Sep 23, 2026 · 1 hr 15 min
EdwardKim
Co-founder & CTO of Gusto
$9.5B Gusto Founder Went Back to Being an Engineer to Build an AI CoFounder - Edward Kim
In this episode
Today I walk with Edward Kim, co-founder and CTO of Gusto. Edward built Gusto with two Stanford classmates into a $9.5B payroll platform running 300,000 small businesses, made over $1M selling Android apps on the side, and after a decade managing engineers, he's writing code again to ship an AI co-founder for the back office his mom used to run when he was a kid. He gets into why his doctor dad handed him a Paul Graham essay in the car, and the unfairness technical co-founders feel while business co-founders raise the money.
- Making $700K a year selling Android apps after his first startup shut down
- Why his doctor dad handing him a Paul Graham essay changed his career
- His mom running the entire back office of his dad's medical practice while raising three kids
- The unfairness technical co-founders feel while business co-founders get wined and dined by investors
- Going back to code after 10 years managing engineers to ship an AI co-founder for small businesses
Chapters
- Trailer
- Edward Kim, Co-Founder and CTO, Gusto
- The elaborate escape rooms he builds for his wife Yuna
- The San Francisco half marathon on a bet that reconnected him with Josh
- Making $700,000 a year selling Android apps
- Screenshot It, the $7 app for a feature Android didn't have
- His mom running the entire back office of his dad's medical practice
- The Paul Graham essay his doctor dad handed him in the car
- Getting into Y Combinator with Gary as a partner
- The unfairness technical co-founders feel while business co-founders raise money
- After 15 years of co-founding, why the workload evens out
- Building Gusto Co-Founder for the small business back office
- His life philosophy in one sentence
- Outro
About the guest
Full transcript
LubaEddie, thank you so much for coming on the show.
EddieThanks for having me.
LubaI was talking to your lovely co-founder in life, your wife, Yuna. And she was telling me that you built very elaborate escape rooms for her on her birthdays.
EddieI did, yes. She loves escape rooms. And so there's been a couple times where I will set up my own escape room. Buy a bunch of locks from Amazon, buy little prizes that she gets along the way. And when she wakes up, like, she has this escape room to solve in the morning.
LubaThat's incredible.
EddieShe loves it. It's, like, her most favorite thing to do.
LubaHow many years have you been doing this as a surprise?
EddieI've only done it twice, actually. One was watermelon themed and the other one was pineapple. Yeah, one was watermelon themed and one was pineapple themed. And we have our little dog, Elmo, and she gets to be a part of the escape room as well. Like, hide a little key in her collar.
LubaThat's amazing. So how long does it take for you to create an escape room?
EddieIt's actually not that hard to create, because you kind of, like, just start from, like, the final puzzle.
LubaOkay.
EddieAnd then you work backwards from there.
LubaAnd do you create the final puzzle, or do you get inspiration somewhere for, like, this is the type of escape room that I want to make?
EddieThe first time I did it, yeah, this was pre-ChatGPT. And so, like, you had to, like, kind of make it up by yourself. It was a lot harder. Second time, ChatGPT, like, can kind of come up with all the little puzzles for you. So it's a lot faster to do. But yeah, it's pretty simple. Like, actually, just because you work backwards from, like, the prize. And if you do it that way, it's easy to set up. But then it's one of those things, it's, like, easy to set up but, like, harder to solve.
LubaRight.
EddieYeah. Yeah. So going forward, it's a lot harder to do. But, like, kind of going backwards, it's a lot easier.
LubaDo you love puzzles and, like, strategies? Is this a project that you have a lot of fun making?
EddieWe love, like, board games, and, yeah, you know, Yuna loves puzzles. She will get very, very into it. She's also very, very competitive. So yeah, it's something we enjoy doing.
LubaThat's amazing. So competitive. One thing that stood out to me is that you decided to run a marathon back, like, long, long time ago, or whatever, 15 years ago. And that's where you reconnected with now one of your co-founders, Josh.
EddieYeah.
LubaAnd that marathon was on a bet. Like, you weren't really prepared.
EddieThat's right. Yeah.
LubaCan you bring me back to that time? Tell me more about this marathon and how you were connected with now your co-founder.
EddieYeah. So, Gusto started with three co-founders: myself, Josh and Tomer. But Josh and I, we actually met in college. We both went to Stanford. We were the same year, same major. We studied electrical engineering, and so we had a lot of, like, classes and labs and things like that together. You know, like a lot of your college friends, after college you stay in touch, but then you don't necessarily, like, see them all the time, because you're not in classes together. You're not in the same dorm. And so that was, like, kind of, like, what happened with Josh and I. We stayed in touch on Facebook and social media, but we kind of, like...
LubaYours was that you were kind of loosely in touch, but not really in touch?
EddieThis was probably, like, three years after college.
LubaAnd you were doing your first startup at that point.
EddieI was in my first startup. And then my first startup, I shut down, and then a year and a half after that, I started writing a bunch of Android apps on my own and just sort of, like, selling them on the Android marketplace.
LubaOh, that's cool. Did you make a lot of money with that?
EddieI made more money doing that than doing my first startup.
LubaThat's telling you something.
EddieYeah, yeah. So by the end of my first startup, like, I had actually, like, you know, spent a lot of my savings on it, and I needed a way to make money. And I was unemployed. And at that time, Android was starting to become, like, a bigger platform. It was all about iPhone at the time. And Android was just sort of this, like, up-and-coming operating system. And so I started, like, building a bunch of Android apps, because I always loved Android phones.
LubaJust love an Android phone.
EddieSo I've always had... and I've never owned an iPhone. I am the green bubble, die-hard person.
LubaI respect it.
EddieAnd actually turned out to be one of the, like, first, I guess, app developers on the Android platform that was able to actually make a pretty good living...
LubaWow.
Eddie...doing it.
LubaWait, so give me some numbers. Like, how much money were you making at its peak?
EddieI was probably making, like, 700,000 a year.
LubaWow.
EddieJust selling Android apps.
LubaThat's crazy.
EddieYeah, and it was also a lot of fun. And so I had a lot of free time.
LubaOkay.
EddieAnd I was, like, kind of, like, finally, you know, more financially free for the first time in my life. And then I had all this time for these kind of, like, random hobbies. And one day I was hanging out with friends and they were like... we were just talking about running the San Francisco Half Marathon, which just happened.
LubaWhat, just happened?
EddieYeah, yeah.
LubaDid you run it?
EddieNo, I only did that one time.
LubaOkay.
EddieAnd I'll tell you why. So I was like, ah, I could run this San Francisco Half Marathon. That's easy. Even though I didn't train, I was not really a runner, you know, and I was not. But I was just, like, very young and dumb and foolish.
LubaYes.
EddieAnd so I did it on a whim, and...
LubaAnd you actually were able to complete it.
EddieI was able to complete it. But, like, around mile 9 or 10, my knees, because I had not trained at all, really started to give out. And, like, I probably, like, more or less, like, fast-walked and limped the last three miles, and I couldn't, like, walk for, like, the next three days. So I highly do not recommend trying to run a half marathon without any training at all. I'm proud that I finished it, but, like, it was not a good finish, and, like, I probably wouldn't do it again. I haven't done it again since then.
But, like, what happened was, at the start of the marathon, I ran into Josh, and he was a friend that, you know, I had known well in college, but again, didn't really spend that much time hanging out with after college. So it was one of those moments where we were like, hey, like, good to see you again. Like, it's been a while. Let's catch up after the marathon. And a few days after, after I recovered, we got coffee at the Creamery on Fourth and King in San Francisco.
LubaAnd is it still there?
EddieIt's not there, but there's a lot of, like, VC, like, startup, like, stories that have their origin story there, actually. And some other ones, it just became, like, the spot where a lot of, like, people would get funding and VCs.
LubaKind of like Blue Bottle in South Park now, kind of.
EddieYeah. Yeah. Or, like, I think Coupa. Coupa in Palo Alto at Stanford. And so we just met up there and we caught up and started hanging out again. And, you know, we would spend some time together, we'd hang out. Josh had spent a lot of time at my place, because his girlfriend was actually living in the city, even though he was living in Palo Alto.
And then we just sort of, like, reconnected. We were kind of in the same place in life, I think, where we had both started our first companies. We had finished our first companies, and we were sort of, like, doing our own independent thing.
LubaWhat was his thing?
EddieHe was... so his company got acquired, and he was actually working for the company that acquired his company. And I was doing my kind of Android app. But we were both kind of, like, in this place in life where we were making money. We were fine financially, but then we wanted to do something much more meaningful in our lives. And so that's kind of how we reconnected. We started talking about that a lot. And one thing led to another, and eventually we decided to start a company together.
LubaThat's amazing. ZenPayroll at the time, and now it's called Gusto. And what was the definition of meaningful back then? So both you and him were like, yeah, you know, whatever we're doing right now is going well, but we want something bigger, better, or... what was it?
EddieYeah, I think we wanted to solve a bigger problem. We wanted to do something more than just make money. We were like... I was having a lot of fun doing random things, like running half marathons. But I also started asking myself, like, is this what I want to do for the rest of my life? And my answer was no. I wanted to do something more. I think I want to make a bigger impact, I think. And so it was, like, kind of more of that mindset of, like, there's something more to life than just, you know, writing Android apps and selling them on the App Store and making money from it.
LubaAnd what were some of the Android apps that you were making?
EddieSo I made a lot of, like, utility-type applications. I'm terrible with directions, and I'm always losing my car in parking lots. So my first app that actually turned out to be really successful was an app called Car Locator.
LubaOh, cool.
EddieYou literally just saved your location.
LubaThat's amazing.
EddieAnd it points you, like, how to get back to your car. But probably the most successful one I wrote was this app called Screenshot It, which lets you take a screenshot on your Android. And this actually... Android was so early on that the phone literally did not have the functionality to take screenshots.
LubaWow.
EddieAnd so a lot of people, obviously coming from iPhone, wanted to take screenshots. They had no way of doing it. I found a way to sort of, like, build this app that takes a screenshot. And people were willing to pay, you know, like, actually $7.
LubaWow. For one screenshot, or for the subscription?
EddieProbably for... yeah. Just for the ability to screenshot on their phone. And that was probably the most successful app.
LubaSo how come you didn't think that these, you know, apps that clearly solved a problem were meaningful? Like, why was... because you were solving something that people needed, like Car Locator.
EddieYeah.
LubaLike, yeah. What was it about it?
EddieYeah, I think that's a good question. I think I knew that eventually Android would fill in these gaps, which turned out to be true, right? You could use Google Maps to save your location and navigate back to your car. You can now take screenshots on your Android.
LubaSo you were like, this is not going to be long-lasting.
EddieNot gonna be long-lasting. It is solving a small problem. But is it, like, kind of a, you know, a meaningful problem? It's just not that deep of a problem. It's, like, a small, like, minor pain in your life.
I grew up in a small business, and, you know, my mom and dad, they sort of worked together for 30 years running this small business. And I knew, kind of growing up in the small business, like, how much of a bigger problem it was to figure out how to, like, run a small business. How to take care of all the compliance issues, your taxes, benefits, HR laws and things like that. And that was just something that I grew up watching my mom struggle with every single day. She worked so hard on all these things that were not necessarily, like, related to what the business was doing, but necessary things to sort of stay compliant and have a legal business.
And so, you know, in the back of my mind, like, I knew this was, like, kind of a much bigger problem, and ultimately, you know, warmed up to the idea of actually solving this problem for the world, and just feeling that's much more meaningful and something that I could be much more proud of than writing Android applications.
LubaSo would you say that your experience with your family was the seed to ZenPayroll becoming a reality?
EddieI think it was a big part of it. I cannot say that when I was a young kid, like, growing up in the back office of the small business, that I knew growing up that I wanted to... this is gonna be my future, to, like, solve payroll for small businesses. But, like a lot of things, I think these sort of, like, ideas get seeded in your head and they kind of, like, lay dormant until, like, an opportunity comes along and you kind of think about it more. And then it's sort of like... the neurons that are storing this thing in your brain are lying dormant for a while, and they turn on when you're in the right situation, with the right person, in the right stage of life.
LubaRight.
EddieAnd that's kind of one thing that I learned, is that, like, you know, for startups, there's obviously so many things that have to go right. You've got to get the right people. You have to have the right problem. You have to be in the right market. But there's honestly, like, a lot of just, like, luck in it as well. Meeting the right person at the right time. If I had not run that half marathon on sort of a bet with my friends, I would never have run into Josh.
LubaYeah.
EddieI might not have founded this company.
LubaRight. And you ran into him very randomly at the marathon.
EddieYeah. And I think that was like, if that had not happened, like, this company might not have existed.
LubaWhat are some other examples of how luck significantly played a role in your life?
EddieSo, I mean, I could talk a little bit about how we met Tomer too, which I think was a lot of, like, serendipity as well. Tomer, for context, is our third co-founder. And he grew up in Israel, studied at the Technion, and came to San Francisco and got into Stanford's PhD program. And he enrolled in this sort of alumni slash newcomer networking program, where Stanford would connect Stanford alumni like Josh with new students at Stanford who are coming in to get their PhD. And so they kind of get to know each other.
So, randomly, Josh and Tomer got connected. And Josh kind of became a little bit of, like, a, you know, here's Stanford, and here's, like, you know, here's how to get around and all that stuff. Like kind of a... I want to say a mentor, but, like, a guide.
LubaA guide. Yeah.
EddieAnd they really hit it off. And eventually they decided to live together in this house in Palo Alto together. And that's how they met.
LubaRight.
EddieAnd I met Tomer through Josh, because Josh was like, hey, you got to meet Tomer. And we just hit it off. We have a lot of the same values. We grew up very similarly. And so I'd say all of those are kind of, like, just luck.
LubaYeah, yeah, yeah.
EddieLucky events that happen.
LubaAnd how do you think someone can manufacture luck in their life?
EddieI don't think you can manufacture luck, but I think you have to just be really prepared for when those moments arrive. And, yeah, I think sometimes opportunity knocks and you have to open the door, right? And sometimes you don't open the door if you're not ready. But I kind of always feel like if you have an opportunity, you should at least explore it and open it up.
LubaWhen I was talking to you, and as you said, you also consider yourself to be a lucky person. Like, when you guys would be looking for parking. Oh, you know, parking. And you'd be like, well, I'm lucky, so parking will appear. And it actually does.
EddieYeah, I'm a very positive person. And so that's a great example. Like, when I'm looking for parking in San Francisco, I always feel like... I genuinely feel like I am parking lucky. That, like, a parking spot just opens up at the right time. And it does. And so sometimes I just feel like I can, like, manifest it. I think positive mindset really kind of leads to more good things in your life.
LubaRight.
EddieAnd I can't explain why.
LubaBut do you believe in manifestation?
EddieI don't think I believe in manifestation, but I believe that, like, a positive...
LubaYes.
Eddie...mindset can open your mind to, like, walking through the door a little bit more. And so, yeah, I mean, I guess you can call that a little bit of a manifestation. But I think it's, like, being open to serendipity and...
LubaTo what? Yeah, to your point, opportunity. If you're always negative and you think you're unlucky, or things will not happen for you, that means that you're normally closed to them happening, because you're going to likely say no, or be like, oh, I'm not that type of person, so it's not possible.
EddieYeah, exactly. Yeah. I'm a big believer in positive mindset.
LubaI love that. Tell me a bit more about how you grew up. So your mom and dad were small business owners?
EddieYep. Yep. Yeah. So they both were born in Korea. My dad studied medicine, and he came to America to become a doctor. And so we moved to this little town in Southern California called Upland. And he started his own small private practice. So he's just kind of, like, you know, local doctor seeing patients. So my dad was, like, the front of the business, because he was, you know, the doctor seeing the patients. And my mom was, you know, the entire back office.
So she ran payroll. She scheduled appointments. She greeted them. She was the office manager. She billed the insurance company. She filed the taxes. So she did all the things that you needed to do to keep that business running while my dad saw the patients. That was, like, kind of, like, their division of responsibilities.
And because they both worked, my mom would sort of leave the office around, like, 2:30 when we would get out of school, pick my sister and I up, and then shuttle us back to the office and just hide us in the back room. And we'd just sit there, do our homework. We had a little TV there, so we would watch some cartoons.
LubaWhat were the cartoons?
EddieOh, we loved, like, Tiny Toons. Darkwing Duck. TaleSpin. Batman.
LubaNice.
EddieYeah. We loved all the cartoons. Power Rangers. So we'd just kind of hang out there until they were done working, and then we'd all go home together, and it'd usually be pretty late, you know, like maybe 7 or 8 p.m. Because when the office closes, it's not like the work is done, right? You have a bunch of stuff that you have to do after all the customers leave. And so we'd get home pretty late and then eat dinner. And that was, like, kind of, like, how I grew up until I could drive.
LubaAnd what were you influenced to become?
EddieI wanted to be a lot of things growing up. I'd say there was a period of time where I really wanted to make film.
LubaMhm.
EddieSo I wanted to be, like, a director, producer. And that's kind of, like, going into college...
LubaYeah.
EddieThat's what I wanted to do. I thought I was going to major in film.
LubaFilm. Yeah.
EddieAnd, you know, speaking of serendipity, this is another one of those things, where I grew up in a city, in a school that was... it was okay. It wasn't, like, a great school. It was, you know, Upland High School. I had a great high school experience, but they didn't have, like, computer science or any of those classes. So when I got to Stanford, like, it was my first time hearing of computer science and the first time hearing about electrical engineering. Never even heard of these, like, subjects, right? The only subjects I heard of were, like, math, film, and... well, not film, obviously, but...
LubaWell, the funny thing is, as a major.
EddieYeah, yeah. So I actually applied to Stanford, and I wrote my essay about why I wanted to be a filmmaker. Why I wanted to study film. And I wrote this essay, so I got...
LubaAnd what was it? What did you write, if you remember?
EddieWell, I think when I watch something, like a movie, it really, like, kind of... like, for me and for most people, it really, like, sucks you in, right? You develop a lot of empathy for the characters. You kind of, like, put your guard down in a way, and you just sort of, like, experience what the main character is experiencing. And I think that's such a powerful medium of persuasion, right? You could share a positive message through this medium of film in a way that I think an essay or a speech just can't, right?
Because when you're reading something or you're hearing something, especially if you don't agree with the person who's saying that to you, you kind of immediately think of the counterarguments. You have, like, kind of your guard up as to why I'm right and this person is not. But when you watch, like, a really good movie or a really good documentary, right, you kind of, like... that sort of, for some reason, I noticed, it goes away, and you allow yourself to, like, develop this deep sense of empathy and understanding. And by the end of the film, you can come out, like, very convinced of something that you never really thought you could agree with, right?
So I just thought that it could be such a powerful medium of persuasion. And of course, like, it can be used for good and bad, right? You could have, like, propaganda that can be used for convincing people of untruths as well. But this is a really powerful communication medium. And so that was, like, kind of, like... that was the reason why I wanted to be a film director, and what I wrote my essay on.
Ironically, I got to Stanford, so they accepted me, and I don't really know why they accepted me, because, like, when I got there, I was like, great, I'm gonna study film. Well, they don't have a film major.
LubaOr what? Well, you didn't know that?
EddieI didn't know that.
LubaI was like, Stanford seems like an interesting choice for a film school.
EddieYeah, yeah, yeah. I mean, I love Stanford. That's why I knew I wanted to go to Stanford.
LubaOkay.
EddieThat was, like, my dream school. And then I knew I want to study film, but, like, it turns out, when I got there, that, like, I can't have two at the same time.
LubaIt's very funny.
EddieSo I actually, believe it or not, like, settled on... they had a communications major, and then becoming, like, a communications major. But my roommate, who was, like, randomly assigned, was studying computer science, and he was taking the intro to computer science class. And, you know, he just kind of, like, said, hey, I'm taking this class, like, why don't you take it with me? We can, like, do our, like, homework together and go to class together. So I was like, all right, whatever. Like, I'll check this thing out. I never heard of it.
And so it was my first computer science class ever. And I loved it so much. Like, it was the first time where I really looked forward to actually doing the homework. And I could stay up all night, like, you know, right? Do the problem sets, write the programs that they have us do, right? And actually, like, just get totally sucked in. And I kind of, like, knew that, like, just the way I was feeling about, like, the school subject was, like, completely different than how I felt about most school subjects. And I realized that, like, this is kind of, like, the direction that I wanted to go. And so that was also, like, a very serendipitous thing. Where, had I not met this roommate that happened to be studying computer science, I might not have explored that route.
LubaBut again, that's also a testament to your point about being open-minded, to saying yes to opportunities and doors that open. It also reminds me of when I went to school. I went to school in Canada. I studied chemical engineering, and then through also osmosis and hanging out with people who studied computer science, I was like, oh, let me take a Codecademy HTML, CSS class. And I was open enough to do that. And I was like, oh wow, this is very different from MATLAB that I'm studying, and... I actually like it. And then that led me to teach myself how to code and transition into tech.
EddieRight? Yeah, yeah. It's like you can't really predict the path you take in life, but you can be open to the different paths. And I think that kind of, like, oftentimes, more often than not, like, kind of leads to good places.
Luba100%. So, to jump back, you wanted to become a lot of different things, but then you took this computer science class and were in love with that and decided to be in tech.
EddieYes.
LubaBut then the other thing that stood out to me is that your dad gave you a list of essays by Paul Graham when you were growing up. How did that happen? Like, that seems so random.
EddieYeah, and it was one day, I remember, I think I was actually a senior in high school, and we were driving, getting in the car and driving somewhere. I don't remember where, but he had printed out this essay and he handed it to me.
LubaDo you remember which essay it was?
EddieIt was, I think it was "How to Start a Startup." It was, like, one of his classics.
LubaAha.
EddieAnd I read that, and I kind of was like, I want to do this.
LubaDid your dad read the essay, too?
EddieI'm sure he did. Yeah.
LubaAnd so... because I'm just kind of surprised that, like, a Korean immigrant who probably has a very specific idea for what he wanted his kids to do...
EddieYeah.
Luba...would be like, oh, you know, this is how you start a company, and take this big risk, and not become a doctor or a lawyer or an engineer.
EddieWell, he actually really... because he was a doctor, and he really wanted me to be a doctor. He's been, like, all my whole high school, trying to convince me to be a doctor. But, like, it just didn't resonate with me. Like, for me, medicine was a lot of, like, memorization of different, you know, body parts and cellular structures and things like that. And I was just never... like, going back to Car Locator. Like, I just have a terrible memory, like, always forgetting where my car is. And so I just knew that wasn't it for me. Eventually, I think he gave up.
But, you know, I think a lot of immigrants, they are entrepreneurial because they come here, and oftentimes the best thing that they know to do to survive is to start their own business, right? So in some ways, even though my dad was a doctor, he was, I think, entrepreneurial in the sense that he started his own private practice in, like, a random city.
LubaMhm.
EddieAnd, you know, made a living for himself and his family by doing that. So I think there was a part of him that, like, was entrepreneurial and wanted me to be entrepreneurial as well. I don't think he necessarily knew it would be technology or software. But I think he wanted me to do something that was, you know, maybe a little bit different than what most people do.
LubaAnd so you were PG-pilled since a young age?
EddieYeah. And I didn't know that was Paul Graham, or who that was, at the time. It was just this essay that someone wrote that sort of resonated with me. But it was, you know, again, one of those things that I sort of, like, tucked away, and it probably laid dormant in my mind somewhere. And I went to Stanford and studied engineering there, and eventually graduated, and I took my first job, which was, you know, at a big company. It was Volkswagen. They had a research lab that I had joined.
And then about two and a half years into it, I think that essay sort of, like, started to come back to the top of my mind again, and I wanted to sort of, like, start my own company. I was, like, reading TechCrunch and, you know, all these founders that, like, were just, yeah, scrappy, starting companies. And I started to hear a little bit more about this thing called Y Combinator that nobody really knew about. I was reading Hacker News, and eventually, like, I decided I wanted to start my first company. I wanted to do it by joining Y Combinator.
LubaAnd who was in your first Y Combinator batch? Are you still friends with them?
EddieThat was in 2008. So that was a very long time ago. Probably the one that I stay in touch with the most is this company called Posterous, which was Garry Tan's...
LubaOh, yeah.
Eddie...startup. And so Garry Tan and I, actually, funny story, like, we were also at Stanford together. And we were in the same dorm. And so when I was a freshman, he was a junior. So that's how I got to know Garry Tan. And then we both found out, like, on the first day of Y Combinator, that we had both gotten in, and we were batchmates, basically.
LubaWow.
EddieSo he was starting his company. I was starting my company. And we had to move to Boston at the time. And that was, you know, it was, like, kind of this crazy experience. Y Combinator was very, very small. There were...
LubaAre you still in touch with Garry? Are you guys still friends?
EddieYeah. Yeah, yeah, yeah, we're still good friends.
LubaHow has he influenced you?
EddieHe's influenced me in so many ways. Like, in many ways. You know, I've kind of, like, followed a lot of, like, the advice and path that he's set. He, you know, I think, like, in all the bad times, was very encouraging of, like, kind of going through all the ups and downs of a startup. And then when I started my second company, Gusto, also started through Y Combinator. At that time, Garry was a partner at Y Combinator. And so oftentimes I would, you know, both officially through the Y Combinator, like, programming, but also unofficially as a friend, would just kind of oftentimes, like, talk to Garry if I had a problem that I was struggling with or needed some advice. Garry would always be...
LubaAre there any specific stories that come to mind where he was particularly helpful?
EddieStartups are, like, so much ups and downs. And especially in the beginning, I think, you don't see a lot of traction in the beginning. And then one thing that I dealt with a lot, which I think a lot of, like, technical co-founders deal with, is sort of this feeling of unfairness when you're starting out. Where the situation oftentimes in a startup is, you have a person who's, like, kind of more on the business side, and you have a person who's more on the technical side. I was more on the technical side.
And the person on the business side, at least in that stage of company, like, there isn't a lot of business, right? Not a lot of... And so your job really is to kind of go raise a lot of money, talk to investors. And if you're kind of, like, a more in-demand startup, which fortunately we were at that time, you're getting, like, sort of wined and dined by investors. But meanwhile, like, the technical side has got to code. We gotta, like, build the software, right? And so my life was working probably, like, 16 to 18 hours a day.
LubaWow.
EddieJust coding in front of a computer nonstop. Sleeping, eating real quick, and coding, right? And meanwhile, like, you have the business founder who, you know, is going to, like, a nice steak dinner, or, like, going to see the Warriors, because, like, the investor wants to invest money, right? And that just kind of, like, I think, led to, like, a little bit of a feeling of unfairness at the time. And I think there's a lot of ego involved.
And so I actually talk about this a lot, because, like, I know, like, what I went through as a technical co-founder is, like, not unique. And I talked to many, like, CTOs, like, founding CTOs, that kind of, like, went through the same experience. And so, just, you know, going back to, you know, how we got on this topic: like, that was something... Garry is very technical, right? It's something I talked to Garry a lot about, and I think he gave a lot of great advice on how to manage that. And it helped a lot. And I talk to a lot of, you know, young technical founders about the same thing, to try to pass on what I learned during that period.
LubaAnd so for someone listening, if they are in that position, what should you do if your ego feels a little hurt?
EddieYeah.
LubaThe lack of wining and dining.
EddieYeah. I mean, I think a lot of it really comes down to ego. I think you have to, like, check your ego and realize that, like, you are in this company building together, and you have to have a lot of trust in that, and you have to trust that, like, everybody is doing what they can. If you have a good co-founding team, everybody is doing what they can to make this company successful. And Josh was doing everything that he could, and he was doing the right things, right? It just felt unfair, but, like, it actually wasn't.
And the other thing that I learned, which I talk about, is that, like, you can't, like, take one point in time and see, like, you know, your co-founding team, how much they're contributing, or how much they're, like, you know, able to contribute, and just judge based on that. You have to look at it over a longer time period. Because when you're doing something for a very long period of time, and we've been doing this for 15 years now, there will be periods where you have things in your personal life which make things really difficult for you to contribute fully to work, right? And there'll be times where, like, you can go all in and, like, go super hard. And those ups and downs will not line up with every single founder at every single point in time, obviously, right?
There's gonna be some periods where, you know, you're carrying a little bit more load, and other periods where others are helping you out, right? And so I think if you have the wisdom to look at it over a longer period of time, in my mind, everything sort of evens out, right? If you have a lot of trust in your team. So that's the other thing, is, like, you have to build a lot of trust with your co-founding team, that, like, you will be there for each other when the time comes. And so everything really comes down to, like, trust and ego.
LubaSo on that point, you were the CEO of the first company, and then in the second company, Gusto, you are the CTO, the technical leader. Josh is the CEO. How did you guys make that decision?
EddieYeah, and that was, like, one of the really early, like, very vivid and clear moments that I had when we were just, you know, starting out. We had kind of gotten into Y Combinator. We just sort of sat down in the office that we were working at. And I remember, like, we were, like, just kind of three chairs, myself, Josh and Tomer, like, sort of facing each other.
LubaWow.
EddieYeah. And then we just had this discussion of, like, what is our role going to be in this company that we're building together? And it's a little bit awkward, right? Because everybody, honestly, they want to be the CEO, not gonna lie. But we had this, like, very sort of explicit, I guess, slightly uncomfortable conversation about our skills, our desires, and ultimately left that meeting with a very clear understanding of who's going to be what role and title in this company. Josh is going to be the CEO. Tomer is going to be the chief product officer, and I'm going to be the CTO.
LubaRight.
EddieAnd so we kind of, like, even though it was a little uncomfortable, I think we kind of all put our egos aside, and we said, this is the thing that's the best for the company. And we agreed to this. And I think that's another, like, advice I give to, like, startups that are just starting, is oftentimes I see them defer that conversation because it is uncomfortable, right? And so founders will sometimes leave that a little ambiguous. But I think it's really important to have that conversation early on, so that there's no misunderstanding down the road. And I see a lot of companies, like, they fail not because they didn't find product-market fit, or they couldn't build the right thing, or, you know, the market wasn't big enough. They fail because, like, they sort of, like, self-implode, where they get into, like, a founder fight and the company just ends, right? And that's, like, in my mind, you know, I'd say in 70% of the cases, completely controllable.
LubaYeah, 100%. I think most people are, to your point, scared to have the conversation.
EddieYeah, it's very uncomfortable.
LubaBut in a startup's history, there's going to be so many times you have to have an uncomfortable conversation. Otherwise it's not going to go anywhere.
EddieOh yeah.
LubaWere there some other moments, over the course of history, where you really needed to sit down and have that uncomfortable conversation?
EddieYeah. So if I fast-forward a little bit, yeah. We launched our product. We were getting some customers, and we raised some money. And so now it came time for us to go hire a few engineers. And, you know, I mean, most of what you need at that phase, and still in any phase, is engineering talent, right? And so as the engineering team started to grow, I started to have to spend more time sort of, like, technical leading, managing the team. The engineers that we hired would report to me.
And so I kind of, like, found myself, like, struggling with both my desire to, like, want to code, which is what I love to do most, but then also, like, the need to sort of pay attention to more of the management-type things that the company needed, right? So one-on-ones, or, you know, after a year or two, employees start wondering about what their title is, or, like, what can they expect in terms of, like, salary increases. All the really important things, right?
But I kind of, like, found myself just wanting to code all the time. And I would, like, you know, oftentimes reschedule one-on-ones and then reschedule it again. And then when I finally had to do it, like, I would sort of, like, not be that prepared. And this went on for a little while.
LubaAnd how many years into the company was this?
EddieThis was, like, maybe a year and a half into the company. This started to sort of really break and become an issue, I think, when we were around, like, ten engineers.
LubaMhm.
EddieAnd Josh kind of had noticed this and had this conversation, sit-down conversation, with me, saying, hey, like, the company needs you to do this, but you're spending a lot of time doing that. I need you to, like, sort of decide what you want to do, because, like, you can't do both. And that was a really difficult conversation, because, like, I kind of rejected that premise at the time. And it was, like, kind of, you know, again, a lot of ego comes into play. Oh, you don't really understand the bugs that we have. And, like, the most important thing is to write code.
But eventually, like, kind of, I realized that Josh was right, and decided that I would spend a lot of time learning how to be a good leader and people manager. And so I just sort of forced myself to stop coding. And I got a lot of mentors. Got a lot of advice, started reading a lot of books, and just sort of learned how to become a manager. And like most things, when you start to do something more and more, you get better and better at it. And when you get better at something, you tend to like it more. And so it becomes, like, this sort of virtuous cycle, right? And eventually, like, I stopped coding, like, for many, many years, and just kind of focused on being the leader, the technical leader for the company, which I loved.
LubaSo a lot of the things that you're saying come back to setting your ego aside and some humility. It's much easier said than done.
EddieYeah.
LubaWhat are some ways someone who's listening can practically figure out how to put their ego aside? What do you need to do?
EddieI think one thing I learned is how to manage your triggers. So everybody, when they hear something that triggers their ego, a literal, like, physical manifestation happens in your body. And it's a little bit different for everybody. Some people, they'll sort of have shortness of breath. Some people get really hot. Some people get really cold. And when that happens, there's a reaction. I think I get really, like... like, I don't breathe.
LubaMhm.
EddieAnd so then when that happens, basically, what it means is your brain is in a state where, like, you're kind of in this fight-or-flight mode, and the parts of your brain that are, like, processing what to do, like, they shut down, and you just kind of, like... your decision is to go to the fight or flight, right? And so when you're in that mode, like, you're not in a good state. Like, this is not the time to, like, make important decisions.
LubaHow did you learn that it was a physical manifestation?
EddieSo I was fortunate, because we had great angel investors when we started the company. And when I decided, okay, I'm going to, like, invest myself in becoming a leader for the company, I'm going to go email all of these investors and ask them if they can be my mentor. And so many of them, I would, you know, meet once in a while. And...
LubaWho were you meeting?
EddieI would meet Aditya, who was the CTO of Dropbox at the time. He's running South Park Commons.
LubaYeah. Okay.
EddieYeah, exactly. And a guy named Steve Herrod, who was the CTO of VMware. And many people were just, like, you know, so kind to spend time to teach me all of these things. And, like, this is one of the things that I learned: that, like, a physical thing happens to your body when your ego gets triggered.
And the kind of key to all of this is, like, knowing what your trigger is. What is that physical manifestation that happens to you? And being able to, hard as it is, like, identify it when it's happening to you. And that's so hard, because, like, when it's actually happening to you, it's, like, really hard to, like, have the sort of ability to know that it's happening, right? It's hard to detect in the moment. But you can train yourself to do it, especially if you know the physical manifestations of those things in your body.
And so that's probably, like, you know, that's a very practical thing, and probably one of the most important things that you can do to manage your ego. And when that happens, just sort of, like, take a step back and, like, let everything sort of reset. Like, just take a minute, go to the bathroom, wash your hands, something, you know, like, and then come back to it and then reset. And I think that's kind of, like, one of my tricks to, like, managing ego.
LubaOne way to also describe it, and it doesn't just go to ego, but anything that triggers you, can be ego, can just be, I don't know, a situation where you naturally get angry or opinionated about something, is being reactive versus proactive, right? So if someone says something, or you're in a triggering situation, you say, pause. Yeah, let me think how I want to react. Versus being pulled by the externalities immediately.
EddieYeah.
LubaYou feel like you have to say something, right?
EddieAnd just... but you don't have to say something. You could say pause. And, like, if that's too awkward to just pause there, like, what I do sometimes is I'll say, I'm going to the bathroom, right?
LubaYeah.
EddieAnd just kind of, like... because I need to sort of, like, not just pause, but I think I need to be a little bit by myself for a little while. And that's okay. You know, like, that's actually, like, really healthy for you to do something like that.
LubaOne way I also love to think about it is: any trigger is an opportunity for you to make a different choice. So it'll be like, pause. What an opportunity for me to figure out how I want to react. So it's almost like a positive reframe that has more growth orientation.
EddieYeah, yeah, 100%.
LubaSo now it's a very exciting point of time for Gusto's history and for you personally, because you guys just launched Co-Founder.
EddieYep.
LubaWhich, to my understanding, made you go back to code.
EddieThat's right. Yeah. It's come full circle.
LubaDo what you love. I don't want to say "the most," because clearly you also now love being a people leader as well. Tell me a bit more about the inception of the product.
EddieI had obviously, you know, started to take a pretty big interest in AI, and I had been hearing more about this thing called OpenClaw. And so I actually bought a Mac mini, I installed it.
LubaOh, yes.
EddieThis was probably in, like, January or February of this year. So not very long ago.
LubaNot very long ago.
EddieYeah. This all happened, like, very, very quickly. And spent, like, a whole weekend with my brother-in-law, actually, you know, Yuna's brother, to set this thing up. Like, that would be a cool project for us to do together. And it's very hard to set up. And when I had finally set this thing up in the way that I liked, like, I didn't really know how to use it. And I thought it was really, really cool. I loved how you could chat with it through Telegram. There are aspects of this I really loved, but then there were aspects of it where I just didn't really understand the hype as much, because I was still using it as, like, kind of a: I say something and it responds back. Not that different from how I would use, like, ChatGPT.
LubaYeah, yeah, yeah.
EddieSo I kind of had that experience. I set it aside. And, like, kind of again, like, now that I'm talking to you, a lot of things are like: something happens, they get kind of, like, put dormant in your brain somewhere, and then something else happens that brings it back.
And so in February, my wife, Yuna, and I went on vacation. We went to Madrid and had a great time. And on the flight back, we actually flew back separately, but on my flight, my connecting flight, I missed.
LubaOh, no.
EddieI was flying from Madrid to London Heathrow, and just barely missed... like, it was, like, literally by, like, five minutes.
LubaWow. Because otherwise it wouldn't have happened.
EddieI know. Because the first flight was delayed. I was running, running, running. They were like, yeah, you can't get in.
LubaYeah, exactly.
EddieAnd so the next flight to San Francisco from London was, like, 5.5 hours later. And so I was, like, pretty mad. I was, like, not happy about this situation. I was gonna get home pretty late. And so I just, like, sort of hung out, like, at the lounge, basically, until my next flight. But I had my computer on me, so I was like, okay, well, I'm stuck here. I'm gonna just take out Claude Code and sort of build this idea that had been kind of, like, percolating in my mind.
LubaAnd what was the idea at that point?
EddieThe idea was, like... so, you know, at that time, everybody was starting to use Claude Code to build software, right? Engineers were using this to build software. And I started asking myself, like, what if we give the power of Claude Code into the hands of Gusto customers, small business owners, and let them build, through a chat interface inside of Gusto, any sort of, like, web app that they want to build, right? Just by prompting.
So, you know, we build at Gusto payroll and benefits and time. But there's a lot of, like... if you talk to small businesses, they have, like, small little needs that they'll oftentimes, like, kind of just do through pen and paper. Or if they're more advanced, they might, like, create a spreadsheet with formulas to build some sort of, like, tracking system, or, you know...
LubaWhat's an example of something?
EddieFor example, is, like, a company wants to track their employees, if they've taken, like, a certain training that they have for their employees, and they want their employees to take it every, like, year or something. And they need some way to track, like, when each employee took their last training, so the manager could remind them, right? And so a lot of times, what they'll do is they'll just put this in a spreadsheet. They'll put dates in the spreadsheet of when they took it, and then they'll check the spreadsheet once in a while. But what if they could just build an app that, like, can just track this for them, right? And employees could log into this thing and, like, kind of say, I took this training. So kind of, like, simple web apps that, like, do basic, like, CRUD-type operations, where it shows you information. You can, like, store information.
LubaI would imagine there would have to be a very big educational component within Gusto. To prompt someone to be like, hey, you can build this little app. This is what it's going to do.
EddieYeah. Well, I mean, the idea was that you wouldn't have to. Like, you could literally just say to someone, like, tell us what you want, and we'll just, in real time, build it for you. Just tell us your dream, right? And that was the kind of idea of, like, can we actually have an experience where a customer could just tell Gusto, through a chat box, I want this app, and then we just kind of, like, build it for you. And that's your app, right?
And so I started to write the code for this at Heathrow.
LubaAt Heathrow.
EddieAnd I had five hours to do it. And because of AI, like, I was actually able to build, like, a functioning, obviously very rudimentary but functioning, prototype to show that this is actually possible, right? And it was, like, almost like a Lovable-type experience, where it builds your own app, except it would sit within Gusto, and it would, like, kind of, like, have the Gusto design system. Meaning that it would kind of, like, not look like just some random app, but it would look like it's, like, literally part of Gusto. Like Gusto had just, like, heard your exact specific small business need, and we built that app just specifically for you, right?
LubaAnd paint a picture: at this point, within Gusto, you are just managing people. You're not actually writing code.
EddieYeah.
LubaDid you start writing code because of AI? Like, what prompted the passion to go back to, like, what you did?
EddieI think AI made this possible again for many technical people leaders. Because what happened with me, I think this probably happened with a lot of, like, technical executives, is, like, you make that transition from IC into people manager. And for me, that was, like, a span of, like, ten years.
LubaYeah.
EddieAnd the technology changes so much, and you're, like, kind of, like... in-house, like, platforms, like, how you do things. Datadog. I'm honestly, like, a little embarrassed to say, like, I never really learned how to use Datadog, because Datadog came, like, in year five of that period. And it's a pretty complicated thing.
LubaYeah, it's kind of complicated to figure it out. And so, Tableau? How do you guys use Tableau?
EddieWe use Tableau. Yeah, yeah, yeah. I mean, yeah, exactly. I'm more of, like, a reader of Tableau dashboards. I don't know how to create a Tableau dashboard, you know. And so I think everything changes so much that, like, you get to a point where you don't have any hope or desire to go back into it, probably, or time.
LubaYeah.
EddieAnd you're honestly, like, at that point, you're so far behind that, like, you're, like, an L1 engineer, basically. Or actually, if you try to code, like, your engineers just get mad at you, because you're just making things worse at that point, right? So that's, like, kind of, like, where things were pre-AI. But with AI, with, like, Claude Code, like, you can learn and get back up to speed on these things so quickly, right? And all the questions that I was embarrassed to ask, on how does this work, how do you use Datadog: just ask Claude Code, and, like, it kind of, like, teaches you, right? And, like, it's almost like the least judgmental technical mentor that you can have, right?
LubaSure.
EddieAnd so that's kind of how I got back into it. Like, I was like, oh, I can actually, like, ramp back into this, and get caught up on what happened over the last ten years, like, pretty quickly. And so that's kind of how I got back into, like, okay, I can actually, like, sort of build this idea myself. I don't need to go, like, bug an engineer to, like, try to prototype this out. I'm just going to go do it myself. And it's also, like, honestly, an opportunity for me to learn, you know, how to, like, build things within our monolith.
LubaYeah.
EddieAgain. So yeah, it was really that, like, kind of missed flight that, again, like... now it's serendipity.
LubaYeah.
EddieI keep coming back to this, I guess. Like, that led to Gusto Co-Founder. Because after I got back to San Francisco, I was pretty excited about this thing, and I started to, like, show this prototype to a few engineers and designers that I had been close with. And they started to take interest in it. And at some point I was like, well, would you be interested in, like, working on this stuff? And it was in March where we sort of got together in Denver, and we just whiteboarded it out.
LubaSo it was literally a month later.
EddieA month later. And while Co-Founder is not exactly that prototype, it is very much, like, in the spirit of what I had built.
LubaSo what is Co-Founder?
EddieSo Co-Founder is basically... any kind of, like, complicated workflow that you have that you're doing to run your business, it could be, you know, running payroll, or approving time off, or, you know, even calculating, like, the commissions that you have to pay your employees, you just tell Gusto Co-Founder exactly how you would do it, and then it's going to just go proactively do it for you on whatever schedule that you want.
And so it's very similar to this idea of building an app, but instead of building, like, an actual, like, graphical user interface app, it's building a workflow for you that it then takes care of for you. Which actually turned out to be much more valuable to small businesses, because the issue is not necessarily, like, they can't build an app. It's kind of, like, the problem behind that is that they need something to, like, simplify and take care of their business processes for them. And so it kind of goes directly to solving that problem.
The other element of it is you can talk with it, not through our web application, but through texting, WhatsApp, email, or Slack. And that part was inspired by OpenClaw.
LubaYeah.
EddieThat's the part that I loved about OpenClaw, where I don't have to, like, log into something and try to figure out how to navigate a web app. I just talk to it and it responds to me. And I could tell it to do things on this recurring schedule, which OpenClaw calls the heartbeat, right? And so we took that same concept of a heartbeat, where you tell it to do something and it'll not just do it for you right then and there, but it'll do it for you proactively on whatever schedule you ask it to do. So a lot of those kind of core primitives were, you know, also inspired by OpenClaw. OpenClaw, which I just spent one weekend with my brother-in-law sort of setting up.
So that's really what Co-Founder is. It's really just sort of, like, helping a small business automate a lot of the, like, back-office business processes that they have, right? And the point of it is to save them a lot of time. And so all those things that my mom had to do running this small business back office, the scheduling, the payroll, the bookkeeping, the taxes, Co-Founder could literally just do it for my mom, right? And so I wish my mom had this when she was starting her business, right? Because I think it would have saved her so much time and so much headache, not having to do it herself.
LubaSo would you say that the target customer is small businesses, or is it also startups?
EddieBoth.
LubaBoth, because it's a small business?
EddieYeah. But, you know, at Gusto, we help a lot of startups, but we mostly help a lot of just, you know...
LubaYeah, SMB.
EddieSmall business. Like a lot of these, like, stores that we just walk past.
LubaI was a happy customer of Gusto for almost four years, for my startup.
EddieYeah. Yeah, yeah. So, you know, any kind of small business: tech startup, coffee shop, church, like, bar, restaurant. Like, those are all the types of customers, and they all have, like, really complex business processes.
I was talking to massage spas, actually, in New York, where you live, about how they run their payroll, right? And so what they do is they use this system called Mindbody, which is, like, kind of crap... which, yeah, it's not great software. But it's used to, like, track, like, you know, therapist A did, you know, five 60-minute massages and, like, seven 90-minute massages, and therapist B did the same amount of massages, but sold, like, three CBD oils and, like, ten hot stone massages. They track all that in Mindbody.
And the way they run payroll is they export all that data from Mindbody. For every, like, 60-minute massage, they say you get paid this amount, 90-minute massage... because they're kind of, like, contractors.
LubaYeah.
EddieFor every CBD oil, you get $15 as a bonus. And every, like, hot stone, you get, like, $20 as a bonus. So they have to, like, calculate the pay, the bonus. They get tips, like, they pool the tips. They have to calculate all of that from a spreadsheet that they create from an export from Mindbody. And then, and only then, after they've calculated all of those things, they go into Gusto. They put in all the, like, hours, payroll, or the benefit... oh, sorry, bonus, commissions, tips. And then they run payroll. That part is, like, pretty simple.
LubaYeah.
EddieBut, like, what you don't see if you're just looking at Gusto is, like, all that work before the work that that massage spa has to do to get to the point where they can, like, go in and run payroll on Gusto. And so Co-Founder can take care of all of that for the small business, right? They can, like, literally go into your Google spreadsheet, like, read the information, calculate it exactly the way that you calculate it, put that information into Gusto, run payroll for you, and then tell you what the total final payroll is.
LubaThat's amazing. So it sounds like you really took on a startup founder hat with Co-Founder, because you were talking to users yourself and doing user research, right? Take me to this time from the prototype to deciding to build it out with the team. Did you take on, like, a more managerial leadership role, or were you still, like, IC-ing and coding?
EddieSo I'd say right now, like, it's probably more IC coding. I just feel like I'm kind of more in the trenches.
LubaYeah.
EddieRight now. Yeah. And, you know, obviously, like, I have a lot of, like, say in the direction, and, like, I spent a lot of time talking to our customers, to try to bring that feedback back to the team, to kind of, like, help them understand what the biggest needs are and what we should be building. But the thing that I love about this team that I'm working with right now is that everybody is just so passionate about what we're building, that we've kind of, like, been able to sort of remove a lot of the traditional software development processes that we typically have when building a project. So we don't have any, like, roadmap. We don't have any Jira boards.
LubaAnd how big is the team?
EddieThe team right now is about eight.
LubaOkay.
EddieWhat I call AI builders. And I say that term specifically because they're not all software engineers. We actually have, like, a designer who is writing a lot of code right now, and has learned, and that's possible because of AI, how to actually, like, write production-grade code.
LubaWow. And not just, like, Figma.
EddieYou know. And so, like, it's been a really, really cool experience to have this, like, very building-oriented team that each brings, like, sort of their own, like, skill set. Like, more on the design side, more on the architecture side, some on the database side. But first and foremost, like, everybody's just writing code and committing it into our codebase.
LubaThat's incredible. Well, what did that stretch between deciding to write the software and launching it look like? How much were you coding?
EddieYeah. So I guess part of my role was to just really set, like, very ambitious targets for us. And so when we kind of had that meeting in Denver in March, I basically told the team that we had this event going on in New York. I wanted to basically have a version of this that we can show to our customers in five weeks.
LubaWow.
EddieAnd so we kind of, like... it was, like, kind of a crazy five-week period, where we went from idea to, like, an actual, like, product that we could show customers. And on that day, we flew to New York and we met ten customers that are using Gusto, and we showed it to them. And we got a lot of really valuable feedback on what resonated with them and what didn't resonate with them. And then after that, like I said, we had another five weeks to actually, like, launch this thing publicly to the world.
LubaWow.
EddieAnd open up a, like, waitlist, so that, like, basically anybody who's a customer who wants to get on, they can raise their hand to get on and we'll let them on.
And so that happened five weeks after that, after we had learned from the initial set of ten customers, like, what was working well and what we had built. And so from start to finish, it was, like, ten weeks. And during that period... we've added a few more builders since then, but during that ten-week period, it was largely, like, 5 to 6 builders that had built this whole thing from start to finish. And so it was really mind-blowing to me, like, what is actually possible right now if you have a group of really AI-native builders working on something that they're really, really excited about.
LubaAnd how did you have enough conviction to make this bet?
EddieI think it just came from my experience of using OpenClaw. Like, kind of having a lot of, like, personal intuition of what I think people would really want, and then sort of building that prototype, and then showing it to customers, and also, like, other, like, people that work at Gusto, and hearing their feedback. And, like, it's just like, when I showed it to people, those kind of builders, when I came back from London, they were really excited about it, right? And so, like, that kind of, like, got me more excited about it. And we were like, what about this? What about that?
Like, and it's just kind of like we sort of, like, built enough excitement and ideas around this that we were like, let's just kind of all get together in Denver, sit in a room for one day, and just whiteboard this all out. And that's kind of just, honestly, how it happened. It happened very organically. It wasn't through any kind of, like, board meeting or, like, annual, like, roadmap planning.
LubaAnd is it because you guys have already built up this scrappy mentality throughout the last over a decade, or...
EddieI think that was a part of it. So this team is pretty tenured, I'd say, on average.
LubaSo you picked out individual people that you're like, this is going to be my pilot team to build Co-Founder?
EddieI didn't, like, pick them out specifically. It was just people that I, yeah, talked to. And these are the ones that sort of expressed interest. In the back of my mind, I hoped they would, like, you know, want to spend time on it. And they did. But I wasn't like, hey, you have to go work on this thing now. It kind of more organically happened. Everything kind of happened very, very organically.
But I think a part of it was that, you know, I have, like, 15 years of experience, like, understanding what customers need and want. And this team was also, like, pretty tenured. I think the average tenure is probably around, like, seven...
LubaOh, wow.
Eddie7 or 8 years. And so a lot of them also knew what users need. And, you know, the team is also pretty senior. So they also had sort of the... they're sort of, like, people in the company where, if they feel like they want to go work on this, you just let them go work on it, because you have a lot of trust that, like, they're going to be focusing on the right problems.
LubaAnd now that you're back in the trenches, and you're not having a roadmap or Jira tickets or, you know, all this unnecessary-sounding planning, how is this changing your view on how the company should run as a whole?
EddieYeah, I think that everybody, even if you're sort of a leader that hasn't, you know, written software in many, many years... I think that a company will benefit a lot from everybody getting a little bit more hands-on now, because, like, you just get a lot more. I've learned so much, like, kind of getting back into the code. Not just about what our customers want and what products they need, but I also have a lot of, like, deeper understanding of what it's like to be an engineer, right? Like, what are the things that we need to improve in our software development process, or our build system?
And so, you know, you hear about them, but, like, you don't really get the nuances of it unless you're actually doing it yourself. So I've come back with a much stronger conviction that, like, yes, it's important to, you know, listen to what people are telling you and, like, get feedback, and talk to your customers. Talk to your team. But there's also this aspect of, like, just actually doing it yourself, that sort of completes the picture in a way that I didn't really appreciate after being sort of in a more managerial position for the last ten years. So I think that's my number one thing. It's like, everybody should be a lot more hands-on than they are.
LubaWhat is it like to be a small business owner in the age of AI?
EddieI think it's changed a lot. It's, in my opinion, the best time to be a small business owner. There's so many things, again, that, like, looking back on the business that my parents started, so many things that my mom had to deal with that were so complicated, and really, really a big ask of any small business owner, that now with AI, I think a lot of that heavy lifting can be taken off your back, and a small business owner can now just focus on why they started their business in the first place.
Because you talk to a lot of small businesses, they're just really, at the end of the day, very passionate about something. Like why, you know, either of us started our companies, right? Or someone who starts a coffee shop, they're usually very passionate about coffee. Or someone who starts a pet store, they love animals, you know. They have something that they're really passionate about. And I think these days with AI, you can spend a lot more time on that thing and a lot less time on the things that are kind of more of that business back-office thing that, you know, every business needs to do. And that's why, like, I think things like Co-Founder exist, to sort of free up time for small businesses to focus on the thing that they love.
And we honestly see it in our metrics. And the government sees it in their metrics as well. The government releases sort of, like, census data on how many businesses are getting started every year. It actually releases, I think, on a monthly basis, and we are at an all-time high.
LubaWow.
EddieEver. It's a trend that started since Covid, and has persisted and gotten even bigger because of AI. And I think the reason why this is happening is because it's easier and easier to start a small business, right? Like, just imagine 20 or 30 years ago: you have to have a lot of capital. You have to have a lot of labor. There's a lot of, like, compliance things that, like, you can't possibly know except by reading, like, a, you know, a book somewhere.
But now with software like Gusto, and, you know, Etsy, where you can sell things on a marketplace, or Shopify, or Stripe, where you can accept payments, all these sort of, like, building blocks are there, and a lot of the friction points, the really difficult things about starting a business, have now gone away. It's still hard to start a small business. But it's much, much easier than it used to be. And now with AI, I think it's kind of like we're seeing another step-level function in terms of the ease of starting a small business. It's taking care of a lot of things that a small business would normally have to take care of. And small businesses just tend to be very entrepreneurial, right? They're kind of, like, very open to using AI tools to help run their business.
LubaWhat are your hopes and dreams of what role Gusto would play for small business owners, let's say, in five years?
EddieWe want anybody who wants to start a business, who has an idea of starting a business, to be able to do one, right? Maybe they have a serendipitous conversation or moment or something that happens that sort of implants, like, a dormant idea. And one day that idea, like, opens up and turns on again in their brain, and they decide, I want to start a business, right? And my dream for Gusto is that they'll think of Gusto and be like, I can absolutely do this. And there's no, like, sort of, like, operational or capital or knowledge or legal reason why I can't do this. I could just do this, because Gusto makes it very, very easy to do. That would be my goal for Gusto.
LubaSo obviously right now it's a really exciting chapter for you with AI. You're back to building, back in the trenches. What are you still insecure about?
EddieI think, like a lot of things that are early products, we still have to iterate to find exactly, stronger product-market fit. So I think with Co-Founder, I think we found something that is resonating with customers. But there's still a lot more that we have to learn. And so I think for me, it's almost like the first month of starting Gusto, where we ship something, people love it, but we still have so much to learn about how customers want to use it, whether they'll continue to use it longer term. So I think we just have to, like, kind of go back to that very humble, like, beginner mindset of building a new product, and just learn as much as possible from our customers, because we're not going to have all the answers right now.
LubaWe're going to wrap up with a quick lightning round.
EddieOkay.
LubaWhat is it that lights you up, outside of work and outside of building escape rooms?
EddieWell, I love, like... we love traveling, you know. And we love traveling with our dog, so it's kind of like going on adventures, both in the city as well as outside of the city. And, yeah, these days, like, actually, I've been focused a lot more on health. And so just kind of, like, learning about how to be healthy, going to the gym. Those are things that also bring me a lot of joy right now.
LubaHow many times a week do you go to the gym?
EddieI try to go, like, 3 or 4 times a week.
LubaAnd what's your routine? Are you lifting, or are you doing more...
EddieMore lifting focus right now. But I try to switch it up. So these days I'm a little bit more, like, trying to focus on building strength than anything. But it's fun. It's just, like, you know, for me, it's, like, a thing that I never really spent that much time on. And it's been fun to just learn a new thing.
LubaWas there a trigger for you to start spending more time on your health?
EddieWhen I turned... I'm 43 right now, but when I turned 40, you know, I was just like, okay, 40 is getting up there. And, you know, I love life. And I kind of had this thought that I want to live as long as possible, because, like, there's so much... I'm just enjoying life so much. And so the way to do that is just focus a little on health. So when I turned 40, I kind of had that, like, epiphany that, like, life is short. And so you should sort of invest in yourself.
LubaIf I were to shadow you for a day, what would be a thing or things that would surprise me?
EddieHmm. I think probably how positive I am. I tend to be a pretty positive person. I think people would describe me as very, very hardworking, but also maybe humble, and always kind of having that beginner mindset.
LubaAnd what's something you no longer chase?
EddieI think when I was younger, I was probably more financially motivated. And so now, like, I don't really chase or think about money all that much.
LubaAnd last but not least, your life philosophy in one sentence.
EddieBe positive.
LubaI love it. Eddie, thank you so much for your time.
EddieThanks for having me. That's really great.
LubaAwesome.