39: Andrew Reed - Don't Flinch

Speaker A: But it's February 2014 was when the WhatsApp-Facebook deal was announced. And that was like a $4 billion-ish gain for Sequoia. Speaker B: That's the bar. Speaker A: Yeah. Speaker B: Welcome to the company. Speaker A: 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. We were— it was like Sequoia's longtime office. Meet in the lobby at noon for like a champagne toast. It's like, oh, champagne toast. It was literally 5 minutes long.

And then everyone goes back to their desk and just keeps working. And that was an interesting moment. I don't know what to take from it besides like Jim Goetz 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 going to 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, 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 Vlad and Beiju about this investment when, you know, the market was gapping down 5 points every single day.

But Robinhood was like, you know, this is back when you could double your money on Boeing and then, you know, 16 minutes. We did a $200 million check right that first week of COVID You know, the app was down for a whole day. It was chaos and felt so proud that, you know, just not being scared of that moment, you know, in part because I prepared myself for it for so long. Like, what was— what would the guy you want to be do in this moment? I think you just like 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. Speaker B: 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, Fantom, 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. Um, 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 who 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, um, help me even find kind of 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. Um, 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 can check it out at 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 Reid.

All right, Andrew Reid, we're here. Speaker A: Thank you for having me on your podcast. Speaker B: The first timer. Speaker A: It's truly an honor breaking my podcast celibacy. Speaker B: Yes, we are going to jump right in. Uh, I want to talk a lot about investing, but before we do, there are a couple of themes or like little kind of senses I had about you that I think are worth talking a little bit about before we go into all the work stuff. I think the first is you're someone who is like an elite performer.

You are super competitive. You're a growth investor. You started at Goldman. You played high school football and college football. And so there's like a, maybe a tinge of like hard-on-ness on one end. And yet I think both in your work and personally, there's also like a deep amount of humanity. I'd be curious for you to reflect on how you've leaned into humanity over time, both in your job at Sequoia and also more broadly. Speaker A: Yeah, I was, you know, growing up, I think that was a kind of dichotomy that existed at every point in my life.

I played, played sports in high school. I also used to do like the musical. My best friend in high school was not on the football team, actually, but besides my twin brother, who is my best friend, he was on the football team. But I've always had this like two sides of the brain. Like I love playing the piano. And when I started my career at Goldman, I was definitely the behind the spreadsheet with your headphones on late into the night analyst. Like I was actually the semiconductor analyst on our team.

Speaker B: Oh wow. Speaker A: The TMT team back in the day, which was, very out of fashion for a long period of time. I wish I actually like studied harder back then because, you know, that would have been good to know the last few years. When I got to Sequoia, similarly, I was, you know, very quantitatively bent for probably the first like 4 or 5 years of my career. And I think one thing you learn with startups is your spreadsheet is always so wrong. You know, it's usually wrong in the bad direction.

And when you're lucky, it's wrong in the, you know, good direction. and the biggest difference between when it's wrong and the bad direction and the good direction is the person running the company and the team that they build. So I think naturally, you know, you learn that, you know, it really is all about the people. And obviously, like, parallel to your work life is your personal life. And, you know, changed a lot from high school to college to San Francisco to kind of being an adult and kind of growing up around a lot of people here in San Francisco.

So to introduce, like, new interests and new concepts. And that's reflected both in terms of the things I've done in investing and also just how I spend my time. Speaker B: Maybe a sort of orthogonal, but I think also kind of a double-click on this, which is another element of that, is that a lot of parts of you are like kind of like in central casting for what you're like a good-looking white dude who works in venture capital and worked at Goldman. Again, kind of same theme. Football player, and I talked to multiple people who know you.

One thing our mutual friend and former colleague Matt Huang said is like, he's like the football player who's also like a hardcore Redditor. And there's like a— there's clearly a good amount of weird. And so I'm curious how that— and my sense is, is that's part of what makes you— you're not a pure finance guy. And that's part of what makes you a great venture capitalist is like your nose for the slightly strange. Or the contrarian. And so I'm curious too, how, how you think you've maybe to the extent you've gotten weirder or how you've fed that.

Speaker A: I think going back to my childhood, there's this like major— like my main trauma in life was I grew up with a very bad stutter. And actually, when I first interviewed with Doug Leone, I gave my resume and he looked at it for you know, 20 seconds and he goes, oh, you got, you went to Amherst, you got this GPA, you played sports, like, we're at Goldman Sachs, there are, you know, 200 people just like you I could hire. Why would we go hire you? And in a very kind of like antagonistic Doug Leone interview way.

And I think like the two things that like really motivated me, like first is, you know, obviously having a twin brother and we've competed our whole lives and there's definitely hardened some competitive drive in me. And I spent basically like my entire childhood just observing, you know, like it's very hard to jump into conversations and do public speaking and raise your hand in class even. Like I just spent a really long period of my life just listening and it's definitely gave me like a lot of empathy with, for the outsiders.

Yes. Speaker B: Yeah, yeah. Speaker A: And people who are in low moments and also people who just don't feel like they fit in totally. And then amazingly, like in college, I did speech therapy from when I was a kid up through when I graduated from high school. And that same summer I went to college and I stopped doing speech therapy and, you know, like got laid. And then all of a sudden everything fixed itself. And like within 6 months I didn't stutter anymore. And now, you know, I do host the LP meeting and I go on TV and do these things and like no one sees that side of me because it's literally like hard to, you know, it's like hard to find.

But I think that that element of just like weird really does come from that, you know, like the personal feeling of just sort of, I think, like watching things. And I think when you talk with people who are building companies, a lot of the founders like who I work with are like, you know, maybe now successful and famous and everything else, but like deep inside them is like the same thing that was deep inside me. And, you know, people who meet them for the first time today, like, don't see it.

But I feel like I have a kind of unique way of, like, seeing the little kid inside people sometimes. And I think that helps with just, like, trust, you know? Speaker B: Yeah. Yeah. It's interesting how— and I'm sure it's different for everybody, but, like, becoming the version of yourself you want to be, it doesn't sound like that happened through, like, a lot of striving. Or at the very least, the striving and the the speech therapy or whatever, like a ton of effort towards that doesn't necessarily— Speaker A: Yeah, well, another thing, just in terms of the striving, like you mentioned Matt Huang, I feel like at so many points in my career, I've just gotten extraordinarily lucky being surrounded by people who are so good.

Like my— the person introduced me to Pat Grady was my first introduction to Sequoia with Sarah Guo, who was in my class at Goldman. Sarah and Pat are now married, and Sarah's obviously like an extraordinary talent who's— has been and will continue to dominate her corner of Silicon Valley. And then I started as a class of 2 associates at Sequoia. It was me and Matt Huang. And could you imagine like a more talented counterpart to be pushing you every day? Speaker B: Also like very much a startup guy at the time.

Yeah. Like you were not a startup guy. Speaker A: No, no. And that's— that was the Like, I think the associate class of me and Matt Huang, I hope, is going to go down in history as the greatest bang for your buck associate class ever hired. But we started on the same day, February 18th, 2014. And I remember meeting Matt for the first time and, you know, he was, you know, on the growth team at Sequoia. And we do a lot of spreadsheet math and cohorts and things like that. And I had never done an in-person meeting in my life with a founder, or like, I'd never— didn't really have like a network in Silicon Valley.

And we like really leaned on each other for a period of years, you know, in a way that was extraordinarily collaborative. And to this day, like, there are a small number of people who I genuinely feel like are superior investors than me. And like, Matt's one of them. I think Pat Brady's one of them. And like, Pat was my direct manager, you know, for my— all my one-on-ones when I joined Sequoia. Matt was the person who sat next to me for 5 years. Kevin Kelly at Sequoia Heritage, who joined I think 6 months after that on the Heritage side, same age, like also just an exceptional investor.

And then obviously being surrounded by my, my initial desk at Sequoia was actually on the same open floor plan, like on the same desk as Doug Leone. It's almost like, you know, you could have put an idiot in that situation and they would have found a way to at least make some good investments. Speaker B: Well, you could take it the other way. You could say, take it as like, wildly, they threw you to the shark. Speaker A: Yeah. Speaker B: Like, it was both. Speaker A: Yeah, no, I think there's a way in which, um, I think this is kind of how we think about like developing younger investors at Sequoia too.

Uh, I think what we lack in like structured feedback process, et cetera, which we lack a lot, we more than make up for in the culture of like really investing in each other and kind of especially in the next generation. I think some people really like that environment, you know, the sort of having lots of freedom to, you know, it's like sink or swim. But even if you end up swimming, you're like, feel like you're sinking for a long time, you know, you're like struggling to stay on top of the water.

Speaker B: Well, I think you said somewhere like your second day, they— WhatsApp was acquired or something. Speaker A: Yeah, I was in there also. And you should check the dates. I think it was February 19th then, or maybe it was February 20th, but it was February 2014. Was when the WhatsApp-Facebook deal was announced, and that was like a $4 billion-ish gain for Sequoia. Speaker B: That's the bar. Speaker A: Yeah. Speaker B: Welcome to the company. Speaker A: Yeah. And it was, you know, obviously that was amazing. And then literally there was a, you know, email that goes out saying, you know, meet in the— we were in this dingy office.

We were [redacted address], second floor, Building 4, Suite 250. It was like Sequoia's longtime office. Be in the lobby, uh, at noon for like a champagne toast. It's like, oh, champagne toast. It was literally 5 minutes long. And then everyone goes back to their desk and just keeps working. And, uh, that was an interesting moment. Like, I don't know what to take from it besides like Jim Goetz is a legend. And also that like, yeah, greatness is sort of expected, you know, and that definitely still feels like this case. Speaker B: Maybe a lead into the last thing I had pulled out before we talk specifically about investing, which is competition.

Obviously it sounds like it starts with Will, your twin brother. So a lot of competition growing up. I think what I'm interested in, and maybe it goes back to what you're saying about Matt and Pat and maybe Sequoia's culture broadly, is like there is this deep competitiveness that I sense you have. You clearly, you, I don't know how much you like to win, but you do a lot of winning. And I think competitiveness can be channeled in really great ways or really unhealthy ways. And so I was curious for how you relate to that aspect of it, like what that source of energy— like, is it— to what extent it can be good fuel or bad fuel?

And then maybe beyond that, how competitiveness can still sit right next to like positive sum outcomes,, you're sort of competitive with Matt and also collaborative, or vice versa, or with Will, who does a very similar job at a different firm? Speaker A: Yeah. Yeah. I try my best to exude California cool. I think for anybody who's ever been in a trivia competition with me or any sort of a board game or chess or anything else, like, I hate losing. I think my brother actually hates losing worse than I do.

Or maybe we hate losing the same, but I've somehow gotten to a point where I can at least pretend like I can deal with it, you know, where he's still at a point where he definitely can't pretend. And I think what's interesting, like, I think there was a period of my life when I definitely felt maybe it was an insecurity or otherwise around like when people did well and I wasn't doing so well, I felt jealous or, you know, sort of like the anxiety that brings. But I think, I think Matt's like a really good example of this where like he is, or like Dylan Field at Figma, similarly, some of these people I met like really early in my life who have gone on to just do incredible things.

Number one, like you knew the entire time that they were incredible people, you know, and number two, they are the same level of like good and exceptional and kind and caring and looking after you now as they were when you were, you were nobodies, you know, and I think in the Valley, obviously, Number one, like, great people can win and like watching great people win is actually rewarding in its own way, you know. Number two, it's decidedly not zero-sum, right? Like, I think one of the, one of the funny moments is like when you make an amazing investment gain on a company, it's a growth investor.

More often than not, there's some Series A investors making more, right? So it's like you kind of have to accept that the, you know, like the, the job you've done well is worthy, you know, and it doesn't have to be the most money. Yes. Speaker B: Or even multiple too. You might be making more money, but their multiple is better. Speaker A: Yeah, but it's like, you know, like we have a job and our job is, you know, at some level it's like the fund management business. And if our funds are doing well, then we're, you know, we're doing well.

And, and similarly, like, we're not going to be perfect. And we— nobody is more into self-flagellation than Sequoia Capital. Like our offsites are just like a death march through the sins of the past. And there's good learning in that, you know, But you— I think the right frame of mind is like you need to accept that you're going to make some mistakes and try to get better. If you end up dwelling on your mistakes as an investor, especially in venture where the world's moving so quickly and it's always about the next rock you're turning over, you can end up totally stuck.

Speaker B: Let's talk a little bit about investing. I think I'm most interested to start with— there are lots of ways to be a good investor. I think that's probably what drives— draws so many really smart people to it. Maybe there aren't lots of ways to be a truly great investor, but there are lots of ways to be a good investor. I'm curious how you would describe your style, like how you invest and why you think you're good at it. Speaker A: I think it starts from a place of like genuine curiosity and excitement about companies.

I think I, at my heart, I'm a finance person. I love companies. Like we used to do this thing where we would throw up the numbers of a company on the whiteboard on a Monday morning and you had to guess which company it was. And that was one of those trivia games that I love dominating. And like this, the world is full of these like wonderfully interesting businesses and uncovering some new, some new theme or some new founder or some new business that you haven't heard of. And it like completes some mosaic that's just some corner of the broader mosaic of how the world actually works.

Like, that's such a compelling feeling. And I think I'm consistently still like uncovering new things. And then obviously the world's changing so quickly. New things are constantly like cracks in that mosaic are opening and then being formed by and being filled by something else. Speaker B: Yeah. Speaker A: So it's definitely for me comes from like initial place of this curiosity about business. And then I think like just by nature of where I am in Silicon Valley doing, you know, private company equity investing, like you end up trying to find like what are the most interesting companies?

And those are often led by the best founders. And then when you're actually doing your risk-reward analysis, like it comes down to the best people matter the most. And I think there's one thing I've done really well is I think, I think because I joined Sequoia so young, I was 23 when I started and I didn't think, you know, the first investment that I put my, you know, I was neck on the line for like the first investment I sponsored was in Robinhood. That was, I think, 4 years after I joined.

So I did 4 years in the salt mines, you know, like just similarly, you know, just observing, right? I was doing all the memos, you know, doing all the models, crunching a lot of the numbers, crunching a lot of numbers. And, you know, I would like have opinions, but like I wasn't ultimately the one who was responsible for that investment, you know, filling out the portfolio review software form and, you know, giving the update. Speaker B: Yes. Speaker A: And then, you know, with like, I think Robinhood was obviously an instructive and amazing and crazy experience in a bunch of different ways.

But I think it's really important and really lucky to get like a, you know, a banger out the gate as an investor because then all of a sudden your, your model is trained on like what great looks like. Speaker B: Really positive feedback loop. Speaker A: Yeah. And it's, you know, both in terms of like your own learning and from your reputation and otherwise. And I think with that experience working with Vlad and now I'm working with Vlad again on Harmonic, his, his second company. Speaker B: Really positive feedback loop.

Speaker A: Yeah. And it's, you know, both in terms of like your own learning and from your reputation and otherwise. And I think with that experience working with Vlad and now I'm working with Vlad again on Harmonic, his, his second company. Speaker B: It's like the AI math company. Speaker A: Yeah, the AI math company. We— I just like, oh my goodness, like I can like find these, like, you know, and identify these like really outlier people and they're not all going to work. But like, I think starting with Vlad and then, you know, going through to like Vlad and Tudor round 2, like I think I've just picked the best set of founders.

Like I would not, you know, trade my team competing against the Space Jam aliens, you know, for anybody, like for literally anybody. I think I have the best that there is. And And then once you get used to that, you know, your bar just gets raised so high, like you just— I don't know, it's just— I think it's just like keeps you focused on the main thing, which is identifying amazing people. And then obviously having a team like that working on your behalf is really helpful too. Speaker B: Was there opposition to the Robinhood investment?

Was it like a fairly consensus type thing amongst your partners or peers, or was it were you kind of pounding the table? Speaker A: It was ultimately consensus, obviously, like contentious. It's a very, you know, divisive company and still is to this day. You know, like Charlie Munger went to his grave, you know, railing against Robinhood. He actually had this and obviously, you know, bless his soul and rest in peace. And Charlie Munger, like, we love Charlie Munger. Yeah, he did an interview where he said, you know, Sequoia is the best investment firm in the world, but I can't believe they invested in Robinhood.

The company's evil. And imagine being like an associate at Sequoia and trying to read, you know, it's like your only company and Charlie Munger is, you know, going on the record just railing against it. That's not the most comfortable place to exist, you know. But it's actually amazing if you look at just the— we can get like Robinhood for much, much, much longer. Obviously, that was like the— probably the one of the few formative investment experiences in my life. And just the roller coaster, it continues to this day. But the— yeah, the initial like entry into the investment was not super comfortable and it didn't stay comfortable for very long.

Speaker B: Did you you have this model of Vlad today, and let's say that's like whatever, 99% knowledge or conviction of his greatness or whatever. Like, was that a critical part of your initial conviction or did that come later? Was it— was your conviction in something else about the business? Speaker A: Well, first I would just like— I'll often just like mention Vlad as like shorthand for Vlad and Beiju, his co-founder, like I'll do that with Figma. Dylan is— Dylan and Evan is co-founder, right? Like you sort of often shorthand to the, you know, guy who's running it now.

But so much of the DNA of like these companies comes from like the full set of not just co-founders but early employees, but like co-founders are so central. I think that I was actually thinking about this this morning. I think the degree to which like the best founders change and grow over the course of their company's life is extraordinary. Like Vlad today versus Vlad 10 years ago is borderline unrecognizable. And it was both the successes and failures of Robinhood that sort of like made him change so much. And it's not obvious to me whether it's, you know, the companies that grow so much, like, force change upon the person running them, or if it's the fact that the founder is changing so much that creates the you know, the success of the company.

But I think there's this one common trait around like a genuine growth mindset. And I think like it's the, I am capable of learning anything. And when the job requires me to go learn that thing, I'll just go do it. I think, you know, Vlad back in 2016 was like, you know, they did such a good job hiring engineers out of Stanford and building incredibly compelling products across like onboarding into a fintech app across the infrastructure. You know, they built the first self-clearing system built in America, I think, in 30 years.

Took over a year to develop. Like it was, you know, one of these like really hardcore finance infrastructure projects and like Vlad spearheaded a lot of that. And then Beiju was a lot of the creative energy, some of the kind of countercultural elements that like made Robinhood so unique and special. And they both did, you know, both of that. But the Vlad now of like standing on stage and like being like a true spokesperson for an industry and a movement, that is not the person he was then, and I think now, like, he's so capable and mature and he still has, like, he can still recruit amazing engineers.

Like, the people that Harmonic hires blow me away. But also he can, you know, stand at Cannes in front of the ocean with his amazing outfit and, you know, like, yeah, like speak to a whole, speak to the whole world. So. Speaker B: I guess I have two questions off that, which is, I still wonder, like, Did you ultimately, was there a seed that you saw or were you like excited about Robinhood for some other reason and like got to— Speaker A: Oh yeah, I forgot to answer the question you asked.

Um, like one of the things that, one of my things I used to say, I feel like you kind of go through these things where you learn something and you say it a zillion times to different people when you have some insight and then after 6 months you get tired of saying it. So you move on to the next thing. Um, like one of the things that I was saying a lot back then was like, you can't find the companies with the 90th percent metrics across every dimension because the 90th percent startup doesn't go anywhere.

You know, you have to find companies where there are just some outlier dimension. And I think for Robinhood, the thing I saw back then, like I wasn't the first to it. Was, you know, they were just uncannily great at dominating the, the like front end of that business, which was, you know, their share of new account openings in the US, even when they were small and irrelevant, was north of 60%. Like they were— Wow. Speaker B: Also some crazy waitlist. Speaker A: Yeah. Out the gate they jump with a big waitlist, but also just like reliably, even when like the industry was slow and the equity markets were, boring for people, like they were still just the vast majority of new account openings in the US and they were doing it without blasting the world with, you know, E-Trade advertisements and everything else.

It was just like, it is such a superior product. Back then in 2014, the idea of, you know, this is back when you used to like log into your desktop to do serious banking tasks, you know, like even the fact that people would be holding like big balances on their mobile phones was a little bit outlandish. And then they just like continuously, like, just kept people engaged. And that was the thing that like, I really, really stuck with me was the first was this, the, um, and it wasn't a lot of fintech apps aim for the underbanked and try to provide financial services that are available to one class of people, to other people who are less well-served.

What Robinhood did was just like, they found this like big profit area for incumbents, which was commissions. And they said this doesn't need to exist, right? Like if you don't have branches and you have like a, like genuinely low-cost operations, you could just like remove commissions and you can make enough money through paying for order flow and stock lending, other mechanisms that you can just, you know, grow a business here. Speaker B: Also some crazy waitlist. Speaker A: Yeah. Out the gate they jump with a big waitlist, but also just like reliably, even when like the industry was slow and the equity markets were, boring for people, like they were still just the vast majority of new account openings in the US and they were doing it without blasting the world with, you know, E-Trade advertisements and everything else.

It was just like, it is such a superior product. Back then in 2014, the idea of, you know, this is back when you used to like log into your desktop to do serious banking tasks, you know, like even the fact that people would be holding like big balances on their mobile phones was a little bit outlandish. And then they just like continuously, like, just kept people engaged. And that was the thing that like, I really, really stuck with me was the first was this, the, um, and it wasn't a lot of fintech apps aim for the underbanked and try to provide financial services that are available to one class of people, to other people who are less well-served.

What Robinhood did was just like, they found this like big profit area for incumbents, which was commissions. And they said this doesn't need to exist, right? Like if you don't have branches and you have like a, like genuinely low-cost operations, you could just like remove commissions and you can make enough money through paying for order flow and stock lending, other mechanisms that you can just, you know, grow a business here. Speaker B: By the way, then you throw everybody into a crazy innovator dilemma. Speaker A: Exactly. And the things that, you know, people— Robinhouse— oh yeah, but they're just like, they're doing, you know, payment for order flow and not commissions.

And like, people fail to realize that, you know, what E-Trade was doing? Both. You know, it's like, you know, it was strictly better for people. Besides Fidelity, everybody else was doing both and they just wiped that category out. And yeah, from, you know, companies founded, I think in 2013, September 2018, September 2019, was when Schwab, E-Trade, and Fidelity all waived commissions to zero on the same day. And, you know, it's like the George Bush, like, mission accomplished banner, right? Like, literally the point of, like, the initial, like, one of the initial impetus of the company was just like democratize finance for all.

And the first mission was to, you know, eliminate commissions. And within 5 years, literally, that's no longer a thing that exists. Crazy, you know? And that was in some ways just the beginning, you know? Speaker B: By the way, then you throw everybody into a crazy innovator dilemma. Speaker A: Exactly. And the things that, you know, people— Robinhouse— oh yeah, but they're just like, they're doing, you know, payment for order flow and not commissions. And like, people fail to realize that, you know, what E-Trade was doing? Both. You know, it's like, you know, it was strictly better for people.

Besides Fidelity, everybody else was doing both and they just wiped that category out. And yeah, from, you know, companies founded, I think in 2013, September 2018, September 2019, was when Schwab, E-Trade, and Fidelity all waived commissions to zero on the same day. And, you know, it's like the George Bush, like, mission accomplished banner, right? Like, literally the point of, like, the initial, like, one of the initial impetus of the company was just like democratize finance for all. And the first mission was to, you know, eliminate commissions. And within 5 years, literally, that's no longer a thing that exists.

Crazy, you know? And that was in some ways just the beginning, you know? Speaker B: When it comes to seeing sort of like the Vlads of tomorrow, Like, how has— again, maybe to go back to like, if you, if you have him modeled like 90% or 95% or 99%, when you meet somebody today and maybe there's also something that's pulling you in,, the approach to the product or the technical competence or whatever, like, but you're modeling them at 10% or 20%, like, how have you thought about being able to see the seed that is going to grow into that kind of exceptionalism?

And clearly you've been able to do it. Across lots of people, given your Space Jam comment? Speaker A: Yeah, there's like, I think there's sort of two, there's like two ways that I can, I can develop conviction on a person. I think sometimes you are lucky to have met somebody for months to years before there's an investment opportunity and you like watch them develop and execute and run their company. So, you know, I think with Dylan from Figma is a good example. Like, uh, I met Dylan you know, riding shotgun to one of our early-stage partners for one of the early-stage rounds of Figma and like saw what the company was then.

And Soleo Cuervo, who was, uh, one of the early Facebook product designers and, uh, like a highly relevant figure at Dropbox and otherwise was also in my ear about Dylan. I, you know, I followed the company and it was $500K of revenue and most of whom were on Windows machines and Sketch was only on Macs and it was hard to see. And that was the round that Mamoun from Kleiner did, which is absolutely one of Mamoon's many iconic investments. And, you know, I kept following the space. And then when it came time for like the Series C, which is one that we did, the company had grown from $500K to $4 million of revenue, which, you know, on paper feels like it's still a very small company.

But I could not have been more sure about Dylan, you know. Speaker A: Yeah, there's like, I think there's sort of two, there's like two ways that I can, I can develop conviction on a person. I think sometimes you are lucky to have met somebody for months to years before there's an investment opportunity and you like watch them develop and execute and run their company. So, you know, I think with Dylan from Figma is a good example. Like, uh, I met Dylan you know, riding shotgun to one of our early-stage partners for one of the early-stage rounds of Figma and like saw what the company was then.

And Soleo Cuervo, who was, uh, one of the early Facebook product designers and, uh, like a highly relevant figure at Dropbox and otherwise was also in my ear about Dylan. I, you know, I followed the company and it was $500K of revenue and most of whom were on Windows machines and Sketch was only on Macs and it was hard to see. And that was the round that Mamoun from Kleiner did, which is absolutely one of Mamoon's many iconic investments. And, you know, I kept following the space. And then when it came time for like the Series C, which is one that we did, the company had grown from $500K to $4 million of revenue, which, you know, on paper feels like it's still a very small company.

But I could not have been more sure about Dylan, you know. Speaker B: You also paid it, if I remember correctly, a pretty obscene price. Speaker A: We paid $400K. Yeah. Which was— yeah, that was viewed as ludicrous, you know, unhinged. And obviously, you know, like Dylan's only continued to develop. So that's one, you know, I'm going to put similarly the most recent board I've joined is ElevenLabs, the AI audio company. And same sort of dynamic, like we invested in ElevenLabs 2 years ago. I didn't join the board, but just like watch Mati, who's the founder there, as a like young Polish kid living in London, building a company at the absolute, like, most competitive bleeding-edge foundation model, creative tools, AI agents, like, on paper, that guy is never going to win that race, you know?

Speaker B: You also paid it, if I remember correctly, a pretty obscene price. Speaker A: We paid $400K. Yeah. Which was— yeah, that was viewed as ludicrous, you know, unhinged. And obviously, you know, like Dylan's only continued to develop. So that's one, you know, I'm going to put similarly the most recent board I've joined is ElevenLabs, the AI audio company. And same sort of dynamic, like we invested in ElevenLabs 2 years ago. I didn't join the board, but just like watch Mati, who's the founder there, as a like young Polish kid living in London, building a company at the absolute, like, most competitive bleeding-edge foundation model, creative tools, AI agents, like, on paper, that guy is never going to win that race, you know?

Speaker B: Right. Speaker A: And then all of a sudden you just like watch him, you know, month to month and quarter to quarter, just like grow and develop and change. The company just becomes this like winning machine. And, you know, so the question was like, you know, would you do the ElevenLabs board? Like, would I want Motti on my, you know, Space Jam team? Like, absolutely, like 100%, you know, and that's like a very comfortable way of, I think, like developing conviction on somebody. Well, when you get down to like the rubber meets the road, should I pay this price?

The answer is like an unequivocal yes in your gut. I think there's like a smaller category of investments that I've done where it's like you're just shotgun wedding. Like, is this person that good? You know, probably my favorite example is Cristiana Casiapo, who runs Vanta. Which is, you know, now a like very large and very dominant security company here in SF. And this was in 2021, like Jan 2021. And, you know, rounds happened in like 16 seconds. And I got introduced to Christina from— by Dylan, actually. And I checked our like notes in SMS, which is SMS is our, our internal data science CRM type product.

And, you know, like Sean McGuire had been tracking the company for a long time. He was like, this is like the company I would invest in if I had the chance to. And then like Dylan was like, you got to do this investment. And then like Patrick Carlson called me, he's like, you should probably do this investment. I met Christina and within about 14 seconds I decided that I should do this investment, you know, and— 14 seconds on the phone with her. Yeah, it was like instant. And then actually We had Christina talk at our LP meeting 2 years ago, and her memory of our first meeting was like I was rushing her through her pitch deck.

But the reason I was rushing her is like, I was like, I know, I know it's good, you know, just like, let's get to the part where we like try to figure out, you know, what the terms are, you know. It's funny. And she never told me that, but she told all of our LPs. And for that, it's like really like this, you know, sparks fly sort of moment, you know, where and it helps when the company's growing really fast and profitable. Speaker B: Right. Like, I guess that's my, my, my thing I'm wondering is like, well, one, one backdrop for all this that's interesting is typically early stage investors love to talk about people and later stage or growth investors love to talk about other things, other types of momentum.

And so I guess like how much of this is all this people stuff you're saying with the backdrop that also the thing is starting to rip? Speaker A: Yeah. Speaker B: Like maybe that's the given. Speaker A: Yeah, I think if you divide the world into like founders who are obviously amazing to you, which is a taste thing, and then numbers that are obviously amazing to you, which is also a little bit of a taste thing, right? Like different investors certainly weight different metrics and, you know, different dimensions. And I'm probably more comfortable with like some metric screaming red if enough other ones are screaming bright green.

Speaker B: Okay. Speaker A: But if you divide the world into, you know, amazing founder to you and amazing numbers to you and like don't deviate from that, You'll maybe find 3 companies a year that meet your bar, you know? And then of those, like, one will be priced so ridiculously you're not going to do it, and the other 2 you do. And that's basically like what I've done for the last 10 years. Speaker B: If you could, to keep doing your job, you either had to— well, actually, I'll split it up.

Um, if you, if you had to do your job without ever meeting a founder ever again, how would it affect your returns? And then if you had to do your job without maybe this is stupid, but like ever using Excel ever again, how do you think it would affect your returns? Speaker A: Well, there's a great— I will keep talking about Charlie Munger despite his criticisms of me because he's obviously, you know, the GOAT. There's a great back and forth between Warren Buffett and Charlie Munger where, you know, Warren Buffett's talking about how if you like, you know, are doing a DCF on a company and it says— and Munger interrupts him and it's like, you know, you've never done a DCF.

And he's like, No, if you have to, if you have to actually do the math, it's, it's, it's too, it's too close. Like if it's, you know, it's like you just do a quick DCF in your head and if the company is good enough, like the math takes care of itself. And if you have to resort to doing data analysis, like you're in trouble, you know, and I think that's probably true. Like I think there's like the occasional corner case where you have to do some sophisticated analysis around cohorts, around usage.

To get to like the ground truth of a company. But more often than not, like the output metrics sort of take care of themselves, you know, and it's like almost like don't get cute. Yeah. And yeah, exactly. And then even if there are situations where you have a company that's growing really fast and the issue is like what's the churn, you know, like you can get to that pretty quickly. Yeah. I think the no founder thing would be impossible. Like I like wouldn't even know. I just buy an index, you know.

Speaker A: Well, there's a great— I will keep talking about Charlie Munger despite his criticisms of me because he's obviously, you know, the GOAT. There's a great back and forth between Warren Buffett and Charlie Munger where, you know, Warren Buffett's talking about how if you like, you know, are doing a DCF on a company and it says— and Munger interrupts him and it's like, you know, you've never done a DCF. And he's like, No, if you have to, if you have to actually do the math, it's, it's, it's too, it's too close.

Like if it's, you know, it's like you just do a quick DCF in your head and if the company is good enough, like the math takes care of itself. And if you have to resort to doing data analysis, like you're in trouble, you know, and I think that's probably true. Like I think there's like the occasional corner case where you have to do some sophisticated analysis around cohorts, around usage. To get to like the ground truth of a company. But more often than not, like the output metrics sort of take care of themselves, you know, and it's like almost like don't get cute.

Yeah. And yeah, exactly. And then even if there are situations where you have a company that's growing really fast and the issue is like what's the churn, you know, like you can get to that pretty quickly. Yeah. I think the no founder thing would be impossible. Like I like wouldn't even know. I just buy an index, you know. Speaker B: Maybe that's the fundamental difference between the work you do and other parts of finance or private equity or whatever. Speaker A: Yeah. Speaker B: Or even public equities. Speaker A: Yeah.

Speaker B: I found this actually, a friend sent me this hilarious thing. Green Oaks has quite literally trademarked jaw-dropping customer experience. Speaker A: Yeah. Speaker B: Or even public equities. Speaker A: Yeah. Speaker B: I found this actually, a friend sent me this hilarious thing. Green Oaks has quite literally trademarked jaw-dropping customer experience. Speaker A: Yeah. Speaker B: And quote, breaking tradeoffs. And so I'm curious if there's anything that you would trade off or trade off trademark. In terms of like the style or the things you're looking for, or the, the maybe a lighter version of it is just like what's on the Andrew Reid Sequoia vision board.

Speaker A: Yeah. You know, I don't think I'm innovating on any dimension. Like the— and what's interesting about, you know, working with someone like Pat and I was talking about Pat for a minute because, you know, he is like definitely the most influential person on my career. And Pat and I, you know, co-led the growth business at Sequoia together for a number of years. And, you know, I've been his, his associate. I've been his partner. You know, it's like he and I disagree about investments so often. And it's the specific thing that often happens is Pat brings in a company and, you know, my humanities taste element, you know, just isn't clicking for some reason.

And the thing that Pat hates— Pat hates when he feels like people, because of his track record, aren't telling him the truth. So I always try to tell Pat my absolute truth on the companies he brings in, which sometimes is like, dog, what are you doing? You know? And the reason why Pat's like that is he's got this, you know, whereas I don't have anything I would trademark in terms of, you know, frameworks otherwise. I feel like you could, you know, freeze Pat's brain and like chip off a little corner and it's got some framework that he hasn't even told you about that, you know, unless you ask him, you know, it's like the whole thing is this Rube Goldberg machine of, you know, like frameworks and processes.

And I think if you are, you know, if you're 90th percentile frameworky, you're not going to be a great investor. If you are 100th percentile frameworky, you can actually be extraordinarily creative because a lot of people are just doing shorthand on things and just miss like incredibly obvious opportunities. Probably my two favorite examples. One is our investment in Open Evidence, which is the, you know, leading AI app for healthcare professionals. And this was a company that had no revenue. It was, you know, selling a free AI service only for licensed medical professionals that looked a lot like ChatGPT, but it was up to date with the most current medical literature.

And, you know, it comes in. The founder had a really good reputation. He started a company called Kensho, which he sold for, I think, $700 million. But he was living in Malibu and the team was working out of his house in Malibu and had like 10 people and no revenue. And, you know, a few of us have like doctors as relatives and none of them ever heard of this thing. and literally Pat was like, you know, I think we should do this investment. You know, it's like, why? You know, it's like it was just, it seemed so, and you know, they had raised no venture capital and they were going to raise $100 million and, and it's just like, I don't even know where to begin on criticizing this idea, you know, like, like maybe I'll start with no revenue just to get, just to get the conversation going.

And it's like point by point by point. Pat just like explained exactly what he saw. And I think they just raised it like $12 billion and it's backed by just like incredible, incredible— Speaker B: in this sort of frameworky, systemy type. Speaker A: Yeah, it's like just systematically like piecing apart your argument, you know, and just like, you know, like, oh, like, yeah, I guess, like, you know, they got to the point where at the end of the process, like, we were all really enthusiastic about investing. You know, Pat's got a strange brain, so he really wanted to win this investment.

And, you know, we get to give— we issue the term sheet and Pat's working late at night and he's the kind of guy like he won't ask the finance team to do a term sheet late at night if, you know, he can just do it himself on his computer. But he really wanted to get it signed because he wanted to, you know, get it over with and move on. So Pat logs into like the DocuSign portal and like creates the DocuSign for this term sheet, which he had never done before, and I also have never done before.

And he sends it to the founder, and then like, you know, they go back and forth, and the founder loops in the lawyers, and Pat's like, when's this guy gonna sign a term sheet, you know? And then the founder invites them on this company offsite in Bora Bora or something, you know? And Pat, he's like, okay, yeah, of course, like, I'll be there, you know, I'll be there tomorrow. Right? Like, you know, he comes with like the, you know, the only goal is I can't like leave the office to go to Bora Bora and come back with that term sheet signed.

So he, you know, spends the whole 2-day offsite like talking to 11 employees at this company, you know, like really trying to find the right moment to like get this thing signed. And then he realized that when you are the one who puts in the DocuSign, you don't actually get the email back that says the guy signed it. The guy signed it immediately. And Pat spent like 10 days of his life so stressed out, literally flying to Bora Bora, stressed about getting this term sheet signed. Speaker B: It's like we're already working.

Speaker A: Yeah, yeah, yeah, yeah. Speaker B: Anyway, that's Pat, you know, maybe, maybe I guess to come back to you, like the— this business is one of sort of continually finding exceptions and yet Sequoia and seemingly you have done quite a good job of doing it over and over and over again. And so like if, if Pat is on this like highly 100% framework, like highly structured way of doing things. Like, do you feel like you're pulling a continually, like pulling rabbits out of hats? Like there are some, and clearly you've developed an instinct on the people side and you have, maybe this gets into taste in even numbers, which I'd like to talk about, but I'm curious, like what is this tension between consistency and exceptions?

Speaker A: Well, I think like one of the ways, you know, I think one of the ways you learn how to do this job, maybe the only way, is to watch the people you, you know, work with do the job and figure out your own way from there. And I think one of the things that Jim Goetz used to always talk about is people who can repot themselves as investors. You know, Jim, you know, helped put together the seed of Palo Alto Networks with Hashim from Greylock, you know, and is one of like the leading cybersecurity investors.

Like early-stage cybersecurity investors. And then he turns around and does like this kind of growthy round in WhatsApp, you know, and, and I think that, or like Mike Moritz, you know, who obviously did Yahoo and Google and then PayPal and then lost money on Webvan, then turned around and Instacart and did Stripe, you know, it's like, or Doug Leone, who's like the most famous enterprise investor of his generation at the tail end of his career, just kicks in the Nubank seed and Series A and, you know, biggest return of his career and one of the biggest ever in venture.

Like there's this kind of this like this track, you know, the track of people who just don't get bogged down by like, I am a SaaS investor, you know, or like I'm a Series B investor, right? It's people who are like consistently willing to like reinvent themselves and take the risks on their reputation or their, you know, knowledge, understanding, etc. I think that's like one of the key lessons from Sequoia is it's like you just can't keep doing things the same way. And that applies at the system level, right? Like, you know, what businesses are we in, how we set up our teams and everything.

And at the individual level, like we don't have swim lanes in the same way some people do, you know, like imagine, let's just say like every investor does 2 or 3 deals a year. Imagine entering 2021 or entering 2022 and you have like of your 10-person investment team, 2 people on AI, right? That means maximum you have 6, 6 AI investments, right? And people aren't perfect, you know what I mean? Like that would be crazy, right? So you kind of want to have like you'd rather have like a team of curious people who— it's a little bit—

Speaker B: I mean, I'm sure you'll back down from the comparison, but it's kind of how you were describing Vlad, which is this just like default. I can, I can figure it out. I can figure it out. Speaker A: Yeah. I've always— I mean, to me it's like if hedge funds can have TMT analysts, why can't we have TMT analysts? I can be a TMT analyst, right? Like it's— and obviously there's some people who bring like really specific domain expertise. Like I was lucky enough to, you know, wingman Sean Maguire on our SpaceX investment.

You know, like Sean's got big ideas and, you know, he's very vocal about sharing them. And when we went to SpaceX, Sean was like a quantum physicist and like worked with rocket companies and, you know, in his past life, we're like walking through this factory floor where they're, you know, making spaceships. And he just like notices that, you know, one of the— I don't know how to describe this thing. I'm like, one of the things that moves the satellite in space, they're using some gas that you wouldn't have assumed that they were going to use because of like the label on this tank.

And then he asked the question to the guy and the guy explains why they— oh, that's, you know, why we use this gas and not that gas. And I was like, I don't even— I didn't even realize that was the satellite yet. You know, it's like I'm not even zip code, right? You know, so, there is this dimension of like you do want people who have like, you know, if you like complement that with people who have real domain expertise and can like really uplevel your thinking, that's how I think you get like really exceptional investments.

But all of us are like always trying to learn, you know, and trying to just try new things. Speaker B: I think there is an underrated lesson amongst great investors, which is that they are— maybe this is much more obvious in your— in the growth side of things, but like they are not only right, they're right with with size and with extreme conviction. Maybe to start, like, what is different for you between investing, at least maybe not for Sequoia's first investment, for your first involvement in a company versus doubling down?

Speaker A: I think in general, like Sequoia has invested over $1 billion at cost into, I think, 3 companies now. And in general, the way we've gotten there is starting very, very small. You know, and doubling down and tripling down. And like Stripe's a great example. You know, we first invested in 2010 and our first investment was like $1 million or something like that. You know, I think the biggest source of unfair advantage in evaluating investment opportunity is being on the inside, both in terms of like obviously being in the board and seeing the pipeline and seeing how things are developing and watching the founder execute.

Speaker B: All the people stuff you were talking about, Vlad, you're not going to get that lens from— Speaker A: And it's not— it's funny, it's actually not universally— I think the hardest round is the next round after you invest. I think it's like, it's actually quite straightforward to do, you know, make the investment and then 7 years later when you have like extraordinary conviction and the company's, you know, marked up 8 times from when you invested, but they've grown the business, you know, 30-fold or something like make that investment, you know, the hardest one is, you know, you invest, 6 months later there's a term sheet in at 5 times the price you just invested in.

Speaker B: Very little, much, like not more data. Speaker A: Yeah. Like the data is, in fact, you just joined your first 2 board meetings and like the things you didn't realize were wrong. This person's leaving the company, you know, like, and other people are really excited to invest, you know, in part because Sequoia invested and in part because like company is obviously like interesting. Like that's the investment that probably like time and time again, like I and we have screwed up, you know, it's just, it's just really, really hard.

Yeah. And it's like, you know, you're the first explanation is, oh, you're, you're price anchoring, right? It's like, you know, how do you reevaluate? But it's not just that. It's like across all these different dimensions, you know, you know, it's the validation of getting somebody else who's going to pay a big price for this company. I just— yeah, yeah. Speaker B: Now you're getting a markup versus— Speaker A: yeah, it's like, but that's the one. That's the one. If I could just like You know, if I could just solve that problem on my investments, you know, like that would be the snap my fingers.

And I try so hard, you know, like change your process, change your, you know, change how you think about things. Ignore the board deck, study the board. Speaker B: You know, you're like manipulating your own psychology, trying to. Speaker A: Yeah. And so far it had little effect, but I'm only 35, so I can figure it out. Speaker B: You wrote some lessons from your first 10 years at Sequoia, and one of them was don't flinch. Can you talk more about what you mean by that? Speaker A: Yeah, I think like opportunities that you're really excited about reveal themselves highly infrequently and never at opportune times.

And I think, you know, for me, my, my proudest moment as an investor was, yeah, seeing Dylan at the New York Stock Exchange. That was the coolest thing ever. And just I was just so happy, um, for that hope for everyone at Figma, given, you know, the acquisition and the antitrust and the whole thing and just like seeing them there and just like, that was my proudest moment as an investor. Second proudest was this investment we did in Robinhood in 2020, the first week of COVID which was, um, you know, I dreamed, I grew up around New York City.

I had dreams of, you know, facing, I think, and I graduated high school in 2008. So like, you know, this is like the, like when I was, you know, entering the adult world, like the financial crisis in New York City was the main event, you know, and I had always kind of— I remember I read The Big Short right when it came out and I had to go, how am I going to react to like a crisis in finance? I picture myself on Park Avenue, you know, like, like wheeling and dealing, going to a boardroom, making a deal happen when you know, things were blowing up and then you, you know, that's how you envision it in your head.

And like, I really wanted, you know, and she pointed out this traffic. I really want to be a great investor. I really wanted to be a great investor. I like imagined myself in that 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 And I had, you know, an eighth of my wardrobe there. and I was doing circles around my pool. I was very happy to have a pool, you know, but it was like doing circles around my pool, talking to Vlad and Beiju about this investment when, you know, the market was gapping down 5 points every single day.

But Robinhood was like, you know, this is back when you could double your money on Boeing and then, you know, 16 minutes. Um, and we, uh, did a $200 million check right that first week of COVID You know, the app was down for a whole day. It was chaos. And, to me, like, when I say don't flinch, like, I was so— I felt so proud that, you know, just not being scared of that moment, you know, in part because I prepared myself for it for so long. Like, what was— what would the guy you want to be do in this moment, you know?

And similarly, like, dealing with, you know, legal battles that you end up entrenched in and otherwise, like, I think you just, like, can't let yourself down, you know? Like, I think all of us I like to imagine how we'll react in these, like, really high-stress, high-stakes moments. And yeah, don't flinch to me just means, like, just do the thing you know you should do. Speaker A: Yeah, I think like opportunities that you're really excited about reveal themselves highly infrequently and never at opportune times. And I think, you know, for me, my, my proudest moment as an investor was, yeah, seeing Dylan at the New York Stock Exchange.

That was the coolest thing ever. And just I was just so happy, um, for that hope for everyone at Figma, given, you know, the acquisition and the antitrust and the whole thing and just like seeing them there and just like, that was my proudest moment as an investor. Second proudest was this investment we did in Robinhood in 2020, the first week of COVID which was, um, you know, I dreamed, I grew up around New York City. I had dreams of, you know, facing, I think, and I graduated high school in 2008.

So like, you know, this is like the, like when I was, you know, entering the adult world, like the financial crisis in New York City was the main event, you know, and I had always kind of— I remember I read The Big Short right when it came out and I had to go, how am I going to react to like a crisis in finance? I picture myself on Park Avenue, you know, like, like wheeling and dealing, going to a boardroom, making a deal happen when you know, things were blowing up and then you, you know, that's how you envision it in your head.

And like, I really wanted, you know, and she pointed out this traffic. I really want to be a great investor. I really wanted to be a great investor. I like imagined myself in that 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 And I had, you know, an eighth of my wardrobe there. and I was doing circles around my pool. I was very happy to have a pool, you know, but it was like doing circles around my pool, talking to Vlad and Beiju about this investment when, you know, the market was gapping down 5 points every single day.

But Robinhood was like, you know, this is back when you could double your money on Boeing and then, you know, 16 minutes. Um, and we, uh, did a $200 million check right that first week of COVID You know, the app was down for a whole day. It was chaos. And, to me, like, when I say don't flinch, like, I was so— I felt so proud that, you know, just not being scared of that moment, you know, in part because I prepared myself for it for so long. Like, what was— what would the guy you want to be do in this moment, you know?

And similarly, like, dealing with, you know, legal battles that you end up entrenched in and otherwise, like, I think you just, like, can't let yourself down, you know? Like, I think all of us I like to imagine how we'll react in these, like, really high-stress, high-stakes moments. And yeah, don't flinch to me just means, like, just do the thing you know you should do. Speaker B: Hmm. Seemingly your conviction, and I think the results would say success, rise to the occasion with stakes. Like, you— the relationship between conviction and stakes for you increases.

I don't think— maybe that's in the answer you just gave, but I don't think that's necessarily obvious true for everyone. Maybe it is true for all good investors, but is there either a psychological or even like an internal mechanical way you relate to, yeah, meeting, meeting, meeting the stakes with a supreme amount of conviction in getting to the point where you're not going to flinch in those types of moments? Speaker A: You know, I think I mentioned earlier in the conversation, like having your first investment be Robinhood, has paid huge dividends for me in that what could possibly be more stressful than the GameStop week, you know?

And then, you know, that was one of 7 really challenging weeks at that company. I think once you— when that's the norm, you know, everything kind of just like, like your heart rate doesn't move that much. Speaker B: Forged through the fire. Speaker A: Yeah, a little bit, right? It's like I think that the people who came up through crypto, for instance, have like a very unique psychology for the markets because, you know, you faced 17 drawdowns in the same— massive drawdowns. Speaker B: I was born in the darkness. Speaker A: Yeah, no, I think it's a real thing, you know, in terms of like I was thinking about, you know, like the Figma M&A, you know, unwinding and then subsequent success on IPO.

Speaker B: What was that period of time? Speaker B: I was born in the darkness. Speaker A: Yeah, no, I think it's a real thing, you know, in terms of like I was thinking about, you know, like the Figma M&A, you know, unwinding and then subsequent success on IPO. Speaker B: What was that period of time? Speaker A: What was the gap between when the deal was signed? Speaker B: $20 billion Visa offer and then IPO. Speaker A: From Adobe. Speaker B: Adobe. Speaker A: Yeah, it was September, September to December.

So 14 months. Yeah, September to December. Speaker B: Some of those 14 months were— Speaker A: Yeah, you know, and then, you know, I took over the board of Klarna in a very like widely publicized, you know, like challenging situation. And I think I was like the perfect person to step into that and just like you know, help sort, help people sort through their things and get the company to the IPO. And, you know, again, like, if I could be known for that, you know, the person who's like very uncomfortable in like deeply uncomfortable situations, that would be a dream, you know.

I think I guess I've to keep proving myself, right? And certainly can't, like the way you do that is obviously you find yourself in them, you know, which is, you know, sometimes you wouldn't wish upon anybody. But secondly, you have to just like— I think it is helpful to imagine yourself like, how would I want to react to these sorts of things? You know, and I can think of plenty of situations where, you know, I wish I were more aggressive. I think like one example where I certainly flinched was like, you know, I brought in Vlad when Robinhood stock was trading at $7 a share and I like hadn't given up to the partnership and I was like, this seems like a good company, maybe we should invest.

And I just kind of got busy and just didn't follow through with it, you know. So I've definitely, you know, far from perfect, but yeah. Speaker B: You brought up boards. This is you, I think you were talking about how, uh, obviously like at least the common kind of trope is a board's job is to fire or hire the CEO. You, and you alluded to it just now, you've talked about also a role of a board member being a shock absorber, particularly in these moments of like chaos. And I think this is you.

You said startups are emotional. And I think one of the benefits of having a good advisor or board member is that we genuinely care about you, but we can also be objective when it's required. It's like asking your brother for relationship advice. Speaker A: Yeah. Speaker B: How do you bring humanity, empathy, vulnerability to that role beyond like, like in a way that is actually not like this BS cute thing and like a way that actually helps Sequoia make money? Like, how do those two things fit together? Speaker A: Yeah, I think companies are, um, you know, like, life is hard, right?

And I think for, I think for founders, it would be better for their psyche if, you know, their ego wasn't wrapped up in their business so much. But I think that's like a lot to ask for somebody who is in the, you know, eye of the storm building a company, you know? And with like so much weight and responsibility and so many people counting on you. Like, I just— people can kind of experience their ego death later in life. And while they're running the companies, have to recognize that like every up and down that the company goes through, they're going to wear, you know, way harder than you possibly imagine.

Yeah. I was talking to Ravi Gupta, who is somebody I really admire and I've worked with now for a long time. And Rev describes him, he's at Instacart, just like whenever an investor, you know, would tell him like, have you thought about this, this some idea? And he's like, you mf'er, I think about this company 20 hours a day. You know what I mean? Like there's nothing you've thought about I haven't thought about, right? Speaker B: Oh, you got a suggestion. Speaker A: Thanks. Yeah. Which, which, which, you know, which doesn't mean don't make suggestions.

It kind of just means like, that's not, you know, it's not, have you thought about this thing? It's like, surely you've thought about this way more than I have. Here, like, here's what I see, you know? Mm-hmm. Is one dimension. The other dimension is like sometimes people just don't want to talk about it. You know, it's like the fact that you have a meeting scheduled with somebody and you haven't talked about this really important topic, right? Somehow means now is the right time to talk about it, right? Like sometimes it's okay to go to a meeting and just like not talk about that thing because it's not the right time to do it, you know?

And you know, I say like, you know, meet founders as people, right? Like, you know, this is like a deeply personal relationship I have with the people I get to work with. And that applies to my partners and applies to the founders I work with. And, you know, like when I'm feeling like I'm having a hard time or struggling, like they hear about it too, you know? So often I'm looping in founders to like help me win investments, help me think through investments. Like, and I think like revealing that, you know, I don't have all the answers.

I really want your perspective. I think it's helpful for them because they can kind of come back and feel the same way. Speaker B: So you, when you're talking to the TBN, TBN guys, you said the first thing you do when you join a board is learn what business you're actually in. Speaker A: Yeah. Speaker B: Can you talk a little bit about that? Speaker A: I think that's like a, that's a Doug line. I think part of it is like you are being sold when you're, you know, investing into a company.

Speaker A: Yeah. Speaker B: Can you talk a little bit about that? Speaker A: I think that's like a, that's a Doug line. I think part of it is like you are being sold when you're, you know, investing into a company. Speaker B: Yeah. Speaker A: And even when, you know, companies are revealing, you know, the metrics they don't like, like they're often doing it in like the same way you will formatively open up to a new friend, you know what I mean? Like, allow me to tell you about my insecurities.

Like, if you're telling me so quickly, like, that's not the issue, you know? And when I say like, know what business you're in, it's like the bottlenecks kind of like reveal themselves in business. You know, we're trying to, you know, it's like systematically trying to remove the next set of bottlenecks to enable the next set of growth. And you do that time and time and time again until you're wildly successful. And if you go to the Microsoft board, I'm guessing they're thinking about the bottlenecks to their growth. And, you know, and, you know, you think you have a sense of the bottlenecks, but like, if a company is growing fast enough, it'll be a different set of things in 2 months anyway.

And like the interpersonal side, like, how does this person recruit, right? Like, how does— you've never been on search calls with them or seen them try to close a candidate, right? Like, How does this person manage a team? You know, like you, you just like learn so much about this business that you now own a stake in that you can't possibly learn when you're kind of on the outside. Speaker B: Yes. And you also have the psychology of being an owner, part owner of the business evaluating all this versus an evaluator.

Speaker A: Yeah. And again, this is why like that first investment thereafter is often so hard. Speaker B: Yeah. Speaker A: Because and I, you know, PSA, I love all of you, but like that first board meeting is very rarely like, holy shit, we're going to make so much money. You know, like more often than not, you know, it's like for the best, best, for the best companies, you're just getting like the, you know, lowlights. Speaker B: Yes. And you also have the psychology of being an owner, part owner of the business evaluating all this versus an evaluator.

Speaker A: Yeah. And again, this is why like that first investment thereafter is often so hard. Speaker B: Yeah. Speaker A: Because and I, you know, PSA, I love all of you, but like that first board meeting is very rarely like, holy shit, we're going to make so much money. You know, like more often than not, you know, it's like for the best, best, for the best companies, you're just getting like the, you know, lowlights. Speaker B: Yeah. Speaker A: You know, like there's a not uncommon thing where you'll like, a company will have gone from, you know, real example, I went for the name, you know, it went from, I think we're going to see a great investment, but we went from, it went from $4 to $20 million of revenue and we invested.

First board meeting, you get the thing, went from $4 to $20 on a plan for $33 or something like that, you know. So it's like, why we missed our plan so badly? And you on the outside, All you see is the 4 to 20, right? And yes, yes, you know, and that's like the perfect example, right? 4 to 20 is pretty damn good. Who cares what the, you know, 26-year-old finance lead suggested they might do, you know? Speaker B: Right. Speaker A: But when you're like listening to the 26-year-old finance lead explain the point— Speaker B: and they're not narrativizing it in a positive way.

Speaker A: Yeah, exactly. Speaker B: So is there ever a time when price doesn't really matter? Speaker A: Well, for me, price always matters. Speaker B: Maybe to go back to Figma. Speaker A: Yeah. Speaker B: As an example, you paid an obscene price. Yeah, maybe that's just all like, that's just the nature of this business. And there's always going to be people who think the price is obscene. Like what happens? You are certainly in the growth stage too. And someone with your kind of orientation, love of kind of like the art of business building.

Yeah. There are early stage people who are just like, it's all vibes, man. Speaker A: Like, yeah, smash it. Speaker B: Like founder bet doesn't matter. $100 million pre, let's rock. Speaker A: Yeah. Speaker B: You clearly have less of that, but like still you're— there are— there is a time where you're going to say like, I wouldn't pay an infinite price, but I'm going to pay a price, an order of magnitude beyond what makes sense. Like what, what's happening there? Speaker A: All right. Um, allow me to leak some alpha and it's like, this is on the flip side.

You know, I have a theory that no one actually listens to podcasts, you know? Speaker B: Ah, yes. Yeah. Speaker A: So, you know, no one will ever hear this, but you know, like one of my, like I did really well in that like cloud SaaS product growth wave of companies. And I think one of the reasons why is like I just never thought about companies on an ARR multiple basis because for companies that are growing really fast, you obviously grow out of that like very quickly, you know, and if a company is— let's just take $4 million of revenue, right?

If you got there going, you know, quarterly, 1, 2, 3, 4, right? That's very different than like 1, 1.5, 2.74, right? Like it's the net new ARR, like, you know, like what are you actually doing in the market this quarter that like is the true size of your business? So I always thought like a winning SaaS company should trade between 100 times to 200 times quarterly net new ARR, which says if you went from Pure Figma and you're at $4 million of ARR, but the last quarter was 2 to 4, you added 2 times 200, that's 400.

That's my line. Right? If you're doing $100 million net new ARR a quarter, guess what? I'll pay 20, right? Like it's, um, and that's like a heuristic that, um, I think actually works at basically like every part of the chain. It's not perfect, but it's a much better way of doing multiples than looking at an ARR multiple. Cause like, yeah, Figma is 100 times ARR, but it also is, you know, 4 times 2-year-out like ARR, right? So like, what's the right multiple? It's obviously the latter one, you know, but often I'll be like, I'll be with friends from other investment firms and I'll start quoting my like net quarterly and net ARR multiple math.

And they're like, what are you talking about? Speaker B: You can't do that. Speaker A: Yeah, it doesn't make any sense. You know, it's like, no, trust me. Like, if you look at your investments and go back and look at what price you actually paid, like, this is what actually— this is the market, you know, like the market doesn't do ARR multiples anymore. You're just not— you're not thinking about it like anyway. Speaker B: So I suspect there is a lot of that going on of just like there is a set of rules, rules that I kind of have to follow and that there's like you're not seeing the water.

Speaker A: Yeah, I mean, it's just like the— I feel like, you know, again, like I don't think this is novel or insightful or differentiated anymore, but, you know, like with the Vanta investment, we paid $480 for a Series A, right? Like Series A at $480, you know, but, you know, it was— I got from 2 to 10 profitable in the last quarter was, I think, over $3.5 million quarter. And I knew $480 is a good price, you know. Speaker B: Anyway, I don't think a thing people love to talk about, but on the note of conviction, how do you know when to sell?

Speaker A: You know, like mathematically, if you look at like the performance of founder-led companies and you own the whole basket, the answer is you don't sell anything, right? Like obviously we don't benefit from indexing and the biggest companies kind of run away. Yeah, but you know, Sequoia, we've like set up our entire business around this idea that like we want to be able to hold shares in the best companies forever. Because like the best companies, especially in the run by the best founders, you know, actually get better over time.

And Sequoia has learned some extraordinarily painful lessons on distributing stock in companies or selling stock in companies, you know, prematurely, even if it's an amazing gain. You know, I think we own 10 points of Google at the IPO. Speaker B: I mean, the Apple one's insane. Speaker A: Apple. Yeah. Selling Apple for a 40x on $150K, you know what I mean? Like, don't do that math. Yeah. So it's like, that's the, that's, that's the, you know, we're set up to never have to, never have to sell or distribute. Obviously you're constantly trying to rerun the math and, you know, if you get a 2021 moment where stuff's just, you know, unhinged, you need to be, you know, we are stewards of capital and we want to like our business, like I said, We're in the fund management business, you know, and we like really think about that.

But our default is like at an IPO, like you like aren't even thinking about the lockup, you know what I mean? It's like, what do you think? It's like very healthy. Oftentimes founders are thinking about the lockup and you're not, you know, and they call you like, what's going on? It's like, oh damn, you know? Speaker B: So yeah, you have a, you have a line where you said, and you, I think you briefly alluded to this earlier, you said learning how to be neutral to happy when other people get ridiculously rich is an important trait in investing.

I'm curious how you've managed your psychology, maybe on the inverse of your own success and like how again, maybe you were quite successful with, with the, with the first Robinhood investment. But at this stage in your career, you've had a tremendous amount of success. And so like hopefully a lot of that is feeding the right inputs for continuing to make good decisions. But some of it, I suspect, could— you don't want to get high on your own supply, I suppose. Speaker A: For sure not. You know, it's interesting. I think like this job is expressly humbling because companies so often undershoot their targets, right?

And even the best companies are often, you know, like if you're, if you're setting a good plan, you're making it most of the time, but missing it some, you know, if you're on 15 boards, like companies are always, you know, missing numbers and shit's hitting the fan constantly, you know, and you're just making mistakes left and right, right? Like you didn't see this investment, it turned out to be great. You're like late to the AI thing and your partners are doing better than you are. Like you're just constantly like getting harsh feedback, you know?

And I said this is like, you know, it was, you know, 2025 was no cope 2025. 2026 is no cope 2026. Like this is, I think for the rest of my career, like, you know, you just have to just just face the, you know, face the criticism head on and like really try to understand, understand it. And I think you can do that without taking it personally. Like one of the things I find so interesting is when people take pāčās at Sequoia all the time, you know, it's like because of our history and the legacy and people trying to position us like you just like you're just constantly hearing things, you know, and there's a point in my career when like when someone would, you know, me on Twitter, like, you know, making fun of us or whatever, it would just rile me up, you know, it's like, but then I realized, like, you know, if like someone's like criticizing me personally about my work, like I can live with that, you know, like why would I care if someone is like my employer, you know what I mean?

Like that's crazy, you know, but in the same way that, you know, founders' egos get so tied up in their businesses, like same with anybody who's like really cares about what they're doing, you know. Speaker A: For sure not. You know, it's interesting. I think like this job is expressly humbling because companies so often undershoot their targets, right? And even the best companies are often, you know, like if you're, if you're setting a good plan, you're making it most of the time, but missing it some, you know, if you're on 15 boards, like companies are always, you know, missing numbers and shit's hitting the fan constantly, you know, and you're just making mistakes left and right, right?

Like you didn't see this investment, it turned out to be great. You're like late to the AI thing and your partners are doing better than you are. Like you're just constantly like getting harsh feedback, you know? And I said this is like, you know, it was, you know, 2025 was no cope 2025. 2026 is no cope 2026. Like this is, I think for the rest of my career, like, you know, you just have to just just face the, you know, face the criticism head on and like really try to understand, understand it.

And I think you can do that without taking it personally. Like one of the things I find so interesting is when people take pāčās at Sequoia all the time, you know, it's like because of our history and the legacy and people trying to position us like you just like you're just constantly hearing things, you know, and there's a point in my career when like when someone would, you know, me on Twitter, like, you know, making fun of us or whatever, it would just rile me up, you know, it's like, but then I realized, like, you know, if like someone's like criticizing me personally about my work, like I can live with that, you know, like why would I care if someone is like my employer, you know what I mean?

Like that's crazy, you know, but in the same way that, you know, founders' egos get so tied up in their businesses, like same with anybody who's like really cares about what they're doing, you know. Speaker B: Yeah. Speaker A: And I think like you do need this like healthy dose of self-confidence in investing because you need to be doing investing, you know? Speaker B: Right. But also the downside is capped and the upside is not. Speaker A: Yeah, I think the biggest, the biggest issue people get into is like, I think you look at like a lot of the best venture investments ever, it's often people earlier in their investing careers, but it's very rarely their like first deal, you know?

And I think the reason is because people get frozen on their first investment, you know, because if you're like accumulating a portfolio of one. Speaker B: Yeah. Speaker A: You know, like the bar is just so high you can get stuck, you know, if you have a portfolio of 20, it's often hard to, you know, like be the first to something or like really deeply understand something nobody else can. Well, you got 4 or 5 companies and like one of them is pretty good. You're playing free. You see things really clearly.

You know, if this thing blows up spectacularly, it's not going to like kill your career. You know, like that's the lightness. That's like a really beautiful phase in people's careers, which is why I think if you look at like any partnership, you don't want everybody having been there forever. You don't want all novices. That was like, you know, or like not novices, but you don't want people who are like all building a portfolio at the same time. You want people at like different staggered development gaps, you know, I think about that sometimes.

Yeah. Speaker B: You said nothing you do before joining a VC firm prepares you for how multifaceted long-term success is. Are there any facets that are particularly top of mind for improvement as you maybe not enter but are kind of in the early phase of decade 2? Speaker B: You said nothing you do before joining a VC firm prepares you for how multifaceted long-term success is. Are there any facets that are particularly top of mind for improvement as you maybe not enter but are kind of in the early phase of decade 2?

Speaker A: Yeah, I, by my nature, like, I think very, in part it's because Pat, like, Pat cares so much about, like, how the venture business is run. Like, you know, how should we think about our structure and our team strategy and our, you know, processes and our pipeline and all that. Like, my brain just naturally gravitates outside the building, you know, like, companies. And for me, like, if your brain's out there, the world is changing faster and faster and faster. And so, like, I feel like for me, the main thing is like, how do I just, like, stay freaking relevant, you know, in every facet of, you know, the job?

Be it like, how can I identify the right founders? How can I, like, understand what a great company looks like today? How do you evaluate the market position, long-term moats, metrics of AI companies, which actually look quite different than the last generation of power companies in the data center world. Like I was Googling what a megawatt was like a year and a half ago, you know what I mean? Like, right, right. You kind of have to just like uplevel yourself so tremendously, you know, I'm at a different stage of my life than I was when I was 25.

And I like I had this amazing conversation with a woman named Kristin Faulkner. She was the 2024 Paris Olympics gold medalist and she was actually a two-time gold medalist, but she won the cycling road race in the 2024 Olympics. Speaker B: I think I heard about this person. Speaker A: And she was— yeah, she's incredible. And we had this, like, really wonderful, long conversation in August. She had just crashed out of, I think, the Tour de France. And she was just describing, you know, like, what brings her joy at this stage of her life.

And, you know, she had ascended to the mountaintop. And she was like, I know what it feels like. And getting to watch, like, my younger teammates feel that feeling for the first time. Is way better than feeling that feeling again. And that one comment, like, is going to stick with me for like the rest of my career because I know what it feels like to, you know, make a really cool investment, you know, and like start to feel like this winning feeling and do an IPO and sell a company, you know, like all that, right?

Like, but like getting to watch somebody else like feel that for the first time and like put themselves out there is like there's just so much joy in that. And I'm not like by my nature, like the world's greatest— I'm not a process. I'm not going to grind people and like, you know, make them do great work, you know? But I do want to get better at that. It's just like helping people find that moment, you know? Yeah. Because when you see it, it just— it's just like the coolest freaking thing, you know?

Speaker B: It's a great answer. I think we talked briefly about it, but there is obviously like a, a gut taste instinct kind of part of this, even in the way you evaluate the quantitative side of things. There's also a thing I found where you were talking about kind of like your focus on quality and craftsmanship in companies. When I evaluate a company, I talk to users, try the product, look at job postings, API docs, support forums, not just the slide deck and financials. Great companies have a consistency of design and experience that permeates the entire organization and every interaction with their customers, users, prospects, developers, attention to detail is important to me.

Why is— how does— and maybe it's super easy to point out with a company like Figma, but how does that kind of craft and attention to detail become a commercial input? Speaker B: It's a great answer. I think we talked briefly about it, but there is obviously like a, a gut taste instinct kind of part of this, even in the way you evaluate the quantitative side of things. There's also a thing I found where you were talking about kind of like your focus on quality and craftsmanship in companies. When I evaluate a company, I talk to users, try the product, look at job postings, API docs, support forums, not just the slide deck and financials.

Great companies have a consistency of design and experience that permeates the entire organization and every interaction with their customers, users, prospects, developers, attention to detail is important to me. Why is— how does— and maybe it's super easy to point out with a company like Figma, but how does that kind of craft and attention to detail become a commercial input? Speaker A: You know, I saw you last night at the Stripe Press event that Tammy Winter put on around the Stuart Brand book. And to me, like, Tammy's work on Stripe Press is the perfect example of how like an amazing culture, culture around quality and winning, you know, like just it ends up seeping like so deep into the organization, you know, all of its edges.

And I think if you examine amazing companies like at every angle, you can, you can see that same applies with the big Figma conference like Config, which they do. It's like Woodstock for designers. You know, it's like every little piece of it is just so freaking good. And like, good companies just do things so well. And then I think, you know, as it relates to like products themselves, you know, we're in this like Claude Cohn moment where interfaces don't matter and it's just like, you know, everyone's going to be a creator.

And I think that's a lot of that's true. As if like in a world of infinite software, like design and craftsmanship isn't going to be the ultimate, you know, arbiter of success. Like, it has never been more important to have like taste and an eye on when to stop and the ability to cull things. And, you know, I think craft in software is not just, you know, UI. It's like how fast the thing runs, right? Like, is it— Speaker B: attention to detail? Speaker A: Yeah, it's like just the— I think like design, you know, design in the full sense, not just like product design, but you know, the design of an organization and everything it does has like never been more important.

And that's probably shockingly somehow iconoclastic in, you know, early 2026. I suspect this time next year it'll feel very different. Speaker B: We are probably soon going to have computers that can do, uh, the quantitative stuff better than you can. Um, if not already. And so I'm curious how much of your conviction— and I don't think this is a perfect comparison, but like, how much of your conviction is about knowing versus feeling? Speaker A: This kind of gets into the taste thing too, but like, yeah, it's like the gut instinct.

Yeah, that you lean on. I have not and I will not use an LLM to write I've historically also not, you know, like quote unquote, I used our younger teammates to write. Speaker B: Yeah, yeah, yeah. That was their first LLM. Speaker A: Yeah, we have a, we have one of our, one of like one of our best young guys, his name Isaiah, and he just like cranks work like you've never seen. And he often works with Ravi and oftentimes will say that Ravi uses AI in his work and it's, you know, AI stands for actually Isaiah, you know.

So, you know, Remy's been using AI for a long time, longer than anybody else. But part of it's like this gut check where if I'm like working on an investment and, you know, we do like long-form memos, there's no sections. You start from a blank sheet of paper and it's like write out your thesis and like fill in the supporting evidence. And when I like really want to do an investment, I will sit down and I like, no matter what's going on, I will stay up through the night and at 6

m. in the morning, it's, you know, PDF'd and sent. When I'm like, so it happens a few times a year. I'm like really excited, sit down, start writing, and I just like lose this buzz. I lose the buzz and I don't even try to fight it. You know, if I hit that, hit that feeling, it's like, you know what? Like this might be a good investment, but like, this isn't what my best investments have felt like. Speaker B: Yes. So my friend Chris Pack says the same. He's like, I just have to, I have to be willing to do the work.

Speaker A: Yeah. Yeah. Speaker B: You alluded to Or maybe you talked about it somewhere when you first came into the firm, like, and you were starting to get your feet under you. It's like people come in and they can pick somebody to work with and it's like all of these legends and like 27-year-old Andrew. Speaker A: Yeah. Speaker B: And then you talked about how you started tweeting and a handful of little things. Like, I'm curious to what extent you're sending a bad signal now, how much you care about that.

You don't do a lot of podcasts. Like, how do you think about the legibility part of it? Speaker A: Yeah, I think when I started tweeting, first off, it felt more countercultural at Sequoia Capital than you could possibly have imagined. Like, I was like, you know, ducking for cover when, you know, I rolled into the office, like one of my tweets had gotten some people talking about it or whatever. And back then, I swear I was like the, maybe like the first actually good poster amongst the venture capitalists, you know, like, and That was the like 2017 era where like who you followed mattered a ton.

You could have like real alpha and just like your feed, if you follow the right 400 people, you could like know everything that was actually going on and not the noise. I think almost all content produced by investors is marketing, you know, like whether they know it or not, or you know it or not, like call it legibility or whatever. It's, it's, you know, it's a marketing document, you know. I think in the current, I think one of the things of LLMs is that you can produce like extremely in-depth content in mass about anything you set your mind to.

And like, I think these like market maps and things are like, you know, it's useful and it's good. But I think the thing you're trying to make legible is like, I actually get, you know, you actually get, get it somehow. And I think like for better or for worse, like connecting dots that people are connecting, and specifically doing that through humor is like, I think one of the easiest ways just to like make the, your understanding of a subject area. Hmm. Speaker B: Um, it's also like a person on the other side of the screen.

Speaker A: Yeah, exactly. And I think one of the things that, um, that Ava always says is that my tweets are like clearly funny to me, you know? And I think the, the subtweet is like, there's, they're not, definitely not always funny to everybody. But, you know, it's like the— he's having fun. I'm always chuckling at my own, at my own stuff. And it's great. You know, it's like, yes, it's like if you're not— if you know, if you don't think your posts are good, I can guarantee you nobody else does, you know?

Speaker B: So that's honestly— more of us would probably do well to remember that. You have a thing about big days. This is you. There's an old quote called Stonecutter's Credo that describes hammering at a rock 100 times without making a crack. At the 101st blow, it will split in two. And I know it was not that blow that did it, but the 100 that had gone before. I try to remember that in our work. You never know which days will be the biggest of your career, but if you stay focused and keep hammering, those days will happen.

I think this ties a little into when you were talking about not flinching, but what are— either can you give an example of a day like that, or just like, do you— does that, does that hold up? Is it kind of a string of years and a handful of big days? Speaker A: Yeah, I was just thinking about this this morning. We have a young guy on our team named James Flynn who is, you know, similar to Mike Martin. I think James Flynn is going to be well known in the Valley in 10 years.

Still very young and still developing and his tweets kind of suck. But besides that, James is amazing. And yeah, James, I remember James brought me to a company meeting. This would have been 16 months ago and it like showed up as like 1 of 5 back to back starting at 8 in the morning. And maybe it was actually, I think he was the, he put it before my 8 o'clock meeting on Zoom. It was like a Zoom at 7:15 or something. Speaker B: Nice. Speaker A: And James had been at Sequoia for less than a year.

And the last thing I ever wanted to do was do this meeting. And I remember like, I remember the feeling of seeing it hit my calendar when I was like, night before, and I realized I had to get up early, you know, earlier and miss my workout. And I was like, man, if this, I'm like ready just to be annoyed, you know? Speaker B: Yes, yes, yes. Speaker A: And then this is a, it's a crypto company that we invest in, haven't announced yet. It's probably one of the investments I'm most excited about.

And, you know, 2 minutes into the meeting, I was like, James, I love you so much, man. Like, this is like, this is so good. And to me, that's a good, it's a perfect example of like, you know, like some days it's like show up and if you're not ready for it, like that's a problem because it can be a 7:15 meeting that your 6-month India's career, young guy just brought you to that you easily could have said no to or anything else, you know. And then similarly, like, I think there was a day— I wish I remember the names— like Doug brought in, I think it was Aruba Networks and something else.

Two of Doug's like big billion-dollar gain IPOs like happened on the same Monday partner meeting and he had both— he did memos for both of them. And had them present back to back. And it's like, to me, like, that's like the guts of a great investor, right? Like, you would love it once a quarter. You had some amazing investment opportunity present itself, but it's more likely like you're deep in the weeds on one. Next one's there and you got to be ready for it. Speaker B: Christmas, whatever, right? Speaker B: Christmas, whatever, right?

Speaker A: Yeah. And it's like, what I think of, like, you know, would I be capable of having, like, the work ethic to, like, really evaluate two things in parallel and win those investments in parallel? Speaker B: Yes. Speaker A: Knowing how single-threaded I get, like, I don't know, you know, that's, but that's, you know, that's why it's like Leone, you know, so. Speaker B: There's a view that says, you know, there's the parts of investing, there's sourcing and there's picking and winning and, and building companies and so on. There's a view and I'm, I think clearly some of your investments have shown this is not always the case, but there's some view that says a lot of time in growth and maybe especially at a firm like Sequoia, like it's actually about winning, when rubber meets the road, sometimes it's like everybody kind of knows the companies.

Um, and again, I, I don't, I don't think that's totally true, but to the extent that is sometimes true, what makes you a great closer? Speaker A: You know, I think I used, I used to have on my Twitter bio, like, references available upon request, you know, I think founders listen to other founders, which is why winning your first one is really hard. But once you got it, like, yeah, it's like talk to other people, you know, see what they say. And obviously you have to meet people where they are.

Like, I think you really have to show them that you believe in them and believe in the company and like enthusiasm and understanding and like a deep belief is like really important in the moment. I think in particular, like founders, I heard this amazing talk from this guy, Winston Weinberg, who runs Harvey. Which is one of Pat's investments. And, you know, Winston was talking about how, you know, like, it's like really important to founders that, you know, like, they know that you will like, just like go to war for them, right?

There's like nothing, like, you know, like whatever the fight that gets brought to them, like you're there for it, you know? And to me, that was like the best piece of feedback I could have heard. I think I needed to hear that, you know, he was giving a talk, and I was just like in the audience listening. And one of the— I think I've always like communicated to founders like I really believe, you know, but I think I'd be even better if I communicated. And by the way, like no matter what happens, like I'm here for it, you know, like, and maybe that comes out in references to Vlad or Dylan, you know, low moments and everything else.

But like, that's the thing. Like, that is who I— and then, you know, again, who do you want to be, right? Like, you know, I wanted to be the person who like, you know, side by side, shoulder to shoulder. Speaker B: Yeah, we'll rise to the occasion. What do you think the most common thing that maybe, maybe the most common praise and the most common criticism that founders who are referenced on you would say? Speaker A: You know, one time I heard that Madi, uh, from ElevenLabs told another founder that I was quote unquote low EQ.

It's like, what the hell, man? It's like, what do I— um, Marty, I love you. Um, I think I immediately responded back to him like, dude, what? You know, it's like, it's like, um, I think I have this like cabal of the best founders, you know, like-minded people, like really great people, you know, and it's not just, you know, people like Kevin Kelly and Matt Huang, right? And, um, Ravi and Pat, you know, like I'm just, I feel like I've just surrounded myself with these just like exceptional people. And I think like that's probably the thing that people like are most excited about working with me.

It's like, I don't think it's like a personality thing per se. How do you think I'm like? I show up, I've read the board deck, I'm excited to engage. I like love business and debating things and pick up the phone on Friday nights. But I think like more of it's like just the association with these other people, which is amazing, you know? And then criticism. I think there are ways in which I'm a subpar venture capitalist. Like, I don't think I'm— I feel like if I'm interviewing a VP product for your company, I am a— you might as well have, I don't know, anybody else interview that person.

I'm just like, I've proved myself to be a very, like, subpar interviewer of specific roles, you know, that oftentimes you're asked to go help with. On the metrics thing, like I've definitely gotten into ruts where I've like just been wrong on stuff. There's a period of my career I was convinced like gross dollar retention didn't matter. It's only net dollar retention because the cohorts, you know, and it turns out 2022 just like blew that up. And I was like, wow, you know, it's like this. So I get, I get stuck on some things like that.

But I do think people would say I'm loyal. Yeah. Speaker B: Every low EQ every once in a while. Speaker A: Yeah. Everyone, everyone's Yeah, I've been listening a while. I just do very— I say things in a dumb way, probably. Speaker B: Some questions about Sequoia. Extreme performance culture. There's this like Doug thing about the 10 rule, 10 tenets, and it's like number 1 is performance, though. Like all the other stuff is cool too. I'm curious how like an extremely meritocratic environment is both freeing and to what extent you kind of had to be forged through that.

Speaker A: I think it is, if you buy in, it's the best possible cultural attribute you could want in an employer, right? Like where it's, you know, like performance, you know, it's obviously like in the investment business where like your returns are lagging and it's like there is an element of subjectivity to it. But like, I think it's like if you know, you know, like right now with our team, I'm like, I'm like, I'll hear about a company I'm excited about it. And David Khan or Tony Huang had emailed them yesterday.

You know, it's like, I feel like it's happened to me 14 times in the last like year, you know, where it's like I'm like finding myself a step behind my partners on the companies I'm really excited about. And that is so good. You know, it's like, that's like, that is exactly how you want it to feel, you know? Speaker B: Yes. Speaker A: Same with Pat, like when he's, or Alfred, like he'll see something, I don't see it at all, you know, it's like, your instinct isn't like, let me argue you, it's like, explain, like just tell me, you know, and I think what it means for people like Isaiah or people like James or people like Anas, which is one of our young guys in London, it's like, if you can just put your neck out there, like you can just, and like people really want you to win, you know, people want you to succeed.

And then the downsides would just be like, my golf game's probably never going to get any good. Speaker B: Yes. Speaker A: Same with Pat, like when he's, or Alfred, like he'll see something, I don't see it at all, you know, it's like, your instinct isn't like, let me argue you, it's like, explain, like just tell me, you know, and I think what it means for people like Isaiah or people like James or people like Anas, which is one of our young guys in London, it's like, if you can just put your neck out there, like you can just, and like people really want you to win, you know, people want you to succeed.

And then the downsides would just be like, my golf game's probably never going to get any good. Speaker B: You talked about a criticism a little bit earlier. I'm curious, to the extent you're willing to share, the harshest or most effective criticism you've gotten. Speaker A: Hmm. Um, I had a breakfast meeting with Mike Moritz downstairs in this office where— and Mike's somebody who I think is the best venture capitalist of all time and also has the best way with words of maybe anybody in business. And he's somebody who's like looked after me my whole career and has, you know, done right by me time and time again.

In really low moments for me. I won't like share the details of the conversation, but it happened at a very important time in my career where I think I was just headed down the wrong track. He managed to give me this like feedback in a way that was like deeply cutting and like, you know, and also in a way that expressed like extreme belief in what I could go do. And my guess is at this point he doesn't remember this moment at all. You know, it was just like giving feedback to— yeah.

But I remember that sort of like I was heading down, I was heading down a path where I was like going to be the grumpy, disagreeable Icee, you know, I was kind of in a rut and I was like, didn't want to deal with stuff. And I was just like, pack and deal, pack and do everything. I'm going to do my investments and, you know, keep my ball to myself, you know. and he totally took me on the other side and yeah, changed my life. Yeah. Speaker B: This is you from some old job posting.

Sequoia trees can live thousands of years. Not only that, their wood production, their growth increases as they age. They resist the deceleration and eventual stagnation that befalls most living things. I think there's a broad sense amongst many people, many investors I've talked to, which is like, how much does what I do even matter? Like, there's like a lot of determinism. The companies are funded anyway. Whatever. And my sense is that you and Sequoia in this place have a deep-seated view that this institution is quite important. Why does Sequoia matter? Speaker A: Well, first, I would say that that job posting proves that even pre-LLMs, I could write like an LLM.

That's uncomfortable hearing that sentence out loud. Sequoia does matter. You know, it's like an iconic institution in the Valley. That has such an amazing history. And I think Silicon Valley is a place where, like, the history, like, really matters. You know, it's like this is Shockley Semiconductor, you know, all the way through. It's like this is— we're in this era, right? Like, this is— this is— will probably be in history books in one way, shape, or form. And we are standing on the shoulders of, like, you know, Don Valentine and Mike Moritz and Doug Leone and Jim Goetz and Roloff, like, these exceptional investors who've given so much of their lives to this place.

And like, if we're the ones who kind of just like let it just fall back into just like yet another, you know, VC and the history books are littered with that, like Hummer Winblad. Hummer Winblad was like the hottest VC in the world in the '90s. Like no one's even heard of Hummer Winblad anymore, right? Like So it's like we're not in some ways immune from that, you know? Yeah, it's like we— you carry on like a deep amount of pride in that fact, but it also like invites lots of criticism.

And if you don't do well enough in terms of making investments for the future and talking about the future, it's like you run the risk of being a fading star, right? Like, which is like the last thing any entrepreneur wants to hitch their wagon to. So it's like, we are not going to do that. You know, and like, we also know that the only way to, like, make sure that exists is to, like, take risks and, like, break stuff and, you know, face the embarrassment caused by mistakes, but, like, also capture a lot of the opportunities that present themselves to us.

And I'm really proud of the way that our teams operate. Like, really proud. Speaker B: We've— we talked about it with you. Speaker A: We— Speaker B: you already mentioned the people. Square brings in a lot of young people. And kind of trains them in your way, a lot of apprenticeship, etc. One of the things that comes up is a— some form of deep-rooted need to prove something. And so I think there are a lot of like, oh, like classic trope, like the dad died when they were 14 or like went through something crazy hard or whatever.

Um, maybe this even ties into your own experience kind of growing up, But I'm curious, like, the different ways that that something to prove can show up, like the different flavors of that. Speaker A: Yeah. There was this Sequoia Heritage event in Montana. It was actually, I was there with Dylan. We actually were there when the Adobe deal was going down and Doug was on a panel with Roelof and maybe Roelof and Michael and Neil Shen. And someone asked like, how do you guys hire young people? And Doug was like, oh, you know, he did the thing he always says, you know, people who are like, you know, on the surface, like, really high achieving, but like, deep down, this like, real fucked up thing, you know, it's like, we've got this like, one guy, you know, he's got this, he has like a twin brother and you think he's so normal, but actually like, deep down, he's more screwed up and competitive and can't lose.

And at the time I was, you know, now we have a second twin on the team, but it was like, I'm like, right here. Everyone knows, everyone knows you're talking about me. It's like, just, um, and yeah, I think that like, Doug is an amazing evaluator of talent. And yeah, we say people who are hypercompetitive with a heart of gold, like that is the entire rubric for our growth team. And, you know, like hypercompetitiveness comes from somewhere, right? Like, and it doesn't, it doesn't always reveal itself instantly. You know, you have to like really find it in people because there are plenty of 4.0 students at Harvard who do not have that dog in them, you know.

And there are plenty of people who've like done so much and achieved so much in the past, you know, come such a long way in their lives. But like, that doesn't mean they're going to succeed into the future. Speaker B: Yeah. Speaker A: And there's some people who, you know, I grew up in a perfectly normal family, you know, in a really nice house in a really nice neighborhood. I played sports, you know, I went to a good school. I got a great GPA, won academic awards and athletic awards. Like none of that, you know, again, that's Doug's question for me is like, why would I hire you?

Right. And like, it wasn't about any of that. And yeah, so it's why like sometimes people are like, oh, I'm not going to hire this guy. He went to Phillips Exeter. I'm like, you know how many great investors went to Phillips Exeter? Like, that ain't the problem, you know? Speaker B: So anyway, you mentioned you joined at 23. I think you were one of, if not the youngest Sequoia partner ever. How— and again, I think it obviously relates to part of what you just said, but like, how have you managed the sort of like being an early star?

Speaker A: I think the 4 years in the salt mines, you know, that helped. Did not feel like I was shot out of a cannon, you know. Speaker B: But you do Robinhood, you get that promotion. Speaker A: Yeah. Do Robinhood, which like felt like a good investment, then I felt like a bad investment, then a good investment, you know, and then you do a few others. I did Loom, I did Figma. I think the idea of like being like a star, right? Like, again, that's a cliche. It's like you never feel like a star, you know?

Like Doug did the Wiz investment when he was 64 years old in an Israeli company a zillion miles away from home when like he should have been on the beach or playing golf or whatever else. And just like, for lack of a better term, like mogs us with this, like, you know, multibillion-dollar gain right before he retires. Right. Right. You know, like, that's outrageous. Speaker B: Yeah. Speaker A: You know? Yeah. Speaker B: The bar can go higher. Speaker A: Like, you know, like, not even, not even like eclipsing the bar.

Like, I'm hoping to even see the bar, you know? And that's like a— I think it's probably a helpful thing. Yeah. From an ego check perspective. Speaker B: A few Sequoia people I wanted to talk about. The first, a few questions about Don Valentine. Interestingly, especially in the backdrop of how we started this conversation about founders, is Don's like this, like, market maxi. Like, even like whatever Stanford talk he gave around 2010, he's basically like, we don't choose people, we choose markets. Obviously, maybe the market has shifted broadly. Certainly Sequoia has changed its tone on this.

And so like Is it a much more— is it a more balanced view? Is it just that the market piece doesn't need to be said? Has something changed about the world? Speaker A: Uh, in answering this question, I— have you read the DTV book? Speaker B: I've read part of it. Speaker A: Okay. Um, the Sequoia that Don ran was nothing like the world today. You know, like, I think that's one of the takeaways from the book. Like, he did an amazing job building set of culture attributes and hiring people and making amazing investments.

Obviously, like Apple and Oracle and Cisco and Atari and like Cisco is really his crown jewel. You know, my favorite fact is, you look at, you know, Cisco's fiscal year end, I think it was July 26th last year, you know, it's like, you know, like because Don hated the having the, you know, like rigid fiscal year ending at the end of the year, he wanted to do something different. And so like his, like his legacy lives on in the July 26th fiscal year end. I think it moves around a little bit every year for Cisco.

But Don, like, and I was lucky enough, like, my first few years at Sequoia, Don was around a lot and I talked to him a bunch and he probably, you know, he knew who I was. If, you know, whether he thought about me as like somebody who would be a long-term member of the team, I doubt it, you know. And the thing that Don did obviously so amazingly was like hire Michael and Doug and then hand it off. And that like generational transition and just getting out of the way and letting those two work together and build like the modern Sequoia, you know, all the different businesses, geography, stages, so many amazing things that like I think that one thing, you know, getting the big decisions right, like the way that Don handed over this partnership.

Speaker B: So many other guys have had a pretty successful or even amazingly successful career in venture capital and then the story ends. Speaker A: Yeah. Yeah. Don, like that I think is like probably like if we do a good job with Sequoia into the future, the idea of being able to like hand it off someday to somebody else and just like know that like my, my time here worked, you know, and like I made it better is like, that's like the thing that I think drives a lot of us.

Speaker B: Yeah. Speaker A: Which is different than like maximizing my net worth and everything else, you know. Speaker B: Yeah, maybe on that note, uh, this might be from the book. Unknown to me at the time was Don's habit of counting the number of times a candidate used I as opposed to we. Candidates who favored the first person were dead on departure. Speaker A: It is from the book. Yeah, yeah. Speaker B: How does that— it's semantic, but how does that change your psychology? Speaker A: You know, it's funny, like the That's so ingrained in like the Sequoia ethos that like even when you write a memo about investment, like you just use the royal we, you know, writing the word I just doesn't.

The only time I ever used it was we were, when I was working on the memo for Fantom, you know, the Naga Studio crypto wallet, amazing company. It's just like, you know, on the back of some of the meme coin mania and I just like had to like excuse James Flynn, who worked on it with me, from like sharing his opinion on, you know, some of these meme coins, you know, And even then, like, Pat just like prints it out and circles the big I paragraph and is like, I would change this, you know?

And I was like, yeah, I know, but I just didn't want to have to like— Speaker B: I'm taking the arrows. Speaker A: Yeah, I'm just like trying to, you know, excuse James from having to opine on this topic. It like really is an important thing, you know? And like, even in this conversation, I think one time I described Open Evidence or Harvey as Pat's investment. And like, I know Pat's going to listen to this. Assuming people actually listen to podcasts and be like, why do you say that? You know what I mean?

Speaker B: So anyway, on Mike Moritz, the two best question askers ever, according to Don Valentine, are Mike and Steve Jobs. What makes a great question asker? Speaker A: To the extent you learned anything from Mike about that, I think from a legibility standpoint, like In some ways, I think I learned nothing from Mike because he's so, he's so taste-driven, intuitive. Like, there's no, like, how can one possibly do that? You know, like, obviously you try so hard to learn. I've picked up a zillion lessons and I'm constantly trying to like, you know, bring them to the practice.

But he'll ask questions that you just cannot possibly understand how they're relevant to that conversation, you know, and pops out the other side and has this like crystallized view of the future. My favorite Mike story is, it wasn't even an investment that he did, but like, I guess this predates me, but when he was, we brought in Yelp for the Series A when it was like, you know, a desktop restaurant rating service. And Mike apparently has a part of me, he's like, someday, I won't do my Welsh accent, like someday, you know, every restaurant's going to have a Yelp sticker in their window next to the Zagat sticker.

And like, yeah, literally it's in every fucking restaurant, you know, it's like, how does one possibly see that? You know, it's like so random, but so right, you know? Um, so yes, but now the question is like, he uses a method to get the ground truth on a person that has enabled him to pick time and time again through the generation on like the best sets of founders, like younger and younger and younger. How he does it beats me. Speaker B: Also from the book, this is Mike. When I interviewed with Don, I asked 3 questions and I have subsequently been asked them by countless candidates.

What does it take to succeed in the venture business? What does it take to succeed here? And when will I know that I have succeeded? How would you answer those questions? Speaker A: I think number 1 is performance, right? So the, you know, our score is 10, 10, 10. The first one is performance. Second one is teamwork. In Doug's words, if you don't have the first one, the other 9 don't matter. I think ultimately it's like, this is a numbers game and the numbers catch up to you in both ways, right?

If you're doing a great job and like delivering investment returns, eventually like you get this compounding, you know, benefit that reveals itself in a bunch of different ways. And if not, like, you know, when the tide goes out and you aren't doing a good job, like you exit the business. Speaker B: Yeah. Speaker A: I think that's true at every venture firm. So I'll say that's also how to succeed at Sequoia. But I think the second tenet really matters to the we pronoun teaming on investments. Like we have a 2-person deal teams max and it's like not uncommon for Pat to wingman somebody else.

Like Pat will be doing custom references and like writing sections of the memo for a, you know, unproven younger guy to go lead an investment. That's so cool, you know. And what was the third one? Speaker B: When will you— when will I know I have succeeded? Speaker A: Still working on it. Speaker B: What do you hope or think people ought to know or not forget about Mike Moritz? Speaker B: When will you— when will I know I have succeeded? Speaker A: Still working on it. Speaker B: What do you hope or think people ought to know or not forget about Mike Moritz?

Speaker A: I think to the previous question, you know, that ultimately it's about performance. And he put up the numbers. I mean, he put up the numbers more than you could possibly imagine. And now he's, you know, hard at work trying to fix San Francisco and pursuing numerous other for-profit and nonprofit endeavors. He can make it happen. Like, that's one thing he can do. He can definitely make it happen. Speaker B: A few on Doug. Doug, on an interview with, I think, with Patrick O'Shaughnessy, He said, he's like quoting somebody, it's like, it's so wonderful I can't explain it means run away.

Like, cool is the enemy of reality. I'm curious how you relate to that risk, if at all. Speaker A: I think like the way that Doug, you know, pursues the business is far more like legible than the Mike, like just somehow coming to some conclusion that you can't, you know, the interpretability of you know, Mike's decisions is impossible. Whereas with Doug, it's just like doggedness, you know, like, I mean, I wish people could see Doug winning investments. Like, you should talk to founders who have like been on the other side of this.

Like, I mean, it is like, like Mozart, you know, it's unbelievable. You know, though, even better, like when Doug, he would give these presentations of like a standard Sequoia deck, you know, like where a company would come and, you know, explain their business. And when we were visiting them and for the last 10 minutes, he's like, like, before I leave, let me just like tell you a little bit about us. And he would just basically shine the perfect mirror back on the company, like giving them, you know, showing them like in such extreme detail, like how well he understands exactly like their bottlenecks, doing it in a way where like he was not talking about them, like you know, giving them feedback, right?

He's talking about Sequoia, but like just nailing every single thing. And then just the hustle, like, you know, flying around the world, never on a never-ending basis, just like winning and winning and winning and just, you know, amazing leader. Yeah. Speaker B: Maybe a little bit related to the comparison. Doug described Mike as, as very intuitive, as you said, and he talked about needing to shift a little bit more that way when Mike stepped down, where he had been kind of the process guy. And I'm curious how, to the extent you felt the need to, how have you had any of that?

Have you felt any need to become more intuitive? Speaker A: I think I've always skewed probably more towards the intuitive side just by my nature. I think it was either Roloff or Jim. Roloff is like 200 IQ, like, you know, just, and understands everything like extraordinarily deeply to like the nth degree. And then Jim Goetz is like a networking guy from his previous company. And Doug was like working on some networking thing. And then at some point Jim just gets fed up and he's just like, Doug, do you know what the company did?

Somebody does. And Doug's just like, yeah, top of the rack. It was just, that was like the, um, of course we made like a zillion dollars, you know what I mean? Speaker B: But like, it's, um, it's a wild, wild oversimplification and very unfair, but there is a little bit of the bell curve here with Mike and Doug. Speaker A: Oh, But the thing with Doug is that like Doug is on the right side of the bell curve. Like the, um, I'm trying to think of, there's some of these like brain teaser-y puzzles.

We had to like unwrap metal things from each other or like, sure. You know, you know, we wanted these in our office that like someone brought in and like, of course everyone's spending the full day trying to like do this thing and, you know, Doug just rolls in, looks at it for like 3 seconds and is like, and pulls it apart, you know? Speaker B: Yeah. Speaker A: So to me, it's actually like they're both maxed out, but like Mike's the maxed out word cell and like Doug's the maxed out shape rotator, you know?

And that's— I think that's like, that's the best way to describe them. Speaker B: I guess the same question I asked with Mike, which is what do you hope people know or don't forget about Doug? Speaker A: I think like the, the Nubank investment, he's probably was in his late 50s when we did that investment and it was like a seed in a Brazilian credit card company. Having built his whole career, like doing enterprise investing, you know, I'm sure at various points he felt like, what am I doing? People are going to judge me.

Like, how, you know, but just like— Speaker B: Repotted the plant. Speaker A: Yeah, he repotted, you know, when the last thing he needed to do was go do that. You know, keep like Brazilian credit card company, like David interned at Sequoia. He's the guy who runs Nubank. And like we told you, it wasn't just like a random Brazilian credit card company, you know, But nonetheless, like sticking your neck out and being willing to look extraordinarily stupid at that age of your life and then just like dominating is— that's, that's like the stuff that I think like ought to be in the like, this is how you should do this job books.

Speaker B: I just have a few more things, more generalized. What's artistic about business? Speaker A: I think there's like an extreme nonlinearity across every dimension that is like really beautiful. Like there's just this way in which, you know, like it's just not paint by numbers, right? It's like it is nothing about business is paint by numbers and it's so multifaceted and it's changing so quickly and, you know, you can't possibly see the matrix. So you're just constantly just like seeing something a little bit different every single day and trying to find patterns, you know, And especially in like tech, the half-life on some insight is a year or two tops, right?

Because like, trades get crowded, right? And I think that's true in our business too, you know. I think that's just so cool. It's also stressful, right? Because like, you know, to the question of like, how do you know you're successful? It's like, if the metric that matters is like net new ARR for a software company, like, you know, we're only as good as our next investment. That's a line that we end all of our presentations on at Sequoia. If that's the, if that's the market that I'm in, like the next company, like, am I that good?

You know, like, how could I possibly know? Right? Like, in fact, I'm late to all these companies and David and Sonya are kicking my ass and Pat's doing better. And, you know, Josh Kushner is doing amazing and Neil Mehta is doing amazing. And it's like, oh, you know, it's so, it's like so intense. Right? Speaker A: I think there's like an extreme nonlinearity across every dimension that is like really beautiful. Like there's just this way in which, you know, like it's just not paint by numbers, right? It's like it is nothing about business is paint by numbers and it's so multifaceted and it's changing so quickly and, you know, you can't possibly see the matrix.

So you're just constantly just like seeing something a little bit different every single day and trying to find patterns, you know, And especially in like tech, the half-life on some insight is a year or two tops, right? Because like, trades get crowded, right? And I think that's true in our business too, you know. I think that's just so cool. It's also stressful, right? Because like, you know, to the question of like, how do you know you're successful? It's like, if the metric that matters is like net new ARR for a software company, like, you know, we're only as good as our next investment.

That's a line that we end all of our presentations on at Sequoia. If that's the, if that's the market that I'm in, like the next company, like, am I that good? You know, like, how could I possibly know? Right? Like, in fact, I'm late to all these companies and David and Sonya are kicking my ass and Pat's doing better. And, you know, Josh Kushner is doing amazing and Neil Mehta is doing amazing. And it's like, oh, you know, it's so, it's like so intense. Right? Speaker B: So anyway, you have a tweet, always suspicious of young people who are points guys.

Same with tax obsessive, lack of appreciation of opportunity cost of your attention. Which is hilarious, but also I think pretty profound. How do you remember the opportunity cost of your attention? Speaker B: So anyway, you have a tweet, always suspicious of young people who are points guys. Same with tax obsessive, lack of appreciation of opportunity cost of your attention. Which is hilarious, but also I think pretty profound. How do you remember the opportunity cost of your attention? Speaker A: It's a little bit of the don't, you know, don't outsource. You know, it's like the— I'm also suspicious of like productivity obsessives in the investing business just because like, you know, I think like you have to like follow the spark of your creativity and you need to have like You know, maybe some people can pull it off, but I feel like the, you know, every meeting has to end on the exact moment of time.

Like, your day's not going to be like that, right? You know, if you find something you love, you got to stay in the meeting and like deal with the consequences, you know? Yes. I think, yeah, I think like dealing and like making yourself in this future of like the AI future, I think forcing yourself to put pen to paper, I think is going to be really valuable. Speaker B: What did you learn studying the classics? You were, I think you were a classics and economics major. Speaker A: Yeah. Speaker B: Unexpected.

Speaker A: Yeah. You know, it's a left, left brain, right brain thing. Yeah, I was actually looking at this. I won the Latin prize at Amherst my senior year and there's two of us who won it. It's me and a guy named Kevin G, I think his name was, looked him up like 2 weeks ago, see what he was up to. He said SEC enforcement attorney. I was like, I'm looking at his LinkedIn profile. It's like, oh crap, you know, it's like, but shout out Kevin. You know, it's like, I think I learned a lot of the same thing I learned at Goldman, it was how to work, right?

Just like classics was a grind, you know, you're just translating every night pre-LLMs and like pre, you know, you're just sitting there just grinding with a dictionary and, you know, the Old Testament or the New Testament or the Iliad or the Aeneid. You're just like sitting there and just like you left like a mountain of, you know, pages in front of you and you're like just chipping away at it. Same with like working at Goldman. Like, do I do DCFs now? Like, no, it's like, no. But though, like, how would I just like get up in the morning and like prioritize your time and get through it.

And like when you're exhausted but you need to do something, like how do you— of course you do it, you know, it's— I think that's like that how to work and how to like really work hard. I didn't learn that till college, you know, I skated my way through high school, right, you know, and I just like got put in— I decided to take Greek 1 my freshman fall at Amherst and, oh, you know, anyway. Speaker A: Yeah. You know, it's a left, left brain, right brain thing. Yeah, I was actually looking at this.

I won the Latin prize at Amherst my senior year and there's two of us who won it. It's me and a guy named Kevin G, I think his name was, looked him up like 2 weeks ago, see what he was up to. He said SEC enforcement attorney. I was like, I'm looking at his LinkedIn profile. It's like, oh crap, you know, it's like, but shout out Kevin. You know, it's like, I think I learned a lot of the same thing I learned at Goldman, it was how to work, right? Just like classics was a grind, you know, you're just translating every night pre-LLMs and like pre, you know, you're just sitting there just grinding with a dictionary and, you know, the Old Testament or the New Testament or the Iliad or the Aeneid.

You're just like sitting there and just like you left like a mountain of, you know, pages in front of you and you're like just chipping away at it. Same with like working at Goldman. Like, do I do DCFs now? Like, no, it's like, no. But though, like, how would I just like get up in the morning and like prioritize your time and get through it. And like when you're exhausted but you need to do something, like how do you— of course you do it, you know, it's— I think that's like that how to work and how to like really work hard.

I didn't learn that till college, you know, I skated my way through high school, right, you know, and I just like got put in— I decided to take Greek 1 my freshman fall at Amherst and, oh, you know, anyway. Speaker B: I think you said somewhere that your favorite book was Dune. Speaker A: Yeah, I love Dune. Speaker B: Why? Speaker A: You know that feeling getting lost in a story, you know? Speaker B: Yeah. Speaker A: It's just the best. Speaker B: Like, no messianic aspirations, just being lost in the story.

Speaker A: Oh, no, I actually didn't read Dune until I was a young adult, you know, and it was like way past— I'd read about other sci-fi and I was like, I hadn't never gotten around to it. Speaker B: Yeah, I read it a couple of years ago. Speaker A: I just like, I was probably 24, 23. And it was just so sick, you know? Yeah. No, there's no, like, no reason for it other than just that feeling of, like, when it was over, I was like, damn it, you know?

Speaker B: Yeah. There's some mediocre books to go read afterward. Speaker A: Yeah. Yeah. Speaker B: Our mutual friend Tina told me to ask you, what is a film that has moved you to the verge of tears but didn't make you cry? Speaker A: Um, There's a film called Aftersun. Speaker B: I still haven't seen it, but yeah, I know it's coming for me. Anyway, I don't want to talk about it, but what's your favorite thing about Will that's different than you? Speaker A: You know, like, like, you know, the thing that I would love people to say about me is I'm like ride or die, you know.

Will is the most ride or die person I have met in my entire life. And I spent my entire childhood as a stutterer being protected by my little brother. And like having seen his like career success take off and, you know, getting recognition for like the person that he is, is like One of the most amazing things. Yeah, he is the most loyal human being I've ever met in my entire life. He's tough as nails. Yeah. Speaker B: One more thing. I'd like to read— you probably know it given that it's in your bio, but I'd like to read this excerpt from Island by Huxley.

It's dark because you are trying too hard. Lightly, child, lightly. Learn to do everything lightly. Yes, feel lightly even though you're feeling deeply. Just slightly let things happen and lightly cope with them. I was so preposterously serious in those days, such a humorless little prig. Lightly, lightly. It's the best advice ever given me when it comes to dying. Even nothing ponderous or pretentious or emphatic, no rhetoric. No tremolos, no self-conscious persona putting on its celebrated imitation of Christ or little Nell. And of course, no theology, no metaphysics. Just the fact of dying, the fact of the clear light.

So throw away your baggage and go forward. There are quicksands all about you, sucking at your feet, trying to suck you down to fear and self-pity and despair. That's why you must walk so lightly, lightly, my darling, on tiptoes, and no luggage, not even a sponge bag, completely unencumbered. How are you becoming lighter? Speaker A: I don't have to comment on that at all. That's perfect. You know, that's like, that's it. Speaker B: That's it. Thank you. This is wonderful. Thank you for listening. Before I leave you, I'd once again like to thank Notion for being such an instrumental part of making Dialectic possible.

Uh, I partnered with them at the end of last year and it's just been amazing to have more resources and leverage, but also get to bounce ideas off them. And more than anything, use Notion to make the show better, whether that be research, uh, before the episodes or going in afterwards, pulling out ideas, lessons, patterns that stand out to me. And again, you can check out Notion at com/notion. If you missed it, I also did a little fun Q&A with them on Instagram talking about how I'm thinking about the year to come and what I'm hoping to build with Dialectic.

I'll link to that in the description. Thank you again. If you enjoyed the show, please give it 5 stars on Spotify or Apple or like and subscribe on YouTube, all the places. Thank you for listening and watching. Speaker B: That's it. Thank you. This is wonderful. Thank you for listening. Before I leave you, I'd once again like to thank Notion for being such an instrumental part of making Dialectic possible. Uh, I partnered with them at the end of last year and it's just been amazing to have more resources and leverage, but also get to bounce ideas off them.

And more than anything, use Notion to make the show better, whether that be research, uh, before the episodes or going in afterwards, pulling out ideas, lessons, patterns that stand out to me. And again, you can check out Notion at com/notion. If you missed it, I also did a little fun Q&A with them on Instagram talking about how I'm thinking about the year to come and what I'm hoping to build with Dialectic. I'll link to that in the description. Thank you again. If you enjoyed the show, please give it 5 stars on Spotify or Apple or like and subscribe on YouTube, all the places.

Thank you for listening and watching.