Angel Investing

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Lenny's Written Position

The best angel investors operate through warm introductions rather than cold emails because warm intros serve as an effective filter for deal quality and prevent overwhelm.

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The most active angel investors over the past five years are overwhelmingly operator-investors who leverage deep experience at companies like Google, Facebook, Stripe, and Microsoft.

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Angel investors are usually wrong about which investments will do best; only a third of the biggest winners were rated as high-conviction at the time of investing.

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Angel investing is more about access to deals than picking ability; getting into hot rounds matters more than trying to find hidden gems.

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Power laws are extremely real in angel investing: 70% of paper gains can come from a single company, and 80% from just four companies out of 140+.

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The best way to build deal flow as an angel investor is to share great deals with other investors, as great deals function as currency in the investor community.

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Podcast Moments

Gokul Rajaram00:30:00

“The best way to get started angel investing is to invest in people you've worked with. You already have the best possible signal on their ability to execute. Don't try to pick markets or technologies; pick people you know are exceptional.”

Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more · Gokul Rajaram