an invaluable resource. Bessemer publicly catalogs every major company they passed on (Apple, Google, Facebook, etc.) with the actual reasoning. Essential reading for understanding how even great investors make mistakes.

Benchmark's eBay Investment

Bob Kagle · Benchmark · 1997 · eBay

One of the greatest venture returns in history ($6.7M became $5B). The memo focuses on marketplace liquidity dynamics and the power of buyer-seller network effects at a time when e-commerce was unproven.

Union Square Ventures' Twitter Thesis

Fred Wilson · Union Square Ventures · 2007 · Twitter

USV's investment thesis centered on Twitter as a new communication protocol, not just a social network. Wilson's framework for 'large networks of engaged users' as the primary investment filter for USV.