Spenser Skates | Failed Startup to $300M in Revenue

You've talked about that mentality. Touch a bit more on where that actually stemmed from.

I remember I did this thought exercise of what would the ultimate founder look like? Perseverance and grit. You wouldn't have any other commitments in your life and you'd be willing to do this with no success for a very, very long time.

Did you spend time with Sam? I did.

Yeah, I was very lucky. I'll tell you this funny story with him. I started arguing with him like stupidly and he looks me in the face and he's like, Spenser, stop being a pussy.

What does it seem like everyone else is mysteriously bad at?

So many companies get lost after going public as we're going on to bigger and bigger things. Thousands of customers, $300 million revenue business, and we're still very, very early in what we're doing.

Are there any stories that most people don't know?

The bet I made was if I study what it is like to be a great founder and great company builder, how far can that take you? Become the ultimate founder. You set up your life in a way to do it. If you look at Elon, Elon's like a classic example of this. I remember he was interviewed once a bunch of years ago being like, oh yeah, who's your hero? Who do you aspire? Who do you look up to? You know what he said? He said, and I'm like, oh my God.

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Very excited to be here.

We'll probably start as early as possible and then build up to present day and dig into stories that you probably haven't said publicly before or delved quite deep into. It'd be good if you could start before your origins and before your story, but actually with your family.

Yes, very happy to talk. It's funny, it's the first time I've been asked about my parents. But very happy to. It's funny, you don't normally get to talk about, you know, you don't really get to talk about them. So I'm glad you ask. My mom is from a small island off the coast of Malaysia called Penang. She's part of the Chinese Malaysian community there, and she grew up there and wanted to come to the US for college. So I ended up coming here for, for college. And then my dad is from Perth in Australia. And Perth has the feature of being literally the most secluded major city in the entire world. And so it's the, I think the city with the population over 1 million that's furthest from any other city over 1 million. So it's like very like middle of nowhere sort of thing in Western Australia. So he ended up coming to the United States for graduate school. And then my parents met in grad school in Boston and then yeah, had me and I was born and yeah, ended up growing up there.

I love it. And they were researchers, right?

Yeah, so they're both academics. So their research is in biostatistics. So it's about how do you apply math to understand cancer treatments, early detection of cancer, things like that. And so that was like, yeah, that was my world growing up.

How did that impact the way they parented you? Were they the classic immigrant parents where it was, you know, you must get the best grades and you shouldn't do anything else, or they're more flexible? And how did that actually impact you day to day?

Oh, my mom was actually— she wanted me not to be a typical Asian kid. And so she actually didn't want me to like be good at math and science. And she wanted me to like study music and study like arts and literature and all these other things. But her and I go back and forth to this day because I wish I had studied more and been allowed to excel more at those things. It was actually different from the, yeah, it wasn't like, you know, it's not like I had tiger parent or anything like that. In fact, my mom, you would use to make fun of other parents who were very much like those tiger parents where like the parents would like go out of their way to like get every opportunity for their kids and, you know, whatever, some additional education program or some, you know, extracurriculars or whatever school resources. Whereas like she was very different. So the elementary school I went to was a school named Amigos. Okay. And it was an English-Spanish bilingual immersion school. And so this— they would actually teach half the classes in Spanish. And so it was like half Hispanic kids, half like white and/or Black kids. And then like I was the one, like, you know, Asian or half-Asian kid in the school. So I was a very different sort of environment. And she wanted me to do that because it's like different, you know, and it's like, you know, you get to experience just different cultures and different environments in different ways. And honestly, as a kid, I hated it growing up because like I'm not a language person. English is already hard enough for me. So to try to learn Spanish on top of that, it's just like I was literally out of like a class of 20 kids, like pretty sure that was the worst one in Spanish there. So a lot of my childhood was like trying out these experiences I was like frankly terrible at and not very good at in a lot of different ways. But that also has some benefits in terms of exposing me to stuff. And so I always like to this day, like I have this thing with my parents where I'm like, man, I wish you guys sent me to like the math, like the good math program or the good science program or the good thing. But whatever, that's just, you can't choose your childhood. And I'm very appreciative of, they put a lot of work into me and my brother. And so I was very lucky to grow up.

That's funny you say that because You did quite well, obviously. You went to MIT, you got all 5s on your APs when you were in high school and you did quite well. Why do you still say that you wish—

Where'd you find I got 5s on the APs? That's crazy.

I'll give that to you. 10 APs, right?

Well, I did 13 and then there was 10 I got 5s on and there was 3 I got 4s on. It was so funny. I loved taking tests in school, which is like a crazy thing to say. Because it's like—

Was it just because you're competitive?

Yeah, it's competitive. It's kind of a way to show that off. It's a way, you know, it's like this little mini game that you can master. It's a way to, you know, quantitatively, you know, demonstrate how smart you are and something you can work at and improve over time. I was— So I grew up in Cambridge, Massachusetts, and Cambridge, you know, it's like the Berkeley of the East Coast. And so incredibly like left-leaning socialists, very like alternative, ways of teaching and parenting and all of that. So they make a big focus on like, oh, how much effort you put in or how much. I'm like, why does that matter? It should just be like, you know, you getting a good result and all of that. And so my rebellion against that, I was like, hey, I just want to be like a typical smart kid that like, you know, where that stuff is valued.

That's funny. And so did you end up going to where your parents grew up and your dad grew up when you were a kid? Any visits there?

Yeah, yeah, yeah, yeah. We'd go once a year to either Malaysia or Australia and visit my relatives there. And it was very, very different. Both very, very different worlds from like Boston. Like Malaysia is, Malaysia is a very interesting society. So it's like multiracial society, which is rare, but it's very segregated. So like if you're Chinese, you only hang out with like other Chinese people, but it was cool. It's just like a tropical place and like it's so freaking hot there that like you don't really go to do anything. It's not like, oh, let me go on this tourist thing. Let me see this hike. It's like, you're not gonna do that. 'Cause it's what instead you do is you go out to eat all the time. So like you'll go eat every, like, you know, you have lunch and then an hour later you'll be like, hey, you know, let's go out for food. I'm like, didn't we just eat? And it's like, you know, that's just the thing there. And the food there is incredible. And then Australia, Australia is cool. It's like, it's very like, very not many people, very open, very, it's like, it's like the wild, like especially Perth, it's like the Wild West a little bit, you know. And so we'd always go there. My dad grew up surfing and so we'd always like go surfing in different places in, you know, in Australia. And we had this, my grandparents had this one beach house in this place called Margaret River that we'd go, you know, whenever we visited Perth. And like I grew up very young there, just like learning how to surf and bodyboard and all this and like do all these water sports.

That's sick. And is your brother older or younger?

Younger brother, 2 years younger.

What was the dynamic there?

I was very, very mean to him growing up and I would bully him and I feel really bad in retrospect. I remember I did this thing where I'd like trade him nickels for quarters because it's like they look similar and then I'd like just call them names. And then I remember this one time Like, I just, like, you know, shoot a rubber band at him and then, like, to get even, he'd shoot one back. And of course, like, once he did that, I have to, like, do it, like, twice as many, twice as hard. And I'm like, Simon, the cycle of violence isn't going to stop until you decide to stop. And, like, he literally— he was— he was literally just, like, a nice, friendly person. And so it was just, like, me going out of the way to be very mean for, like, no reason at all. So I felt— I felt really bad.

But we—

as we got older, we all got better. You know, we'd, like, hang out, play video games together. You know, we still keep in touch quite a bit today. You know, we'll send each other just like stupid stuff on TikTok and stuff like that. My brother Simon is very, very different from me. He's like just kind of happy to be who he is and gets along very well with like tons of different people. And so anyway, I've like, yeah, I felt, I felt really bad about, you know, when we were so young and I was, I was, I was really mean to him. But you know, it's, it's, uh, it's been different since then because he's so gracious. He's never, he's never held that against me.

Yeah. That's awesome. And paint a bit of a picture of your friends back then. What would you do in your free time?

There was a group of us in high school. We would like go over to this one friend's house every day and like play Halo on his Xbox.

Which Halo?

Halo 2 was the big one. Like, so anyway, we'd like get like really into that, competitive on that. And then I remember one of my friends, Shin. Yeah, we do like, you know, a bunch of nerdy clubs together. So we did like Science Bowl and we did math club and we did like, you know, stuff like that. Then one day he says to me, hey, Spenser, do you want to do crew? Like rowing. And I'm like, why would I do crew? Like, that doesn't make any sense at all. Like, you know, why would I do that? He's like, yeah, but like, don't you want to get buff and stuff? And I'm like, I guess. Okay. So him and I show up to like this first crew recruiting meeting and then ended up joining. I ended up doing it for 2 years and which is funny because I'm like incredibly skinny and small, but it was fun. It was, it was like that. It's like, you know, to teach you on like just intensity, like there's, there's like It's like one of the best things ever to do that. So I'd do that and then we'd, I didn't really stand out in any way in high school. I was actually lucky to get into MIT. The best predictor of whether you get into a top college, at least back in my day, was if you are in the top 10% of your class and I was not. I was 13th percentile. And so it was like, okay, already on the first thing you're like not passing it. Now I had good test scores and on APs and SATs and I had compelling stuff outside of that, but that was really really hard. And I think the only— I remember meeting the admissions director for MIT at the time. They had to— it was— this was in the middle. There was like a scandal with the previous admissions director, and this new guy Stu took on over on an interim basis. And I remember saying hello to him my freshman year, and I'm like, oh, you know, you know, hey, I don't know if you remember me, but, you know, Spenser Skates, I'd love— you know, I'm very appreciative to be here. And he remembered me, um, and he's like, oh yeah, you're like the guy who did Crew. And I'm like, you recruited me for crew? Are you for real? Like, this makes zero sense. I like tried out for the MIT crew team and like I lasted like a month before being like, dude, I cannot do this. Like, this takes over your entire life. I don't know if it was like a fluke or they misunderstood me or whatever, but like, I, you know, there's an argument to say I shouldn't even have been at MIT, but I was lucky to be there.

And did any of your buddies go to MIT or what was their story?

No, there were two other folks from my year that went, but I wasn't as close to them. There were a bunch that went to other— one of them went to— this guy named Xu went to Harvard, and then this guy named— my close friend named Xin went to Tufts. And so different people went kind of different places. So I was kind of the only one, but it ended up being— I wouldn't have expected to get in. All the folks who had went to MIT from my high school had a very particular archetype, which is that they're very, very deep on math and science, And I think I was a little broader than that. And so my expectation was just to go to another top school, but MIT was the best one that I got into. It was like, all right, we're going here, let's figure out how to make the most of this.

But you studied biological engineering. I did. I assume by virtue of what your parents did.

Yes. Yeah. My parents were like, I thought, okay, if you're smart and you want to contribute to the world in some positive way, that's the path. So you do research. I thought, okay, yeah, I'm going to do biology research and we're going to help discover, you know, cures for diseases or advance the field in some way, whatever. And I had no idea about the universe outside of this, so I had no idea about starting a business. I had no idea about technology industry, none of this stuff, because, you know, I wasn't exposed to it kind of growing up or in high school in any way. So I just thought, like, if you're smart and ambitious, like, you know, you go on and be a biology researcher. And so that's what I ended up studying there. The funny part about that is that while I was there, I would spend a lot of my free time just programming because I found it fun personally. I really enjoyed it. Like you can create something, you can see the effect, you can run it, you can then iterate on it. It's just that like they've gotten that loop down. Like it's just absolutely incredible, you know, whereas if you're a biologist or, you know, if you're a biologist, I remember I did this one experiment and it's like the shortest timeline you're going to work on is like a week and like you might get a result after that, you might not, and you might iterate from there. Whereas like programming, it's like you write the thing, you could run it and see a website change like in seconds, you know, if you know, or yeah. So it's very, very quickly. And so I had done that kind of just for fun on the side. I had like taken a few CS classes actually before when I was in high school, I had my own IT support business. I'd like go around the neighborhood and fix people's computers. Yeah. $30 an hour. Yeah. Yeah. So it was great. It was great money. Like I think the, if you were to do like a regular job out of the Mayor's Program where they connect high school students with different opportunities around the city, you get paid like $6 or $7 an hour or something like that. And so like to be able to do $30 as a high school student, huge, huge deal. And then, you know, I ended up raising my prices to $50 and then more after time. And that was undercutting, if you were to hire someone from Geek Squad, it'd cost you like $100 an hour or something insane like that. And so actually, so anyway, I got into computers. Yeah, I built my own PC. It was actually some of my relatives in Malaysia that showed me how to do that. Yeah, like would take programming classes and stuff like that on the side at MIT. Cool.

Well, I want to hand you the paper I had mentioned now, and maybe we can go a bit through this paper and talk about your college experience. So this is your resume that no longer exists.

Oh, wow. You found it on SpenserSkates.com.

Found it on the Wayback Machine. And so it'd be fun to— my goodness, go a bit through.

So embarrassing.

Maybe actually, if you want to show that to the camera, I think that'd be funny. Oh my goodness. And let's go a bit through that. At the bottom, you say you liked Frisbee. On there, you won the BattleBots competition, did all sorts of stuff. You got, you got 5s on 10 APs.

That's funny. That's so embarrassing just reading this now.

It would be fun to go a bit through that if you're cool with that and paint a picture of MIT life. You came in doing bio stuff and then you coded, you won the BattleBots competition, which you first didn't win and then you won obviously. And there's all sorts of different things you did. And the most interesting thing to me is frisbee down there.

That's funny.

All sorts of things that I think could be unraveled and delved into, which I think would be fun if you want to go back in whatever way you like.

So at MIT for the First, it's so funny looking at this now. Wow, that's so funny. Yeah, where to start? So, so I did a lot of things. I loved MIT. It was, it was amazing. I think it's like this perfect communist utopia where everyone is incredibly friendly. There's no status or hierarchy games like you might find in other colleges and people are just friendly and welcoming and just open to sharing what they're working on and what they're interested about. And so you could, I just made friends with lots of different folks at MIT. Yeah, I did. Like I was part of, there was like a club Ultimate Frisbee team at MIT, you know, so like, you know, not, yeah, luckily not like the, yeah, crew team. Yeah. So crew is actually the only, so MIT's Division III school, but you're still allowed to have one Division I sport. And at MIT that's crew. So MIT competes against Division I colleges like the Ivies and, you know, a whole bunch of others in crew. And so like that's the level. So yeah, instead I was like, okay, let me downgrade to something that's just I do once a week, like that's fun. So I did like club frisbee. I wrote a few articles for like the MIT newspaper. I got really into my sophomore year, this club called Global Poverty Initiative, which is like, how do we tackle issues of poverty and solve that as a global thing? I did this thing called Camp Kessum, which is like a summer camp that's run by college kids that's specifically for kids whose parents have cancer. And so I just, people were just incredibly friendly and like, it was just a way to meet different groups of people and form relationships and all of that. Sort of stuff. I did this one thing called Next Act. It was like a musical play except I'm a terrible singer. So they like gave me a bunch of non-singing roles in it, which was cool. So anyway, so just, but it's just a good way to, but I wasn't a standout student anyway. Like my grades like were good, but they were not the best. My, like, you know, it's not like I stood out in any particular way. It wasn't until I came across Battlecode that I was like, wow, this is something that I want to be really good at. And it combined a bunch of different things that I really enjoyed. So first it was like a video game, you know, and so I was like very into gaming. Second, it was a, you know, you programmed to create an AI for this video game. And then third, it was a competition where if you did well at the competition, that was recognized. So, you know, top Tech companies would recruit there, a lot of top finance companies would recruit there, like high-frequency trading, you could get into startups, you get in a lot of different things if you did well at that competition. And so I was like, you know what, I'm tired of kind of being like medium in life, like let me really apply myself and figure out how to go big on this programming competition.

I want to touch on that. Why do you say that you're medium? I think by all objective metrics you had done well in school and you had gone to one of the best colleges and—

Look, I was doing well, I was doing well, but compared to folks who had really mastered their craft and were at the top and were like, say, let's say you're competing in national level programming comp or math competitions, or let's say you're at, you're playing sports at a national level, or let's say you're like a top student, like the top, one of the top few top students in the school, or let's say you get, you know, a lot of recognition. Like I wasn't at that level. I saw people at that level and I'm like, man, like am I capable of doing at a top level? You know, I was good on a bunch of fronts, but like frankly, I was lucky to get into MIT. And so there wasn't really anything where it was like, okay, let me show that, hey, I can be among the best in the world at this particular thing. There was no place where I had really done that up to that point. I think that the best was like I tested really well in some ways, But I wasn't standout. The best I had done was we got second place at the Science Olympiad my junior year. Yeah, 'cause I had prepped for the Fermi section and all that. But look, MIT, all of that incredible, very lucky to be as part of that. But aside from that, there's a lot of kids who go and graduate to MIT every year. So there's hundreds. And then you look at just all top schools, there's a lot of people who do that. I hadn't shown like, hey, I could really be, stand out in any particular way. That's what I meant. I'd never competed at a top level. Like I'd go to these competitions. Like I remember in high school, I got really into, like there's this one club I was part of, mock trial. I got really into it, you know, and it was like, you know, maybe I can be a lawyer. And so, you know, you go through a case and you'd argue actually before a real judge and, you know, you'd interview witnesses and do this, you know, and do this whole thing. And we would come to these competitions and we'd get our ass kicked. By like schools that had just, where the students just showed up better, they were more polished, they were more prepared, they were just smoother and slicker. And I was like, okay, maybe I'm just not meant to compete at the top level in something. Like maybe I'm just like kind of medium. And I didn't know and you just don't know. And so Battlecode was the first time where I was like, you know what, like I'm kind of tired of being middle of the pack on all these different competitions and things. And let me try applying myself and see if I can go out and be great in some way. And so for that competition, I prepared a ton. I recruited the top people I knew.

Your co-founder was on a different team.

My co-founder the first year was on a different team. But I recruited one of my other close friends named Steve and I went very aggressive. I prepared on the prior year's code for a month before and then that entire month-long period I cleared my my entire schedule. I literally didn't do anything else, didn't do any other extracurriculars and hang out with any friends. I didn't go to parties. I literally just like 10:00 AM to midnight every single day, go to sleep, you know, wake up the next day, do it again. I remember buying, I was like, you know what, like how do I show I'm like really serious with this? Like, oh, if I get a whiteboard, all great programmers will have a whiteboard. So I bought a whiteboard for our dorm and kind of set it up and like just got really, really into the, the competition. And, you know, we were among the top few teams that year and ended up pulling out first place. That was the first time I had like competed at a very high level with other very skilled people.

When did you end up reading the book Meditations by Marcus Aurelius?

Thinking about how to be successful and controlling your emotions just so that you react to the situation that you're in, that as a skill is just, that is what you do as a founder, frankly, all day, day in, day out. And the founders who master that do way better than, than anyone else. I remember I did this thought exercise of what would the ultimate founder look like? And you wouldn't care at all about how visible your success was. You wouldn't have any other commitments in your life. You'd have a very minimalist lifestyle. And then you'd have a very long time horizon. So like you'd be willing to do this with no success for a very, very long time. And in some ways you might say that that's pretty extreme, but like I did this exercise where I compared that to like, hey, what were— what are other life circumstances people go through that are harder than this? Well, frankly, there's a lot. Like, you know, if you go back a generation, people were— my parents' generation, and you look at the boomer generation, a lot of them were drafted into the Vietnam War. And it's like, can you imagine? That's brutal. I'm happy to do this where it's like, you at least you have safety and security and you have marketable skills and you don't make a lot of money, but you can make some money. And if you are successful, you get outsized success and recognition for this. Or let's say if you go and become a monk and decide to live a monastic life, like very, very different life setup where you're trading off a lot. And I'm like, cool, being a founder compared to that, way, way easier. So let me, you know, let me embrace that. And like, you know, we humans are social creatures of comparison. And so whenever, you know, you'd feel down, you'd just be like, okay, well, at least it's better than this other, like, really, you know, rough situation in some other life circumstance. And like, so I can, you know, still keep going on this.

You've talked about that mentality more broadly, a bit publicly as well. Touch a bit more on where that actually stemmed from. Maybe if you can tie it at some parts in your childhood. For me, at least a lot of ways that I think when I think back, there's something in my childhood or that kind of stemmed or there's some anecdote where it's an exemplification of that. Is there anything in your childhood where that kind of comes to mind where I have to do something for a really long time and prove myself?

That's going to sound weird, but like honestly, just being kind of mediocre and like getting my ass kicked by teams who were much better than me in like sports or clubs or whatever. Or school and like being kind of immune to that, the shame or the social judgment of failure, that was actually very, very important. The other thing is, I guess one of the things that I'm very appreciative of my parents, I'm very academic family and that loves to kind of debate and discuss things with each other. And, you know, one of the common responses like, oh, if you're so smart, why aren't you rich? Or if you're so smart, why aren't you more successful? And so almost as an experiment, I was like, okay, let me actually push a bunch of these thought exercises to the extreme. Like, okay, what if I actually embodied and became the ultimate founder archetype? Like, is that gonna turn out by itself? Like, you know, and so, okay, I, and if you hear like the, the, the lessons are out there, they're not, they're not secret. Like, you know, the first one everyone always says is like perseverance and grit. Like that's very clear. If you listen to anyone who's done anything worthwhile, that will be a core part of their story. So I'm like, all right, Oh, like, I guess I gotta go do that. Like, let me figure out how to get good at that. And then just tons of iterations all the way, you know, and there's like smaller lessons about, you know, how do you sell, how do you inspire, how do you have a vision, how do you spend time with customers and on all of that sort of stuff. I remember I read this one book called Talent Is Overrated, but I read it right as I was graduating college and that was incredibly influential in my thinking. And it's based on this famous, Harvard Business School case study where they looked at the elements of world-class performance across a lot of different fields. Like, so they looked at, okay, if you're a Nobel Prize winner or if you're a top athlete or you're an entertainer or you're a very successful business person, 3 things, what do you have in common? Yes. Yeah. So the 3 things are deliberate practice. You know, you've applied 10,000 hours on a particular craft, expert coaching. So you get coached by people who are really good. It's not enough to just spend enough time. You have to get coached. And the third one, and I thought this one was underrated, is enthusiastic family support. And what that means is, okay, the people, you know, your family in your life, it wants to help you be successful at whatever endeavor. And so I'm like, okay, cool, how do I set up my life to go get all three? And so on the time one, it was just a question of, okay, if I set myself up to work at this long enough, I'll probably end up figuring something out. For the expert coaching around, it's like, okay, come to Silicon Valley and just be around people who are really good at this and get advice from them. And there's so many different folks. And, you know, I can talk about here who have, who Amplitude would not exist today if not for their investment in me.

Is Matt one of them?

Matt Huang was like my very first one, you know, just incredible. Like in terms of he had come out to do a company a few years before me and he just out of the goodness of wanting to help other founders invested countless hours into just giving me advice on applying to YC and building the company and recruiting other people and building a business and all sorts of stuff. You know, and then there was others over time, like there's one Mitch Morando that helped me think about how to sell to customers. There's Eric Vischerio, one of our current board members. I've learned the most from what it means to be a great CEO over the last 10 years. And so like, yeah, putting yourself in an ecosystem environment, and I'm incredibly indebted to all these folks. You know, they, a lot of them had really no reason to help me. And so I'm just very grateful for their help and support. The last one is enthusiastic family support. And this one's actually very important. And I find that in terms of deliberately setting up your life most people don't do this one with intentionality. And what I mean by that is that there's a lot of family circumstances that you don't choose, but there are some that you do. As an example, like, I swore off dating for a bunch of years because— was this in college or after college? After college, because every person was like, hey, you're like too distracted on this thing. And like, you know, it's just, you know, not enough time for the relationship. And it's like, all right, well, like, that's fine. Like, I'm not— I'm like focused on this thing right now. And then it was only, I was lucky enough to meet my current wife, Anne, because she was very persistent. And I told her early on, like, hey, I really care about this thing succeeding. And so you have to be okay with that too. She was incredibly gracious and supportive of that. And so that happened to work out very, you know, and I was like, hey, look, I'm willing to compromise like anything else, but just, I gotta be able to do this. Yeah, intentionally choosing your, your, as much of your family and life setup as you can so that it can support it. Because, you know, if you have other stuff you're dealing with, it's hard. Look, and I won't I don't glamorize it. It's actually incredible. It's hard on your family, especially in the early days before your financial resources or other stuff. And your brain is like 120% dedicated to this thing. And there's some very real, yeah, there's very real trade-offs where you just can't spend as much time as a typical person on your family. And so, and you have to create a setup, a family setup where your partner's okay with that. And frankly, most people aren't and shouldn't be 'cause it's not a good family setup 'cause it's very unstable. It has a lot of gravity. And so it detracts from a lot of stuff you might want to do otherwise in life. And so it's not a good life setup. But if your goal is to be world-class at this one thing, then that's the trade. That's part of the trade you have to make. And so I think a lot of people go through life not conscious, not willing to admit this trade.

Before this period of your life, you were at DRW and then you left. And then story to be told, you were in Curtis's apartment. Yes. And further story, you would play video games for some of the day and you'd code stuff before you came back from work. And there's this period where you also started a company that got into the YC, didn't really do too well eventually. That led to Amplitude, which we'll talk about, but touch a bit more on that little maybe 12-month period. And to quote, you also had said back in 2011, I wasn't sure if I could become an entrepreneur.

It was 2.5 years honestly, where before we had anything where we showed success. I was in high-frequency trading, very prestigious job, highly paid, recognized, working around really high-quality people who invest a lot in you as a person. I actually feel for DRW because they had put a lot into me as an individual, and I ended up leaving, you know, just under a year into it to go build a company because that's what I wanted to do. To top on this, the family, on the family side, you know, my mom, Chinese. And so very common to compare with her cousins about, well, how much is your son making? You know, does he have a car? Does he have an apartment? You know, you know, how, yeah, you know, how successful is he? You know, what were his grades? Blah, blah, blah, blah. So you go from being able to have my mom brag to all of her relatives how great her son is doing to like nothing. It's like, oh, well, he's, you know, just hanging out on the, you know, working on a company. You go from having an environment that's very clear what success looks like and a lot of support and help to help you achieve it to nothing. Zero, zero. There's no feedback. And in fact, any feedback you're getting is just your shit. Like, 'cause like nobody cares about using your product. Nobody wants to help you. Like there's nothing to speak of. And I didn't have anyone to work with. And so I like spiraled frankly a little bit. So I moved out to California in March or April of 2011. And was working. Curtis was still full-time at Google at that point, and I had just played StarCraft. I like wake up at like noon and I play StarCraft for a few hours. StarCraft II had just come out at the time and I play that for a few hours and then 4:00 PM would come around and then Curtis was coming home at like 5:30. So I'm like, man, I better show him I've actually like worked on some stuff because I want him to leave Google and like come join me. And so I work on stuff for like an hour and a half and he'd come home and I'd be like, look at all the amazing stuff I did today. Try to hype it up. And then we'd work together for a few hours and then he'd go to sleep and I'd stay up till like 2:00 AM playing StarCraft again. And it was just day in, day out and it was brutal. And I hardly had any friends in California. The only folks I had friends were folks that Curtis knew and then didn't have a car for a little bit, but we eventually got that sorted. And so it was very, very disorienting for the first few months. Luckily Curtis did end up leaving after he came up on his year mark at Google and then we started just cranking together. At that point, I had studied the success of a lot of startups, and one of the things that was very clear to me was that stood out very deeply was persistence. Almost every successful company had a point that was about a year or a year and a half in whereby, whereby all rights, they should have given up, but for whatever reason they didn't and they kept going. That then led to whatever success they had. And so what I said to Curtis was like, look, we've got to be able to do this for at least 2 years no matter what. You know, after that we can reevaluate, but like we have to stay hardcore committed. So we did our first thing, Sonolight. We picked this technology, voice recognition, that was just at the edge of we thought maybe being possible. We created like a background listening app where your phone would listen to you while I was asleep. Now it's more common. They still haven't cracked the UI, but now it's more common. But it didn't exist when we had created it. Did Demo Day, actually had some really good press come out of Demo Day, but then nobody wanted to invest in us and almost nobody. And the— we were convinced it wasn't going to work. It was probably going to be a long grind. So we shut that down after about almost a year working on it and ended up coming on to Amplitude. And what was good, at least about that point, was that given what we had talked about doing it 2 years no matter what, it was like no question we're going to continue. A lot of teams would break apart and kind of go back to doing something else at that point. But we're like, no, no, no, we want to see this thing through. And so we ended up starting Amplitude out of that. And it was a good year and a half before it was clear Amplitude was going to be successful. So we were just begging anyone to use the product who would talk to us. We'd develop a whole bunch ourselves. Then eventually we started, whole long story, but we ended up realizing, hey, we actually had to focus on people who were willing to pay us money and charge them.

Was this some of Matt's impact as a mentor? Somebody had told you this.

This was actually Mitch Morando, this guy named Mitch who who has helped out so many amazing teams in the Valley, very underrated individual. And he loves working with hardcore engineers who are looking to learn how to build a business. One of our other companies we knew, Sensor Tower, had been working with him and we're like, okay, hey Matt, I remember just going up to him one day and like, Mitch, I want to work with you, teach me how to do sales. I want to figure this thing out. I want to be successful. And he's like, whoa, whoa, whoa, slow down. Let's get to know each other first. And then he would start to work with us weekly and he would just beat me up every week being like, what's the customer pain? And I'm like, well, they want some charts. He's like, Spenser, that's not a customer pain. Go back and get me the customer pain. So I'd go meet with them again and I'd be like, okay, well, why do you want some charts? What's painful about that? You know, and you gimme all these tricks. He'd be like, okay, yeah, rate this pain on a scale of 1 to 10. And eventually I learned how to become a seller. And then we started rocketing up. And then we had a Jeffrey as a third co-founder at that point. We grew from $0 to $1 million in ARR in 9 months. And we were kind of off to the races.

Story where I think Super Lucky Casino gives you the first $1,000 show.

Oh yeah, it was so funny. So I remember it was me and our first employee, Alan, and we went to pitch this co-founder, CTO, Brett, and kind of demo our software. And halfway through, I think Alan's pen exploded in his pocket and his hand was just covered in the ink. And I look over at him, I'm like, what the fuck are you doing? He's like, oh, sorry, it like exploded. I need to like, can I go use your bathroom? So I'm like, all right, this is like not off to a good start. Brett was great about it. He just laughed and we kind of went on talking through it. So we go through the entire pitch and we get to the end of the pitch. And I thought at that point I was going to have to beg him to use it. But he actually responds with me a question I'd never heard up to that point, which was, how much does the software cost? And I'm like, I'm like, wow, I have never been asked that question before in my entire life. This guy wants to buy some software. That's crazy. Wow. Okay, I got to come up with a good response to this. And so the number I had in my head was $50 a month because that's what you paid for SaaS. It was just like no rhyme or reason. It's just like, that's what, you know, you pay for early-stage SaaS company. But I was like, you know what? I'd read a bunch of Pat O'Leaven's advice and he's like, charge more. So I'm like, okay, let me What's the biggest number I can reasonably think of in this moment? So I'm like, all right, let me double that from $50 a month to $100 a month. That's a pretty big number. And then right before I said $100, I'm like, no, no, no, let's do like 10 times that. So let's go to $1,000 a month. So I was like, $1,000 a month, which is as much confidence as I could muster in that moment. And to my absolute shock, he was like, wow, that's so cheap. I'd love to buy it. And I'm like, what? I was like, this is crazy. And in that moment, all of my dreams of like building and selling software, they were fulfilled. I'm like, look, if we're not successful, I at least got someone somewhere to buy something I'd built. This is an incredible moment. This is so amazing. And so yeah, I was, that was, and then he ended up being a really great customer for a bunch of years. And yeah, I think they're still a customer with us. The company's gone through a number of changes in ownership, but they ended up, you know, giving us a bunch of great feedback in the early days. And Brett was incredibly helpful. He put me in touch with a lot of other, he was an ex-Zinga person and he put me in touch with a lot of other ex-Zynga people.

I guess Amplitude from there grew quite meaningfully and obviously it's a great company, but are there any stories that most people don't know? Any stories of you maybe doing the first sale, the second sale, any of these unheard stories that paint a true picture into what it was actually like to grow a company?

Yeah, I mean, look, I'll tell you, I mean, if I look at that first customer cohort, almost all of them churned over the next few years. And so in some ways in the early days you were building on quicksand because it's like, okay, you're growing a lot and there's demand for what you're doing, but your customers, if nobody's sticking around for the long term, they'd either go out of business or have to reduce costs significantly. I remember there's one company, you remember QuizUp? A little bit. There's an app that competed at a trivia game. They were huge on us. That was our first $100,000 customer and it was great. But then eventually the company went out of business and shut down and just I'm just like, fuck, like, you know, I'm like, you're like, okay, are you really building successfully? You know, are you really going to be able to build a successful business with such a massive, massive churn in terms of what you're doing? So that was brutal. I mean, another time was we went down for an entire week back at the start of 2016. You know, we're very aggressive in terms of our innovation. And so we accidentally ran this one script in production that should have been not run where it like cleared a bunch of metadata tables. And so this one metadata table that does user ID mapping got completely nuked. And so all of our charts literally didn't work for a week. Oh man. Remember, people were freaking out and, you know, some of you were like, oh, you should find a new job. Or like, hey, is this going to go really bad? And all this awful stuff. At the time, there was nothing to do except like, okay, we have to go rebuild this, this table and like redo it and get it right because like we have to be usable. And we thought like all these customers were going to churn out and leave us. And just, yeah, but luckily not, not a single one did.

What did your parents say at this time?

There was kind of really two points in time. There was pre-2014 where like nothing was successful and nothing was happening, and then there was like 2014 onwards where we were just kind of growing up like this. You know, my parents, I, I like, I didn't worry too much about— I was always, I always knew I was going to go figure out what I wanted to do, and I wasn't too worried about what they had thought I was just very focused on like, hey, let me learn and figure this out, figure out this thing and try to build and make it successful. And I kind of emotionally accepted that this failure and struggle was a big part of the journey on it. Interesting.

And so I guess now touch a bit more on not the dark days, but when it started really going up into the right, who are the core customers and how did you change, I guess, as a salesperson? I think the core change in your maybe transformation as somebody who was a really good engineer to now also a really good salesperson?

I don't know that I'm good, but the sales piece, I was very lucky to get Mitch's coaching for like a year and a half. And that made me from like not know anything to at least have a foundation on the basics. And then from there it's just practice and frankly confidence in yourself from seeing it enough times that then it becomes management and hiring. Hiring, you know, most folks is actually, you know, there's good advice on it. Hiring execs where you're hiring something, someone who's supposed to be more of an expert than you at something that is just brutal. For your own psychology because it's like, okay, I was supposed to be the— I'm in this position as a leader because I'm best at this thing. But now I have all these people that have skill sets that outpace me in different ways, not just on the technical side in terms of like, oh, well, they know how to build and run a sales process, but— or scale a team. It's like, but on the leadership side, you know, more inspiring as leaders, you know, higher emotional intelligence, all sorts of stuff. And so it was that was very disorienting. I remember I sent this note. We had the first real executive that joined us. It was so disorienting for me. I was like, man, should I even be in this leadership role anymore? Remember, I have this note that I sent to Y Combinator team at the time being like, yeah, it's kind of causing me to question. It's like, am I— like, should I be leading? Am I relevant? What's my value to the company in the role? And actually, Sam Altman at the time, this was when he was just taking over from Paul Graham, but replied and said, said, you know, hey, this is actually a very normal part of the process and like you'll get through it over the next few weeks and it'll be fine. And so honestly, it's just kind of a blur because like you're just trying to keep up with the month ahead of you or the quarter ahead of you in order to like keep scaling this thing that where the market's kind of pulling it out of you.

Did you spend time with Sam back then? I did.

Yeah, I was very lucky. I was very lucky. I'll tell you this funny story with him. We had gotten from $0 to $1 million in 9 months and it was about November-ish. And so I was like, you know, okay, well, you know, everyone says fundraising cycle, you know, you don't want to try to do it during Thanksgiving. So let me just wait till next year to do it. And so I was like emailing the YC folks being like, hey, we're, you know, we've had this growth, but like, I'm kind of tired. Let me just like take a breather because it's been like really intense for the last year and let me start fundraising in January. And Sam was like, what are you talking about? Like, you know, like you need to go now. And I started arguing with him like stupidly. So he's like, all right, look, just just let's meet me at dinner and like we'll talk about this more. So I go to dinner with him and he asked me, he's like, Spenser, why are you not going to fundraise right now? Like you've been waiting for this forever. Like you should go right now. Well, you know, it's, let's do a, I'll be more ready in January and you know, it's a little too tight with the end of the year and like all these kind of bullshit reasons about like, hey, I just didn't, I was tired, you know, AKA I'm tired. And he looks me in the face and he's like, Spencer, stop being a pussy and go raise now. And I'm like, okay, okay, okay, okay, okay. So like I went out to raise and it was very successful and we actually ended up closing the round on New Year's Eve on the 31st. Was that your Series A? Yeah, this was a Series A. We, yeah. And this is, I met Benchmark and Eric and he acted incredibly quickly. I had no idea how exceptional they were at the time actually. But they were, you know, he was, yeah, I was very, very lucky to get him on the board and investing in our Series A. And you know, that was the start of a very, very great partnership.

What's a bit of the story from there to now IPO?

What happens then is you start to see the organization, your job as founder shifts to hiring the best talent you can and building the executive team and scaling the organization. And so it becomes a lot of like recruiting and talent evaluation and trying to get good people on the team and trying to figure out how to scale this, scale the thing. And, you know, we've been through through 3 different executives. This is the 3rd executive team that we're on at Amplitude now. There's a lot of just rallying the company. Yeah, it's crazy. I'm trying to think too what even touch on. It's so funny, like in the moment you don't really think, you're just like kind of in do mode, like indefinitely. And you know, you kind of fast forward 13 years later and you know, now you're here on the thing. So it's weird to think about.

After you IPO'd via direct listing, you had told the firm that this was Project Alpha. You'd essentially just started. Was that your general heuristic of how you went about things and why did you say that? What was a bit of the culture at Vamply at that time?

It's very important. I had seen so many companies get lost after going public. And so a very core lesson was Marketo actually, and Phil Fernandez built an incredible business at so many different levels, but had talked about the public listing as kind the finish point. It's like where they wanted to drive the company to. And when they actually got there and got past it, it was actually very disorienting for the company because it was not clear what was next. And so we spent a very long time beating into the organization that like this was just a tool. And frankly, I should have internalized that message more deeply as well. But that's allowed us to be really clear that like, you know, as we're going on to bigger and bigger things, we're still very, very early in what we're doing because, you know, markets are big and long. And yeah, we're, you know, you look at a $300 million revenue business and thousands of customers, you're like, wow, that's, you know, big. And it's like, no, in a lot of ways, in some ways, yes, relative to the early stage it is big, but relative to, you know, the opportunity you're going after, you want to choose a mission that's much, much bigger and broader. It's small.

Did you ever celebrate? Did you buy a car? Did you do anything that was—

Yeah, we probably honestly had too many celebrations at the listing in retrospect. Got too distracted from the core of the business. Yeah. Like I'm not a car person, but—

Did you reflect back on that maybe in that moment and look back and kind of were you surprised? Were you certain this was going to happen because you had—

I'm shocked. I'm shocked that it happened. The bet I made was like, hey, if I study companies and I mimic what it is like to be a great founder and great company builder, how far can that take you? Become the ultimate founder. You set up your life in a way to do it and you just go deep at heart in the problem.. And I thought what would happen is we'd maybe have some success and that would be good, but there'd probably be a lot of things I would've missed in that process. And, you know, I'd be like, yeah, I want to redo X, Y, and Z if I were to do it over again. But it's turned out, has turned out way beyond anything I could have ever expected. No question on it. Yeah. I mean, I thought I'd be like, I would've been happy just leading a small team of a small business of, you know, if we had ever gotten to $1 million, that would've been success, you know, and leading a small team to go execute on that. But, we're very lucky that we got way beyond it.

What does it seem like everyone else is mysteriously bad at?

Maybe I'd say it's risk-taking. Now it's much more accepted to do, start a company and try to build something with technology than it was 15 years ago. But I remember I had mapped it out and I'm like, if I do this, it's not a guarantee, but it's a very high likelihood of success. And I remember just having all these backups. It's like, well, if this doesn't work out, I I can go get a job somewhere else, or I can, you know, go back to school, or I can do, you know, I can do lots of different things. Like, I had read Hacker News and Paul Graham's essays and a lot about the startup thing, but the difference between all of those folks that he talked about was just like whether you choose to do it. Just choosing to do it puts you ahead of way, way, way many other people. The risk-taking, yeah, I think people are just very bad at embracing things that are risky.

Why do you think that is? I would argue it's probably rooted in a function of caring what people think about you.

For sure the social pressure matters a bunch and like, you know, a lot of MIT engineers would talk about wanting to go build a company, but I remember talking to like 20 different people at MIT about it. Almost all of them ended up opting for a much safer job because it's less risky and because it's like, you know, it's socially accepted and it's not clear what the other path is. You know, it's like this thing in investing, It's like, it's not so much being right is that hard, but it's being right when everyone else thinks you're wrong. Yeah, and so it's important to create tricks for yourself to do it. One of the most funny ones I actually came across, if you look at Elon, Elon's like a classic example of this where the guy is so fucking extreme in his beliefs and is willing to be like very ostracized for it. I remember he was interviewed once a bunch of years ago being like, oh yeah, who's your hero? Who do you aspire? Who do you look up to? To? You know what he said? He said Kanye West. And I'm like, oh my God, that is fucking, that's a genius fucking response.

Because like Kanye, that makes a lot of sense. Yeah.

So the willingness to take risks and not like, yeah, to take risks, it's underrated. It's very underrated.

And maybe the last question to end, which honestly I'm kind of curious about, is what's some advice that you're happy you ignored?

A lot of people told me not to get into data analytics. That's for sure. It's a crowded market. Hard to build a company around scale. Remember there's this one investor who I won't name who it was, but they were a top investor who was like, yeah, we love you guys as founders and we want to invest in you guys, but we hate your idea.

It's a classic Airbnb story though of like, oh, this idea, the market's not big enough.

It caused me a little bit of pause because I was like, these guys know what they're talking about. They've obviously seen way more successful companies than us, but do we believe in what we're doing? Luckily that time we did and we saw it through. The funny part about that though, and we've obviously gone on to build something great, but the funny part about that is there were times where that advice was actually right. I remember the first time we applied to Y Combinator, they actually said the same thing. And this was before Sonalight. We applied with this outsourcing website and they sent us a message back being like, hey, we like you guys, but we hate your idea. We actually should have been like, Yeah, you know, you guys, that's worthwhile listening to. And it's, it's, yeah, we should change what we're doing on the basis of that. So it's, it's one of these things that's so hard to, you know, you're the CEO of your own life and so you got to make the call ultimately with what you're comfortable with doing and what you want to do and, and not. And that's one of those things that's so hard to, to know. It's like if you're right or not. One of the ways, if it's a close call, is just, you know, optimize for the way that you're going to learn more. It's hard. Like, I mean, I'll tell you both sides of it. Like with this, you know, we've been compounding this for 13 years, and I hope to be compounding along into the future, you know. And so I think that is underrated. I think a lot of entrepreneurs, even 10 years in, quit and go and spend the rest of their careers trying to recapture a fraction of that subsequent success. But, you know, there, yeah, there are entrepreneurs that, that work too long on something too. So that's not one of these easy— that's not ones that's, that's easy to say, you know, who's right, who's wrong ever on