00:02:15 · Miguel Armaza, Michael Sindicich
[00:02:15] S0: You were a pre med student. In a parallel life, you would be operating a surgeon table, What happened? Why did you decide to pursue a different path? [00:02:29] S1: Yeah, it's a good question. I had thought that I was gonna be a doctor since I was in junior high. And so I remember I went to go watch, one of my friend's dad's was an orthopedic surgeon. So we went and we went and saw three live surgeries in the OR. It was an awesome experience. He was like, First things first. And he plugged in his iPod and he started playing ABC by Michael Jackson. The people in the room were dancing. By the way, the guy was asleep and ready to get his knee operated on. But it just looked like such a fun job. And so ever since watching those surgeries, then I was studying really hard in school. I was getting great grades and things like that. And I was also, when I got to high school, was working in a lab at the Keck Graduate Institute nearby in the Claremont Colleges. Ended up publishing some research as well on protein assays. Went to UCLA on the pre med track and I was also a track and a cross country athlete as well. And was going through, you know, kind of the track. And I found myself my senior year, the summer, me and some friends ended up starting an insurance brokerage to make some money. And my mom was an insurance agent. And we thought it'd be cool to build an insurance brokerage and do something to generate some income. And that ended up turning into like 50 licensed agents, our friends and people from school. Were you [00:04:02] S0: managing them?
00:04:02 · Michael Sindicich
[00:04:02] S1: We were managing. There was about six of us who started the company. We had an office in Beverly Hills. We were like sleeping on yoga mats. We were showering at the gym next door. And at the same time, I was doing my honors thesis and I was a psychology biology major. And I would go scooter back from the Beverly Hills office to school to do labs and then I'd work in a basement doing brain surgery on rats. So I was essentially implanting cannula into the brain and we were testing out different drugs and how they can help solve PTSD and depression and build more resilience. Between doing that and then building a company, I was like, Wow, this is actually really fun to build a company and to employ a bunch of people and really drive toward a mission. And so a lot of people actually take a year off before they go to med school. They study for the MCATs, the big tests, before you go commit to another four years of schooling or so and then into the medical track. And so that's what I did. My friend and I, we decided, let's actually move up to Silicon Valley for the year. He was telling me, trust me, my brother, he's in startups. It's amazing. Look at this thing. And so we came up and we called his brother on the way up and said, hey, we're gonna come up here and do you have a place for us to stay? Anyone who has anything available? And and my mom was like, yeah, I'll see you guys next weekend. You know, she thought we were gonna go up and come back real quick. But he ended up connecting us with a friend at a house that he was living in that said that we could rent the shed in the backyard in Palo Alto for $600 a month, by the way, which is really expensive, you know, as a new grad college kid. But at the same time, I was always kind of hustling. So I had a drop shipping company where I would sell iPhone cases or gym workout tanks and ship them from Amazon or Alibaba and sell them for a pretty good profit. So we could kind of get by for a while. We were still doing the insurance company at the time, so it works as like residuals. Once you have sold someone, if they stay on the policy, keeps going. And so we came, we got to Target, we rented air mattresses, little twin sized air mattresses. We put them in the shed. The same on the way up, I reached out to a Craigslist opportunity to basically teach chess after school to students.
00:06:18 · Michael Sindicich, Miguel Armaza
And the guy would meet me. He met me in San Jose. I interviewed with him on the drive up and ended up getting the job, which is like $50 an hour, which is pretty good, as people will pay in the Bay Area a lot of money to teach their kids chess. And so that's what we were doing while we were, you know, kind of figuring out what to do and applying to different jobs. And it was just incredible. It was like this insane hacker house. So, like, there wasn't a TV. There was a projector. [00:06:46] S0: What was the name of the house?
00:06:46 · Miguel Armaza, Michael Sindicich
[00:06:46] S0: What was the name of the house? [00:06:47] S1: There was no name. No name of the house. It was on Greer Street, so we just called it the Greer House. But I wrote a LinkedIn post about this, actually. So my friend's brother who lived in the house, he started a company called Socket. My friend is now the head of sales there. They just raised for a billion dollars. The guy that was living in the garage sold his startup to Box, took some time off, and then ended up being one of the founding engineers of RAMP. And then he went to go help his brother start his company called Cognition. You know, Devin, the software engineer? So him and his brother were building that. Now he's gone and started his own company and Cognition is taking off. It's actually where Art went to go work now. Absolutely. Yeah. And I was very early, ended up interviewing at Navan. And at the time, we were about six people and nobody. But now, it's grown to a lot bigger. So this house was just really incredible. It was an incubator of startup y tech kind of things. And it was so much fun. And after about a year, I kind of made the decision of like, wow, I just really love the whole startup scene, Silicon Valley, companies and riding the Navan rocket ship, hopefully to the moon one day. And that's when I decided that I probably won't go back to med school. Sometimes I think about it maybe in a couple years in a decade or something. If I ended up wanting to do something else, then I could explore it. But I'm having a lot of fun right now. [00:08:17] S0: Did you ever take the MCAT?
00:08:17 · Miguel Armaza, Michael Sindicich
[00:08:17] S0: Did you ever take the MCAT? [00:08:18] S1: I never took the... I took a lot of practice tests, for the MCAT, but, yeah, I never actually took it. [00:08:23] S0: You mentioned chess. I actually did not know that you were that good at chess, that you could actually teach it. If if you're gonna teach me chess, how do you assess whether I have potential or not? And what's important? What do great chess players have in common?
00:08:38 · Michael Sindicich
[00:08:38] S1: I would say, first of all, I'm not that good at chess. This was more of like an after school program for little kids. But a really funny story. So six months into working at Navan, I walked by Ariel's desk. Ariel's the CEO and founder. And I look at a picture on his desk and I say like, Is that Sivan? And he was like, How the fuck do you know my son's name? And I was like, I taught him chess at Juana Briones. Yeah. So he was in kindergarten at the time. So imagine the students I'm teaching are more like, you know, okay, it's an after school program. Parents are working. Let's like corral everyone, try to teach them how to play chess, also a little bit of daycare. But then all the way up to, you know, sixth grade or so, those chess players can actually get very competitive. I just think the most important thing about chess is one, having a strategy for the opening, but then two, kind of understanding every single move that your opponent can, come back with and then how does that change the game of the future. And it's a lot of if thens. Right? So... And I think that that's actually, I find it pretty helpful in the company and as we're thinking about strategy and growing the company, which is like, if someone does this, then we'll do that. If we do that, then we unlock this. If we don't do this, then this is the ramification of it. And to me, chess is one big, like, if then kind of statement of, like, how can you position yourself in the best way so that your opponent basically has less opportunities of if thens, and you have more opportunities of if thens.