39: Andrew Reed - Don't Flinch

**Andrew Reed** (0:00)
But it's February 2014, was when the WhatsApp Facebook deal was announced, and that was like a four billion-ish dollar gain for Sequoia.

**Jackson Dahl** (0:07)
That's the bar, welcome to the company.

**Andrew Reed** (0:10)
Yeah, and it was, obviously that was amazing, and then literally, you know, email goes out saying, you know, meet in the, we were in this dingy office, it was like Sequoia's long time office, be in the lobby at noon for like a champagne toast. It's like, oh, champagne toast. It was literally five minutes long, and then everyone goes back to their desk and this keeps working. And that was an interesting moment. I don't know what to take from it besides, like, Jim Getz is a legend. And also that, like, yeah, greatness is sort of expected, you know. Opportunities that you're really excited about reveal themselves highly infrequently and never at opportune times. You know, I dreamed, I grew up around New York City, I had dreams of, you know, facing, and I graduated high school in 2008 I remember I read the big short, right when it came out and I had to go, how am I gonna react to like a crisis in finance? I picture myself on Park Avenue, wheeling and dealing, going to a boardroom, making a deal happen when, you know, things were blowing up. And then you found, you know, that's how you envision it in your head. And like, I really wanted to be a great investor. I like imagined myself in the moment so many times. What it actually looked like was, I just bought a house, it had a pool outside, there was no furniture in the house. We were locked down because of COVID. I was doing circles around my pool, talking to Aladdin Basie about his investment, when the market was gapping down five points every single day. But Robinhood was like, this is back when you could double your money on Boeing in 16 minutes. We did a $200 million check right that first week of COVID. The app was down for a whole day, it was chaos. And felt so proud that I just not being scared of that moment, in part because I prepared myself for it for so long. Like, what would the guy you want to be do in this moment?
I think you just can't let yourself down, you know? Like, I think all of us like to imagine how we'll react in these like really high stress, high stakes moments. Yeah, don't flinch to me just means like, just do the thing you know you should do.

**Jackson Dahl** (2:03)
Welcome to Dialectic, episode 39 with Andrew Reed. Andrew is a growth investor at Sequoia Capital, where he has invested in a number of world changing companies, companies like Robinhood, Figma, Klarna, Phantom and many others. And he's quietly one of the best growth investors out there. We talked extensively about how Andrew invests, the founders he works with, what makes them so special, how he thinks about the quantitative and the qualitative side of things, what it's like doing so at a place like Sequoia, and how Sequoia's culture of performance and teamwork influences so much of his work. And we also talked about how he brings humanity into a job that, on the surface, might seem quite quantitative. He is a deeply competitive dude and loves to win and is quite good at making money. But he also brings an element of craft and care and taste and attention that really stood out to me as I was preparing for this conversation and certainly as I had it. We also talked about Sequoia Capital and some of the legendary people who have come before him and how he has worked with them and learned from them, as well as people he's working with now and who are apprenticing under him. This is certainly a unique and special institution and it was fun to hear Andrew's perspective on it. I think investing is such an interesting discipline because there are so many different ways to do it and to be good at it. But I think Andrew's in particular is quite resonant with me. And so it was really fun to get him to pull apart the details and show me how some of the magic is made. I hope you were inspired by his level of deep attention and care and fierce competitiveness that he puts into doing this job so well. And ultimately, as I think he would say, to serve great entrepreneurs trying to change the world. Before we get into the conversation, I'd like to thank Dialectic's presenting partner, Notion. Notion is a collaborative workspace for teams and ultimately a tool for people doing their life's work. One of the things I love about Notion's approach to AI and to agents is that they are quite attuned to allowing you to focus on the work that deeply matters, allowing you to collaborate with you if you need to, and then delegate the rest of the work to agents and to AI. I found even with Dialectic, whether it be preparing for interviews or on the other side of them, being able to throw all of my ideas or the transcript or whatever else into Notion and have Notion AI pull out patterns, lessons, ideas, things I might have missed, help me even find weird corners of research I might not have uncovered. It's just a tremendous amount of leverage, and yet, it isn't about automating the part of the work that I really care about, which I think is deeply important. Notion is a brand, as I've talked about in the past, that has imbued craft and care and soul into every piece of it, and I think you can see that whether you're using Notion solo or in a giant team. It's no coincidence that all kinds of startups and large teams choose to run their worlds and their businesses on Notion. If you don't use Notion, you could check it out at notion.com/dialectic. And if you use it, I hope you use it to make something really wonderful and full of craft and care. If you do, let me know. Thanks again to Notion for presenting Dialectic, and thanks to you for listening. With that, here is my conversation with Andrew Reed.