Spenser Skates - Challenging Big Ideas - [Founder’s Field Guide, EP. 42]

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Founders Field Guide listeners can redeem a $1,000 off coupon at vanta.com/patrick. That's vanta.com/patrick. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Founders Field Guide. Founder's Field Guide is a series of conversations with founders, CEOs, and operators building great businesses. I believe we are all builders in our own way, and this series is dedicated to stories and lessons from builders of all types. Founder's Field Guide is part of the Colossus family of podcasts, and you can access all of our podcasts, including edited transcripts, show notes, and resources to keep learning at joincolossus.com.

Patrick O'Shaughnessy is the CEO of O'Shaughnessy Asset Management. All opinions expressed by of Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'Shaughnessy Asset Management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast.

My guest today is Spenser Skates, CEO and co-founder of Amplitude Analytics. Spenser founded Amplitude in 2012 with a thesis that building the best product requires deep cross-functional understanding of customer behavior. During our conversation, we discussed Spenser's long history in programming and how his early experiences tie into his work today. We also explore the nuances of equity compensation, how different VCs can play a role in the success of a startup, and Spenser's desire to see more direct listings versus IPOs. While many founders follow the path of others, it's clear that Spenser takes time to challenge the status quo. Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. In this episode, you'll hear how Spenser's team worked with the meditation app Calm to optimize for customer growth. It was particularly interesting to hear this story after listening to the Calm breakdown. Find episodes of Business Breakdowns on your preferred podcast player or at joincolossus.com. Now I hope you enjoy my conversation with Spenser Skates.

Spenser, I was toying with where to start this conversation. I came across kind of an interesting factoid about you, which is I think I think you twice won a programming competition at MIT. This is going way back. I'd love you to describe that competition and what you think is the reason that you were able to win it twice.

You've done your homework. The programming competition, for those of you who don't know it, is this competition called Battlecode, which is hosted over this kind of one-month break that MIT students get in January of every year. It's a video game, and the competitors create an artificial intelligence for the video game. So think of it like StarCraft, for those of you who know that. You have a bunch of units, you send them around a map, you try to fight and kill the enemy. I first heard about it my sophomore year at school, and I was like, holy cow, this combines like all the things I love. This combines programming, this combines video games, this combines a competition. It was this really prestigious thing at MIT. People joked about it as like the Super Bowl for nerds, where a lot of the top companies would recruit there. So A lot of startups, a lot of big tech, a lot of finance, high-frequency trading firms would recruit there because the work is actually ends up being quite similar, more so than anything else you do in school. And so my sophomore year, I was, got really into it. I was so passionate and then I just totally sucked because it was my first time doing it. My junior year, I was just obsessed. Like I pretty much dropped everything else I was doing for the month before just to prepare for the thing, practice on the previous year's code, just learn all about it. And as it turns out, what makes you good at that is not the same thing necessarily as being a good programmer. Part of it is being a good programmer. Part of it's also learning the intricacies and the mechanics of the game, thinking really deeply about what things are going to work, what strategies will work against what opponents. We just went all out. I recruited my roommate. I tried to recruit my current co-founder, Curtis, but couldn't get him. He was actually on an opposing team that year. There was probably about 10, 15 teams who were quite serious and quite good at the— competition, and part of it was we did a bunch of good things and we just spent a lot of time. We, we didn't do anything else. We'd wake up, we'd code for 14 hours a day and just go to sleep. And that was like 3 weeks straight in the competition because we had spent so much time on it compared to most of the other teams. We had developed a really, really good AI. And then I remember there's one other team that was quite good that was like vying for us with the top spot. And we happened to get lucky with some of the maps and how the thing played out. Won it my junior year. And then my senior year, I wanted to do it again. And this time Curtis was like, yeah, I really should have joined you guys. The other people on my team didn't do any work last year. So we had me, then Curtis, and then two of our other friends, and we were just unstoppable my senior year. So it's funny because you look in that and you're like, oh, you must be a really good programmer, but I'm not. My co-founder is like twice as good as me. And one of my other co-founders, Jeffrey, he's like 4 times as good as me. There really is a lot of parallels between that competition. And starting a business is probably the closest experience you could get to that at MIT because it wasn't just about being a good programmer. It was about understanding a problem, learning about it, iterating on it. It was some of the best fun I had. And that was what actually got me my first job, which was at a high-frequency trading firm in a place called DRW in Chicago, and then also introduced me to the world of startups because a lot of successful, former successful Battlecode contestants had gone on to start companies. Drew and Arash, the founders of Dropbox, There's a few others.

If you had to look back and you could choose junior or senior year and isolate like a single stroke of personal genius, like something that you think was really special that you pulled off in the course of those two seasons, I don't know what you want to call it, competitions, what pops to mind?

There's so much. One of the mistakes people would make in the competition was like, hey, let me create the best navigation algorithm. But that didn't really matter. It really was about creating one that was good enough. And then having your AI adapt to whatever the right strategy was on the map. So certain maps, it was better to just go and try to win and fight the enemy and beat them in a big fight. Certain maps, it was better to try to spread out and gather resources or run away from the enemy. And so for us, it was just like we would constantly scrimmage our bots. They had a scrimmage server that you could play before the final competition. Other teams would be like, oh, I don't want to show my strategy on the scrimmage server. This is totally stupid. There's like 300 different teams competing on this thing. You're going to learn two things. One is like you win, in which case you have now gotten a bunch of information about why your strategy is good. Two is you lose and you can understand why you lost and your bot can be better. And yes, it'll make whoever you compete against for that scrimmage also better. But like there's 300 contestants, you can scrimmage all of them. It's so funny because it's so similar to startup world. People will be like, oh, got to protect my idea. Inexperienced entrepreneurs will be like, oh, I don't want to share. I don't want to share my idea with anyone, but it's like, no, no, no. Firstly, no one's going to steal your idea. No one cares. Yeah. No one cares. And if your ideas are— I can't remember who was it that said it, but if your ideas are any good, you're gonna have to ram them down people's throats. Yeah. And then two, like, it's going to make it better. The amount of value you get, the world is just such a big place. It's like the kind of tit for tat strategy. If you give value to it, you'll get value in return. And so that was one of the things.

Talk me through the bridge from that competition and some of the lessons learned into the starting of Amplitude. Definitely describe what the business does at this stage for those not familiar.

I knew I really wanted to start a company. It was clear. I was lucky enough to be in the position where I had the option to do so many different things and I could take my career and I could go into finance or I could go into consulting or big tech or start a company or go into nonprofits. One of the questions I asked myself is like, okay, well, what is it that I want to do with my life. I'm really fortunate to be in a position where I have lots of different options. And I actually came across this story which really inspired me. It was about this guy named Norman Borlaug, and he was an agriculture expert in the 1950s and 1960s. And what he did was basically brought modern farming techniques to the developing world. If you kind of go back all the way to the '50s and '60s, one of the biggest problems is if you look at the population graph, it was exponential like this, but if you looked at our ability to produce food, it was kind of leveling off. And so there was this huge concern around, we're going to run out of food and we're going to have this Malthusian crisis. We're going to have way more people than food. In the year 2000, there's this famous book, Limits to Growth, which talked about how the year 2000 there'd be starvation and riots and famine and war and just all these awful things if we didn't do some form of population control. Now, they turned out all to be wrong, and a huge reason is in part through the efforts of this one guy. And what he did was he went to Mexico, which at the time was a food importer, so it'd need to import food from the United States. And he developed a new strain of wheat that was high yield, was resistant to disease, and that had this other trait called dwarfism, which is important when you're making high yield crops. And through doing that, the wheat production of Mexico quadrupled in a few years, and then they became self-sufficient in terms of food. And then he went to a few years later in India India was even in worse shape. It had just gotten independence and fast-growing, incredibly poor country. They were desperate to try anything. And so he helped them do the same thing there. And after a few years, they became self-sustaining. He went to Pakistan and did it there, then went to Africa and did it there. You look at the sum total of his impact over his career, and it was clear he was able to make impact on billions of lives. He saved hundreds of millions of lives. He got the Nobel Peace Prize in 1970. And to this day, a huge part of the fact that We don't have to worry about food as a human society is due to his efforts and the Green Revolution around it. Now these days, our problems are different. We think about energy, climate crisis. Food is largely off the table, which is an incredible place to be as a society. So I read that story as a young, impressionable 21-year-old, and I was just so inspired. And I was like, "Man, if I can have a fraction of the impact that this guy has on the world, I'm going to be really happy with wherever I end up in my life." I said, okay, well, what do I know how to do? Well, I know how to build software. So what's the biggest and highest leverage place I can do that? No question, Silicon Valley. If you look at how our lives are different today than 20 years ago, it's through all the advances in tech. If you look at how the lives of the poorest of the poor are different today from 20 years ago, exact same set of things. It's all the advances in mobile and tech. I said, okay, well, let me go ahead and start a company here because I believe this is the greatest way to do good. So that was kind of the very start of me deciding to get into startups. The funny part was after getting into it, it's like the first few years are nothing like that. You're just like trying to get anyone anywhere to be interested in what you're doing. We worked on 5 or 6 different ideas that didn't turn out. We did one app called Sonolight, which was a voice recognition app. It was like a version of Siri right around the time Siri was coming out. Did Y Combinator with it. That failed. But through it, we actually found this really interesting thing, which is what led to Amplitude. So for those of you who don't know Amplitude, Amplitude, what we do, we call ourselves the digital optimization system. So what does that mean? We're the analytics brain behind understanding what's going on in your product. So our main product is product analytics, and it basically, what it does is it helps you take a data-driven approach to developing product. And so when we were starting the business, what we saw was that some of the most sophisticated companies, you look at Facebook or you look at Zynga, You look at Netflix, they had taken a very quantitative approach to developing their products, which was quite different. A lot of people think product development, it's like Steve Jobs at Apple. You sit in a room, you think really hard and you're like, oh, I know the brilliant feature. But it turns out some of the best companies were actually totally changing it. The metaphor I like to use, it's the world of product was going through this transition from like a Mad Men phase where you literally had people in suits with cool ideas that had an MBA degree from, you know, wherever being like, oh, here's the cool pitch that's going, here's the feature that's going to work. To a moneyball approach where you could actually quantify the impact of specific features and say, okay, if I'm Facebook, hey, what do people really like? They really like having a social network and friends. So let me design my product around that. And we looked at that and we said, hey, every single company out there is going to need this. And so that was 2012. We launched the company in 2014, and we've been lucky since that it's just been up and to the right. And the most recent piece of news that we put out is we just raised a $4 billion valuation round last month with Sequoia and a few others. So that's a very short version of the journey of how I got into Amplitude tech and then to Amplitude.

Can you give an example of how a customer, maybe even a real example, uses the product specifically? So I think everyone will understand the Mad Men to Moneyball thing. We've talked a bit about that. I couldn't agree more, right? Like there's room for both. There's room for genius. There's room for inspiration coming out of the ether. But of course, then there's also good room for using data to improve things. So a company approaches you, what do they do? Literally walk us through the sort of customer journey.

So a typical customer will come in, they'll say, hey, we have this goal this year to increase the number of people using our app by 50%. And then the first question we'll ask is like, okay, well, how are you measuring it? In a lot of cases, they aren't, or they don't have a great way to measure it. And that's where we come in. And then once they get on board, they'll spend some time to instrument and get set up. And once they get on board, they'll want to understand, okay, what is it that drives engagement in our product? What are the features people use? What leads people to come back? What's the difference between people who come back and people who churn? Where do people get stuck? And they start answering all these questions to start making systematic improvements in their product. I'll give you a really good example is, so we worked with this meditation app in the early days named Calm. I don't know if you're familiar with Calm, Patrick. No, very well. Yep. They are the top meditation app on the App Store these days. But when they were first starting out, they were trying to figure out their product market fit as a company. And they were asking, OK, what is it that gives our users tremendous value? And they looked at all the different features someone could use as part of— they looked at, OK, well, what if you use this meditation versus this one? What if you use it for sleep versus use it for exercise? Is there any differences there? Guess what the number one predictor of a long-term engagement was. Number one characteristic or feature of a user make them a highly engaged user.

I don't know whether or not they were— had trouble sleeping or something.

So that's what they thought. They had all these hypotheses that was, you're this type of user versus this, but the number one predictor was whether someone decided to set a daily reminder to meditate. Now it sounds so obvious, but what was crazy was only about 3% of their user base was using feature.. And the reason only 3% of the user base was using the feature was because it was buried in like a settings menu. You had to go to settings and reminders and then set daily reminder and like 4 or 5 clicks, which most users never went to. But what they realized through looking at— so what did they do? Okay, well, they said, okay, let me bring that feature to the front. So when you first sign in, bam, it hits you. Do you want to set daily reminder to meditate? They went from 3% to more than 50% of their user base setting a reminder overnight. The retention of their user base tripled. They went on to be top meditation app, top of the App Store, Apple. They were Apple's App of the Year in 2018, just all this amazing success. But the core of the insight was that a huge part of their product's value to their customers was not just around walking and guiding you through a meditation. A huge part of the value was helping you develop a healthy habit around meditation. They hadn't even realized that without it. To the point of the Moneyball approach, that was the most undervalued feature in the application. Now, not every app makes sense to set a daily reminder for. Specifically, if you're in fitness or lifestyle, that's when it creates tremendous value, but it didn't even occur to the 50 people at the company. One engineer just put in the feature on a whim. They wanted it personally, and it turns out it was the most important one for the rest of their user base.

How does the product that you've built— I'm curious how this has evolved over the years, flexible enough to be able to identify this stuff in what I'm sure is a crazy wide assortment of products? Like, is there some fundamental unit of engagement that you're tapped into? Like, how's that possible? It seems like it would be very hard to do.

The reason that this is not possible to get out of a database or other analytics platforms is that because the way data is structured, we ended up deciding to write, which I don't recommend anyone do, but We did it a custom database where all the data for a single user is located in the same partition on the database. And so what that allows you to do is it allows you to scan their entire journey really quickly to ask any question. So you can say, okay, do users who use feature A engage more than users who use feature B? Or how many times does someone have to come back to be, you know, a long-term sticky user? Or what's the most common path that someone takes through the app? The trouble is, if you think about product data, Every single user's journey is unique. Products are not go click, next, next, next, done. They're not linear things. It's more like a random walk. And so the question is, how can you analyze that in any sort of meaningful and consistent way? And so the key part from us is like, okay, well, let's make it really easy for you to ask a question about a single or a given user's history really quickly. The example I just shared is one of the more advanced use cases. Most customers on Amplitude are just doing the basics. It's like, okay, show me How my users retain, show me where people are getting stuck in a conversion funnel, show me what the key differences and feature usage between those two groups. There are parts of the product that sophisticated AI, but most of the vast majority you can do just simple correlations, simple questions. That's the key that most companies struggle with that we're there to help them.

What have been the biggest mistakes that you've made that have been productive, meaning you've learned something major from them in building the company itself?

Productive. Oof, so many. That's so funny because it's like you think of things that are productive and you're just like, oh, that must not have been a mistake retroactively. I mean, I could definitely list tons of things that it's like we were slow to hire outside executives and every company and every founder CEO is slow, but we were like extra slow and that definitely was a mistake and in some ways held us back. The flip side of it I'll say is that it gave the early team a lot of ownership and a lot of agency, made them very invested.

Why is it important to hire outside executives, do you think?

When it comes to scaling a company and building what a function looks like, so building your finance function or building your sales function or building your engineering function, this has been done tens of thousands of times before, and there's industry expertise out there on how to do it. Now, you could try to go relearn that yourself, or you could just take their knowledge and stand on their shoulders to get further ahead more quickly. And so you're always much, much better off learning calculus from Isaac Newton than trying to invent it yourself. He only did it after thousands of years of work from other folks in math. And so it's kind of the same thing here. You could try to reinvent an organization. Most founders, CEOs, that's their instinct too, but it's a big mistake. Learn from them and figure out, okay, what's the right thing for you?

Maybe one more. I love these examples of just like things that maybe weren't the perfect strategy in hindsight, that you did anyway and you still learned from it. Anything else stand out? And then move on to some other interesting topics.

The biggest one is when we were doing Sonalight, we developed our own analytics system in-house, which was just a colossal— so many teams do this, but it's a colossal waste of time. We're two of us at the time. We probably spent one-third of our development time just trying to build analytics, and it's like we weren't even experts in that thing. We wanted to make Sonalight successful. We should have outsourced that to someone else and just focused on voice recognition and what we were good at and finding the product market fit in there. But it turned out because we have Amplitude today and it's massively successful and would have been there without that mistake.

One of the things we talked about before hitting record is just this view of yours that so much of what happens in the world is just inertia. Everyone else does it this way, so we'll do it this way. There's a number of interesting examples where you've encountered that problem and then I think tried to view things in terms of how you're going to build them at Amplitude differently. The first one is equity. Obviously, like everyone knows about equity, it's given to or assigned to key employees more early on, less later on, blah, blah, blah. It's all kind of done the same way. It's really important. Obviously you want long-term alignment. I think everyone would argue it's a good thing for more people to have equity, mostly a good thing. But I think there maybe are some strange things that you found with its history and why it was originally developed and how that's impacted people's lives ever since. Can you talk us through this interesting angle that you have on the role of equity and how it should be used?

[Speaker:SPENSER SKATES] Yeah, absolutely. You first have to go back and look at why equity was created as a compensation mechanism. So the very first company to make it a standard thing to give you equity grants was, at least in the Valley, was Hewlett-Packard back in the 1950s. And they did it for a few different reasons, partly to incentivize building the company, but partly out of a, hey, we want the workers to own part of the company too, you know, kind of a blend between capitalism and socialism where we're saying, okay, you know, we're actually going to give the workers part ownership of the means of production of what we're doing. Since then, it's become a standard practice in startups, which is awesome because it gives people a real feeling of agency over what they're building in a way that cash compensation just can never do. Because of it, you can get some really fantastically successful and rich early employees. You look at the early employees at so many different companies, Facebook, Google, Airbnb, Dropbox, tons of others. There's tons of folks who became phenomenally wealthy through the success of their companies. And in cash compensation, probably some of the highest people in terms of cash compensation in the world will make something like $10 million a year or something like that, which compared to how much wealth you can accumulate through equity, that's nothing. That's absolutely nothing. With equity, you can get people worth tens of millions or hundreds of millions or billions in some cases. It's this really great tool in order to do that. Now, one of the interesting things is just when we first encountered this early on at Amplitude, I asked a ton of questions about why it was set up the way it does. A lot of the answers, whether that's from lawyers or from others, are just, this is the way it's always been done. One of the ones that made absolutely no sense to me was this thing called the 90-day exercise window. And so for those of you who don't know, 90-day exercise window is if you're an employee of a company and have been granted equity or options specifically, if you end up leaving that company, whether you're fired or you just voluntarily leave or whatever the case is, you have 90 days to decide whether to spend a whole chunk of cash to exercise those options and convert them to equity. Otherwise, you lose them forever. I don't want to get into why we do options as opposed to outright grant of shares, but there's a bunch of tax reasons that that thing exists. And so when I started asking about, okay, why is it that you have 90 days to actually decide whether to become an owner of this equity? Because the problem, if you're an employee leaving, is that companies these days aren't going to see liquidity for 7 years at least, maybe 10, maybe even more if you look at how long some of these have been private. And you have no idea You lock up your cash in a company with an uncertain future, for a lot of these folks, can amount to tens or even hundreds of thousands of dollars, which a lot of people don't have just sitting around. And even if they do, you really want to take that risk. The reason I was given the 90-day exercise window exists is because you want to incent the people that decide to stay. But it's like, okay, well, even if you leave, if you decide to exercise, you get it. So you're only really incentivizing the people that don't have money. And it's like, it's almost a form of like wage slavery or equity slavery. People talk about the golden handcuffs. This is it. It's crazy. Like, I don't want people who are going to be at my company just because they're sitting around vesting their equity and they don't have enough money to exercise. That does nobody any favors. And then the other part of it, imagine this were cash compensation. Imagine you gave cash to employees and then 90 days after leaving, they had to give it back to you. The NLRB would be up in arms. There'd be no way this thing would ever fly. There'd be wage theft, people would riot in the streets. It's like, there's no way that you'd be allowed to take back cash compensation after someone left. So why let people do that with equity? Now, as it turns out, after pressing a bunch of lawyers, and I had to ask a few different lawyers, the first one we met actually was just like, I've never heard of this thing before. This is crazy. What are you talking about, Spenser? They wrote me this long essay being like, I've worked with hundreds of companies and none of them have ever— or I've worked with thousands of startups for nearly a decade and I've never heard of this idea. My spidey sense tells me there are some serious pitfalls. And it's just like, anyway, I finally found a lawyer who was willing to hear me out on this thing, Craig Spenser at Goodwin Procter. And he basically explained to me the reason this exists is because of a quirk in the tax law where options granted to employees are considered ISOs, so I think incentive stock options or ISOs. And you're not actually allowed to hold them if you're not working at a company. You have that 90 days to decide whether to convert them to equity or you lose them. But there's actually a really simple workaround, which is you can just convert those ISOs to NSOs or non-qualified stock options, and you can just hold them indefinitely, no problem. And so we ended up making this change, and it took some work to get our board on board with this change in equity, but it ended up being a huge differentiator for us. We were the first company in the Valley to give 10-year unconditional exercise windows to all employees regardless of situation or tenure or whatever else. Other companies have started following suit, which is just phenomenal to see that we can now grant equity in a way that's more beneficial to them without having all these crazy asterisks and gotchas in it. Equity compensation is so important at early-stage startups. It makes up a huge percentage of the expected value. Now people debate, it's like, okay, should you believe in it? Should you not? Like, only take cash? I'm not here to debate that. But for a lot of people, they really, they are meaningful. And one of my lessons was that, like, in explaining this to employees of Amplitude, after I spent all this time learning about them from lawyers, when I was actually explaining them to candidates and employees, nobody had any idea how equity really worked. And a lot were expecting to be taken away to some gotcha. And so for us, it was like, okay, hey, Let's actually try to be really transparent and fair and aggressive with how we grant equity to employees, and this can be a huge differentiator for Amplitude. And so that's ended up working out great, particularly a lot of the early team felt so much ownership in the company and was a large part of why we're able to break out of a crowded market and be in the dominant position we are today. So anyway, that's my rant on 10-year exercise windows.

What do you make of how it should vest? So Another kind of interesting thing that's happened is I think a few big companies have changed to literally a very short, might even be like 1-year vesting schedule for new equity issued. What do you make of that change in incentivizing people?

Awful, awful change. I want to write an open letter to the employees of Coinbase and Stripe and Lyft and all the others who are doing that and just saying, "Hey, this company does not see you as an owner. Come to Amplitude or come to a company that actually sees you as an owner." and will give you 4-year vesting schedules for your equity because they'll write long posts and they'll have their HR people say, "Hey, this is actually better for you because we can price your equity in market." But one, at a fast-growing startup like any of them, equity only goes one direction, up. You're giving them 1 year but leaving out the other 3 years. There's no way you're going to have that huge ownership upside and potentially get very wealthy by working at that startup with 1-year grant windows. Not going to happen.

You think that functionally what's happening is if it's a 1-year, it really is more like cash comp because you kind of know what it's worth. And yeah, the equity value may go up a lot in 1 year, but not as much as it might in 4 years. And likely what's going to happen is maybe they'll give you the same dollar amount at issuance, but they'll do it over 4 years, which ends up being much lower in total amount than if they gave you a bigger chunk upfront invested. That's right.

That's exactly right. When you get to the 1-year point, it's like, they're exchanging equity as basically cash. It's a little bit mercenary-like. And so if you're looking to be a long-term owner in a business and share in the massive potential upside, you want to get as much equity as you can as early as you can, which is why I love— I think there's an argument to do them even longer and to get more, but I'll leave that battle for now— and join a company that sees you as a 4-year owner in the business as opposed to, you know, a 1-year mercenary.

Your cap table is kind of a murderer's row or rush bar, whatever analogy you want to use, of really great investors. Tell me what you've learned about working with investors, and I'm curious too how you think about the next stages like public markets and how to make that transition, assuming the business is on that trajectory. What have you learned first about dealing with some of the best benchmarks, Sequoia, IVP, et cetera, some of the best investors out there, and what lessons could you share with others going through that same process?

I'll talk about private market and then we can talk about public market after. For private market investors, what's funny, before I get into it, I'll first say my mentality coming into fundraising was that investors didn't know anything and that advice was all undifferentiated because that's what Y Combinator teaches you, which is directionally to a first order approximation, correct. You got to build the business. No one else is going to have some secret to build it for you. It's on you. What fundraising can help you do is help give you cash, but That's the main purpose. It doesn't give you some magic powers that you didn't have otherwise. By and large, there's exceptions, but by and large. I remember the very first VC I invested in, I'll give them a lot of credit, Maris Capital. This was the seed round. I told them to their face, I fucking hate venture capitalists. I told them that. And they're like, I hope you don't mean us. I'm like, no, no, no, I love you guys. You guys are the best. I had gotten this kind of YC investors or don't matter view. Now what I've learned is I think with most Series A investors, that's the case. There are an exceptional few that can change the trajectory of their business. So when we did our Series A, so for those who don't know, we did our Series A, we ended up doing it with Eric Vischeria from Benchmark. A lot of ways, he's the best. He just had Confluent IPO. He has been trajectory changing. We'd be a tenth of the size if it weren't for him. It's been like having another co-founder in the business, like a lot of ways. But I didn't know that at the time during our Series A fundraise, we had gotten 5 different offers. We had built the business to about a million in ARR at the time. We were hot. There was a bunch of interest and it came down to Benchmark and one other offer. And the other offer, who I, I won't say who it was, but they were incredibly generous. Really liked the partner there. They were going to take 10% of the company, a really small chunk. They weren't going to ask for a board seat. They were going to do a really high valuation. They were like, 50% higher than anyone else. I think they were offering to invest at like a $40 million valuation or something like that, which was incredibly high at the time. These days, not so high. These days, very, very high, 2014. And here you come benchmarking Eric, he's the lowest of the 5 offers. He asked for a board seat, he's asking for a quarter of the company, he wants to pay $24 million pre. I've tried beating on him a bunch. I was like, Hey, I'm going to take this other offer. They're offering everything better. Can you at least move a little? And it's like, all right, all right, I'll go down from 25% ask to 24.5%. And I'm like, I'm okay. I asked a bunch of advice. A bunch of folks say, hey, take your other offer. You know, that's the best offer, you know, on all the terms. But there was a group of entrepreneurs who had worked with Benchmark who absolutely pounded the table for them. I did a little bit of homework. I didn't actually know a ton about them then. But I looked at the set of companies they had invested in them, and I was blown away. Twitter, it was Yelp, it was Zendesk, it was New Relic, it was Snapchat. This was like the who's who of Silicon Valley. And I'm like, holy smokes. I did quick back-of-the-envelope portfolio analysis, and I was like, man, if you work with these guys, probably about half their businesses go on to be massively successful, incredibly massively successful. That's a way better hit rate than any other VC fund. Most VCs will get like 1 out of a portfolio of 30. If you're good, maybe you'll get 1 in 10. This is like 1 in 2 companies are successful. Now, I didn't know if it was correlation or causation. It was like, okay, is benchmark causing? Are these really good selecting? It's always some of both. But I was like, okay, this is what— I'm here to do Norman Borlaug. These guys are down to do that, even though this is worse terms in every respect. I ended up signing with them and it was Even better than could have expected. I probably talk to Eric once a week. A lot of VCs brag about, I want to be the entrepreneur's first call, but it's like, I'll call him about anything, whether it's a management issue or there's a company crisis, for help on personal stuff. And so he's interviewed hundreds of people for us. He referred at one point, one quarter of the early team. A lot of the engineers was at Amplitude. He's interviewed every single exec, been on every single recruiting process. I've been in, been the most helpful with every single fundraise we've had. Without that, we wouldn't have broken out. Analytics is a crowded competitive market, or at least was very crowded and competitive when we were starting. There were probably a dozen different players doing similar things. And I, no question, we would not have been the one to break out if it weren't for the amount of work Eric— now you'd never know it because Eric's not going around promoting himself on Twitter like some of these other VCs, but in terms of raw impact, In a lot of ways, it's like having the right co-founder because it'll change. It'll absolutely change your trajectory. So the lesson is most VCs are undifferentiated. There are a few exceptions, and you can tell by looking at their portfolio. So look at the companies they've been with. And then these days where rounds are getting closed in like -2 days, I understand it's hard to do references, but you should do references. Understand, think about this is a long-term commitment. What's the business you want to build 10 years from now? And then look at the companies they've built. Look at them, not just the really successful ones. Any VC worth their salt these days, I mean, you better have a successful company, otherwise you should be out of business. But look at their unsuccessful ones too. Look at their whole portfolio and ask yourself, okay, well, which portfolio do I want to be in? And so for me at the time, that was a really easy question. I think a few of their funds have been like 50x, which is wild. I mean, normally it's like you're good if you do 3 to 5x. And so it's like, yeah, I want my company's equity to be in that portfolio.

It's a fascinating lesson, which is like maybe it's mostly a commodity, but not entirely. I know Eric, and I've had Eric on the show and you can listen to that and see. You can go double-check your points by just listening to the guy talk. I mean—

Eric is way too humble. It drives me bananas. He makes a face whenever I've told him this, but he has the highest ratio of quality to whatever brand presence there. So he asked the CEOs of these companies and asked them what they've actually done.

That's where you'll hear it. He's a remarkable guy. Just look at the scoreboard, like you said. I'm not sure I've ever asked this specific question, which is like, you have this weird dichotomy of— I'm asking a little bit to look forward to the future, and I know you've done some research thinking about this topic, but shareholders like that are very different than shareholders you're probably going to have in public markets. Of course, there's amazing public markets shareholders, I'll call them, versus investors, maybe sometimes board members. But that's sort of the rarity. Even the biggest famous portfolio managers, for the most part, maybe they know the company pretty well, but it stops being about them bending the trajectory of the business and more about them selecting the right businesses to earn the best returns. So with that in mind, how do you think about it? Back to you approaching equity in a unique way, do you think you'll approach, or have you so far thought about this in any way that you think the audience would find interesting? Because this world has really evolved into this crossover world. Everyone's doing both. The way companies go public has changed. There's all these SPACs. You strike me as someone that's thought about this. What's your research yielded here?

[Speaker:SPENCER SKATES] I have a very, very long rant on the IPO and the process that it's wild that such a thing has been constructed. But before we get into that, we recently raised around, and to be clear, I love the stockholders in Amplitude, but 90% is the financials of the business, and there's a fair price for SaaS companies. So we just raised around at $4 billion. If we had been at $3 billion, there would have been 20 investors that were in. If it had been at $5 billion, there would have been zero. And so the market clearing price ended up being $4 billion for Amplitude. And so as you become public market, there's a fair price for SaaS companies. A lot of it is out of your control. Depends what the Fed does with interest rates, depends what happens with technology stocks in general. It's just like a fair price. You don't control it. All you can do is build your business and set yourself up for success. And so because of that, price is like, say, 90% of the factor. You might have like 10%. It's like, look, I love Working with the folks at GIC, they're a sovereign wealth fund, and there's a bunch that's attractive about that. I love working with Sequoia. To Pat's credit, he's done the most work I've ever seen out of a growth stage investor. He was a big help in hiring some of our recent executives, and he does a lot of work on behalf of the company. But there is that. I don't want to dismiss that, but 90% does end up coming back to the price as you get into these later stages, and then particularly as you get into public markets.

So what are your thoughts on this method of going public? Obviously I've done a bunch of fun stuff with Bill Gurley, both on the podcast and just separately. This is a big, interesting issue for him. I think it's a big, interesting overall, right? And I actually don't have a strong opinion one way or another. It's not something I've had to deal with personally, but it does seem as just like an interesting evolution of capital markets that everyone used to have to IPO with the same two companies. And I think some people have pointed out really interesting potential flaws in that. Process, and now there's SPACs and there's other ways of doing it. What do you think? Do you think that this will change a lot, or is this sort of a passing thing where we'll go back to IPOs?

Patrick, I'm going to give you and your viewers the most extreme view on this. As I've been doing my homework, the entire process, I'm not a conspiracy person, conspiracy, but it's just wild how bad and awful the traditional IPO process is for companies. The whole process is set up to give you a bad outcome. You hire consultants, your investment bankers, to advise you and bring you through the process, but their incentives are not aligned with yours at all. It's the principal-agent problem to the most extreme. And then not just the bankers, but the entire ecosystem, public market funds, and then press, your lawyers, and the folks on your side, they give you this advice to basically lower the price of your stock for a bunch of reasons, but that's against your own interest. As a fiduciary to Amplitude, my job is to get the best price for equity on behalf of my existing shareholders. If I were a shareholder in one of these other companies that has like 100% day one pop on the stock, I would sue for breach of fiduciary duty because it's like whenever you have big price movements, that's a sign of a massive inefficiency in the market where one player does not have the correct information and what the true price of whatever their thing is, whether it's their equity or something else. And so the whole thing, I don't want to say criminal, but it needs to be just totally broken down. Thank goodness for the rise of the direct listing because that's a much, much superior way to take your company to the public markets. And so for any CEO that is going through this now, who is interested in learning, okay, what should I do? Should I do traditional IPO? You absolutely have to do the direct listing because any Anything else from my standpoint is a breach of your fiduciary duty to your existing shareholders.

Trey Lockerbie: Was there something that most tipped your view in this direction? I'm curious. Let's take SPACs, for example. I think for the most part, people have a fairly grim view of them and they were oversupplied, too many people raised them, whatever. But I think some of the better SPAC investors are offering a really interesting product where it's better, faster, cheaper kind of thing, right? Good valuation that you're comfortable with, Speed, et cetera.

[Speaker:IAN_CASSEL] I don't love SPAC because in a lot of ways, it's an end run around the SEC. The point of the SEC in general is an institution to protect shareholders from unscrupulous actors, whether it's companies or banks or whoever else. And one of the big constraints in the public listing process, whether that's an IPO or whether that's a direct listing, is that you have to disclose all the facts about your company and you're not allowed to say, tell about the future of your business with too much certainty because the reality is you don't know. With SPACs, it's a total end run around it where you can say whatever the hell you want to whoever the hell you want because the company is already public and you're doing a reverse merger where you acquire the company that's private, and then the shares from the private company become the ones from the public. It's basically an end run around all the structures that the SEC has put in place. There's a good reason for 90% of those structures. There's 10% we might want to change. And so you get companies that say, hey, we're going to forecast $100 million in revenue even though we don't have any today. We're going to forecast $100 million next year. And then, oops, just after we're public, we're going to bring that $100 million down to a $10 million forecast. It's wild what you're allowed to do as part of the SPAC process. And so to me, my recommendation both on the CEO side and the public market investor side, you know, at least for now until a lot of this stuff gets sorted out, is to stay away from SPACs. There's a good reason for a lot of the information disclosures and protections that exist that are already in place. That said, within the public listing process, IPOs are just so backwards. So the real clients of the investment banks are the large, long-term public market investors. Now, the craziest part of it to me, there's like a Stockholm syndrome in Silicon Valley where the people that have convinced themselves the most are the venture capitalists and the existing players in Silicon Valley, not even the investment banks and public market investors. Andreessen Horowitz, one of the great VC firms out there, wrote a whole long series talking in the defense of the traditional IPO. I'm like, "What are you guys doing?" Traditional IPOs are bad for existing shareholders. So that means me as a founder, that means my employees, that means my existing investors. They're also bad for retail investors because in a traditional IPO process, you don't give allocation to retail investors. You basically do this transfer, do this massive giveaway of tens of millions of dollars, or some cases hundreds of millions of dollars to public market investors. And for what? Charity? We're a business at the end of the day. This is like the cronyist of crony capitalism. Anyway, I'm going to stop my rant for just a second.

[Speaker:SPENCER SKATES] It is interesting to hear your perspective. Maybe one thing to poke and prod, I haven't read the Andreessen thing, I do think maybe one interesting criticism of the comparison is that it's kind of apples and oranges because In the IPO process, you're raising money. And the dilution that you take, obviously it ranges, but you're raising primary capital into the business. In a direct listing, you're not. It's existing shareholders that are selling some percent of the float of the business. And I know that everyone's trying to change that and have the ability to attach a primary raise to a direct listing. But very often you see a late-stage, very late-stage, just pre-public raise from a company. And that's the way they put cash on the balance sheet and then they go public. Do you think there's a chance that it's just apples and oranges? Because raising money has a price. It's hard to raise money for most people. Maybe this environment's a little bit different, but that's the one question I have is just fundamentally there is one difference there and maybe that explains something. I don't know. Like I said, I don't have a dog in this hunt, but have you thought about that, that maybe it's just not the right fair comparison?

[Speaker:SPENCER SKATES] They need to change that for sure because that is definitely one of the biggest downsides of the direct listing process is you can't do a primary capital raise. So you're either forced to do it after you go into public markets or before. Either one can work. You can at least run an— if you're going to do after or before, that's better in my mind than doing it as part of a traditional IPO, because at least you can just run an auction process yourself instead of hiring consultants to give you advice to keep your price low. I've heard the argument, oh, well, a CEO, you can just tell them what to do because you're hiring the consultants. And I'm like, do I really want to set up a process where I'm going to have to fight the existing thing I set up? That makes zero sense. In a lot of cases, a lot of these bankers will threaten to hold up the IPO and say, "Hey, if you're too high on the price, we're not comfortable going out, and so we can't actually do it." And it's like, you're holding my company hostage. It's absolutely wild. And to be clear, it's not explicit collusion between the banks and the public market funds. It's just the way the process has been set up. One other fact, Bill introduced me to Jay Ritter, the University of Florida professor, done tons of research on IPOs, and he looked at IPOs going all the way back to the 1980s. One of the really interesting things in his data, and so if you look at all the total amount generated in those, about $1 trillion in total, so massive amount of money that have been transferred during the public listing process. If you go back, on average, there's about a 25% underpricing. So what that means is of that $1 trillion, about $200 billion was inefficiently priced and given away from companies to these institutional public market investors. I heard it described, it's basically the largest arbitrage opportunity in all of finance. And so for me as a CEO, do I want to be on the other side of that? Absolutely not. One of the most interesting things to me is all the reasons that people have constructed around why it is you should go with the traditional listing process and underprice yourself. There's so many bad reasons. And so I just wanted to enumerate some of the ones I've heard as well as why they don't make sense. So One I've heard is like, oh, you want to be able to control your price. And it's like, okay, well, that's not how prices and markets work. You don't know your price either. That's why you have an auction process to discover your price. So trying to control it, it's wild the way it's done. And I just talked to a board member who just came from an IPO, and they said they literally just sat in a room, decided the price out of a hat. And it's like, it's like, what are we doing here? The other one I've heard is like, oh, you want a price that always goes up so that the press and employees think it's a good thing. I think it's silly. Like, employees are smarter these days. They're not expecting a monotonically increasing stock. No stock ever has that. That's a silly expectation to try to drive and one that's inefficient. The worst one though I've heard, I'll just close with this, is that like, if you price too high, you'll price out people who will stick with you. It's so backwards in terms of how markets work. It reminds me of that famous Yogi Berra quote that says, nobody goes there anymore, it's too crowded. And it's like, look, as a CEO, I want someone Who do I want as owner of Amplitude? Whoever wants to pay the most. That's a representation of the belief that they have. And so this idea that one fund is better than another, the point of the public markets is that it's an open market and the best price ends up getting to be the owner. And then this idea that if you price low, your price is going to be higher in the future is also totally backwards. I was in high-frequency trading. If the price is high now, that's an expectation it's going to be high in the future, not the other way around. Anyway, I just wanted to make sure to share that piece. There's some really bad thinking around the traditional public listing process that just needs to change.

So of course now I have to ask, given the interesting views on both equity and going public, are there other— what's the right term— sacred cows or something that you have similarly divergent opinions on that you think are worth bringing up?

Those are the two I've spent the most time trying to understand. I could go on. I'll say the other one that I'm spending some work looking into is dual-class structures. Most companies who go public these days have a dual-class stock where basically if you own the stock before the IPO, you get 10 or 20 times the vote. And then if you buy in after, you only get one vote per share. I think it's actually really bad from a corporate governance perspective. Now, the argument that they'll make is that, okay, well, You want the founders or the founder CEO who has the most long-term view of the business really have the most votes in driving where it goes. But from my standpoint, why are my shares special versus someone else's? Why are Benchmark's or Sequoia's shares more special than a public market investor? No reason other than we're grandfathered in and we've been here for longer. The flip side of it, as a CEO, I do want to incentivize long-term ownership of my shares. And so I would love there to be a way for companies to basically, the longer you've held the shares, the more votes that you get in electing the board. Fortunately, Delaware corporate law and the SEC hasn't innovated on that stuff yet. And so what most companies end up doing these days is just having a dual class with the argument that, hey, founders have a more long-term outlook in the business and so they get more votes.

If you think 5 years into the future, What version of the Amplitude story from here is most exciting to you? Like, what is the vision for where to take the business relative to where it is today?

We're in 20 of the Fortune 100 today, and I would love for us to get from that to a majority of the Fortune 100. The way I think about it is there's going to be a data repository or kind of a brain that powers all the different products we have. So right now, when you're using a product on your phone, It's what I think of as static. So press something and then does the same line of code no matter who you are and what your previous history with the app is. Over the long term, you're going to see software that will adapt more proactively to you as a user. There's going to be a company that builds the infrastructure, and so our goal is to be that company, is to basically help you personalize and create the ideal experience for all your end users. So we're in the really, really early days of that. I mean, we passed $100 million in ARR last year. We're now continuing to grow. But on the scale of these things, if you look at where the largest SaaS companies are, Salesforce is in the $20+ billion range, and there's a few others there. And so that's very much our aspiration over the long term. If we do this right, where we become the infrastructure behind all these great products, then we absolutely have the potential to be. The other thing I will say about that is like, One of the other ways that I kind of look at the SaaS market is like there's basically a big company that sells to every single buyer out there, right? So Salesforce does sales, Adobe does marketing, ServiceNow does IT, Workday does HR, etc. No one's built something for the chief product officer. And so our goal is to be that thing that builds for them, that builds the data-driven product and everything that they need around that.

If that all comes true and there is this sort of brain that makes products more personalized based on data, in what ways do you think that makes the world the most different from the perspective of the average end user of digital products, or I guess of any products. It makes sense. It all sounds logical and the arrow of progress is in that direction. But what do you think is the most interesting potential thing that unlocks or way it makes the consumer or customer experience different in the future versus today?

Basically, it's this huge lever on our time and interface with technology. So today you have these things where it's the exact same experience for every single user. Kind of no matter what you want. If you can get software that starts adapting proactively, I think you get a bunch of different things. First, I think you can eliminate a lot of the frustrations that people have. Like, how many times have you been in software that's incredibly frustrating to use? Whether that's, hey, I'm trying to reset my password. I spent an hour the other day just trying to reset my password on United because I had one account, but it wasn't linked with my flight. And it was just like, man, that was an hour waste of my life that I would love to get back. Where, hey, smart software could have done a lot better job. That's one. Another thing is proactively understanding me as a consumer and what it is that I want and what I'm likely to need. If I know, hey, I'm going to be traveling soon, I know that I'm likely to need a ride, can you proactively set that up for me so that I don't have to worry about it? Can you proactively order groceries for me, or can you proactively suggest things I'm interested in, whether it's things I'm likely to buy or content? Movies that, you know, I like to watch or information that I'm likely to need. Hey, you know, if I'm about to do a podcast with you, Patrick, you know, I'm likely going to want to look at the emails that we just wrote back and forth to each other and the context has been set up. And so all these opportunities for software to get smarter and a lot more personalized. And the way I think about that is it's all about us as human beings just getting more leverage out of the software we work with. Think of Google today. Google's done a phenomenal job of this where it's like, There's a bunch of research that shows that information recall for things that you can Google is actually worse. But I actually view that as a great thing because we've outsourced a huge part of our brains to the web and we can look up all sorts of things really, really easily as a result of it. And so it's actually made us a lot smarter as human beings in a society. So now it's like, instead of thinking of me as Spenser and just my brain and what I'm doing here, it's like, no, no, I think of Google is one of these tools I have an extension to. I think the same potential exists for all software out there where it's like they become further extensions of who we are as people and give us tools to become more leveraged. Now, I know I'm speaking in very, very abstract terms here, but I think that's the end state. I think you already see it a little bit. My wife, put her on the spot here, her name is Anne and she really loves Korean dramas. And so she'll be on Netflix. She got suggested one the other day, ends up being one of her favorite shows. That she ended up watching end to end. And so she got a bunch of value out of that. That wouldn't have happened otherwise if Netflix as a product hadn't adapted to her. That's kind of the future world that we're at the very, to be clear, at the very, very early days of. We hope that we can bring sooner.

Spenser Skates: Spenser, this has been a really interesting conversation. I think normally my founder conversations are more about the entire chapter-by-chapter story of the business. What I think has been cool about this one is just talking about some big broad topics that apply to every company, but I think probably most people in most cases just do what other people have done. Right? And so I think it's cool the way you attack some of these big ideas. I ask everybody the same closing question, and that is to ask, what is the kindest thing that anyone's ever done for you?

So many. I wouldn't even be close to here today if it weren't for a long line of very generous folks that for no other reason other than to be kind, were willing to share their expertise and help. I'll give one example. When I first came out here, we hadn't even gotten to YC. I was just this kid with a dream and an idea. But one of my classmates from MIT, this guy named Matt Huang, he had just done a startup and he gave me tons and tons of advice for nothing in return to himself, just to help me navigate and orient and understand who's who and what's what and what I should work on and how to navigate things and how to build a business. And as a result, I probably would've gone on for longer in the failure phase and may not have even gotten it by far if it weren't for his help. And so he would Gchat me or call me a few times a week for about a year, even though we were nobody and nothing at the time. And so that was incredibly kind of him and felt really lucky to benefit from that.

Would that be the same Matt of Sequoia and Paradigm fame that I would know?

That's right. That's right. Both of us were kind of, I don't want to say nobodies, but basically when he first came here and he had this failed startup. And since then he's been incredibly successful. Yeah. Got on to start the leading crypto fund and he had one of the most successful angel funds of all time. And so it's been cool to see both our careers rise in parallel.

I might put Matt, sorry if this annoys him, but I might put him on the same Eric Vishria list of the good ratio of quality to PR campaigns or something, someone that should be better known. A really, really thoughtful guy. So great closing thought, Spenser. Thanks so much for the time today and all you shared with us.

I appreciate you having me on and thank you for the time.

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