No Reset Button: Reinventing Amplitude in a Post-AI World (Spenser Skates)

27:04It keeps me up at night. Yeah, it's not current. I have, well, okay, let me, let me, let me tell you, let me tell you how it manifests for me. I have a spreadsheet that every week I write down what stresses me out at the company. Because just putting that to paper and articulating it helps you control it. And if you look at that spreadsheet going back years, there's so much. A lot of it's people stuff, frankly. um and but a lot of it is about hey we're not moving fast enough to make this change i think we should be making in the business like that's the core you know if you had to pick out the top theme running through it that would be the one you write that every week for years yeah absolutely absolutely it's it's very helpful how many things in a week show up on that spreadsheet three to six or seven.

28:04Is it just like a sentence or is it a sentence, a phrase? You know, it's, it's, I try to seven, three to seven. Yeah. So, so I try to, it's actually been a very helpful tool for managing my psychology because, you know, the biggest reasons, I'll tell you about this. So one of the things, One of the patterns I noticed is that even among successful companies, somewhere around 10 years in, the founders will leave. And this happened, if I look at kind of the peer group for Amplitude right before, like you look at Optimizely, Mixpanel, PagerDuty, Intercom is actually an interesting case too. Founders all departed.

28:51it. If you talk to them about why that is and you get them to open up about it, it comes back to their frustrations around the people and their frustration with managing such a large organization with all these opinions that conflict with theirs and their ability to affect change through it. So one of the tactics I've used, and I don't know, I should look at it. It's actually probably like six or seven years I've been doing this now. Wow. Is, well, I'll write down what stresses me out. And most acutely, that'll be around, tends to be around some interaction from a people standpoint. And where that blocks me from affecting whatever change I want as fast as I want to.

29:42And so that helps naming it, I can't remember where this came from, but there's this mantra that's like naming something gives you control over it. So by writing it down, the stress goes from floating around in my head to in the spreadsheet on the screen. And that allows it to be managed. It's like, OK, now the spreadsheet has the stress. I don't have the stress. Yeah. Do you think if you looked back at that spreadsheet, how much of the things that you actually stressed about even materialized? That's a good question. Like, are they real? I think a lot of them. Or are they just like figments of your imagination?

30:25No, no, no. Most of the time they're real. You know, let's pull it up. Let's pull it up. And while you pull that up, I'll tell you, I have the same spreadsheet. It's in my notes. It's just a note. It's just a note. And every week, every time something stresses me out or makes me anxious, I just add that thing to the notepad. It's the same reason that you do it. Yeah. Are you reading through it? Yeah, I'm looking at it. Yeah, I'll just read some of these to you. I won't say names. Feedback to executive. different executive role feedback on building trust and vulnerability and then the third thing is how to hold people accountable and then the fourth thing is a third executive interfacing with leadership team so anyway just to give you a flavor and and and so writing it down allows me to take the stress out of my head onto the spreadsheet on a screen.

31:31And that gives you much greater control over it than that makes it so that you can compartmentalize that much more effectively. That's super interesting. And are all, are you, you're married yes kids no no no kids is when you think about stress does it start with work and then work backwards into how things in your life whether it's work related or apartment related influence your work for sure work is by far is is the stress in my life this other personal stuff moving apart Like, that's like, like, is moving apartments stressful for you because it's like, then it takes away from work? Um, yes.

32:21So yes, I'll tell you the calories that you spend dealing with moving apartments is being dislodged from work. Yeah. So that stresses you out really early on. I did this exercise of what would the ultimate founder look like? and here's what I came up with, which is no other commitments outside of work. So no family, no debt to pay off, no like, hey, I have this hobby, no nothing, like nothing, like singularly focused on that. No attachment to money. So willing to live very cheaply and not spend anything.

33:11obsessively curious about the work so like just obsessed with and really curious about whatever to build a successful business you got to do x whether that's hiring executives building product learning technology whatever recruiting a team you know raising from investors um no willingness to

33:44work for very long periods of time with no success and so no ego attachment to the success of what you're building and so you know just having a humility about where you are and what what success you've had. So anyway, so, so anyways, it's all these very, very extreme things. I remember reading this thing. Peter Thiel was like, yeah, notice CEO pays anti-correlated with has a weak anti-correlate, like it's oppositely correlated with the success of the company. I'm like, okay, that's easy. Don't pay myself anything. Okay. To the extent that's causal, that'll help. Um, and so it was a very extreme, almost like a fanatical, uh, archetype that you drew.

34:21Yeah. And so I said, okay, the more I can be this person, the more likely it is I will build a successful company. And so that's how I wired my brain. Before you started the company? Yeah, right around when I started. This was 2011, when I was 22 years old, just leaving my job to come build a company. And so I kind of wrote all these things. I'm like, okay, I have to be this person. The more I am this person, the more successful I will be. And what's interesting is the vast majority of people out there are not willing to change who they are mentally to go do this. And so I'm going to have an advantage over them.

34:59And that was, you know, that was one way I attacked building a company. It's very, and, you know, being, trying to be almost too extreme on, on all the dimensions I just outlined. Fast forward, we're now 14 years later. um and that served me well like i've i'm more successful than my wildest dreams on amplitude and and what we've built um you know way further i mean yeah we've i'm still shocked that you know if you actually ask me to sit down and think in retrospect about it you know you don't really have time to but if you if you force me to i'd be like yeah that is that is kind of crazy so i'm incredibly lucky with the success of it.

35:47And then you get to this stage and you realize, you know, life is longer. There's other, there's other facets to it, you know? And, you know, I've been almost pathological about building this business for over a decade. And so, you know, it's okay to make space for other things and that makes it sustainable. And that allows you to go from doing it for 10 years to doing it for decades. So that's the change. that's the change. And so, you know, things like, Hey, I got to move my apartment, whatever, like, you know, it's fine. Like there needs to be space in my life for other things. My wife, my family, my, um, you know, my living setup, what have you.

36:24And that allows you to sustain even longer. Um, we were just joking about this. A lot of myself and Curtis and Jeffrey and some of the early folks at Amplitude, it's like, yeah, we're like, we work way less hard now in our thirties than we did in our twenties back then. And, you know, that's part of being more mature and evolving in life. And so, you know, you shouldn't just try to keep being, you know, you have to, you have to evolve into what the new thing is in order to make it sustainable and long-term. We also joked about like, man, we got to get more folks. We got to get more folks who are kind of pathological like we were when we were in our twenties.

37:01Do you, are there any things on that list that you, okay. So like apartment, great. You like increase size and space. You also have more money, so it's easier to do that now than when you were 22 living in your co-founder's room. Are there things that you're not willing to relinquish from that identity? This takes up a huge amount of my life. This being Amplitude. Yeah. Building a company, amplitude, the business, me being a founder, CEO. And I thought at some point I would have to relinquish that to focus on building a family, getting married, having kids. I was lucky enough to meet someone, my now wife, Anne, who we've been together almost 10 years now, who actually embraced that aspect of me.

38:01The fact that I was so obsessive about building a business and the craft of doing it and just like intensely focus on that. That means I don't actually have to relinquish that part of my life. And so now other stuff has changed, like the money thing. that was a very long, very long, very long disagreement between me and and I realized I was overly stubborn. Where you should pay yourself basically? Yeah. Well, yeah, I should pay myself a reasonable amount where I realized I was being stubborn. Can I ask how much you were paying yourself? That would frustrate? Oh, it was really bad. I mean, you know, at first it was like 30 or 45 K a year.

38:41Well, at first it was nothing for a while. And then it was like 30, 45 K a year, like a tiny amount. And then eventually I got to like closer to market, but still on the low end, you know, as I get to a hundred K, you know, now, um, now I like pay myself 450 K a year, which is still in like the bottom 10 % of, of comparables. If you look at public company CEOs in my position. Um, but I was like maniacal, you know, where I'd be like, Oh, so I'll pay myself anything, you know? And, and we had like a very small living space and, you know, we, it was it just made i i was attached i was in love with the religion of of not making money where it's like it forces you to be scrappy and focused and you don't have all these things to you know it's like the same more money more problems you don't have these problems and other aspects of your life to to deal with but i i realized that was that was overly that was you know it was too much um for its own sake versus hey help me be and you're trying to set an example for the company.

39:43Oh, totally. Yeah. Yeah. Yeah. You lead by example on that. Like if you're the most overpaid CEO, then everyone's going to be asking you for raises. Oh, absolutely. Yeah. Yeah. Yeah. It's, it's, there's also a lead by example part of that, but then, you know, I ended up realizing that was just stupid on my part. And, you know, there's actually, you know, there's things that unlocks too, you know, you have more resources to save time and ways and to get help with other things in your life. And, um, you know, and there is a part of you that, that does, that does genuinely enjoy nicer things sometimes.

40:11So I just, you know, that was an example of where I was, I call myself pathological on it and I needed to, and it was, I should have changed my mind earlier on it. Is there anything else? It took me time. I mean, just making, you know, I've gone from 95 % of my life space for building a company to maybe like 70%, so still the vast majority of it. But, you know, you have a little bit of room in your life for family and for relationships and for other peace parts of your life and, you know, for other interests. So yeah, you know, it, you know, but I'm still working. Can I ask you an honest question?

40:50Yeah. The, from the 95 to the 70, that 25%. Yeah. Do you enjoy it as much as you enjoy work? Do you genuinely - The other stuff? The things that you've opened up that space for. yeah i don't know what it is whether it's exercise or hanging out more and doing dinner do you do you do you actually enjoy it more or do you feel like you should be doing that no no no no no i if i didn't want to do the other things there are elements of well let me let me kind of categorize a few different things no like there are other there are other parts to my life that you know and i genuinely enjoy them i will say it's easier to just be a zealot and to just be like i'm focused on this no matter what.

41:34You just don't have to think. It's just like, okay, what is the thing that's going to make amplitude successful? Do that, block out everything else. It is easier. It's actually less cognitive load. It's much less. It's much less. It's like white jobs wore a black turtleneck every day. You just eliminate the load. You don't have to think about it. So it's easier in a lot of ways to be a zealot. It's much more straightforward. You don't have to make those calculations. um so so that part is harder but it's it's this is that balance is what allows you to go for further much further and much longer i would i think we have an amazing opportunity and potential i am not i'm not and that's real i'm not just saying i i genuinely do believe that and um i want to set up to, to go do it and take advantage of it.

42:21And to do that properly, that's a many more decades thing. And so in order to do that, you have to construct your life in a way that's, that's sustainable, um, where you can, yeah, where, where you can go, where, where, where, you know, you do have space for other things. I remember when I was 22, I remember I would compare myself to, like, I would think about people who had way worse life situations.

42:54Because that made it easy for me to be fanatical about building a company and the stress and life change that came with. I remember, like, you know, if you go back a generation, or parents, you know, or at least here in the US, you'd be drafted to go fight in Vietnam. That's like, man, compared to, yeah, being a conscript in a war. Yeah, this is easy. You know, if we're successful, we get paid for it. Or like, you know, if there are people who give up all their possessions and go become a monk in a monastery, it's like, hell yeah, starting a business is way easier than doing that. So I just, you know, I channeled a little bit of that energy just thinking about like, okay, let me, yeah, you know, let me be that person or compare myself to that person and think about, okay, this is actually, yeah, as bad as the problems I think I have are, this is easy compared to all of that stuff.

43:48And that helped me be crazy and fanatical and everything else. And now, you know, you fast forward 14 years later, it's like, okay, you know, do you want your entire life to be only that? No, probably not. You know, there are other aspects to it that are important too. And so it's good to make space for those. Did you feel like you were misunderstood? Were other people like, dude, let it go. Like, relax. Like, did you feel like maybe it was your wife with some specific things? Maybe it was people that you would hire? Like, did you feel ever frustrated that people thought you were trying to be somebody for the sake of being somebody?

44:28and in your mind you're like yeah that is what i'm doing like i'm trying to be the person that i want to be yes and it's very uncomfortable um

44:41so with my wife actually the reason i'm incredibly lucky is because she values that part of me and so like frankly i guess that's a whole nother story but i got lucky in in her finding me and her valuing that part of me. And so I never, I've never, ever felt like I've had to apologize or change who I am or whatever. And not to say, you know, you obviously may compromise in any relationship, but that core part of who I wanted to be, like, there's no question. I remember when I was in my early 20s, I was obsessed about it. And so obsessed about what it took to build a company. And so that would be the only thing I would talk about with anyone.

45:28You know, I talk about the stories of other entrepreneurs or what I'm working on or what I'm trying to figure out and learn. And, you know, not everyone's interested in that stuff. They had this, I remember a bunch of folks who were at MIT had this joke. They'd call me Startup Spencer because that's all I would talk about, you know, and they'd kind of joke about it, you know, because it would grate some of them sometimes that literally, You know, I was like, I had only one gear and that was it. So, but one of the, one of the advantages is like, you know, I just like part of me didn't, you know, it just doesn't care.

46:05Like, didn't care. Like, this is what I want to do. And so like, I'm very comfortable going to do that. And, you know, that's not a thing that every, a lot of people are interested in. And so, yeah, I was, I've always been a person, you know, I've always been a little bit of an obsessive personality and building a business was a good thing, great thing to attach it to. You know, it's just, we add joke sometimes with my wife, it's like, man, if we're going to be stressed and anxious anyway about stuff, might as well be about something worthwhile. Right, right, right. I feel the same way. When you were a kid, were you this obsessive?

46:46um i've always had i've always had traits that are you know what they call on the spectrum you just get really interested in certain things um and just you know kind of block out everything else and you know space out about the rest of the world so did your parents recognize that they did yeah they did are your parents like that they are they are so you were raised that way yes yes and when maybe if it's too personal you know i'm happy to talk about this but like when when are your parents still around yeah yeah yeah there's they're still great you know do they in boston they're they're doing well do they want grandkids they do or but no they they they've always been clear they've always known that i'm gonna do whatever it is i want to do um and so So, you know, their ability to, they know their ability to guide that or change that or whatever is not going to happen.

47:45So, you know, they definitely do. My brother, actually, my younger brother has a five-year-old, Sterling, who's wonderful. And they spend a bunch of time with, you know, and eventually Anne and I will have kids. You think so? Oh, yeah, for sure. Yeah. You don't worry that that might take you away from the business? Oh, I worry about it all the time. But you do. We'll figure it out. Imagine yourself in situations where something's going on with the child and you have a problem at work and you have to choose the child and then you let something slip at work. Yeah. I mean, people have had the. How do you.

48:18How do you make clear choices between your work and your family? And that's been a dilemma for thousands of years. And so I don't, you know, and there's. lots of different ways people have constructed that for themselves. So I'm confident we'll be able to fit and I will be able to figure out a way that for us to navigate it ourselves. Now, the tension is real there. I think actually the biggest trouble people get themselves into is like, there's this whole, like, what I call, hesitate to say work life balance, but

48:58idea that it's like, hey, you don't have to make any compromises in between your career and your family. It's like, no, you absolutely do. Like you absolutely have to make choices. Like your time is a limited resource, the most limited resources, resource that every single person has, and you have to choose where you spend it, you know, your time, your energy, your focus, your, your brain. And so this idea that there's no tension, there absolutely is a humongous amount of tension. And we spend a lot of time, I think a lot of people get in the trap where they pretend there's none and they think they can do everything and that gets themselves into all sorts of trouble.

49:35I think it was Ruth Bader Ginsburg that had this, that said it, which is, you can have it all, but you can't have it all at once. So we'll have to figure out the choices. And, you know, we want we want to have kids. We want them to have a great life. And so, yeah, there's we'll have to figure out what the trades are with what we do on the work side. The part that's wonderful that I'm incredibly lucky to have is that, like my wife and is very much of the same mind of what the two of us are trying to do in life. And so I have confidence that as we navigate it, we'll figure out. In many ways, now there's 22-year-olds at MIT or 18-year-olds at MIT that are studying you, figuring out what their archetype is going to be.

50:18Is there anything that you would have added or subtracted from the list, knowing what you know now, 14 years later? Absolutely not. That was spot on. You think you're spot on? Yeah. I looked at, you have to remove other constraints from your life. If you have a lot of debt or you have a lot of other obligations, it's going to be tough to impossible to start a business. You have to be obsessed about it. You have to have a curiosity that drives and you have to be willing to do it for a very long period of time. All of those are fundamental to being a founder that is going to start a successful business.

50:54And you can find counterexamples here and there on it. But generally, that was correct. The part that I think I was late to, and I think most founders are late to, is the transition between going from a founder to a large company executive. And I feel like I've just figured that out in the last few years. I wish I had done that earlier. Like the same way I obsessively studied what it meant to be a successful founder, I should have studied what it meant to be a large company executive versus just showing up being like, oh shit, you know, you have all these people with egos and problems and, you know, they want to be compensated and this, that, and the other thing.

51:39And I should have studied how do you actually, how do you actually make that transition? And do you have like a new archetype now of the public company executive Spencer? Oh dude, it's, I do. And I hesitate to even share it because like it's psychotic. In a lot of ways, you have to become the person you hate. So let me give you an example. As a founder CEO, you are always leading from the front. And so if there's a hard business challenge or hard people challenge or hard technical, whatever, the hardest thing you got to go do yourself, because you're not going to ask anyone to do anything you would not do.

52:20So whether, you know, whatever thing is, whether it's on sales or product or PR or whatever, or culture, like you have to lead the best by example. Once you start, and that's good because, you know, why would you follow someone who's not willing to do, you know, Michael Jordan had this thing. He wasn't going to ask anyone to do something that he wasn't willing to do. So, you know, he realized in order to win a championship, he was too skinny. And so he needed to hit the weight room and bulk up. And he led and inspired the other teammates around him to do the same, like Scotty and others. And that was a huge part of them winning six championships.

53:01As a large company executive, though, it flips because there's too much to do. You can no longer be the best at everything. You can no longer lead by example, whatever. You don't have time. Business is too large, there's too much complexity. You know, now I have, there's thousands of customers, many different products and lots of different functions with an amplitude. I can't go lead by example on even a few of them. Like, you know, it's, it's, and so your mentality shifts from how do I, how do I lead from the front to, Hey, it's my job to kind of become the jerk executive, manage and deploy people or resources against a problem and evaluate its impact.

53:43and you kind of feel like a jerk because like, oh, instead of being in the trenches with them trying to solve the problem, you're just being like, hey, that - Like a delegator. That wasn't really good enough. You guys got to do a better job on this. And so you become, and you, you know, you become this like stereotype of an executive that, and the person you hate, which is like, oh, now, now I'm just the one crapping on everyone else's work and telling them it's not good enough. And so, anyway, so that's an example of a switch you have to make from a founder to a large company executive that's really, really hard.

54:15I'll give you another example of one.

54:22So compensation. You cannot delegate who gets compensated what to someone else. As the king, it's your job to say who gets how much gold. It's actually, there's actually, and so you have to become an expert at compensation. I had the mentality for a while, like, I don't want to, like, I don't pay myself anything. I don't give a shit about how much I earn. Like, why should I have to worry about how much you earn either? Like, you know, let's give it to some comp consultant, HR team, and they, you know, run some numbers and figure out what's fair and just give everyone's fair. Let's just move on from this.

54:59But it turns out choosing who gets paid what and what the company values is an incredibly important part of a CEO's role. Like you cannot delegate that. You can get help on it. You absolutely should. You should get benchmarks and, you know, input from others, you know, but you have to make the decision of what someone's worth or value to the company is. And there's, there's no getting around. You have to make a judgment about that. And that judgment, one of the ways you express that judgment is in compensation. And so you can't delegate that to someone else. You know, there's, there's this thing, there's this ancient history thing where if you look at the roles of king, what a king is across different societies, there's like three of them.

55:44There's, you have to be the chief general. You have to lead the troops in the field to win the battles. You have to be the chief justice. So you have to arbitrate disputes between, you know, your nobles throughout the realm. And you have to be the chief priest, which means you have to ask, you're the person in charge of asking the gods for their, for their blessing, for whatever it is you're trying to do. You need rainfall for your next crop. And so you fast forward to modern times and what the role of a CEO or an executive is at a company. It's actually quite similar. You have to say, hey, where are we going?

56:20What's the strategy? We need to go take this hill or we need to go build this product. You need to arbitrate disputes. You need to break ties. and then you need to rally and inspire people and get them excited about, you know, and get them excited for the future for all your stakeholders. So anyway, but that's a different, very different mentality from a founder CEO where you're kind of like the scrappy, you're the leader of the scrappy outfit that's trying to win this mission against, you know, impossible mission against all odds. Now you're in charge of running a kingdom and that looks very, very different.

56:56and your mentality has to be different. So anyway, this long story, this long way of saying, I wish I had, I wish I, in retrospect, I started learning about the large company executive mentality earlier and gotten in front of that versus all of a sudden you show up one day and you have all these large company problems and it's like, okay, these two executives don't get along. How do you solve it? Or, you know, hey, this person feels like they're not getting enough gold or, you know, hey, this person, you know, the troops don't feel like they're inspired or what have you. Do you think that the types of problems on your worry list have meaningfully changed, like in broad stroke categories from five years ago to now?

57:41Or do you think they remain relatively constant? Meaning, did you worry as much about the tension between people and executives seven years ago as you do now? um or is that the point of reigniting a new identity so the the before i did not have a framework and skills or more importantly the mentality on how to handle how to handle that those like how do you act as a chief justice and arbitrate disputes well it turns out there's actually a lot of good ways. You don't go one-on-one. You get all the people in the room and you force them to talk it out and then you navigate through it. Actually, one of my favorite phrases is if someone complains to you about someone else, what I immediately say back to them is what did that person tell you when you gave them that feedback?

58:41Because it sets a whole bunch of expectations. One, don't come to me with this. You got to give that person the feedback first. two you can't just give the feedback you have to hear what their response is 90 of the time that second part doesn't even happen where they're like oh i well i don't know it's like okay we'll go you know and so there's all these things that you learn about you know how to be the chief justice um and so before i would get these problems and then being very stressed about them because i do not handle them and problems almost overwhelmed me Now it's like, they still stress me, but it's like, okay, here's the method for resolving them.

59:21And I know how to get to an effective resolution that's going to be best for the company. Now, the interesting part is that in terms of what we have to do as a business, it's the exact same it was five years ago, 10 years ago, 14 years ago, when you first started Amplitude. It's build a great product, convince customers to use it. You're just doing the same loop again and again and again, but you're scaling it up. The part, and so the intuition around how to do that well, that's served me. And so it's, the dynamics of that problem haven't changed much. You know, it's like, okay, once in a while there's like, okay, now we have AI, you know, and how does that change things?

1:00:07But the fundamental motion is the same thing. It's been roughly the same. How do you build a great product or how do you convince customers to use it? That has not changed. And so the knowledge I built up over 14 years allows me to have the instinct I do about how to do that effectively. The part that changes is the, okay, what does it mean to be a large company executive and running a large org? That is dramatically different. do you um do you worry that some of the things that you want to transform into are just things that are not a part of who you are it's not a part of your core identity it's not the way that you were born it's not the way that you're wired to

1:00:57become let's just say the priest in that example of rallying the troops maybe that's just like not who you are. I actually, I love, I love being, I love being the priest in the general justice sometimes can get grading, but the priest in general, you know, inspire people and show them what's possible. That's great. That's a, I've been doing that, you know, I've been doing that from when I was obsessive about building companies at 22. So I enjoy that. It's different. You know, you guys speak on stage to hundreds of people and, you know, we were just in a, just in New York at an investor day last week and where we were reintroducing Amplitude to the public markets.

1:01:33And so it was fun to share with them about what the changes in the business and what we were doing. The one part that does get, that is get that, one of the transitions I'm still learning how to navigate is, so when you're the startup founder, you are singularly dedicated to the cause and you're asking kind of everyone else in the team to be so as well.

1:02:03Because you're fighting this battle against all odds and you need every bit of help you can get. At a larger company, there's not the same level of fanaticism. And so for all sorts of, you know, ownership gets diluted, things gets more complicated. And so there's part of you that there is part of me that misses out on that. But again, you know, that's just, you know, it's like you don't. Yeah, it's like. It's just a different. It's you get you get people who are much more specialized in their functions. And so the picture, the picture of, hey, what the company is trying to do overall, all fanatical dedication to it, you don't get that as much.

1:02:53And there's part of me that misses that. Are you tired 14 years later? Do you think part of the reason why founders end up leaving after about 10 years is just like they're tired? Definitely. So yes, absolutely. Yes, absolutely what? Sorry. The reason founders leave after 10 years, a big element is they're tired. I'm not. I'm not. There have been points in time where it's gotten rough, but I've actually, part of going from that 95 % to call it 70 % is that, yeah, you do have more space and more room for recovery. And I have more help and more resources. I have phenomenal. I'm very lucky to work with the executive team that I have and my co-founders and the board and the team we have broadly at Amplitude.

1:03:45And so you're no longer having a lead from the front on everything. I think a lot of reasons why founders get tired is because the company gets bigger. They feel like they still got to lead from the front on everything and it's impossible. They burn themselves out. You have to understand the transition in your role. One of the advantages of that transition as well is that because you're working through other people, you actually have a lot more leverage. And so you no longer, you know, the company is not dependent on you personally and the pace that you set. It's important you set the tone of how fast you want to go and you demonstrate that and hold people accountable to that, but it's not bottlenecked.

1:04:19So it's important And you set the standard, you have to set the standard, but it's not important. You're the one driving it all the time anymore. And so that allows you to set up something much more sustainable longer term. What were the things that you missed, like constructing this person, right? What were the things that you felt like, I actually do feel like I'm missing out? In terms of being a successful founder or in terms of just being a person? Being a successful founder, like what, what is the, what were the real and tangible tradeoffs of becoming the archetype? Oh yeah. Oh yeah. I mean, I, I mean, I'll, I'll tell you a few right off the bat, you know, first, you know, no money for a while, a very long time.

1:05:09That's like. And you felt that. I didn't care. I, I rewired my brain not to care. But you know, it comes up. You actually didn't care? No. What's money? I already feel. Didn't you want to go on vacation? No. Like I just, I already feel I am incorrect. When I was 22, I already felt incredibly rich beyond my wildest dreams because yeah, there were certain things that weren't accessible to me. Couldn't buy a house, can't fly first class. But I can still, you can travel relatively cheaply. I'm lucky I didn't have other dependencies in life. um you can you know being just being in san francisco you can eat amazing food from around the world for relatively cheap you know it's just like i look at the luxury we have compared to previous generations it's incredible you know i have a smartphone that's smarter than um going back 40 years like or 50 years like all of computing ever and so it's just i mean whatever i'm like i I, you know, that comparison to the conscript in war or to the monk, that's what I think about.

1:06:16And so I'm like, yeah, I'm incredibly wealthy. Like, I don't, I don't worry at all. So I've never, you know, and yeah, so that, that, that's very real. Now, did other people worry about? Yeah, for sure. Like, I remember my mom, my mom, so she's Chinese Malaysian, Chinese communities. It's always, you know, you're always comparing your kids among the relatives. It's like, oh, my kid's making such and such money at this thing and my kid's making. So I went from, I did a year in finance where I was making hundreds of thousands of dollars to now unemployed startup founder. It's like, yeah, she can no longer brag to her cousins about how well her son is doing and she worries about that.

1:06:58You're an algorithmic trader making hundreds of thousands straight out of MIT. And then you go into complete obscurity. Complete obscurity starting a company. But I knew I was comfortable with that bet and I had no concern on it. But yeah, other people worried about it. What are the trade-offs? The one, honestly, I feel the worst about. So money wasn't that big of a trade. Now it's later. Now that we're trying to start a family and all of that, you feel it. But at the time, it was nothing. The one I feel the most and I regret the most, it was the right choice. But I did miss out on that part of life.

1:07:37is just having lots of having friends and being social in your twenties. That's not to say I didn't have any friends or anything, but like, you know, I didn't focus on that part of my life. And so I didn't build a strong relationships with people. And so there's, yeah, you know, I missed out on that part of life experience and I feel bad I wasn't as good of a friend to - Like if, for example, on a Friday or Saturday night, if your friends were going out to dinner, going to grab drinks, going bowling, whatever, go to a basketball game, you would intentionally say no to that stuff? Most of the time, yes.

1:08:10Yeah. Yeah, I'd go out once in a while. What's once in a while? What was once in a while for you? I don't know, like every,

1:08:22it changed actually. Early on when I was first out here, I'd actually still go out quite a bit. I'd go out like once a week on the weekends with some group of friends. But then as the company ramped up and stuff got more intense, it was less and less oh um and then i you know i swore off romantic relationships for a while too because it was like you know everyone's like hey spencer you're too intense on this thing all you think about i remember i was on so one date um this is way before ann where i was like you know i always i'm so obsessed about the startup stuff that's all i talk about i need to make a point of not talking about anything startup related like i'm gonna just try that so i went out and this date with this woman and got to the end of the date and she made this comment to me she was like man spencer everything is like career with you and i'm like what the like i made a point not to talk about any of this shit like what but it had infected my brain to such a degree like i was talking about i think i was helping my brother go to a coding boot camp at the time and trying to set him up for success you know it's just you know you know typical typical you know 20 20 something year old that just had entered the rat race and was trying to figure it out that like it imbued so after that i was like all right whatever i give up like i'm just i'm not even gonna try for a while on this um and then i got very lucky because um ann and i had become friends and she actually she actually valued that that part of me um and i i told her very early on i was like hey you know i just this is incredibly important to me and i'm i i'm not in a place in my life where I can compromise on it right now.

1:10:03And you've got to be okay with that. And the vast majority of people I know are not. But she was very gracious and actually valued that part of me. And so it ended up working out. You know, here we are almost 10 years later. So I, yeah, that was one of those where it's like, I, you know, it just, it came at the time you least expect and you actually got to have this very fulfilling part of life. That's even better than you expected because you get someone who values you for who you are and you value them for who they are. And you have the shared vision of what you're going to go do together. Yeah.

1:10:39And now do you feel like the, like, was health a trade-off for you? It was, it was for the first few years. I was very reckless on that in terms of not eating well, drinking soda all the time, not getting sleep. um then after a while i realized that you know keeping your health up actually makes you more effective on that stuff and so it's actually good to regularly get sleep to cut sugar um to you know take care of your body to exercise um you know so so it actually that actually you can go like a year or maybe even a few years without doing that stuff but it's it ends up being a net negative in terms of you know if you were just to pathologically look at your output for a company even then, you know, taking care of your health is like, there might be short sprints where you might not, but in general, like it's a net negative for that output.

1:11:36If you don't. Do you feel the ramifications of not nurturing a community of friends now? Is that why you regret it? No, I want to be clear. I don't regret it in the sense like I thought it's the right decision in retrospect. I feel bad. I feel bad about it in a bunch of ways, but I, you know, that was the choice I made. Oh, because I want to be a good friend to all these folks who are friends with me and I value my relationships with them. And when you say bad friend, like you don't respond if they text you or something? No, I'll respond now. And I'll be clear, these days it's gotten different from how it was back then.

1:12:07I meant like in the prime. Yeah, yeah. Yeah, I remember like, I'll just call him out. Like one of my close friends from school, this guy named David Chent. And he was always incredibly gracious with me. You know, he would go out of his way to check in on me and see how I'm doing. And I deeply appreciated it. And I felt like I couldn't reciprocate at the same level. But he was so gracious. He even recognized that and was like, hey, you know, I just want to make sure you're OK and all of that sort of stuff. And, you know, hang out, you know, we hang out once in a while when I go to New York and I'll see him.

1:12:38And, you know, I just I texted him about this. We're both into like watching watching Starcraft. It's like competitive Starcraft online. And so I texted in this thing the other day on it. So anyway, I feel bad that I haven't lived up to my half as a friend to him, but he's been gracious about it. And I value his friendship. Is there anything that surprised you to the upside or downside of the things that you did or didn't do? Like that most surprised you looking back as most effective or most harmful in becoming the founder CEO that you wanted to be? Right. I mean, I mean, first, I'm just blown away by how far we got.

1:13:20I never I would have been happy if we were running, you know, some crappy little tiny business that, you know, somehow I'd managed to survive by a shoestring. And so the fact that, you know, we've not just done that, but gotten to lead the category we're doing and turn it into a multiple hundred million dollar business, you're just like, shit, like, dang, markets are large. um yeah i never never thought we'd have a fraction of the success um

1:13:50you know i i mean i have the i think i was slow to shift in terms of parts of the mentality as i said and then i i think there were aspects that like i was kind of pathological around like not paying myself for a while like i thought it would get us more success and in retrospect didn't actually get us that much success i mean it set the tone for who i was and that was helpful But it caused a bunch of pain on a bunch of fronts that I could have avoided. But those are all so minor. Those are all so minor. I think it's one of these things where it's like, you look at the data points, hey, if you change yourself in this person, I read a lot of Paul Graham's essays, you can find a startup and have some success.

1:14:34And you're like, great, that sounds like a great bet. And you're kind of not sure until you actually see it play out. And then you see it play out and you're like, wow, this is, you know, I, my gut wasn't sure if this was the case, but it turned out way better than, than you could have possibly expected. Yeah. I appreciate you doing this. Of course. I appreciate you being so candid. I really do. Okay. I hope I'm candid. I can't tell. No, I think you're very candid. Are you hiring? Oh, absolutely. Are there any key roles that you want to shout out? Any general departments? So much. We're looking for, oh, so much.

1:15:11I would say if you're at the bleeding edge of leveraging AI to mess around with large data sets, we want to talk to you on that. I want to personally talk to you on that because there is so much opportunity we're on such early days on and there's not many companies who have what we have on that. And so I'm trying to figure that. I'm personally trying to figure that out as CEO. When you hear the word grit, what do you think of? If you're willing to endure pain for a long period of time in the service of something greater, that quality trumps almost anything else. You guys have talked to lots of people on this podcast already, but anyone who's done anything worthwhile, that's the lesson through and through.

1:16:16And so the wisdom's out there. The hard part, I think I see most people, they'll make small adjustments in their life I'd say, oh yeah, be a little more grittier, work harder, blah, blah, blah, blah, blah, blah. But if you can rethink about who you are to think about, hey, I'm a gritty person. I am willing to go without pay. I'm willing to not have success. I'm willing to be obsessively curious about a problem to the exclusion of all else. They don't reframe to that extreme. So honestly, I got lucky in that. I was like, okay, let me take that word to the extreme and see what the outcome is. And it turned out pretty good.

1:16:54I appreciate you. Spencer, thank you. Oh, of course. That's it for now. If you liked the episode, please leave us a review or go back into the archives where we've done more than 200 episodes with some fantastic folks. This podcast is a Client of Perkins production and I'm Juven. Thanks for listening.