The Boost VC Podcast with Adam Draper: Episode 98 - Spenser Skates @ Amplitude

Welcome to the Boost VC podcast. At Boost VC, we are the accelerator that invests the first $500,000 into sci-fi tech startups. And this show is all about talking to investors and founders to dig in the latest topics around sci-fi tech and building great companies. I'm your host, Adam Draper, founder and managing director of Boost VC. Are you ready to rock? Look, this conversation is recorded sort of as a live podcast where we invited just a small group of the Boost VC network to participate, but also just be there while we were listening. So most of the advice Spenser feeds out is related to the beginning of the story of starting a business. However, I believe that this podcast has everything you need at the beginning of your story, at the beginning of your business. Spenser Skates is my favorite founder that I have backed. He represents sort of a mastery of each step and phase of the process. He has built a successful business that is doing $100 million in revenue, and he also is able to surround himself with the best people who can help him master that. So I am really, really excited that we got to have Spenser on a live podcast for the Boost VC podcast., and I hope you enjoy. Spenser, welcome to Boost VC digitally, and thank you for coming. Spenser is— I was talking about this before, but he's my favorite founder, and I can say that with verifiable certainty. When we met, they were a company called Sonalight. So Spenser and Curtis, the two founders of Sonalight, which was a voice-to-text company that had 500 users and they had 15 different charts tracking those 500 users. And then they evolved. They realized that analytics was going to be their— they realized that they had a forte in technology, that they were able to be able to deliver great analytics. And so they jumped over there 2 weeks after I had invested. They came to me worried that I was going to pull my money and they said, hey, we're actually changing our business completely. To analytics, very excited to stay invested. Spenser since has built a huge business, moved from pre-product to sales and focused. My favorite thing about Spenser, the reason that he's my, I'm going to say my favorite founder, is that every time that there's a moment of scale, he focuses very, very hard on what he needs to become in order to scale. And like, I remember it very clearly with sales. Also, he's just enjoyable and pleasant to be around. So welcome, Spenser. Thank you for coming. And yeah, how's your world?

Awesome. Thank you, Adam, for the intro. That's very, very, very kind of you. You know, Adam was actually one of the very first angel investors into anything I had built ever. So huge credit to you to seeing us early. I remember it was so hard for us to fundraise at the time. This was like 2012, and things were not as kind of hot as they are now, and it was definitely harder to kind of put something together. And we didn't know, we were just kind of just two kids out of school, and so we didn't know, we didn't have any idea about what we're doing. But Adam believed in us and what we were doing, and yeah, it's been, it's been great since.

So how do you explain what Amplitude is today?

What's— yeah, yeah, let me give, let me give a quick overview of Amplitude and my story, and we can go from there. How's that sound?

That'd be great. Awesome.

Well, firstly, I just want to say great to meet you all. I'm really excited to talk to everyone at Boost. I think I've done this a few times before and it's always really enjoyable to get to meet you folks. For me, the biggest thing is like, how can I be helpful? There were a lot of incredibly helpful people when we were early on. Adam was super helpful. There were a bunch of other founders who volunteered their time and so for me, just figuring out whatever questions I can answer or what have you to help you guys think about how can you build a successful business, I'd love to do. With that, just a quick intro to myself. So I graduated from MIT in 2010 with my co-founder. We started working on startups in 2011. We did Sonolight, as Adam said, and we kind of didn't really know what was what. We were just like, hey, let's pick a hard technical idea. And so we came up started a voice recognition company. This was actually around the same time that Siri came out, so voice recognition was just starting to become a real thing. It was, in retrospect, that the problem was actually probably a little too hard for two engineers to tackle. There's a lot of really crazy kind of machine learning and deep learning stuff in order to create great voice recognition, but we tried it, you know, we did that for a year, did Y Combinator, launched the product. We actually, actually coming out of Demo Day, I remember for Y Combinator at the time, we had the most press coverage out of any startup in our batch. So we had like something like 10 different press articles about us, which was like way more. Some companies wouldn't even get covered. We raised from a few angels, including Adam. Adam was the first person to kind of believe in us and put money in. And then, you know, we kind of realized that the retention and the engagement, like how good was our application and how much would people use it and how like How valuable was it to them? Like that combination wasn't good enough to create something that would grow in a big way over time. So we ended up shutting that down. We came on to, we had spent a lot of time building our own analytics in-house and we saw that there was a big need in the market versus what was out there. So we started Amplitude. Amplitude is product analytics. So it helps you understand the end-to-end user journey. We wanted to know, for example, how important was to link the accuracy of the voice recognition to long-term engagement in the product. Facebook at the time had a famous study where they found that the most important thing a user could do was add friends. They found that if you got to 7 or more friends, you were likely to become a long-term user. And so we said, hey, let's create a product that can do that because nothing on the market could do that at the time. So that was the start of Amplitude in 2012. We launched the company in 2014 and been scaling it since. Raised a ton of money in the meantime. Today, we're just over $100 million in annual revenue, still growing a lot, on the track to, if things go well, potentially IPO in the next year or two. So very, very different sort of scale and problems from way back then. But yeah, still on that path to try to take over the world from where we are.

And that decision, the decision for At what point were you like, Sonolight doesn't work?

Yeah, I think the biggest thing was like, we weren't super passionate ourselves about the product. And so that was kind of a big stumbling block, especially for making a consumer app. I think the other thing was that, like, we saw the quality of product we were able to make in terms of the accuracy of the voice, how engaged users were, was not going to be enough to make it like a to grow as fast as you want to grow as a startup. So we kind of saw the path ahead where after doing it for a year, we said, hey, we could spend 3 or 4 more years on this thing, but if we did, it would just kind of be a mediocre outcome. Like we probably would maybe get to a user base with maybe 100,000 users, be an okay app, but it wasn't really any path towards like a massive scale.

I remember you rationalized, you told me when you were changing, you said the tech for this is 5 years out.

Voice recognition was too early. Even now, it still might be too early. All the big public tech companies like Amazon Alexa and Google has a thing, it's not clear if they're going to be massively successful in the same way previous new technology has been. It's a little bit too early and people aren't used to it. We're used to screens. We got PCs and we got phones and all that, like that works, like that interaction method works. But the idea of voice as an interaction method for technology, it just hasn't quite— the UI is just a little bit too challenging. You know, it's like you have to say something, it responds back to you, you're waiting, you kind of don't know what's going on. Like everyone wants like the Iron Man suit with Jarvis in it, but it's just not quite there yet.

Everyone does, especially me.

Have you built a suit for yourself yet?

I knew that was like a— We've invested in about 70 AR/VR companies and then also invested in 2 jetpack companies. Funny enough, last week, I'm not sure if you saw this, but there was a sighting of a jetpack 3,000 feet in the air off of a plane.

Yeah, I saw you said that was you. Was that actually you?

No, it wasn't actually me. I realized that I shouldn't have said that because Basically, I had like 20 people reach out before that tweet saying, "Was this you?" And I was like, "I branded myself perfectly. This is amazing." But then, I was joking when I said it was actually me, but it wasn't. Evidently, sarcasm doesn't come across in—

It's hard on Twitter, man. You never know.

Yeah, you never know. I wish it was me. There. That's what I wish. I wish it was like right at the beginning of Iron Man when he tries the suit for the first time. I wish it was that moment for me, but it wasn't there yet.

One of the things I will say to this group is working with Adam, you are absolutely— Adam is like, what I love is that you are the crazy frontier idea guy. I remember you were the first into Bitcoin, the first into drones, 3D printing, AR/VR. It's like, in terms of the best collection of people working on frontier technology, this is it. You guys might feel like you're super early and like you're still trying to figure like lots of stuff out, but like, this is it. Like, if you guys are going to invent the future of this platform, you know, the next Google and the next Microsoft and the next whatever of AR and VR and all this stuff is going to come out of here. Like, I, yeah, it's like, it's just, there's kind of nowhere else in the world that's as good of a collection of people working on it.

Thank you, Spenser. That's awesome. I was hoping I was only going to compliment you and not get received, but I, you know, I'll accept it. I'll accept the compliments. Thank you very much. That was very kind. You co-founded this with someone. Yes. Why was he a good complement to you?

I got very lucky with Curtis. So yeah, let me tell you the story, which is that like when I graduated from school, I was trying to convince, you know, I knew I wanted to do a startup and I was trying to convince anyone and everyone who would talk to me that like to come do a startup with me, but nobody really wanted to, you know, they wanted to go get the safe job at Google or Facebook or whatever, you know, or go into finance or, you know, take the safe career path. And so Curtis was like the one person who would say, who said, hey, you know, I want to, I want to do a startup with you, Spenser. And he said he wants to learn how to build a business one day. But he wants to go work for a year at Google first. And I'm like, man, if he goes to Google, there's no way he's ever gonna come out. They got the free food and the slides and the ball pit. It's just so hard to pull someone out. So the first year after we graduated, I worked full-time, I got a job full-time in finance, 'cause nobody wanted to start something with me. And on weekends, I would just work with people on just side projects. And we worked on all sorts of, all sorts of stuff. We worked on a website for photographers, like that was supposed to like replace Craigslist so that if you wanted to find a good photographer, we worked on like a website for our graduating class so that you could see where people went after graduation. We tried to do like an outsourcing website. We worked on all sorts of stuff. Like we probably did like 5 or 6 different projects over that time. But the important thing was we were working together and Curtis was the one person who was kind of constant during that time. You know, other people came in and out, you know, with us for very weeks, but Curtis was the one who had stuck through. And it finally got to the point where we were coming up on a year of him working at Google. And so I'm like, man, like, okay, like, you know, now's the time. Let's get him to, let's get him to leave Google. So I quit my job. I was in Chicago at the time. I called him up and I'm like, hey, you know, we're doing this, right? You're gonna quit? Like, that's all good? He's like, yeah, yeah, yeah, I'll quit. So I moved out to California, you know, just by myself. I moved in with Curtis. I got a mattress on his bedroom floor. He, to his credit, he quit. And since then, we've been working together for like 9 years now and it's been phenomenal. I'm very, very lucky to work with him. It's really hard. I'll say this, it's really hard to find a co-founder that works well. Most common problem where startups fail is because of disagreements between co-founders. There's so many things that you work together on. That like, you know, just because people are different from each other, you're going to have conflicts and disagreements on, and it's really hard to figure out, you know, how to make it work. People compare it to getting married and it's very true. It's like, you know, you have to have deep trust in someone over a really long period of time and you have to have deep respect and you have to be able to both contribute value and to find that match on all of those things is so, so hard. So For those of you where you're still searching for a co-founder, my biggest thing would be like, yeah, you can't— waiting a year for the right person, totally, totally worth it. One of the things that Curtis and I agreed on was that we'd give it at least 2 years no matter what together. Now it's been 9 and so it's gone way better than any of us could have thought, but that's one of the places I see a lot of early-stage startups make mistakes is that They'll say, "Hey, we'll try this out. Let's try this out for 6 months or 9 months or a year. If it doesn't work, we can go back to grad school or we can go back to our job or we can go back to doing something else." But one of the really interesting things is before we started, I read a lot of different stories about just successful startups. What were their really early days like? What was it like when it was just the co-founders? And one of the things that stood out was just how hard it was and how awful it looked, where by most standards, you should have quit. Some of the stories that you read, like Airbnb, where it's like they created cereal boxes to sell that were election-themed back in 2008 in order just to fund their living expenses because they were trying to make this airbed thing work. They stuck at it. They stuck at it for 2 years before they figured stuff out. They got into Y Combinator and started figuring stuff out. You know, that's suit every single startup. I mean, we, you know, we failed with Sonolight after a year, but it was no question we were going to continue with it. So that mindset where everyone is saying, hey, we're here and determined for the long term, kind of no matter what, you know, that's just super important. You don't have to say, hey, I'm going to do this for the rest of my life, but like saying, hey, I'm going to really work hard and I'm willing to do this with no success for many years. Like that's, that's super important because that's what separates like, Probably 50% of the, you know, they say 50% of success is showing up. Like, that's that 50%. Are you willing to do it with no success for multiple years?

What do you think? 2 years is a good amount of time to sort of like commit before?

Yeah, I mean, I kind of didn't. I'd say, yeah, minimum, at least a minute. That's kind of the minimum, I would say.

And what do you think you were lucky about with Curtis that made it work where other people had failed? You said, you know, you were saying That's where most founders sort of have the most problems, broken up the most, like failed. Where was the actual value? Was it in the fact that—

It's hard to put it to one thing. I mean, we're close friends from college, so that definitely helps a lot. We had worked together on projects before. We had done a bunch of coding competitions before.

Having the experience before actually is sort of interesting. Not as many people— some people just go like, "Let's start it together," and then they—

Yeah, yeah. Helps. It's kind of like dating before you get married in a lot of ways. But other forms can work. Arranged marriages can work. There are successful couples who do that too. So I'll say a few things. One is just who is the CEO and who is kind of the ultimate shot-caller in the thing. That's a super common source of conflict. So both people having a lot of humility around that is really, really important.

And how did you two decide that?

I was kind of the one, you know, whoever's putting more energy in driving things tends to be that one, but I didn't have that much ego about it. You know, I told Curtis early, hey, if you want to be CEO, like, you know, like I'm fine, you know, great. Like, you know, I just want to work with you. So, and I think to his credit, he, you know, he ended up saying, no, no, no, you're the right person for it. But in the early days, that doesn't matter. But like over time it will, you know, especially when you're early team. Another really common one is like, how long do you work on things before you give up? Or how do you get positive energy? It's really hard. It's like you're the only source of positive energy because like, you know, your friends, like everyone around you in your life, your friends, your previous classmates, you know, your parents, you know, your, your, you know, whatever. It's like, they're all like, you know, posting on LinkedIn or Instagram how, what amazing lives they are. And they just got that promotion at work. And like, you know, they're, on this really cool trip. And it's just like, okay, you, you know, you have nothing going on. It's like, you're just two people working and you have nothing to show for it. And so you have to be able to just not listen to any of that and just have that, that kind of self-confidence. It's much easier said than done. Like I was talking, I saw, I have an executive coach that I've been working with for about 5 years now. And one of the things she said was that the most people she works with have kind of the existential doubt over them. Where they're not sure if they're going down the right path or they're the right person for the exact job, and then someone reinforces that doubt externally being like, "Hey, are you guys sure you need to be working? This is a good idea for you to be working?" And then it'll mess with their head. I kind of knew it's like, you just can't care. You just can't care what anyone thinks. You can't. And eventually you'll find people who believe in you like you, Adam. All the co-founders having that mindset. Most people don't and aren't cut out for it. The idea that you have to work with no external validation for many years as an early-stage business.

On that sort of topic, where does your energy come from? Where is the fun part of your job that delivers the energy to the rest of the organization?

It's hard, honestly. It's still hard. That's still something I'm getting used to. Now that we're large— when it was just me and Curtis, it was honestly, it was just— I'll say in the really early days, it was just fun to work on stuff with him. And like, yeah, my mom was skeptical and his parents were worried about him. My mom's Asian and his parents are both Asian, and so they got the, oh, why don't you get a high-paying job like your cousin? It's like, that's the thing. So we both had to have enough self-belief, and Curtis, to his credit, has a ton of self-belief. And so that kind of, we fed off each other, and it's just fun to work on cool stuff in the early days. Now, once you start growing out the team, what you'll find is all problems are people problems where it's like other people aren't going to work out and so you have to change them out or fire them or bring in new leaders or whatever. And those, I don't know, at least I'm not, that's not a natural thing. Some people can do it, but that's not a natural thing for me. And so that's definitely painful. But when it's in the early days with a really great team that you trust, it's like that's just a ton of fun.

And how is your job? Yeah, so basically, I mean, you and Curtis have It was just fun, like you guys were—

Yeah, it's just we're working on stuff and we knew we were gonna do it for 2 years no matter what, and so like, even if one of you failed, it's fine, we're just, we're still gonna do it, you know?

Yeah, and so like that was what powered you through, and then eventually you started to really narrow in focus on this one problem. You know, there was Mixpanel, there were a bunch of other analytics players that people would point at, or Google Analytics even. Like how did you start to pick away at, and who were your first customers? Like how did you close a first customer? How did you get someone to be like, yeah, we—

oh man, I was so bad at it. I was so bad at sales, you know, so I'm an engineer, you know, that's how I started, but I had to learn how to go sell. And I remember, you know, I thought the way you did selling was you kind of show up to the demo and ask for money, but it's actually very, very different. Yeah, I remember our first customer was this one, this guy named Brett, and we got intro through one of our investors and they said, hey, you know, meet with Brett, you know, he'll evaluate your technology. And he was this gaming guy and we were just, we had nothing, you know, we had a bunch of people using us for free, but that didn't really care much about what we were doing. So we went in, we gave him the demo, you know, he asked a bunch of questions and then we got to the end and he asked the question, hey, how much does it cost? And I'm like, dude, I've never been asked this question ever. Someone is like thinking about how much money to pay me, like what, like what is this? And I'm like, okay, okay, what's the rule? When you're selling about how much it costs. And like, oh yeah, you always undercharge, so ask for more. And I'm like, hmm, I was thinking about like, okay, maybe I asked for like $100 a month. And I'm like, you know what, that, that's too little. I'll just ask for 10 times that. I'm going to ask for $1,000 a month. So I said, hey, it's $1,000 a month. He was like, whoa, that's so cheap. And I'm like, awesome, amazing. Like, this guy wants to buy it. So that was like, that was the very— and he was willing to put up with a crappy early stage product because you know, he wanted some of the things that we could do that he couldn't get anywhere else. And that was our first customer. And then it took about 6 months to get the second customer. But then I, by that time I had hired like a full-time sales coach that was, you know, working with me once a week to coach me and teach me sales. And I learned much, much faster by doing that. And then we grew from $1,000 a month to, you know, the second customer was $2,000 and then it was $3,000 a month, $4,000, it was $8,000, $10,000. You know, we eventually got to doing about a million dollars a year. A year in revenue after the first year.

Yeah, so okay, well it sounds like this sales coach was good, right?

Sales coach, yeah, a guy named Mitch Moreno. Did I ever introduce you to him? No. He's really good. Once you have something that you can sell to customers, he's probably gotten, I don't know, 15 companies from $0 to $1 million in annual recurring revenue. So if any of you guys are at the stage where it's like, hey, we're ready to start selling this and asking for money, working with someone. I'm happy to introduce you. I'll send you his—

Yeah, please send over that information. But also, how did you find this person? Did you just ask a couple people for this person?

Yeah, it was random. It was like, he was working with another founder I knew who was— they were also an engineering team and they didn't know anything about sales and they were trying to learn. And I'm like, you know, these guys think he's good to coach on this, you know, he's probably good enough. So I just went up to him like, hey, I want to work together, how much do you cost? And he's like, whoa, whoa, whoa, let's slow down. Let me understand what you're trying to do. But I kind of knew, like, hey, I know nothing about— I was just like, hey, I know nothing about this, I want to learn, can you help?

So sales was one of the things you had to become, like, you had to learn that muscle, right?

Yeah, so that was the first thing. That's also something I recommend here. So I don't know what everyone's backgrounds here is, but both Curtis and I are engineers, and so that's what we'll spend time on. It's like building stuff and getting it out, and that's what feels good, and that's what we know how to do. But if the other equally important part, it's like that's just half of it, building a great product is just half, the other half is how do you get it to customers. And so if you're selling to businesses, that's sales. But even if you're doing a consumer product, you should be spending half your time talking to customers or supporting them or engaging with them or what have you. So yeah, it was just like when we launched the company, I knew that sales was so important and I saw so many great startups who had great products and great engineers and great teams just fail because they weren't willing to do the hard work of learning how to sell the product.

Do the hard work of selling. I'm going to write that down real quick. Do the hard work of learning to sell. Learn to sell. I think that's right. I think that there are great teams with great products where they think if I build it, they will come, or, and they won't do the hand-to-hand combat, right? Yeah. And that's a fascinating point too.

It's just, you know, one of the famous stories from Y Combinator was Airbnb. What they would do every weekend was they would travel to New York because that's where their users were, and they would just like talk to them. You know, they had like 5 people, 5 users, like that's it, like 5, you know, and they would literally fly out to New York just to talk to them. And then from there they would learn, okay, cool, like this is how you heard about us, this is why you're using us. Hey, do you know anyone else like that? Oh, you know so-and-so, great. And then they'd get like, or they get someone to host a party to share Airbnb, or they just hand out flyers in the subway. It was literally like, you know, this is how they're trying to get people to use, like they try all sorts of crazy things. But the point was that like, you know, they were spending half of their time and energy just like talking to customers, talking to— and so that's the one thing I would think about as you guys are building your companies, which is how am I allocating my time? Half your time should be building your product and half your time should be talking to customers. If it's not, like a lot of times, especially engineering teams will spend like 90% of their time building their product. And that's a huge mistake because the amount that you learn about like what customers want and what, how you can improve your product and how you can get more customers is just so much. And what that looks like for B2B companies, that's sales. For Airbnb, it's like talking to people in New York. You gotta figure out where your users are and just literally, if you need to fly out to them, well, maybe you can't right now, but when coronavirus is over, go out and fly out to them.

Well, and with ingenuity, you can probably figure out how to get in front of your customer right now, right?

Yes, exactly. That's the other thing. Figure out how you be creative.

So that's, that's what the Airbnb story really represents is like they on Saturdays and Sundays, they were just like, we're going to go talk to our customers. They're in New York. We'll go fly out to New York. We'll go talk to our customers. For your first customers, how did you decide on sort of long-term category sector or market? Like, you know, you had, you couldn't get Microsoft right off the bat or you couldn't get— where did you settle where you were like, we're going to take ownership of this section of the market and try to— yeah.

Yeah. The early group that really I mean, the truth is in the early days, you'll sell to anyone who's going to buy or who's going to talk to you. That's kind of what you do. But the group that found us was— so the first guy I mentioned, Brett, who is like a gaming company, he was a former product manager at Zynga and there was kind of like a mafia or like a group of other ones of them. So we asked him, it's like, "Hey, is there anyone else who might—" and so he introduced us to kind of 3 or 4 people.

And we talked to them. So your customer truly became your sales organization.

Yeah, yeah, in the early days, yeah, yeah, yeah. They're not gonna sell for you, but they'll at least say, hey, you wanna talk to us?

Well, if they like your product enough, they'll at least say, hey, these, you should talk to these people.

Yeah, yeah, they're willing to do an intro. You have to do like, you know, 99% of the work to make the sale, but they'll at least say, hey, you know, here's a direction you might wanna look at.

The thing that's different about you is that not many people ask that question to the customer. Not many other people will actually ask that question. They won't go to their customer that they were like, oh, thank you for being our customer, and say, hey, actually, can you do a little work for me and like connect me? Yeah, well, just—

I think, I mean, it's like you got to ask it, you know. It's like you, you want, you know, once they like your product and once they get value out of it, you'd be like, hey, who might you recommend, you know, this to? Or who do you rec— Who do you think? And then make it easy for them, that's the key. So you're saying, oh, so-and-so, cool, can you make an email intro and I'll do the rest? Or if I reach out, should I just reach out? Just figure out how to make it easy for them, but the key thing is they can point you to other customers. It's like they're not going to do the work of selling it for you, that's one of these startup myths which is so damaging. It's like, oh yeah, we get by through word of mouth and we don't do any work to distribute our product, we don't have any marketing. It's like that's the biggest lie there ever was. Nobody is going to sell your product for you, it's like no matter how good of a product you have. What they will do though is they can point you in the right direction. So they can say, hey, you know, oh, like, you know, I know there's a community of like VR people that are really into, you know, X, you know, you might want to go talk to them. And so that they can at least give you the right direction to go in, and that's incredibly important.

So as, as your organization has changed, how's your job changed from like, how do you think about like the eras of Amplitude as of now?

Because it's been— yeah, it's so different. I mean, The Sonolite, that was like 4 or 5 lifetimes ago. Yeah, I'll break it down, which is first few years trying to find a product that just had people wanted to use, and it took us about 3 years to get there. Then after that, it was about sales. So how do I sell this thing? And that lasted about another 2 years. And then it was about how do you grow the team? So once I sell, You know, it's like, and once that works, once you get to a million or a few million, it's like, okay, you know, you probably want to get more help selling this. And, you know, it's me selling it, it's not going to scale. The trouble is like, yeah, no one is going to be ever as good as kind of the founders in selling it because like, you know, they're the ones who created it and they're the ones who have the most passion. But you can find people who are actually really good and better in other ways. And then so you grow the team. And so, you know, I came from salesperson to running a sales team. And then from there, it's like, then you hire executives, people who are explicitly more experienced than you to scale your business. And that's probably when you're like 20 to 30 people that, and then they hire, you know, executives don't actually do any work themselves. They just hire other people to do the work for them, but they're very good at that. And that's a skill too. And then you realize later on that, you know, the executives you have are good for like the early stage, but not the right people for the later stage. Then you have to hire new executives and bring them in. And so where we—

It's like a game of leveling up.

It's like a game of— I'll say this, it's at like the kind of, at the executive level at these scaled companies, it's ruthless. It's like a professional sports team. And so if you can get a better quarterback, even if you love your old quarterback, even if he's Tom Brady, you're like, salary cap's too high, I'm gonna go find Cam Newton instead. Instead. It's really like that. It's some Game of Thrones stuff. But that's what the job is. They know that, that they sign up for it. That's kind of one of the— if you're operating at the top, it's just like you could get replaced anytime. So yeah, we changed out the entire— we changed out our head of sales, head of finance, head of engineering last year because we knew, hey, we needed to grow the team. We're now at 100 and we're trying to go to 500 and we're thinking about how do we get leaders who are good at this stage and going from there to the next place. So yeah, so that's the current thing. So yeah, going back to the early stage, that's like many lifetimes ago.

Yeah, I know. But it's fascinating to think about. There's this inspiration that is the product and the customer, and then like it slowly becomes how do you get more customers?

And then it's how do you get the people who can get the people to go get more customers? And then how do you get the people who get—

So how have you— so in the way that you sort of mastered the sales, and I'm not going to say you mastered, but like you got really great at selling and you built a business. So yeah, you mastered the sales. How have you thought about mastering sort of management? Do you still work with— is it the same coach that has been able to—

Yeah, yeah, yeah, yeah. The coach is one part of it. That definitely helps. Yeah, it's hard. I mean, first thing I'll say is it's hard and nobody's done it. You know, if you're doing it for the first time, you can't really learn it without doing it and failing. And so at sales, like, you know, I didn't do a good job for quite a while. You know, it took me a while, even with the coach, it was hard to learn. And then same with hiring executives. I had a bunch of mistakes on that. Like I probably didn't hire, you know, I probably held on to executives that were not working out for way too long and it cost us, you know, we could have grown much faster as a business if I hadn't done that. But it's just like you kind of know no other way besides doing it. That's the first thing, both with sales and with hiring a team and with hiring executives. Any of those things, you can't really read it in a book, unfortunately, like you can with coding. You have to learn it by doing it. So that's the first thing. Second thing is, given you know you're going to try it for the first time and fail and it's going to be hard, how do you learn faster? And so that's where experts who have done it before can really help. So who those experts are can change, can be different. We hired the sales consultant or I have an exec coach now, and so those have been good. We have one of our investors, I would say most investors don't know how to scale businesses, they haven't been operators, but there are some that have. And so we have one, Eric Bichery at Benchmark, who's been really good and who's been kind of that mentor for me. As we've grown, you kind of get it from different places. But I guess maybe one way to think about your time is like, you know how I said spend 50% of your time building, 50% of your time talking to customers, maybe spend another 10% of just, just only 10%. So not a majority, but 10% on just like finding experts or just talking to people who have done it before. So people who are, you know, maybe 2 to 3 years ahead of where you are just to learn from them. Other startup founders are great. For you guys, other startup founders are really, really great and generally really willing to talk about stuff.

Yeah, so you mentioned investors, and you have a great slew of investors. Your psychology around investors probably changed from when you were just a product and you were desperately needing money from someone like me to over the course of time— I don't even know how much money you've raised now. How much money have you raised?

Probably around, I think it's close to $200 million, something like that.

Yeah. You probably think about investors differently over the course of that time. What are some ways in which, if you were at the beginning of the— obviously everyone in the room right now is sort of at the beginning of their journey. They've raised some money from us, but over the course of the next couple of years, they're going to probably go try fundraising, try building to have customers and stuff. What would be the best way to think about investors in general?

I mean, there's been a ton said on that, so I don't think there was anything super surprising for us. We raised kind of party round from a ton of different, like 30 different investors from our seed, and that was a mistake in retrospect because there were probably like 5 or 6 that were helpful, like yourself, Adam, and that spent time to get to know us, but most didn't. So focusing on like, okay, let me get a few that are actually going to help me and get deep and advise me, that's my preference. That all said, it's like money's money, and so it's like however you can get it, that's the much more important part. When you need to grow out the team. So it doesn't really matter exactly how you get it, it just matters that like, you know, you get some.

The best people who have been so helpful to you, like Eric from Benchmark or whatever, like how do you find those people? So like what's your route? What do you have a process where you're sort of like, okay, I know I'm weak here, I'm just gonna start reaching out to random people who I know who sort of—

I'm actually not very good at this, but I Yeah, I think Eric was just lucky. We got an intro to him, we gave him the pitch, and then he gave us an offer and we were deciding between him and some other offers and we did a bunch of references and him and Benchmark were the strongest by far. And so it was like, okay, let me work with them. That's for Series A, which is kind of a little later stage. For early on, it's just like, when you don't know, like the key is, it's one of these things people talk about networking or building your network. Just finding other people who are good, thinking about asking them for who else they think is good, spending time building those relationships and getting help on it. Some investors are going to be helpful, some are not, so spending time with the ones that are helpful and thinking about what relationships you want to invest in to build stuff out. There's not a, "How do you get?" I don't know that I have a good formula for it.

So looking back, not even looking back, looking forward, I guess, what are you most proud of that you've built and then what are you most excited about going forward?

I'm really proud of the team that we built. I don't know how we got really lucky with some of the people that we brought on, and that was really hard to do right. And because of that, the culture and the org and the mindset they've built, it's like that is like, I hear just horror stories from other companies about that. And so I'm really, really proud of what we've done there. Looking forward in terms of what I'm excited, I mean, one of the fun things about startups is that it's an infinite challenge. So no matter how big you are, you still are going to try and grow bigger. And so even at this stage, we're thinking, how do we get from $100 million to a billion? And once we get there, it'll be, how do we get to multiple billion? And it's just like, there's kind of infinite number of challenges and infinite learnings. And the great thing about startups is, so the challenge with startups is high risk, right? You don't know if you're going to build a good business at the end end of the day and you're kind of staking it all. Whereas in a regular job, it's like people pay you money to do the thing. That's the challenge. The good is that it's not just that you kind of get this great upside in terms of money, but it's that like, you know, there is no faster way to learn stuff than by doing it, you know, doing it all yourself. It's hard and it's scary and kind of everything else, but this is the best way to learn like any skills in life. You know, Curtis, the reason Curtis wanted to do a startup was because he wanted to learn how to build a business. And it's like, has he learned yet? You don't get that from anywhere else. Has he learned yet? Yeah, he's really good. You know, he, to his credit, like most CTO technical co-founders don't learn that, you know, just stick with the engineering, which is good and valuable in itself. But he actually served as our interim head of finance for about 6 months while I was doing an executive search for that. That's actually one of the other hard things is like, it takes a while to hire an executive. It's not like you can just hire one, they show up. You have to like make do with a kind of crappy interim solution. So Curtis was actually, you know, actually did a really good job as our interim head of finance when we were looking for one. And he also did one as our interim head of HR, which was also fun. And he was actually, it's, he was actually pretty good at it. So he cares. I love that. Curtis is like a very good, like, hey, yeah, I'm gonna do whatever's right for the team or right, you know. I'll fill in the gap.

Let me go fill in the gap. I like that. So some of the companies have been asking questions here. Any thoughts on knowing when to hire someone for a task versus contracting out or keep doing it yourself?

So, you know, in the early days when it's just the founders, you should kind of do everything yourself. Anything that's building the product or talking to users, you should do, and anything kind of outside of that, it's like you don't really want to spend time on. There's like some basic stuff like legal entity setup and all of that, like obviously, you know, go hire a lawyer to do that. Don't waste time trying to figure that stuff out yourself. The one thing we outsourced in the early days was design. So we hired designers to make our website, but everything else we ended up doing it ourselves on things. Any part of building the product, that's the core thing and it wouldn't make sense to outsource or trying to sell it. I know a lot of founders are like, "Oh, can I outsource the sales to somewhere else?" "Can I hire this?" It's like, "No, no, no, you have to do it.

You're never going to be able to outsource that." And what was your first hire after you and Curtis?

We hired Jeffrey, who ended up becoming a kind of third co-founder, who was an engineer. And then we also hired Alan, who was kind of a— he was just like one of a friend of mine from high school who was just very smart, really hard worker, not an engineer, but we ended up putting him to work on the customer success side. I would recommend, yeah, it should be your first hire or two should be an engineer or a salesperson so that you can build more product and sell more of it. It's not until you get to like 10 people that you even think about kind of anything beyond those two things. Cool.

Here, I'm gonna ask you goofy questions now, ready? Yeah, let's do it. Okay, I call it the lightning round. So lightning round.

All right, we'll do it quick.

Okay. Well, sometimes it's quick. You're trapped on an island. You can only eat burritos for the rest of your life. What game are you playing?

What game are you playing? Oh, bring— I can only bring one game on this island.

Well, yeah, but basically I set it up with you're eating burritos for the rest of your life. But what game are you—

what game is it? Oh, okay. I got it. You know, I— so I've been— I don't know if anyone here has been playing Valorant, but that's been hot recently. The one that's really good though is Minecraft. It's just like, it's the depth of it is just crazy. You could play that forever. It's gonna be, it's so good.

What? I have never played Minecraft and I should. Dude, what the fuck? Yeah.

How are you the AR/VR guy? You gotta play it.

Like it's just the thing, so. That's true. Okay. What is your favorite song to jam to when no one's watching?

I love Lady Gaga. I'm a Lady Gaga fan.

That's fantastic. I would have guessed it. Not that I would have guessed anything, but I love Lady Gaga. I mean, she's just very, very talented. Can you rhyme amplitude in a sentence?

Oh man. I think we tried this once. There's no— what's the— yeah, I don't got it. I'm sorry. I'm not a poet. You can ask— Attitude. There we go. Oh, wow. Amplitude brings you attitude. Boom!

Amplitude brings you attitude. I like it. You can ask one person one question. What person? What question? Hmm, hard, hard, hard, hard. I mean, these are actually the hardest questions I ask.

Yeah, you want to— I want to ask myself 50 years in the future, what do I work on now? That would be the question.

This is an amazing— oh my gosh, no one's done that. No one's answered that question with a, I want to ask myself. I've asked that question 100 times now, something like 100 times. No one has said, "I want to ask myself." I love—

well, in the future, 50 years, sure, it's future you. I could actually ask someone else. I, you know, I could ask you 50 years in the future. No, I love someone 50 years in the future. What should I be working on now? If I could know that, like, that'd be perfect.

That's, that's a great way. Okay, okay, this one's— it gets more into like people actually. So there are 2 people that you would want to meet in history. To have dinner with.

Sorry, this is a dinner. Dinner. Okay. I only get dinner with them. All right. Oh, oof. That's hard. The one that's been my idol is like Bill Gates. Like he's just fucking amazing. Amazing in so many respects. Have you met him yet? No, I haven't. You know, I hopefully, hopefully I get the chance to, um, at some point, uh, he's kind of, you know, he's kind of chilling out working on his nonprofit stuff these days.

But, you know, hopefully gonna, you know, I don't know, he sort of feels like a no-chill guy. He just keeps going.

So yeah, yeah, it's funny. It's, yeah, he's, he's just amazing. Like, the fact that he reinvented himself after Microsoft is amazing. So yeah, that's, that, that would be, that would be Bill Gates. Bill Gates. Yeah, he's, he's kind of like, it's like, okay, if I could be like, you know, just, just learning from how he is. So that, yeah, that would be one amazing one. Other one that would be really interesting, you know, if you could meet, let's see, who would I want to go back in time and meet? I don't know, let's keep going.

Okay, this is the last question, so we are almost done. What is your definition of success?

All right, I'm going to, I'll take a while for this one. This one's really, really hard. This one's really, really hard. The biggest thing I found when looking at— before I did startups, I was like, hey, what do I want to do with my life? You know, is it startups or something else? And the biggest thing I found was that the people who were most successful were doing what they were doing for like a purpose that was really, really big, that was beyond themselves. Whereas the people who were less successful in their lives were doing it for kind of like internal reasons. So Let me give you an example. Some of my friends from college would go to med school because they're like, "Oh, yeah, my parents want me to go," or, "That's a prestigious job," or, "I think that will be good," or they'd go to the big tech job because, "Oh, lots of people are going there and I hear that's a cool place to work," or, "My parents want me to get a good job," or, "I think I can make lots of money," or what have you. The people who are most successful in their fields, whether it's business or art or research or whatever, are doing it for a purpose that's much bigger than themselves. And so that was something that always stuck with me. It's like, hey, figure out how to make yourself part of some movement that's much bigger. Figure out— the reason I'm in technology is I'm a big believer in technology and the ability of it to change the world. And so it's like, okay, that's what I'm I'm here to do? How do I make other people's lives better with this thing? And that's like a never-ending problem and something I can feel great about doing. Whereas if I were just doing this to get rich or to have a lot of success or to— because it's so cool. There's so many people doing startups because it's the cool thing. What's going to happen is at some point it's not going to be the cool thing and it's like, you know, I'm going to give up. And then it's like, okay, well, why was I doing that? Adam, like, I just— for the folks in this group, like, you guys are working on, like, the future, a totally future new way of interacting with technology, which is just— it's so awesome. And like, if you kind of look back in time to when things like this have happened, like that, the kind of— I think it was like the Berkeley Computer Club that, like, Apple got started at, or what, Xerox Labs sort of thing, or Xerox. Yeah, there's a bunch of them where it's like It just looks like some group doing some random thing that most other people don't understand, that doesn't feel like a big deal, but they're working on— you're working on the future. That, to me, is just— that's the fun of stuff. You kind of don't get that opportunity to do that anywhere else in your life. There's a lot of paths to— if you want to— and to be clear, startups is not the only thing. You can have lots of reasons in terms of what it means to live a good life. Want to have a great family, or you can want to help improve other people's lives or whatever. And there's lots of ways to do those things. One of my definitions for success or one of the ways that I kind of define success for myself is like, "Hey, how can I make the world a better place?" And I see what we're doing as a great way to do it.

That was fantastic. Thank you so much for coming to the Boost VC speaker podcast.

Yeah, absolutely. Happy, always happy.

This was amazing, and it was also just great to reconnect. After all this, I would love to go grab some food with you in a public setting.

Yeah, let's do it. Let's— once we got to wait for the ash clouds to come out of the sky first, but let's do it. Yeah, after that, I'd love to.

That'd be great. Okay, let's do it. Okay. Hey, thank you so much. You were awesome. This was amazing. This was just the best.

Thank you so much. Awesome. Look, I just want to say thank you again, Adam, and to everyone in Boost. The fact that you're doing it puts you ahead of most, the vast majority of other people. You guys are working on some really cool stuff. My biggest thing is just keep at it for a long period of time and you'll figure something out. Yes! I love that.

That's the best sign-off. Okay. Later, Spencer. Answers. Talk to you later. Thank you so much for tuning in during your busy day to learn about Sci-Fi Technologies. For more info on what we do, check out our website at www.boost.vc or give us a follow on Twitter and Facebook @BoostVC. A big thank you to Maddie Callender, Coy Lee, Ben Lavelle for their support in creating and producing this podcast. A musical thank you to Melodrive and their AI composer for our amazing intro and outro songs. If you need music for your digital content, check them out at melodrive.com. Lastly, thanks to Tim Hollowell with The Podcast Group in Washington, who did an incredible job mixing this audio. Boost VC is all about helping amazing Sci-Fi Tech succeed. If you have an idea you think we should hear, get in touch with us at boost.vc/contact and make sure to sign up to get notified when applications open for the next accelerator tribe. Also, we love to hear from our listeners, so rate us and drop us a comment on whatever streaming service you use. We would love to hear feedback. That's it for this week, and unfortunately we don't have enough time time for Mark Zuckerberg, but be sure to tune in next week when he's available. This is Adam Draper signing off. Pew pew pew!