Season 4, Ep. 11 – Founder to Founder: Andrew Greenstein, CEO & Co-founder, SF AppWorks

Transcript

(THE FRONTIER THEME PLAYS)

Teja (00:00:05):

Yo. Yo. What’s up y’all? Today we had an awesome conversation with Andrew Greenstein. We talk Miyamoto Musashi, anime, a little bit about business. You guys will really dig this one. Peace. (THE FRONTIER THEME FADES OUT)

Andrew (00:00:22):

Nashville? It’s like Nashville, Austin and New Orleans. Like, that belt of live music where everyone has so much talent. Yeah. So, if I were trying to be a musician, I’d go cut my teeth there.

Teja (00:00:35):

Have you been to New Orleans a lot?

Andrew (00:00:36):

So I’ve only been twice, and both times, it was for a bachelor party. (Teja: Yeah <laugh>.) So I don’t know like, what version of New Orleans I saw, but I’m not allowed to talk about it.

Teja (00:00:46):

What’d you think about the food?

Andrew (00:00:48):

Oh, amazing food.

Teja (00:00:49):

I think that it’s the best I’ve ever had, like, flavors and shit. Like, every restaurant was fucking good. I don’t know. (Andrew: Yeah.) We were also there for a bachelor party, so, you know, who knows?

Andrew (00:01:04):

I think you can make a strong argument. It’s such a unique style.

Teja (00:01:08):

So you’re a musician, right? Like, you kinda trained up as a musician. Did you school that or did you…

Andrew (00:01:15):

No. I did a lot of music in high school. Like, all the bands you could do: marching band, rock band, orchestra, symphony, all that stuff. And then I went to college as an English major, but tried to get into band, wasn’t quite good enough. So, you know, I still did like, some of the club bands. I was in the Latin session band. But it’s been something that I just have always wanted to continue working on, and I feel like I’m actually better now than I was back then. So I’m still on an upward trajectory, and you know, I don’t know if you ever think about like, second careers, but (Teja: Yes.) I definitely dream about the like, okay, second half of life, like, you know, maybe do the musician thing, but like, do it while not having to depend on it for a living. That’s a hard way to make a living.

Teja (00:02:10):

Yes, totally, and it adds like, stress into the creative process, I feel like. (Andrew: Yeah.) You know, where you just, it’s thrown a certain way, ‘cause you think it’s more commercially viable, and agents have their opinion on what you need to do, and…right? (Andrew: Yeah.) It’s a whole thing. <Unintelligible>. I think about a second career in like, jiu jitsu. I love training martial arts. (Andrew: Oh yeah?) Yeah, yeah.

Andrew (00:02:34):

I was thinking about doing jiu jitsu recently.

Teja (00:02:36):

Dude, okay.

Andrew (00:02:37):

Yeah. Gimme the pitch.

Teja (00:02:39):

So you’re in California, SoCal is like, basically where a lot of Brazilians go, SoCal and like, Miami, and you have a ton of good schools in SoCal. In NorCal, you have like, a couple good schools. Carlson Gracie’s up there, it’s got Kurt Osiander in San Francisco. That’s a really good gym. Yeah, check it out. Actually, let me see if I can recommend you.

Andrew (00:03:03):

What’s like, what’s gonna be my like, first year, second year, and third year of jiu jitsu, if I do this? Paint me a picture.

Teja (00:03:10):

It’s hard to tell from the video, but give me a sense of like, your physical stature. Like, how tall are you? How much do you weigh? Do you weight lift currently?

Andrew (00:03:19):

Okay, I’m 6’ 1”. I’m a little overweight, 230. I play a lot of basketball, and I run, so my lower body is really strong. (Teja: Gotcha.) My upper body is not very strong, and that’s one of the reasons I wanna explore and do more for the full body, you know, strength.

Teja (00:03:40):

Gotcha. okay, so, if you’re 6’ 1” and over 200, on average, you’re gonna like, bigger than probably the normal person in jiu jitsu, and so that’s gonna give you…

Andrew (00:03:51):

The big ones fall harder, you know?

Teja (00:03:53):

That’s true, but you’ll have a natural advantage in terms of…because grappling is very strength and size dependent, (Andrew: Yeah.) initially. Like, when the skill is like, early, size makes a hell of a difference. And so you’re not gonna have a super unpleasant time for the first year. Like, yeah, you’ll kinda feel like, “Man, there’s a 150 lbs guy or a 120 pound girl, you know, controlling me,” but it’s not gonna hurt, you know, ‘cause your body can handle it. If you’re like, a 135 lbs guy, you’re gonna get ragged on by everybody, and it’s gonna like, actually hurt, not just hurt your ego. (Andrew: Yeah.) So first six months, it’s gonna feel like you’re learning how to swim, but the second six months, you’re gonna get the hang of it. And I would say around month 8 to like, month 12, you’re gonna probably tap somebody. You’re gonna like, feel how it feels to like, hit a submission, and you’re gonna be like, “Holy shit, this is like a superpower.”

Andrew (00:04:58):

That’s when you get hooked.

Teja (00:04:59):

You’re gonna get addicted. Yeah, for sure.

Andrew (00:05:01):

How long have you been doing it?

Teja (00:05:03):

Maybe eight years.

Andrew (00:05:05):

Oh wow. Is there a belt system?

Teja (00:05:07):

There’s a belt system, if you do gi. There’s no belt system if you do no gi, but you kinda get promotions, but you don’t wear a belt. And the gi is like, a more traditional kinda system, where like, you wear like, a kimono and shit. No gi, is basically, you wear like, a rash guard and shorts, and it’s more akin to wrestling. And so there’s a little bit of a cultural difference.

Andrew (00:05:38):

I see. I actually wrestled for a little bit in junior high. A long time ago, but…

Teja (00:05:43):

Sick. Yeah. So you understand like, the intensity of grappling, and like, (Andrew: Yeah.) push/pull. So, if you’re gonna learn one martial art, I think jiu jitsu is the best one, ‘cause you’re grappling, you’re sparring every day that you go train, (Andrew: That’s cool.) and so, yeah. Like, a lot of traditional martial arts, you’re not sparring. You’re just like, learning technique, and then like, you go, and you spar, and you’re like, “Oh shit. This is totally different than the sitting pads,” (Andrew: Yeah.) you know? But jiu jitsu, you learn a technique, and then the last 30 minutes of class you’re like, in a live wrestling match, trying to utilize the technique.

Andrew (00:06:22):

That’s cool. What injuries do I have to look forward to?

Teja (00:06:25):

Fucking knee shit, (Andrew: Knee shit.) shoulder shit. Yeah <laugh>.

Andrew (00:06:29):

Shoulder dislocation is gonna be the first one.

Teja (00:06:34):

<Laugh>. I like, partially tore an ACL, but it recovered, and I kinda feel like, it’s one of these things where, if you’re serious about jiu jitsu, like, you train twice a week or three times a week, let’s say, it forces like, your life to be in order. What ends up happening is like, you actually start, for example, like, drinking less or eating better, sleeping earlier. Like, it kinda, if you’re enjoying it, it forces discipline into other aspects of your life, and as it does, your injury risk drops. Like, the times I’ve gotten injured, there have been weeks where like, I’m working 12 hours a day, I go to a happy hour, you know, I drink, and then I wake up at five, yeah, to go train at 6 a.m., and gonna get hurt, you know? So if you’re disciplined about the other shit outside of jiu jitsu, you probably won’t get hurt, generally. Yeah, you should do it man. Just go to like, a class. Commit to like, a month.

Andrew (00:07:36):

Alright, I think I’m gonna try. I’ll send you an update.

Teja (00:07:41):

Yeah. It’s the nerd’s martial art. It’s like, there a lot, the guys who do well in it are like, cerebral, they like to solve problems. The meatheads basically go to MMA and are wrestlers <laugh>.

Andrew (00:07:54):

Yeah <laugh>.

Teja (00:07:56):

Okay. So San Francisco, born and raised there, musician…

Andrew (00:08:01):

Born in Chicago, raised in San Francisco, or south of San Francisco.

Teja (00:08:05):

How has the city changed in the last 20 years?

Andrew (00:08:08):

There’s a lot less music in the city. Music and art, music venues, like, a lot of the classic ones have shut down. You know, there’s definitely, art is getting priced out. There’s a lot of wealthy people and a lot of low income people, and then there’s this huge gap, and it’s been really hard for the city to fill in, particularly with the artist community. So we’ve seen a lot of closures in great clubs that we used to go to. But you know, it’s a pretty resilient city, and there’s still an incredible culture here. I’m hoping that, you know, [the] city can figure out a way to restore some of that magic that makes it great.

Teja (00:08:51):

Yeah, like, what’s the opinion of like, a San Fransican on this like, the tech ecosystem that exists there?

Andrew (00:09:00):

I feel like it’s one of those, you know, “rumors of our death were exaggerated” type of things. (Teja: <Laugh>.) Look, I’m like, totally on board with the idea of, “Hey, I want to go get a, you know, bigger house,” or you know, “I’m gonna go somewhere else, and I’m gonna work my magic there.” Like, there’s tools you can do that, you know. We have people in our company all over the world, so I have no issue with that. But you know, I still like, when I talk to people here, maybe we’re just drinking our Kool-Aid, but you know, everyone says that like, this is still where people are coming to raise money and then start businesses, and you have a lot of experts here, you know? Like, the top minds in AI are still here. So, you know, I think it hasn’t really changed in that sense, and, if anything, it might even be getting better.

Andrew (00:09:46):

But you know, the downtown is pretty empty. I mean, I think we’re really lagging in terms of going back into the office. That’s sort of in line with our liberal culture mindset, but I even feel like that’s starting to change. You hear startup CEOs starting to, you know, talk about, “Hey, you know, we’re now pushing to bring people back into the office,” and it’s not ‘cause it isn’t working to do the remote thing. It has been working, but it works best when you already have a culture, and then you go remote. So we all experience that. But if you have to build a culture fully remotely, that’s a big challenge. So I think that’s where a lot of pressure’s coming from.

Teja (00:10:30):

You have to like, have meetings where 20 minutes you don’t talk about work. It seems like that’s how you kinda have to get to know people, you know?

Andrew (00:10:38):

Yeah. And I mean, I do believe in in-person, so I say this not having an office I go into every day. You know, most of our team is in Romania, and we have an office there. We never require people to go into an office. It used to be a competitive advantage for us. Now it’s not. (Teja: Yeah.) But that said, you know, we love when people go in the office. We go there as much as we can. We’ve gone there like, 10 times a year, before. Now we go about three, four times a year. And when we’re there, we do our best work in the sense that we are spending as much time as we can together. And a lot of it’s not talking about work, it’s just getting to know the human that you’re, you know, trying to solve problems with. So I’m a big proponent of that part of it.

Teja (00:11:25):

Do you guys fly in everybody from like, Romania and elsewhere to the office for those days or…?

Andrew (00:11:33):

Yeah. Yeah. So there’s 50 of us in Romania, and then (Teja: Wow.) five of us elsewhere, so we all fly.

Teja (00:11:42):

Wow. Holy shit. That’s crazy.

Andrew (00:11:46):

Have you been to Romania?

Teja (00:11:48):

No, no, I haven’t. How is it?

Andrew (00:11:50):

It’s awesome. Our office is in a city called Cluj. It’s in the heart of Transylvania. (Teja: Dude.) Yeah. Like, I didn’t even know it was a real place until I started going there. And it’s amazing. It’s this university, like, a university city. I think there’s 400,000 people in the city and then another hundred thousand students. So there’s like, 11 universities I think, and most of them are technical. So you have this incredible like, hotbed of intellectualism and education, and so that’s one part, really quickly growing city. And then you also, Romania had a dictator in the late ‘80s, and when the dictatorship fell, I think there was a lot of support from the West and from the U.S., and so the country developed [a] strong relationship with the U.S., and you know, there’s a big military base there. There’s a lot of diplomacy. I remember when, during the pandemic, when we got the vaccine, Romania got the vaccine at the same time. (Teja: Damn.) So there’s this close ties and great vibrant culture, credible people, credible education system, credible talent.

Teja (00:13:05):

Maybe I’m like a dumb and uncultured American, but when I think about Romania, I think about like, the fucking vampires.

Andrew (00:13:11):

I mean, they lean into it now. (Teja: Yes.) You know, Dracula’s Castle and all the stuff around it, but, you know, it’s kinda rooted in a similar real story, Vlad the Impaler. He was actually like, a great military tactician, I’m probably gonna butcher this, but I think he was captured as a child by the Turks and tortured, and he just became a horrible, hurt person because of that, right? (Teja: Wow.) Hurt people hurt people. Isn’t that the saying?

Teja (00:13:38):

Yes. Yes.

Andrew (00:13:39):

So then he, but he was a, you know, he escaped, and then he went back, and he drove the Turks out of Romania, or maybe there were three regions at the time, but drove the church outta the area, and then he started ruling. And it’s like, I guess, an interesting experiment on how to run a country, but his like, thing was obviously impaling. (Teja: <Laugh>.) It was punishment for everything. It was like, “You killed someone, I’m gonna impale you. You stole some bread? I’m gonna impale you too,” (Teja: <Laugh>.) and he was horrible. I mean, he was impaling, not just the people that were committing the crimes, but like, they have a torture museum at the Dracula Castle, of course, why not, but they also said that you put out a gold brick in the middle of the city square, no one would touch. Like, crime disappeared. Not advocating for this form of punishment, but it’s just interesting.

Teja (00:14:28):

It is. It’s like that shock and awe style punishment. I bet Singapore is similar, right? Like, you get caned if you basically do anything like, spitting gum out or something, you know?

Andrew (00:14:37):

It’s really clean there.

Teja (00:14:40):

It is, yeah. I read on Reddit, something interesting about vampirism. Basically, you may have known this, but like, they used to think that rabies, like, when a human being got rabies, that person was a vampire, because, basically, they showed all the symptoms of what we would think of what like, a vampire would have. Like, pale skin, they hated the strong odors like garlic, (Andrew: Oooh.) they apparently couldn’t bear the sight of their own image, they were going crazy.

Andrew (00:15:14):

Oh, that’s so interesting.

Teja (00:15:16):

Yeah. So when there were like, rabid wolves or dogs, basically, you know, in eastern Europe, and you got bit by a wild dog, and you got rabies, or wild rodent or something, they would be like, “That person’s fucking possessed.”

Andrew (00:15:29):

That makes sense.

Teja (00:15:31):

Yes. You know, get bit by a bat. Yeah.

Andrew (00:15:33):

Like, everything gets inspired from real events, in some way.

Teja (00:15:37):

So do you like anime, or no?

Andrew (00:15:40):

I do. I’m like, so this is actually the same way I am about music, where I just obsess over a small batch of it, and not like, widespread. So like, I’ve seen probably five anime in my life. Obsessed.

Teja (00:15:53):

Okay. Which ones?

Andrew (00:15:55):

So my all time favorite’s Kenshin.

Teja (00:15:58):

Okay, solid. Yeah.

Andrew (00:16:00):

Yeah. And I’m like, currently, and I say currently, but I’ve been trying to get through it for like, two years, working my way through Naruto.

Teja (00:16:08):

Okay, yup. Classic.

Andrew (00:16:09):

There’s like, thousands; it’s endless at this point. And like, 400 of them were filler, and I just couldn’t get myself to skip them. But you know, when it gets good, it gets really good. Actually, I don’t know if it counts as anime, but I watch that show Castlevania.

Teja (00:16:27):

Yes. (Andrew: Yeah.) Yes. About Vlad, right?

Andrew (00:16:30):

Yeah, yeah. And then my other favorite, I guess I would say my number two favorite, behind Kenshin, was Kuroko’s Basketball.

Teja (00:16:38):

I haven’t seen that one.

Andrew (00:16:40):

If you’re into sports or basketball, it’s short, it’s only three seasons. It was awesome. What’s your top four, I guess?

Teja (00:16:48):

Yeah, okay. So my like, Mount Rushmore, I love JoJo’s Bizarre Adventure. It’s like, I think it started in the ‘80s or maybe early ‘90s, and it’s kinda continued on, and it’s really good. It’s on Netflix. I would start at like, the Egypt arc, which is like, the second season. It’s really good.

Andrew (00:17:10):

You don’t need to know the first season?

Teja (00:17:14):

I mean <sigh>, it’s not as good, and like, you can get the context based on that season. And then I really love this older anime called The Legend of Galactic Heroes that’s on CrunchyRoll. And it’s like, a 150 episode series that basically deals with like, a galactic… it’s like Star Wars, but an anime, and a different universe (Andrew: Okay.) where both the empire and rebels are like, led by sympathetic figures.

Andrew (00:17:51):

Okay. So yeah, there’s good and it’s dynamic, right, that people are faulted characters. I love that. Like, when the superhero movies started turning towards like, the darker, you know, faulted characters, that felt much more real to me.

Teja (00:18:08):

Totally. And like, watching this show with like, nuance and depth or an anime with that, actually kinda inspires me at work. Like, there were some like, you know, strategic or diplomatic issues they were trying to figure out in Legend of Galactic Heroes, and I watched an episode where I’m like, “Oh, I’m fired up to like, do business,” you know? It’s <laugh>, so that’s, yeah. That’s a really good one. And then, let’s see, for third, I like Hunter x Hunter. Those are my top 3, I would say.

Andrew (00:18:45):

I just gotta finish Naruto in seven years.

Teja (00:18:46):

<Laugh>. In seven years. Yeah, I know. I tend to like, watch Anime sporadically. Like, I’ll watch through the episodes in a weekend and like, not watch it again for like, months, you know?

Andrew (00:19:06):

Yeah, it’s one of my plane watches, ‘cause I’m a married man now, and my wife’s not a not an anime fan, so thank you. And so I’m like…

Teja (00:19:12):

Are you a reader?

Andrew (00:19:12):

Yeah, I’m a reader. I love historical fiction. I try to rotate between like, some kind of businessy book, learn something from someone great, some kind of biography, or fantasy. You know, sometimes she reads. I’m reading Orphan X right now. I don’t know if you’ve heard of that.

Teja (00:19:33):

Yes, I read the series. It’s fucking good. Evan Smoak, right?

Andrew (00:19:37):

Yeah. It keeps going. I mean, he keeps dropping a new book every year now. One of my all time favorites is Shogun, historical fiction, James Clavell. I’m actually reading, I think it’s called Miyamoto? A predecessor to Shogun. Mistborn. Have you read that?

Teja (00:19:54):

Yes. Brian Sanderson. Yeah, I read that. That’s solid. 

Andrew (00:19:59): Those are three books. How about you? 

Teja (00:20:01):

So I’m a big fan of Sanderson. I love like, what he did with the Wheel of Time series.

Andrew (00:20:09):

I never read that. Probably should.

Teja (00:20:10):

Yeah. It’s solid.

Andrew (00:20:12):

He picked it up after the original author died, right?

Teja (00:20:15):

Yes. Yes. It’s a big ass series. It’s a commitment of like, a whole world, but it’s really good. I loved Stormlight Archive. That’s another one of his series.

Andrew (00:20:29):

I read like, half of it, and then (Teja: Yeah.) I like, I don’t know what happened, but you know, when you put down a book or a show, and then for six months, you don’t pick it up, and then you forget where you are, and you’re like, “Well, where do I even start? Which book do I start on? I don’t remember where I am.”

Teja (00:20:47):

Yes. That happened to me with that series, like with the latest book. I was like, I don’t even remember how any of this is relevant, (Andrew: Mm-hmm <affirmative>.) you know, and it kinda, if you don’t understand the world, it’s hard to read like, an epic at that scale. But Mistborn is great. You might like the Riyria series by this dude Michael…I forget his last name, but he wrote like, the Riyria Chronicles and Riyria Revelations. Like, the Reddit fantasy subreddit is great for book recommendations, if you ever want book recommendations. 

Andrew (00:21:22):

Alright, I’m gonna get into that. Riyria, you said?

Teja (00:21:25):

Just great fantasy reads, you know? Alignment to the protagonist is like, lawful good or neutral good. They’re good stories, full of intrigue, you know? It’s cool. I think you might also, it’s one of my favorite books, it’s called San Guo Yan Yi: Romance of the Three Kingdoms, and that’s the book that Dynasty Warriors was based on, (Andrew: Mmm <affirmative>.) and there are a bunch of like, books and movies that are like, offshoots of that Three Kingdoms book. That’s historical fiction. So it’s called the Romance of the Three Kingdoms, ‘cause it’s a romantic account of the actual history. Yeah, and so it’s like the Warring States period in China, you get fucking really genius strategists, you know, fighting each other and like, the different tactics they use in battle. It’s sick.

Andrew (00:22:23):

I love that. I’m gonna check those out, and put them on my list.

Teja (00:22:26):

Ten years ago, or maybe, I don’t know, 20 years ago, I guess I was in college, I would skip class and the reading to read that book <laugh>. 

Andrew (00:22:37):

<Laugh>. You were studying the wrong thing. 

Teja (00:22:40):

<Laugh>. Yeah. Do you feel like fantasy inspires you to be a better business leader? Or do you just like doing it?

Andrew (00:22:48):

I think I love, you know, the hero’s tale. (Teja: Yes.) You know? We’re all the heroes of our own story, and so I think, you know, it’s definitely aspirational to see amazing people doing amazing things, and fantasy takes that to a whole new level, and it’s, you know, like, you were talking about getting, you know, pumped up. It really makes you feel like you could do great things. You could be a hero, you know, you put yourself in their shoes, and yeah. And we go to our work, and we try to be, you know, we try to be the heroes. So I think that it’s helpful.

Teja (00:23:23):

I feel similarly. I feel like it creates a nice, mental, positive narrative that allows you to like, you get a baseline, almost in your head, for like, how you should act at work, you know? ‘Cause I kinda feel like a lot of company founders can be, I don’t know, kinda selfish. And so I feel like the selfless morality of the heroes in those books like, really appeals to me, for some reason.

Andrew (00:23:56):

Yeah, that’s a good point.

Andrew, via SF AppWorks promotional video (00:23:58):

(VIDEO CLIP AUDIO PLAYS) Hey, this is Andrew from SF AppWorks, a software development shop that helps companies develop websites, apps, chat bots, voice bots, and pretty much any kind of custom software. I wanted to quick….(VIDEO CLIP AUDIO FADES OUT)

Teja (00:24:08):

Tell us about like, SF AppWorks, dude. Like, how’d you guys get started, and like, you know, how’s it been going? [I] checked out the site. It’s cool that you guys have like, a timeline based on the evolution of the business.

Andrew (00:24:20):

I was in law school at the time. I was really trying to break into some kind of music career. I had already eliminated being a musician as possible. So then I was like, “Okay, maybe I’ll be a music lawyer,” and I was trying to find jobs in that space. It’s like, you know, to be a music lawyer is really to be on the wrong side, so to speak. (Teja: <Laugh>. Yeah.) You’re the evil empire, usually. Not always. But I didn’t see a lot of opportunity there, and I asked my brother who was a lawyer, turned entrepreneur, I was like, “How do I get into the music industry?” He’s like, “Start a company,” and it had never occurred to me like, we grew up in Silicon Valley, and it never occurred to me that was something one could do. So I went to Office Depot, and I bought like, a nameplate, and I was CEO of a one person company. Let’s do this. And I started this company, and I met my current co-founder chair, and we built a music collaboration platform. So we wanted to basically create a Wikipedia for music creation. Let other musicians record, edit, branch off, and see what comes out of it. And we actually, you know, did that for about three years. We got on stage at TechCrunch Disrupt, raised some money, ended up partnering with Linkin Park.

Andrew (00:25:39):

Had a lot of good opportunities, but the product was just so hard to state. We couldn’t get our product market stated; it was complicated. We needed hardware, we were trying to do audio and video, and it’s always a great lesson for me in simplicity, ‘cause this was 2008, and we were doing smart things in terms of like, making it all server side, you know, which wasn’t popular at the time. Like, Cloud wasn’t popular at the time, but it was so complicated. And like, the same time we were launching that company, there was another music company launched called SoundCloud, and their mission was to move music. Like, that simple. You want music, you have it here, you wanna move it there. It was a Dropbox for, eventually, they became a music platform, but so yeah, it just wasn’t simple enough.

Andrew (00:26:22):

It wasn’t easy enough, and the company didn’t work out. So Darius and I, my co-founder, we wanted to do another startup, but we didn’t know what it was, and we were a little burned from kind of raising money. And so we thought, well let’s, why don’t we take on some startup like, work and think about it a little bit, and we can get some experience in different industries. And so he’s from Romania. He had grown up near Cluj, and he had a couple buddies, and he’s like, “You know, these guys have been coding at these companies for like, 10 years. They can help us.” So we made our first couple hires there, and we opened up shop, and we were, you know, I was doing product management, product development. We had a designer. And then Darius was the architect, CTO, and we had a couple coders, and we just started building websites and apps and thought, you know, did this for a year or two, and then do our own startup, and that was 12 years ago.

Teja (00:27:20):

Okay, so there’s like so much there. So, burned by the raising money process. Did you guys just like, not like raising money, or it’s kind of a pain in the ass. I get it, but I want more. Tell me more. Why did it suck? Why are you over it? That sort of thing.

Andrew (00:27:38):

I think I just, I wasn’t necessarily burned by the <unintelligible> or anything. I was, and I didn’t mind raising money, but it was all I was doing, and you know, I felt like so much of my life was just calling people, pitching them, trying to get more money, and soon as you get the money, you know, you’re trying, you’re already looking for the next one. And you know, I just, at the time, I thought we could try to do this again, but it would feel much better if we had cash flow from the start. (Teja: Mm-hmm <affirmative>.) And so it was more about the decision to be a cash flow business and, you know, not spend beyond our means, and it’s been nice, because…oh, I think there’s a lot of advantages to having a board or having people accountability, expertise, but it’s really nice being able to call your own shots and do things the way you wanna do them.

Teja (00:28:28):

We bootstrapped for like, eight years, and we raised like, our first venture round like, last year. (Andrew: Congratulations.) It’s interesting. Thanks, man. Yeah. It’s been cool. But I totally know what you mean, where like, there are tradeoffs in both universes, you know, that you have to sort deal with, for sure.

Andrew (00:28:46):

Yeah. Well, I wanna hear your take, ‘cause you’ve seen the same business both bootstrapped and venture-raised. Like, how has the business changed, or how’s your experience changed?

Teja (00:28:57):

Building the business, you know, bootstrap, I felt like every, you know, day, we’re looking at the cash balance, you know. We’re reconciling, you know, planned versus actuals to understand what we can hire, what we can invest, to scale faster, to grow faster. We’re like, monitoring every dollar. But the upside of that, is you have control. You can call your shots, right? But then you’re like, constantly thinking about like, what if such-and-such happens? How much reserve do we have? Do we have to make cuts? Where are they gonna come from? But then, but it was fun, because I mean, basically over eight years, you get to learn like, where you think the key points are for investments to scale, right? And so, we got to a point, basically, in the pandemic, where we had some kind of acquisition conversations, inbound. We weren’t looking to sell the company. We were like, “Hey, okay, these people wanna buy us. Like, let’s talk about it.”

Andrew (00:30:06):

Nice. When those emails start coming in, you’re like, “Oh, I must be doing something right here.”

Teja (00:30:11):

A hundred percent. And, you know, we were just trying to build like, a cool business, like, have fun doing it, you know, get people paid, get companies built. Like, that’s fun shit, you know? We were like, “Well, it’s probably not a good time to sell right now, because we’re like, there’s a lot of opportunity in the market.” And so then, we were like, “Let’s go and see if we can raise some money.” So we ran like, a pretty tight process and we ended up finding a fund that, I think, matched our worldview, and we got sheets from like, west coast funds, and it’s super interesting. I could tell you all about that experience on how they operate. Okay, you wanna know? (Andrew: Yeah, hit me with it.) Okay, so west coast vibe is super interesting, where we had always grown like, 40, 50% right? Like, profitably solid growth. And I remember conversations with them were basically like, “You guys gotta grow 100% a year, at least, and like, we’re gonna give you the money to do it.”

Andrew (00:31:15):

“What is this shit? 50%?”

Teja (00:31:19):

Yeah <laugh>. Hundred percent. Totally. And I was like, “We have never done that. Like, you can give me a billion dollars. I don’t really know how to do that. So, we’re gonna try to ramp into that, but like, I’m not gonna pitch a plan that involves us doing that and assign my credibility to that, because I don’t know how to do it. Like, we’re gonna figure it out.”  And that’s sort of when I was like, man. These people on the west coast, they just fucking go for it. They’re like, “Fuck it. We’re gonna figure it out. This is the point we wanna hit, we’ll raise the money, we’re gonna go do it.” (Andrew: Yeah.) I admire that, because that’s ballsy as fuck, and it’s almost like, it’s so adamant. You know, like, “I don’t know how we’re gonna do it, but we’re gonna fucking do it.” (Andrew: Yeah.) But to me, I’m like, we’re like, playing with like, people’s lives, we’re playing with the business, like, we’re playing with commitments that we’re making. So, I felt uncomfortable with that, personally. I think over time, I just realized like, that’s just how the game is played. Like, that’s how they stack incentives, incentives down from the LPs, from the fund, to the company. Like, you all know that that’s not a reality, but you have to pretend as if it is and make that happen. Like, I get that now, but at the time, we were like, “That seems kinda weird.” 

Andrew (00:32:37):

Well there’s a little “aim for the stars, land on the moon” to that too, right? Like, ok, go for 100% so you land at 50. If you go for 50, you’re gonna land at 25, whatever.

Teja (00:32:47):

Yes. Exactly. And like, I get that now, but to me, it’s like, if I’m gonna say we’re gonna do something, I want to fucking damn well know how to do it, you know? Personally. And so we found a fund that, when we pitched the plan, which was basically like, “Hey, we’re gonna keep doing what we’re doing. We’re gonna do a little bit more of it. We’re gonna invest in these key areas that we think are really important to our customer base that they’ve been asking for, but we just have not been doing, ‘cause we’re monitoring cash flow and trying to be profitable.” They’re like, “Cool, yeah, we get it, and like, we wanna try these things to grow faster.” They’re like, “Cool, we get it,” and it was like, super aligned, so we got the deal done, and I would say, a year later, you know, August, it will be one official year, it’s been awesome, because it’s forced me grow into role where I’m not as operationally focused, where I’m trying to constantly fine tune the machine and make it more efficient. I’m not focused on like, how do we hire players from other companies that are awesome to come in and build process for us and go and close deals. And that’s been like, fucking cool, ‘cause that’s just cool experience to go through, I think, as business person, and it’s like, it’s sounds so trivial, but it’s like, you now have to think about how do you create an environment where like, you have generals that are making strategic decisions, versus you’re actually making all the strategic decisions? Like, kinda all you have to do as a CEO is like, really set the vision, and the vision is like, a sentence, and then trust that people have the right intuition to align with that vision, based on the playbook they wanna run. So you’re like, at a really high level of abstraction, which is like, it’s actually insane to think about and like, sometimes I’ll come home from work, and we’re like, “This is fucking nuts. I can’t believe that I have this job. Like what?” So that’s been like, really cool, I have to say. It’s scary, but it’s cool.

Andrew (00:34:57):

I think the way to do that is to take vacations, because, (Teja: Yes <laugh>.) no, because, when you take a vacation, especially the longer one like, two weeks, three weeks, I just got back from my wedding honeymoon, my first time taking two weeks off, and I was pretty worried about it, but it was actually great, because the weeks leading up to it, we were like, “Okay, I’m gonna be gone. You know, like, here’s what we’re trying to accomplish while I’m gone, Just from a high level. We can’t solve everything in advance, so let’s just lay out the strategy.” And then everyone else needs to pick up the slack and, you know, make strategic decisions, like you said. And, you know, for the first, I don’t know, 10, 11 years, I was one of those like, I didn’t really vacation, but I was, you know, I’d always have my phone; I’d always have my laptop. (Teja: Yeah. Yes.) I would just work two or three hours a day instead of a full day. But because of that, (Teja: Yes.) I could go anywhere I wanted and be anywhere. And only like, the last couple years, I started trying to create the, you know, barriers and say, “You know what? I think it’s actually healthy to shift gears and not pay attention, decompress.” So yeah, weeks leading up, high level strategy, then you’re gone. You’re getting a fresh break, everyone else [is] picking up the slack and making those strategic decisions, and then you come back and everyone’s better for it.

Teja (00:36:06):

No, that’s so true. I’ve been trying to do a better job of that, myself. Like, it’s funny. Like, so we have a remote culture, too, but we have an office, and I’m currently the office with like, our of head of revenue, and our team is distributed, and when I work from home sometimes, it takes me like, two hours to like, have my brain warmed up, and then the come-down after work takes me like, two hours, you know? But when I’m driving to work, and I’m in the car and I’m playing tunes, and I’m like, having my cup of coffee, I can like, feel myself transforming into like, “that motherfucker”. (Andrew: Yeah.) And then I’m like, zoned in, and then when you leave, you’re like, deep, you’re shifting back into [a] normal person.

Andrew (00:36:59):

Yeah, that’s your own backend.

Teja (00:36:59):

So that separation is important, yeah.

Andrew (00:37:01):

I started, ‘cause I’m working from home, and I had the first breakthrough 10 years ago was, ‘cause when I first started working from home, I would just get up, and open my laptop, and start working from bed. (Teja: Yes <laugh>. Yes. Yes.) I was terrible. ‘Cause then all of a sudden like, you poison your bed; you poison your laptop. It’s like, all…so then I finally figured out I need a separate room. I walked through that door, and I’m now in work mode, and I leave that room, and I’m not in work mode. So I was the first thing, but recently what I started doing is commuting to work, ‘cause I have a dog, who is sat here next to me, (Teja: Aw.) and I now like, get up an hour before my first meeting, and I go for a walk around the block. It’s my commute to work, and it’s been really helpful for, kinda like you said, turn it on, turn it off.

Teja (00:37:52):

Oh yeah, dude. Oh my god. I would like, work late and then like, wake up in the five minutes before the first meeting, and like, we used to have like, our check-ins at like 7:30, and then I’m just immediately, you’re just slamming the coffee. I like taking nicotine, so I’m like, dosing myself with nicotine, and I’m not in the zone. And I’m like, this is not healthy. I feel myself aging extremely fast, but you’re like, whatever. This is what it takes, so I’m gonna do it. 

Andrew (00:38:26):

I used to do my meetings with Romania, it’s 10 hours added, so you either have to do them really early or really late. (Teja: <Laugh>.) And for the first three years, I would do them really late at like, midnight, (Teja: <Scoff>.) 1:00 a.m. The problem is like, you get so tired, so I would drink. Like, I would drink whiskey during a meeting to stay up, (Teja: Yes. Yes.) and I was the same way. I was like, this is not healthy (Teja: Yes.) and also not professional.

Teja (00:38:48):

Yes, totally.

Andrew (00:38:50):

So now, I have all my meetings in the morning, and I drink coffee (Teja: <Laugh>.) Coffee with whiskey in it, though.

Teja (00:38:57):

Totally. Yeah. Sometimes on vacation, that’s fun. Like, if you wanna like, write something, you know? That’s a thing. But yeah, no, dude. I totally feel you. Like, it’s kinda like when you’re an entrepreneur, it seems you’re always on, because you’re the backstop to every issue. And so I’ve been a lot more aware of the different kinda like, emotional and psychological states I’m in, and how that affects my decision making. You know, like, you might make a slightly different business decision if you’re on that dopamine high of your second cup of coffee, versus your fifth cup of coffee, versus your first drink. Like, you’re a different person, slightly. Yeah, I try to tell my team, “Don’t let me make any fucking important decisions after noon on a Friday. Like, from noon to six, like, do not put anything that needs my review in front of me. Like, that’s a next week item.”

Andrew (00:39:56):

“We’re shutting down that unit.” 

“What?!” 

“I don’t wanna deal with it.”

Teja (00:39:59):

<Laugh>. Yeah. So you guys started SF AppWorks, now I have to ask you, so like, is there a sense of like, ‘cause, you know, you guys are building a cash flow business, the growth is predictable, but do you guys ever look at like, you know, the next unicorn, decacorn, and like, “Damn, we should start a product company.” Is there ever that thought, or are you guys like, “Hey we’re happy making good money, building a good life for us in the company, and that’s good.”

Andrew (00:40:30):

Yeah, that’s exactly what we grapple with every day. (Teja: <Laugh>.) So like, we tried it, actually. We always thought, you know, I said when we started, we were gonna just do this ‘til we came up with a startup idea, and one of our first clients was a marathon training app, and it was really fun. And you know, we had some good growth early on, so we’re like, “Hey, you know, we should really go after this.” The founders of that company ended up, you know, when the growth spurted out, they ended up kinda giving up on it, so we acquired it. Like, let’s build this up. We tried to do that for a couple years, while we were running the business, and what I realized really quickly is, you cannot compete with other people at halftime, ‘cause they’re working 100%, and you’re working 50%.

Andrew (00:41:11):

They’re just gonna keep being past you. So then we had to figure out, you know, pick one or the other. So we went back to the more reliable, stable one. But you know, nowadays, of course, with like, now that ChatGPT is out, and this like, AI revolution, it’s like, definitely intriguing again. You know, and we definitely have conversations like, “Would we start another internal product? Like, could it be one that helps our clients, and then like, pivot all the way to it? Is there something that could help us in our workflow?” We have those discussions but it’s, you know, we’re very wary of splitting our focus and attention.

Teja (00:41:48):

And it’s like, how do you start the value, the opportunity cost of building the company that’s growing and that has market customers, you know, all that stuff, versus like, a new idea, where you can’t really measure anything to see what it’s worth, in terms of time. I definitely have shiny object syndrome, where I’m like, “We should build this other thing over here and go do this,” you know?

Andrew (00:42:14):

Yeah. One day, I think. I mean, it would be, we love the prototype and like, you know, we have some bench resources, where like, right now, we’re building a movie recommendation app on ChatGPT now. Like, the world needs another movie recommendation app, but at the same time, we’re like, “Let’s see what we can do here.” And it’s fun and interesting and, you know, say we could build little prototypes here, but we’re also working on an EV charging station solution, which is a growing area in Romania, but we don’t build them as products. We build them as prototypes. We put ’em out there for people to test and play with, and you know, I think if we saw some kind of like, yeah. If we hit a nerve, maybe it’d be fun to explore. Could we actually build a business unit that’s gonna grow this as a business and have its own leadership and stuff, so you’re not splitting your attention, but you’re making a calculated investment?

Teja (00:43:06):

Totally. It would be cool if you guys like, found like a third, I mean this is an idea <unintelligible>, but it’s like, [it’d] be cool if there’s a third partner that like, ran like, a studio, leveraging your bench, and like, that person would be responsible for like, prototyping ideas, taking them to market, and then ultimately finding a founding team to take it and scale that. Maybe you guys keep a piece of that business. I don’t know. You know? And that way, it’s like, you could build the company, but the company is taking a leverage that’s in a systematic fashion, you know?

Andrew (00:43:39):

Yeah. Yeah, if you find that studio, let me know.

Teja (00:43:44):

You can build it!

Andrew (00:43:46):

Yeah. That’s another interesting idea. You know, the idea of being more of like, a creative studio, than a development and design studio. I think we actually are trying to tilt a little more that way, as well. We’ve always put our chops on being an engineering firm with some design resources, and we’re trying to be more of a product and design firm with a really strong engineering arm. And that’s more project related work for me, which, you know, stepping outta that for a long time now, I’m stepping back into it. But it’s also really exciting, because a lot of those conversations are focused around AI and what the new platforms are, and it just very much feels like how it felt when the smart phone dropped.

Teja (00:44:32):

Mmm <affirmative>. That’s cool. Yeah, totally. And I feel like, from a business standpoint, there’s like, in markets where there’s a lot of transition, uncertainty, and opacity, there’s a lot of opportunity for competitive advantage, and margin, and stuff like that, so it’s cool. It’s cool, ’cause I feel like, you know, working like, lower on the idea stack, like, around implementation, it’s like, very cut and dry. It’s like, this engineer costs this much, you know, versus working higher in the product and idea stack, you get to deal with like, what this is doing for your business, you know?

Andrew (00:45:08):

Totally. That’s a great point. I mean, the hardest part about being the implementers, is you’re at the end of the line, and all the strategic decisions happen way above you. And it’s fun to be involved in the strategy. You know, we wanna be involved in how do we make the business work, not just how do we build the thing you told us to build. The engagements where they just give us plans and tell us to build them, you know, we do that, but it’s not very collaborative. It’s more like, “Hey, you think you know what you’re doing, and we’re just gonna implement it.” The engagements where they’re like, “Here’s what we’re trying to figure out, and we’re hoping technology can do it,” and we get to be a part of those conversations. Those are fun. Those are rewarding, and I think the product ends up <unintelligible>.

Teja (00:45:54):

Yeah. So you and your brother both went to law school?

Andrew (00:45:59):

Yeah. And my other brother, too.

Teja (00:46:01):

And were your parents lawyers, or are they lawyers?

Andrew (00:46:04):

My dad. My dad’s a lawyer.

Teja (00:46:05):

Was that like, a big influence, basically, or…?

Andrew (00:46:09):

Yeah, it was. I didn’t know if I wanted to be a lawyer or not, but I saw what, you know, two of my brothers were doing, and I knew it was a good path there, and I figured, you know, why not? It’s funny, it’s like, you know, sometimes you don’t actually make a big decision. You make a small decision that like, leads to a big decision. (Teja: Yes.) The only decision I ever made was to take the LSAT. (Teja: <Laugh>.) I never decided to go to law school. I was like, “Fine, I’ll take the test. Let’s just see how I do.” (Teja: Yeah.) The LSAT is basically a giant budget game. (Teja: Yes.)

Andrew (00:46:44):

It’s fun. (Teja: Yes, yes.) So like, I got really obsessed with the LSAT and like, the, there was actually a logic game session. It’s terrifying. I’ll give you this thing where it’s like, “Okay, you’re transporting animals across the river, and there’s 42 animals,” and, you know, they give you these rules like, “Can’t put, you know, meat eaters with herbivores. You can have males and women together, but only if there’s more women than men.” They give you 10 other things, and then they’re like, “You have five minutes to figure this out, and if you make one mistake, then the whole thing falls apart.” But I kinda obsessed with that, and I would just practice them over and over, and I got a perfect score on the logic games part of the test, and…

Teja (00:47:28):

No shit.

Andrew (00:47:29):

Yeah. And it was awesome. You know, I was like, an average student, above average, and a low 3.0 GPA, but like, it’s totally unfair. And I think they’re changing this. I think they’re making it optional, but if you get in the 98th percentile in the LSAT, all the top schools are like, “Come on in!” They don’t care about anything else. (Teja: Totally.) It’s amazing. So I did well on the LSAT, and then it was like, well, now you have to go.

Teja (00:47:55):

That’s sick.

Andrew (00:47:57):

Law school is a great way of teaching you how to problem solve. That’s really what the core skill is there. And it also like, it removes that fear of reading a contract. (Teja: Yes.) And then lastly and most importantly, maybe, it teaches you to like, have a liability sensor, where you’re like, “<Alarm vocalizations>. Oh my god, I’m liable here. Get off the roof,” you know, whatever.

Teja (00:48:23):

That’s cool. I’ll tell you a story. So when I was in undergrad, like, basically a friend of mine, who’s like a big brother to me, he went to law school. He’s a really smart fucking guy. He went to Columbia Law and like, Cornell undergrad, and, you know, was like, this sharpe, like, little bit older, Indian guy that like, I’m an only child, so he was almost like an older brother. And (Andrew: Cool.) I remember when I was in undergrad, I was like, a liberal arts major, and he was like, “Dude, what the fuck are you gonna do with a liberal arts degree?” I was like, “I don’t know. I didn’t think that far.” And seriously, I was like, I like reading, and I like, you know, learning about philosophy, and it’s fun, and like, college was cheap, and so I wasn’t too worried about it. And so he’s like, “Dude, you need to like, go to grad school. Like, you can just go to law school,” and I was like, “Okay.” And so, it’s similar. I took the LSAT and there’s a lot of stuff involved in applying to law school, and so I remember I wanted to go to China, and I  studied Chinese and all this stuff, and I went there. Yeah, it was sweet. I ended up working for a startup, and this startup was basically started by a couple like, JD/MBAs from like, Northwestern, who were former consultants and like, went to China to kinda build some tech business. 

Teja (00:49:50):

And they were like, “We need a guy to help us build basically like, a data batch and like, help us do random shit for our company that we’re trying to build here.” And I was like, “Okay,” and they paid me pretty good money in China, (Andrew: Nice.) and so I had never anticipated working at a tech company or anything like that. And they sold that company pretty quickly in like, two years. (Andrew: Wow.) And it was sweet, but the way they did that is like, they would buy companies in local markets, and so they would just have me structure term sheets and like, you know, go and work with our, basically, our general counsel to do the deal. And when they sold the company, they had me like, do a bunch of work with the law firm that we had used, and I remember  talking to like, the lawyers that were like, helping us sell the company to the buyer. And I was like, maybe 22 or 23 at the time, and the lawyers were like, 30, and so they were, you know, peak lawyers, right, and like, working at a nice firm, making the money, and I would talk to them like, “What’s your lifestyle like? ‘Cause like, this is something that I have, at least, done one step towards.” And they’re like, “Dude, I’ve been trying to get out of law,” and I was like, “I see. Maybe I don’t want to do that.” (Andrew: Yeah.) And so that’s where my law school dreams kinda died. I was like…<laugh>.

Andrew (00:51:17):

I had a similar experience. I was in New York, doing the summer associate thing, and one of the big law firms, (Teja: Yeah.) and they were like, so great. ‘Cause you like, you go to work, and at five o’clock, they’d be like, “We’re taking you out to dinner, and then we’re taking you to like, a bar,” and it was so fun. And I remember like, one of the first nights there, we were out partying ‘til like, two in the morning, and I was like, “I have to go to the office and get my laptop,” and I remember like, going into the office and so many people were working. I was like, “Oh, shit. This is actually not a lifestyle business. This is a “everyone’s working at 2 a.m.” business.

Teja (00:51:52):

Everybody’s working at 2 a.m., and what killed me is like, they’re wearing fucking suits, and that sucked the most, because when I was working at the startup, my favorite thing is like, people rolled up in shorts and in a t-shirt, and like, it was all performance-based. You were smart, you worked hard, that’s all that mattered. But like, when we would be doing these video calls with these lawyers, they’re like, in fucking suits at like, 8:30 p.m. I’m like, “Guys. That’s so dumb,” and they’re like, “Yeah, well, we have to do that.” (Andrew: Yeah.) And I was like, “I can’t,” and that’s so childish, but I don’t know. It’s hard for me, honestly.

Andrew (00:52:32):

Well I remember when we were raising money, my co-founder was like, “Should I put on a nice shirt for this?” And I was like, “You can put on a nice shirt if you want, but if you don’t, you have to act really smart, ‘cause if you’re gonna do the t-shirt thing, you’ve gotta be brilliant.” And he goes, “I’m gonna put on a nice shirt.” <Laugh>.

Teja (00:52:56):

<Laugh>. That’s funny. So, you know Peter Thiel? (Andrew: Not personally.) In Zero to One, yeah, I think in one of his books, me neither, but it one of his books, he talks about like, how wearing like, a suit is actually like, it’s a negative signal, because that means the founders are like, optimizing to look like, presentable, (Andrew: Yeah.) whereas like, they should be like, they should be working so hard that they look fucking disheveled, you know? (Andrew: Yeah.) So like, that, it’s just funny. I don’t know how true that is. Our venture fund wears nice clothes, and I try to respect them by wearing nice clothes when they’re in town, and we’re having our board meeting. but like, yeah. Most of the time.

Andrew (00:53:30):

So, if you’re asking for money, wear nice clothes. (Teja: <Laugh>. Yeah.) It’s like, polite. You’re asking for money. Come on.

Teja (00:53:37):

That’s fair, yeah. I’m pretty sure I wore a t-shirt and stuff to our pitch. I wore a long sleeve t-shirt.

Andrew (00:53:45):

Strategically? ‘Cause you were trying be like, (Teja: Yeah <laugh>.) “I’m disheveled. I work so hard.”

Teja (00:54:02):

No, I am actually disheveled. I don’t know if I work hard, but I’m disheveled, though <laugh>. So after the summer associateship for two years, you’re like, “Fuck this. I wanna do my own thing,” basically?

Andrew (00:54:05):

Yeah, went back to law school, and then I was like, “Okay, I’m in law school…” this is gonna sound bad, but like, in grad schools, you can kind of slope by (Teja: Yeah.) and do fine. Like, they don’t want their students to look like, to do poorly, because it’s in all the rankings. Maybe it’s changed now, but back then, it was like, our average GPA is really high, so you can float, if you want. And so I knew that. I was like, “Okay, I actually have this great opportunity to work on this business while I’m still in law school, do enough to get by in law school and explore this thing. If it works well, I got a year, right? If it works well, then I can do that full time when I graduate. If it doesn’t work well, then I have my fallback plan.”

Andrew (00:54:50):

So that’s what I did. I started a business, and I had some good mentors. My brother, Eric, he mentored me a ton, joined as an advisor and founder. He had another co-founder of his business, a guy named <unintelligible>, who was a brilliant product strategy idea person, and he is also a musician, and he is actually the one that had the idea for Wikipedia for music, and so he kinda took me under his wing and started showing me how to explore, and we just started casting, building. And at the time, I was in LA, but we had an office in Palo Alto, and I was commuting to law school, basically. I was flying down Tuesday morning to my classes Tuesday, Wednesday, Thursday, flying back up, and then working Thursday, Friday, Saturday, Sunday.

Teja (00:55:37):

Yeah. I guess the hard part is like, getting in, and then once you’re in, they’re like, pass/fail, and just like, show up and do anything.

Andrew (00:55:46):

For sure. Really hard to get in. Once you’re in, I mean, if you wanna, if you’re like, trying to build a career out of it, you wanna be in the top percent. You wanna get a job at good firms, you wanna be in the top 10% or whatever, but like, me, I didn’t really know what I wanted to do. So I was just putting my eggs in two baskets instead of one.

Teja (00:56:08):

I’ll say, experience after raising money, what’s really intellectually gratifying for me, is I feel like the problems are more complex, and also the people that you can afford to hire are like, way more sophisticated. And in terms of just their experience level and like, the type conversations you’re having at work, are just like, they’re more gratifying, intellectually, (Andrew: Yeah.) and that is one thing where I feel like, you know, career in law or going to law school, like, you would for sure have that. Like, you would for sure feel intellectually challenged every day, you know?

Andrew (00:56:37):

Yeah. Working with super smart, motivating people who have worked their buts off, that is really rewarding.

Teja (00:56:39):

Yeah, yeah. And I feel like, so, it’s funny, like, the partner on our board from the fund that we work with, he, like, he’s probably one of the smartest dudes that I’ve met, and you have to like, come correct with him. And like, sometimes, if you’re like, smarter than average, you can get away with some bullshit, where you’re like, this is not totally logical, but I’m persuasive enough to just make this claim, and nobody’s gonna check me on it, but like, with him, you have to like, have a very tight argument, and you have to prep if you want to say something controversial, and like, that’s, for a guy like me, I enjoy that. You know, ‘cause, I feel like, as a founder, you’re doing a bunch of shit like tedium all the time, you know, so when you can do something that’s very intellectually challenging, it feels fucking cool, feels great, you know?

Andrew (00:57:51):

Yeah. And my brother is like that, too. And it’s a great skill to try to learn and then try to have people on your team do, as well. I mean, I’ve heard about (Teja: Yes.) decision fatigue, right? People come to you and say, “What should I do here?” and you tell ’em what to do, and the next person, “What should I do?” You tell ’em what to do. You’re just making tiny decisions all day, and then you get really fatigued. If, instead, they come to you and say, “Here’s a problem. Here’s option A, and here’s the drawbacks to that, and here’s the benefits, and here’s option B. I think we should do option B. What do you think?” They’ve done a lot of the thinking, and that empowers them, and then you have more mental space to do other types of thinking. Like, you don’t wanna solve everyone’s problem. (Teja: Yes.) You want people to solve problems, and you solve all their problems.

Teja (00:58:37):

Yes. That’s so true. You ever listen to or read a book by Jocko Willink? Do you know who that is? 

Andrew (00:58:44):

No. Great name, though.

Teja (00:58:48):

It’s a fucking sick name. Yeah, Jocko. Yeah. His real name is John, I think. But he’s a former Navy SEAL and you know, big guy in the jiu jitsu martial arts community, and he wrote a book called Extreme Ownership, basically sort of talking about lessons he learned on the SEAL teams podcast called The Jocko Podcast, and it’s a really cool podcast on leadership, on jiu jitsu, on martial arts, on different things like that. So if you like lessons taught to you, like, through anime, I think you’d dig this podcast, ‘cause it’s almost like, he’s been in real life battle and like, forged his understanding of human behavior from that. It’s really cool.

Andrew (00:59:38):

I’ll definitely check it out, ‘cause the one thing I really need right now is another podcast recommendation. (Teja: <Laugh>.) It’s like, I actually will check it out, and I love podcasts, but Jesus, there’s so many, and they’re so good, and it’s like, how can you possibly…? And they come out like, every week, sometimes more. It’s really, it’s hard to keep up.

Teja (01:00:01):

Do you feel like, pressure to consume information?

Andrew (01:00:06):

Uh-huh <affirmative>. It’s not that I feel pressured to consume information, I feel like I consume information too much, as a form of escaping, escapism. You know, I wanna sell every moment I have, so it’s like, oh, okay, I’m gonna, you know, I’m gonna do some laundry and put on a podcast. I’m gonna watch dishes and put on a podcast. I’m gonna walk my dog, and put on podcast. I’m gonna get in the car, and put on an audiobook, whatever. And I realized, I’m not creating enough time to just sit with thoughts and let them work through, and so like, now I do my morning commute, and I intentionally don’t listen to anything. Just let the mind wander. And same when I run; I just run with music. I just let it wander, and I realize like, from my mind, it’s very, you know, intertangled with thoughts, and I need to like, let those things work out, work themselves out. And if I don’t do that, then it’s, yeah, it’s just hard for me. So I’m trying to be aware and mindful about not just filling up time with podcasts, even when it’s uncomfortable.

Teja (01:01:16):

I try not to have any information like, input, other than like, work and like, jiu jitsu, and like, people that I care about until like, Saturday, and then I may, you know, when I clean my house or when I’m like, gardening, or you know, on a road trip, then I’ll be like, okay, it’s time to like, get a sense of what’s going on in the world, and I’ll just use that timebox to rotate through a couple things that I like.

Andrew (01:01:45):

So you’re not a sports fan, then.

Teja (01:01:49):

I like mixed martial arts and like, martial arts-related sports, but like…

Andrew (01:01:52):

Which happens on Saturday, conveniently.

Teja (01:01:56):

Yes, exactly, but I don’t watch any other sports, generally, personally.

Andrew (01:02:02):

I think that’s the trap that lures me into the news cycles. I wanna see like, what’s happening in the basketball world. I tried to, actually like, consciously quit baseball a long time ago. I’m like, I don’t have time for these 152 games, and you know, I have a fantasy football league, which I basically use to keep in touch with friends, and so I pay attention to that.

Teja (01:02:23):

Like, why is it so like, addictive? I don’t know. I can get addicted to watching like, commentators commentate about MMA fights. Like, I’ll watch their analysis about a fight, and I’m like, hooked, you know? I don’t know why.

Andrew (01:02:38):

Yeah. It’s just that like, the deeper you get into something, the more interesting it’s to you, and then you wanna get deeper, and it’s a vicious cycle.

Teja (01:02:56):

Yeah, you know like, “Oh yeah, like, this guy’s got a great take-down defense,” like, “Oh, but this guy’s like, a little bit bigger, and he’s got good striking. Who’s gonna win?” You know, like, I’m just gonna watch the fight. Why do I care about these people’s opinions about what’s gonna happen or what happened after one person won? 

Andrew (01:03:03):

I’m super annoying. I’ll like, rewind a preseason game, ‘cause I didn’t hear what someone said. Like, “Oh, I gotta listen to that again.” What? It’s a preseason game. Who cares? Yeah, it’s gone too far. 

Teja (01:03:14):

Yeah. Do you feel like, sometimes when you consume that stuff, it helps you get your mind off of work? Like, it’s like a nice way to zone into something else?

Andrew (01:03:25):

Yes. It’s totally another escapism. Thinking about that a lot lately. Like, when and why we choose to escape from our stuff, and why we choose to commit and just deal with it. But like, I love basketball, because I only think about basketball when I’m playing basketball. No other thoughts come to my mind, and that kinda mental focus and purity is such an incredible feeling.

Teja (01:03:53):

Yeah. No, I hear you. I feel the same way. I feel like sometimes like, it’s nice to think about low-stakes things. Like, it’s nice to think about what happens when these two people fight? It’s pretty low-stakes, in terms of my life. (Andrew: Yeah.) Like, nothing is…right, it’s just a sport. (Andrew: Yeah.) But, if you’re thinking about work, you’re like, “If I make the wrong decision here, it’s bad. It’s like, not good.” So, <laugh>.

Andrew (01:04:17):

That’s true. And it can help you focus in those big, high-stakes moments, if you do low-stake stuff as a prize. Like, golf is the perfect example of this. I’m a new golfer, pandemic golfer. I like to not understand why I do it, because it’s so stupid. I’m just gonna hit a ball around a fake grassy field, (Teja: <Laugh>.) but at the same time, it’s so like, if you make it important so hard, you have to focus so much, and it’s that exact thing. It’s low-stakes, but very hard. And if you can learn to focus and perform at that level, you can learn the patience that comes with it, then I think it makes you better at your high-stakes focus moments.

Teja (01:04:58):

Totally. There’s a book that I read this past weekend called Dokkōdō. It’s written by this dude, Miyamoto Musashi, who’s like, history’s greatest swordsman.

Andrew (01:05:05):

I’m reading one of his books. I’m reading Musashi right now.

Teja (01:05:09):

Okay, nice. Yeah, that’s a great one. And then he wrote a book called The Book of Five Rings, as well, which is also really good, and it’s, yeah.

Andrew (01:05:18):

My list just gets longer and longer.

Teja (01:05:20):

Yeah. Musashi, then Book of Five Rings, then Dokkōdō. And Dokkōdō was the last book he wrote, like, a week before he died, (Andrew: Oh, wow.) and it like, 21 precepts to like, basically, be a fucking samurai. It teaches you how to be a like, a steadfast person, and I feel like they come at it differently than the stoics do, because a lot of the stoic thinkers were like, born into wealth. Like, Marcus Aurelius, the dude was born an emperor. So you’re just like, okay dude, you’re emperor. Like yeah, maybe you fought first in some battles, but like, your dad was a fucking emperor. Like, that’s not that cool, whereas like, Musashi is like, he built his way up through battle to being history’s greatest swordsman. So, I admire that.

Andrew (01:06:02):

Yeah. And there’s a thousand Musashi’s [who] have tried that and died, so that’s like amazing that he made it.

Teja (01:06:09):

Yeah, totally. And so,he talks about it in, you know, the Book of Five Rings and also in Dokkōdō like, having indifference and like, having an unflappable sort of emotional state and like, not actually taking decisions seriously, actually makes you better at your craft. And I see that sometimes with like, really good competitors in jiu jitsu, they’re able to like, take a fucking nap before competing. (Andrew: Yeah.) Like, their resting heart rate is that low, you know, (Andrew: Yeah.) where they’re just like, they’re in their 40s and 50s, and they’re napping. They’re not nervous, and then they turn it on when they’re ready to compete, and then they get back to that state of rest, verses like, they’re amped the whole time, which is sometimes what it feels like, if you’re in a state of stress for 12 hours for work.

Andrew (01:06:58):

Yeah, Steph Curry, his trainer, they work on that. They talk about how he goes to the bench, and he does these exercises, where he lowers his heart rate just with [his] mind while he’s on the bench.

Teja (01:07:10):

That’s powerful. Apparently, that’s like, if you can get your resting heart rate as low as possible, that is connected to faster recovery after intense bouts of effort. And so like, it creates like, a nice ramp down, and then over intensity bursts, you can maintain that same intensity in successive loops for a longer period. So, you know. Yeah. From Musashi to Steph Curry.

Andrew (01:07:48):

Great, you know? They all have something in common. (Teja: Yeah.) And it’s the way of the sword, right? It’s all about your mind. It’s not about (Teja: Yeah.) the physical stuff.

Teja (01:07:55):

Yeah. What do you think about Musashi so far? How far along are you in that book?

Andrew (01:08:00):

I’m like, 25% of the way through. So like, 200 pages in. It’s a pretty long book. (Teja: <Laugh>. Yeah.) I think it’s great. You know, sometimes I worry about really old books, ‘cause it’s a different world, it can feel out of touch, but the samurai said he wanted [it] to feel like an old world, and it’s written in a funny way, in a way. Like, there’s a good level of humor to how it all is. I guess it reflects his state of not taking anything too seriously, even in a life and death battle. But it’s great. No, I was comparing it to Shogun when I started reading it, and Shogun is much more like Game of Thrones, like where you have (Teja: Mm-hmm <affirmative>.) these like, these leaders that are fighting and deploying strategies, and it’s very high level, and Musashi‘s kinda like, the opposite. It’s like, each person’s individual story, and how they kinda interconnect from the lower level. So I dig it. I really enjoy it.

Teja (01:09:02):

That’s awesome. Have you seen the Akira Kurosawa movie, Seven Samurai? (Andrew: A long time ago.) It’s a classic, if you like samurai flicks. There’s an anime called Seven Samurai that’s based on that story that’s pretty good. I watched it like, maybe 15 years ago, but it’s pretty good. Alright, man, we’ve been going for like, over an hour, so…

Andrew (01:09:28):

Yeah, yeah.

Teja (01:09:32):

<Laugh>. Hell yeah. Let’s do it again. I feel like there’s so much to talk about.

Andrew (01:09:36):

I agree. Let me know if you come to San Francisco,

Teja (01:09:40):

Okay, yeah. And let me know if you guys come to Nashville, or close by, you know? I’ll show you guys some spots, and we can grab a beer or something like that. Did you think that you’d be in this field like, 15 years ago? Like, did you think this was where you’d be spending your life’s gifts on?

Andrew (01:10:00):

I think I wanted to build stuff. I think the only thing that sometimes feels not as, I don’t know, ideal these days, is that like, I wanna have more ownership in the stuff we’re building. Like, so I feel that way with the company, right? Like, I feel like I have ownership in building that company. But, you know, like, we work with really cool teams building really cool products, and there’s like, a little bit of a wistfulness of like, “Wow, but wouldn’t that be cool if your whole life is just really trying to fix this complicated problem?” And so that’s the one thing where I’m like, maybe you know, my next thing, whenever that is, maybe it’s with this team, you know, I wanna just be like, “Let’s work on a problem.”

Teja (01:10:49):

I don’t know. It’s cool to work on like, a bunch of different problems, though, you know? But I can understand like, the desire to like, have like, a thing that you’re like, we wanna be the best at this, in the world, you know?

Andrew (01:11:03):

Yeah. It’s cyclical. I mean, I’ve been doing this for 12 years, I absolutely love it.

Teja (01:11:11):

It’s probably natural you do something for like, over a decade, and you’re always like, “Oh, I wonder what the opposite of this is like?” You know <laugh>?

Andrew (01:11:18):

Yeah, exactly. What would it be like, if I was a professional jiu jitsu?

Teja (01:11:26):

Totally. Totally. And then I’d probably hate it, ‘cause I’m like, “Dude, I have to take training so seriously.”

Andrew (01:11:32):

I know that’s the risk, you know?

Teja (01:11:35):

Yeah.

Andrew (01:11:37):

You walk away amazing things, and you’re like, “What have I done?”

Teja (01:11:50):

Oh like, my post-workout beverage is a beer, every time I train. And so like, I definitely would not be doing that, if I like, had to be a professional jiu jitsu competitor.

Andrew (01:11:56):

Don’t you train at 6:00 a.m., though?

Teja (01:11:59):

Not often. (Andrew: <Laugh>.) If it’s at 6:00 a.m., then it’s like, you know, I’m probably not, yeah. I may have fibbed there. If it’s at 6:00 a.m., unfortunately, probably, taking some nicotine. I’m, yeah. I’m having some coffee, but if it’s at like, so if it’s at 6:00 p.m., like, I’m stopping by Whole Foods, I’m getting like, a hard kombucha, plus like, a pre-made…after 6:00 p.m., if I go to Whole Foods, I get like, a hard kombucha, you know, not so like, you know, 2, 3% max, plus like, a pre-made sushi thing, maybe two. Yeah, and I’ll slam that, you know what I mean? And then, maybe have a whiskey afterwards, but like, that’s my go-to after night. (Andrew: That’s healthy.) And on Saturdays, if I’m training in the day, I’ll probably have a beer, ‘cause, you know, you finish at like, 1:00 p.m. (THE FRONTIER THEME FADES IN)

Andrew (01:12:49):

It’s one like, life’s great joys, you know? We all need balance. But man, there’s nothing like a beer after a workout.

Teja (01:12:55):

It’s the best. It’s so good. Especially like, outside, when you’re like, you’re done with your workout, you’re having your beer out in your yard, and like, you’re doing some shit outside. Gardening. (Andrew: Yeah.) That’s the best. Yeah.

Faith, via previous recording (01:13:09):

Thanks for listening to The Frontier Podcast, powered by Gun.io. We drop two episodes per week, so if you like this episode, be sure to subscribe on your platform of choice, and come hang out with us again next week, and bring all your internet friends. If you have questions or recommendations, just shoot us a Twitter DM @theFrontierPod, and we’ll see you next week.

(THE FRONTIER THEME ENDS)