October 20, 2025 • 48 mins
In this inspiring conversation, Ankur Nagpal opens up about his multicultural upbringing, early love of cricket, and how moving to the U.S. at 17 shaped his entrepreneurial journey. From his first viral Facebook quizzes to founding and selling Teachable for $250M, Ankur shares practical lessons on grit, identity, and building something meaningful. He discusses how America’s culture of risk-taking enabled his success, why unscalable hustle matters, and what comes next after achieving financial freedom. A must-listen for anyone chasing creative or business dreams.
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Episode Transcript
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Speaker 1 (00:00):
Hi guys, it's your friend Kate Max and welcome back
to Post run High. We talk a lot about building
wealth and success, but not enough about what to actually
do once you have it. Today's guest has built and
sold a massive company, made real money, and then had
(00:21):
to figure out what comes next. Today's episode is with
encoren Adpaul. He's the founder of Teachable and someone my
husband Jeremy and I have known for a bit now
here in New York. The two of them play put
all together, and I've always had such great interactions with Encore,
so it was really fun to finally get a run
in together and then sit down to chat after Encore
grew up in Oman with Indian roots and came to
(00:44):
the US to study economics at UC Berkeley. While he
was there, he started building Facebook apps, yes, the kind
that tell you which friends character you are most like,
and before he knew it, those apps were making him
real money. That early entrepreneurial spark eventually led him to
found Teachable at just twenty four years old, which he
went on to sell for about two hundred and fifty
(01:06):
million dollars by the time he was thirty one. Since then,
Encore has seen every side of the founder journey, from
scrappy student projects to major exits investing, and now continuing
to build new businesses. But what I loved most about
this conversation isn't just Encore success. It's about how open
and transparent he is, about the mindset behind it all.
(01:26):
We talked about how his definition of success has evolved,
what freedom really looks like, and what his life is
like outside of work. I was also pleasantly surprised to
find out that he is quite the athlete himself, which
I semi knew from his pidel skills, but we dive
into that a bit at the start of our conversation.
All right, let's get into it. This is Encore on
(01:46):
Post Run High. Encore, welcome to Post Run High.
Speaker 2 (02:00):
Thank you. Excited to be here, even though I had
to run to get here.
Speaker 1 (02:02):
We ran a couple of blocks, and by that.
Speaker 2 (02:03):
You mean we ran twenty miles. Good pace, kept it going,
kept the conversation going. It was good. It was good.
I haven't been running a lot lately. I am supposed
on a marathon later this year, so maybe this was
my training run number one.
Speaker 1 (02:15):
Oh well, what's the farthest distance you've ever Ran.
Speaker 2 (02:18):
I did the Brooklyn Half two years ago.
Speaker 1 (02:20):
Okay, so you have never done a full marathon.
Speaker 2 (02:22):
Now iver done a full marathon. The Brooklyn Half I
got into because I'm a very competitive person and we
had a group chat with eight people, and all I
cared about was beating the other seven. You know, the
time didn't matter, did you I did? I did? I
barely edged it out. Because people always say running is
an individual sport. It doesn't matter how you do, it's
just about yourself. I didn't care about myself. I just
wanted to beat the others.
Speaker 1 (02:43):
What marathon are you doing Berlin?
Speaker 2 (02:46):
Wow?
Speaker 1 (02:47):
Jeremy's friends doing Berlin too?
Speaker 2 (02:48):
October thirtieth, September twenty second, something like that. Oh okay, yeah,
that should be fun. The big reason I'm doing it
is I've been prioritizing spending time with family a lot,
and my brother's really gotten into run, so it's a
little brother activity. So as a result I have to
actually do it.
Speaker 1 (03:04):
Well, that's going to be so fun. Are you guys
going to do October fast after? No?
Speaker 2 (03:08):
I have a team retreat right before, so Lisbon then
straight to Berlin. But yeah, I'm looking forward.
Speaker 1 (03:12):
Okay, what's your training looking like Recently?
Speaker 2 (03:15):
I keep myself pretty active, but most of it is
either playing sports or working out. Running is something that
as I get closer, I'll probably do one long run
a week or something, because again, it's not the primary
thing I'm optimizing for. My goal is, I don't know,
trying to do it in four hours and not die.
Speaker 1 (03:29):
The first time I did the New York City Marathon,
I ran it like right under four hours, and that
was my goal too, and I literally was doing no training,
Like I mean, I did a little bit of training,
but I was in college. I was a sophomore. I
was drinking going out.
Speaker 2 (03:41):
In that What was the longest run you had done
prior to that.
Speaker 1 (03:45):
It's funny because whenever you run a marathon, people will
say to you, training wise, you should get to like
a twenty or twenty two mile run. And I think
the farthest I had gone was like sixteen miles, and
I was like, oh, I'll be fine. And then the
first time I did the New York City Marathon, I
got to mile eighty, which is when you get into
the Bronx, and it was like raining that year, and
my legs were so fried to the point where I
(04:07):
had to stop, like I completely hit the wall. And
I had brought like an extra pair of socks for
some reason, and I was like this woman in the
Bronx helped me change my socks on the sideline, and
oh so.
Speaker 2 (04:17):
That's a beautiful New York story.
Speaker 1 (04:18):
Though beautiful New York story, I can tell you that
it was horrible. But I did still finish in under
four hours, and that was impressive. But I remember, my
older brother has a video of me running at mile
twenty four, and if you guys know the New York
City Marathon, you know exactly where mile twenty four is
in Central Park. And he posted it on his story
and I literally looked like I was walking, but in
(04:39):
my mind I was running, And I was like, Connor,
why would you post that? But you know what, still
did it.
Speaker 2 (04:46):
I hope there's an old German Man waiting for me
in mile twenty two with some socks.
Speaker 1 (04:49):
Yeah. Yeah, you're a padel guy. But on our run,
you were talking a little bit about cricket. So let's
talk about movement and how it looks in your life.
Speaker 2 (04:58):
Yeah, so now a lot of peop people know about
you know, all the work I do in tech. But
until age fourteen fifteen, my goal was to be a
professional cricketer. Like I spent pretty much every day from
age like five, six seven till fourteen fifteen thinking my
dream was to play cricket for a living. Wow, And
I got relatively far. I played internationally for the country
(05:20):
I grew up in, so I played for Oman at
the under seventeen Asian level. But cricket and Oman is
like cricket in America. You're very good in a small country,
and when we went to play against better kids in India,
were like, you're good, but not good enough to do
this for a living. But as a result, being competitive
physical movement has been such a big part of who
I am, and even now I feel like just playing
(05:42):
team sport is something that has shaped me quite a bit.
Speaker 1 (05:45):
Yeah, And I feel like when you grow up playing
team sports, it's so fun to like continue on in
your adult life being competitive and I like knowing that
you've picked up at all. But for people that don't know,
let's talk a little bit about cricket for a second.
Because I feel like I grew up I would be
at lacrosse tourns and I'm going to say, like kind
of over in like a baseball diamond type of setting.
(06:06):
I would occasionally see people playing.
Speaker 2 (06:08):
Cricket, people in the white and I.
Speaker 1 (06:12):
Never knew like what cricket was. I knew it was
similar to baseball, right yep, But like explain.
Speaker 2 (06:18):
Cricket to absolutely so think about it as a baseball
with two bases. People have this vision of like, oh,
cricket is played by old British men and wearing all whites,
and the games go on for five days. And while
that is the genesis of where the sport came from,
today's version is three or four hours, super quick, very competitive,
there's two bases. But at the same time I find
(06:41):
what I find powerful about it is that the team sport.
But at the same time it can be incredibly isolating.
When you're batting, you have eleven people around you cursing you,
yelling at you, calling your mom all kinds of names.
But as a result, it builds this mental resilience. You
have a person coming towards you hurling a fithysical object
which if it hits you can kill you. Right you
(07:02):
have protective gear. So it's this very physical, very mental
sport that played such a big part in my life
and if you move outside the US, it is actually
the second most followed sport in the world after soccer.
Speaker 1 (07:13):
Oh wow, I did not know that.
Speaker 2 (07:15):
It is insane. A big part of it is India, Pakistan,
Sri Lanka. These are big countries, but it is the
second most followed sport. Even when they held a game
in New York City last year they brought the World
Cup to the US, the cheapest tickets for games between
India and Pakistan in New York was fifteen hundred dollars,
which is pretty insane for a sport that's, you know,
completely Unamerican. It was almost as expensive to like watch
(07:38):
an NBA Finals as like a random cricket game in
New York.
Speaker 1 (07:42):
And you are still a big cricket fan.
Speaker 2 (07:44):
I'm a big cricket fan. Now it's more on watching
and I recently also decided to buy a stake in
a team, so it was like, I want to invest
in it. I haven't played as much since it's a
hard sport to play. You have to go up to
the Bronx, spend like a couple hours getting there, play
for eight hours, so it's a day.
Speaker 1 (08:00):
Yeah. They play in Van Cortland Park.
Speaker 2 (08:01):
They played Vancortland Park a game that before.
Speaker 1 (08:03):
Because when I went to Fordham, when I was a
freshman and a little bit of my sophomore year, I
lived at the rose Hill campus, and I decided my
sophomore year, I was like, let me just switch things
up a little bit on campus here, and I tried
out for the cross country team, where I guess I
walked on technically didn't try out.
Speaker 2 (08:18):
And yeah, this makes a marathon less impressive, but go on.
Speaker 1 (08:20):
Yeah, we used to always see the guys playing cricket
at Van Cortland.
Speaker 2 (08:23):
Yeah, it was such a big part of who I
am as a person and how I grew up. So
now deciding to buy a piece of a cricket team
was almost like me paying the eight year old version
of myself to kind of go back to what I
thought would be awesome as a kid. Yeah.
Speaker 1 (08:36):
I mean, your younger self is probably like that's pretty bad.
Speaker 2 (08:40):
Yeah exactly.
Speaker 1 (08:41):
Okay, Well, let's talk a little bit more about your childhood.
So you were born in India, but you didn't spend
the majority of your life in India, right, So like
paint the picture for us of what your childhood was
like where you grew up.
Speaker 2 (08:52):
And yeah, yeah, a little.
Speaker 1 (08:53):
Bit about it.
Speaker 2 (08:54):
So I grew up in Oman, in the Middle East
country that not a lot of people have heard of,
but it's a small country that also has a lot
of oil money. And my parents moved there in the
early eighties simply because the country discovered a lot of oil.
As Indian people, you would make twenty percent more money
by moving there, So they moved there. And honestly, I
spent the first seventeen years of my life there and
(09:15):
it was pretty ideal. My biggest regrets were it got
kind of boring by the time you get fifteen sixteen
and you're a little bit rebellious, you want to go out.
It's a pretty tame, quiet sort of place, so I
was itching to leave. But otherwise it was a very relaxed,
very sort of good childhood from what I can imagine.
Speaker 1 (09:33):
And we kind of touched on this on our run.
But you grew up almost shaped by three different cultures, right,
because that's seventeen. You ended up moving to the US
for school, but you have a little bit of like
your Indian background and then growing up in Oman. How
does Oman differ from growing up in India, Like, is
it totally different?
Speaker 2 (09:51):
Yeah, so Oman culturally so culturally, I mean we're Indian.
I'm I'm not a religious person, but born Hindu. Oman
is an Arab state. It's a Muslim country. Alcohol is
like somewhat prohibited. There's rules on what you can wear
and where you can go. Relative to the Middle East,
it's probably the most chill country, but it's still the
Middle East. So culturally, yes, we were from India, but
(10:12):
if I go back to India, I'd never quite fit
in there. Oman you're always a transient worker right at
the end of the day. We are expats. You have
no immigration status, no legal status. So while it's home
in a lot of ways, it's not home here. I
don't speak Arabic. I would imagine at this point, I've
been in the US a little bit over fifteen years.
America is probably my primary identity, but it's still very
(10:33):
different from someone born here or raised here. All of that.
Speaker 1 (10:36):
Do you feel like there's certain attributes from your childhood
in India and Oman that have translated into your life
here in the US.
Speaker 2 (10:45):
I think I'm so much better in this country than
back home. Why as an example, I by the end
was pretty bad at school back there, because school was
very regimented. You had to like study really hard. You
couldn't work the system. There's a lot of math and
science and if you weren't willing to put in the hours,
you wouldn't do very well. I came to the US
(11:05):
and I realized college here is like one big game.
You can figure out which classes to take, which classes
to actually show up for, how to get credits in
random ways. And I think the US society that's.
Speaker 1 (11:16):
Not making the US look great, Come on it.
Speaker 2 (11:18):
Does it does? I think this is why you have
entrepreneurship here, like the fact that you can come here
and take initiative and that is rewarded. Initiative is not
rewarded anywhere else. As an example, when I was here
as in Silicon Valley studying at the University of California, Berkeley,
I started a business in college that was making at
(11:39):
first twenty dollars a day, then a few hundred dollars
a day. And I was amazed by how many really smart,
impressive people were willing to meet with me, talk with me,
give me feedback. When I tried that back home in India,
they don't take you seriously as an eighteen year old.
The US and especially Silicon Valley is one of the
few places in the world that will take you very
(12:00):
seriously as a sixteen, seventeen, eighteen, nineteen year old. And
I think that's what makes this country very, very like
the best place to start something.
Speaker 1 (12:08):
Why do you think that doesn't exist as much in Oman.
Speaker 2 (12:12):
I think it's less that it doesn't exist in Oman specifically,
VERSUS America is just that special. And the reason for that,
I believe is you have two hundred years of selection bias,
where for two hundred years, the people that weren't happy
with where they lived moved here. Now you multiply that
sort of risk taking across many, many generations, And what
I think makes this country super unique is for hundreds
(12:34):
of years, smart enterprising people from across the world, across
the discipline have moved here to start a life, and
that really compounds over period of time.
Speaker 1 (12:45):
Yeah, it's incredible. When you were younger and you moved
here at seventeen, like, is that something that you knew
about the US that you were like, I want to
move to the US and go to college there because of.
Speaker 2 (12:54):
This, I wasn't frankly thinking that far ahead. But my
dad always in you like from the I think he
read a lot when he was younger, and he was
like from the age meeting thirteen or fourteen, he said,
look like at some point if you take your SAT
said no idea, what the SATs even war? And he
he's like, you have to go to the US since
you know, if you are entrepreneurial, you want to start something,
(13:17):
you want to build something incredible, There's no better place
for it. But that is the power of the American
brand where you have someone an Indian man living in
Oman had been to the US once convinced that his
children should come study in the US. And that's pretty cool.
Speaker 1 (13:34):
When you think about success in your childhood household, what
was the north star for you? And like, you know
what did your parents kind of instill in you guys?
Speaker 2 (13:45):
Yeah, so growing up, my parents are pretty liberal for
Indian parents, standards were very like, you know, do what
makes you happy. But I think my dad was always
biased that both me and my brother go out and
start her own thing. And I think a lot of
that came from the fact that he wanted to do that,
but for whatever reason, it felt like it wasn't responsible
of him too. I mean we were fine, we were
(14:07):
middle class, you know, potentially even upper middle class, but
it still felt too high risk for him to give
up a stable job to go do something. So in return,
he's like, Okay, I'll work really hard, I'll do this,
but but you and your brother should go ahead, and
you know, if you ever feel like it, go chase
your dreams, start your own thing. Don't feel like you
(14:27):
have to take the safe path. Since I did that
for you.
Speaker 1 (14:30):
I mean, your dad must be so proud of you
for what you've created before we get to everything that
you've built. Did your brother start his own company as well?
Speaker 2 (14:36):
No, my brother has had a bunch of side hustles,
but right now he's also very happy making a completely
different choice, and you know, working at a good job.
And honestly, I think his life is less stressful than mine.
Speaker 1 (14:47):
So and that's also really special because I know you
fly your parents in a decent bit right to the US,
and would you ever want them to move here? No?
Speaker 2 (14:54):
Their social lives are so popping, they have such a
great life, Like why would they give up their like crazy? Heck,
take social life to move to a new country. At
this age.
Speaker 1 (15:03):
Yeah.
Speaker 2 (15:04):
Yeah, Like I look at all my friends in New York.
Their lives are crazier than ours, Like they have parties
every night, they're happy.
Speaker 1 (15:21):
Well, what made you choose UC Berkeley.
Speaker 2 (15:23):
I got rejected from every better school than UC Berkeley.
It was very simple. I think I overshot my college applications.
I got rejected from every IVY League school. I got
rejected from. Stanford Berkeley was the best school I got into.
So it was very simple. In the US, you have
the luxury of visiting all your colleges and seeing which
one you connect the most with. For me, for most
(15:45):
Indian kids, it's like, Okay, what is the best school
I get into? Sure, I'll go there. And the first
time you're on campus is your first day of class.
Speaker 1 (15:52):
And you were seventeen, not eighteen, correct, So you were
a year younger than most of the kids.
Speaker 2 (15:55):
You're younger. I graduated at twenty, so I graduated before
I could legally have a drink.
Speaker 1 (16:00):
Well, UC Berkeley's a good place to land.
Speaker 2 (16:02):
It was a good place to land. It was a
little bit different from what I was expecting. This sounds
really dumb and corny, but at the time, you know,
A big part of what you learn about America is
like movies and TV and stuff and as yeah, food
and as embarrassing as it sounds. I go to college
and in my mind, I'm like, Oh, this is going
to be like American Pie. This is going to be
(16:24):
like frat parties and red solo cups and just people
doing crazy things. But it was a pretty dorky engineering school.
Like the first day I get there, half our floor
is just playing video games, like no one wants to
socialize or doing their own thing, And I was like,
this is not the US college experience I was promised.
But being on the West Coast and stuff was pretty
(16:45):
helpful and it helped me meet a lot of great people.
Speaker 1 (16:48):
During that transition process. When you first moved here, was
the transition hard? Did you feel like? You know? What
was that like? For you?
Speaker 2 (16:56):
It was easier than you would imagine. And I think
there's a couple of reasons for that. I think one,
seventeen is early enough where your own identity is malleable,
you can change quite a bit. So a lot of
my friends who moved to the US at seventeen culturally
changed quite a bit. The ones who moved to twenty one, right,
four years. Those four years make a massive difference. The
(17:18):
second thing is the US is relatively easy to move
to compared to most of the world. I had a
hot take that I got canceled for online for saying
where I said America was the least racist country in
the world. And I genuinely like two years before that,
I'd studied in an all boys school in Australia and
that was a truly hard experience of trying to adjust
(17:39):
assimilate going to like a US college campus. I think
it's one of the friendliest places you can go, no
matter where you're from.
Speaker 1 (17:45):
What would your advice be for other students like you
transitioning into a school in the US and kind of
being in the US almost for the first time.
Speaker 2 (17:57):
The mistake I see a lot of people make, or
at least I think it's a mistake, is Indian kids
will come and hang out with the other Indian students
Chinese because we'll hang out the other Chinese students, and
I think, yes, you can have one friend group from there,
but you know you're starting a new life, like assimilate
and meet people from everywhere versus sticking to your own
kind or whatever.
Speaker 1 (18:17):
Yeah, and I feel like you having left India at
such a young age and growing up in Oman and
then moving to the US like having those kind of.
Speaker 2 (18:23):
Currect I already didn't have a single group I could
go with where I'm like, we're exactly alike.
Speaker 1 (18:29):
Yeah, that must That probably helps so much more than like,
you know, you ever really thought. Okay, well, let's talk
about your experience at UC Berkeley, because it was transformative.
I want to dive into the Facebook apps, so paint
the picture for us. What were you like as a
freshman you're student, and when did you first start becoming
entrepreneurial on your own?
Speaker 2 (18:49):
Yeah? So freshman year, I I mean I still personality
wise was the same. I spent all my time trying
to figure out, you know, how could I get good
grades while being the least amount of work. Yet I
always had this guilt that my parents were spending a
huge part of their life savings to send me to college. Right,
So there's a guilt kind of wing on me. So
(19:09):
I would always go to class and be pretty responsible.
I got a campus job my second semester. I got
an internship at Amazon after my freshman year, which at
the time I was like, Wow, this is like sick.
I was eighteen earning five grand a month. There's a
lot of money back then, still a lot of money.
It's still a lot of money.
Speaker 1 (19:28):
Everybody that I was making when I first graduated college,
I'm pretty sure.
Speaker 2 (19:31):
Yeah, yeah. And I was an intern and I moved
to a Seattle to intern at Amazon as an eighteen
year old, and for the first time in my life,
I felt positively miserable in Seattle. I was super homesick
because it was the first summer back. All my friends
were back home. I had this like, I don't know
if other people have felt this, but your first adult
job kind of sucks. Like you realize you go to
(19:52):
the office, you're there for so long, you come back,
you're kind of tired, and if you do it all
over again. I was eighteen. I didn't know anyone in
Seattle who was the same age as me. I didn't
have a fake idea, so I couldn't even go out
to places. But the upside of that is it coincided
with the launch of the Facebook platform, where you could
(20:12):
create little games and quizzes on Facebook, and having nothing
else to do on nights and weekends, I started to
play around with that, and by the end of that
summer got to a point of making you know, ten
or twenty dollars per day. And I have never had
a job since that Amazon internship. It also just made
me realize having a large job is so soul crushing.
There was a time, firstly, my entire team at Amazon
(20:35):
worked on such a small thing. My entire team worked
on one page inside one dashboard. And there were a
couple of days where I didn't go into the office
and no one even realized how horrible is that that,
like you matter so little? Like I was such an
annoyance for my boss that he didn't care if I
showed up or didn't.
Speaker 1 (20:53):
Yeah, Like, when you take a really entrepreneurial kid that
loves building things and working for yourself, and you know, yeah,
just you love building things, like and then you put
them in a nine to five job, you really are
like a cog in the system, a CS job at Amazon.
I mean, that's just not the right place for me.
Speaker 2 (21:10):
I wouldn't hire myself. As someone that hires a lot
of people, I would absolutely not hire myself.
Speaker 1 (21:14):
Yeah, well, of course not. You don't want somebody that
you know wants to start their own thing or your company.
Let's talk about building the Facebook apps, and you know
what Facebook kind of looked like at the time, and
how you guys started making money from it.
Speaker 2 (21:27):
Yeah, absolutely so back in the day. I mean, now
Facebook is the old person platform, but back then it
was the place to be right our first few years
of college, everything was shaped by it. When my freshman
year of college, Facebook was for college is only I
think by my sophomore year that expanded to other high
schools and stuff. But it was growing really fast. It
was a hotbed of activity, and they allowed anyone to
(21:48):
build an application on the platform, and as a result,
you could build something and potentially have millions of users
within the span of a few days. It was quite
unlike anything we've seen seen up until that point on
the Internet, where if you had to reach millions of people,
it was super difficult. But I spent the next three
years in college building all kinds of games and quizzes
(22:09):
and these hyper viral apps that would reach millions and
millions of people. So things like personality quizzes or somewhat
would answer five questions. It would tell them how good
a lover they are, just like stupid stuff.
Speaker 1 (22:20):
Like that, how are you coming up with the ideas
for the quizzes?
Speaker 2 (22:23):
So initially I would try and do a lot of
research work quite hard. Then I realized it doesn't matter
as long as you write good enough descriptions, like we
had a quiz called what color is your Aura? And
as long as the descriptions were good where it's reads
like a horoscope, where it's like, you know you're the
color of your aura is black, Kate, You're mysterious. People
think they know the real you, but they don't know
(22:44):
who's actually behind it all. And as long as you
kind of gave people what they wanted to share, that's
what really mattered. If we had a quiz, which friend's
character are you, people didn't care what character they are.
They would take the quiz over and over till they
got the care they wanted and they would share that.
So it was fascinating you get such a cool insight
(23:05):
into human psychology with millions of people.
Speaker 1 (23:08):
How much money were you making from these quizzes?
Speaker 2 (23:10):
So by the time I turned twenty one, I hit
a million dollars through this. It started out with ten
or twenty bucks a day. It peaked at tens of
thousands of dollars a day. I think our biggest day
was like fifty grand a day. But it was up
and down, right, You'd be very popular for like six days,
then would die down entirely.
Speaker 1 (23:30):
And when you say our, you basically are saying that
you went from doing this on your own late nights
after your internship at Amazon summer of your freshman year
to then what recruiting people at Burris recreated all my roommates.
Speaker 2 (23:42):
My head like, and this is so different, right, you like,
it's doing business when you don't know anything about business.
Anyone I recruited, I'm like, okay, fine, you do this,
you get thirty percent of revenue. You do this, you
get twenty percent. It was the craziest deals that didn't
make any sense, but it was really fun. Like we
I lived with three people who ended up and still
are amongst my closest friends. Brought them in on the business,
(24:02):
hired developers. It was a good crash course in building
a business before I even turned twenty one.
Speaker 1 (24:07):
What do you think the Facebook quiz has taught you
about business that was applicable to you, know your future
businesses like teachable and what you're doing now.
Speaker 2 (24:16):
I think it taught me about growth specifically, like that
entire platform was a time when you had to do
so much social engineering to grow anything. And I think
a lot of those lessons have stayed with me today
even now. I've never had as many people use anything
I've built since then. Like back in the day, we
peaked at about two to three million people a day.
(24:37):
There was a time where we had more traffic than
the New York Times, more traffic than LinkedIn. It was crazy,
and you know it was from a dorm room, so insane, so.
Speaker 1 (24:47):
Nuts, And did you guys continue doing it throughout college? Like?
How long did this last for?
Speaker 2 (24:54):
I did it till about a year or so after college.
It would always ebb and flow since you at shutdown
or the rules would change or the applications get less popular.
But after like this fifth or sixth time shutdown, I
started to feel like I wanted to build something more substantial,
because as cool as this was, you were only as
(25:14):
good as yesterday's revenue. You were building no enterprise value.
But also at a certain point, games and quizes are fun,
but you look back and you're like, am I truly
making people's lives better? Yeah.
Speaker 1 (25:25):
And also if you like think about it in like
the lifespan that you're saying for the games, you wanted
to building that with something that was sustainable. Did any
of the people that helped you build out these apps
on Facebook end up working at teachable?
Speaker 2 (25:41):
No. Two of them are finance bros. And ones of
plastic surgeons. I went in completely different worlds.
Speaker 1 (25:45):
Wow, Okay, so it really was a sideholso for you
as in college. Then what happened after college? Where did
you start working?
Speaker 2 (25:51):
After college? I had the two years, i would say,
of trying different ideas and nothing quite clicks. I probably
tried twelve or fourteen different startups. And at the time
that was also when I decided to it wasn't working
and pack my bags and move to New York City
and try to almost start over. And that was the
time I think my parents' faith was tested a little
(26:12):
bit because there was a divergence in what my mom
and dad wanted. My dad's like, yeah, keep going, it
doesn't matter, like who cares this, You'll figure it out.
My mom's like, well, why don't you work at Facebook?
You know they could hire you. Can't someone hire you?
But I'm glad I stuck it out until then starting
teachable when I was twenty four.
Speaker 1 (26:30):
I love knowing how supportive your parents were.
Speaker 2 (26:32):
They were and continue to be incredibly supportive, like they.
Speaker 1 (26:34):
Just always knew that you were going to make it
happen on your own, my.
Speaker 2 (26:37):
Dad more so than my mom. But yeah, I did.
It did work out. Through this whole process, immigration was
a stressor because I had a student visa. I sponsored
my own student visa. I then extended it, and then
at one point, which is around the time right before
moving to New York City, I had to leave the country.
I was told I had to leave the country, so
I googled the cheapest community college I could find get
(27:00):
another student visa. But I constantly had this sort of
stress of I can't legally stay here unless I figure
this immigration stuff out. So that does make things a
lot harder.
Speaker 1 (27:10):
How did you finally figure it out?
Speaker 2 (27:12):
I finally got a very good lawyer, and I applied
for something called the one visa, which is an extraordinary
ability visa, but it's something that the alien of extraordinary
alien exactly. It's very welcoming visa. But from there I
got my green card and eventually passport.
Speaker 1 (27:26):
Wow. And then by building your business here does that
help with immigration?
Speaker 2 (27:29):
So I only started Teachable when I figured out immigration.
It was got challenging enough that as soon as I
got that, I formally incorporated Teachable.
Speaker 1 (27:37):
Well, let's talk about how the idea for teachable came
to be, and I want to premise this with guys
when Encore was thirty one. He started it at twenty
four and by thirty one he sold Teachable for two
hundred and fifty million dollars, which is incredible. But let's
start with the basics. How did you guys get the
idea for teachable? And you know what did it start
out as? And then kind of what did it evolve into?
Speaker 2 (27:59):
Yeah, absolute, So it was never a big grand vision
or a grand idea. It was one of many different
side hustles or things we were trying. Where my buddy
Conrad and I we started. We saw this platform you
to Me, had come out where you could sell online courses,
so we decided to help some people sell their courses.
We soon realized why don't we create our own courses,
(28:19):
did that and then found a lot of challenges with
the you to me model where it was a marketplace.
They kept a really high revenue share. They owned the customer.
So I built the first version of Teachable almost as
a side project for my buddy Conrad, and we sold
a couple thousand dollars of courses when we launched, and
was like, okay, maybe there's a real idea here, and
(28:41):
then started offering it to other people.
Speaker 1 (28:43):
And when you say you were selling courses, like were
you having other people create the courses?
Speaker 2 (28:48):
So it started with other people, and then we said,
why don't we create our own courses. We had courses
on the whatever I did with the Facebook apps, growth marketing,
all of that.
Speaker 1 (28:56):
It's so interesting. And it started as like it was
almost like a social media platform.
Speaker 2 (29:00):
Right, yeah, I was super unintentional. It was. It was
always selling courses in your own websites. The product didn't
change much. But this is before the creator economy, right.
We didn't know Instagram, YouTube, everything would blow up. They'd
be all these big creators. We thought our target audience
was educators, so we got that frong. But as we
kept building the business, you know, the creator economy happened
(29:20):
and people started selling millions and eventually hundreds of millions
of dollars a year of courses.
Speaker 1 (29:25):
When did you guys realize that the company was going
from a startup to a real business.
Speaker 2 (29:31):
Probably so we It took us six months of just
messing around before I decided to incorporate and raise money.
I would say about a year after that it started
to feel like we started to make tens of thousands
of dollars a month. And at that point it's like
we maybe on we may be onto something, You may be.
Speaker 1 (29:47):
Onto something, and you're like, we need to make sure
we have the right team here. Let's talk a little
bit about hiring people, because I think that is one
of the hardest things for entrepreneurs, right, Like, what was
your hiring strategy when you guys really started growing tea?
Speaker 2 (30:00):
Initially it was one hundred percent vibes Like I wish
I could say. We had an interview process our first
our first engineer who became our CTO. He showed up
like an hour late to the interview, and either way,
we had a good chat. I described like one thing
I was working on chat kind of I kind of
forget about it. The next morning he emails me at
like six am. He stayed up all night building a
(30:23):
working prototype of what I was talking to him about
I'm like, cool, you're hired. We'll figure out the details later.
Speaker 1 (30:28):
Okay, that is more than vibes.
Speaker 2 (30:29):
Hiring people on where they went to school or where
they worked has turned out to be one of the
worst strategies I've found. Indexing a lot on people who
want to be there. I also index a lot in
people who move fast for better or worse. My operating
style is quite fast, and sometimes it is chaotic. It's
not easy for other people to keep up with. But
I like that from the people I hire.
Speaker 1 (30:48):
I've interviewed a lot of people like yourself that have
had this extreme level of success, and one of the
things that I've found with the most successful people is
that they're so quick to respond.
Speaker 2 (30:58):
Like is that a common out of it's a commonality.
I also bet if I were to hypothesize, there's a
high correlation with ADD like better or worse. I mean,
I'm not medicated add but you know, I think if
I grew up in America, I may have been. But
where you either reply right away or you're going to
forget about it. So the ones the people who do
reply are the ones who reply pretty quickly. But yeah,
there's a just a bias towards action, right, I don't
(31:21):
like kind of waiting around on stuff. I'm also very
instinctive when it comes to making decisions, So I think
that tends to help. If I think about all the
things that have made me good at what I do
and successful, those traits have a negative expression as well,
and I think that's a great example where we can't
take the good parts of our personality without also getting
the bad part of the exact same trait. So, yes,
(31:42):
I'm also impulsive. I probably take too many risks, But
if not for that, I would not have gotten the
positive expressions of that.
Speaker 1 (31:48):
When you guys first started out, what were the core
focuses for you when you were building your business? Like,
I know some of the things for you guys were
keeping outs bend low. You built a lot of your
moment off of organic growth, right, So like, let's talk
through those kinds of decisions and what made you guys.
Speaker 2 (32:05):
Yeah, absolutely, I would say there's basically three phases of
our growth. Phase one was just unmitigated kind of stupid
hustle where we would do insane, unscalable things to make
the numbers go up no matter what.
Speaker 1 (32:19):
Like what I give us some EXAMPCE.
Speaker 2 (32:20):
So there was a time when there's this guy which
had we wanted to sign up on our platform. His
name was Pat Flynn. He was a very big deal
in the world of online courses. Then Pat kind of
was ignoring all my emails. So I started looking at
every single conference he was going to, and anytime I
go to a conference, I'm like, hey, Pat, I'm going
to be here. Finally he once I saw he was
going to be at this conference called fin Conn in
(32:41):
North Carolina somewhere. I hit up Pat. I'm like, hey, Pat,
I'm going to be at fin Conn. He's like, cool,
I'll meet you for breakfast eight thirty tomorrow. I gotta
get there now tonight. So flew there. Obviously I didn't
have a conference ticket. I wasn't going to the conference,
met him for breakfast, signed him as a customer. He
became an affiliate. I flew back after that meeting. It
was stuff like that we did repeatedly, Like we had
(33:02):
a month where our customers weren't selling a lot, or
we had sorry the next month, we didn't have any
big course launches. So Conrad and I gave up our
Thanksgiving plans flew to Berlin with our biggest creators, took
a camera, recorded something, launched it the week after. So
we just had to do these things in the early
days before there was an engine that really worked.
Speaker 1 (33:25):
Yeah, no, it makes sense because it's like, you guys
have this platform that's built on courses, but you literally
need to find people, Like it can't just be you
guys making courses forever, like it has to be other
people as well. What were your other strategies to getting
people on Who was like the first person that you
guys got onto your platform.
Speaker 2 (33:41):
So the first big person so we got the first
person was obviously Conrad. The first couple of people were
other unim ME creators. But something pretty fortunate happened where
two of our creators made a million dollars in the
first six months, and the benefit of that is so
much pr right now. It's like John and Elliott are
twenty seven and twenty eight traveling the world, made a
million dollars teaching people how to build iPhone apps. So
(34:03):
then that got us the first sort of growth spurt,
and that's what led to our primary growth strategy that
we ran for most of the company, which was storytelling
about other creators. We realized our competitive advantage is the
best creators on our platform, especially if they were in
the world of business or making money online, they in
turn could be our biggest affiliates in promoters. So that's
(34:26):
the strategy we used for the next three or four years.
Speaker 1 (34:28):
Yeah, it makes so much sense.
Speaker 2 (34:29):
It's like, now it's obvious. At the time it felt
like crazy, but now it's you look at these businesses.
Speaker 1 (34:34):
Oh yeah, it's so true because it's like when you
think about I mean, when I think about YouTube, I'm like,
why do I want to be on YouTube? I'm like,
because so many of these other creators have had so
much success on YouTube, of course I want to like
try to have success on that app as well. It
makes the same It's kind of just something for Teachable,
and I think that's a cool notion to go into too,
because when you guys first started out, it was pretty
early on into the creator economy per se.
Speaker 2 (34:56):
There was no creator economy. We stumbled into it, basically.
Speaker 1 (34:58):
Literally stumbled into it. Like what did you learn about
the creator economy from building Teachable?
Speaker 2 (35:04):
It was fascinating since again there was no such thing
as the creator economy. But then we started to look around.
We're like, where can we find people that could be creators.
An insight that seems obvious now is we realize it's
easier to teach someone with an audience how to teach
than it is to teach a teacher how to build
an audience. The other thing is, I think we got
fortunate in timing, like we rode the wave of when
(35:28):
online courses were really big. Like I think the heyday
of courses were sort of twenty seventeen, almost peaking in
twenty twenty, and they've sort of declined a little bit.
I still think the creator economy is and will continue
to be massive, but the exact products will keep changing.
Speaker 1 (35:52):
How soon into you guys creating Teachable did things like
master Class come out.
Speaker 2 (35:56):
I would say roughly midway through they were out. But
they were always different variants. When we started, for instance,
skill share was really big and then they kind of,
you know, disappeared. There's a company called Creative Live. There
were always different form factors. What we got fortunate on
is by empowering the creator. We were very close to
Shopify but for information, but that meant the creator did
(36:18):
all the distribution. We were just the technology platform.
Speaker 1 (36:20):
It would have been cool if there was, like I
don't know if there was like a teachable Times master
class type of thing, because you would, like they're very different.
Speaker 2 (36:26):
We did. We did a few deals like that where
we'd help people create content, and what we soon found
is those businesses are hard enough that anytime we did that,
it turned into a shit show we were not prepared
for because you start doing something that's not your business,
and it's just a constant reminder that you have to
be better at saying no to things.
Speaker 1 (36:45):
Yeah. Absolutely, well. When I think about Masterclass two, I
almost think of like it's like a mini TV show, right,
Like it's like a mini TV series.
Speaker 2 (36:52):
So master Class. The problem Masterclass is like, the best
teachers we find are not the celebrities, right. The best
teachers are someone whose story you relate to. Like I
don't want to learn how to shoot a basketball from
Steph Currery. I want to learn from the other Indian
kid who's probably better than me, right, And people want
that relatability and Masterclass you right, it's entertainment less of education.
Speaker 1 (37:12):
What was it like selling a company during COVID.
Speaker 2 (37:14):
It was wild? I mean, you have nothing to compare
it to at all, but it was at the same
time it felt like a weight off my back. Yet
it was also hard. Right, you've been building this thing,
you care so much about this thing, and now it's
someone else's thing. What made it even more interesting slash
complicated is right the day after we sold it to
(37:36):
three months later, the business doubled. We saw more growth,
more like it was. The craziest times at work were
right after we sold, which honesty was probably good because
there was so much else happening in New York. New
York was a terrifying place of the time that it
kept us busy, but it never the realization almost never
sank in since you were so caught up in the day.
Speaker 1 (37:56):
To day, you ended up still working on it for
the next for a few months. Was selling, right, So
let's talk about what those months kind of looked like,
and how your position at the company changed after selling it,
and maybe what those emotions are like once you sell
a company.
Speaker 2 (38:08):
Yeah, so the emotions again, as I said, it's very
different because we were all in lockdown. There was no
cathartic like post exit party. I still get people from
the company who tell me that I owe them that
they're like, we never got to celebrate, like we all
to post sort of exit party. So it was it
was definitely a little bit more complicated since you're in
lockdown and kind of coming to grips with all of that.
(38:30):
For me, my life only really changed when I stepped
away from the role entirely, Like my life did not
feel different just having more money in the bank or whatever.
And by the end, and this also related to why
I sold the company, I don't think I was enjoying
it that much. The reason being, I felt like a
lot of my role was typical CEO stuff, which is
(38:51):
so much less fun than building and creating things, where
I had to deal with executives who had managers who
had other reports, and you spend all your life in
these long meetings every day, and it felt like it
was going nowhere. But when I stepped back is when
I really found the quality of my life improved.
Speaker 1 (39:09):
What is your role now? I care?
Speaker 2 (39:10):
Right right now, I am also the CEO, But when
you're a small company, I don't think it's really a CEO.
I think you only really become a CEO in a
true executive way when you have fifty hundred people and
if I feel the same way in the future, I'll
step away and bring in someone more qualified.
Speaker 1 (39:25):
What do you think is your favorite thing about building
a business?
Speaker 2 (39:28):
The people? Undoubtedly, like I look back on all the times.
Yes we made money, Yes we built a successful business,
but it's always the relationships. It's the team. So many
of the customers are still friends, our earliest investors. These
are lifelong relationships that compound and grow. I also think
(39:49):
having a good time while you're doing the whole thing
takes a lot of the pressure off, since you're like, look,
no matter what, like I'm getting to live my dream
and do something really fun.
Speaker 1 (39:59):
So, out of the people, what did you do post
selling your company? And also I want to put this
in the perspective of like twenty year olds listening to
I know you said your life didn't change that much
after you sold the company, but in actuality, like you
do all of a sudden get this like big deposit
into your bank account. How does it work? Is it
like a wire transfer?
Speaker 2 (40:19):
You get a really big wire transfer one day you
get and then you get smaller amounts one year later
and two year later. They always reserve some money in
case shit. Fox up where you can pay them back
or whatever, but yeah, I want big wire transfer. My
stories are very boring. Though I did nothing crazy. I
bought a secondhand car, which is insane. I didn't need
to buy a secondhand car, but I wanted to go
surfing at Rockaway Beach and I was like, oh, you
(40:41):
know what, I deserve a car, So I bought a
second hand car. I want to travel, but most of
the world was locked down. But I realized Tanzania was
in lockdown, so I went to climb Mount Kilimanjaro. I
was one of the first people to do that. Right
after And yeah, then, honestly, like a lot didn't change.
I bought a house. But even then it was like,
this had to be a good, responsible decision. But what
(41:04):
started changing a lot is once I wasn't doing my job.
That freedom let me spend two years travel the world,
spend more time with my family, you know, go hang
out with friends that not seen in a long time.
That I felt really was awesome.
Speaker 1 (41:18):
Having made a lot of money. How was your perspective
changed on money?
Speaker 2 (41:24):
I feel fortunate in that. I again, I've seen other
friends go through something similar where their burn rate or
whatever has linearly gone up. I definitely spend more money
now and I have more than enough for everything I do,
but it hasn't dramatically changed a lot of stuff, Like
some lifestyle changes are massive, are like I'll always like
(41:44):
get a life flat seat when I fly on a plane,
long flights or stuff like that. I can be more
generous with friends and family, so that's been awesome, but
it hasn't like dramatic, Like I don't find myself in
the pursuit of much more like I want to build
a really large company now and I want it to
be financially successful, but more because that's a way of
(42:05):
keeping score versus I think the like another fifty million
dollars will change my life. I think at this point,
as dark as it sounds, like, more money will just
change the number I go to the grave with. It
will not change much. I have. I have enough, basically,
like a lot of people ask is what is enough?
And I don't know. For me, it wasn't what I
(42:26):
had before the exit, and I'm definitely well passed it now,
so somewhere in between. But yeah, I definitely feel like
I have enough.
Speaker 1 (42:32):
And then post building a successful company. How do you
think your perception on life has changed.
Speaker 2 (42:37):
If I look at my life and think about what
is excited me motivated and make me made me happy,
it is like playing and winning sports games of different kind.
And as I even when it came time to start
my next business, part of the framing in my mind
is like look for better or worse. My sport now
is a little bit lamer than cricket. It's building a business.
(42:59):
And I'm still in the prime of my career and
I'm too young to kind of hang my boots or whatever.
But I still think like retaining that sense of like
adventure and competitiveness and you know, while keeping it lighthearted
is such a big part of who I am, and
it's something I think as you get older you have
to fight to retain, but I, you know, work towards that.
Speaker 1 (43:20):
Let's talk about when you decided to start building your
next company carry which by the way, I'm technically an
investor in very small investor, but still counts.
Speaker 2 (43:28):
Size doesn't count. You guys are investors, That's what's important.
It took about I would say between eighteen and twenty
four months.
Speaker 1 (43:35):
Wow.
Speaker 2 (43:36):
Before it was quick, it was.
Speaker 1 (43:38):
It probably felt like a while though.
Speaker 2 (43:40):
Time the benefit and this is also why I love
traveling so much. Is when you change your day to
day environment, time feels slower. So those eighteen months definitely
felt like things slowed down in a really good way.
But by the end of that I started to crave,
you know, building something with a group of like minded people,
the latter being very important. Like for me, the business
is a part part of it, but I wanted to
(44:00):
build a business with a group of people where we
like each other. You know, that was such a big
part of my life for almost seven or eight years.
I started to miss that and yeah, decided to it
all over again.
Speaker 1 (44:12):
And when you started teachable it was and even till
the day you sold, it was such a simple idea.
What is this simple idea that Carrie has to offer?
Speaker 2 (44:24):
The tax code in America is incredibly hard for the
average person to understand and take advantage of, and we
want to build software to just do that for you.
So today that manifests itself and we help people set
up retirement plans and do tax saving strategies. But really
the big north star is if we can help you,
(44:45):
every other person listening to this show take advantage of
all the opportunities that otherwise you'd need expensive lawyers and
accountants and a lot of time and paperwork to do.
Speaker 1 (44:54):
So what does the platform like look like for people?
Speaker 2 (44:57):
Like?
Speaker 1 (44:57):
How does it help?
Speaker 2 (44:58):
So today, we have a list of strategy that can
help most people save money. Like we have a one person,
four one K plan for anyone. As a business owner,
we have retirement accounts called iras that let you do
all kinds of you know, conversions. If you're a high owner,
we let people do something called the backdoor roth, the
megabackdoor oth. We have a cash management product that will
put your cash in the most tax advantage money market fund.
(45:20):
So think of it as a way where you come in.
You have a list of strategies, you can pick the
ones you like, will custody your dollars, and at the
end of the year, we can also file your taxes
for you. Yeah, it's a fully different world. I underestimated
how difficult the world of fintech and finances. But as
I said, you know, like keeps it interesting.
Speaker 1 (45:37):
Yeah, definitely. How many people work at the company.
Speaker 2 (45:39):
Now, we're eighteen people right now? Wow?
Speaker 1 (45:42):
All right, so you got that startup culture going by
the time you sold Teachable, how many people were working
at the company.
Speaker 2 (45:47):
Almost two hundred, which I would say is about one
hundred and fifty people more than what feels good from
the perspective of, you know, truly feeling like a small startup.
Speaker 1 (45:55):
What are you doing differently this time that you wish
you had known to do going into building Teachable.
Speaker 2 (46:00):
I will caveat with I still believe I'm going to
make a whole new set of mistakes. I think doing
something two times is a very very small sample size.
But this time we're fighting even harder to keep the
team as small as possible. At Teachable, we did, but
now you know, eighteen people, we could probably be two
to three times as many people. But I've just seen
the effectiveness of small teams and that's a really, really
(46:24):
big thing we're trying to do. We're also spending very
little money on paid marketing. We're trying to build our
business in a very lean way that we don't have
to just because of seeing friends do the opposite playbook,
where you raise a ton of money and you're spending
a lot of money and then the whole train kind
of runs away from you.
Speaker 1 (46:41):
Yeah, and there's nothing like a startup culture, and it's cool.
Knowing that you love being in a startup environment, small
team kind of comes into play with that. Well, we
learned so much about you today. Thank you so much
for sitting down with me. I've got one final question
that I want to ask you. Knowing what you know now,
what is one piece of advice you would give to
your younger self.
Speaker 2 (47:00):
People overestimate risk, like I think one of the biggest
biases we all have. It's very natural is risk feels
like the scary thing, but as a result, our brain
over indexes on the negative part of risk. I think
it took a fair amount of risk. I think I
could probably have taken two to four times more, and
I think that's true for most people listening to this.
Speaker 1 (47:21):
Well, thank you so much. There's so much we can
learn from you, for everybody that wants to follow you,
stay up to date with your journey and everything you've
got going on. Where can we find you?
Speaker 2 (47:29):
Yeah, I'm on social it's my full name on Twitter,
it's my ankr NA on Instagram. Pretty active there otherwise,
carries atcarry dot com.
Speaker 1 (47:37):
Thank you guys so much for listening to this week's
episode of Post Run High with Encore. If you enjoyed
this conversation. It would mean so much to me if
you took a second to follow the show, rate it,
review it. It really helps more people find post run
High and it helps us continue bringing you inspiring conversations.
I'll see you guys next week for another episode.
Hi guys, it's your friend Kate Max and welcome back
to Post run High. We talk a lot about building
wealth and success, but not enough about what to actually
do once you have it. Today's guest has built and
sold a massive company, made real money, and then had
(00:21):
to figure out what comes next. Today's episode is with
encoren Adpaul. He's the founder of Teachable and someone my
husband Jeremy and I have known for a bit now
here in New York. The two of them play put
all together, and I've always had such great interactions with Encore,
so it was really fun to finally get a run
in together and then sit down to chat after Encore
grew up in Oman with Indian roots and came to
(00:44):
the US to study economics at UC Berkeley. While he
was there, he started building Facebook apps, yes, the kind
that tell you which friends character you are most like,
and before he knew it, those apps were making him
real money. That early entrepreneurial spark eventually led him to
found Teachable at just twenty four years old, which he
went on to sell for about two hundred and fifty
(01:06):
million dollars by the time he was thirty one. Since then,
Encore has seen every side of the founder journey, from
scrappy student projects to major exits investing, and now continuing
to build new businesses. But what I loved most about
this conversation isn't just Encore success. It's about how open
and transparent he is, about the mindset behind it all.
(01:26):
We talked about how his definition of success has evolved,
what freedom really looks like, and what his life is
like outside of work. I was also pleasantly surprised to
find out that he is quite the athlete himself, which
I semi knew from his pidel skills, but we dive
into that a bit at the start of our conversation.
All right, let's get into it. This is Encore on
(01:46):
Post Run High. Encore, welcome to Post Run High.
Speaker 2 (02:00):
Thank you. Excited to be here, even though I had
to run to get here.
Speaker 1 (02:02):
We ran a couple of blocks, and by that.
Speaker 2 (02:03):
You mean we ran twenty miles. Good pace, kept it going,
kept the conversation going. It was good. It was good.
I haven't been running a lot lately. I am supposed
on a marathon later this year, so maybe this was
my training run number one.
Speaker 1 (02:15):
Oh well, what's the farthest distance you've ever Ran.
Speaker 2 (02:18):
I did the Brooklyn Half two years ago.
Speaker 1 (02:20):
Okay, so you have never done a full marathon.
Speaker 2 (02:22):
Now iver done a full marathon. The Brooklyn Half I
got into because I'm a very competitive person and we
had a group chat with eight people, and all I
cared about was beating the other seven. You know, the
time didn't matter, did you I did? I did? I
barely edged it out. Because people always say running is
an individual sport. It doesn't matter how you do, it's
just about yourself. I didn't care about myself. I just
wanted to beat the others.
Speaker 1 (02:43):
What marathon are you doing Berlin?
Speaker 2 (02:46):
Wow?
Speaker 1 (02:47):
Jeremy's friends doing Berlin too?
Speaker 2 (02:48):
October thirtieth, September twenty second, something like that. Oh okay, yeah,
that should be fun. The big reason I'm doing it
is I've been prioritizing spending time with family a lot,
and my brother's really gotten into run, so it's a
little brother activity. So as a result I have to
actually do it.
Speaker 1 (03:04):
Well, that's going to be so fun. Are you guys
going to do October fast after? No?
Speaker 2 (03:08):
I have a team retreat right before, so Lisbon then
straight to Berlin. But yeah, I'm looking forward.
Speaker 1 (03:12):
Okay, what's your training looking like Recently?
Speaker 2 (03:15):
I keep myself pretty active, but most of it is
either playing sports or working out. Running is something that
as I get closer, I'll probably do one long run
a week or something, because again, it's not the primary
thing I'm optimizing for. My goal is, I don't know,
trying to do it in four hours and not die.
Speaker 1 (03:29):
The first time I did the New York City Marathon,
I ran it like right under four hours, and that
was my goal too, and I literally was doing no training,
Like I mean, I did a little bit of training,
but I was in college. I was a sophomore. I
was drinking going out.
Speaker 2 (03:41):
In that What was the longest run you had done
prior to that.
Speaker 1 (03:45):
It's funny because whenever you run a marathon, people will
say to you, training wise, you should get to like
a twenty or twenty two mile run. And I think
the farthest I had gone was like sixteen miles, and
I was like, oh, I'll be fine. And then the
first time I did the New York City Marathon, I
got to mile eighty, which is when you get into
the Bronx, and it was like raining that year, and
my legs were so fried to the point where I
(04:07):
had to stop, like I completely hit the wall. And
I had brought like an extra pair of socks for
some reason, and I was like this woman in the
Bronx helped me change my socks on the sideline, and
oh so.
Speaker 2 (04:17):
That's a beautiful New York story.
Speaker 1 (04:18):
Though beautiful New York story, I can tell you that
it was horrible. But I did still finish in under
four hours, and that was impressive. But I remember, my
older brother has a video of me running at mile
twenty four, and if you guys know the New York
City Marathon, you know exactly where mile twenty four is
in Central Park. And he posted it on his story
and I literally looked like I was walking, but in
(04:39):
my mind I was running, And I was like, Connor,
why would you post that? But you know what, still
did it.
Speaker 2 (04:46):
I hope there's an old German Man waiting for me
in mile twenty two with some socks.
Speaker 1 (04:49):
Yeah. Yeah, you're a padel guy. But on our run,
you were talking a little bit about cricket. So let's
talk about movement and how it looks in your life.
Speaker 2 (04:58):
Yeah, so now a lot of peop people know about
you know, all the work I do in tech. But
until age fourteen fifteen, my goal was to be a
professional cricketer. Like I spent pretty much every day from
age like five, six seven till fourteen fifteen thinking my
dream was to play cricket for a living. Wow, And
I got relatively far. I played internationally for the country
(05:20):
I grew up in, so I played for Oman at
the under seventeen Asian level. But cricket and Oman is
like cricket in America. You're very good in a small country,
and when we went to play against better kids in India,
were like, you're good, but not good enough to do
this for a living. But as a result, being competitive
physical movement has been such a big part of who
I am, and even now I feel like just playing
(05:42):
team sport is something that has shaped me quite a bit.
Speaker 1 (05:45):
Yeah, And I feel like when you grow up playing
team sports, it's so fun to like continue on in
your adult life being competitive and I like knowing that
you've picked up at all. But for people that don't know,
let's talk a little bit about cricket for a second.
Because I feel like I grew up I would be
at lacrosse tourns and I'm going to say, like kind
of over in like a baseball diamond type of setting.
(06:06):
I would occasionally see people playing.
Speaker 2 (06:08):
Cricket, people in the white and I.
Speaker 1 (06:12):
Never knew like what cricket was. I knew it was
similar to baseball, right yep, But like explain.
Speaker 2 (06:18):
Cricket to absolutely so think about it as a baseball
with two bases. People have this vision of like, oh,
cricket is played by old British men and wearing all whites,
and the games go on for five days. And while
that is the genesis of where the sport came from,
today's version is three or four hours, super quick, very competitive,
there's two bases. But at the same time I find
(06:41):
what I find powerful about it is that the team sport.
But at the same time it can be incredibly isolating.
When you're batting, you have eleven people around you cursing you,
yelling at you, calling your mom all kinds of names.
But as a result, it builds this mental resilience. You
have a person coming towards you hurling a fithysical object
which if it hits you can kill you. Right you
(07:02):
have protective gear. So it's this very physical, very mental
sport that played such a big part in my life
and if you move outside the US, it is actually
the second most followed sport in the world after soccer.
Speaker 1 (07:13):
Oh wow, I did not know that.
Speaker 2 (07:15):
It is insane. A big part of it is India, Pakistan,
Sri Lanka. These are big countries, but it is the
second most followed sport. Even when they held a game
in New York City last year they brought the World
Cup to the US, the cheapest tickets for games between
India and Pakistan in New York was fifteen hundred dollars,
which is pretty insane for a sport that's, you know,
completely Unamerican. It was almost as expensive to like watch
(07:38):
an NBA Finals as like a random cricket game in
New York.
Speaker 1 (07:42):
And you are still a big cricket fan.
Speaker 2 (07:44):
I'm a big cricket fan. Now it's more on watching
and I recently also decided to buy a stake in
a team, so it was like, I want to invest
in it. I haven't played as much since it's a
hard sport to play. You have to go up to
the Bronx, spend like a couple hours getting there, play
for eight hours, so it's a day.
Speaker 1 (08:00):
Yeah. They play in Van Cortland Park.
Speaker 2 (08:01):
They played Vancortland Park a game that before.
Speaker 1 (08:03):
Because when I went to Fordham, when I was a
freshman and a little bit of my sophomore year, I
lived at the rose Hill campus, and I decided my
sophomore year, I was like, let me just switch things
up a little bit on campus here, and I tried
out for the cross country team, where I guess I
walked on technically didn't try out.
Speaker 2 (08:18):
And yeah, this makes a marathon less impressive, but go on.
Speaker 1 (08:20):
Yeah, we used to always see the guys playing cricket
at Van Cortland.
Speaker 2 (08:23):
Yeah, it was such a big part of who I
am as a person and how I grew up. So
now deciding to buy a piece of a cricket team
was almost like me paying the eight year old version
of myself to kind of go back to what I
thought would be awesome as a kid. Yeah.
Speaker 1 (08:36):
I mean, your younger self is probably like that's pretty bad.
Speaker 2 (08:40):
Yeah exactly.
Speaker 1 (08:41):
Okay, Well, let's talk a little bit more about your childhood.
So you were born in India, but you didn't spend
the majority of your life in India, right, So like
paint the picture for us of what your childhood was
like where you grew up.
Speaker 2 (08:52):
And yeah, yeah, a little.
Speaker 1 (08:53):
Bit about it.
Speaker 2 (08:54):
So I grew up in Oman, in the Middle East
country that not a lot of people have heard of,
but it's a small country that also has a lot
of oil money. And my parents moved there in the
early eighties simply because the country discovered a lot of oil.
As Indian people, you would make twenty percent more money
by moving there, So they moved there. And honestly, I
spent the first seventeen years of my life there and
(09:15):
it was pretty ideal. My biggest regrets were it got
kind of boring by the time you get fifteen sixteen
and you're a little bit rebellious, you want to go out.
It's a pretty tame, quiet sort of place, so I
was itching to leave. But otherwise it was a very relaxed,
very sort of good childhood from what I can imagine.
Speaker 1 (09:33):
And we kind of touched on this on our run.
But you grew up almost shaped by three different cultures, right,
because that's seventeen. You ended up moving to the US
for school, but you have a little bit of like
your Indian background and then growing up in Oman. How
does Oman differ from growing up in India, Like, is
it totally different?
Speaker 2 (09:51):
Yeah, so Oman culturally so culturally, I mean we're Indian.
I'm I'm not a religious person, but born Hindu. Oman
is an Arab state. It's a Muslim country. Alcohol is
like somewhat prohibited. There's rules on what you can wear
and where you can go. Relative to the Middle East,
it's probably the most chill country, but it's still the
Middle East. So culturally, yes, we were from India, but
(10:12):
if I go back to India, I'd never quite fit
in there. Oman you're always a transient worker right at
the end of the day. We are expats. You have
no immigration status, no legal status. So while it's home
in a lot of ways, it's not home here. I
don't speak Arabic. I would imagine at this point, I've
been in the US a little bit over fifteen years.
America is probably my primary identity, but it's still very
(10:33):
different from someone born here or raised here. All of that.
Speaker 1 (10:36):
Do you feel like there's certain attributes from your childhood
in India and Oman that have translated into your life
here in the US.
Speaker 2 (10:45):
I think I'm so much better in this country than
back home. Why as an example, I by the end
was pretty bad at school back there, because school was
very regimented. You had to like study really hard. You
couldn't work the system. There's a lot of math and
science and if you weren't willing to put in the hours,
you wouldn't do very well. I came to the US
(11:05):
and I realized college here is like one big game.
You can figure out which classes to take, which classes
to actually show up for, how to get credits in
random ways. And I think the US society that's.
Speaker 1 (11:16):
Not making the US look great, Come on it.
Speaker 2 (11:18):
Does it does? I think this is why you have
entrepreneurship here, like the fact that you can come here
and take initiative and that is rewarded. Initiative is not
rewarded anywhere else. As an example, when I was here
as in Silicon Valley studying at the University of California, Berkeley,
I started a business in college that was making at
(11:39):
first twenty dollars a day, then a few hundred dollars
a day. And I was amazed by how many really smart,
impressive people were willing to meet with me, talk with me,
give me feedback. When I tried that back home in India,
they don't take you seriously as an eighteen year old.
The US and especially Silicon Valley is one of the
few places in the world that will take you very
(12:00):
seriously as a sixteen, seventeen, eighteen, nineteen year old. And
I think that's what makes this country very, very like
the best place to start something.
Speaker 1 (12:08):
Why do you think that doesn't exist as much in Oman.
Speaker 2 (12:12):
I think it's less that it doesn't exist in Oman specifically,
VERSUS America is just that special. And the reason for that,
I believe is you have two hundred years of selection bias,
where for two hundred years, the people that weren't happy
with where they lived moved here. Now you multiply that
sort of risk taking across many, many generations, And what
I think makes this country super unique is for hundreds
(12:34):
of years, smart enterprising people from across the world, across
the discipline have moved here to start a life, and
that really compounds over period of time.
Speaker 1 (12:45):
Yeah, it's incredible. When you were younger and you moved
here at seventeen, like, is that something that you knew
about the US that you were like, I want to
move to the US and go to college there because of.
Speaker 2 (12:54):
This, I wasn't frankly thinking that far ahead. But my
dad always in you like from the I think he
read a lot when he was younger, and he was
like from the age meeting thirteen or fourteen, he said,
look like at some point if you take your SAT
said no idea, what the SATs even war? And he
he's like, you have to go to the US since
you know, if you are entrepreneurial, you want to start something,
(13:17):
you want to build something incredible, There's no better place
for it. But that is the power of the American
brand where you have someone an Indian man living in
Oman had been to the US once convinced that his
children should come study in the US. And that's pretty cool.
Speaker 1 (13:34):
When you think about success in your childhood household, what
was the north star for you? And like, you know
what did your parents kind of instill in you guys?
Speaker 2 (13:45):
Yeah, so growing up, my parents are pretty liberal for
Indian parents, standards were very like, you know, do what
makes you happy. But I think my dad was always
biased that both me and my brother go out and
start her own thing. And I think a lot of
that came from the fact that he wanted to do that,
but for whatever reason, it felt like it wasn't responsible
of him too. I mean we were fine, we were
(14:07):
middle class, you know, potentially even upper middle class, but
it still felt too high risk for him to give
up a stable job to go do something. So in return,
he's like, Okay, I'll work really hard, I'll do this,
but but you and your brother should go ahead, and
you know, if you ever feel like it, go chase
your dreams, start your own thing. Don't feel like you
(14:27):
have to take the safe path. Since I did that
for you.
Speaker 1 (14:30):
I mean, your dad must be so proud of you
for what you've created before we get to everything that
you've built. Did your brother start his own company as well?
Speaker 2 (14:36):
No, my brother has had a bunch of side hustles,
but right now he's also very happy making a completely
different choice, and you know, working at a good job.
And honestly, I think his life is less stressful than mine.
Speaker 1 (14:47):
So and that's also really special because I know you
fly your parents in a decent bit right to the US,
and would you ever want them to move here? No?
Speaker 2 (14:54):
Their social lives are so popping, they have such a
great life, Like why would they give up their like crazy? Heck,
take social life to move to a new country. At
this age.
Speaker 1 (15:03):
Yeah.
Speaker 2 (15:04):
Yeah, Like I look at all my friends in New York.
Their lives are crazier than ours, Like they have parties
every night, they're happy.
Speaker 1 (15:21):
Well, what made you choose UC Berkeley.
Speaker 2 (15:23):
I got rejected from every better school than UC Berkeley.
It was very simple. I think I overshot my college applications.
I got rejected from every IVY League school. I got
rejected from. Stanford Berkeley was the best school I got into.
So it was very simple. In the US, you have
the luxury of visiting all your colleges and seeing which
one you connect the most with. For me, for most
(15:45):
Indian kids, it's like, Okay, what is the best school
I get into? Sure, I'll go there. And the first
time you're on campus is your first day of class.
Speaker 1 (15:52):
And you were seventeen, not eighteen, correct, So you were
a year younger than most of the kids.
Speaker 2 (15:55):
You're younger. I graduated at twenty, so I graduated before
I could legally have a drink.
Speaker 1 (16:00):
Well, UC Berkeley's a good place to land.
Speaker 2 (16:02):
It was a good place to land. It was a
little bit different from what I was expecting. This sounds
really dumb and corny, but at the time, you know,
A big part of what you learn about America is
like movies and TV and stuff and as yeah, food
and as embarrassing as it sounds. I go to college
and in my mind, I'm like, Oh, this is going
to be like American Pie. This is going to be
(16:24):
like frat parties and red solo cups and just people
doing crazy things. But it was a pretty dorky engineering school.
Like the first day I get there, half our floor
is just playing video games, like no one wants to
socialize or doing their own thing, And I was like,
this is not the US college experience I was promised.
But being on the West Coast and stuff was pretty
(16:45):
helpful and it helped me meet a lot of great people.
Speaker 1 (16:48):
During that transition process. When you first moved here, was
the transition hard? Did you feel like? You know? What
was that like? For you?
Speaker 2 (16:56):
It was easier than you would imagine. And I think
there's a couple of reasons for that. I think one,
seventeen is early enough where your own identity is malleable,
you can change quite a bit. So a lot of
my friends who moved to the US at seventeen culturally
changed quite a bit. The ones who moved to twenty one, right,
four years. Those four years make a massive difference. The
(17:18):
second thing is the US is relatively easy to move
to compared to most of the world. I had a
hot take that I got canceled for online for saying
where I said America was the least racist country in
the world. And I genuinely like two years before that,
I'd studied in an all boys school in Australia and
that was a truly hard experience of trying to adjust
(17:39):
assimilate going to like a US college campus. I think
it's one of the friendliest places you can go, no
matter where you're from.
Speaker 1 (17:45):
What would your advice be for other students like you
transitioning into a school in the US and kind of
being in the US almost for the first time.
Speaker 2 (17:57):
The mistake I see a lot of people make, or
at least I think it's a mistake, is Indian kids
will come and hang out with the other Indian students
Chinese because we'll hang out the other Chinese students, and
I think, yes, you can have one friend group from there,
but you know you're starting a new life, like assimilate
and meet people from everywhere versus sticking to your own
kind or whatever.
Speaker 1 (18:17):
Yeah, and I feel like you having left India at
such a young age and growing up in Oman and
then moving to the US like having those kind of.
Speaker 2 (18:23):
Currect I already didn't have a single group I could
go with where I'm like, we're exactly alike.
Speaker 1 (18:29):
Yeah, that must That probably helps so much more than like,
you know, you ever really thought. Okay, well, let's talk
about your experience at UC Berkeley, because it was transformative.
I want to dive into the Facebook apps, so paint
the picture for us. What were you like as a
freshman you're student, and when did you first start becoming
entrepreneurial on your own?
Speaker 2 (18:49):
Yeah? So freshman year, I I mean I still personality
wise was the same. I spent all my time trying
to figure out, you know, how could I get good
grades while being the least amount of work. Yet I
always had this guilt that my parents were spending a
huge part of their life savings to send me to college. Right,
So there's a guilt kind of wing on me. So
(19:09):
I would always go to class and be pretty responsible.
I got a campus job my second semester. I got
an internship at Amazon after my freshman year, which at
the time I was like, Wow, this is like sick.
I was eighteen earning five grand a month. There's a
lot of money back then, still a lot of money.
It's still a lot of money.
Speaker 1 (19:28):
Everybody that I was making when I first graduated college,
I'm pretty sure.
Speaker 2 (19:31):
Yeah, yeah. And I was an intern and I moved
to a Seattle to intern at Amazon as an eighteen
year old, and for the first time in my life,
I felt positively miserable in Seattle. I was super homesick
because it was the first summer back. All my friends
were back home. I had this like, I don't know
if other people have felt this, but your first adult
job kind of sucks. Like you realize you go to
(19:52):
the office, you're there for so long, you come back,
you're kind of tired, and if you do it all
over again. I was eighteen. I didn't know anyone in
Seattle who was the same age as me. I didn't
have a fake idea, so I couldn't even go out
to places. But the upside of that is it coincided
with the launch of the Facebook platform, where you could
(20:12):
create little games and quizzes on Facebook, and having nothing
else to do on nights and weekends, I started to
play around with that, and by the end of that
summer got to a point of making you know, ten
or twenty dollars per day. And I have never had
a job since that Amazon internship. It also just made
me realize having a large job is so soul crushing.
There was a time, firstly, my entire team at Amazon
(20:35):
worked on such a small thing. My entire team worked
on one page inside one dashboard. And there were a
couple of days where I didn't go into the office
and no one even realized how horrible is that that,
like you matter so little? Like I was such an
annoyance for my boss that he didn't care if I
showed up or didn't.
Speaker 1 (20:53):
Yeah, Like, when you take a really entrepreneurial kid that
loves building things and working for yourself, and you know, yeah,
just you love building things, like and then you put
them in a nine to five job, you really are
like a cog in the system, a CS job at Amazon.
I mean, that's just not the right place for me.
Speaker 2 (21:10):
I wouldn't hire myself. As someone that hires a lot
of people, I would absolutely not hire myself.
Speaker 1 (21:14):
Yeah, well, of course not. You don't want somebody that
you know wants to start their own thing or your company.
Let's talk about building the Facebook apps, and you know
what Facebook kind of looked like at the time, and
how you guys started making money from it.
Speaker 2 (21:27):
Yeah, absolutely so back in the day. I mean, now
Facebook is the old person platform, but back then it
was the place to be right our first few years
of college, everything was shaped by it. When my freshman
year of college, Facebook was for college is only I
think by my sophomore year that expanded to other high
schools and stuff. But it was growing really fast. It
was a hotbed of activity, and they allowed anyone to
(21:48):
build an application on the platform, and as a result,
you could build something and potentially have millions of users
within the span of a few days. It was quite
unlike anything we've seen seen up until that point on
the Internet, where if you had to reach millions of people,
it was super difficult. But I spent the next three
years in college building all kinds of games and quizzes
(22:09):
and these hyper viral apps that would reach millions and
millions of people. So things like personality quizzes or somewhat
would answer five questions. It would tell them how good
a lover they are, just like stupid stuff.
Speaker 1 (22:20):
Like that, how are you coming up with the ideas
for the quizzes?
Speaker 2 (22:23):
So initially I would try and do a lot of
research work quite hard. Then I realized it doesn't matter
as long as you write good enough descriptions, like we
had a quiz called what color is your Aura? And
as long as the descriptions were good where it's reads
like a horoscope, where it's like, you know you're the
color of your aura is black, Kate, You're mysterious. People
think they know the real you, but they don't know
(22:44):
who's actually behind it all. And as long as you
kind of gave people what they wanted to share, that's
what really mattered. If we had a quiz, which friend's
character are you, people didn't care what character they are.
They would take the quiz over and over till they
got the care they wanted and they would share that.
So it was fascinating you get such a cool insight
(23:05):
into human psychology with millions of people.
Speaker 1 (23:08):
How much money were you making from these quizzes?
Speaker 2 (23:10):
So by the time I turned twenty one, I hit
a million dollars through this. It started out with ten
or twenty bucks a day. It peaked at tens of
thousands of dollars a day. I think our biggest day
was like fifty grand a day. But it was up
and down, right, You'd be very popular for like six days,
then would die down entirely.
Speaker 1 (23:30):
And when you say our, you basically are saying that
you went from doing this on your own late nights
after your internship at Amazon summer of your freshman year
to then what recruiting people at Burris recreated all my roommates.
Speaker 2 (23:42):
My head like, and this is so different, right, you like,
it's doing business when you don't know anything about business.
Anyone I recruited, I'm like, okay, fine, you do this,
you get thirty percent of revenue. You do this, you
get twenty percent. It was the craziest deals that didn't
make any sense, but it was really fun. Like we
I lived with three people who ended up and still
are amongst my closest friends. Brought them in on the business,
(24:02):
hired developers. It was a good crash course in building
a business before I even turned twenty one.
Speaker 1 (24:07):
What do you think the Facebook quiz has taught you
about business that was applicable to you, know your future
businesses like teachable and what you're doing now.
Speaker 2 (24:16):
I think it taught me about growth specifically, like that
entire platform was a time when you had to do
so much social engineering to grow anything. And I think
a lot of those lessons have stayed with me today
even now. I've never had as many people use anything
I've built since then. Like back in the day, we
peaked at about two to three million people a day.
(24:37):
There was a time where we had more traffic than
the New York Times, more traffic than LinkedIn. It was crazy,
and you know it was from a dorm room, so insane, so.
Speaker 1 (24:47):
Nuts, And did you guys continue doing it throughout college? Like?
How long did this last for?
Speaker 2 (24:54):
I did it till about a year or so after college.
It would always ebb and flow since you at shutdown
or the rules would change or the applications get less popular.
But after like this fifth or sixth time shutdown, I
started to feel like I wanted to build something more substantial,
because as cool as this was, you were only as
(25:14):
good as yesterday's revenue. You were building no enterprise value.
But also at a certain point, games and quizes are fun,
but you look back and you're like, am I truly
making people's lives better? Yeah.
Speaker 1 (25:25):
And also if you like think about it in like
the lifespan that you're saying for the games, you wanted
to building that with something that was sustainable. Did any
of the people that helped you build out these apps
on Facebook end up working at teachable?
Speaker 2 (25:41):
No. Two of them are finance bros. And ones of
plastic surgeons. I went in completely different worlds.
Speaker 1 (25:45):
Wow, Okay, so it really was a sideholso for you
as in college. Then what happened after college? Where did
you start working?
Speaker 2 (25:51):
After college? I had the two years, i would say,
of trying different ideas and nothing quite clicks. I probably
tried twelve or fourteen different startups. And at the time
that was also when I decided to it wasn't working
and pack my bags and move to New York City
and try to almost start over. And that was the
time I think my parents' faith was tested a little
(26:12):
bit because there was a divergence in what my mom
and dad wanted. My dad's like, yeah, keep going, it
doesn't matter, like who cares this, You'll figure it out.
My mom's like, well, why don't you work at Facebook?
You know they could hire you. Can't someone hire you?
But I'm glad I stuck it out until then starting
teachable when I was twenty four.
Speaker 1 (26:30):
I love knowing how supportive your parents were.
Speaker 2 (26:32):
They were and continue to be incredibly supportive, like they.
Speaker 1 (26:34):
Just always knew that you were going to make it
happen on your own, my.
Speaker 2 (26:37):
Dad more so than my mom. But yeah, I did.
It did work out. Through this whole process, immigration was
a stressor because I had a student visa. I sponsored
my own student visa. I then extended it, and then
at one point, which is around the time right before
moving to New York City, I had to leave the country.
I was told I had to leave the country, so
I googled the cheapest community college I could find get
(27:00):
another student visa. But I constantly had this sort of
stress of I can't legally stay here unless I figure
this immigration stuff out. So that does make things a
lot harder.
Speaker 1 (27:10):
How did you finally figure it out?
Speaker 2 (27:12):
I finally got a very good lawyer, and I applied
for something called the one visa, which is an extraordinary
ability visa, but it's something that the alien of extraordinary
alien exactly. It's very welcoming visa. But from there I
got my green card and eventually passport.
Speaker 1 (27:26):
Wow. And then by building your business here does that
help with immigration?
Speaker 2 (27:29):
So I only started Teachable when I figured out immigration.
It was got challenging enough that as soon as I
got that, I formally incorporated Teachable.
Speaker 1 (27:37):
Well, let's talk about how the idea for teachable came
to be, and I want to premise this with guys
when Encore was thirty one. He started it at twenty
four and by thirty one he sold Teachable for two
hundred and fifty million dollars, which is incredible. But let's
start with the basics. How did you guys get the
idea for teachable? And you know what did it start
out as? And then kind of what did it evolve into?
Speaker 2 (27:59):
Yeah, absolute, So it was never a big grand vision
or a grand idea. It was one of many different
side hustles or things we were trying. Where my buddy
Conrad and I we started. We saw this platform you
to Me, had come out where you could sell online courses,
so we decided to help some people sell their courses.
We soon realized why don't we create our own courses,
(28:19):
did that and then found a lot of challenges with
the you to me model where it was a marketplace.
They kept a really high revenue share. They owned the customer.
So I built the first version of Teachable almost as
a side project for my buddy Conrad, and we sold
a couple thousand dollars of courses when we launched, and
was like, okay, maybe there's a real idea here, and
(28:41):
then started offering it to other people.
Speaker 1 (28:43):
And when you say you were selling courses, like were
you having other people create the courses?
Speaker 2 (28:48):
So it started with other people, and then we said,
why don't we create our own courses. We had courses
on the whatever I did with the Facebook apps, growth marketing,
all of that.
Speaker 1 (28:56):
It's so interesting. And it started as like it was
almost like a social media platform.
Speaker 2 (29:00):
Right, yeah, I was super unintentional. It was. It was
always selling courses in your own websites. The product didn't
change much. But this is before the creator economy, right.
We didn't know Instagram, YouTube, everything would blow up. They'd
be all these big creators. We thought our target audience
was educators, so we got that frong. But as we
kept building the business, you know, the creator economy happened
(29:20):
and people started selling millions and eventually hundreds of millions
of dollars a year of courses.
Speaker 1 (29:25):
When did you guys realize that the company was going
from a startup to a real business.
Speaker 2 (29:31):
Probably so we It took us six months of just
messing around before I decided to incorporate and raise money.
I would say about a year after that it started
to feel like we started to make tens of thousands
of dollars a month. And at that point it's like
we maybe on we may be onto something, You may be.
Speaker 1 (29:47):
Onto something, and you're like, we need to make sure
we have the right team here. Let's talk a little
bit about hiring people, because I think that is one
of the hardest things for entrepreneurs, right, Like, what was
your hiring strategy when you guys really started growing tea?
Speaker 2 (30:00):
Initially it was one hundred percent vibes Like I wish
I could say. We had an interview process our first
our first engineer who became our CTO. He showed up
like an hour late to the interview, and either way,
we had a good chat. I described like one thing
I was working on chat kind of I kind of
forget about it. The next morning he emails me at
like six am. He stayed up all night building a
(30:23):
working prototype of what I was talking to him about
I'm like, cool, you're hired. We'll figure out the details later.
Speaker 1 (30:28):
Okay, that is more than vibes.
Speaker 2 (30:29):
Hiring people on where they went to school or where
they worked has turned out to be one of the
worst strategies I've found. Indexing a lot on people who
want to be there. I also index a lot in
people who move fast for better or worse. My operating
style is quite fast, and sometimes it is chaotic. It's
not easy for other people to keep up with. But
I like that from the people I hire.
Speaker 1 (30:48):
I've interviewed a lot of people like yourself that have
had this extreme level of success, and one of the
things that I've found with the most successful people is
that they're so quick to respond.
Speaker 2 (30:58):
Like is that a common out of it's a commonality.
I also bet if I were to hypothesize, there's a
high correlation with ADD like better or worse. I mean,
I'm not medicated add but you know, I think if
I grew up in America, I may have been. But
where you either reply right away or you're going to
forget about it. So the ones the people who do
reply are the ones who reply pretty quickly. But yeah,
there's a just a bias towards action, right, I don't
(31:21):
like kind of waiting around on stuff. I'm also very
instinctive when it comes to making decisions, So I think
that tends to help. If I think about all the
things that have made me good at what I do
and successful, those traits have a negative expression as well,
and I think that's a great example where we can't
take the good parts of our personality without also getting
the bad part of the exact same trait. So, yes,
(31:42):
I'm also impulsive. I probably take too many risks, But
if not for that, I would not have gotten the
positive expressions of that.
Speaker 1 (31:48):
When you guys first started out, what were the core
focuses for you when you were building your business? Like,
I know some of the things for you guys were
keeping outs bend low. You built a lot of your
moment off of organic growth, right, So like, let's talk
through those kinds of decisions and what made you guys.
Speaker 2 (32:05):
Yeah, absolutely, I would say there's basically three phases of
our growth. Phase one was just unmitigated kind of stupid
hustle where we would do insane, unscalable things to make
the numbers go up no matter what.
Speaker 1 (32:19):
Like what I give us some EXAMPCE.
Speaker 2 (32:20):
So there was a time when there's this guy which
had we wanted to sign up on our platform. His
name was Pat Flynn. He was a very big deal
in the world of online courses. Then Pat kind of
was ignoring all my emails. So I started looking at
every single conference he was going to, and anytime I
go to a conference, I'm like, hey, Pat, I'm going
to be here. Finally he once I saw he was
going to be at this conference called fin Conn in
(32:41):
North Carolina somewhere. I hit up Pat. I'm like, hey, Pat,
I'm going to be at fin Conn. He's like, cool,
I'll meet you for breakfast eight thirty tomorrow. I gotta
get there now tonight. So flew there. Obviously I didn't
have a conference ticket. I wasn't going to the conference,
met him for breakfast, signed him as a customer. He
became an affiliate. I flew back after that meeting. It
was stuff like that we did repeatedly, Like we had
(33:02):
a month where our customers weren't selling a lot, or
we had sorry the next month, we didn't have any
big course launches. So Conrad and I gave up our
Thanksgiving plans flew to Berlin with our biggest creators, took
a camera, recorded something, launched it the week after. So
we just had to do these things in the early
days before there was an engine that really worked.
Speaker 1 (33:25):
Yeah, no, it makes sense because it's like, you guys
have this platform that's built on courses, but you literally
need to find people, Like it can't just be you
guys making courses forever, like it has to be other
people as well. What were your other strategies to getting
people on Who was like the first person that you
guys got onto your platform.
Speaker 2 (33:41):
So the first big person so we got the first
person was obviously Conrad. The first couple of people were
other unim ME creators. But something pretty fortunate happened where
two of our creators made a million dollars in the
first six months, and the benefit of that is so
much pr right now. It's like John and Elliott are
twenty seven and twenty eight traveling the world, made a
million dollars teaching people how to build iPhone apps. So
(34:03):
then that got us the first sort of growth spurt,
and that's what led to our primary growth strategy that
we ran for most of the company, which was storytelling
about other creators. We realized our competitive advantage is the
best creators on our platform, especially if they were in
the world of business or making money online, they in
turn could be our biggest affiliates in promoters. So that's
(34:26):
the strategy we used for the next three or four years.
Speaker 1 (34:28):
Yeah, it makes so much sense.
Speaker 2 (34:29):
It's like, now it's obvious. At the time it felt
like crazy, but now it's you look at these businesses.
Speaker 1 (34:34):
Oh yeah, it's so true because it's like when you
think about I mean, when I think about YouTube, I'm like,
why do I want to be on YouTube? I'm like,
because so many of these other creators have had so
much success on YouTube, of course I want to like
try to have success on that app as well. It
makes the same It's kind of just something for Teachable,
and I think that's a cool notion to go into too,
because when you guys first started out, it was pretty
early on into the creator economy per se.
Speaker 2 (34:56):
There was no creator economy. We stumbled into it, basically.
Speaker 1 (34:58):
Literally stumbled into it. Like what did you learn about
the creator economy from building Teachable?
Speaker 2 (35:04):
It was fascinating since again there was no such thing
as the creator economy. But then we started to look around.
We're like, where can we find people that could be creators.
An insight that seems obvious now is we realize it's
easier to teach someone with an audience how to teach
than it is to teach a teacher how to build
an audience. The other thing is, I think we got
fortunate in timing, like we rode the wave of when
(35:28):
online courses were really big. Like I think the heyday
of courses were sort of twenty seventeen, almost peaking in
twenty twenty, and they've sort of declined a little bit.
I still think the creator economy is and will continue
to be massive, but the exact products will keep changing.
Speaker 1 (35:52):
How soon into you guys creating Teachable did things like
master Class come out.
Speaker 2 (35:56):
I would say roughly midway through they were out. But
they were always different variants. When we started, for instance,
skill share was really big and then they kind of,
you know, disappeared. There's a company called Creative Live. There
were always different form factors. What we got fortunate on
is by empowering the creator. We were very close to
Shopify but for information, but that meant the creator did
(36:18):
all the distribution. We were just the technology platform.
Speaker 1 (36:20):
It would have been cool if there was, like I
don't know if there was like a teachable Times master
class type of thing, because you would, like they're very different.
Speaker 2 (36:26):
We did. We did a few deals like that where
we'd help people create content, and what we soon found
is those businesses are hard enough that anytime we did that,
it turned into a shit show we were not prepared
for because you start doing something that's not your business,
and it's just a constant reminder that you have to
be better at saying no to things.
Speaker 1 (36:45):
Yeah. Absolutely, well. When I think about Masterclass two, I
almost think of like it's like a mini TV show, right,
Like it's like a mini TV series.
Speaker 2 (36:52):
So master Class. The problem Masterclass is like, the best
teachers we find are not the celebrities, right. The best
teachers are someone whose story you relate to. Like I
don't want to learn how to shoot a basketball from
Steph Currery. I want to learn from the other Indian
kid who's probably better than me, right, And people want
that relatability and Masterclass you right, it's entertainment less of education.
Speaker 1 (37:12):
What was it like selling a company during COVID.
Speaker 2 (37:14):
It was wild? I mean, you have nothing to compare
it to at all, but it was at the same
time it felt like a weight off my back. Yet
it was also hard. Right, you've been building this thing,
you care so much about this thing, and now it's
someone else's thing. What made it even more interesting slash
complicated is right the day after we sold it to
(37:36):
three months later, the business doubled. We saw more growth,
more like it was. The craziest times at work were
right after we sold, which honesty was probably good because
there was so much else happening in New York. New
York was a terrifying place of the time that it
kept us busy, but it never the realization almost never
sank in since you were so caught up in the day.
Speaker 1 (37:56):
To day, you ended up still working on it for
the next for a few months. Was selling, right, So
let's talk about what those months kind of looked like,
and how your position at the company changed after selling it,
and maybe what those emotions are like once you sell
a company.
Speaker 2 (38:08):
Yeah, so the emotions again, as I said, it's very
different because we were all in lockdown. There was no
cathartic like post exit party. I still get people from
the company who tell me that I owe them that
they're like, we never got to celebrate, like we all
to post sort of exit party. So it was it
was definitely a little bit more complicated since you're in
lockdown and kind of coming to grips with all of that.
(38:30):
For me, my life only really changed when I stepped
away from the role entirely, Like my life did not
feel different just having more money in the bank or whatever.
And by the end, and this also related to why
I sold the company, I don't think I was enjoying
it that much. The reason being, I felt like a
lot of my role was typical CEO stuff, which is
(38:51):
so much less fun than building and creating things, where
I had to deal with executives who had managers who
had other reports, and you spend all your life in
these long meetings every day, and it felt like it
was going nowhere. But when I stepped back is when
I really found the quality of my life improved.
Speaker 1 (39:09):
What is your role now? I care?
Speaker 2 (39:10):
Right right now, I am also the CEO, But when
you're a small company, I don't think it's really a CEO.
I think you only really become a CEO in a
true executive way when you have fifty hundred people and
if I feel the same way in the future, I'll
step away and bring in someone more qualified.
Speaker 1 (39:25):
What do you think is your favorite thing about building
a business?
Speaker 2 (39:28):
The people? Undoubtedly, like I look back on all the times.
Yes we made money, Yes we built a successful business,
but it's always the relationships. It's the team. So many
of the customers are still friends, our earliest investors. These
are lifelong relationships that compound and grow. I also think
(39:49):
having a good time while you're doing the whole thing
takes a lot of the pressure off, since you're like, look,
no matter what, like I'm getting to live my dream
and do something really fun.
Speaker 1 (39:59):
So, out of the people, what did you do post
selling your company? And also I want to put this
in the perspective of like twenty year olds listening to
I know you said your life didn't change that much
after you sold the company, but in actuality, like you
do all of a sudden get this like big deposit
into your bank account. How does it work? Is it
like a wire transfer?
Speaker 2 (40:19):
You get a really big wire transfer one day you
get and then you get smaller amounts one year later
and two year later. They always reserve some money in
case shit. Fox up where you can pay them back
or whatever, but yeah, I want big wire transfer. My
stories are very boring. Though I did nothing crazy. I
bought a secondhand car, which is insane. I didn't need
to buy a secondhand car, but I wanted to go
surfing at Rockaway Beach and I was like, oh, you
(40:41):
know what, I deserve a car, So I bought a
second hand car. I want to travel, but most of
the world was locked down. But I realized Tanzania was
in lockdown, so I went to climb Mount Kilimanjaro. I
was one of the first people to do that. Right
after And yeah, then, honestly, like a lot didn't change.
I bought a house. But even then it was like,
this had to be a good, responsible decision. But what
(41:04):
started changing a lot is once I wasn't doing my job.
That freedom let me spend two years travel the world,
spend more time with my family, you know, go hang
out with friends that not seen in a long time.
That I felt really was awesome.
Speaker 1 (41:18):
Having made a lot of money. How was your perspective
changed on money?
Speaker 2 (41:24):
I feel fortunate in that. I again, I've seen other
friends go through something similar where their burn rate or
whatever has linearly gone up. I definitely spend more money
now and I have more than enough for everything I do,
but it hasn't dramatically changed a lot of stuff, Like
some lifestyle changes are massive, are like I'll always like
(41:44):
get a life flat seat when I fly on a plane,
long flights or stuff like that. I can be more
generous with friends and family, so that's been awesome, but
it hasn't like dramatic, Like I don't find myself in
the pursuit of much more like I want to build
a really large company now and I want it to
be financially successful, but more because that's a way of
(42:05):
keeping score versus I think the like another fifty million
dollars will change my life. I think at this point,
as dark as it sounds, like, more money will just
change the number I go to the grave with. It
will not change much. I have. I have enough, basically,
like a lot of people ask is what is enough?
And I don't know. For me, it wasn't what I
(42:26):
had before the exit, and I'm definitely well passed it now,
so somewhere in between. But yeah, I definitely feel like
I have enough.
Speaker 1 (42:32):
And then post building a successful company. How do you
think your perception on life has changed.
Speaker 2 (42:37):
If I look at my life and think about what
is excited me motivated and make me made me happy,
it is like playing and winning sports games of different kind.
And as I even when it came time to start
my next business, part of the framing in my mind
is like look for better or worse. My sport now
is a little bit lamer than cricket. It's building a business.
(42:59):
And I'm still in the prime of my career and
I'm too young to kind of hang my boots or whatever.
But I still think like retaining that sense of like
adventure and competitiveness and you know, while keeping it lighthearted
is such a big part of who I am, and
it's something I think as you get older you have
to fight to retain, but I, you know, work towards that.
Speaker 1 (43:20):
Let's talk about when you decided to start building your
next company carry which by the way, I'm technically an
investor in very small investor, but still counts.
Speaker 2 (43:28):
Size doesn't count. You guys are investors, That's what's important.
It took about I would say between eighteen and twenty
four months.
Speaker 1 (43:35):
Wow.
Speaker 2 (43:36):
Before it was quick, it was.
Speaker 1 (43:38):
It probably felt like a while though.
Speaker 2 (43:40):
Time the benefit and this is also why I love
traveling so much. Is when you change your day to
day environment, time feels slower. So those eighteen months definitely
felt like things slowed down in a really good way.
But by the end of that I started to crave,
you know, building something with a group of like minded people,
the latter being very important. Like for me, the business
is a part part of it, but I wanted to
(44:00):
build a business with a group of people where we
like each other. You know, that was such a big
part of my life for almost seven or eight years.
I started to miss that and yeah, decided to it
all over again.
Speaker 1 (44:12):
And when you started teachable it was and even till
the day you sold, it was such a simple idea.
What is this simple idea that Carrie has to offer?
Speaker 2 (44:24):
The tax code in America is incredibly hard for the
average person to understand and take advantage of, and we
want to build software to just do that for you.
So today that manifests itself and we help people set
up retirement plans and do tax saving strategies. But really
the big north star is if we can help you,
(44:45):
every other person listening to this show take advantage of
all the opportunities that otherwise you'd need expensive lawyers and
accountants and a lot of time and paperwork to do.
Speaker 1 (44:54):
So what does the platform like look like for people?
Speaker 2 (44:57):
Like?
Speaker 1 (44:57):
How does it help?
Speaker 2 (44:58):
So today, we have a list of strategy that can
help most people save money. Like we have a one person,
four one K plan for anyone. As a business owner,
we have retirement accounts called iras that let you do
all kinds of you know, conversions. If you're a high owner,
we let people do something called the backdoor roth, the
megabackdoor oth. We have a cash management product that will
put your cash in the most tax advantage money market fund.
(45:20):
So think of it as a way where you come in.
You have a list of strategies, you can pick the
ones you like, will custody your dollars, and at the
end of the year, we can also file your taxes
for you. Yeah, it's a fully different world. I underestimated
how difficult the world of fintech and finances. But as
I said, you know, like keeps it interesting.
Speaker 1 (45:37):
Yeah, definitely. How many people work at the company.
Speaker 2 (45:39):
Now, we're eighteen people right now? Wow?
Speaker 1 (45:42):
All right, so you got that startup culture going by
the time you sold Teachable, how many people were working
at the company.
Speaker 2 (45:47):
Almost two hundred, which I would say is about one
hundred and fifty people more than what feels good from
the perspective of, you know, truly feeling like a small startup.
Speaker 1 (45:55):
What are you doing differently this time that you wish
you had known to do going into building Teachable.
Speaker 2 (46:00):
I will caveat with I still believe I'm going to
make a whole new set of mistakes. I think doing
something two times is a very very small sample size.
But this time we're fighting even harder to keep the
team as small as possible. At Teachable, we did, but
now you know, eighteen people, we could probably be two
to three times as many people. But I've just seen
the effectiveness of small teams and that's a really, really
(46:24):
big thing we're trying to do. We're also spending very
little money on paid marketing. We're trying to build our
business in a very lean way that we don't have
to just because of seeing friends do the opposite playbook,
where you raise a ton of money and you're spending
a lot of money and then the whole train kind
of runs away from you.
Speaker 1 (46:41):
Yeah, and there's nothing like a startup culture, and it's cool.
Knowing that you love being in a startup environment, small
team kind of comes into play with that. Well, we
learned so much about you today. Thank you so much
for sitting down with me. I've got one final question
that I want to ask you. Knowing what you know now,
what is one piece of advice you would give to
your younger self.
Speaker 2 (47:00):
People overestimate risk, like I think one of the biggest
biases we all have. It's very natural is risk feels
like the scary thing, but as a result, our brain
over indexes on the negative part of risk. I think
it took a fair amount of risk. I think I
could probably have taken two to four times more, and
I think that's true for most people listening to this.
Speaker 1 (47:21):
Well, thank you so much. There's so much we can
learn from you, for everybody that wants to follow you,
stay up to date with your journey and everything you've
got going on. Where can we find you?
Speaker 2 (47:29):
Yeah, I'm on social it's my full name on Twitter,
it's my ankr NA on Instagram. Pretty active there otherwise,
carries atcarry dot com.
Speaker 1 (47:37):
Thank you guys so much for listening to this week's
episode of Post Run High with Encore. If you enjoyed
this conversation. It would mean so much to me if
you took a second to follow the show, rate it,
review it. It really helps more people find post run
High and it helps us continue bringing you inspiring conversations.
I'll see you guys next week for another episode.
Host
Kate Mackz
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