Spenser Skates: How Perseverance Paid Off for Amplitude

almost every single company had gotten to a point where if you were to look at it from a rational standpoint, you're like, yeah, probably you should probably just quit now because you guys don't know what you're doing. But for whatever reason, they didn't. The clear sign to me was that if you wanted to be in that group that were successful, if you just stuck through that moment, your chances of being successful would go way up.

That's Spenser Skates, founder and CEO of Amplitude. Amplitude has done more than anyone to make user behavior legible so product teams can stop guessing at product decisions. This is Mike Maples Jr.

of Floodgate, and it's go time with Spenser Skates.

This is Mike Maples Jr., and welcome to the Pattern Breakers podcast, where we explore why some founders radically change the future and how they stand apart. Together, we'll learn about the counterintuitive mindsets and actions behind their remarkable success. Brace yourself for a world where chaos is welcome, naysayers are often a positive signal, and movements galvanize misfits who transform the impossible to the inevitable. When Amplitude launched, the analytics market looked crowded. And for over a year there was essentially no traction. By conventional thinking, the odds were bad. But Spenser prioritized truth-seeking over narratives. He studied past YC outcomes and saw a simple rule: most companies die before they even learn enough to make something that people want. If you survive long enough, probability shifts. 2 years was his threshold. So Spenser and his co-founders determined to stay alive past that milestone. They learned how to identify the customers who truly valued Amplitude's advantage. They developed the skills they needed one day at a time. And ultimately, their learn-it-all mindset and grit led not just to survival, but a publicly traded company valued in the billions.

Let's talk to them. Spenser Skates, welcome to the show.

Fantastic to be here. Good to see you again.

Yeah, likewise. So before we jump into Amplitude, there was a company before that called Sonolite that maybe not everybody knows about. It kind of frames the origin story well in a lot of different ways. So I was hoping that you could just share what Sonolite was What was up with that? Why did you pivot, and how did it lead you to Amplitude?

So before we did Amplitude, uh, so we had Sonolight, which was a voice recognition app, uh, and it was like a version of Siri for Android phones before Siri came out. It was actually funny, we did, uh, the Y Combinator Winter 2012 batch, and in the middle of the batch Siri launched. And so during demo day, we called ourselves Siri on steroids, which really resonated with a lot of the press. We had this really cool demo where I took my phone and then I put it into my jacket pocket, and then I had a conversation with my phone while I was on stage, and it blew the audience away because it was like I was doing a magic trick in front of all these investors at YC Demo Day. But the funny part was that the product, it wasn't that great. It had a really cool demo, We had a little bit of traction. There were something like a few hundred thousand downloads, so somebody was using it, which was cool. But we had a really hard time retaining users, and the quality of the voice recognition technology was just not there. Even though we had this incredible demo day, we weren't able to fundraise after. I was convinced there were 3 angels that put money into us at the time, and I remember all 3 of them. I was convinced that the only reason that they invested in us, it was because they were investing in all the lame companies in the YC batch, and that was their selection criteria. So we did that. Demo day was in March. By the time we got to May, we were like, all right, we should probably shut this thing down because we could keep working on it, but it's going to be a long, hard, grindy road. And we're not particularly passionate about this technology and we don't know if this is going to be successful. So let's, let's go try to find something else. Then that led us to— we had spent all this time building our own analytics in-house. We spent like a third of our time trying to understand what users were doing in the product because it was so obvious to us this is the right way to look at and build products. And so that eventually led to Amplitude, and we started that in June of 2012.

Now I've heard varying rumors about the early days of Amplitude. So like one, one thing that I've heard attributed to you is that part of your goal was to survive long enough. Like there's kind of, um, there's kind of this heuristic that I've heard some founders suggest, which is if, if you survive long enough, you just keep surviving and eventually something happens. And like a lot of companies fail because they decide to quit rather than just keep persisting. And so to what degree is that rumor true?

Oh, so that, that was completely how we thought about it. So before even starting, uh, Sonolight, I didn't even know, like I was just some college kid. We graduated from, from MIT in 2010, uh, me and my co-founder Curtis, and I wanted to know whether I was capable of starting a company. And so I did this research where I looked at the Y Combinator batch for 2 years before.. And I was looking at like, okay, 2 years later, how many are successful? And it was like, I think a third kind of had gone on to some clear success. A third had gone on to shut down and fail. And then a third were kind of, you couldn't tell they were still out there, but it wasn't clear how well they were doing. And so I started to get, wanting to get really serious about studying this. And so I just read all these stories. I read Jessica Livingston's Founders at Work. I don't know if you've come across it before, but just incredible set of stories from the early days of entrepreneurs. I read another one that was called Startups Open Source, and one of the really clear themes that stuck out— almost every single company had gotten to a point where from a rational standpoint, they should have quit. And this was normally 6 months, 9 months, a year into the business. They weren't making progress. They didn't have traction. If you were to look at it from a rational standpoint, you're like, yeah, probably you should probably just quit now because you guys don't know what you're doing. But for whatever reason they didn't. The clear sign to me was that if you wanted to be in that group that were successful, if you just stuck through that moment, your chances of being successful would go way up. It was so crazy how our experience bore that out because watching our Y Combinator batch, after not getting traction in the batch, they'd kind of go back to their day jobs. Like a lot of them, or the co-founders would fight and break up. Whereas for me and Curtis, it was like we get, you know, we do YC, we have this awesome cool demo, we get all this press, but then, you know, we don't get any investors and we see that we can't really retain our users. And it was no question to us that we were going to stick it out and work on something else. It was just a question of what. So we spent the, you know, that May to June period in 2012 just looking at lots of different ideas and figuring out what we wanted to work on. And eventually coming on the analytics thing. Some ups and downs, but ended up, the whole thing ended up working out. But the important part was that there was no question in our minds that we were gonna stick after this problem. And even if the first thing we don't work on with Sonalight doesn't turn out, we will be more formidable and we'll go after it again.

How did the Sonalight idea lead you to the idea for Amplitude? I mean, it sounds like that your experience in measuring the success of the product somewhat led you there, but were there other factors that led you to the idea for Amplitude?

Yeah, the biggest thing was it was so obvious to us this is how you should build product. You should look at the data of how people are using it because there's nothing more powerful, right? People say, you know, talk is cheap, but if you want to know what someone really cares about, look at what they do. We had this one question, which was how important was the accuracy of the voice recognition to the long-term retention. So if you came into the product, you know, it, it asked you, hey, who do you want to text? And then you say a name, and then, you know, do you have a successful match against your contact book on that first prompt, or does it fail and you have to redo it? We were like, all right, what do we do? Let's look at the data. So we ended up spending all this time collecting data and building a system that could— we could understand and visualize these questions. It turns out accuracy of the voice recognition is incredibly important. If you had a successful first recognition event, your chance of retaining was double than if you didn't. So massively impactful. So that means, hey, if you make the recognition 1% more accurate, you're going to have 1% more retention, or if it's 10% more accurate, you're going to have 10%. So it actually matters a lot if you put energy into this thing. That ended up leading us to realize that, okay, we can only improve the accuracy of this thing so much and we can't really get it to the point, where it is going to be good enough retention, it's going to be a usable product. And so, you know, funnily enough, it was kind of this existential question and we answered, okay, this is actually not a viable product and a viable business, but we realized a lot of other people are going to want to know the same thing.

Huh.

And, and I guess there were other tools at the time, right? You had Google Analytics and you had Flurry and you had Mixpanel, all these guys. Uh, what was it that they weren't able to do that you thought was necessary to do? Was it literally this product instrumentation?

Relative to retention? So they weren't able to do that, but it was even more— it was incredibly crowded. So I, I'll list off, you know, the ones we tried. So Google Analytics, there was Adobe, which was the enterprise guys, there was Flurry, which was big on mobile, there was Appsalar, which was mobile attribution, there's Localytics, uh, there was Mixpanel, uh, there was Kissmetrics, uh, there was Keen, which was focused on developers. Like, the lists just go on and on and on. There's like 30-something-odd competitors, and you're like, all right, do you really think you're going to be smarter than all these guys? Well, the one thing we saw was that being able to look at the user on the basis of behavior and say, is this a good behavior, is this a bad, none of these other guys were able to do that. And so we said, okay, we at least know we can build that, and that's different enough, and we know that's something our batchmates valued. I mean, we would show, you know, when we talk to our batchmates in Y Combinator, we'd show them these analyses we did on voice recognition accuracy, and they're like, "Holy shit, this is way more advanced than anything we're doing. Can we get that? Your voice recognition looks kind of crappy, but can we get that analytics?" We were also a bunch of algorithms guys. Curtis and I won MIT's largest programming competition, Battlecode, and one of the key things is, okay, can you create a distributed system and write algorithms at scale? Analytics was so much more of an attractive problem to us than voice recognition, because in analytics there's like a clear right answer and it's just, can you do it efficiently and fast? And whereas like probabilistic problems, it's like, God help you.

So one of the things I'm wondering about so far in this, Spenser, is, um, in your first product, in Sonolight, even though it didn't work out, you had a demo that got instant attention by a whole lot of people quickly. And it sounds like that rhymes a little bit with the early days of Amplitude. You could show somebody something and very quickly they would have the, you know, your words, right? Holy shit moment and say, wow, you know, I need that. Can you give that to me? Is that a fair assessment that, you know, when you've done these products, that you've tried to be able to demonstrate the advantage really quickly so that people could instantly see what you're talking about and why it matters and why they should care?

That's a good, I've never been asked that before, Mike. That's a really good question. I mean, for sure, Sonalight had that wow factor to the demo. With Amplitude, like this is like a data-intensive nerdy product. And so the average person would be like, okay, you're showing a bunch of graphs, who cares? But for people who were really into data, they got it when you showed them. I remember one of our early groups of customers was a bunch of ex-Zynga product managers that had gone on to start their own companies. They were so used to having this stuff and they had believed in the same way of building product that we did. When they saw it, they were like, "Oh, okay, yes, great, sign me up for it." One of the mistakes we actually made in the early days of Amplitude, it was a good year and a half before we got real traction. We didn't have that wow moment early on, and it was a real grind to get some of the basics together. The mistake we made frankly was we tried to convince a lot of companies that were not as passionate about data as we were to use what we were doing, and we were basically begging them to use it for free. It turns out, out of the first 20 or so companies that were trying it out, none of them ended up paying or becoming customers of ours long-term. It took us a little time to figure out the right group of people that did have that wow moment with Amplitude.

So, and what was it about the early adopter successful believers that was different?

Yeah, so, so this, the, the first one is this guy named Brett Terrell, who's this, who is the CTO and co-founder of this company called Super Lucky Casino. So they're, they're a mobile slots game, and he had worked at Zynga as a product leader before, and he had left to start his own mobile app company. And he just had this big gap where he was expecting— he knew this was the right way to build a product with data, but he didn't have anything that could. He was trying to use Flurry and Google Analytics and trying to cobble it together himself. And so I remember this was July of 2013, I think, where we came in, we do the demo to him. We kind of— he asked some questions. We get to the end of the session, and at the end of the session, he's like, how much does this cost? And I was shocked to hear that question because I'm like, like, what? Like, how much does what this cost? Oh, I— because in my head, I was like, oh, I was, I was gonna beg you to use this for free. But I was like, all right, let's, let's test this guy out. Let's see how much he could, he could possibly pay. And so I was like, all right, what does SaaS cost? And I'm like, well, $50 a month. But I'm like, you know what? Like they always say, charge more, ask for more money. So I'm like, let me think of a bigger number than 50. What's bigger than 50? Well, if you double that, 100. 100 is bigger than 50, right, Mike? Yep. I'm like, then right before I say 100, I'm like, no, no, no, no, I gotta put an extra zero. I'm gonna say $1,000. So I was like, $1,000 a month, which is as much confidence as I could say to him. And to my absolute surprise, he was like, wow. That's so cheap. I really want this. Let's do it. And I'm like, oh my fucking God, this guy actually wants to pay me for software. Like, my mind is blown in this moment. What's happening? Yeah, it was the first year of Amplitude was not like that at all. That took a while to get to that point and finally find someone like Brett.

So it's interesting.

One of the, one of the things I've often seen with the successful startups is they'll have an insight. So like, let's say that your insight had something to do with not just understanding growth accounting, but understanding how product interaction impacts retention, right? And the success of the product. That's more than just cohort analysis and churn and upsell and resurrection ARR and all the stuff everybody talks about, right? But, but there's a set of people who are prepared to see your new way of seeing, and then there's kind of everybody else. Yeah. And, you know, so I like to say in product market fit, we try to ask what can we uniquely offer that people are desperate for? And quite often the insight precedes finding the desperate. Like you had a new point of view about what analytics should do, but a whole bunch of people are like, yeah, whatever. But there's a few people are like, where have you been all my life? Oh my gosh, $1,000, that's so cheap. And so what did you learn about, like, apart from this guy who's doing Vegas gambling stuff, who were the early desperate customers and why do you think that was?

Yeah, so, so there was a lot of these Zynga product managers, like Brett was one, Siki Chen was another at HeyGen, uh, or Hey Labs then. Uh, there was another one, Shane, at this company called The Hunt. To us, it was so obvious this was the right way to build. You look at what users do and then you make a better product on the basis of that. That tells you so much more than you could from any other way of building a product. It was just about finding that other group, tribe of people that had that same outlook. I think the biggest surprise to me was how everyone would give lip service to data. They'd say, yeah, data is incredibly important. Of course, we're data-driven. Of course, we want a analytics and to understand this, but the problem was just too hard to deal with. So they weren't willing to spend money, they weren't willing to spend time trying to figure this out, um, they weren't willing to use a crappy tool that, you know, they'd never heard of that just started where they were the first customer. We just had to keep looking because we knew the future was going to be this way. And eventually we did find our tribe of people that, that had this crazy belief and so much so that they were willing to bet on us. One of my mistakes was just spending a lot too much time with people. You know, if you know Crossing the Chasm, there's the innovators and then there's early adopters and then there's the early majority. I spent a lot of time with like early majority people when really I should have just spent time in the really early days with the innovators. And if only 1 out of 1,000 companies is the right fit or even 1 out of 10,000, fine, so be it. Just Don't listen to those other 9,999. Like, just, just figure out how you can find that one that, that cares about it. And then eventually, you know, you start going through that curve. Like, I just couldn't imagine a future which it wasn't true that people would look at data for their product. And it's still kind of crazy to me today. Like, vast majority of companies, they pay lip service to it, but they're not doing it. And so from those early group of, of ex-Zynga product managers to like starting to become a more mainstream thing in technology companies to now we're starting to see traditional enterprises do it. I guess we're 13 years in at this point. We're still going through, we're still in the early days for the adoption of what we're doing, but that's okay. That's totally okay. Much better to have a group of people, a tiny group of people who would die for your product than to be lukewarm to everyone. That's which is, you know, as you know, it's just like you can, you'll, you'll fade out.

And so did you get a palpable sense ever things are really starting to work now? You know, was there, was there kind of a defining moment in your mind or was it more just like one day at a time just trying to figure things out until one day you come up for air and you're like, hey, this is starting to work?

So there was about a year and a half at Amplitude where it was, we were lost in the desert and didn't have any paying customers, didn't know how to sell, didn't know how to ask for money. And so we just build stuff and beg people to use it. And then at the start of 2014, two things changed. One is that we added our third co-founder, Jeffrey Wang, who joined us. And our ability to ship product went way up. I always have this thing where, Curtis is twice as good of an engineer as I am, and then Jeffrey is like twice as good as Curtis. So it's like, you know, 4x on me. And then I switched full-time. I was splitting my time between building the product and selling it, and I switched full-time to the selling of it. And I got a sales coach to help me because I didn't know which way was up. And he was like, oh, Spenser, you're wasting tons of time with all these people that are never going to buy. Let's focus on the few that really care about this product. So that happened at the start of 2014. We grew from zero to $1 million in ARR in 9 months, and we're kind of off to the races. And then raised our Series A, and then just, you know, things started compounding and growing like crazy from there.

And do you think you had natural sales skills and you just needed a little bit of coaching to unlock them, or do you think that your, your success is— maybe it's a story about how more people can be good at sales than they think?

I think a lot more people can be good at sales than they think. I think the impression of salespeople is like, it's a negative derogatory term in a lot of circles. But you look at the best salespeople today and they're leading, you know, they are leading companies and they are the leaders of the future. You know, you look at, say, Sam Altman, just incredible salesperson. He's a technologist for sure, but his real superpower is as a salesperson. You look at CEOs of any of the Fortune 500, they're all salespeople through and through. So you're selling your vision, you're selling your customers, you're selling, you know, people working at the company, you're recruiting more people, you're selling investors. And so, you know, the same skill in rallying people towards a vision and leadership is kind of the same. It has a lot of the same elements of skill. And a lot of people can do it if they put their minds to it. They just need a little bit of coaching. One of the actually Mike, one of the biggest mistakes I see a lot of great engineers get into is they think they learn it from a book because that's how they— a lot of them have learned how to be incredible engineers and programmers. They'll be like, well, you know, I learned Python by like going through the manual and, you know, testing stuff out. And they try to learn sales the same way. You're going to learn by like doing it and then getting a little bit of coaching from an expert.

That's— yeah, there's not some mental model Yeah, yeah.

There's a lot of fucking mental models. Like, there's, you know, every sales— you know, there's sales methodologies, med pick, you know, solution selling, SPIN selling, you know, an endless thing of these. But they're not— they're not how you learn how to be great at it. You learn how to be great by doing it and getting a little bit of coaching from an expert.

Uh, how did you get to know the guys over at Benchmark, and how did they— you know, what did they see in Amplitude, right? Obviously they're a pretty selective firm. And, uh, they don't just write checks for anybody. What do you think was the thing that captivated them?

We had started the Series A process and we had already gotten a bunch of term sheets from other firms, and I didn't even know who Benchmark was, candidly, at the time. I mean, you know, for those in the know, uh, you know, yeah, it's like one of the most legendary venture capital firms of all time. So I finally get an intro to Mitch Lasky at the time. He passes me to Eric Vischeria, their newest partner. And at that point, I had already gotten a term sheet, multiple term sheets, and we were close to signing on them. So I show up to the Benchmark offices, and this is when they were still on Market Street, and I came in 20 minutes late to my meeting with Eric, and I didn't even have my computer, and so I didn't have a deck to go through. And for whatever reason, I don't know why, I still don't know why this to this day, but Eric really loved what he saw in that meeting with me. Great, let's get you in front of the partners. I'm like, okay, but hey, this time just make sure to show up on time and bring a deck and everything and everything else. And in retrospect, I think Eric has a very particular type of entrepreneur he loves. I had a lunch with a bunch of his partners portfolio companies, a bunch of us were meeting up for lunch a few years back and it was clear, it was like we were all the same person, Uber nerds that somehow had started to try to grok the business side and really cared and passionately were competitive and wanted to win at building a successful business. So for whatever reason, he had just invested in Confluent, who was like, "Fuck it, okay, these guys are open source legends and I'm just some kid at MIT who doesn't know shit." But for whatever reason, he resonated with me in that moment.

And so the determination factor, you know, it sounds like he could kind of read into that. And then, you know, you've talked about your early days pivoting and saying, I'm going to outlast this for a few years at least. Is there anything from your childhood or just earlier in your life that would have suggested that you're a highly determined person?

Honestly, I think high tolerance for failure is probably the only thing. I didn't mind failing. And then you look at anyone who's achieved anything worthwhile and the story's the same, which is 50% of it is persistence, like just showing up and not quitting. And so you're like, okay, all right, well, I can do that. Just show up and not quit. And then I was like, all right, let me think about how I do that to the extreme. I did this exercise where it's like, okay, what's the ultimate founder look like? They'd be willing to go at it for a long period of time. They wouldn't have other commitments in their life, like whether family or debt or something other or hobbies that made up their life. They were incredibly frugal, so they were willing to work for very long periods of times with no pay. They didn't care about external validation. So one of the things, I have a Chinese mom, and so one of the things is you'll always compare with your relatives like, hey, what's your son doing? How much is he making? Does he have his own place? All that sort of stuff. So you're willing to go to be like, "Hey, parents, I don't care that you want me to go the validated path. I'm good with a different one." And same with peer pressure. Your friends are getting prestigious jobs at Google and banking and whatever. So yeah, I don't care about that. Anyway, so I create this archetype of persona and I'm like, "All right, let me just be that. And then let me give it at least 2 years and see where I come out on this thing." And it just, to me, that just goes to show, hey, if you're just willing to put in the work, um, over a very long period of time, you'll find some level of success. That was actually another thing, Mike, that I saw was that, um, it was very rare to have a person who had worked at least, you know, more than 2 years trying to build a company and not had it lead to something, whether it was they get acquihired, whether it was you know, another opportunity, like just by being there, you end up being in a very select group of people who haven't quit. And that means you have tenure of experience that's unique. And so you'll be able to figure out something, whether it's the next company or, you know, some other opportunity. And so that was like a really— it was like, okay, let me actually run that experiment on myself and see if, you know, just the persistence will see you through. Yeah.

And I think that most of the people that I work with and respect in this category of companies in seed and in Zero to One would probably argue that determination is the most important thing. If you could take all the factors, all of them, IQ, persuasiveness, all those things matter for sure. But I'd say if you had to pick one and only one, persistence, just determination, raw determination, And I look at the people who've been great, truly great. They all have that. You look at, say, Elon Musk, the guy just never backed down.

Oh, incredible. I mean, you know, he's been on the edge between greatness and utter destruction his entire life. So I just—

yeah, absolutely incredible. It's funny, when my dad was early in his career, you know, he was at IBM and later Microsoft. He studied the moon landing a lot and he was really interested in it. And there was, there was a study that was done where they said, you know, how in the world did they land a person on the moon in 1969 and bring them back safely? You know, HP hadn't even invented the pocket calculator yet. And they had this term that they called hot teams. They had to put an antenna on top of a mountain. Mountain, and there were no roads to the bottom of this mountain. And they're like, how are we going to get all these parts up on the top of this mountain? We're going to be behind the deadline. We need to talk to our manager. And everybody says, no, let's not talk to our manager. They'll just gum up the works. I'll just slow things down. We just got to find a way to do it. So somebody on the team says, who has the biggest helicopter in the entire world? And somebody does some research. They find out it's the US Navy. So they call up the US Navy. They say, hey, it's NASA. 'Can we borrow some of your really big helicopters? We need to make this antenna on top of a mountain.' And, you know, the Navy's like, 'Screw you, NASA. It's our helicopters.' And so the NASA person says, 'Hey, look, if we don't get that antenna on top of the mountain by this date, we're not going to land on the moon in the '60s by the end of the decade like JFK said we would.' And so then the Navy's like, 'How many do you need?' Right? So, so they flew all these parts in these helicopters up to the top of this mountain. And assembled the antenna. And, you know, the NASA moon landing was 1,000 examples of that. It wasn't some OKR thing. It wasn't, you know, and it was like what, what I learned from the hot teams concept was, you know, because some of these teams were 1,000x more productive than was expected. Just insane, right? And like what they— what the hot team concept suggests is that to be great, you have to believe that the goal is super important and you can make it happen. And like, without you, it may not happen. And so it's like those guys putting that antenna on top of that mountain, they're like, we— I may not get a bad performance review, right? It's not my fault. But like, we got to get this freaking antenna on top of this hill or we're not going to land on the moon. And that's job one, right? And it's like, I always remembered that example, you know, of, of just like the importance of having mission clarity and caring about what it is.

Absolutely. The importance of why, like you have to motivate everyone through the why. I'm still learning this as a CEO today. You know, one of my executives gave me feedback. Spenser, you're very focused on efficiency, decision, decision, decision, decision. You need to be focused more on effectiveness. And what he meant by that was if you start with that why and you're really clear about that, then people will come to the decisions on their own. The Navy will figure out like, oh yeah, I better help NASA out with this helicopter to put the antenna on the mountain. I remember thinking about this as a, when I was little, where does success in life come from? Is it a question of, hey, you have some certain set of attributes and whoever just happens to fall on the high end of the bell curve on those attributes does really well? Or is it, someone who can have the persistence to continually change themselves and move them up on the skillset on the bell curve. So eventually they get to the top and turns out second's way more important than the first one. It's very much about who you mold yourself into over time, which is just a function of the determination than it is the, hey, you're just born this particular way.

So what's that been like? You know, the job is obviously very different now than it was when you started. And, you know, as you point out, you have to change. I've noticed this in a lot of really good CEOs. Depending on what year you meet them, it's like they're a different person. I imagine if you met Mark Zuckerberg in 2005, he's a different guy than in 2011 and certainly today. How did you do that and what was that like? You know, did you enjoy that process or was it hard for you to do that?

It was hard. It's hard. You have to do it multiple times over the course. I mean, it's like you start out I was an engineer and I transformed into a salesperson, then I transformed into a manager, and then now it's like a large company executive. I'll say the— and so you're just like, I don't even recognize the— it's been 3 or 4 transformations. I don't even recognize myself anymore because you're just molded by this organization, this thing that you have to create. The hardest one is is the one I feel like I just went through, which is to large company executive. And it felt really, really bad, frankly, because a lot of things that made you great as a founder, you have to give up. And when you're a founder, you like make fun of these larger companies. It's like, well, the executives don't do any work and they don't know shit. And, you know, they're just playing their stupid status games and getting paid a lot to have nice shoes and give fancy speeches at an all-hands, like, who cares? And then you get there and then you realize like, okay, these are actually really important skills for running this thing. And then you have to become this thing that you hate. And so that was— and then give up a lot of the things that made you great as a founder. So let me give you a really simple example. As a founder, Leading by example from the front, it's a critical part of being an effective founder. So whatever the hardest problem is, you got to be there on the front lines trying to solve it yourself. Where you've got a really hard deal, you got some really gnarly engineering issue where like the system's down or there's some architecture question. You know, you're trying to make the viral video that like gets you the breakout record. Like, hey, you better be that you're trying to recruit the candidate that's impossible. You're trying to raise money like You're the guy or gal on the front lines leading the charge. Hopefully you get a crew of other people around you that can help you along the way, but you're on the front. You're very in the front. You take a lot of pride in that because no matter what the hard problem is, you're the person that will always try to solve it first. You get to a large organization, you can't do that anymore. It's not feasible because your work is done through other people. And so your job changes to instead of leading that charge to explaining the why to other people so they go take on that charge themselves because there's too much. There's customers having issues all over the place, there's product issues, there's like, hey, how do we get the awareness out there? There's recruiting, there's just nonstop, nonstop. When you're at, we're at, $335 million in revenue and about 800 people today. And so the surface area is just enormous. You just don't have the time. Like, you can't be effective in that way when you, when you are small. And so instead, you— I think a lot about how do you get leaders who are going to be able to lead from the front on all these different areas? How do you set them up for success? And how do you give them the right mission and the right why? And and enable them to succeed. You're constantly making judgments. Okay, this person's not right for this mission, so let me make a change, or we're doing the wrong sort of mission, so let me rotate it 90 degrees this way. I'm no longer the person that is diving into the problems, leading by example. I'm just some fucking talking head giving orders. Who the fuck am I? That's a big emotional change, and it took me the last 3 years to learn that. And so that was, that was very hard.

And are there things that you've done to address the need to keep raising the bar? Because I've, you know, I've— the guy I've heard talk about this quite a bit is Frank Slootman.

Yeah, Frank's great.

You know, he's very much like, okay, it's the CEO's job to keep raising the execution bar, to keep— have people be almost borderline uncomfortable that they're not executing well enough or aggressively enough because they entropic state is to not do those things.

It's hard. I mean, I think I'll say the biggest lever you personally have as CEO is the executives that report to you. And so being very aggressive about upgrading that group— you're always too slow, I find, because you're managing someone who is a domain expert and has a bunch of years more experience than you do in something. And so, like, I had this imposter thing for a while, which is like, okay, who am I to call their work bad? Like, what do I know about this function? But you have to get comfortable with that because that's the job. Like, someone has to do it, and that's you because you're the CEO. So you do it, you need to do it, you need to do it well. You always talk to other CEOs and everyone's like, yeah, we're too slow to change executives and upgrade and da da da, like always, always. So I remember I would always ask different investors and board members, I'm like, hey, Everyone always says they're too late. Do you know anyone who's like too early? Like, I'd love to talk to that guy. Like, let me know who they— let me know who they are. And then one of my board members, Niraj, pointed me to Rob Bernstein at Coupa. He's like, yeah, Rob is actually early to a lot of this stuff. He'll do it when people are like, what? What are you talking about? And get kind of uncomfortable with it. And so I'm like, all right, I got to go meet Rob to understand like how psychologically he's like figured this out to like not act too late because it's so freaking hard. And so I finally got a chance to meet him a few years back and I asked him, I'm like, look, I have been trying to figure out how do you become early on changing out executives because everyone's always too late. So like, what is it? What magic are you doing? And his response was the craziest fucking shit ever. He was like, Spenser, I am incredibly insecure and I think I'm not good at anything I do. And so because of that, I need to take every possible advantage I can possibly get, including being early to things. So I'm always early to meetings, I'm early to decisions, I'm early to like changing the team. And I'm like, holy shit, this guy is fucking insane. So I took away from that and I'm like, okay, let me see. Maybe I lean into that and maybe I lean into my insecurities and try to get after some of these things earlier. So that was at least the best response I heard.

Well, what, what should I have asked you so far that I haven't that do you think would help founders kind of in their early journey, especially if they're ambitious to do something really meaningful?

There's a lot of great reasons people are building companies. Like, for my co-founder Curtis, he really just loves the learning. He's always wanted to learn how to build a business of his own, and he just, he deeply enjoys that, and he wants to understand the craftsmanship that goes into building something great. For my other co-founder, Jeffrey, he's a fierce competitor. He's like fucking won at every competition in his life. He was on Stanford's ACM team, their national coding team. He did programming contests for fun. He got into startups. He's just a fierce competitor. For myself, so I was very lucky in that I had a lot of choices when I was 21 years old and graduating from college. And I could have gone into big tech, I could have gone into consulting, I could have gone into finance. And one of the things you realize is that you can kind of be any character you want in any book or movie. You can be the starving artist, you can be the family man, you can be the corporate executive, you could be the adventurer, you can be any fucking character you want. You can't be all of it at once. One of the biggest mistakes people think that they can do it all, It's like I think Ruth Bader Ginsburg says, you can have it all, but you can't have it all at once. I knew I was an ambitious person. I wanted to make an impact. And so I spent a lot of time studying people who had gone on to do great work. One of the stories that just sticks with me to this day is this— there's this guy named Norman Borlaug who was an agriculture expert in the 1950s and '60s. And the work he did completely changed society as we know it. So, uh, what he did was he brought modern farming techniques to the developing world. So he went to Mexico in the 1950s, and Mexico at the time was a net importer of food. They didn't have enough food to feed their people. And he developed this strain of wheat which was, uh, known as— is like a dwarf wheat, uh, high-yield dwarf wheat that was disease-resistant. So you want high yield because you want to get a lot of production per acre that you have. You would need to be disease resistant because often diseases would wipe out crops and you'd have a famine. And you need to have this other trait called dwarfism because it's natural for plants to grow tall because they compete to get light from the sun. But you want them to select them to be short because if they're tall and they're high yield, the stock becomes too heavy and the whole thing breaks off and you can't grow your crops anyway. So he spent a bunch of years doing this and In his time in Mexico, Mexico quadrupled its wheat production as a result of the strains, of the new strains he developed, and became— went from a net food importer to a food exporter. A few years after that, he went to India, and India was in real fucking bad shape then. It had just gotten independence from Britain, it had split with Pakistan, exceptionally poor as a nation, like way worse than China ever was. And then constant threat of famine. Like, you know, there would be years where like they'd have to beg aid for food from the Western world just to feed. Like, otherwise they died. And like, and this was getting worse. The population was exploding like this. And so the government there was like, fuck it. Like, we're desperate. We'll take a bet on this guy who did this in Mexico. Let's try to set him up in his work. Did the exact same thing in India. Develop new strains of crops that were high yield, disease resistant, and robust to lots of different weather conditions, more than doubled their food production over the course of a few years. Then he went to Pakistan, did the same thing there. Then he went to Africa, did the same thing with a little less success there. If you kind of sum up the impact of this guy's work over the course of his career, he fed quite literally billions of people. And now today, we no longer live in a world where food scarcity is the top issue in our society. Since the beginning of civilization 10,000 years ago to like, you know, the 1950s, we were worried. Human race has been limited by how much food we're going to produce. And what's worse is when during downtimes, when there's less food, fucking lots of people starve and die. It's terrible. It's fucking awful. Now we have bigger problems to worry about. We got to worry about energy and global warming and, you know, social media, like, but like, great, Food solved. And so I looked at that story as an impressionable young 21-year-old, and I'm like, man, if I can make a tiny fraction of impact with my life that Norman Borlaug did with his, I'm going to be— hey, that's worthwhile. That'll be my contribution to the world. And so I looked at what do I know how to do, and it's like, I know how to build software, so let me do that in the biggest and best way I can. And that was by building a company. So anyway, you know, you can have any sort of why, just make sure to pick one that, you know, can last for a very long period of time.

Yeah. Pick one that's worth, you know, putting your all into. Right. And just not just for how it comes across to other people, but how it, you know, how it honors the gift of your time.

Totally, totally, totally.

All right.

Well, cool.

Thanks for the time. No, Mike, thank you very much. And yeah, absolutely. I'll send you a note. We'd love to catch up with you guys soon.

Thanks for listening to the Pattern Breakers podcast. You can follow me on X @m2jr, and I encourage you to check out our newsletter at patternbreakers.substack.com. I'd love to have you subscribe wherever you get your podcasts so you don't miss an episode. And if you like the show, I'd be grateful if you could us a review. Until our paths cross again, I hope you embrace the power of thinking and acting beyond the conventional boundaries. It's the people who dare to be different who truly make a difference.