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Speaker 1: Hi guys, it's your friend Kate Max and welcome back

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Speaker 1: to Post run High. We talk a lot about building

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Speaker 1: wealth and success, but not enough about what to actually

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Speaker 1: do once you have it. Today's guest has built and

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Speaker 1: sold a massive company, made real money, and then had

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Speaker 1: to figure out what comes next. Today's episode is with

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Speaker 1: encoren Adpaul. He's the founder of Teachable and someone my

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Speaker 1: husband Jeremy and I have known for a bit now

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Speaker 1: here in New York. The two of them play put

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Speaker 1: all together, and I've always had such great interactions with Encore,

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Speaker 1: so it was really fun to finally get a run

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Speaker 1: in together and then sit down to chat after Encore

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Speaker 1: grew up in Oman with Indian roots and came to

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Speaker 1: the US to study economics at UC Berkeley. While he

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Speaker 1: was there, he started building Facebook apps, yes, the kind

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Speaker 1: that tell you which friends character you are most like,

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Speaker 1: and before he knew it, those apps were making him

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Speaker 1: real money. That early entrepreneurial spark eventually led him to

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Speaker 1: found Teachable at just twenty four years old, which he

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Speaker 1: went on to sell for about two hundred and fifty

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Speaker 1: million dollars by the time he was thirty one. Since then,

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Speaker 1: Encore has seen every side of the founder journey, from

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Speaker 1: scrappy student projects to major exits investing, and now continuing

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Speaker 1: to build new businesses. But what I loved most about

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Speaker 1: this conversation isn't just Encore success. It's about how open

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Speaker 1: and transparent he is, about the mindset behind it all.

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Speaker 1: We talked about how his definition of success has evolved,

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Speaker 1: what freedom really looks like, and what his life is

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Speaker 1: like outside of work. I was also pleasantly surprised to

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Speaker 1: find out that he is quite the athlete himself, which

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Speaker 1: I semi knew from his pidel skills, but we dive

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Speaker 1: into that a bit at the start of our conversation.

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Speaker 1: All right, let's get into it. This is Encore on

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Speaker 1: Post Run High. Encore, welcome to Post Run High.

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Speaker 2: Thank you. Excited to be here, even though I had

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Speaker 2: to run to get here.

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Speaker 1: We ran a couple of blocks, and by that.

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Speaker 2: You mean we ran twenty miles. Good pace, kept it going,

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Speaker 2: kept the conversation going. It was good. It was good.

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Speaker 2: I haven't been running a lot lately. I am supposed

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Speaker 2: on a marathon later this year, so maybe this was

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Speaker 2: my training run number one.

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Speaker 1: Oh well, what's the farthest distance you've ever Ran.

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Speaker 2: I did the Brooklyn Half two years ago.

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Speaker 1: Okay, so you have never done a full marathon.

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Speaker 2: Now iver done a full marathon. The Brooklyn Half I

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Speaker 2: got into because I'm a very competitive person and we

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Speaker 2: had a group chat with eight people, and all I

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Speaker 2: cared about was beating the other seven. You know, the

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Speaker 2: time didn't matter, did you I did? I did? I

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Speaker 2: barely edged it out. Because people always say running is

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Speaker 2: an individual sport. It doesn't matter how you do, it's

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Speaker 2: just about yourself. I didn't care about myself. I just

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Speaker 2: wanted to beat the others.

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Speaker 1: What marathon are you doing Berlin?

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Speaker 2: Wow?

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Speaker 1: Jeremy's friends doing Berlin too?

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Speaker 2: October thirtieth, September twenty second, something like that. Oh okay, yeah,

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Speaker 2: that should be fun. The big reason I'm doing it

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Speaker 2: is I've been prioritizing spending time with family a lot,

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Speaker 2: and my brother's really gotten into run, so it's a

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Speaker 2: little brother activity. So as a result I have to

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Speaker 2: actually do it.

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Speaker 1: Well, that's going to be so fun. Are you guys

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Speaker 1: going to do October fast after? No?

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Speaker 2: I have a team retreat right before, so Lisbon then

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Speaker 2: straight to Berlin. But yeah, I'm looking forward.

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Speaker 1: Okay, what's your training looking like Recently?

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Speaker 2: I keep myself pretty active, but most of it is

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Speaker 2: either playing sports or working out. Running is something that

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Speaker 2: as I get closer, I'll probably do one long run

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Speaker 2: a week or something, because again, it's not the primary

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Speaker 2: thing I'm optimizing for. My goal is, I don't know,

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Speaker 2: trying to do it in four hours and not die.

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Speaker 1: The first time I did the New York City Marathon,

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Speaker 1: I ran it like right under four hours, and that

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Speaker 1: was my goal too, and I literally was doing no training,

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Speaker 1: Like I mean, I did a little bit of training,

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Speaker 1: but I was in college. I was a sophomore. I

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Speaker 1: was drinking going out.

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Speaker 2: In that What was the longest run you had done

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Speaker 2: prior to that.

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Speaker 1: It's funny because whenever you run a marathon, people will

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Speaker 1: say to you, training wise, you should get to like

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Speaker 1: a twenty or twenty two mile run. And I think

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Speaker 1: the farthest I had gone was like sixteen miles, and

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Speaker 1: I was like, oh, I'll be fine. And then the

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Speaker 1: first time I did the New York City Marathon, I

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Speaker 1: got to mile eighty, which is when you get into

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Speaker 1: the Bronx, and it was like raining that year, and

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Speaker 1: my legs were so fried to the point where I

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Speaker 1: had to stop, like I completely hit the wall. And

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Speaker 1: I had brought like an extra pair of socks for

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Speaker 1: some reason, and I was like this woman in the

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Speaker 1: Bronx helped me change my socks on the sideline, and

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Speaker 1: oh so.

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Speaker 2: That's a beautiful New York story.

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Speaker 1: Though beautiful New York story, I can tell you that

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Speaker 1: it was horrible. But I did still finish in under

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Speaker 1: four hours, and that was impressive. But I remember, my

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Speaker 1: older brother has a video of me running at mile

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Speaker 1: twenty four, and if you guys know the New York

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Speaker 1: City Marathon, you know exactly where mile twenty four is

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Speaker 1: in Central Park. And he posted it on his story

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Speaker 1: and I literally looked like I was walking, but in

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Speaker 1: my mind I was running, And I was like, Connor,

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Speaker 1: why would you post that? But you know what, still

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Speaker 1: did it.

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Speaker 2: I hope there's an old German Man waiting for me

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Speaker 2: in mile twenty two with some socks.

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Speaker 1: Yeah. Yeah, you're a padel guy. But on our run,

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Speaker 1: you were talking a little bit about cricket. So let's

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Speaker 1: talk about movement and how it looks in your life.

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Speaker 2: Yeah, so now a lot of peop people know about

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Speaker 2: you know, all the work I do in tech. But

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Speaker 2: until age fourteen fifteen, my goal was to be a

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Speaker 2: professional cricketer. Like I spent pretty much every day from

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Speaker 2: age like five, six seven till fourteen fifteen thinking my

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Speaker 2: dream was to play cricket for a living. Wow, And

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Speaker 2: I got relatively far. I played internationally for the country

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Speaker 2: I grew up in, so I played for Oman at

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Speaker 2: the under seventeen Asian level. But cricket and Oman is

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Speaker 2: like cricket in America. You're very good in a small country,

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Speaker 2: and when we went to play against better kids in India,

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Speaker 2: were like, you're good, but not good enough to do

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Speaker 2: this for a living. But as a result, being competitive

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Speaker 2: physical movement has been such a big part of who

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Speaker 2: I am, and even now I feel like just playing

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Speaker 2: team sport is something that has shaped me quite a bit.

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Speaker 1: Yeah, And I feel like when you grow up playing

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Speaker 1: team sports, it's so fun to like continue on in

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Speaker 1: your adult life being competitive and I like knowing that

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Speaker 1: you've picked up at all. But for people that don't know,

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Speaker 1: let's talk a little bit about cricket for a second.

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Speaker 1: Because I feel like I grew up I would be

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Speaker 1: at lacrosse tourns and I'm going to say, like kind

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Speaker 1: of over in like a baseball diamond type of setting.

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Speaker 1: I would occasionally see people playing.

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Speaker 2: Cricket, people in the white and I.

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Speaker 1: Never knew like what cricket was. I knew it was

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Speaker 1: similar to baseball, right yep, But like explain.

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Speaker 2: Cricket to absolutely so think about it as a baseball

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Speaker 2: with two bases. People have this vision of like, oh,

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Speaker 2: cricket is played by old British men and wearing all whites,

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Speaker 2: and the games go on for five days. And while

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Speaker 2: that is the genesis of where the sport came from,

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Speaker 2: today's version is three or four hours, super quick, very competitive,

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Speaker 2: there's two bases. But at the same time I find

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Speaker 2: what I find powerful about it is that the team sport.

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Speaker 2: But at the same time it can be incredibly isolating.

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Speaker 2: When you're batting, you have eleven people around you cursing you,

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Speaker 2: yelling at you, calling your mom all kinds of names.

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Speaker 2: But as a result, it builds this mental resilience. You

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Speaker 2: have a person coming towards you hurling a fithysical object

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Speaker 2: which if it hits you can kill you. Right you

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Speaker 2: have protective gear. So it's this very physical, very mental

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Speaker 2: sport that played such a big part in my life

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Speaker 2: and if you move outside the US, it is actually

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Speaker 2: the second most followed sport in the world after soccer.

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Speaker 1: Oh wow, I did not know that.

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Speaker 2: It is insane. A big part of it is India, Pakistan,

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Speaker 2: Sri Lanka. These are big countries, but it is the

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Speaker 2: second most followed sport. Even when they held a game

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Speaker 2: in New York City last year they brought the World

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Speaker 2: Cup to the US, the cheapest tickets for games between

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Speaker 2: India and Pakistan in New York was fifteen hundred dollars,

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Speaker 2: which is pretty insane for a sport that's, you know,

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Speaker 2: completely Unamerican. It was almost as expensive to like watch

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Speaker 2: an NBA Finals as like a random cricket game in

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Speaker 2: New York.

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Speaker 1: And you are still a big cricket fan.

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Speaker 2: I'm a big cricket fan. Now it's more on watching

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Speaker 2: and I recently also decided to buy a stake in

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Speaker 2: a team, so it was like, I want to invest

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Speaker 2: in it. I haven't played as much since it's a

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Speaker 2: hard sport to play. You have to go up to

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Speaker 2: the Bronx, spend like a couple hours getting there, play

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Speaker 2: for eight hours, so it's a day.

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Speaker 1: Yeah. They play in Van Cortland Park.

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Speaker 2: They played Vancortland Park a game that before.

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Speaker 1: Because when I went to Fordham, when I was a

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Speaker 1: freshman and a little bit of my sophomore year, I

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Speaker 1: lived at the rose Hill campus, and I decided my

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Speaker 1: sophomore year, I was like, let me just switch things

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Speaker 1: up a little bit on campus here, and I tried

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Speaker 1: out for the cross country team, where I guess I

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Speaker 1: walked on technically didn't try out.

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Speaker 2: And yeah, this makes a marathon less impressive, but go on.

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Speaker 1: Yeah, we used to always see the guys playing cricket

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Speaker 1: at Van Cortland.

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Speaker 2: Yeah, it was such a big part of who I

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Speaker 2: am as a person and how I grew up. So

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Speaker 2: now deciding to buy a piece of a cricket team

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Speaker 2: was almost like me paying the eight year old version

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Speaker 2: of myself to kind of go back to what I

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Speaker 2: thought would be awesome as a kid. Yeah.

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Speaker 1: I mean, your younger self is probably like that's pretty bad.

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Speaker 2: Yeah exactly.

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Speaker 1: Okay, Well, let's talk a little bit more about your childhood.

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Speaker 1: So you were born in India, but you didn't spend

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Speaker 1: the majority of your life in India, right, So like

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Speaker 1: paint the picture for us of what your childhood was

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Speaker 1: like where you grew up.

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Speaker 2: And yeah, yeah, a little.

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Speaker 1: Bit about it.

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Speaker 2: So I grew up in Oman, in the Middle East

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Speaker 2: country that not a lot of people have heard of,

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Speaker 2: but it's a small country that also has a lot

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Speaker 2: of oil money. And my parents moved there in the

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Speaker 2: early eighties simply because the country discovered a lot of oil.

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Speaker 2: As Indian people, you would make twenty percent more money

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Speaker 2: by moving there, So they moved there. And honestly, I

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Speaker 2: spent the first seventeen years of my life there and

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Speaker 2: it was pretty ideal. My biggest regrets were it got

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Speaker 2: kind of boring by the time you get fifteen sixteen

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Speaker 2: and you're a little bit rebellious, you want to go out.

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Speaker 2: It's a pretty tame, quiet sort of place, so I

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Speaker 2: was itching to leave. But otherwise it was a very relaxed,

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Speaker 2: very sort of good childhood from what I can imagine.

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Speaker 1: And we kind of touched on this on our run.

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Speaker 1: But you grew up almost shaped by three different cultures, right,

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Speaker 1: because that's seventeen. You ended up moving to the US

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Speaker 1: for school, but you have a little bit of like

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Speaker 1: your Indian background and then growing up in Oman. How

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Speaker 1: does Oman differ from growing up in India, Like, is

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Speaker 1: it totally different?

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Speaker 2: Yeah, so Oman culturally so culturally, I mean we're Indian.

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Speaker 2: I'm I'm not a religious person, but born Hindu. Oman

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Speaker 2: is an Arab state. It's a Muslim country. Alcohol is

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Speaker 2: like somewhat prohibited. There's rules on what you can wear

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Speaker 2: and where you can go. Relative to the Middle East,

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Speaker 2: it's probably the most chill country, but it's still the

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Speaker 2: Middle East. So culturally, yes, we were from India, but

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Speaker 2: if I go back to India, I'd never quite fit

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Speaker 2: in there. Oman you're always a transient worker right at

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Speaker 2: the end of the day. We are expats. You have

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Speaker 2: no immigration status, no legal status. So while it's home

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Speaker 2: in a lot of ways, it's not home here. I

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Speaker 2: don't speak Arabic. I would imagine at this point, I've

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Speaker 2: been in the US a little bit over fifteen years.

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Speaker 2: America is probably my primary identity, but it's still very

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Speaker 2: different from someone born here or raised here. All of that.

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Speaker 1: Do you feel like there's certain attributes from your childhood

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Speaker 1: in India and Oman that have translated into your life

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Speaker 1: here in the US.

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Speaker 2: I think I'm so much better in this country than

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Speaker 2: back home. Why as an example, I by the end

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Speaker 2: was pretty bad at school back there, because school was

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Speaker 2: very regimented. You had to like study really hard. You

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Speaker 2: couldn't work the system. There's a lot of math and

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Speaker 2: science and if you weren't willing to put in the hours,

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Speaker 2: you wouldn't do very well. I came to the US

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Speaker 2: and I realized college here is like one big game.

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Speaker 2: You can figure out which classes to take, which classes

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Speaker 2: to actually show up for, how to get credits in

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Speaker 2: random ways. And I think the US society that's.

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Speaker 1: Not making the US look great, Come on it.

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Speaker 2: Does it does? I think this is why you have

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Speaker 2: entrepreneurship here, like the fact that you can come here

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Speaker 2: and take initiative and that is rewarded. Initiative is not

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Speaker 2: rewarded anywhere else. As an example, when I was here

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Speaker 2: as in Silicon Valley studying at the University of California, Berkeley,

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Speaker 2: I started a business in college that was making at

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Speaker 2: first twenty dollars a day, then a few hundred dollars

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Speaker 2: a day. And I was amazed by how many really smart,

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Speaker 2: impressive people were willing to meet with me, talk with me,

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Speaker 2: give me feedback. When I tried that back home in India,

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Speaker 2: they don't take you seriously as an eighteen year old.

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Speaker 2: The US and especially Silicon Valley is one of the

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Speaker 2: few places in the world that will take you very

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Speaker 2: seriously as a sixteen, seventeen, eighteen, nineteen year old. And

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Speaker 2: I think that's what makes this country very, very like

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Speaker 2: the best place to start something.

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Speaker 1: Why do you think that doesn't exist as much in Oman.

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Speaker 2: I think it's less that it doesn't exist in Oman specifically,

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Speaker 2: VERSUS America is just that special. And the reason for that,

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Speaker 2: I believe is you have two hundred years of selection bias,

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Speaker 2: where for two hundred years, the people that weren't happy

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Speaker 2: with where they lived moved here. Now you multiply that

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Speaker 2: sort of risk taking across many, many generations, And what

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Speaker 2: I think makes this country super unique is for hundreds

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Speaker 2: of years, smart enterprising people from across the world, across

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Speaker 2: the discipline have moved here to start a life, and

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Speaker 2: that really compounds over period of time.

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Speaker 1: Yeah, it's incredible. When you were younger and you moved

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Speaker 1: here at seventeen, like, is that something that you knew

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Speaker 1: about the US that you were like, I want to

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Speaker 1: move to the US and go to college there because of.

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Speaker 2: This, I wasn't frankly thinking that far ahead. But my

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Speaker 2: dad always in you like from the I think he

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Speaker 2: read a lot when he was younger, and he was

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Speaker 2: like from the age meeting thirteen or fourteen, he said,

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Speaker 2: look like at some point if you take your SAT

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Speaker 2: said no idea, what the SATs even war? And he

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Speaker 2: he's like, you have to go to the US since

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Speaker 2: you know, if you are entrepreneurial, you want to start something,

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Speaker 2: you want to build something incredible, There's no better place

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Speaker 2: for it. But that is the power of the American

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Speaker 2: brand where you have someone an Indian man living in

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Speaker 2: Oman had been to the US once convinced that his

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Speaker 2: children should come study in the US. And that's pretty cool.

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Speaker 1: When you think about success in your childhood household, what

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Speaker 1: was the north star for you? And like, you know

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Speaker 1: what did your parents kind of instill in you guys?

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Speaker 2: Yeah, so growing up, my parents are pretty liberal for

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Speaker 2: Indian parents, standards were very like, you know, do what

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Speaker 2: makes you happy. But I think my dad was always

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Speaker 2: biased that both me and my brother go out and

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Speaker 2: start her own thing. And I think a lot of

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Speaker 2: that came from the fact that he wanted to do that,

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Speaker 2: but for whatever reason, it felt like it wasn't responsible

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Speaker 2: of him too. I mean we were fine, we were

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Speaker 2: middle class, you know, potentially even upper middle class, but

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Speaker 2: it still felt too high risk for him to give

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Speaker 2: up a stable job to go do something. So in return,

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Speaker 2: he's like, Okay, I'll work really hard, I'll do this,

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Speaker 2: but but you and your brother should go ahead, and

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Speaker 2: you know, if you ever feel like it, go chase

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Speaker 2: your dreams, start your own thing. Don't feel like you

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Speaker 2: have to take the safe path. Since I did that

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Speaker 2: for you.

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Speaker 1: I mean, your dad must be so proud of you

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Speaker 1: for what you've created before we get to everything that

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Speaker 1: you've built. Did your brother start his own company as well?

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Speaker 2: No, my brother has had a bunch of side hustles,

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Speaker 2: but right now he's also very happy making a completely

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Speaker 2: different choice, and you know, working at a good job.

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Speaker 2: And honestly, I think his life is less stressful than mine.

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Speaker 1: So and that's also really special because I know you

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Speaker 1: fly your parents in a decent bit right to the US,

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Speaker 1: and would you ever want them to move here? No?

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Speaker 2: Their social lives are so popping, they have such a

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Speaker 2: great life, Like why would they give up their like crazy? Heck,

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Speaker 2: take social life to move to a new country. At

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Speaker 2: this age.

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Speaker 1: Yeah.

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Speaker 2: Yeah, Like I look at all my friends in New York.

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Speaker 2: Their lives are crazier than ours, Like they have parties

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Speaker 2: every night, they're happy.

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Speaker 1: Well, what made you choose UC Berkeley.

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Speaker 2: I got rejected from every better school than UC Berkeley.

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Speaker 2: It was very simple. I think I overshot my college applications.

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Speaker 2: I got rejected from every IVY League school. I got

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Speaker 2: rejected from. Stanford Berkeley was the best school I got into.

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Speaker 2: So it was very simple. In the US, you have

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Speaker 2: the luxury of visiting all your colleges and seeing which

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Speaker 2: one you connect the most with. For me, for most

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Speaker 2: Indian kids, it's like, Okay, what is the best school

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Speaker 2: I get into? Sure, I'll go there. And the first

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Speaker 2: time you're on campus is your first day of class.

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Speaker 1: And you were seventeen, not eighteen, correct, So you were

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Speaker 1: a year younger than most of the kids.

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Speaker 2: You're younger. I graduated at twenty, so I graduated before

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Speaker 2: I could legally have a drink.

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Speaker 1: Well, UC Berkeley's a good place to land.

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Speaker 2: It was a good place to land. It was a

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Speaker 2: little bit different from what I was expecting. This sounds

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Speaker 2: really dumb and corny, but at the time, you know,

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Speaker 2: A big part of what you learn about America is

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Speaker 2: like movies and TV and stuff and as yeah, food

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Speaker 2: and as embarrassing as it sounds. I go to college

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Speaker 2: and in my mind, I'm like, Oh, this is going

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Speaker 2: to be like American Pie. This is going to be

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Speaker 2: like frat parties and red solo cups and just people

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Speaker 2: doing crazy things. But it was a pretty dorky engineering school.

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Speaker 2: Like the first day I get there, half our floor

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Speaker 2: is just playing video games, like no one wants to

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Speaker 2: socialize or doing their own thing, And I was like,

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Speaker 2: this is not the US college experience I was promised.

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Speaker 2: But being on the West Coast and stuff was pretty

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Speaker 2: helpful and it helped me meet a lot of great people.

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Speaker 1: During that transition process. When you first moved here, was

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Speaker 1: the transition hard? Did you feel like? You know? What

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Speaker 1: was that like? For you?

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Speaker 2: It was easier than you would imagine. And I think

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Speaker 2: there's a couple of reasons for that. I think one,

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Speaker 2: seventeen is early enough where your own identity is malleable,

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Speaker 2: you can change quite a bit. So a lot of

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Speaker 2: my friends who moved to the US at seventeen culturally

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Speaker 2: changed quite a bit. The ones who moved to twenty one, right,

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Speaker 2: four years. Those four years make a massive difference. The

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Speaker 2: second thing is the US is relatively easy to move

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Speaker 2: to compared to most of the world. I had a

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Speaker 2: hot take that I got canceled for online for saying

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Speaker 2: where I said America was the least racist country in

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Speaker 2: the world. And I genuinely like two years before that,

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Speaker 2: I'd studied in an all boys school in Australia and

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Speaker 2: that was a truly hard experience of trying to adjust

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Speaker 2: assimilate going to like a US college campus. I think

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Speaker 2: it's one of the friendliest places you can go, no

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Speaker 2: matter where you're from.

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Speaker 1: What would your advice be for other students like you

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Speaker 1: transitioning into a school in the US and kind of

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Speaker 1: being in the US almost for the first time.

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Speaker 2: The mistake I see a lot of people make, or

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Speaker 2: at least I think it's a mistake, is Indian kids

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Speaker 2: will come and hang out with the other Indian students

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Speaker 2: Chinese because we'll hang out the other Chinese students, and

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Speaker 2: I think, yes, you can have one friend group from there,

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Speaker 2: but you know you're starting a new life, like assimilate

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Speaker 2: and meet people from everywhere versus sticking to your own

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Speaker 2: kind or whatever.

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Speaker 1: Yeah, and I feel like you having left India at

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Speaker 1: such a young age and growing up in Oman and

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Speaker 1: then moving to the US like having those kind of.

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Speaker 2: Currect I already didn't have a single group I could

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Speaker 2: go with where I'm like, we're exactly alike.

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Speaker 1: Yeah, that must That probably helps so much more than like,

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Speaker 1: you know, you ever really thought. Okay, well, let's talk

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Speaker 1: about your experience at UC Berkeley, because it was transformative.

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Speaker 1: I want to dive into the Facebook apps, so paint

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Speaker 1: the picture for us. What were you like as a

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Speaker 1: freshman you're student, and when did you first start becoming

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Speaker 1: entrepreneurial on your own?

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Speaker 2: Yeah? So freshman year, I I mean I still personality

416
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Speaker 2: wise was the same. I spent all my time trying

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Speaker 2: to figure out, you know, how could I get good

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Speaker 2: grades while being the least amount of work. Yet I

419
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Speaker 2: always had this guilt that my parents were spending a

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Speaker 2: huge part of their life savings to send me to college. Right,

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Speaker 2: So there's a guilt kind of wing on me. So

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Speaker 2: I would always go to class and be pretty responsible.

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Speaker 2: I got a campus job my second semester. I got

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Speaker 2: an internship at Amazon after my freshman year, which at

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Speaker 2: the time I was like, Wow, this is like sick.

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Speaker 2: I was eighteen earning five grand a month. There's a

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Speaker 2: lot of money back then, still a lot of money.

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Speaker 2: It's still a lot of money.

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Speaker 1: Everybody that I was making when I first graduated college,

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Speaker 1: I'm pretty sure.

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Speaker 2: Yeah, yeah. And I was an intern and I moved

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Speaker 2: to a Seattle to intern at Amazon as an eighteen

433
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Speaker 2: year old, and for the first time in my life,

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Speaker 2: I felt positively miserable in Seattle. I was super homesick

435
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Speaker 2: because it was the first summer back. All my friends

436
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Speaker 2: were back home. I had this like, I don't know

437
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Speaker 2: if other people have felt this, but your first adult

438
00:19:49,880 --> 00:19:52,240
Speaker 2: job kind of sucks. Like you realize you go to

439
00:19:52,240 --> 00:19:54,959
Speaker 2: the office, you're there for so long, you come back,

440
00:19:55,000 --> 00:19:56,600
Speaker 2: you're kind of tired, and if you do it all

441
00:19:56,640 --> 00:19:59,879
Speaker 2: over again. I was eighteen. I didn't know anyone in

442
00:20:00,040 --> 00:20:02,480
Speaker 2: Seattle who was the same age as me. I didn't

443
00:20:02,480 --> 00:20:04,440
Speaker 2: have a fake idea, so I couldn't even go out

444
00:20:04,480 --> 00:20:08,800
Speaker 2: to places. But the upside of that is it coincided

445
00:20:08,840 --> 00:20:12,360
Speaker 2: with the launch of the Facebook platform, where you could

446
00:20:12,440 --> 00:20:15,879
Speaker 2: create little games and quizzes on Facebook, and having nothing

447
00:20:15,880 --> 00:20:18,320
Speaker 2: else to do on nights and weekends, I started to

448
00:20:18,359 --> 00:20:20,359
Speaker 2: play around with that, and by the end of that

449
00:20:20,440 --> 00:20:22,640
Speaker 2: summer got to a point of making you know, ten

450
00:20:22,720 --> 00:20:26,200
Speaker 2: or twenty dollars per day. And I have never had

451
00:20:26,240 --> 00:20:28,920
Speaker 2: a job since that Amazon internship. It also just made

452
00:20:28,920 --> 00:20:31,560
Speaker 2: me realize having a large job is so soul crushing.

453
00:20:32,080 --> 00:20:35,120
Speaker 2: There was a time, firstly, my entire team at Amazon

454
00:20:35,520 --> 00:20:37,480
Speaker 2: worked on such a small thing. My entire team worked

455
00:20:37,480 --> 00:20:40,520
Speaker 2: on one page inside one dashboard. And there were a

456
00:20:40,560 --> 00:20:42,840
Speaker 2: couple of days where I didn't go into the office

457
00:20:43,280 --> 00:20:46,520
Speaker 2: and no one even realized how horrible is that that,

458
00:20:46,600 --> 00:20:49,919
Speaker 2: like you matter so little? Like I was such an

459
00:20:49,960 --> 00:20:52,560
Speaker 2: annoyance for my boss that he didn't care if I

460
00:20:52,560 --> 00:20:53,560
Speaker 2: showed up or didn't.

461
00:20:53,880 --> 00:20:56,760
Speaker 1: Yeah, Like, when you take a really entrepreneurial kid that

462
00:20:56,840 --> 00:21:01,119
Speaker 1: loves building things and working for yourself, and you know, yeah,

463
00:21:01,359 --> 00:21:03,680
Speaker 1: just you love building things, like and then you put

464
00:21:03,680 --> 00:21:05,840
Speaker 1: them in a nine to five job, you really are

465
00:21:05,880 --> 00:21:08,680
Speaker 1: like a cog in the system, a CS job at Amazon.

466
00:21:08,720 --> 00:21:10,240
Speaker 1: I mean, that's just not the right place for me.

467
00:21:10,280 --> 00:21:12,040
Speaker 2: I wouldn't hire myself. As someone that hires a lot

468
00:21:12,080 --> 00:21:13,920
Speaker 2: of people, I would absolutely not hire myself.

469
00:21:14,000 --> 00:21:15,840
Speaker 1: Yeah, well, of course not. You don't want somebody that

470
00:21:16,040 --> 00:21:18,359
Speaker 1: you know wants to start their own thing or your company.

471
00:21:19,480 --> 00:21:22,639
Speaker 1: Let's talk about building the Facebook apps, and you know

472
00:21:22,680 --> 00:21:24,800
Speaker 1: what Facebook kind of looked like at the time, and

473
00:21:25,080 --> 00:21:26,840
Speaker 1: how you guys started making money from it.

474
00:21:27,040 --> 00:21:29,720
Speaker 2: Yeah, absolutely so back in the day. I mean, now

475
00:21:29,760 --> 00:21:33,040
Speaker 2: Facebook is the old person platform, but back then it

476
00:21:33,160 --> 00:21:35,840
Speaker 2: was the place to be right our first few years

477
00:21:35,840 --> 00:21:38,760
Speaker 2: of college, everything was shaped by it. When my freshman

478
00:21:38,840 --> 00:21:40,840
Speaker 2: year of college, Facebook was for college is only I

479
00:21:40,840 --> 00:21:42,720
Speaker 2: think by my sophomore year that expanded to other high

480
00:21:42,720 --> 00:21:45,480
Speaker 2: schools and stuff. But it was growing really fast. It

481
00:21:45,480 --> 00:21:48,320
Speaker 2: was a hotbed of activity, and they allowed anyone to

482
00:21:48,359 --> 00:21:51,720
Speaker 2: build an application on the platform, and as a result,

483
00:21:51,800 --> 00:21:55,000
Speaker 2: you could build something and potentially have millions of users

484
00:21:55,480 --> 00:21:58,760
Speaker 2: within the span of a few days. It was quite

485
00:21:58,880 --> 00:22:01,280
Speaker 2: unlike anything we've seen seen up until that point on

486
00:22:01,320 --> 00:22:03,879
Speaker 2: the Internet, where if you had to reach millions of people,

487
00:22:03,960 --> 00:22:06,600
Speaker 2: it was super difficult. But I spent the next three

488
00:22:06,680 --> 00:22:09,520
Speaker 2: years in college building all kinds of games and quizzes

489
00:22:09,560 --> 00:22:12,679
Speaker 2: and these hyper viral apps that would reach millions and

490
00:22:12,680 --> 00:22:16,360
Speaker 2: millions of people. So things like personality quizzes or somewhat

491
00:22:16,400 --> 00:22:18,560
Speaker 2: would answer five questions. It would tell them how good

492
00:22:18,560 --> 00:22:20,440
Speaker 2: a lover they are, just like stupid stuff.

493
00:22:20,160 --> 00:22:22,640
Speaker 1: Like that, how are you coming up with the ideas

494
00:22:22,640 --> 00:22:23,280
Speaker 1: for the quizzes?

495
00:22:23,560 --> 00:22:25,800
Speaker 2: So initially I would try and do a lot of

496
00:22:25,800 --> 00:22:28,920
Speaker 2: research work quite hard. Then I realized it doesn't matter

497
00:22:29,000 --> 00:22:32,159
Speaker 2: as long as you write good enough descriptions, like we

498
00:22:32,200 --> 00:22:34,920
Speaker 2: had a quiz called what color is your Aura? And

499
00:22:35,440 --> 00:22:37,920
Speaker 2: as long as the descriptions were good where it's reads

500
00:22:37,920 --> 00:22:39,600
Speaker 2: like a horoscope, where it's like, you know you're the

501
00:22:39,600 --> 00:22:43,040
Speaker 2: color of your aura is black, Kate, You're mysterious. People

502
00:22:43,080 --> 00:22:44,639
Speaker 2: think they know the real you, but they don't know

503
00:22:44,640 --> 00:22:47,679
Speaker 2: who's actually behind it all. And as long as you

504
00:22:47,760 --> 00:22:50,360
Speaker 2: kind of gave people what they wanted to share, that's

505
00:22:50,400 --> 00:22:53,600
Speaker 2: what really mattered. If we had a quiz, which friend's

506
00:22:53,680 --> 00:22:57,120
Speaker 2: character are you, people didn't care what character they are.

507
00:22:57,359 --> 00:22:59,560
Speaker 2: They would take the quiz over and over till they

508
00:22:59,600 --> 00:23:01,880
Speaker 2: got the care they wanted and they would share that.

509
00:23:02,680 --> 00:23:05,760
Speaker 2: So it was fascinating you get such a cool insight

510
00:23:05,800 --> 00:23:08,679
Speaker 2: into human psychology with millions of people.

511
00:23:08,840 --> 00:23:10,720
Speaker 1: How much money were you making from these quizzes?

512
00:23:10,880 --> 00:23:14,600
Speaker 2: So by the time I turned twenty one, I hit

513
00:23:14,680 --> 00:23:17,600
Speaker 2: a million dollars through this. It started out with ten

514
00:23:17,680 --> 00:23:20,040
Speaker 2: or twenty bucks a day. It peaked at tens of

515
00:23:20,080 --> 00:23:22,760
Speaker 2: thousands of dollars a day. I think our biggest day

516
00:23:22,840 --> 00:23:25,719
Speaker 2: was like fifty grand a day. But it was up

517
00:23:25,760 --> 00:23:28,600
Speaker 2: and down, right, You'd be very popular for like six days,

518
00:23:28,600 --> 00:23:29,800
Speaker 2: then would die down entirely.

519
00:23:30,040 --> 00:23:33,160
Speaker 1: And when you say our, you basically are saying that

520
00:23:33,240 --> 00:23:36,480
Speaker 1: you went from doing this on your own late nights

521
00:23:36,520 --> 00:23:39,320
Speaker 1: after your internship at Amazon summer of your freshman year

522
00:23:39,520 --> 00:23:42,240
Speaker 1: to then what recruiting people at Burris recreated all my roommates.

523
00:23:42,320 --> 00:23:44,879
Speaker 2: My head like, and this is so different, right, you like,

524
00:23:45,560 --> 00:23:47,600
Speaker 2: it's doing business when you don't know anything about business.

525
00:23:47,760 --> 00:23:50,000
Speaker 2: Anyone I recruited, I'm like, okay, fine, you do this,

526
00:23:50,080 --> 00:23:51,919
Speaker 2: you get thirty percent of revenue. You do this, you

527
00:23:51,960 --> 00:23:54,680
Speaker 2: get twenty percent. It was the craziest deals that didn't

528
00:23:54,680 --> 00:23:56,920
Speaker 2: make any sense, but it was really fun. Like we

529
00:23:57,000 --> 00:23:59,400
Speaker 2: I lived with three people who ended up and still

530
00:23:59,400 --> 00:24:02,560
Speaker 2: are amongst my closest friends. Brought them in on the business,

531
00:24:02,640 --> 00:24:06,080
Speaker 2: hired developers. It was a good crash course in building

532
00:24:06,080 --> 00:24:07,760
Speaker 2: a business before I even turned twenty one.

533
00:24:07,880 --> 00:24:10,600
Speaker 1: What do you think the Facebook quiz has taught you

534
00:24:10,640 --> 00:24:14,320
Speaker 1: about business that was applicable to you, know your future

535
00:24:14,359 --> 00:24:16,280
Speaker 1: businesses like teachable and what you're doing now.

536
00:24:16,400 --> 00:24:20,560
Speaker 2: I think it taught me about growth specifically, like that

537
00:24:20,840 --> 00:24:23,840
Speaker 2: entire platform was a time when you had to do

538
00:24:23,920 --> 00:24:26,720
Speaker 2: so much social engineering to grow anything. And I think

539
00:24:26,760 --> 00:24:28,800
Speaker 2: a lot of those lessons have stayed with me today

540
00:24:29,080 --> 00:24:31,800
Speaker 2: even now. I've never had as many people use anything

541
00:24:31,840 --> 00:24:34,480
Speaker 2: I've built since then. Like back in the day, we

542
00:24:34,560 --> 00:24:36,600
Speaker 2: peaked at about two to three million people a day.

543
00:24:37,640 --> 00:24:39,840
Speaker 2: There was a time where we had more traffic than

544
00:24:39,880 --> 00:24:44,000
Speaker 2: the New York Times, more traffic than LinkedIn. It was crazy,

545
00:24:44,000 --> 00:24:47,560
Speaker 2: and you know it was from a dorm room, so insane, so.

546
00:24:47,760 --> 00:24:52,320
Speaker 1: Nuts, And did you guys continue doing it throughout college? Like?

547
00:24:52,359 --> 00:24:53,840
Speaker 1: How long did this last for?

548
00:24:54,080 --> 00:24:58,119
Speaker 2: I did it till about a year or so after college.

549
00:24:58,200 --> 00:25:00,720
Speaker 2: It would always ebb and flow since you at shutdown

550
00:25:00,920 --> 00:25:04,200
Speaker 2: or the rules would change or the applications get less popular.

551
00:25:05,359 --> 00:25:09,000
Speaker 2: But after like this fifth or sixth time shutdown, I

552
00:25:09,080 --> 00:25:12,120
Speaker 2: started to feel like I wanted to build something more substantial,

553
00:25:12,480 --> 00:25:14,840
Speaker 2: because as cool as this was, you were only as

554
00:25:14,880 --> 00:25:18,840
Speaker 2: good as yesterday's revenue. You were building no enterprise value.

555
00:25:19,160 --> 00:25:21,400
Speaker 2: But also at a certain point, games and quizes are fun,

556
00:25:21,440 --> 00:25:23,680
Speaker 2: but you look back and you're like, am I truly

557
00:25:23,920 --> 00:25:25,880
Speaker 2: making people's lives better? Yeah.

558
00:25:25,920 --> 00:25:27,600
Speaker 1: And also if you like think about it in like

559
00:25:27,600 --> 00:25:29,760
Speaker 1: the lifespan that you're saying for the games, you wanted

560
00:25:29,800 --> 00:25:32,240
Speaker 1: to building that with something that was sustainable. Did any

561
00:25:32,280 --> 00:25:36,560
Speaker 1: of the people that helped you build out these apps

562
00:25:36,600 --> 00:25:40,760
Speaker 1: on Facebook end up working at teachable?

563
00:25:41,040 --> 00:25:43,280
Speaker 2: No. Two of them are finance bros. And ones of

564
00:25:43,280 --> 00:25:45,679
Speaker 2: plastic surgeons. I went in completely different worlds.

565
00:25:45,680 --> 00:25:47,960
Speaker 1: Wow, Okay, so it really was a sideholso for you

566
00:25:48,040 --> 00:25:50,679
Speaker 1: as in college. Then what happened after college? Where did

567
00:25:50,680 --> 00:25:51,320
Speaker 1: you start working?

568
00:25:51,680 --> 00:25:54,240
Speaker 2: After college? I had the two years, i would say,

569
00:25:54,280 --> 00:25:57,199
Speaker 2: of trying different ideas and nothing quite clicks. I probably

570
00:25:57,240 --> 00:26:01,760
Speaker 2: tried twelve or fourteen different startups. And at the time

571
00:26:01,840 --> 00:26:05,840
Speaker 2: that was also when I decided to it wasn't working

572
00:26:05,840 --> 00:26:07,560
Speaker 2: and pack my bags and move to New York City

573
00:26:07,600 --> 00:26:10,199
Speaker 2: and try to almost start over. And that was the

574
00:26:10,240 --> 00:26:12,520
Speaker 2: time I think my parents' faith was tested a little

575
00:26:12,560 --> 00:26:15,480
Speaker 2: bit because there was a divergence in what my mom

576
00:26:15,520 --> 00:26:17,960
Speaker 2: and dad wanted. My dad's like, yeah, keep going, it

577
00:26:17,960 --> 00:26:20,120
Speaker 2: doesn't matter, like who cares this, You'll figure it out.

578
00:26:20,520 --> 00:26:23,000
Speaker 2: My mom's like, well, why don't you work at Facebook?

579
00:26:23,040 --> 00:26:25,479
Speaker 2: You know they could hire you. Can't someone hire you?

580
00:26:25,520 --> 00:26:28,639
Speaker 2: But I'm glad I stuck it out until then starting

581
00:26:28,680 --> 00:26:29,800
Speaker 2: teachable when I was twenty four.

582
00:26:30,040 --> 00:26:32,040
Speaker 1: I love knowing how supportive your parents were.

583
00:26:32,240 --> 00:26:34,879
Speaker 2: They were and continue to be incredibly supportive, like they.

584
00:26:34,800 --> 00:26:36,399
Speaker 1: Just always knew that you were going to make it

585
00:26:36,400 --> 00:26:37,600
Speaker 1: happen on your own, my.

586
00:26:37,760 --> 00:26:39,719
Speaker 2: Dad more so than my mom. But yeah, I did.

587
00:26:40,040 --> 00:26:43,480
Speaker 2: It did work out. Through this whole process, immigration was

588
00:26:43,520 --> 00:26:47,960
Speaker 2: a stressor because I had a student visa. I sponsored

589
00:26:47,960 --> 00:26:51,160
Speaker 2: my own student visa. I then extended it, and then

590
00:26:51,200 --> 00:26:53,720
Speaker 2: at one point, which is around the time right before

591
00:26:53,720 --> 00:26:55,920
Speaker 2: moving to New York City, I had to leave the country.

592
00:26:55,960 --> 00:26:57,480
Speaker 2: I was told I had to leave the country, so

593
00:26:57,520 --> 00:27:00,199
Speaker 2: I googled the cheapest community college I could find get

594
00:27:00,240 --> 00:27:03,800
Speaker 2: another student visa. But I constantly had this sort of

595
00:27:03,840 --> 00:27:07,520
Speaker 2: stress of I can't legally stay here unless I figure

596
00:27:07,560 --> 00:27:10,159
Speaker 2: this immigration stuff out. So that does make things a

597
00:27:10,160 --> 00:27:10,719
Speaker 2: lot harder.

598
00:27:10,840 --> 00:27:12,440
Speaker 1: How did you finally figure it out?

599
00:27:12,640 --> 00:27:14,959
Speaker 2: I finally got a very good lawyer, and I applied

600
00:27:15,000 --> 00:27:17,800
Speaker 2: for something called the one visa, which is an extraordinary

601
00:27:17,800 --> 00:27:20,679
Speaker 2: ability visa, but it's something that the alien of extraordinary

602
00:27:20,720 --> 00:27:23,960
Speaker 2: alien exactly. It's very welcoming visa. But from there I

603
00:27:23,960 --> 00:27:25,840
Speaker 2: got my green card and eventually passport.

604
00:27:26,040 --> 00:27:28,679
Speaker 1: Wow. And then by building your business here does that

605
00:27:28,760 --> 00:27:29,560
Speaker 1: help with immigration?

606
00:27:29,760 --> 00:27:32,440
Speaker 2: So I only started Teachable when I figured out immigration.

607
00:27:32,480 --> 00:27:35,119
Speaker 2: It was got challenging enough that as soon as I

608
00:27:35,160 --> 00:27:37,400
Speaker 2: got that, I formally incorporated Teachable.

609
00:27:37,640 --> 00:27:39,960
Speaker 1: Well, let's talk about how the idea for teachable came

610
00:27:40,000 --> 00:27:42,119
Speaker 1: to be, and I want to premise this with guys

611
00:27:42,359 --> 00:27:45,119
Speaker 1: when Encore was thirty one. He started it at twenty

612
00:27:45,160 --> 00:27:48,080
Speaker 1: four and by thirty one he sold Teachable for two

613
00:27:48,200 --> 00:27:52,520
Speaker 1: hundred and fifty million dollars, which is incredible. But let's

614
00:27:52,600 --> 00:27:54,639
Speaker 1: start with the basics. How did you guys get the

615
00:27:54,680 --> 00:27:57,400
Speaker 1: idea for teachable? And you know what did it start

616
00:27:57,440 --> 00:27:59,280
Speaker 1: out as? And then kind of what did it evolve into?

617
00:27:59,440 --> 00:28:02,240
Speaker 2: Yeah, absolute, So it was never a big grand vision

618
00:28:02,320 --> 00:28:05,160
Speaker 2: or a grand idea. It was one of many different

619
00:28:05,440 --> 00:28:08,840
Speaker 2: side hustles or things we were trying. Where my buddy

620
00:28:08,840 --> 00:28:11,159
Speaker 2: Conrad and I we started. We saw this platform you

621
00:28:11,200 --> 00:28:13,680
Speaker 2: to Me, had come out where you could sell online courses,

622
00:28:13,960 --> 00:28:16,600
Speaker 2: so we decided to help some people sell their courses.

623
00:28:17,080 --> 00:28:19,320
Speaker 2: We soon realized why don't we create our own courses,

624
00:28:19,800 --> 00:28:23,200
Speaker 2: did that and then found a lot of challenges with

625
00:28:23,240 --> 00:28:25,240
Speaker 2: the you to me model where it was a marketplace.

626
00:28:25,680 --> 00:28:28,840
Speaker 2: They kept a really high revenue share. They owned the customer.

627
00:28:29,240 --> 00:28:31,760
Speaker 2: So I built the first version of Teachable almost as

628
00:28:31,800 --> 00:28:36,240
Speaker 2: a side project for my buddy Conrad, and we sold

629
00:28:36,359 --> 00:28:38,720
Speaker 2: a couple thousand dollars of courses when we launched, and

630
00:28:39,480 --> 00:28:41,600
Speaker 2: was like, okay, maybe there's a real idea here, and

631
00:28:41,640 --> 00:28:43,200
Speaker 2: then started offering it to other people.

632
00:28:43,400 --> 00:28:46,240
Speaker 1: And when you say you were selling courses, like were

633
00:28:46,240 --> 00:28:48,120
Speaker 1: you having other people create the courses?

634
00:28:48,240 --> 00:28:50,040
Speaker 2: So it started with other people, and then we said,

635
00:28:50,040 --> 00:28:52,000
Speaker 2: why don't we create our own courses. We had courses

636
00:28:52,000 --> 00:28:54,960
Speaker 2: on the whatever I did with the Facebook apps, growth marketing,

637
00:28:55,560 --> 00:28:56,040
Speaker 2: all of that.

638
00:28:56,320 --> 00:28:58,400
Speaker 1: It's so interesting. And it started as like it was

639
00:28:58,400 --> 00:29:00,320
Speaker 1: almost like a social media platform.

640
00:29:00,200 --> 00:29:03,160
Speaker 2: Right, yeah, I was super unintentional. It was. It was

641
00:29:03,200 --> 00:29:05,880
Speaker 2: always selling courses in your own websites. The product didn't

642
00:29:05,920 --> 00:29:08,880
Speaker 2: change much. But this is before the creator economy, right.

643
00:29:08,920 --> 00:29:12,400
Speaker 2: We didn't know Instagram, YouTube, everything would blow up. They'd

644
00:29:12,440 --> 00:29:14,959
Speaker 2: be all these big creators. We thought our target audience

645
00:29:15,000 --> 00:29:17,880
Speaker 2: was educators, so we got that frong. But as we

646
00:29:17,960 --> 00:29:20,360
Speaker 2: kept building the business, you know, the creator economy happened

647
00:29:20,360 --> 00:29:24,240
Speaker 2: and people started selling millions and eventually hundreds of millions

648
00:29:24,280 --> 00:29:25,440
Speaker 2: of dollars a year of courses.

649
00:29:25,800 --> 00:29:29,440
Speaker 1: When did you guys realize that the company was going

650
00:29:29,520 --> 00:29:31,360
Speaker 1: from a startup to a real business.

651
00:29:31,680 --> 00:29:34,200
Speaker 2: Probably so we It took us six months of just

652
00:29:34,280 --> 00:29:37,040
Speaker 2: messing around before I decided to incorporate and raise money.

653
00:29:37,360 --> 00:29:40,360
Speaker 2: I would say about a year after that it started

654
00:29:40,400 --> 00:29:42,680
Speaker 2: to feel like we started to make tens of thousands

655
00:29:42,720 --> 00:29:45,000
Speaker 2: of dollars a month. And at that point it's like

656
00:29:45,760 --> 00:29:47,800
Speaker 2: we maybe on we may be onto something, You may be.

657
00:29:47,840 --> 00:29:49,320
Speaker 1: Onto something, and you're like, we need to make sure

658
00:29:49,320 --> 00:29:51,240
Speaker 1: we have the right team here. Let's talk a little

659
00:29:51,240 --> 00:29:53,320
Speaker 1: bit about hiring people, because I think that is one

660
00:29:53,320 --> 00:29:56,080
Speaker 1: of the hardest things for entrepreneurs, right, Like, what was

661
00:29:56,120 --> 00:29:59,920
Speaker 1: your hiring strategy when you guys really started growing tea?

662
00:30:00,560 --> 00:30:02,880
Speaker 2: Initially it was one hundred percent vibes Like I wish

663
00:30:02,920 --> 00:30:05,760
Speaker 2: I could say. We had an interview process our first

664
00:30:06,160 --> 00:30:09,560
Speaker 2: our first engineer who became our CTO. He showed up

665
00:30:09,560 --> 00:30:13,360
Speaker 2: like an hour late to the interview, and either way,

666
00:30:13,400 --> 00:30:15,720
Speaker 2: we had a good chat. I described like one thing

667
00:30:15,760 --> 00:30:18,560
Speaker 2: I was working on chat kind of I kind of

668
00:30:18,560 --> 00:30:20,560
Speaker 2: forget about it. The next morning he emails me at

669
00:30:20,560 --> 00:30:23,120
Speaker 2: like six am. He stayed up all night building a

670
00:30:23,160 --> 00:30:25,840
Speaker 2: working prototype of what I was talking to him about

671
00:30:25,960 --> 00:30:28,280
Speaker 2: I'm like, cool, you're hired. We'll figure out the details later.

672
00:30:28,320 --> 00:30:29,640
Speaker 1: Okay, that is more than vibes.

673
00:30:29,840 --> 00:30:32,200
Speaker 2: Hiring people on where they went to school or where

674
00:30:32,240 --> 00:30:33,760
Speaker 2: they worked has turned out to be one of the

675
00:30:33,760 --> 00:30:36,480
Speaker 2: worst strategies I've found. Indexing a lot on people who

676
00:30:36,520 --> 00:30:38,800
Speaker 2: want to be there. I also index a lot in

677
00:30:38,840 --> 00:30:42,440
Speaker 2: people who move fast for better or worse. My operating

678
00:30:42,480 --> 00:30:44,800
Speaker 2: style is quite fast, and sometimes it is chaotic. It's

679
00:30:44,800 --> 00:30:46,920
Speaker 2: not easy for other people to keep up with. But

680
00:30:47,000 --> 00:30:48,320
Speaker 2: I like that from the people I hire.

681
00:30:48,480 --> 00:30:50,720
Speaker 1: I've interviewed a lot of people like yourself that have

682
00:30:50,840 --> 00:30:54,240
Speaker 1: had this extreme level of success, and one of the

683
00:30:54,280 --> 00:30:56,920
Speaker 1: things that I've found with the most successful people is

684
00:30:56,920 --> 00:30:58,640
Speaker 1: that they're so quick to respond.

685
00:30:58,960 --> 00:31:01,120
Speaker 2: Like is that a common out of it's a commonality.

686
00:31:01,200 --> 00:31:03,680
Speaker 2: I also bet if I were to hypothesize, there's a

687
00:31:03,720 --> 00:31:06,440
Speaker 2: high correlation with ADD like better or worse. I mean,

688
00:31:06,600 --> 00:31:08,760
Speaker 2: I'm not medicated add but you know, I think if

689
00:31:08,760 --> 00:31:11,080
Speaker 2: I grew up in America, I may have been. But

690
00:31:11,320 --> 00:31:13,360
Speaker 2: where you either reply right away or you're going to

691
00:31:13,440 --> 00:31:15,600
Speaker 2: forget about it. So the ones the people who do

692
00:31:15,680 --> 00:31:18,640
Speaker 2: reply are the ones who reply pretty quickly. But yeah,

693
00:31:18,680 --> 00:31:21,160
Speaker 2: there's a just a bias towards action, right, I don't

694
00:31:21,240 --> 00:31:24,000
Speaker 2: like kind of waiting around on stuff. I'm also very

695
00:31:24,040 --> 00:31:26,600
Speaker 2: instinctive when it comes to making decisions, So I think

696
00:31:26,640 --> 00:31:28,920
Speaker 2: that tends to help. If I think about all the

697
00:31:29,000 --> 00:31:31,320
Speaker 2: things that have made me good at what I do

698
00:31:31,360 --> 00:31:34,760
Speaker 2: and successful, those traits have a negative expression as well,

699
00:31:34,800 --> 00:31:37,200
Speaker 2: and I think that's a great example where we can't

700
00:31:37,280 --> 00:31:39,719
Speaker 2: take the good parts of our personality without also getting

701
00:31:40,160 --> 00:31:42,680
Speaker 2: the bad part of the exact same trait. So, yes,

702
00:31:42,720 --> 00:31:44,920
Speaker 2: I'm also impulsive. I probably take too many risks, But

703
00:31:45,240 --> 00:31:47,040
Speaker 2: if not for that, I would not have gotten the

704
00:31:47,040 --> 00:31:48,239
Speaker 2: positive expressions of that.

705
00:31:48,440 --> 00:31:51,600
Speaker 1: When you guys first started out, what were the core

706
00:31:51,720 --> 00:31:54,480
Speaker 1: focuses for you when you were building your business? Like,

707
00:31:54,640 --> 00:31:56,520
Speaker 1: I know some of the things for you guys were

708
00:31:56,960 --> 00:31:59,640
Speaker 1: keeping outs bend low. You built a lot of your

709
00:31:59,680 --> 00:32:03,080
Speaker 1: moment off of organic growth, right, So like, let's talk

710
00:32:03,120 --> 00:32:05,520
Speaker 1: through those kinds of decisions and what made you guys.

711
00:32:05,880 --> 00:32:08,440
Speaker 2: Yeah, absolutely, I would say there's basically three phases of

712
00:32:08,440 --> 00:32:12,959
Speaker 2: our growth. Phase one was just unmitigated kind of stupid

713
00:32:13,040 --> 00:32:17,360
Speaker 2: hustle where we would do insane, unscalable things to make

714
00:32:17,360 --> 00:32:18,920
Speaker 2: the numbers go up no matter what.

715
00:32:19,040 --> 00:32:20,080
Speaker 1: Like what I give us some EXAMPCE.

716
00:32:20,160 --> 00:32:23,400
Speaker 2: So there was a time when there's this guy which

717
00:32:23,440 --> 00:32:25,040
Speaker 2: had we wanted to sign up on our platform. His

718
00:32:25,120 --> 00:32:27,040
Speaker 2: name was Pat Flynn. He was a very big deal

719
00:32:27,040 --> 00:32:29,520
Speaker 2: in the world of online courses. Then Pat kind of

720
00:32:29,640 --> 00:32:32,080
Speaker 2: was ignoring all my emails. So I started looking at

721
00:32:32,120 --> 00:32:34,240
Speaker 2: every single conference he was going to, and anytime I

722
00:32:34,320 --> 00:32:36,479
Speaker 2: go to a conference, I'm like, hey, Pat, I'm going

723
00:32:36,520 --> 00:32:38,920
Speaker 2: to be here. Finally he once I saw he was

724
00:32:38,920 --> 00:32:41,000
Speaker 2: going to be at this conference called fin Conn in

725
00:32:41,080 --> 00:32:44,000
Speaker 2: North Carolina somewhere. I hit up Pat. I'm like, hey, Pat,

726
00:32:44,000 --> 00:32:45,680
Speaker 2: I'm going to be at fin Conn. He's like, cool,

727
00:32:45,680 --> 00:32:48,440
Speaker 2: I'll meet you for breakfast eight thirty tomorrow. I gotta

728
00:32:48,440 --> 00:32:52,280
Speaker 2: get there now tonight. So flew there. Obviously I didn't

729
00:32:52,280 --> 00:32:54,520
Speaker 2: have a conference ticket. I wasn't going to the conference,

730
00:32:54,800 --> 00:32:56,920
Speaker 2: met him for breakfast, signed him as a customer. He

731
00:32:56,920 --> 00:32:59,800
Speaker 2: became an affiliate. I flew back after that meeting. It

732
00:32:59,920 --> 00:33:02,960
Speaker 2: was stuff like that we did repeatedly, Like we had

733
00:33:02,960 --> 00:33:06,880
Speaker 2: a month where our customers weren't selling a lot, or

734
00:33:07,000 --> 00:33:09,360
Speaker 2: we had sorry the next month, we didn't have any

735
00:33:09,360 --> 00:33:13,000
Speaker 2: big course launches. So Conrad and I gave up our

736
00:33:13,000 --> 00:33:16,480
Speaker 2: Thanksgiving plans flew to Berlin with our biggest creators, took

737
00:33:16,480 --> 00:33:20,080
Speaker 2: a camera, recorded something, launched it the week after. So

738
00:33:20,120 --> 00:33:22,680
Speaker 2: we just had to do these things in the early

739
00:33:22,760 --> 00:33:25,520
Speaker 2: days before there was an engine that really worked.

740
00:33:25,680 --> 00:33:27,880
Speaker 1: Yeah, no, it makes sense because it's like, you guys

741
00:33:27,920 --> 00:33:31,479
Speaker 1: have this platform that's built on courses, but you literally

742
00:33:31,480 --> 00:33:33,320
Speaker 1: need to find people, Like it can't just be you

743
00:33:33,360 --> 00:33:35,720
Speaker 1: guys making courses forever, like it has to be other

744
00:33:35,760 --> 00:33:38,640
Speaker 1: people as well. What were your other strategies to getting

745
00:33:38,640 --> 00:33:40,160
Speaker 1: people on Who was like the first person that you

746
00:33:40,200 --> 00:33:41,400
Speaker 1: guys got onto your platform.

747
00:33:41,400 --> 00:33:43,560
Speaker 2: So the first big person so we got the first

748
00:33:43,600 --> 00:33:45,720
Speaker 2: person was obviously Conrad. The first couple of people were

749
00:33:45,720 --> 00:33:49,280
Speaker 2: other unim ME creators. But something pretty fortunate happened where

750
00:33:49,400 --> 00:33:52,520
Speaker 2: two of our creators made a million dollars in the

751
00:33:52,560 --> 00:33:55,520
Speaker 2: first six months, and the benefit of that is so

752
00:33:55,640 --> 00:33:58,440
Speaker 2: much pr right now. It's like John and Elliott are

753
00:33:58,440 --> 00:34:00,640
Speaker 2: twenty seven and twenty eight traveling the world, made a

754
00:34:00,680 --> 00:34:03,240
Speaker 2: million dollars teaching people how to build iPhone apps. So

755
00:34:03,280 --> 00:34:06,280
Speaker 2: then that got us the first sort of growth spurt,

756
00:34:06,640 --> 00:34:09,400
Speaker 2: and that's what led to our primary growth strategy that

757
00:34:09,400 --> 00:34:12,839
Speaker 2: we ran for most of the company, which was storytelling

758
00:34:12,880 --> 00:34:17,040
Speaker 2: about other creators. We realized our competitive advantage is the

759
00:34:17,080 --> 00:34:19,920
Speaker 2: best creators on our platform, especially if they were in

760
00:34:19,960 --> 00:34:23,160
Speaker 2: the world of business or making money online, they in

761
00:34:23,160 --> 00:34:26,120
Speaker 2: turn could be our biggest affiliates in promoters. So that's

762
00:34:26,160 --> 00:34:28,240
Speaker 2: the strategy we used for the next three or four years.

763
00:34:28,400 --> 00:34:29,479
Speaker 1: Yeah, it makes so much sense.

764
00:34:29,520 --> 00:34:31,800
Speaker 2: It's like, now it's obvious. At the time it felt

765
00:34:31,840 --> 00:34:33,960
Speaker 2: like crazy, but now it's you look at these businesses.

766
00:34:34,040 --> 00:34:35,920
Speaker 1: Oh yeah, it's so true because it's like when you

767
00:34:35,920 --> 00:34:37,759
Speaker 1: think about I mean, when I think about YouTube, I'm like,

768
00:34:37,800 --> 00:34:39,000
Speaker 1: why do I want to be on YouTube? I'm like,

769
00:34:39,000 --> 00:34:40,680
Speaker 1: because so many of these other creators have had so

770
00:34:40,760 --> 00:34:43,120
Speaker 1: much success on YouTube, of course I want to like

771
00:34:43,200 --> 00:34:44,920
Speaker 1: try to have success on that app as well. It

772
00:34:44,920 --> 00:34:47,160
Speaker 1: makes the same It's kind of just something for Teachable,

773
00:34:47,480 --> 00:34:50,160
Speaker 1: and I think that's a cool notion to go into too,

774
00:34:50,200 --> 00:34:53,200
Speaker 1: because when you guys first started out, it was pretty

775
00:34:53,239 --> 00:34:55,680
Speaker 1: early on into the creator economy per se.

776
00:34:56,040 --> 00:34:58,680
Speaker 2: There was no creator economy. We stumbled into it, basically.

777
00:34:58,360 --> 00:35:01,760
Speaker 1: Literally stumbled into it. Like what did you learn about

778
00:35:01,760 --> 00:35:04,520
Speaker 1: the creator economy from building Teachable?

779
00:35:04,680 --> 00:35:06,879
Speaker 2: It was fascinating since again there was no such thing

780
00:35:06,880 --> 00:35:09,720
Speaker 2: as the creator economy. But then we started to look around.

781
00:35:09,719 --> 00:35:13,480
Speaker 2: We're like, where can we find people that could be creators.

782
00:35:13,840 --> 00:35:16,680
Speaker 2: An insight that seems obvious now is we realize it's

783
00:35:16,719 --> 00:35:19,240
Speaker 2: easier to teach someone with an audience how to teach

784
00:35:19,760 --> 00:35:21,759
Speaker 2: than it is to teach a teacher how to build

785
00:35:21,760 --> 00:35:23,880
Speaker 2: an audience. The other thing is, I think we got

786
00:35:24,400 --> 00:35:27,960
Speaker 2: fortunate in timing, like we rode the wave of when

787
00:35:28,000 --> 00:35:30,800
Speaker 2: online courses were really big. Like I think the heyday

788
00:35:30,840 --> 00:35:33,480
Speaker 2: of courses were sort of twenty seventeen, almost peaking in

789
00:35:33,520 --> 00:35:36,319
Speaker 2: twenty twenty, and they've sort of declined a little bit.

790
00:35:36,600 --> 00:35:38,720
Speaker 2: I still think the creator economy is and will continue

791
00:35:38,760 --> 00:35:41,200
Speaker 2: to be massive, but the exact products will keep changing.

792
00:35:52,200 --> 00:35:55,440
Speaker 1: How soon into you guys creating Teachable did things like

793
00:35:55,520 --> 00:35:56,640
Speaker 1: master Class come out.

794
00:35:56,680 --> 00:35:59,480
Speaker 2: I would say roughly midway through they were out. But

795
00:35:59,520 --> 00:36:01,960
Speaker 2: they were always different variants. When we started, for instance,

796
00:36:02,239 --> 00:36:04,160
Speaker 2: skill share was really big and then they kind of,

797
00:36:04,360 --> 00:36:07,759
Speaker 2: you know, disappeared. There's a company called Creative Live. There

798
00:36:07,760 --> 00:36:11,360
Speaker 2: were always different form factors. What we got fortunate on

799
00:36:11,760 --> 00:36:14,759
Speaker 2: is by empowering the creator. We were very close to

800
00:36:14,800 --> 00:36:18,200
Speaker 2: Shopify but for information, but that meant the creator did

801
00:36:18,239 --> 00:36:20,560
Speaker 2: all the distribution. We were just the technology platform.

802
00:36:20,640 --> 00:36:21,840
Speaker 1: It would have been cool if there was, like I

803
00:36:21,840 --> 00:36:23,759
Speaker 1: don't know if there was like a teachable Times master

804
00:36:23,800 --> 00:36:25,960
Speaker 1: class type of thing, because you would, like they're very different.

805
00:36:26,800 --> 00:36:29,000
Speaker 2: We did. We did a few deals like that where

806
00:36:29,040 --> 00:36:32,560
Speaker 2: we'd help people create content, and what we soon found

807
00:36:32,680 --> 00:36:35,440
Speaker 2: is those businesses are hard enough that anytime we did that,

808
00:36:35,800 --> 00:36:37,560
Speaker 2: it turned into a shit show we were not prepared

809
00:36:37,560 --> 00:36:40,600
Speaker 2: for because you start doing something that's not your business,

810
00:36:41,000 --> 00:36:43,759
Speaker 2: and it's just a constant reminder that you have to

811
00:36:44,040 --> 00:36:45,319
Speaker 2: be better at saying no to things.

812
00:36:45,520 --> 00:36:48,239
Speaker 1: Yeah. Absolutely, well. When I think about Masterclass two, I

813
00:36:48,280 --> 00:36:51,080
Speaker 1: almost think of like it's like a mini TV show, right,

814
00:36:51,200 --> 00:36:52,600
Speaker 1: Like it's like a mini TV series.

815
00:36:52,800 --> 00:36:55,400
Speaker 2: So master Class. The problem Masterclass is like, the best

816
00:36:55,400 --> 00:36:58,600
Speaker 2: teachers we find are not the celebrities, right. The best

817
00:36:58,600 --> 00:37:01,799
Speaker 2: teachers are someone whose story you relate to. Like I

818
00:37:01,920 --> 00:37:04,200
Speaker 2: don't want to learn how to shoot a basketball from

819
00:37:04,239 --> 00:37:06,160
Speaker 2: Steph Currery. I want to learn from the other Indian

820
00:37:06,239 --> 00:37:08,719
Speaker 2: kid who's probably better than me, right, And people want

821
00:37:08,760 --> 00:37:12,680
Speaker 2: that relatability and Masterclass you right, it's entertainment less of education.

822
00:37:12,920 --> 00:37:15,120
Speaker 1: What was it like selling a company during COVID.

823
00:37:14,920 --> 00:37:16,880
Speaker 2: It was wild? I mean, you have nothing to compare

824
00:37:16,920 --> 00:37:19,600
Speaker 2: it to at all, but it was at the same

825
00:37:19,680 --> 00:37:24,360
Speaker 2: time it felt like a weight off my back. Yet

826
00:37:24,960 --> 00:37:28,040
Speaker 2: it was also hard. Right, you've been building this thing,

827
00:37:28,120 --> 00:37:29,879
Speaker 2: you care so much about this thing, and now it's

828
00:37:29,920 --> 00:37:33,680
Speaker 2: someone else's thing. What made it even more interesting slash

829
00:37:33,680 --> 00:37:36,840
Speaker 2: complicated is right the day after we sold it to

830
00:37:36,920 --> 00:37:40,240
Speaker 2: three months later, the business doubled. We saw more growth,

831
00:37:40,880 --> 00:37:43,359
Speaker 2: more like it was. The craziest times at work were

832
00:37:43,400 --> 00:37:46,120
Speaker 2: right after we sold, which honesty was probably good because

833
00:37:46,120 --> 00:37:47,680
Speaker 2: there was so much else happening in New York. New

834
00:37:47,760 --> 00:37:49,960
Speaker 2: York was a terrifying place of the time that it

835
00:37:50,040 --> 00:37:53,600
Speaker 2: kept us busy, but it never the realization almost never

836
00:37:53,680 --> 00:37:56,120
Speaker 2: sank in since you were so caught up in the day.

837
00:37:56,040 --> 00:37:58,239
Speaker 1: To day, you ended up still working on it for

838
00:37:58,280 --> 00:38:00,960
Speaker 1: the next for a few months. Was selling, right, So

839
00:38:01,080 --> 00:38:03,040
Speaker 1: let's talk about what those months kind of looked like,

840
00:38:03,160 --> 00:38:05,719
Speaker 1: and how your position at the company changed after selling it,

841
00:38:05,760 --> 00:38:07,719
Speaker 1: and maybe what those emotions are like once you sell

842
00:38:07,719 --> 00:38:08,200
Speaker 1: a company.

843
00:38:08,400 --> 00:38:10,719
Speaker 2: Yeah, so the emotions again, as I said, it's very

844
00:38:10,760 --> 00:38:13,680
Speaker 2: different because we were all in lockdown. There was no

845
00:38:13,800 --> 00:38:17,279
Speaker 2: cathartic like post exit party. I still get people from

846
00:38:17,280 --> 00:38:19,640
Speaker 2: the company who tell me that I owe them that

847
00:38:19,640 --> 00:38:22,359
Speaker 2: they're like, we never got to celebrate, like we all

848
00:38:22,480 --> 00:38:25,400
Speaker 2: to post sort of exit party. So it was it

849
00:38:25,400 --> 00:38:27,279
Speaker 2: was definitely a little bit more complicated since you're in

850
00:38:27,320 --> 00:38:29,520
Speaker 2: lockdown and kind of coming to grips with all of that.

851
00:38:30,320 --> 00:38:33,360
Speaker 2: For me, my life only really changed when I stepped

852
00:38:33,400 --> 00:38:35,960
Speaker 2: away from the role entirely, Like my life did not

853
00:38:36,080 --> 00:38:38,800
Speaker 2: feel different just having more money in the bank or whatever.

854
00:38:39,960 --> 00:38:42,160
Speaker 2: And by the end, and this also related to why

855
00:38:42,160 --> 00:38:44,720
Speaker 2: I sold the company, I don't think I was enjoying

856
00:38:44,719 --> 00:38:47,759
Speaker 2: it that much. The reason being, I felt like a

857
00:38:47,760 --> 00:38:51,279
Speaker 2: lot of my role was typical CEO stuff, which is

858
00:38:51,320 --> 00:38:54,279
Speaker 2: so much less fun than building and creating things, where

859
00:38:54,360 --> 00:38:57,200
Speaker 2: I had to deal with executives who had managers who

860
00:38:57,200 --> 00:38:59,680
Speaker 2: had other reports, and you spend all your life in

861
00:38:59,719 --> 00:39:03,279
Speaker 2: these long meetings every day, and it felt like it

862
00:39:03,320 --> 00:39:06,520
Speaker 2: was going nowhere. But when I stepped back is when

863
00:39:06,520 --> 00:39:09,040
Speaker 2: I really found the quality of my life improved.

864
00:39:09,239 --> 00:39:10,520
Speaker 1: What is your role now? I care?

865
00:39:10,719 --> 00:39:13,200
Speaker 2: Right right now, I am also the CEO, But when

866
00:39:13,239 --> 00:39:15,560
Speaker 2: you're a small company, I don't think it's really a CEO.

867
00:39:15,560 --> 00:39:17,920
Speaker 2: I think you only really become a CEO in a

868
00:39:18,000 --> 00:39:21,040
Speaker 2: true executive way when you have fifty hundred people and

869
00:39:21,400 --> 00:39:23,520
Speaker 2: if I feel the same way in the future, I'll

870
00:39:23,520 --> 00:39:25,320
Speaker 2: step away and bring in someone more qualified.

871
00:39:25,400 --> 00:39:27,360
Speaker 1: What do you think is your favorite thing about building

872
00:39:27,360 --> 00:39:27,880
Speaker 1: a business?

873
00:39:28,320 --> 00:39:33,080
Speaker 2: The people? Undoubtedly, like I look back on all the times.

874
00:39:33,719 --> 00:39:36,840
Speaker 2: Yes we made money, Yes we built a successful business,

875
00:39:37,480 --> 00:39:40,719
Speaker 2: but it's always the relationships. It's the team. So many

876
00:39:40,800 --> 00:39:44,520
Speaker 2: of the customers are still friends, our earliest investors. These

877
00:39:44,560 --> 00:39:48,960
Speaker 2: are lifelong relationships that compound and grow. I also think

878
00:39:49,280 --> 00:39:52,040
Speaker 2: having a good time while you're doing the whole thing

879
00:39:52,480 --> 00:39:55,160
Speaker 2: takes a lot of the pressure off, since you're like, look,

880
00:39:55,200 --> 00:39:57,840
Speaker 2: no matter what, like I'm getting to live my dream

881
00:39:57,880 --> 00:39:59,000
Speaker 2: and do something really fun.

882
00:39:59,480 --> 00:40:02,280
Speaker 1: So, out of the people, what did you do post

883
00:40:02,760 --> 00:40:04,480
Speaker 1: selling your company? And also I want to put this

884
00:40:04,520 --> 00:40:06,600
Speaker 1: in the perspective of like twenty year olds listening to

885
00:40:07,520 --> 00:40:09,480
Speaker 1: I know you said your life didn't change that much

886
00:40:09,520 --> 00:40:14,080
Speaker 1: after you sold the company, but in actuality, like you

887
00:40:14,160 --> 00:40:16,320
Speaker 1: do all of a sudden get this like big deposit

888
00:40:16,360 --> 00:40:18,200
Speaker 1: into your bank account. How does it work? Is it

889
00:40:18,239 --> 00:40:19,200
Speaker 1: like a wire transfer?

890
00:40:19,560 --> 00:40:22,040
Speaker 2: You get a really big wire transfer one day you

891
00:40:22,080 --> 00:40:25,319
Speaker 2: get and then you get smaller amounts one year later

892
00:40:25,320 --> 00:40:27,719
Speaker 2: and two year later. They always reserve some money in

893
00:40:27,760 --> 00:40:29,400
Speaker 2: case shit. Fox up where you can pay them back

894
00:40:29,480 --> 00:40:32,160
Speaker 2: or whatever, but yeah, I want big wire transfer. My

895
00:40:32,200 --> 00:40:34,040
Speaker 2: stories are very boring. Though I did nothing crazy. I

896
00:40:34,040 --> 00:40:37,040
Speaker 2: bought a secondhand car, which is insane. I didn't need

897
00:40:37,080 --> 00:40:39,080
Speaker 2: to buy a secondhand car, but I wanted to go

898
00:40:39,160 --> 00:40:41,200
Speaker 2: surfing at Rockaway Beach and I was like, oh, you

899
00:40:41,200 --> 00:40:42,880
Speaker 2: know what, I deserve a car, So I bought a

900
00:40:42,880 --> 00:40:46,759
Speaker 2: second hand car. I want to travel, but most of

901
00:40:46,800 --> 00:40:50,279
Speaker 2: the world was locked down. But I realized Tanzania was

902
00:40:50,280 --> 00:40:52,400
Speaker 2: in lockdown, so I went to climb Mount Kilimanjaro. I

903
00:40:52,440 --> 00:40:53,839
Speaker 2: was one of the first people to do that. Right

904
00:40:53,880 --> 00:40:58,520
Speaker 2: after And yeah, then, honestly, like a lot didn't change.

905
00:40:58,560 --> 00:41:00,600
Speaker 2: I bought a house. But even then it was like,

906
00:41:00,840 --> 00:41:04,200
Speaker 2: this had to be a good, responsible decision. But what

907
00:41:04,360 --> 00:41:07,560
Speaker 2: started changing a lot is once I wasn't doing my job.

908
00:41:07,920 --> 00:41:11,320
Speaker 2: That freedom let me spend two years travel the world,

909
00:41:12,000 --> 00:41:14,640
Speaker 2: spend more time with my family, you know, go hang

910
00:41:14,680 --> 00:41:16,400
Speaker 2: out with friends that not seen in a long time.

911
00:41:16,719 --> 00:41:18,840
Speaker 2: That I felt really was awesome.

912
00:41:18,680 --> 00:41:22,640
Speaker 1: Having made a lot of money. How was your perspective

913
00:41:23,120 --> 00:41:24,080
Speaker 1: changed on money?

914
00:41:24,280 --> 00:41:28,600
Speaker 2: I feel fortunate in that. I again, I've seen other

915
00:41:28,640 --> 00:41:32,200
Speaker 2: friends go through something similar where their burn rate or

916
00:41:32,239 --> 00:41:35,560
Speaker 2: whatever has linearly gone up. I definitely spend more money

917
00:41:35,600 --> 00:41:37,759
Speaker 2: now and I have more than enough for everything I do,

918
00:41:37,840 --> 00:41:41,319
Speaker 2: but it hasn't dramatically changed a lot of stuff, Like

919
00:41:41,400 --> 00:41:44,319
Speaker 2: some lifestyle changes are massive, are like I'll always like

920
00:41:44,560 --> 00:41:47,239
Speaker 2: get a life flat seat when I fly on a plane,

921
00:41:47,560 --> 00:41:51,520
Speaker 2: long flights or stuff like that. I can be more

922
00:41:51,520 --> 00:41:54,719
Speaker 2: generous with friends and family, so that's been awesome, but

923
00:41:54,800 --> 00:41:58,400
Speaker 2: it hasn't like dramatic, Like I don't find myself in

924
00:41:58,440 --> 00:42:01,040
Speaker 2: the pursuit of much more like I want to build

925
00:42:01,080 --> 00:42:02,719
Speaker 2: a really large company now and I want it to

926
00:42:02,719 --> 00:42:05,640
Speaker 2: be financially successful, but more because that's a way of

927
00:42:05,719 --> 00:42:09,560
Speaker 2: keeping score versus I think the like another fifty million

928
00:42:09,600 --> 00:42:11,920
Speaker 2: dollars will change my life. I think at this point,

929
00:42:12,160 --> 00:42:15,040
Speaker 2: as dark as it sounds, like, more money will just

930
00:42:15,120 --> 00:42:17,120
Speaker 2: change the number I go to the grave with. It

931
00:42:17,160 --> 00:42:20,840
Speaker 2: will not change much. I have. I have enough, basically,

932
00:42:20,920 --> 00:42:23,719
Speaker 2: like a lot of people ask is what is enough?

933
00:42:23,760 --> 00:42:26,480
Speaker 2: And I don't know. For me, it wasn't what I

934
00:42:26,520 --> 00:42:29,120
Speaker 2: had before the exit, and I'm definitely well passed it now,

935
00:42:29,160 --> 00:42:31,680
Speaker 2: so somewhere in between. But yeah, I definitely feel like

936
00:42:31,680 --> 00:42:32,239
Speaker 2: I have enough.

937
00:42:32,400 --> 00:42:35,400
Speaker 1: And then post building a successful company. How do you

938
00:42:35,400 --> 00:42:37,520
Speaker 1: think your perception on life has changed.

939
00:42:37,840 --> 00:42:40,359
Speaker 2: If I look at my life and think about what

940
00:42:40,440 --> 00:42:43,280
Speaker 2: is excited me motivated and make me made me happy,

941
00:42:43,360 --> 00:42:47,320
Speaker 2: it is like playing and winning sports games of different kind.

942
00:42:48,080 --> 00:42:51,960
Speaker 2: And as I even when it came time to start

943
00:42:51,960 --> 00:42:54,880
Speaker 2: my next business, part of the framing in my mind

944
00:42:54,960 --> 00:42:56,960
Speaker 2: is like look for better or worse. My sport now

945
00:42:57,040 --> 00:42:59,320
Speaker 2: is a little bit lamer than cricket. It's building a business.

946
00:42:59,760 --> 00:43:01,920
Speaker 2: And I'm still in the prime of my career and

947
00:43:01,960 --> 00:43:04,240
Speaker 2: I'm too young to kind of hang my boots or whatever.

948
00:43:05,360 --> 00:43:07,680
Speaker 2: But I still think like retaining that sense of like

949
00:43:07,800 --> 00:43:12,360
Speaker 2: adventure and competitiveness and you know, while keeping it lighthearted

950
00:43:12,960 --> 00:43:14,600
Speaker 2: is such a big part of who I am, and

951
00:43:14,640 --> 00:43:16,759
Speaker 2: it's something I think as you get older you have

952
00:43:16,800 --> 00:43:19,680
Speaker 2: to fight to retain, but I, you know, work towards that.

953
00:43:20,040 --> 00:43:23,359
Speaker 1: Let's talk about when you decided to start building your

954
00:43:23,400 --> 00:43:25,640
Speaker 1: next company carry which by the way, I'm technically an

955
00:43:25,680 --> 00:43:28,200
Speaker 1: investor in very small investor, but still counts.

956
00:43:28,320 --> 00:43:31,520
Speaker 2: Size doesn't count. You guys are investors, That's what's important.

957
00:43:32,320 --> 00:43:34,799
Speaker 2: It took about I would say between eighteen and twenty

958
00:43:34,800 --> 00:43:35,360
Speaker 2: four months.

959
00:43:35,480 --> 00:43:35,719
Speaker 1: Wow.

960
00:43:36,000 --> 00:43:38,279
Speaker 2: Before it was quick, it was.

961
00:43:38,280 --> 00:43:39,920
Speaker 1: It probably felt like a while though.

962
00:43:40,280 --> 00:43:42,480
Speaker 2: Time the benefit and this is also why I love

963
00:43:42,520 --> 00:43:44,520
Speaker 2: traveling so much. Is when you change your day to

964
00:43:44,560 --> 00:43:48,200
Speaker 2: day environment, time feels slower. So those eighteen months definitely

965
00:43:48,200 --> 00:43:50,879
Speaker 2: felt like things slowed down in a really good way.

966
00:43:51,400 --> 00:43:53,840
Speaker 2: But by the end of that I started to crave,

967
00:43:53,960 --> 00:43:56,960
Speaker 2: you know, building something with a group of like minded people,

968
00:43:57,440 --> 00:43:59,640
Speaker 2: the latter being very important. Like for me, the business

969
00:43:59,719 --> 00:44:00,960
Speaker 2: is a part part of it, but I wanted to

970
00:44:00,960 --> 00:44:03,960
Speaker 2: build a business with a group of people where we

971
00:44:04,160 --> 00:44:05,879
Speaker 2: like each other. You know, that was such a big

972
00:44:05,920 --> 00:44:08,520
Speaker 2: part of my life for almost seven or eight years.

973
00:44:08,800 --> 00:44:11,239
Speaker 2: I started to miss that and yeah, decided to it

974
00:44:11,320 --> 00:44:11,919
Speaker 2: all over again.

975
00:44:12,120 --> 00:44:17,640
Speaker 1: And when you started teachable it was and even till

976
00:44:17,640 --> 00:44:19,760
Speaker 1: the day you sold, it was such a simple idea.

977
00:44:20,680 --> 00:44:24,000
Speaker 1: What is this simple idea that Carrie has to offer?

978
00:44:24,400 --> 00:44:28,000
Speaker 2: The tax code in America is incredibly hard for the

979
00:44:28,120 --> 00:44:32,360
Speaker 2: average person to understand and take advantage of, and we

980
00:44:32,400 --> 00:44:34,759
Speaker 2: want to build software to just do that for you.

981
00:44:34,920 --> 00:44:37,160
Speaker 2: So today that manifests itself and we help people set

982
00:44:37,200 --> 00:44:41,440
Speaker 2: up retirement plans and do tax saving strategies. But really

983
00:44:41,520 --> 00:44:44,759
Speaker 2: the big north star is if we can help you,

984
00:44:45,080 --> 00:44:48,400
Speaker 2: every other person listening to this show take advantage of

985
00:44:48,480 --> 00:44:52,200
Speaker 2: all the opportunities that otherwise you'd need expensive lawyers and

986
00:44:52,239 --> 00:44:54,440
Speaker 2: accountants and a lot of time and paperwork to do.

987
00:44:54,719 --> 00:44:57,240
Speaker 1: So what does the platform like look like for people?

988
00:44:57,280 --> 00:44:57,360
Speaker 2: Like?

989
00:44:57,400 --> 00:44:58,240
Speaker 1: How does it help?

990
00:44:58,440 --> 00:45:00,319
Speaker 2: So today, we have a list of strategy that can

991
00:45:00,320 --> 00:45:02,560
Speaker 2: help most people save money. Like we have a one person,

992
00:45:02,600 --> 00:45:05,080
Speaker 2: four one K plan for anyone. As a business owner,

993
00:45:05,440 --> 00:45:08,080
Speaker 2: we have retirement accounts called iras that let you do

994
00:45:08,600 --> 00:45:10,759
Speaker 2: all kinds of you know, conversions. If you're a high owner,

995
00:45:10,800 --> 00:45:12,680
Speaker 2: we let people do something called the backdoor roth, the

996
00:45:12,719 --> 00:45:16,719
Speaker 2: megabackdoor oth. We have a cash management product that will

997
00:45:16,760 --> 00:45:20,200
Speaker 2: put your cash in the most tax advantage money market fund.

998
00:45:20,560 --> 00:45:22,560
Speaker 2: So think of it as a way where you come in.

999
00:45:22,640 --> 00:45:24,719
Speaker 2: You have a list of strategies, you can pick the

1000
00:45:24,760 --> 00:45:27,759
Speaker 2: ones you like, will custody your dollars, and at the

1001
00:45:27,880 --> 00:45:29,880
Speaker 2: end of the year, we can also file your taxes

1002
00:45:29,920 --> 00:45:32,319
Speaker 2: for you. Yeah, it's a fully different world. I underestimated

1003
00:45:32,320 --> 00:45:35,520
Speaker 2: how difficult the world of fintech and finances. But as

1004
00:45:35,520 --> 00:45:37,120
Speaker 2: I said, you know, like keeps it interesting.

1005
00:45:37,239 --> 00:45:39,640
Speaker 1: Yeah, definitely. How many people work at the company.

1006
00:45:39,320 --> 00:45:41,800
Speaker 2: Now, we're eighteen people right now? Wow?

1007
00:45:42,040 --> 00:45:44,279
Speaker 1: All right, so you got that startup culture going by

1008
00:45:44,320 --> 00:45:46,319
Speaker 1: the time you sold Teachable, how many people were working

1009
00:45:46,360 --> 00:45:47,279
Speaker 1: at the company.

1010
00:45:47,200 --> 00:45:48,960
Speaker 2: Almost two hundred, which I would say is about one

1011
00:45:49,040 --> 00:45:51,960
Speaker 2: hundred and fifty people more than what feels good from

1012
00:45:51,960 --> 00:45:54,920
Speaker 2: the perspective of, you know, truly feeling like a small startup.

1013
00:45:55,040 --> 00:45:57,880
Speaker 1: What are you doing differently this time that you wish

1014
00:45:57,920 --> 00:46:00,520
Speaker 1: you had known to do going into building Teachable.

1015
00:46:00,880 --> 00:46:04,560
Speaker 2: I will caveat with I still believe I'm going to

1016
00:46:04,640 --> 00:46:06,520
Speaker 2: make a whole new set of mistakes. I think doing

1017
00:46:06,560 --> 00:46:08,960
Speaker 2: something two times is a very very small sample size.

1018
00:46:09,320 --> 00:46:12,080
Speaker 2: But this time we're fighting even harder to keep the

1019
00:46:12,120 --> 00:46:15,600
Speaker 2: team as small as possible. At Teachable, we did, but

1020
00:46:15,719 --> 00:46:17,640
Speaker 2: now you know, eighteen people, we could probably be two

1021
00:46:17,680 --> 00:46:20,399
Speaker 2: to three times as many people. But I've just seen

1022
00:46:20,440 --> 00:46:24,520
Speaker 2: the effectiveness of small teams and that's a really, really

1023
00:46:24,560 --> 00:46:28,239
Speaker 2: big thing we're trying to do. We're also spending very

1024
00:46:28,239 --> 00:46:31,279
Speaker 2: little money on paid marketing. We're trying to build our

1025
00:46:31,360 --> 00:46:34,120
Speaker 2: business in a very lean way that we don't have

1026
00:46:34,200 --> 00:46:37,240
Speaker 2: to just because of seeing friends do the opposite playbook,

1027
00:46:37,239 --> 00:46:38,880
Speaker 2: where you raise a ton of money and you're spending

1028
00:46:38,880 --> 00:46:40,799
Speaker 2: a lot of money and then the whole train kind

1029
00:46:40,840 --> 00:46:41,600
Speaker 2: of runs away from you.

1030
00:46:41,680 --> 00:46:44,239
Speaker 1: Yeah, and there's nothing like a startup culture, and it's cool.

1031
00:46:44,320 --> 00:46:46,960
Speaker 1: Knowing that you love being in a startup environment, small

1032
00:46:47,000 --> 00:46:49,880
Speaker 1: team kind of comes into play with that. Well, we

1033
00:46:50,000 --> 00:46:51,960
Speaker 1: learned so much about you today. Thank you so much

1034
00:46:51,960 --> 00:46:53,959
Speaker 1: for sitting down with me. I've got one final question

1035
00:46:54,000 --> 00:46:56,480
Speaker 1: that I want to ask you. Knowing what you know now,

1036
00:46:57,040 --> 00:46:58,920
Speaker 1: what is one piece of advice you would give to

1037
00:46:58,960 --> 00:46:59,720
Speaker 1: your younger self.

1038
00:47:00,560 --> 00:47:03,880
Speaker 2: People overestimate risk, like I think one of the biggest

1039
00:47:03,960 --> 00:47:08,040
Speaker 2: biases we all have. It's very natural is risk feels

1040
00:47:08,080 --> 00:47:10,720
Speaker 2: like the scary thing, but as a result, our brain

1041
00:47:10,840 --> 00:47:14,279
Speaker 2: over indexes on the negative part of risk. I think

1042
00:47:14,280 --> 00:47:15,840
Speaker 2: it took a fair amount of risk. I think I

1043
00:47:15,840 --> 00:47:19,160
Speaker 2: could probably have taken two to four times more, and

1044
00:47:19,200 --> 00:47:21,040
Speaker 2: I think that's true for most people listening to this.

1045
00:47:21,320 --> 00:47:23,520
Speaker 1: Well, thank you so much. There's so much we can

1046
00:47:23,640 --> 00:47:25,719
Speaker 1: learn from you, for everybody that wants to follow you,

1047
00:47:25,840 --> 00:47:27,640
Speaker 1: stay up to date with your journey and everything you've

1048
00:47:27,680 --> 00:47:29,279
Speaker 1: got going on. Where can we find you?

1049
00:47:29,560 --> 00:47:32,360
Speaker 2: Yeah, I'm on social it's my full name on Twitter,

1050
00:47:32,440 --> 00:47:36,600
Speaker 2: it's my ankr NA on Instagram. Pretty active there otherwise,

1051
00:47:36,600 --> 00:47:37,880
Speaker 2: carries atcarry dot com.

1052
00:47:37,920 --> 00:47:39,960
Speaker 1: Thank you guys so much for listening to this week's

1053
00:47:39,960 --> 00:47:42,920
Speaker 1: episode of Post Run High with Encore. If you enjoyed

1054
00:47:42,920 --> 00:47:45,799
Speaker 1: this conversation. It would mean so much to me if

1055
00:47:45,840 --> 00:47:48,200
Speaker 1: you took a second to follow the show, rate it,

1056
00:47:48,360 --> 00:47:51,640
Speaker 1: review it. It really helps more people find post run

1057
00:47:51,719 --> 00:47:55,920
Speaker 1: High and it helps us continue bringing you inspiring conversations.

1058
00:47:56,080 --> 00:48:02,880
Speaker 1: I'll see you guys next week for another episode.