When to Hold and When to Sell

Full transcript and links: https://dialectic.fm/andrew-reed.

Andrew Reed (X, Website, Sequoia) is a growth investor at Sequoia Capital, where he has invested in companies including Robinhood, Figma, Klarna, Phantom, Vanta, and ElevenLabs. He is quietly one of the best growth investors of his generation.

We begin with how Andrew's competitiveness and humanity coexist—the twin brother rivalry, the football player who also did musicals, the Goldman analyst who came to value people over spreadsheets. He also shares how an early lack of confidence helped him become a great observer of people and situations.

We talk through his approach to investing: why spreadsheets are “always wrong” in one direction, how he underwriters revenue growth, and what he sees in the world-beaters he invests in. We discuss several of his most formative investments—Robinhood as a 27-year-old’s first check, and again during the first week of COVID; Figma at a price people thought was insane; and a 14-second conviction on Vanta’s—and what each taught him about conviction, timing, and not flinching.

Andrew shares his perspective on serving as a board member, knowing when to double down, closing deals, and how craft can be a commercial input. We also talk extensively about Sequoia Capital and its legendary leaders, from Don Valentine, to Doug Leone and Mike Moritz, to newly-appointed Co-Steward Pat Grady. Andrew reflects on what it means to apprentice at an institution where greatness is the expectation and the champagne toast lasts five minutes.

I hope this conversation inspires you to show up ready for the day you don't expect, to rise to the stakes rather than shrink from them, and to move through your life and work a little more lightly.

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Timestamps

• (0:00) - Opening Highlights
• (2:02) - Intro: Andrew Reed
• (3:50) - Thanks to Notion
• (5:23) - Start: Humanity, Spotting Weird, and Competitiveness
• (19:07) - Investing & Great Founders
• (37:53) - Andrew's Style, Pat Grady, and Continuous Learning
• (47:31) - Doubling Down and Not Flinching
• (56:09) - Empathy on Boards, Learning the Real Business, "Expensive" Prices, and Selling
• (1:07:18) - Managing Ego and Becoming a Leader
• (1:14:08) - Craft as a Commercial Input, Knowing vs. Feeling, Preparing for Big Days, Becoming a Great Closer
• (1:28:39) - Sequoia Capital
• (1:38:57) - Don Valentine, Mike Moritz, and Doug Leone
• (1:51:29) - Closing Questions
• (1:59:08) - Thanks Again to Notion