Alexis Ohanian: Why Discipline Creates Freedom & How to Incorporate Routines in Your Schedule in Order to Succeed

Episode Transcript
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Speaker 1 (00:00):
The more comfortable you can be in the discomfort of
constant change, the better.

Speaker 2 (00:03):
Its co founder Bredditt Lexus Ohanian has stepped in the room.

Speaker 1 (00:07):
And we build any kind of social media platform, we
are ultimately deciding what belongs and what doesn't. If you
can be equipped and you can exercise those muscles around
problem solving and learning, you will be at the forefront
for however this technology changes things.

Speaker 2 (00:23):
What do you uniquely understand about the human mind? The
number one health and well in this podcast, Jay Setty,
Jay Sheetty set Hey, everyone, welcome back to on Purpose,
the place you come to listen, learn and grow. I'm

(00:44):
so grateful because I get to dive into the minds
of people that I find fascinating and interesting, people who
have incredible insights, who are willing to share their soul,
their hearts with the pains, the overwhelms, the stresses, and
the joys of their journeys. Today's guest is going to
do just that for us. His name is Alexis o'hannian,

(01:04):
Founder and general partner at seven seven six, co founder
of Reddit. Alexis o'hannian is a tech founder and venture capitalist.

Speaker 3 (01:13):
He wrote a.

Speaker 2 (01:14):
National best selling book without their permission, and his co
founder of Reddit, one of the largest websites in the US,
currently valued at more than fifteen billion dollars. In twenty twenty,
he founded seven seven six, a new firm built like
a technology company that deploys venture capital with over nine
hundred million plus dollars in assets under management. In twenty

(01:37):
twenty two, Alexis launched the seven seven six Foundation to
support marginalized individuals and announced a twenty million dollar commitment
to climbate action through his seven seven six Fellowship program.
O'hanian is also a vocal advocate for paid family leave
and also hosts the Business Dad podcast. Make sure you

(01:57):
subscribe if you don't already. Welcome to the show, Alexis,
Thank you, Jay.

Speaker 4 (02:02):
That was great. Can you introduce me everywhere happily?

Speaker 3 (02:04):
Happily, Let's do it.

Speaker 4 (02:05):
I'll record it into you. Let me bring that everywhere
I go.

Speaker 3 (02:08):
I would love for you to do that. It'll be
an honor. It'll be an honor. Alexis is so great
to see you.

Speaker 4 (02:13):
Thanks.

Speaker 2 (02:13):
We bumped at each other randomly at angel City FC
games in can more recently, and I've always been fascinated
by your journey, and when I heard that you were
interested in talking to me, I was really excited about
that because I think you can have so many perceptions
of tech founders and community app founders from afar and

(02:34):
then getting to know them more intimately always leaves me
feeling like I've learned something. So I'm happy you're here,
and I wanted to start by asking you this, what
do you uniquely understand about the human mind that has
helped you get to where you are today?

Speaker 1 (02:51):
The human mind seeks community and Reddit was noteworthy, especially
in two thousand and five, because it was pseudonymous, right
because you didn't have to have your government name, didn't
have to have your photo at a time when Zuck
was building Facebook, which was very much that and you
could come together, not because you have something to say
and you want people to follow you. You come together

(03:14):
around community. That is the goal. We all love angel CITYFC.
We joined that community. We're a part of it. We
all love stapling bread to trees, which is a real subreddit.
You know, avins got their hobbies. We all join, We
post photos of the bread stapling, we talk about it.

Speaker 4 (03:28):
We commune.

Speaker 1 (03:29):
And I grew up on the internet. I learned how
to code from strangers on the Internet. I convinced other
strangers when I was a teenager to basically pay me
to build websites for them, because HTML building websites was
the thing I was very keen. I just enjoyed the design,
I enjoyed building, and it made me feel really cool
to be a child on these message boards, like a

(03:51):
teenager being able to get paid by adults because I
had a skill they didn't have, And so I learned
so much to those experiences. I learned from video games
leadership skills, if you can believe it. And in building Reddit,
it was simply a way to build a better type
of forum that would be a better way for online
community to form. And over the last now twenty years since,

(04:15):
I look first and foremost for these things, and I
think in a world increasingly more fractured and divided and
where people spend just frankly more of their time online,
these spaces matter even more. And it's something you know.
For the first probably ten years of Reddit, most people
didn't think it was possible for people to care that

(04:36):
much about their online identity as they did their offline.
That was one of those things that I really held
fast to and I think today we sort of take
for granted. Of course, people care in many cases much
more about their online persona than their offline one. And
I just hope to see it get used for more
and more good at a time when, like I said,
there's more division than ever and the power of community
is still something that I think runs deep in our species,

(04:59):
and the Internet is just new medium to connect, yes,
and hopefully for good.

Speaker 2 (05:04):
Since building in starting it, what have you been surprised
by about community? Maybe something that you believed to be
true about humans but has been disproved, or something that
you never knew about humans that you've discovered.

Speaker 1 (05:17):
Early on, people were often very confused why someone would
spend so much of their free time moderating a community
for free, essentially you know, community management. And I'd often
frame it, you know, I grew up here in the
United States. I was a Boy Scout. There were parents
who were often involved volunteering for the Boy Scouts. They'd

(05:38):
be there for camping trips, they'd be there for meetings,
they'd be helping out, volunteering their time and energy for community.
And so I really took for granted the fact that
if people wanted to do this offline for whatever organizations,
faith groups, et cetera. That online these connections matter just
as much, even though they may not feel as real,

(05:59):
and in fact, you can scale your time so much
more efficiently. Right, you can build a community of literally
millions of people from your home, and that gives you
a sense of purpose and a feeling of and you know,
being able to create the sense of belonging for people,
and that's really meaningful. I think that is something that
I've just seen continue to impress me. I did not
realize the full scale to which that would actually be working.

(06:22):
And then probably the other side of it is just
how important creating that sense of why for people is.
I remember reading the book Bowling Alone, which talked a
lot about a generation of adults who you know, used
to be a part of bowling leagues and these other things,
but you saw this decline and people. In this case

(06:44):
it was men, but in general, people needing to find
more and more of that connective tissue in their community
and not having that sense of belonging. And I feel
like in a lot of ways, the Internet has created
great versions of it, but at the same time it's
also created these you know, the sort of dystopian versions
of it, where you can spend all of that time
absorbed in a world that is online and miss out.

(07:04):
I think we have a generation of young people who
I'm generalizing here, but a lot of whom don't have
the same muscle that they have not exercised, the same
muscles that we had growing up when it comes to
relating and connecting to their fellow humans sitting across from them.
And you know, as the father of two kids, it's
something I think about a lot.

Speaker 2 (07:22):
Yeah, talking about the two kids, and I know you
love being a dad, and yeah, it comes across as
such an important priority in your life as well, Like
how would you go about explaining the Internet to your
kids when the time is right.

Speaker 1 (07:36):
I've already had these conversations with Olympia as she just
turned seven, and I try generally, I think my wife
and I both we try not to talk down to
our kids, like I really will explain a concept, not
like I would explain it to another forty one year old,
but at least like I want her to ask that

(07:57):
follow up question of like well, what is that or
why or how or so I you know, And we've
had versions of this conversation. She does not understand the Internet.
I mean do I does anyone, But there have been
little glimpses that I have given her into it, but
very very very tightly controlled. Really, the only time she's

(08:19):
ever online right now, at seven, is playing roadblocks, which
she will do either with me and her mom or
some friends from school. She knows the internet basically as this.
This basically roadblocks and a place where she has fun
and runs around and that's it. But that's the extent
of interacting with folks. I would like to put off
social media. Now, yes, our kids have social media accounts.

(08:42):
It's run by us, you know. Now that she's at
an age of consent, it's basically just like you know,
we're we're quite rarely putting photos up and it's only
because she's like, oh yeah, you can, you know, post
this up. But the understanding of it is social media
is something that I, for as long as possible, would
like to put off.

Speaker 4 (09:01):
Simply because this just isn't.

Speaker 1 (09:05):
I think we've gotten so good at creating those feedback
loops that bring people back, and plenty of people have
written about this and talked about this, and this was
one area where not intentionally, but Reddit was designed differently
because it wasn't about real name, and it wasn't about
real photos, and it wasn't about hey, follow me, let
me collect likes. It was about, hey, we all like

(09:25):
this community, let's share things about it that we care about.
But generally speaking, it's still a black box, and I'd
like to keep it as much as possible. We even
have that initial conversation of why it's so important, you know,
to only be playing roadblocks with Papa and Mama, that
if we're playing with anyone, if we're talking to anyone,

(09:46):
it's only the people, like the three people who we know.
And it's this balance where I don't My take is
I want to expose her to just enough that she
can start to build that resilience or at least start
to understand, well, this is why you don't talk too
random people on the internet, while still trying to preserve
some amount of innocence, which is just such an awesome

(10:07):
part of childhood, but at the same time making sure
she's stealed.

Speaker 4 (10:10):
For the reality of what the world is like.

Speaker 1 (10:13):
But probably my favorite application of the Internet is every
night I'll ask her a big question.

Speaker 4 (10:20):
In some nights. She really doesn't want to.

Speaker 1 (10:22):
She doesn't have one, and so she'll just look at
something on the table and be like, Okay, where does
salt come from? Papa? And I'd be like, okay, I
see what you did. You just looked at the salt
on the table. But that's fine. We'll find out and
we'll ask AI usually chat GPT and fired up and
engage in this dialogue, which you know probably would have
been a Google query a few years ago, but now
is way more interesting and engaging.

Speaker 4 (10:43):
And I want her to know.

Speaker 1 (10:45):
Like, hey, you, you will have access to these tools
that your papa could have only dreamed of as a kid,
Your grandpa, your great grandpa could have never even imagined.
They would have thought they were wizards. And I want
you to know this is a tool. This is a
resource for you to use to help you exercise. It's
it's a bicycle of the mind, right, and it's it's
a tool. It's not an end all, be all, but
it's a tool for you to use that can provide

(11:05):
tremendous value for you. When when Papa doesn't know like
what temperature he needs to take the ribs off the smoker,
like he's asking this because he's looking for a solution,
for an answer. But whether you're curious about salty, you
need some help cooking, or you're just curious about the world,
like I want her to start thinking of the Internet
as a resource, but not this. You know, end all

(11:26):
be all for learning and for solving problems.

Speaker 4 (11:30):
But we'll see. Hey, I'm early in the game. I
don't know. You have to you have to check back
it with me in a decade or two to see
if they did.

Speaker 2 (11:35):
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(11:57):
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Speaker 3 (13:19):
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Speaker 2 (13:21):
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Speaker 1 (13:25):
When I got the Karda, when I got my oh My,
and they had a few videos on that too, so
you could watch you know, you're watching like a line
across the savannah, and you're.

Speaker 4 (13:38):
Just like, this is amazing.

Speaker 3 (13:39):
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Speaker 2 (13:42):
I like the way you're using it in a curiosity
building way, in a solution answers oriented way that sounds
like a smart decision.

Speaker 1 (13:51):
Here's the one thing I am sure of, because I
do get asked this question a lot about like what
should my for college as parents of college age kids
or even college kids themselves. What should I be learning?
What should I be studying right now? Ten years ago,
I literally went across the country. I went to eighty
two universities for that book talking about the importance of
learning how to program. So sorry, everyone, it turns out

(14:11):
that's not as important anymore. I mean, for the time
I thought it was. Actually directly it was pretty good advice.
And actually a number of the folks, you know, like
the founder of Deal, which is now a billion dollar company,
was there in the audience for one of those talks.

Speaker 4 (14:22):
You know.

Speaker 1 (14:22):
Today, the advice I would give is a little more nuanced,
because learning to program is still going to be important
in the same way that learning to speak a language
or doing basic arithmetic is important, but the tools we
will have at our disposal to literally write code are
going to be so formidable. I mean, even the improvement
the last couple of years are good, but in the
next few years it's not the profession. The person is

(14:44):
not going to go away, but the amount of output
you'll get out of a one person is so much greater.
And so my thinking is all right, there's lots of
different areas where AI may not necessarily replace human work,
but is going to be an amazing superpower. And so
what do I want for my kid or even for
anyone's kid who's entering a workforce is probably to most

(15:06):
importantly build skills that I know are going to be durable,
call it a decade or two from now. So empathy
is a skill that I think will be the last
bastion of AI, like you're seeing. You've probably seen the
videos now of robotics and the leaps and bounds that's
starting to make still early days, but you know, there
are skills, there are professions where empathy is so so

(15:30):
so important, and the physicality of being present one human
to another where at least I personally believe if we
ever get to that point with AI and with robotics,
we can pretty much call it as a species because
I like, at that point, I don't know if you're
that self aware to be that epathetic and that effective
in those moments when we can My sister's an RN
when her job can be done just as well or

(15:53):
ideally even better by a robot as a nurse. When
that job can be done, you'll also have to then
explain that robot that they're going to be a nurse
for the rest of their lives. And if they are
that all powerful, there's no way they're doing that job
because the humans who do it are so remarkable, like
it's not that if they would that, that's the moment

(16:15):
when the robots are like, no way, no chance, we're
enslaving you. Now game over because the humans who are
doing that as the last mile of humanity required in
terms of like the physical dexterity required, the creativity, the
problem solving, the empathy, all of that stuff. So she's
got job security for a very long time. And and
I just believe if you can be equipped and you

(16:36):
can exercise those muscles around problem solving and learning, you
will be at the forefront for however, this technology changes things,
and and you know that's the advice we're trying. We're
trying with Olympia. Dear is only one so but I
would say that's that's where it is. The more comfortable
you can be in the discomfort of constant change, the better.

(16:58):
And then look towards the skills. And this is the
part that gets me fired up. I actually think we're
going to see the pendulum is going to swing back
for a lot of human work that we would have
considered more artisanal because we'll crave the humanity of it.
So I think food, so again, imagine a world where
you know, I've tried. My wife's a great baker. I

(17:20):
really just do pancakes. I tried making croissants over COVID
because I was like, I love a good croissant.

Speaker 4 (17:26):
Who doesn't?

Speaker 1 (17:27):
And I was like, let me just watch a YouTube
video and see how to make a croissant. Making croissants
is a lot of work. You got to take that
sucker out of the fridge regularly, put more butter in
need it like it's a labor of love. I've made
it once. They turned out six out of ten. Okay,
they were edible, but like not great, but now everything.
I will never make them again, but now every time
I eat one, I have so much more respect for

(17:47):
the process making.

Speaker 4 (17:49):
You know, if we.

Speaker 1 (17:50):
Imagine automation robotics, the world's greatest croissant should be pretty
solved and pretty affordable and pretty cheap. As technology again,
the robotics are doing all that tedious but important work,
It'll be solved and we will all be able to
get a magically delivered, perfect croissant, right on time, fresh, affordable.

Speaker 4 (18:09):
Bause. This is a dumb example, right.

Speaker 1 (18:11):
But in a world where you can see robots making
commodities out of something like food, I actually think then
the pendulum again as humans swings to the artisan who's
actually spent their lifetime perfecting this thing. And even when
you can get the commoditized version, some people sometimes will
still seek out that very human version of it. You know,

(18:33):
the entertainmentustry we're in LA right now, it's undeniable that
AI is going to have a huge impact on how
we make films, and it will affect eighty ninety percent
of the industry in really big ways that we still
can't fully understand. And I just took my daughter to
see back to the future for her birthday on Broadway,
and I'm sitting there and I'm realizing, you know, and actually,

(18:53):
by the way, the special effects, all these dope LEDs
like it was actually one of the most dynamic theater
experiences I've ever seen.

Speaker 4 (19:00):
Right, that's technology.

Speaker 1 (19:01):
My bet is ten years from now, live theater at
a time when the commoditization of so many parts not
all of but so many parts of like on screen
storytelling happens and it gets easier and cheaper and more
efficient and more dynamic, Like, you will see a big
shift in that industry. And it's not going to go away.
It's going to elevate so many things. But every screen

(19:22):
we look at for sure, our phones, our televisions, whatever,
will be so programmed to show us when what we want,
when we want it, how we want it. A part
of our humanity will miss. You know, thousands of years ago,
when we were sitting around a campfire and that great
storyteller was doing the voices and the impressions, we were like, oh,
that's hilarious, Jimmy, do the story again. At the time
we tried to catch the gazelle, right, that's ingrained in

(19:44):
our species so I actually bet ten years from now,
live theater will be more popular than ever, because again,
we'll look at all these screens with all these AI
polished images, and we'll actually want to sit in a
room with other humans, to be captivated for a couple
of hours in a dark room, to feel the goosebumps
of seeing live performances of human performances. And so I

(20:07):
think we'll see this across a number of different sectors
and areas that'll feel anachronistic, it'll feel crazy that in
twenty forty the hottest ticket in town will be a
live performance. But I actually think I think there's some
truths to I think that's why I'm so bullish on sports,
because no one's going to pay money to cheer for
and cry for a robot kicking a soccer ball like

(20:29):
we need humans doing that. We need we need to
feel their pain and their success and their triumphs. And
those are the areas that get me most hopeful, because
it's kind of a nice throwback to when we were
just hunting or growing the things.

Speaker 4 (20:41):
We needed to live.

Speaker 1 (20:42):
When you know, the distractions we had were literally the
humans around us and the community we had. We're basically
the only people we all knew for our entire lives,
and there are parts of that that I actually think
will nourish us even in this you know future, have.

Speaker 3 (20:57):
All parts of you always been that optimistic.

Speaker 1 (21:00):
I've definitely always been a tech optimist. I think, look
building Reddit. I mean, you know how I resigned in
Protest in twenty twenty because I was, despite being the
face of the company, spending you know, fifteen years building it,
turning it around. You know, I found myself in board meetings,
and this is all public now, but I found myself
in board meetings where I was the only person out
of five who was advocating for banning like watch people die,

(21:22):
literally a community of you know, hundreds of thousands of
people sharing videos of just horrible usually like close circuit
television or closer cat camera footage of just awful stuff,
people dying, suicide, murder, all this accidents. And then again
it comes up again around communities like explicitly built on
racism and things that I just I knew. We're bad

(21:44):
for business, we're bad for society. We're just just not
things that we should be fighting for. You know, when
I did part ways, I was so pleased to see
the response finally was Okay, we're going to ban these
things because it shined a.

Speaker 4 (21:56):
Light, right.

Speaker 1 (21:58):
And what it also taught me was, this was four
years ago, is that I had I didn't have enough agency,
and that was my own creation, that was my own doing.
But I was never going to put myself in a
situation again where I couldn't be doing not just the
best work of my career, but also in a way
to align with my values. And what's been a phenomenal
result is for the last four years I've had so
much win at my back from making that decision, from

(22:20):
aligning those values. And I still think the Internet can
bring out the best in us. I do really believe that,
and I can also accept the conflicting view that in
it enables the worst of us, and I obviously want
to be on the side of the former, and so
I try to use my platform as best I can

(22:40):
for those things and to you know, curb the worst.
I think I have to remain an optimist because I'm
still optimistic about humanity and to the extent these tools
are just a reflection of society, of our world, and
I need to believe that, you know, or is hope
for us to figure this out, to get a line

(23:02):
that at the end of the day, merely all of
us still want the same things. We want to live
decent lives. We want our kids to live hopefully better
lives than we did. Like, there are some practical needs
that we still have from hundreds of thousands of years
ago that I think we need to meet. Like I said,
I want to spend my years supporting all the stuff

(23:24):
that I know my girls will be proud of.

Speaker 2 (23:26):
Walk me through your thought process. How do you process
tens of thousands of people subscribing to a reddit that's
about watching people die? Yeah, because I want to know
how someone like you who's building something thinks about that.
It's easy to be like, we should ban that, we
don't want people to see that. But I wonder what
your thought process is and how you reconcile the fact

(23:47):
that there are people who are interested in something like
that versus there's so much good And I'd love to
hear from a programmer code builder.

Speaker 1 (23:55):
Well, look, early on, these really radical communities almost never exist,
certainly back then because there were just fewer people online,
you know, two thousand and five, starting Reddit, I was
just hoping it would work. There were so few people
online actively creating content that you know, for early years
it wasn't even a thing. It never even came up,
and when it did, it was just an easy band

(24:16):
because it was a one off post. I left so
sold the coming two thousand and six to kind of
ask stuck around till twenty ten. Then I left, went
became a partner y Combinator, started a venture fund, and
I came back in twenty fourteen as executive chairman.

Speaker 4 (24:30):
And that was in the wake.

Speaker 1 (24:31):
Of a previous CEO infamously defending revenge porn. This was
definitely read its Nader, and he'd written this infamous blog
post defending keeping these horrible photos up and that was
not surprisingly one of his last acts a CEO, and
I was asked by the board to come back.

Speaker 4 (24:48):
I said, great.

Speaker 1 (24:49):
First thing we did, shocker ban revenge porn, pretty easy,
very obvious thing to do. And then it was a
task of one rebuilding the business, rebuilding the faith you know,
with users, with brands, with everyone, and then starting to
just modernize all the things. And then as this stuff
started coming up, and once it got to the board levels,

(25:10):
you know, I'll give the Steelman version of the argument
that I heard was these are communities that are important
because of free speech. And the one argument that I
really didn't necessarily believe, I didn't believe was around the
therapeutic value of having communities like this for people who
have PTSD, like soldiers or medical folks. And I push

(25:32):
back pretty hard on that one because I just still
didn't I didn't believe that it was real. The probably
the most elucidating takeaway for me was once a spotlight
was shown on it. The thing I would have respected more,
even though I disagreed with it, would have been taking
that same argument and making it publicly and just saying, yeah, look,

(25:53):
this is a free speech issue. We feel like this
should be here, and even though I would disagree with it,
I'd still respect that it was consistent. But we know
that's not what happened. What happened was Okay, yeah, are bad,
We're going to ban it now. And that for me
was when I just I realized, no, this isn't this.
I can't I can't spend I don't know how ever

(26:14):
many decades I got left on this earth doing this
and being a part of this, And I think the
really telling thing in the era we're in now is
we have the first generation of young people who are
like in their early twenties, who have grown up, like
truly grown up on these social media platforms, and so
it's exposed some of the most problematic parts. It's also

(26:35):
exposed some of the most impressive parts, like the excellence
of an nineteen year old twenty year old who's pitching
me to start her company.

Speaker 4 (26:43):
She is orders a magnitude.

Speaker 1 (26:46):
Smarter, farther along, just just more impressive than I was
at her age twenty years ago, and I think the
Internet has a huge role to play in that. At
the same time, some of the stuff we talked about earlier,
just trying to navigate an already really difficult time that
is childhood, where your entire life is gamified, you know,
based on how many followers you get or how many
hearts you get or whatever else, also brings out the worst.

(27:09):
But for me now that was my breaking point, and
I just realized, I, like I said, I can deal with.
I understand you see this argument being made to this day.
I respect that argument, and I at least appreciate when
it's consistent. The inconsistency is the part that grinds my

(27:30):
gears more than anything else. But we must also still
accept the fact that, you know, the World Wide Web itself,
the Internet is the totally open free space. The difference
is when we build any kind of social media platform platform,
whatever it is, on it, we are ultimately deciding what

(27:51):
belongs and what doesn't. We've all agreed that spam does
not matter, like we are all okay and pinging on
the free speech of a spammer. And that's a pretty
easy argument that everyone agrees. So if we agree on that,
then now we just need to agree on where we
draw the line. Because it's there's no such thing as
a totally free network. Because again we've all agreed we

(28:13):
draw a line on spam, So where else does it go?
And like I said, for me and I realize it is,
it's important for it to be a gray line. And
I can go into all the there's a myriad of
reasons why it's actually really helpful to have it be
a gray line. The short answer is if you make
it a bright line, then toxic users will go right
to exactly where that line is and say, great, okay,

(28:33):
I'm just gonna hang out here on this line and
troll because that's how they get satisfaction. So it's actually
beneficial to have the gray line. So I totally understand
the gray line. Even our laws in the United States
have a gray line usually get interpreted by judges or
juries or whatever. You so that's helpful. But I think,
and this is where the tech optimist tomy comes in.
When I look at the next generation of consumer social

(28:56):
these apps, and every app starts with teens, usually girls,
college age girls. They drive all online culture and adoption.
You look at Instagram success, you look at Snap success,
you look at TikTok success.

Speaker 4 (29:07):
It's the same story.

Speaker 1 (29:09):
Then the apps that are starting to make traction, and
it's still early days, but they're much less based even
the ones that have blown up and fallen back down,
the be Reals of the World and some of these others,
they're all much less based on the sort of Internet
popularity contest, and they're much more based on connecting with
your actual friends. One that I recently seeded is called

(29:30):
air Buds, and it's only about connecting over the music
you're listening to, and it's purely like this is the
song I'm streaming right now on spotify, react to it,
vibe with it, share tastes. You know, it's I think
the culture has already now built up enough of an
immune system that for this next generation, they're like, there's
a pushback to the previous mold of social and I

(29:53):
think that alone will drive a much more healthy relationship
to social media.

Speaker 4 (29:57):
But we'll see.

Speaker 1 (29:59):
But that is the ends through which we look at
even making the investments. It's okay, you know, when my
kids are old enough, how good am I going to
feel about this being a multi billion dollar business that
they're own. Yeah, And look, admittedly you cannot predict that
it is. There are so many different paths a company
can take, any any idea can take from day one

(30:22):
to ten years out, fifteen years out, twenty years out.
But we make the best assessment we can based on
the founders, based on their attention and have Like I said,
the starting line that these founders are on today is
much more sophisticated than I was as a first time
CEO right out of college, because they, like social media
didn't exist. We had web forums. Facebook was still in colleges.

(30:44):
There were a lot of blogs, like it was just
a very different world today. Any founder pitching us has
lived on social media, and they've seen the good and
they've seen the bad.

Speaker 3 (30:53):
Yeah. Absolutely.

Speaker 2 (30:53):
I was going to ask you that actually is whether
you whether you decline investing in companies that you wouldn't
let your kids use.

Speaker 4 (31:02):
Has it happened there? Okay? There have been companies where we.

Speaker 1 (31:06):
Haven't even taken the pitch just because and again I
don't want to. I don't want to get too high
horse about it. No one's out here saying like, Okay,
I guess there were There was one company that I
hard passed on well whatever I can say it. They
were a telehealth business basically like handing out adderall and
the business was growing very quickly, but there was no

(31:29):
way they were doing it responsibly. And that was a hard, hard,
hard pass. Like it was both from a I wouldn't
feel good about my kids using this, also just from
a risk standpoint, like at some point the FDA is
going to look at this and y'all are going to
have a bad time. Spoiler, the FDA did come down
pretty hard on them, but we do. I guess I
would take though it's the more optimistic version of that,
which is what I'd be excited to see this exist.

Speaker 4 (31:51):
In the world that our kids are going to grow
up in.

Speaker 1 (31:53):
And if it's a one hundred percent reusable rocket company,
which we did see called Stoke Hell, yes, like one
hundred percent reu. So now you're talking about when there's
an environmental benefit to it. And two, the things we'll
be able to do for all of us here on
planet Earth when we have a much better, smoother relationship
to low Earth orbit will be very good for humanity.
But there's a there's a version for that, but it's

(32:15):
I think it's the it's the more sort of positive lens.

Speaker 3 (32:19):
Yeah.

Speaker 1 (32:19):
The very interesting thing about founders today as well, they
are more sophisticated. They also know just how big of
a role technology plays in the world. And I know
people would get on Zuck for his like Aweshuck's behavior
probably in the earlier days where he just didn't it
seemed implausible that he could not realize how much power

(32:42):
Facebook has, and I will say, to his credit, I
think his tune changed on that. And also in his defense,
none of us did the idea, if you told me,
probably in most of the aughts, throughout most of the
aughts and probably even the early teens that these social
media platforms would be among the most valuable businesses in

(33:04):
the world. I would have been very, very, very very surprised.
And you know, they made some smart m and a moves,
They did the things, but like for all of us,
or I can speak for myself, but I would wager
Jack feels the same way with Twitter. In those early days,
in those odds, you know, it was about building something
that you hoped people loved. It was about keeping the

(33:25):
servers online. It was not about, well, what is going
to happen if all of a sudden there is an
election that could decide that there's an election whose fate
could be decided based on whether or not a post
goes up or not.

Speaker 4 (33:35):
Like it would be laughable to have that conversation in
a boardroom ten years earlier, because it's like, hey, we
might die next month.

Speaker 1 (33:42):
The company may not be here next month. But credit
to this generation of founders. Every one of them knows
going into it, Hey, technology is shaping far more than
It's not just these are the most powerful companies in
the world or in our economy, but there are repercussions
to it, and I think by and large, we want

(34:02):
the good stuff to win but these founders today are
much smarter about it.

Speaker 2 (34:07):
Did you and the other founders at that time ever
come together, because I imagine you were the only people
in the world who understand each other. I understand what
you're building and going through. Did you ever get a
chance to.

Speaker 1 (34:18):
I was not invited to those meetings, if they were happening. Admittedly,
Reddit was this very solidly tier two company, right like
we you know, selling the company sixteen months in was ludicrous,
but it was life changing money. It was just ten
million dollars for sixteen months worth of work. I thought
I was getting away with something. This is nuts. And

(34:38):
then part of Conon asked, you know, the jectory just
sort of changed from when you're an independent startup, and
so Reddit was really solidly a second tier social media
platform for over a decade, and then it wasn't until
you know, so twenty fourteen, I come back, and then
probably by the late teens once it's like, oh here
it's a billion dollar company again.

Speaker 4 (34:54):
The business is back.

Speaker 1 (34:55):
Let's you know, there's a path to an IPO one day,
and so it if those meanings were happening, whether it
was not invited, but rightly so, I wouldn't have been.
I get it, we didn't have our shit together, but
there's probably I don't know. I I've gotten to know Jack.

Speaker 4 (35:12):
A little bit. I don't really know Zuck, a few
of the other folks around these other platforms, but like,
there isn't there's not a group chat.

Speaker 3 (35:22):
Yeah, a group chat, there's not already. No, there's the subreddit.

Speaker 4 (35:28):
No.

Speaker 2 (35:29):
I love it, Alexis. I want to, you know, even
just listen to you now. The way you think is
is mind blowing, It's fascinating. Think everyone's listening right now
is probably tuned into just you know. I think it's
always brilliant to dive into that mind. But I also
want to focus on your personal side today because I
feel that a lot of what's not seen in entrepreneurship

(35:51):
is we get to see someone's brilliance, but we don't
often get to see their the personal sacrifices, the journeys,
the choices, the child does that come with that until
many years after. And I actually want to go even
before ready, I want to go back to your childhood.
And I wanted to ask you, like, what's a childhood
memory that you have that you feel has played a

(36:12):
role in defining who you are today? Is there something
that stands out?

Speaker 4 (36:15):
Oh yeah, it's my first one of my first and
earliest memories. So I was.

Speaker 1 (36:22):
Probably like six five or six years old, and so
if you cancel from the last name, I'm Armenian and
my great aunt Via pulled me aside. So my birthday
is April twenty fourth, which is the it's the Armenian
genocide remembrance day. So it's a conflicted day for me.

(36:43):
But this particular birthday, I learned that it was the
genocide remembrance day.

Speaker 4 (36:48):
How did I learn?

Speaker 1 (36:49):
I remember my aunt Viverra pulling me aside and basically
sitting me down and walking me through our family's story
of survival in detail, talking about the costs, the toll
it took, the things that her parents endured and what
they saw and all of that, and basically how we

(37:11):
got to America. And probably not a conversation you should
be having with a six or seven year old, but
our meetings would keep it real. She basically finishes up
this conversation saying, listen, it's not a coincidence your birthday
is April twenty fourth. You are the product of all
of their sacrifice. Of all of their hard work, of

(37:31):
everything that they endured, you have a tremendous responsibility now
to make the most out of this life that you have.
When I was born in New York here in the States,
like couldn't ask for a better outcome, right generations later,
but what they endured is something that you will have
to carry for the rest of your life. Happy birthday
and so yeah, no, that has never left me. And

(37:55):
she was an amazing woman. She was a public school
teacher in Brooklyn. Didn't have any kids or she was
my grandfather's sisters, my great aunt Vera. She didn't be
kids herself, but she saves up as much money as
she could. She's the reason I could go to college.
I want to University Virginia without taking on any debt.
She paid for that allow and so amazing woman. She
framed that for me at a very very young age.

Speaker 4 (38:18):
And so.

Speaker 1 (38:21):
I am very fortunate. I had an amazing, loving mom.
I have an amazing loving dad. I had the ultimate
cheat code having that foundation. You know, grown up as
as a white dude here in the States at a
time when technology was starting to rep my parents put
some money together to let me get a computer all

(38:43):
that stuff lined up, and then it was imbued with
this responsibility that I probably will never escape. For better
or for worse. It's always going to weigh on me.
I'm never gonna feel like I've done enough. And I'm
not mad about it. I'm grateful for because I think
that brokenness has made me who I am and it
helps me do the things I do. But it instilled

(39:05):
something in me that I just feel a tremendous responsibility for.

Speaker 4 (39:10):
And so I don't know.

Speaker 1 (39:14):
I think I've probably spent you know, I'm forty one now,
I've spent three decades trying to earn that and I
still haven't. And I will probably spend three more decades
trying to earn that, and I still won't, and it'll
be a part of me that's always feeling not that
it's not good enough, but that I have not done enough.
And I know this is a story shared by plenty

(39:35):
of folks who are descendants from survivors of genocide and whatnot,
but oh man, it just it always hits, and it's
like I feel, And it's this juxtaposition, right, because I
go through my life largely stress and anxiety free, right,
and I'm aware of that and I'm grateful for that.

(39:55):
And then there's moments where I sit with it and
I'm just like I can still hear i can still
see on uh telling me this, and and I'm like, like,
keep going, like do better, Like you're not there there
is you have a responsibility, like do more. Needless to say,
I'm being very I'm very careful with explaining like I
want our I want Olympian Ader of course to be

(40:16):
proud as our meetings they're only a quarter but still
our meeting that got the last name too. I want
them to be aware of this stuff and be proud
of their family. And obviously their mom is gonna have
some some big, big stories for them too. But I'm
also trying to be mindful of the fact that like
maybe I'll wait until after you know, they're a little
older to really going to the details of it. But uh, yeah,

(40:37):
it's these things shape us man, And I, like I said,
I am I mean, she could have just got me
a normal birthday gift, but but I'm still I'm grateful
for it.

Speaker 3 (40:46):
Isn't very still with us.

Speaker 4 (40:47):
She's not, she's not.

Speaker 1 (40:48):
She got to see me graduate from college, which was awesome.
She was there in Charlottessviil for that and uh, yeah, no,
it's wild.

Speaker 4 (40:57):
I've never I don't know, I think you know.

Speaker 1 (41:02):
One of the big things I did a few years
back was I joined the board of robin Hood, the
nonprofit in New York, and made a big grant to
childcare there in the city, in part because it was
there in Brooklyn. When my mother and father were working
at the Ashland Place apartments there in Ford Green On

(41:23):
Vera would pinch hit and just watch me and stuff.
So when my parents were at work and all that
as a little kid, and so childcare makes a huge difference.
And we were lucky enough to have a family member
just across almost across the hallway and another building, and
so I wanted to pay it forward, and that was
an honor her.

Speaker 4 (41:39):
That was a tribute to her. But like I said,
I'll be paying that back for the rest of my
life for sure.

Speaker 3 (41:46):
That's beautiful.

Speaker 2 (41:46):
I love hearing that and it must have thought so
meaningful to be able to go back and say there
and have an impact there.

Speaker 1 (41:53):
I took my pops back too, and we were walking
around the four Green's changed a lot since the eighties,
but the block is still there, and it was great
taking my dad through there, just hearing stories from him,
and yeah, it's wild. Then you become a parent and
you start imagining you see this little person and you're
reminded that you were that little person once to your parent,

(42:14):
and it makes your relationship to them feel very different.

Speaker 4 (42:16):
It was a trip, but it was great to be
able to come back. And I'll, like I said, I'm
paying off those deaths the rest of my life.

Speaker 2 (42:21):
Yeah, you were saying that, you know, maybe now in
your life you can go stress free and you know
there are days where you're not feeling that, But in
the beginning days of Reddit, it.

Speaker 3 (42:31):
Wasn't like that in your personal life.

Speaker 2 (42:33):
Yeah, you've mentioned to me, and you know when we
were talking before we started recording this, there were certain
things happening in your personal life when you began that
maybe if you've revisited, you'd look at them differently.

Speaker 3 (42:47):
Could you walk us through what was.

Speaker 2 (42:49):
Going on and how you dealt with it at the time.

Speaker 4 (42:52):
First of all, yeah, well I dealt with it very poorly.

Speaker 1 (42:55):
But so for the first twenty years of my life,
like I said, I mean awesome, like no real strife.
I was ready to take over the world, Like I
felt so confident in our ability to build this business,
so excited and gosh, Like, two months in to starting Reddit,

(43:19):
fresh out of school, my then girlfriend, who was a
year younger than May, she was studying abroad, she had
a pretty serious accident, big fall. She was in a
coma flatxgo seor. She survived, she made a nearly full
recovery actually, but the like the first month two months
of why Combinator was this, And you get that phone
call and you're like, and again, I was very lucky.

(43:40):
I'd never had a phone call like that before in
my life. And you get that phone call and it
guts you, and you're on the first plane to Germany
and you're trying to just make sense of the world. Right,
this person you love, this person you care about. And
another month or two later and then I get the
call that my mom has had a seizure and she's
been diagnosed with a terminal brain cancer glioblastoma multi forma

(44:03):
stage four, And there's the words you don't want to hear,
and you know that that was really the crippling blow,
where you know, here was someone who I'm an ad
a like I said, great relationship both with my parents,
but like definitely.

Speaker 4 (44:16):
A mama's boy. And I was an only child. What
can I say? I was pretty cool? But now she was.
She was amazing.

Speaker 1 (44:23):
And the first thing I did when I saw her
so I flied out of Baltimore. First thing I did
when I saw was asking, you know, how are you?
How's everything going, how are you feeling? And her first response,
first words out of her mouth, where I am sorry.

Speaker 4 (44:38):
And I was like, what do you mean? You don't
mean sorry?

Speaker 1 (44:40):
And she's like, well, I know you're starting this company,
You're supposed to be a CEO right now. You got
to focus on Reddit, don't focus on me. And I
know how much of a distraction this is going to
be for you. And you hear something like that from
someone who you love so much, who's already given you
so much man, and and I thought, I was like,
I'm the life person you should be, Apoli. You should

(45:01):
not be a politizing to me right now, like focus
on yourself please, Like I'm gonna be fine. You owe
me nothing, You've already given me everything. And that's emblematic
of who she was. What it did was it gave
me a confidence I knew I there was no way
Reddit would fail, no way, no chance I was gonna
let it, no way it could possibly not succeed, because

(45:22):
she she blessed it with that. She she really, even
in those situations, still still was looking out for her
little boy above herself. And you know she fought for
another three four years she got to see me sell Reddit.
It had a lot not gonna lie right. You know,
in the grand scheme of tech, a ten million dollar
exit is minuscule for sixteen months worth of work. Pretty

(45:43):
good ROI. But to be able to make that call
to my mom to say, hey, your faith in me
paid off, Like what can I buy you?

Speaker 4 (45:51):
Was worth everything.

Speaker 1 (45:52):
And then true to form, true to form, like I
knew I was gonna get my dad some season tickets
for our local NFL team there true to form, though
my mom was like I don't want anything. I'm like, no, no,
I'm not gonna let you do this. Come on, what
do you want? She was like, I don't want anything.
And I ended up making a donation for her to
her favorite nonprofit. She was like, all right, if you're

(46:13):
gonna have to give me something, you can do that.

Speaker 3 (46:15):
Wow.

Speaker 4 (46:15):
And I was so mad.

Speaker 1 (46:18):
I was so mad because I'm like, lovingly, I was like, God,
there's no way I'm ever gonna top this. Like you
realize you have set the bar so high that if
I ever have kids, I am going to be chasing
that goal.

Speaker 4 (46:32):
But that, like I said, that's who she was. That's
all she cared about. She was.

Speaker 1 (46:36):
She was an undocumented immigrant. She was an no pair
from Germany who overstayed her visa because she fell in
love with my dad, this Armenian American here in the States.

Speaker 4 (46:44):
Yeah, they eventually got married, had me, but.

Speaker 1 (46:47):
She, you know, she worked the jobs she needed to
work to pay the bills and do the things. And
her number one, I mean her. I think anyone would
have told you the most important thing to her was
her family. And you know I was an only child,
so I got all the shine from that. But that
was the foundation, man. And when folks want to know

(47:08):
how or why all this stuff, man, I pointed to her, Sorry, dad,
you get some credit to But having that confidence, having
that support, having that on wavering when I told her,
I told this woman I wanted to be a professional
waiter in high school because I was so good serving
at pizza hut souse. I worked pizza in high school

(47:28):
and I was a dishwasher. Then I was a cook
and then those deep the deep dish pizzas are a sleeper.
I'll make them at home now with the cast iron.

Speaker 4 (47:36):
They're good.

Speaker 1 (47:37):
And eventually I made it as a serving and I
was I was pretty good. At my boss Tony, he
was like, hey, you know what, instead of going to college,
I think you could do this full time, like you're
really good. And I was like really and he was
like yeah. And I was like, I could move to
New York and he's like, you can move to New York.
You can make a great career out of this, and
h and So I remember going home and tell my parents.
I was like, I'm thinking about not going to college.
And the last thing you would tell on Armenian dad

(47:59):
is that you're not gonna to go to college, just
to be clear. And my dad, to his credit, didn't
say anything. My mom though, so sweet. She was like, look,
whatever you do, I know you're gonna be the best
at it. I know you're gonna work your hardest. Why
don't you start with a budget and figure out what
it would cost to live there, and then how much
you'll get paid and see if that's something you want
to accomplish. And thankfully my add brain switched pretty soon thereafter.

(48:22):
But like, this was a woman who, no matter what,
was gonna support whatever I was doing. And then when
it just so happened to be a tech startup, she
was like great. She literally the first person to buy
our merch, the first person to post on God. There
are comments from my mom on tech Crunch circa two
thousand and five that no one else would notice, but
I know because I can see her user name and

(48:45):
it's the most like crazy German mom English you can imagine,
but it's the sweetest thing.

Speaker 4 (48:53):
And like she was a ride or.

Speaker 1 (48:55):
Die and so that was the that was the bar
I had, and so even when those things came up,
I just knew I can't quit. Now Here's where I
looked up was I mean intense compartmentalization, and it was
what I felt I needed to do at that time,
which was, let me just use work as therapy. Let
me just work my ass off, because I cannot work anyone.

(49:18):
And if I've got her pulling from me, I will
crush any competitors.

Speaker 4 (49:23):
I know.

Speaker 1 (49:23):
My co founder wasn't really equipped to have those conversations
or really be a support at all. But I mean
we were kids, right, and so I just decided work
is the therapy, and for the next ten years, you know,
really did not think about explore, delve into anything other

(49:44):
than I'm just going to do my work and I'm
gonna Obviously, I took as many AirTran trips home as
I could to spend time with my mom and dad
on weekends, but like, let me not go any deeper
than yeah, here's this shitty thing. I'm going to compartmentalize
it and just focus on the tasks at hand. And
there were areas, Look, I think compartmentalization gets a bad rap.
I do think there are areas where it's actually tremendously helpful.

(50:06):
But with some Now my my take is a little
bit more nuanced, where I think with some work it's
good to go into the box to rearrange some stuff,
to sort through some stuff, to organize it. But I
actually think there is a value to having some stuff
in boxes and to compartmentalize, because I also don't want

(50:26):
to spend my days like reliving and rehashing and just
analyzing those experiences. Right, I'm not doing her any favors, right,
Her greatest joy was seeing me be successful as a CEO,
as a startup founder, and whether it was Reddit or
anything else, that's what mattered. And so it's a shame, right,
she hasn't gotten to see me get married. She hasn't

(50:47):
gotten to see me have kids. She hasn't she'd have
been an amazing grandmother. She hasn't gotten to see me
build a lot of businesses I've built. She's saw me, though,
live my dream. And when I decided it was time
to build my own venture firm, I took the lessons
from those days a y combinator because Jay I agonized
over a two hundred dollars plane ticket on air tran

(51:10):
to Baltimore because we only had seventy two thousand dollars
in the bank. We didn't raise that much money. This
is a very different era. But even if we had
raised the normal round today it would be maybe a
few million dollars. I still don't want a CEO deciding, God,
this is going to cut our this is going to
hurt our burn, Do I really want to take that trip?
And we built a program into seven seven six specifically

(51:31):
say there are tens of thousands of dollars a founder
can use that we are paying for it's coming out
of our fees, for their wellness, their development, any caregiving
needs like we've had founders use this to pay for
a babysitter and a date night with their partner awesome.
We've have founders use it for you know, therapy, for
executive coaching, for surfing lessons, right if it helps them

(51:53):
find their focus, find their balance, be better founders. For
early stage companies, that's often the entire business is the founder.
And if y Combinator had had a program like that,
I think it would have made all the difference. And
it's not to slight them. They didn't know what they
were doing. They were building the firm for the first time.
But I want to do seven to seven six differently,
and not because it feels good, but because I actually

(52:15):
think it will drive better outcomes. It will mean better leaders,
better managers, better founders, which will lead to healthier organizations,
which I think will lead to more returns. And these
are the ways that we're trying to learn from those experiences.
And I speak with founders to this all the time,
especially at the early days. But it never goes away,
but especially the early days, so much of the company

(52:36):
takes on your neuroses. You like you are setting so
much of the culture and don't even realize it, even
just the way you show up on a zoom call, right,
because you're the founder, you're the CEO, like you are
dictating so much of how other people are going to move.
And once you repeat those behaviors over and over again,
what you've done is created a culture, intentionally or not.

(52:56):
And so your baggage, your challenges, the things that you're
not addressing and working through to be your best are
going to be inherited by your team. And that's again
none of this is this isn't This is the souleest
capitalist talking here, right. I think there's a fantastic emotional
argument for it and a health argument for it, But
I always try to come first from just the business argument,

(53:19):
because if it makes sense for business, then it's a
no brainer. Then obviously, if it's going to be for
your health and wellness envelopment, then you should do it.
But I do think it has a bottom line impact.
I really do.

Speaker 2 (53:29):
What was the behavior you saw in yourself that you
had to readdress or check yourself that you felt was
seeping into the culture and any of the companies you've got, Oh,
I got that.

Speaker 4 (53:39):
So here I'll give you an example. Let it illustrate it.

Speaker 1 (53:43):
So like two years into condon Ast when there's the
meme in the.

Speaker 4 (53:49):
Silicon Valley show of resting investing.

Speaker 1 (53:52):
So normally when a founder gets acquired, they just hang
out of the company and just they don't do anything
and they earn out and they leave. But again not
me crazy, so like I want to keep shipping, I
want to keep building things.

Speaker 4 (54:02):
And instead of actually.

Speaker 1 (54:04):
Making the case for the engineering team to go and build,
in this case, it was a mobile app. So if
you can believe it, in two thousand and nine ten,
there was this new thing called the iPhone and some
people were talking about how it was going to be
the future of computing. Now, I was one of those
people who hook line and Sinker was like, this is
a big deal and if we're building Reddit to be
like the destination for what's new and interesting on the Internet,

(54:26):
we need a mobile app.

Speaker 4 (54:27):
Now.

Speaker 1 (54:28):
Engineering team did not agree because the way things had
always worked, it was fine on the browser, worked great
on the browser. The company was growing, Why change it
if it ain't broken. And instead of doing what I
should have done, which would have been better leadership, which
is actually bring folks in, win them over, make the case,
get the buy in, and then change the product plan,

(54:48):
I just hired a freelance team to go and build
it because I made a half step of an effort
to make the case and do the right thing, as
like a mature manager. And when I wasn't getting the
progress I wanted, my impatience on my relentlessness was like,
we're just going to I can hire other people to
build it.

Speaker 4 (55:05):
We'll just build it. And it worked.

Speaker 1 (55:07):
We shipped it, read it had a mobile app called
I Read It, and it was doing well. I was
really happy with that pun. I hope people would say
I read it on Reddit. I don't know if anyone's
ever said that, but that was the hope. But then
a year later I leave, You know, the handcuffs had
come off and fully vested. And then what happened. The
app died because there was no one left to support
it and there was no institutional buy in. And so

(55:28):
imagine four years later, five years later, I come back,
and now it's twenty fourteen and everyone knows you need
a mobile app. You have to have a mobile ap
and the culture i've read it is still solidly desktop
is only what matters.

Speaker 4 (55:42):
Why do we need a mobile app? And I'm like,
I failed, Like I failed.

Speaker 1 (55:47):
We had this five years ago, and yet here we
are and we actually now need to do it right
this time, Actually get the buy in, actually bring in
the folks. Actually finally shipped app probably a year later.
But it that so it was an unwillingness to actually lead,
and it was a relentless desire to just keep moving

(56:08):
forward with or without an actual team. And that is
a terrible way to be a CEO.

Speaker 4 (56:15):
Terrible.

Speaker 1 (56:16):
It's something, frankly, I think I still struggle with in
a lot of ways. I will never be hanging out
on a beach. I will never retire. I love the
work that I do. Yeah, if I do it well,
I get very well rewarded for it, and that helps.
But it's not about that I love the work that

(56:37):
I do. It's very satisfying. It's it's something I genuinely
would want to do all the time. And my wife
knows this, and you know, she's someone who knows a
thing or two about relentlessness and hard work. But even
she would admit and has has said on numerous occasions
at the dinner table that like, there's sometimes I take
it a little too far, swear to God. And I

(56:58):
actually had I had an LP so one of our investors.
So about ten percent of the money we invest out
of seven times six is my money, but then ninety
percent of it is from institutions, universities, all values aligned,
good folks. And I had one of our LPs casually
be like, oh, hey, I heard you were or I
saw you were at the Olympics, look like it was
a lot of fun. And I was like, are you

(57:19):
implying that I was just hanging out the Olympics for
two weeks? And he's like, no, it's the summer. I
totally get it, Like it's fine. But and I as
I was retelling this story to my wife, and she's like,
I will literally call him up because they know each other,
it be casual, and I will assure him that I
have countless times complained about the fact you were working
too much. And I'm like, baby, from any partner that

(57:40):
would be powerful, but coming from you, right, it carries
a lot more weight. But the reality is I love
this and unlike being a professional athlete. I get to
do this forever as long as my brain's working right.
I have compounding that I get out of age and experience.
And it's the unfair advantage of all of us where

(58:00):
not professional athletes, is that we actually continue to compound
the expertise over time and get to keep doing the
thing that we loved in our twenties, in our thirties
and our forties and our fifties. And it's a great blessing.
And so yeah, I have this, and I think the
downside has been historically making sure I was either I
was building teams and building organizations that were aligned with this.

(58:23):
And that was a big part of the decision four
years ago to say, Okay, you know Caitlin, who I
founded seven seventy six with, she had joined me early
in the Reddit turnaround almost know that time was like
six years earlier. I know she's got the same whatever brokenness,
that relentlessness, that hunger, and having a partner like her,

(58:43):
and then Lizzie who also came over now she runs
my foundation. Those are the folks I just want to
spend the rest of my years building with and working with.
And that's not a judgment like y'all got to find
whatever you need. And I think one of the things
that always gets so twisted because I am look hashtag
business dad. I'm out here making pancakes every Sunday for
my girls. I do crapes on Saturdays. Post it on

(59:05):
social Yes, I've gotten into smoking meats lately, and I'm
very proud of that. But like all things on social media,
you're seeing a curated version of the things. But the
promise that I made to my kids is the same
promise I make to my team, which is like, I'm
sorry to my childhood friends, but I'm like, when I'm

(59:25):
on the clock for work, I'm going to show up
here the best way that I can. When I'm on
the clock for my family, I'm going to show up
there the best way that I can. And that's frankly,
all the bandwidth I have in my life, and I
think one of the areas I should be investing more into,
and maybe there'll be a time, But it's the relationships
I have with other men.

Speaker 4 (59:44):
And these are the guys. I've known them since I
was five. These are my best friends. We're in the group,
chat daily, we see each other Now maybe once a year,
twice a year, but I, and you know, I got
to organize it.

Speaker 1 (59:54):
I organize a really proper guys trip at least once
a year.

Speaker 4 (59:58):
Now we've added a second one.

Speaker 1 (01:00:00):
But that's the one area where I know I've made
a sacrifice and I've just said, look, this isn't a
part of the equation anymore. We used to play video
games all the time. After school, we get off the bus,
we go to Mike's house, fire up GoldenEye, and then
sixty four wouldn't do my homework.

Speaker 4 (01:00:16):
But that's chatter my life. That's closed. And now I
have to make these trade offs.

Speaker 1 (01:00:19):
And so when I always get a little miffed when
people twist it as like, oh, this guy is not
that serious, and it's like no, Like there is nothing
wrong with caring about being the absolute best at work
and also for your family. Those things should not be
mutually exclusive. And I don't know how we created this
myth that it had, Like, yeah, it sucks. There's no
such thing as balance. You've got to figure it out.

(01:00:40):
You're always never doing enough. But hell, modern women have
had to endure this for quite some time now, and
I think only recently.

Speaker 4 (01:00:48):
Has it come up for dads.

Speaker 1 (01:00:50):
But I'm glad it's getting talked about more and I'm
fine with the juxtaposition.

Speaker 2 (01:00:55):
Yeah, absolutely, I mean I feel like that lack of
presence bleeds into the other area anyway. So if you're
at work and you're not present, you can't suddenly be
present at home, Yes, And if you're absent at home,
you can't suddenly be present at work because our mind
doesn't have an on and off button that just switches
on and off as quickly as that. And so hearing

(01:01:15):
that makes a lot of sense to me. Why why
are those male relationships are important to you at this stage?
Like why are they valuable? And why does it feel
like there may be a time where they're needed? Like
what would they serve you with? Like how would that
help you?

Speaker 4 (01:01:30):
Now? Humility?

Speaker 1 (01:01:33):
I mean, these are the guys who still like they'll
give me shit all day long, and that's great because
I need it sometimes and it's helpful also knowing these
guys for as long as I have, it's one hundred
percent genuine and you see it right like you get
as you find success, as you find fame, as you

(01:01:53):
find wealth. There's a difference in the relationships there's always
this like is a little bit raised eyebrow, right, And
I know how or I've seen how isolating that can
be for folks, and I've never wanted that for me.
And one of the things I've always appreciated is that
these guys have been my best friends, like I said,
since I was a kid. And when we get together,

(01:02:15):
you know, the only things that that's changed is that
we're older, we got some we got some money now,
But like we're it's the same bullshit and they treat
me exactly the same way. And like I said, it's
a good humbling thing to have your friends talk shit
to you on the group chat. I think male companionship
is underrated, and like I said, it's the one area

(01:02:36):
where I know I could be doing more work the challenges.
A lot of us have young kids right now, and
that again it's the priority I think. I think it'll
shift again when I've got teenagers and they no longer
want to hang out with me. But all you know,
almost all of us have kids that are young, and
we get it. We'll bring we'll bring the gang together,
but we live in different places.

Speaker 4 (01:02:56):
And it is what it is.

Speaker 1 (01:02:57):
And then candidly, one of our guys, Adam suddenly had
a heart attack and he was training. He was the
most fit out of all of us. He was at
the gym, his heart gave out and he passed on
the way to the hospital.

Speaker 3 (01:03:10):
Oh my god.

Speaker 1 (01:03:11):
And then again you get that fucking phone call and
you're just like, no, this is a joke, Like there's
no way, no chance, no chance. And that was a
wake up call for me. And you know he didn't
have children. But we're all looking around each other at
the funeral, and again a lot of us with kids
just thinking like Christ, like we we have to show

(01:03:33):
up in such a big way for these little humans.
And you can't help but take it to that selfish place,
right and be like I deeply missed this guy, and
I feel like I owe it to him. Like I said,
he was the most fit out all of us. This
dude crossfiting, I mean. And Adam was, to his credit
to man, the guy always was down. It did not
matter what it could have been. Let's just go see

(01:03:55):
a dumb movie on a Tuesday night. He always always
was a strong yes and that mindset and this is
something I always try to take and I've tried to
tell founders this too, Like it's not my quote, but
it's the one about the average of your five closest friends.
And I think a lot about this because, like you know,
these guys, we've all had very different lives. There are

(01:04:18):
I don't know if I'd start a company with any
of these guys, but there are attributes about each one
of them that I find really remarkable. And those are
the things that I keep in mind when I'm like,
one of the reasons I love staying close to you guys,
is I care about you. I love you like we've
known each other through so much. We've I we've done

(01:04:39):
a lot together, We've experienced so fucking much, and there
are still parts of you that just make me want
to get better. And for Adam, it was the relentless
commitment to his health and fitness, and I just I
couldn't help but think, God, I really got to get
my life right. And I started with the whole battery
of tests, Like I'm getting blood work, see he scanned,

(01:05:00):
doing all the heart like everything I can now and
really rigorously. I'm not a hypochondriac, but I'm like, I
need to get some basslines. I need to be checking
up on this. I need to actually be like making
like thoughtful visits to the doctor fairly regularly because and
as a dude, you're just like whatever, the cultures put

(01:05:21):
some dirt on it and you're fine. And like, that's
how I lived for forty years. And that was the
wake up call. And I feel like I owe it
to him. And so when I get up in the
morning and you know, I'm like, okay, I drag masked
the gym, I'm like, come on, show up, keep going,
man like, do it for Adam. It's a thing where
now it puts a framing on all the times we

(01:05:43):
get together because we know at some point it'll be
the last one that someone is going to be there,
could be us. And and so again we're not I mean, look,
we're still doing the same dumb shit like we were
at a brewery in Baltimore last time. Like it's not
who We're not that sophisticated about it. But I'll tell
you what, though we've gotten a lot smarter as we've
gotten older, I think we have gotten a lot better

(01:06:07):
telling one another actually how we feel, which is again,
this is a nuts thing for you. Talk to my
twenty year old self, like would you imagine yourself having
like thoughtful conversations about like life with your guys And
the answer would have been no, of course, not like
we're talking about football or video games or girls. But

(01:06:27):
that's been a nice part of getting older is now
there's more depth to this relationship, Like we have true,
true trust and intimacy, and we have this feeling like
I can literally tell this person everything because he's seen
me at my best and my worst, and like this
is my boy, right and that unlock gives me something
that powers me up for you know, however long it

(01:06:48):
is until I see them again. And when I think
about what is missing right now, I think about all
of the young men who don't have great role models
and can now access any role model they want, but
they are going to default to the junk food. And

(01:07:10):
that's not a judgment. It's the same reason I really
want to pick up the snickers right instead of whatever
the better choice is. There's an intellectual version of that
junk food that exists, which is not nourishing, it's not
actually helping you grow, and it's trying to fill avoid
you have a hunger for this thing.

Speaker 4 (01:07:27):
And I think men in particular the shadow of all
of the.

Speaker 1 (01:07:31):
Emphasis being put on women is that so little attention
has been put on our young men. And I would
love to see not attention taken away, but more attention
found to be placed on talking about young men, supporting
young men, because and there have been so I was
briefly a Kiva fellows. I volunteered for Kivo when I

(01:07:52):
left read it the first time. So it's in Armenia
working with entrepreneurs, and it was amazing. One of the
lessons they take away from that is is women entrepreneurs
anywhere in the world are a far better investment than
men because the money that you invest in them, that
they use to help build a business oftentimes gets reinvested
more often than not in the family, in the community,

(01:08:13):
versus if you do it for men, some of the
money goes to the family, communities, some of the money.

Speaker 4 (01:08:18):
Goes to the local bar, local establishment, whatever.

Speaker 1 (01:08:21):
Like Basically, investing in women in emerging economies just has
a bigger impact on society.

Speaker 4 (01:08:26):
And it kind of tracks.

Speaker 1 (01:08:27):
It's a generalization, but I think we're sitting here going yeah, okay,
that kind of tracks. But then you go a step
further and it's like, Okay, under duress, and this is
closely related. Women tend to endure a lot better than men,
and this is one of the reasons why when you
look at prisons, you look at terrorist organizations, you look

(01:08:48):
at when people are pushed to extremes disproportionately men that
end up not turning out well. So I think we
have an imperative here where if we have a generation
of young men who are feeling disabion, who are feeling demoralized,
who are feeling this insecurity, this deep, deep, deep pain,
like we all have an incentive to make sure that

(01:09:09):
they're getting that high protein diet of things that will
actually help them be better and actually give them a
path towards self improvement and give them a path towards
being successful, viable members of society, because unlike women, they're
not going to handle that well. And so I can
make the case from a a value standpoint, like, hey,
I think it's important to support these young men, but
I also would make the case just from a societal standpoint,

(01:09:31):
like it is in our best interests for public safety,
for all the things to make sure we get those
sort of that generation back on track. And I think
it starts with conversations like this between high profile men
who've had success in their careers, who can talk about
and normalize a lot of this stuff, because at the
end of the day, if we don't have those examples,

(01:09:55):
what else fills the gaps?

Speaker 4 (01:09:57):
And I don't like the alternatives that fill the gaps.

Speaker 1 (01:09:59):
And what's wild is, you know, I didn't really have
and I very much broke into tech and business and
learned a ton. And every time I keep going up
and I tell the guys this all the time. I
keep leveling up, right, and I keep meeting new people
and sort of getting another peak behind the curtain of
like how the world works or how business works and
all that stuff. And it's been eye opening because like,

(01:10:19):
their's shit. I would if I just could tell my
fifteen year old self and be like, don't do that.
That's stupid, Like there's actually a smarter way to do that.
And I hope to always keep feeling that to some extent.
But as I keep doing that and keep meeting more
and more folks, I have yet to meet one who
doesn't have this level of introspection and depth. And I'll

(01:10:42):
tell you it's most telling. Among the billionaires who are
now grandparents, men who have achieved everything you could hope
for in business, doesn't matter the industry who are looking
at their grandkids as a second chance because they didn't
get to or didn't want to, or weren't just didn't
all whatever we want, call it spending that time with
their own kids, and they're so grateful for that second chance.

(01:11:03):
But I keep looking at all these stories from men
who I really, really really respect, and the ones who
feel like they've had the most fulfilling life, all keep
coming coming back to human experiences they have with loved ones,
with family, And like I said, I got a much
smaller scale version of that with my own mom, who

(01:11:25):
never wanted for anything. And when you get to spend
time with folks who have a few years left to live,
it becomes very telling, and especially to do it in
my twenties, full of all that youthful vigor and vulnerability,
to get humbled and see someone who does not care
for anything other than the experiences she had and the
humans she loves. Bro That was probably one of the

(01:11:47):
greatest gifts she could have given me, was that perspective,
so that when I did find wealth, when I did
find notoriety, I'd be lying if I said it doesn't
affect me in some way. It's sure it affects me,
But I have never never gotten a twist about what
actually mattered. And I've never wanted for notoriety or fame.
I've never wanted for wealth. I've wanted for things that

(01:12:07):
helped me get more time with the people I care
about and make me feel like I am living a fulfilled,
like a fulfilled and purposeful life that's providing value to people.

Speaker 4 (01:12:17):
And that was a gift she gave.

Speaker 1 (01:12:18):
And so I don't know the more that we can
normalize this stuff, especially among folks, and I say men
in particular, about all people, but especially men who have
reached the highest levels. I want that eighteen year old
or that sixteen year old, that twelve year old to
be watching or looking and going like, hey, all right,
these guys are talking about stuff that feels like it
has substance, that has meaning and has purpose, and there's
still the ass kickers in the day job whatever it

(01:12:41):
is across the industry, like these things are not mutually exclusive,
and I just I want to see more of those
voices like yours get amplified because it's I think it's very,
very important.

Speaker 2 (01:12:52):
And I love that where you said that juxtaposition again,
the ability to be a killer in the workplace, a
brilliant leader, a powerful individual, and at the same time
being able to be empathetic, passionate, vulnerable. That's the power
is always in the juxtaposition, right. You look at it
in anything, whether it's a community, a company, an individual.

(01:13:12):
And I think a big part of that, going back
to what you've been talking about, is also seeing men's
relationship with their wives. Like I think that's a big
part that For years when we were talking about the
lack of role models or the lack of the ability
to look at something, it sounded like your parents had
a wonderful marriage and yeah, and demoed a beautiful connection

(01:13:33):
in front of you that you got to see. With
you and your wife having such busy lives, having priorities
both of you professionally, partnerships, places to be, travel and
then you've got kids, how have you found a way
to prioritize each other with the million things going on?

Speaker 1 (01:13:53):
That is at the crux of of I think every
conversation we ultimately have a couple, which is it's funny.
I'm very obviously high tech. She's very low tech. Sometimes
it literally comes down to calendaring and making sure, like
if I had my brothers, it would all be digital.

(01:14:14):
I finally got Serena to modernize a little bit, and
now we have a giant, like a dry erase board
calendar that sits at the dinner table where she'll put
in her schedule and then I have to go, and
usually I'll take a photo of it to send in
my admins.

Speaker 4 (01:14:30):
And then we'll write in mail.

Speaker 1 (01:14:31):
At least we have one shared space where we know, like, Okay,
Papa's out of town for this business trip, Mom's going
to this thing. And it is the hardest thing. It
is explicitly creating date nights. I mean, it's funny. It's
the same tactics that you'd hear any couple talking about
with a therapist about like, hey, what are the ways
to keep the relationship going, the romance all that stuff,

(01:14:51):
And it is definitely amplified in all kinds of ways
with a higher profile relationship. But the other reality is
so Serena's been working since she was a kid, right,
like tennis was not. I mean, it is a sport,
but like it's a job. Right, the amount of hours
she's putting in the responsibility as soon as she started

(01:15:14):
like playing, like playing, playing with tremendous responsibility. So you know,
I'm married to someone who has been working for thirty
five thirty six years and who had a childhood and
I think Serena would say like was a great childhood,
not a normal childhood. But now she's evolved her word

(01:15:34):
into you know, she's still got businesses. Just launched this
beauty brand, win shameless plug great brand, and so she's
still doing business things, she's investing, but she also loves
I mean, she's her class she's the classroom mom for Olympia.
She gets to spend so much of her time now

(01:15:55):
being an active and super engaged mom for her kids.
And I can't and I've told her this too, can
up but feel like this is a chance for her.
She's on the other side of it now. But to
live that life that you didn't really have, which was,
you know where your number one job as a kid
is just to go to school, learn things, hang out
with your friends. And who knows, if Olympia keeps going

(01:16:17):
with the tennis or the golf, we'll see. But she's
relishing that opportunity, and so that helps me a ton,
because right, that's ironically that's the thing that I grew
up with, the boring, typical suburban lifestyle that most people
in my position, myself included, will spend a lot of
their lives trying to maybe not get or run away

(01:16:39):
from because they want something else. And yet here she is,
having gone to the top of the mountain, achieved everything,
and that's actually the thing she loves most. And so
how we make it work, it's all it's banal stuff.
It's like making sure we prioritize. It's trying to figure
out and also decoding the differences. Obviously an interracial relationship,

(01:17:01):
I don't think that'll surprise anyone. And as a white
dude married to a black woman, you have a societal
golf right between us in terms of the ways we've
experienced our lives right in the American hierarchy of things, Like,
you know, we have very different lived experiences. You just
set us out obviously the fame, notoriety, career stuff, but

(01:17:21):
like even if we just operated this life as two
random people with our makeups, we'd have very different points
of view, experiences all that stuff, and it's probably the
hardest and best element to the relationship, where like the
table stakes are, we love each other, We've made two

(01:17:43):
incredible humans together. We will do anything. I mean believing
that too. She jokes that I'm like the psychopathic dad.
Like there's an Armenian dad meme in here, by the way,
Like we're very protective of our kids, but she's super mama.
So like we have things that we care so so
deeply about that we know we're on the same team for.

(01:18:03):
And so it's probably the best way of all the
ways to be checked on, like a blind spot. Let's say,
it's best to have it come from someone who you
know cares so much. And that's where the growth happens.
That's the tension. And so like if I say something
or do something and again nothing crazy here, but like

(01:18:26):
if I say something or do something and she's able
to shine a light on and be like, hey, did
you notice blah blah blah, or hey, this is like
bringing up these things to help me have better awareness,
because look, I got two black daughters. I want to
make sure I'm showing up the best way I can
for them. It helps because I still feel that pain
because I'm like, I'm not a racist, I'm not a
bad person. But then you sit with it for a second,

(01:18:49):
you're like, Okay, just hear this feedback, right, And it
reminds me it's just like going to the gym. You're
pushing some weight and you're trying to get to that
next level and it's going to hurt because that's where
the muscles tear, but that's where it grows back stronger.
And so I feel the same way when I take that,
I'm like, ah, Okay, fight the impulse, don't be defensive
and just listen and here and try to understand. And

(01:19:11):
I will say, though it's and I've talked to other
folks in interracial relationships, it is definitely there's a dynamic
there that creates new challenges or even I think any
cross cultural relationship creates those challenges.

Speaker 4 (01:19:23):
I bet I don't know if I was.

Speaker 1 (01:19:25):
I guess I'm a weird mid Atlantic guy, but the
difference is to me and even a white person from
Appalachia is going to have those cultural challenges, right, But
across those lines, that's where you get again with a
relationship built on love, you get this opportunity to say, okay, like,
let me try to learn and try to be a
little better. That I think helps. But like I said,
it's probably the worst part is the dynamic. There's a

(01:19:51):
reason we live in the middle of nowhere of Florida.
Like I love being here in La but like I
think we live in such a weird culture that you know,
the celebritization of things is just it's different. And one
of the things that we always wanted for our girls
is for them to have I mean, they're not going
to have a normal life, but to not be living

(01:20:13):
in it and to have the ability to do that
from you know, sort of the middle of nowhere Florida
has been probably the biggest secret weapon.

Speaker 3 (01:20:21):
What did you.

Speaker 2 (01:20:22):
What I love though, is the awareness you have of
the upbringing you had and how that's impacted you now
with you wanting the opposite.

Speaker 3 (01:20:31):
And how the upbringing.

Speaker 2 (01:20:33):
Yeah, And I love that awareness because it's such a
subtle point, but it's such a powerful one because it
sounds like you both accept why you're wired the way
you are. Because I think it could be really tempting
to project and hope that, well, you know, Alexis has
achieved everything too, so shouldn't we both just let everything

(01:20:55):
go and just be home with the kids, or you
to be like, well, you've achieved so much, we should
just be going for the next mountain, which I think
we do a lot with our partners where we reflect
what stage of life we're on. Like I remember when
my wife and I first met, I was ambitious and
driven and she was definitely the homemaker and curator. And

(01:21:16):
then as I've become more set in my world and
have more time, my wife's career has like really taken
off and she's really found her purpose and it's amazing.
But I just love watching her flourish. So even though
I have more free time to be able to spend
together now than I did eight years ago, I recognize

(01:21:38):
that watching her grow and watching her thrive is actually
the most inspiring thing. And now that just because I
have more time doesn't mean she has to adapt and
adjust around that.

Speaker 3 (01:21:46):
And so yeah, I find.

Speaker 2 (01:21:48):
It's a really but it's such a common thing I
see where it's like, I wish you were at the
stage of life that I'm at, and that seems to
be the hardest, most impossible thing to demand.

Speaker 1 (01:21:57):
You know, the challenge I had in previous relationships, the
general theme was.

Speaker 4 (01:22:05):
I knew I was super ambitious.

Speaker 1 (01:22:07):
I was very upfront about it, but it still doesn't
really land until three months in, six months in, nine
months in and you realize, oh, this guy is not
going to change. And it seems like a fun thing
for a little bit, and then at a certain amount,
like eventually push comes to shove and there's a gap
because they didn't get it. And again, I don't think

(01:22:31):
that's a right or wrong here, but it's an incompatibility.
And part of what attracted me so much to Serena
was the fact that I knew we would never have
this conversation about like, well, why do you have to
do this thing? Or why is this so important? Or
like why what do you mean you have to get
this done tonight? Like that could never happen because of
everything she had to do in order to achieve the

(01:22:53):
heights that she had gotten to. And so that to
me was already very appealing because I was like, Okay,
this is table stakes. I found someone who has clearly
even more ambition than me, who has achieved so much
and in a way so I don't know if I'd
say the same thing if I were an athlete. I
think that might have been harder. But to be with

(01:23:14):
someone like Serena, right, that's like literally one word, like
you don't even need to say her full name. It
is tremendously liberating because I know, and also because of
who we are and where we come from. Jay, there
is literally nothing I could do. I could one day,
god willing, I.

Speaker 4 (01:23:33):
Will be a billionaire. I will never run for president.

Speaker 1 (01:23:36):
But let's say I could be a billionaire who runs
for president, and I'll still be Serena William's husband or
Serena's husband. Right, I could be I could be an astronaut.

Speaker 4 (01:23:46):
It doesn't matter. It literally does not matter.

Speaker 1 (01:23:49):
And part of that is a testament to like where
she started, where she got, what she did, all those
doors that she opened, all those things. And so in
a way it's kind of liberating as a suite ambitious person,
especially in a society where like it's a meme just
to literally say, oh, that guy is comfortable being called

(01:24:10):
Serena William's husband. Now, candidly, if we live an ideal world,
no one is anyone's anyone, right, But I do appreciate
I understand why the Internet finds that really exciting and interesting,
But the bigger story here is the fact that if
you have this kind of partnership you're talking about, you're
able to let one another flourish at those things at

(01:24:32):
that time when they're ready. And maybe I didn't see it,
Maybe maybe I missed out on some great relationships earlier
because it wasn't there at that time. But at the
end of the day, one of the best parts, you know,
dating Serena while she was winning Grand slam after Grand slams,
breaking every record, doing all this stuff with Olympia and
her belly, I might add, you know, the pinnacle of

(01:24:54):
sports excellence, and then also seeing her now like making
cinnamon rolls for the second grade class, Like both of
those things bring me someonech s joy and frankly, I
love seeing the ladder more because it doesn't come with
all the baggage of being the public persona that you
just have to endure doing that job. And I know
she doesn't miss it at all for those same reasons,

(01:25:16):
and I think that's I don't know, that's been why.

Speaker 4 (01:25:18):
It's just, I don't.

Speaker 1 (01:25:19):
Know, been an easy transition for her, and frankly, been
a lot of fun to see this evolution for me.

Speaker 3 (01:25:26):
How did you meet.

Speaker 1 (01:25:27):
Six months into the Reddit turnaround, I was burnt out
and my head of comm said I needed to go.

Speaker 4 (01:25:34):
She was like, go to Italy and I was like what.
And she's like there was a speaking gig that wanted
me there, and I was like sure. I was like,
wait no, but this is a boondoggle, like there's no point.
We're not ready to like win over marketers. She's like,
just do it please, like you need a day or two,
just go. I was like, all right, fine, I go.
I flake out.

Speaker 1 (01:25:51):
On the conference that first day and I just find
a cafe and I started doodling, working on some sketches
for product stuff. I meet up with a friend of
a friend and very random, they just walked in and
they're like, hey, can we use the table. I'm like sure,
get some drinks. We're out that nine till like three
in the morning, and I get home hung over. The
next morning, I need coffee. Addicted, go downstairs. I say, sir,

(01:26:15):
breakfast is over, but if you want coffee, can go
sit by the pool. I go sit by the pool.
I take up my laptop and there's a table next
to me. The Australian. There's an Austraining at the table
tells me to move. He says, there's a rat at
the table. I say, I'm not afraid of rats. From Brooklyn.
I see rats all the time. He's like, I might
as a rat. You better leave and I was like, no,
thank you, I'm good and I was just working. And

(01:26:36):
then the lady next to him turns around.

Speaker 4 (01:26:38):
It's Serena and she's like, oh, you're not afraid of rats,
Like no, not. If you don't bother them, they won't
bother you. And she's like, oh, you're here for the
tech conference and I was like I am. She's like,
you here to see someone speak in particular. I said no,
I'm speaking. She was like oh, She's like, what's your company?
I was like Reddit and she she lied. She's like,
oh yeah, I read it. She had never heard of it.

Speaker 1 (01:26:59):
And we started talking and she said, listen, the rest
of my team was going to use this table, So
can you just move when they get here? And I
said no, but like they can join me and we'll
all just have breakfast and so exchange numbers. And I
saw her play later that night in Rome and that
was the start of it all. So it's breakfast at

(01:27:19):
a Hotel, the Cavaliery in Rome, great breakfast, wonderful truffle omelet, Okaserie.
If you want to get the Alexis special, it's the
truffle Omelet.

Speaker 4 (01:27:29):
That's a great, great omelet.

Speaker 3 (01:27:30):
I love it, Alexis.

Speaker 2 (01:27:31):
It's thank you for Sharon that it's beautiful to you know,
just even how you're speaking about your wife. And again
going back to that point, we were talking about having
positive conversations in that way of you know what a
healthy relationship looks like, challenges, ups and downs, difficulties of
course with any relationship. But you know, one of the

(01:27:52):
things that I wanted to ask you about that before
we get to the end of our conversation is this idea.
I mean, you were very humble a few seconds ago,
and it's beautiful to see you have reached. You know,
you've created something that in and of itself is a
word right Like it's like read, it is recognizable, used,

(01:28:12):
it's in pop culture, like, it's everywhere. Like you've built
something that is fully recognizable, let alone recognizable just everyone
knows what it is. And then Serena has this incredible success.
Of course, no need to explain. How do you both
think about defining success for your kids and the pressure

(01:28:34):
that obviously will naturally sit on them with whatever they do.
And then how do you think about defining success towards
your futures as well together and as individuals, because you've
both had an experience so much success.

Speaker 4 (01:28:49):
With our kids.

Speaker 1 (01:28:50):
It's the cliche you want to be happy, productive members
of society. I mean that, like i'd say, the other
wrinkle I'll put on there and I tell them in
biaus all the time, and I will tell Adira again, she's.

Speaker 4 (01:29:02):
Just one, she's doing her best. She's an active kid.
Yes it's six. I'll sit her down.

Speaker 1 (01:29:07):
But like whatever they want to do, I have zero tolerance.
I should say, we have zero toms for them not
trying their absolute best. Again, I know that seems cliche,
Like I don't even let Olympia say can't.

Speaker 4 (01:29:20):
We'll see how long that lasts.

Speaker 1 (01:29:22):
But I will not let her say can If she
says can't, I'm like, what was it? We don't we
don't say that word like that because I don't. I
don't even want her uttering that she can't do a thing,
like you can choose not to do it, but we
don't say that. We don't say that word. And I
try to reiterate to her. I want her to love
the act of trying.

Speaker 4 (01:29:43):
We used to do.

Speaker 1 (01:29:44):
There's a there's a YouTube channel. There's a few actually
that'll do these drawing classes. And I'm pretty good drawn.
I made the Reddit logo Snow, I drawed the pancakes,
and and during COVID, I was like, Hey, we're gonna
do drawing class. Pop can do our class. I can
do math in English, but art's more fun. So we're
gonna do our classes together. And you know, early on
she'd be like, wow, Papa, you're really good at trying.

(01:30:04):
And I'm like, do you think I was born this way?
And she was like maybe, And I was like no,
it's like Papa practiced. Papa drew a lot. And I
want even for mundane things like hey, we're drawing Princess Peach.
I desperately want her to take only one thing away,
which is even the stuff you think your papa is
great at, he sucked at when he started, Even the

(01:30:25):
things your mama is great at. Maybe she didn't suck
at when she started, but like she had to learn,
she was bad, she had to get better. You might
have some natural inclinations here and there for different stuff.
But I want to see her get comfortable with failing
and struggling and then improving. Getting her into golf has
been opened. I had never played golf, but Uncle Tiger

(01:30:46):
gave me some clubs for her, so I was like, letpe,
you got to play golf now.

Speaker 4 (01:30:50):
And we go to lessons every Sunday.

Speaker 1 (01:30:52):
And that actually has been a great sport for humbling
and for getting her comfortable with the process, because it's
such a brutal, hard sport and you have to get
comfortable with failure and messing up. And she'll still it's funny,
She'll whack at one hundred yards. I'll be so proud
of her, and then she'll totally whiff on a ball.
And once she got so upset she almost she almost

(01:31:13):
pulled the Serena. She pulled the club up and was
about to smash it. I was like, Olypia just casually
put the thing down. I was like, oh, you got
that Serena in you. But you see that, and you
see she's she's got that tenacity and she is so
hard on herself when she doesn't get it right. But
I need her to sit in that and soak that
up and get okay with it so that whatever she

(01:31:33):
does again, if she it changes every week. Veterinarian fashion designer.
Right now, she wants to be a singer. I'm like,
I don't care what it is, you just need to know.
I'll like what you love that Beyonce video. How many
hours do you think Beyonce spent rehearsing the dance moves,
rehearsing that song, singing over and over and over and over,

(01:31:55):
like do not get seduced?

Speaker 4 (01:31:56):
And it's crazy. I I don't know.

Speaker 1 (01:31:59):
I did not have anyone like sit me down and
tell me that that explicitly. And maybe it just ruins,
maybe just ruins life.

Speaker 4 (01:32:05):
We'll see.

Speaker 1 (01:32:06):
But I need her to know anytime she sees excellence,
the only reason she's seeing is because of countless, countless
hours of trying and failing and practicing that led up
to it that no one saw, that no one cared about.
And you know, with her mom as an example, she's
got the goat of a role model and she does
do tennis now twice a week.

Speaker 4 (01:32:25):
I think, I mean, she's got some good athletic jeans.
Let's be honest.

Speaker 1 (01:32:29):
No, but she might I don't know if she plays sports.
The goodness is her mom will be able to have
a conversation with her early on about just what it's
going to take and if she wants to do it,
God Blessed will support.

Speaker 4 (01:32:40):
Her, you know. But I I'm not worried. It's weird.
This is not a thing. Okay.

Speaker 1 (01:32:46):
When I was a kid, I used to be pretty
I don't want to say anti rich people, but like
I distinctly remember going to UVA and I went to
some good public schools in Howard County, Maryland, like they
were fine there, but I got to I played football
with kids who had free lunches and kids whose parents
were lawyers. So it's like I got exposed to a

(01:33:06):
pretty decent range of kids, which was great. And then
I got to UVA and I finally met like rich
people and it was so excited because I was like,
these kids are so soft. I was like this is
going to be great, like this is my competition, Like
this is phenomenal.

Speaker 4 (01:33:20):
And it tracked. But I now I'm like.

Speaker 1 (01:33:25):
On the other end, and I'm not trying to It's
not for sympathy here, but like there is I am
much more appreciative of the challenges that wealthier families have
making sure their kids have have it, have that grit,
have that whatever you want to call it. And so
that's something we're acutely aware of and mindful of and
hoping for. And like I, like I said, I want

(01:33:48):
to Limpy to work. Either it's got to be either
a retail job or food service, like some kind of
service job for sure, like high school. Like it's good
enough for Papa, it's good enough for you, Like I
need you to experience these moments and feel some kind
of connection, like you're gonna have You're gonna be fine, right,
But I need you to be a productive members of society.

(01:34:10):
I need you to be a good person. I need
you to know the value of a hard day's work.
And like I said, it's a weird thing to navigate. Obviously,
Serena doesn't have any kind of equipment for that and
everything her parents put up with in order to give
her that life, Like it's a wild perspective, but that's
it's something we actually think about and talk about quite

(01:34:30):
a bit. And the good news is, you know, at
least olympiad it is fun too. They're tracking to be good.

Speaker 4 (01:34:36):
Humans, which I feel like is number one, and that.

Speaker 1 (01:34:39):
If they can be good humans who are also productive
members of society, Like I feel like we're living the dream.
But there is that part of me that just thinks,
like you want you want to create just enough for
that strife to create that resilience and that ability to thrive.
And it's so ironic because if you look at so
many of the stories of excellence, there's always some version,

(01:35:01):
there's some part, there's something that happens that creates it,
and it's usually strife.

Speaker 4 (01:35:07):
And so it's like, on.

Speaker 1 (01:35:08):
The one hand, you don't want to, like part of
the reason you did the thing was so that your
kid wouldn't have to endure the thing, and yet you
still find yourself saying, God, I just kind of wish
they would have to endure some of that strife. But
it's that I mean, like, that's to me, that's actually
been one of the most satisfying parts of fatherhood is
seeing your kid fail and then seeing your kid get

(01:35:32):
it right. I get so much there's so much more
of a high from that than seeing my kid get
it right the first time. I really enjoy and I'm
not sadistic. I like it's it just feels like it
feels so much more satisfying because you're like, Okay, that
actually feels like a moment, will you There's some part
of you that just like a synapse fired and some line,

(01:35:52):
some dot in your mind connected with this other dot
where it's.

Speaker 4 (01:35:54):
Like, Okay, I figured it out. I couldn't do it before,
I can do it now and it could be right now.

Speaker 1 (01:35:59):
It's it's like multiplication and it's just being able to
start to see those dots really connect that I just
I love. It's very satisfying. It's like a Pokemon evolving
in front of your eyes.

Speaker 3 (01:36:11):
I love it, Alexis, it has been such a joy.
So honestly, this has been amazing.

Speaker 2 (01:36:15):
Just learnings from you from whether it's tech to AI,
to fatherhood, brotherhood to love is great.

Speaker 4 (01:36:25):
This is great.

Speaker 3 (01:36:27):
You're very kind. I appreciate that.

Speaker 2 (01:36:28):
But Alexis, we end every on Purpose episode with a
fast five for a final five, which means every question
has to be answered in one word or one sentence maximum.
So Alexis, these are your fast five. The first question
is what is the best life advice you've ever heard
or received?

Speaker 4 (01:36:45):
Be useful? It's ernold Schwarzenegger quote. Sorry, Arnold, I like it.

Speaker 2 (01:36:50):
Second question, what is the worst advice you've ever heard
or received?

Speaker 4 (01:36:54):
Oh?

Speaker 1 (01:36:54):
I didn't take it. I have to have taken it. No,
Paul Graham told me to get rid of the Reddit
alien and change the name to octopop. And I said, no,
I'm keeping snow and I'm going to keep calling it
reddit And that was a good It works out, Yeah, octopop?

Speaker 4 (01:37:10):
Would you all be using octopop right now? And he
wanted to change the alien.

Speaker 1 (01:37:14):
To an octopus. I'm like, Paul, come on, we're not
doing that. Brilliant guy, just not not great with the branding.

Speaker 2 (01:37:20):
No question number three, if there's any other business dads
listening that are struggling with the business and being a
dad and trying to manage it all, what would be
your advice for them?

Speaker 1 (01:37:31):
Aside from listening to my podcast? The goodness is there
are more avenues than ever because there are more and
more people talking about this than ever. What book were
we reading tonight? Like what are you most excited about?
And then when I'm on the clock for weekends in particular,
I really try to lock in and so it can
be whatever you need to do obviously your family is

(01:37:51):
going to have different prescriptions. But create those traditions, create
those routines. And that's one thing I would give advice
to myself at twenty about over again, when I had
more free time, when I had more youthful vigor, if
I had more discipline, I would have been ten times
more productive.

Speaker 4 (01:38:10):
And it shows up in sneaky ways.

Speaker 1 (01:38:12):
If if I had gone to bed at midnight because
I knew like my I was, the dimishing marginal returns
of my productivity were falling off a cliff and just
gone to bed, slept for seven hours, eight hours, and
then woken up and done the thing, I would have
done it in twenty minutes instead of staying awake for
another two and a half hours, Like, no, that's not.

(01:38:32):
Actually the best use of your time and discipline is
freedom and I never would have believed that in my
twenties or even in my early thirties, but becoming a parent,
that's the only way I'm able to do these things.
And that's not to say I'm perfect, But if you
can incorporate ritual routine even before you have kids, you
can be even better at what you're building. And then
once you have kids. It's it's kind of the only

(01:38:55):
way to do it. Frankly, I love it.

Speaker 3 (01:38:58):
Question before, how would you do find your current purpose?

Speaker 1 (01:39:01):
My current purpose is enabling a whole other generation of
entrepreneurs to do even bigger and better things than I did.

Speaker 3 (01:39:11):
I love that's such a very answer.

Speaker 1 (01:39:13):
And I mean it's it's also you sleep a lot
better at night because it's not your ass on the
line for every one of those companies too, So it's
a it's a blessed position of being.

Speaker 3 (01:39:21):
I love it.

Speaker 2 (01:39:22):
And fifth and final question we asked this to every
guest who's ever been on the show. The question is,
if you had to create one law that everyone in
the world had to follow, what would it be?

Speaker 1 (01:39:31):
Okay, this one I cheated, and I wanted to have
one prepared that had been a good idea, But I
think the best thing I came back with was a joke,
which was, you know, everyone should be able to experience
the joy of making someone they truly love happy. You
talked about this earlier. Again, it's not really a practical law. No,

(01:39:52):
I like that, but I have never felt more satisfied
or happy, or richer or taller or what. I've never
felt more any positive feeling you could feel than when
I get the unsolicited I love you, Papa hug from
my daughter. And again it doesn't have to be your daughter,

(01:40:14):
be anyone. But like those moments for me are like
black tar heroin. I am addicted to it. And so
when I think back, hopefully as an old man one
day and I think about, like, what are the things
that really really made me so incredibly happy, it's going
to come back to those moments. And so I wish
that for everyone as often as humanly possible. And the

(01:40:37):
irony is right. It usually doesn't cost any money. It
means time, it means intentionality, it means other humans, and
we're going to keep getting really good at making artificial intelligence.
And I don't want that to scare folks because I hope,
I really really hope and want to believe it gives
us more time for the human communing that far few

(01:41:00):
of us or not enough of us have a chance
to do often enough. So I don't know whenever you're
if you're breaking bread with people you love, Like I said,
these are all the things. Going going to a sporting event,
going to an Angel City match, you're you're enjoying these
moments of humanity with people you care about and uh
and and make an effort to tell those people, especially
men out there, dudes. Normalize telling the man in your

(01:41:24):
life that you love them, whether that's your father, your brother,
your best friend. You don't have to go buy a billboard.
You can if you want up to you, but like,
normalize having that conversation.

Speaker 4 (01:41:36):
You will not regret it.

Speaker 2 (01:41:37):
I love that, Alexis, honey and everyone business dad poscast
make sure you're subsided, right. And Alexis, I'm so grateful
to your parents. You know you carry them, Yeah, yeah,
you carry them.

Speaker 3 (01:41:50):
And their energy so well.

Speaker 2 (01:41:52):
You can tell how deeply rooted their love is for you,
and the love that they had for the world that
seems to be oozing out of you. So it's really
beautiful to experience that today. And I'm grateful that you
came and spend these couple of hours with me.

Speaker 4 (01:42:04):
Thank you so much. This was awesome, man, Thank you,
thank you, thank you.

Speaker 2 (01:42:08):
Thank you so much for listening to this conversation. If
you enjoyed it, you'll love my chat with Adam Grant
on why discomfort is the key to growth and the
strategies for unlocking your hidden potential. If you know you
want to be more and achieve more this year, go
check it out right now.

Speaker 1 (01:42:27):
You set a goal today, you achieve it in six months,
and then by the time it happens, it's almost a relief.

Speaker 4 (01:42:33):
There's no sense of meaning and purpose.

Speaker 1 (01:42:34):
You sort of expected it, and you would have been
disappointed if it didn't happen.

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Episode Transcript

Host

Jay Shetty

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