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– Hey, I’m Andrew Chen from Injuries and Horowitz
and today we have Justin Kahn, who is one
of our repeat entrepreneurs that we are very excited
to be working with on Atrium.
And so we’re gonna talk a bunch about
what is it like to be a repeat entrepreneur?
I think we were just going through the list.
There’s like five different companies on there
and you’ve learned a ton from every single one.
And so we’re gonna do a series of sort of compare
and contrast across quite a number of topics.
But as a very first step,
I think it’d be awesome to have Justin talk about
some of the companies that you’ve been involved in.
And I know the company you were running when we first met
where you were running around with a camera on your head
is not actually even your first one.
There’s one before that called Kiko.
So why don’t you talk about Kiko first?
– Sure, yeah.
So I’ve been an internet entrepreneur here
for the last 14 years since 2005.
Our very first company was called Kiko.
It was kind of like Google Calendar,
but it came out one month before Google Calendar came out
and wasn’t really that good when I’m honest about it.
And so that company didn’t work out super good.
We ended up fire selling it on eBay
after several failed acquisition attempts
with the Sullivan Valley players.
And then after we did that, we started another company.
This one was even less well thought out than Kiko was actually,
which was the idea was we would create our own
live video reality TV show on the internet.
I do think that tapped into several things
that were in the zeitgeist
that actually have become popular now.
But unfortunately, we as talent in our own show
were not very entertaining and not very popular.
And so we launched this live streaming show.
We called it Justin TV.
‘Cause I was the only one in our four founders
who was stupid enough to put the camera on his head
and be like, I’ll make myself the subject of this show.
And you literally wore, I remember you wore a backpack.
– Yeah, so this was 2007.
So it was pre-iPhone, pre-good cellular internet.
So we had this computer in a backpack
with like multiple cell phone modem connections.
And we hooked it up to a camera.
So there was a camera, this computer virtualized the video
as a webcam, basically sent it over to the server.
And then we had this very hacky way of streaming it out
to the millions of people watching,
actually not millions, hundreds,
but the people who were watching at home,
they were following along, it was actually pretty fun.
They could text, we put our number up there,
they would text me, usually fairly offensive things actually.
But then eventually we launched this show,
people started coming because they were like,
what is this guy doing, this is crazy.
They were like, you’re very boring, I hate your show,
but I want to create my own live video stream.
So how are you doing it?
And then the light bulb kind of went off
and we said, aha, let’s create a live video platform.
And that became Justin TV, the platform.
And then after that, we ran that for a couple of years,
I’ve condensed it because it’s a very long story,
but we raised a bunch of money,
ran it for a couple of years,
hit the nuclear winter of video startups
where all the other video startups in Silicon Valley died.
We were pretty scrappy and survived on like a ramen budget.
Eventually decided we needed to pivot to some new ideas.
And from there we incubate a few ideas internally.
One of them was a video app called social cam,
which we spun off and eventually sold to Autodesk.
And another one was a site that we,
my co-founder really thought of,
which was the idea was focus on,
let’s focus on the video game related video on our site.
And that became Twitch, which kind of grew and grew and grew.
We eventually pivoted the entire company to Twitch.
My co-founder Emmett was the CEO of the company
and eventually sold it to Amazon for $970 million in 2014.
About five years ago.
Along the way started some other companies
to start this company called exec,
which is in the errand running/home cleaning space.
It’s kind of like a handy year home joy.
We actually ended up selling it to handy,
which through an act of God sold to Angie’s List this year.
And then more recently,
I’d been a partner Y Combinator for a couple of years
and then incubated a few companies.
One of those was this video Q&A app called Whale.
And then just fast forwarding all the way
up till the present day,
decided I want to really put all my eggs back in one basket,
precariously thrown around basket.
And so I decided I’d start a new company.
That idea was Atrium,
which is a technology enabled law firm for startups,
really trying to solve all the problems that I had
as an entrepreneur when dealing with legal.
To make legal faster, more price predictable,
more transparent for me, the business owner,
you know, the business manager.
And that’s what we set out to do about two years ago.
It’s going pretty well.
We’re serving a bunch of startups here in Silicon Valley
with all of their needs.
And it’s been great, but I’m sure we’ll get to that.
– Awesome, yeah.
Well, I think one place where I’m going to start on this
is a lot of the advantages of being a repeat entrepreneur
are that, you know, you can raise more money
and there’s more, you know, maybe easier to recruit talent.
And there’s, you know, there’s all these advantages
that kind of, you know, come along with that.
One of the disadvantages I find ends up being that,
you know, there’s so many like distractions, right?
Like you could, there’s a million different things
you could do.
There’s a lot of things pulling at your attention.
I’m really fascinated by, you know, your movement
from going from YC and an incubator
where you can maybe kind of dip into a lot of little things
versus kind of putting all your eggs in one basket
and trying to like start a company.
Like, you know, to talk to us about that,
that kind of decision.
– Yeah, that’s a great question.
So once you become, you know, successful in some way
in Silicon Valley, whether that’s, you know,
you’ve been the executive at a company
that’s, you know, rocket ship unicorn
or you’ve started a company, you know,
the world opens up, right?
People want you to be a VC.
They want you to, you know, work on projects with them.
You can start any company that you want,
which is great, right?
But there’s just paradox of choice
and focus can be a huge problem.
I know for a lot of friends of mine, it has been as well.
As an investor, as a partner at YCom,
there were some parts I really liked.
You know, I loved helping early stage founders out
and like really working with them on these problems that,
like I felt like for five to 10% of them,
it was like life changing, right?
Like me helping them out in a way,
I came up with some great idea
or helped them at a critical moment.
That was life changing.
But then there was a large majority of them
that probably could have been listening
to a YouTube video of me or this podcast
and like you get the same information, right?
And so I didn’t feel like the feedback cycle
was fast enough also as an investor.
And I didn’t really feel ultimately,
like after the first couple of years
that I was continuing to learn and grow.
And you know, I’m still in my 30s.
I was like, I need to do something
where I’m going to be forced to grow.
And really the number one vehicle for personal growth
that I’ve ever experienced in my life has been startups.
You know, so I went back to when I knew
and I really decided that in order to grow as a founder,
you know, we had a pretty big outcome with Twitch
and I’d seen a lot of different things
in order to really grow to the next level.
I would have to do something that potentially
could be even bigger.
And so I really felt like it deserved,
that deserved my full attention.
And so that’s kind of how I decided.
I don’t necessarily think it’s the right answer
for everyone because what I didn’t mention
was that I had selective memory at the time
and I forgot just how painful starting a startup could be.
And so for the first couple months of atrium,
I was like, oh man, this is a dream.
I’ve like finally leveled up.
I learned all these skills.
I’ve like, I made it as a founder.
And then reality boom set in.
And of course there were nothing ever goes according to plan.
There were pains, there were struggles.
And that was, you know, that’s part of the journey.
But then the good part is, of course,
when you experience pain, that is a catalyst for learning.
And so I really got what I wanted in the end,
which was forced to learn.
– Right, that’s great.
And I know one of the big differences
among some of the companies that you started
in the past versus atrium,
and something that you’ve talked a lot about is,
you had this sort of succession
of very like consumer oriented startup,
sort of like watching other people play video games.
Like that’s as consumers, basically.
And so very interestingly, atrium is a B2B thing.
And why did you choose B2B?
Was it just for novelty?
Was it just to push yourself?
Or do you think that there’s something different in mind
that maybe takes advantage of some of your new found skills?
– Yeah, well, Twitch, I guess, is really the,
it’s like the ultimate consumption thing,
’cause it’s you’re consuming someone,
consuming video games.
– Right, right.
– For me, I felt like maybe this was an analysis
I’ve done like retroactively,
but I think I’ve had this discussion
with a couple people with multiple time founders.
And when you’re an early stage founder,
when we started Kiko and then Twitch,
when we started Twitch, we were like,
or just in TV, it was like we were 23 years old.
And we had no skills.
I never had a real full time job in my life.
And even though we were programmers,
we were like new college grad programmers.
We were not good.
We were horrible managers.
We basically had nothing going for us.
When you have nothing going for you,
except for your like willing to put in hard amount,
like long hours on a lot of blood, sweat, and tears,
then you should focus on things that are like,
where there’s a lot of market risk,
because ideas where there’s market risk,
you can potentially win those, right?
Now, as someone who has abilities and skills,
where I’ve learned skills over the last 14 years,
you wanna focus much more on like execution risk things.
And so I felt like B2B startups
are more about execution risk.
I felt like this legal market,
particularly was already a big market,
and you just have to figure out
how to do it 10 times better, right?
And I felt like I had a roadmap
for how to do that in my head.
And so that’s why I felt that this was a better use of time.
‘Cause some of the consumer startups that I had incubated
and played around with post Twitch,
actually it was really hard to find product market fit, right?
Like, I don’t have any advantage
in finding product market fit with a consumer app
more than the 22 year old Justin.
– You might have a disadvantage.
– Yeah, I probably have a disadvantage
’cause I’m like already more set in my ways.
I’m like less in tune with the culture.
I’m like, I don’t know what the kids are doing.
So, with the Justin of today, invent the Twitch of today.
Like, I don’t think so, right?
Like I’m an old guy now, man.
(laughing)
It’s game over for me.
– I wanna unpack this market risk, execution risk.
‘Cause that’s obviously,
it’s such an important distinction,
but very colloquial, kind of in our understanding of it.
What do you mean by market risk
and sort of maybe new entrepreneurs
can have an advantage in market
and tackling something with new market?
How do you know if an idea has a lot of market risk?
– Sure, that’s great.
So, Twitch and H&M are the perfect examples, right, almost.
So, Twitch, it’s like when we started,
when we pivoted Justin DV to Twitch,
or even Justin DV is a good example,
but Twitch is the best one probably.
When we pivoted Justin DV to Twitch,
nobody believed that there would, this was a market, right?
No one believed, no investors,
very few of our even internal employees believed,
and even the founders were skeptical.
Emmett deserves the credit here, ’cause he had belief,
but a lot of the other co-founders were skeptical.
I’m like, does this exist as a business?
And so, the good part is that the competition there
was very low, right?
There weren’t experienced entrepreneurs being like,
this is gonna be a huge business, we should compete.
So, really it was, the entire thing was market risk
and figuring out, do we have product market fit,
how do we build product market fit?
– ‘Cause in that case,
you’re trying to be the first in the category.
There’s no substitutes really.
You’re watching someone else play street fighter
at the arcade, that’s a substitute.
– Exactly, you have a lottery ticket, right?
– You have a lottery, yeah.
– It’s a lottery ticket, and if you pivot a bunch of times
and listen to your customers,
you might be buying more and more lottery tickets.
But your lottery tickets are just as valuable
as the experienced entrepreneur’s lottery tickets
that he’s buying.
So, he’s a fool to play that game,
and I don’t think you see as many experienced entrepreneurs
playing that same game.
Whereas, with execution risk businesses,
my lottery ticket now is way bigger than the guy
who’s like the 22-year-old Justin, right?
So, for a B2B startup, I know, oh, I can attract talent.
I can hire a sales team.
I can raise capital.
And so, it’s a lot more, for something
where it’s very established that that’s gonna be a business,
or some business is gonna be in there,
it’s like he’s stupid to play against me, you know?
– Right, that makes sense.
Well, you know, and I always find it funny
that in the consumer startup world,
that if you look at the last kind of decade of hits,
if you were to tell people, oh, yeah,
the biggest hits are gonna be this app
that lets you get in strangers’ cars,
this app that lets you stay at someone
you don’t know’s like house,
an app where you swipe left and right
in order to meet people on the internet,
and an app that lets you watch other people play video games.
You would be like, that’s the craziest list of
billion-dollar companies I’ve ever heard.
And yet, that that is actually how consumer
the internet actually, you know,
the ecosystem unfolds, it’s insane.
– It takes a lot of people who have nothing to lose
to discover those ideas, right?
– Right, yeah, and so one of the things,
one of the clear advantages in all of this
is that, you know, let’s talk about fundraising,
and the decision on whether or not to raise
a bunch of money out of the gate,
versus doing the kind of, you know,
ramen profitable, you know, cockroach thing, right?
That’s sort of like, you know, one common contrast,
and then obviously you had a very unique
fundraising strategy as well.
So maybe talk about that decision,
and then kind of how you ended up pursuing it.
– Look, I’m not convinced that raising a ton of money
out of the gate is the right strategy.
You know, the Silicon Valley is littered
with dead bodies of these companies,
you know, the Juceros, and the Kools,
and like all these companies that have raised
a ton of money, and then like they,
when you have a ton of money, you spend a ton of money, right?
Now there’s other companies like the Jet.coms
that, you know, they made it work.
So, you know, I’m not convinced it’s the worst strategy ever,
but I’m not convinced it’s the best.
But for me personally, you know,
where it’s an execution risk business,
I’m too rich to like, fuck around with the like,
you know, okay, I’m just gonna do a seed round,
and like, and just like, take a long time, right?
Like for me, speed to market and execution
was really important, and I felt also like
this market really supported and required it,
because, you know, it is the legal space,
there is, you know, so a lot of value
in making sure that the clients and the talent,
the attorneys talent, and other legal providers,
like, think this company’s gonna be around, right?
So that’s very important.
And so, you know, this is a strategy,
I don’t necessarily recommend to anyone
who can raise a ton of money that this is the right strategy,
it’s just the strategy that we picked.
In terms of the tactics of like how we did our round,
especially our Series A, you know, my idea was,
because VCs are kind of naturally adjacent to legal,
right, like, for example, when you fund a company,
they need someone to help them on the legal side
with all of the, you know, paperwork
and the execution of that funding round.
We felt like getting a lot of VCs on our side
would be a good tactic, and so we ended up going out
and raising money for our seed round of, you know,
over 90 different investors from all over Silicon Valley
because I felt like it would be really good
to have those investors on our side
and recommending Atrium as a channel partner,
and so that was our tactic there.
– Right, and I think it’s something where,
you know, to your point, if something
that you’re working on is primarily execution,
then that means that, you know, you can,
there are times and places where you can use money
to solve it versus, it seems like, you know,
part of the market risk thing is it just, you know,
to your point, it sort of lets you buy more lottery tickets,
but it may not accelerate the process
of actually doing it, right, and so I think that,
that sort of feels like one main difference,
and then the other one is, you know,
that just to build on what you’re saying is that
if you are in an industry where trustworthiness
is really important, then being well-capitalized is key,
you know, the same way you wouldn’t, you know,
if you’re gonna, you know, for example,
you know, build a FinTech startup where, you know,
you’re gonna ask consumers to trust their money
with you, you know, like you wanna be legit,
you wanna be well-capitalized, you wanna have, like,
you know, super strong executives
and board members and investors, and like,
and that’s a strategy, kind of, that’s a little bit,
kind of, like, self-perpetuating as well.
– Yeah, that’s a great example.
If you’re gonna build, like, a new bank, right,
like an online, or like a mobile-first bank,
which is, I think, some people are doing,
would you wanna raise, you know, $1 million,
or $1 million seed round, or a $5 million seed round,
or a $50 million series A out the gate?
Obviously, if it’s available to you,
you want more money, ’cause you know people need banks, right?
It’s just a matter of can you do it better, right?
That’s a perfect example, and there’s, you know,
there’s many others here in Silicon Valley.
I think we’ve actually shifted more
as the cycle has changed over the last 10 years,
the tech cycle.
We’ve shifted more to these execution-risk startups,
and so, you know, you’ve consequently seen,
I mean, it’s a chicken and egg thing, really,
what came first, but like, you’ve seen these more and more,
like, bigger rounds, I’d say,
that are supporting these companies.
– Well, you know, one of my,
one of the partners here, Chris Dixon,
has talked about the idea that, you know,
if you have a set of problems that has not been able
to get solved and improved in, you know,
the 20 years of the modern internet,
then maybe all the techniques that we pioneered
in the last, you know, decade plus,
like being asset-light and just throwing software,
and just shipping really quickly, and being really lean,
like, maybe those techniques don’t work for a reason
in healthcare and fintech and legal services
in real estate, and like, you know,
some set of those things, right?
And so then, very quickly, you have to think,
okay, well, you know, if those techniques don’t work,
otherwise, it would have,
someone would have tried it already,
it would have, it would have sort of, you know,
a little bit like efficient market hypothesis.
– Yeah, that’s the thing.
– It would have kind of like happened already,
like, maybe you need a foundationally different approach.
And so, I think that is actually one of the reasons why
there’s more of these like, quote unquote,
full-stack startups that are going after
these really, really difficult areas.
‘Cause like, you know, otherwise,
you wouldn’t be able to do it.
– Yeah, well, running experiment right now.
– Yes, yeah, right, no, I think that’s right,
I think that’s right.
So, you know, one of the fun topics,
one thing that I have a tremendous amount of respect
for you on is you’re very, you know,
you’re always on the leading edge,
thinking about, you know, self-improvement,
how to sort of, you know, your own, you know,
personal performance at work, you know, at home, et cetera.
And obviously, one of the big things about, you know,
running a company is that it is enormously stressful.
Right? – Yeah.
– And so, talk to us about like, you know,
when you were a first-time entrepreneur,
kind of Kiko, Justin TV, you know,
how did you think about, you know,
managing the stress of, you know, running a company?
And what was your approach there?
And then let’s talk about kind of like,
the new and improved Justin now, you know,
kind of 10 years later.
– Yeah, so in the early days, you know,
10 years ago, I was not doing anything
in terms of like improving myself.
In fact, I think I used to think about people’s attributes,
maybe not your skills so much in terms of like, you know,
it’s your skills at programming or stuff like that,
but more of like your attributes.
Like, I don’t know if you ever played Dungeons and Dragons,
but when you create a character in Dungeons and Dragons,
you roll this like 20-sided die and, you know,
your strength, it’s like 14, your intelligence,
you roll it and it’s six or whatever,
and that’s what you have, you can’t change it.
And so I felt like people’s attributes
were kind of like that.
And so I never worked on that very much,
self-improvement stuff outside of, you know,
like yeah, I became a better programmer
’cause we were programmed, you know,
but I didn’t work on things to like make myself,
I don’t know, smarter, right, or harder working,
or like awake more hours of the day, right,
like alert more hours a day or anything like that.
So it was very happened, you know,
everything was kind of accidental.
Like we would, you know, I was not dealing with stress
well at all.
If there was a problem in the company,
I would be very emotionally avoided to it,
or I would like drown my sorrows in like alcohol, right,
which is not a very good coping mechanism at all.
And so, and then like, you know,
in terms of even just down to like
what we were like eating at lunch,
I was, you know, we were talking about this this earlier,
but I would, we would have like pizza every day
at lunch at Justin TV, and then I’d like fall asleep.
Like I’d go into like a carb comb,
like a carb comb in the afternoon, like every day.
And so now more recently, like with atrium,
it’s been a tremendous vehicle
for my own personal discovery,
because I experienced the stress again.
You know, I was like, oh my God, it’s stressful.
Again, this is crazy, why is it so stressful?
And so I started looking for ways to deal with that,
and I really, I mean,
if I had a number of things that started working for me
after I started really exploring it,
a number of things that started working for me
starting last year, you know, everything from,
friend of mine recommended a daily gratitude journal.
So I’ve just been doing that every day,
writing this gratitude journal, five minute journal.
You write down the three things every morning
that you’re grateful for.
And that seems like a very simple thing
and kind of hokey, actually, when I first heard about it.
But what I realized was it helps recontextualize
all the ups and downs that you experience
as an entrepreneur, especially, I mean,
the downs really, like throughout the day,
they’re not as big of a deal,
because in the morning, you’re writing down,
like, wow, I have this opportunity.
You know, I remember the day we came in and pitched,
you guys here, I wrote my gratitude journal,
I get to pitch, you know, Andrewson Horowitz.
That’s amazing, right?
Even whatever happens, that’s an incredible opportunity.
It puts me in the top 0.01% of people in the world
without opportunity, you know?
So that was like pretty amazing.
And then, you know, every day there’s something,
like if you really think about it,
there’s so many amazing things that happen to you
as a human being here in Silicon Valley.
Even just like actually one thing I think in the morning,
oftentimes it’s like the supply chain,
the global supply chain to deliver coffee
from like around the world,
so that I can grind up fresh coffee
and like a pour over in my Chem-X in the morning.
– Right.
– That’s amazing.
– It is amazing. – Like if you think about it.
– It’s totally amazing. – Yeah.
– Right.
– So the gratitude journal really working for me.
And then another thing–
– You’re still eating pizza for lunch every day?
– Yeah, so diet, another thing, I stopped eating pizza.
– So, entirely?
– No, well I started eating a ketogenic diet,
which is a high-fat diet,
but really the reason for me is like,
I just don’t get as tired in the day anymore.
And so that’s been really helpful.
And last year I was experimenting,
I did like some one meal a day, days,
you know, like four days a week.
Some of these weird like Jack Dorsey diets,
kind of Jack Dorsey light or whatever,
but it’s been good for me.
You know, you had to do what your body feels like,
it feels good.
So, you know, that’s some diet and exercise,
pretty religious about exercising,
you know, try to do something every day during the work days.
– Yeah.
– And then the last thing that was really big
is meditation for me.
Start off just with headspace, you know,
I’m not the type of person that people, you know,
assume would be a heavy meditator
or very introspective or anything like that.
But for me, just like starting off with headspace last year,
and then now I’ve been doing transcendental meditation,
which is kind of what Ray Dahlio talks about
and the principles, that’s worked really well for me
to just be more present during the day in my life.
It’s pretty amazing, amazingly profound effect.
– I feel like your Twitter stream
is part of your gratitude journal.
– Yeah.
– ‘Cause I read your Twitter stream and I’m like,
oh, this is like very philosophical.
You know, it’s not like just pulling out like,
oh, here’s a blurb from the latest S1 or something.
Like you’re like, you know, you’re like sharing ways
that the startup community can, you know,
to think about themselves.
– Yeah, the way I think about it is like,
if you want something to be part of your identity,
talk about it.
If you want to learn something, teach it.
You know, and I really believe that.
So for me putting out, you know,
what I’ve been doing on the mindfulness side
and for myself to be more emotionally kind of stable
throughout the days and weeks and months,
as a startup founder, that’s been really valuable to me.
So if I can spread that to other people,
it’s gonna help reinforce it as an identity for me,
but it’s also gonna hopefully help those people as well.
– Right.
You know, one thing I’ve been working on a lot as well,
the last thing I’ll say is just working on realizing
that your attachment out in the very early days
of Justin TV and Twit, Kiko and all these companies,
I had a huge ego attachment to the outcome of the company.
– Yeah.
– Right, my identity and the companies
were like very intertwined.
And more recently, I realized that was the same
at Atrium actually.
Like again, I was like creating that same pattern,
but it was like, it’s a very unhealthy pattern.
So what I realized was I needed to start telling,
reminding myself that no matter what happens
with this company, I’m not gonna be any happier
or any less happy in the long run.
There might be a short burst of unhappiness
if it fails or happiness if it succeeds amazingly,
but you’re not gonna get any happier.
Really, if you’re relying on outside things,
external factors to drive your inner happiness,
you will always be disappointed in the long run.
And the funny thing is I’ve actually run the experiment,
not an A/B test, but a linear experiment on that,
because we’ve had more and more success over time.
Like we started off really paying ourselves,
I think with Kiko, $7,800 a month,
but we only paid ourselves every other month.
And so then we raised funding for Justin D.V.
and we were able to make a little salary,
then we became profitable, we made a lot more,
and then we sold one company, then we sold a lot of companies.
And so we kind of ramped over time.
And after the basics of Maslow’s hierarchy of needs,
we’re taking care of, I felt like I could go out to eat.
I don’t know if that’s on one of those Maslow’s
hierarchy of needs, but after that basic thing,
I could afford to go out to eat.
None of it never mattered.
It never made me sustainably more happy.
And so just reminding yourself of that
and trying to remove those attachments in your mind,
it’s easier said than done,
but having that as like an active practice
has been really important to me.
– Let’s talk about mentorship as part of that, right?
So when you’re building Kiko, Justin D.V.
and you’re a first time entrepreneur,
there’s a lot of experienced people
who are kind of like, go ahead of you in the thing.
And so that’s fantastic ’cause you can learn a ton.
Would love to hear kind of who you thought of
as your kind of lifelong mentors,
people that have helped you for a long time.
And then the other problem that’s super interesting is,
then you start atrium and you’ve had
some major successes behind you.
And then in some ways, the number of people
you can learn from is a much smaller pool
and sort of like, how do you kind of curate your mentorship?
Maybe how has it changed over time?
That’s a broad topic, but would love to hear your opinion.
– Sure, absolutely.
So like the best part about Silicon Valley, in my opinion,
is that there are people here who have done it before
who are willing to help you.
That we would never have made it here even day one
without people who helped us when it was like economically
bad, waste of time.
We weren’t like, didn’t look like a hot prospect
company or anything, right?
So those people will, Paul Graham, great example,
founder of Y Combinator, Paul Buhay,
who is like a partner in Y Combinator,
but they invented Gmail inside of Google.
These are people who invested in us very early on,
mentored us very early on and helped us out.
And that was pretty amazing.
And really that ethos perpetuates itself,
because then as a partner in Y Combinator,
even today as an entrepreneur,
where there’s like lots of conflicting,
competing interests for my time,
I always make sure to spend a little bit of time
mentoring other startups,
because it’s kind of like a pay it forward thing.
And you do the thing that people did for you
when you were younger.
– One of the really obvious sources of mentorship
is actually peer mentorship, right?
And some of the folks that kind of came up with you
at the same time and ended up running
really interesting companies on their own.
And I know they all live in DeBose with you
in San Francisco.
Talk to us about some of your friends
that you consider your mentors.
– Yeah, so it’s great to have friends
who are kind of doing the same path in a lot of ways,
but are one or two steps ahead of you.
So it’s still a case.
Obviously Emmett, my co-founder who’s still running Twitch,
it’s over a thousand people.
I think it’s like 1500 people or something like that.
My brother, who’s COO of Cruise,
co-founder of Cruise, the self-driving car company.
And they’re like over a thousand people.
And Steve, the founder of Reddit,
they’re like 400 something people or whatever.
So, you know, seeing what their problems are,
you know, obviously the problems are always the same,
actually the problems are always like,
I don’t have the right alignment among my team
and I don’t have the right executive team.
It’s usually some variation of those things.
But, you know, hearing it from the horse’s mouth
is super helpful in terms of making decisions for me.
And then, you know, even outside of DeBose,
sometimes I venture into Soma
and having some of those, you know,
kind of early YC founders who have really made it,
you know, like the Drew from Dropbox, for example,
and just knowing like how do they think about
every, all those things, executive hiring, et cetera,
it’s been really helpful, helpful to me.
So, luckily here at Silicon Valley,
I have a lot of great resources.
And the last thing I’ll shout out is,
I have this new executive coach, Matt Mocharri,
who’s like amazing.
This guy is the guru.
He’s, you know, mentors a lot of different fast-growing
startups around here.
I just talked to him for like a 360 thing.
– Yes. – Yeah, yes.
– This guy. – Yeah, that was great.
– Incredible, highly recommend, can’t speak,
he’s like changing my life.
So, I feel like he’s an angel sent down from Heaven
to teach me, finally, after 14 years,
how to like manage a system.
And I’ve learned a lot from him, so.
– That’s great.
– Those are kind of three sets, you know,
executive coach, the peer mentors,
and then kind of those early stage mentors
that I had back in the day.
– That’s great.
And I know one of the topics that you must end up
talking about often is that when you’re building something
that has a little bit more just execution risk,
you know, you’ve raised some real money
to kind of get started.
A lot of it ends up being sort of like organizational,
complexity, company culture.
I know this is the big, big, big, big area focus for you.
And that’s something that is very different
when you’re trying to build something for the long run
versus when you’re kind of just trying to find
product market fit, and it’s kind of like 10 people,
and you’re just like, is this even going to make it?
Like, let’s not even work on this.
– Yeah.
– So talk to us about kind of how your approach has changed
on building the company and your leadership style.
– That is a great question because it’s something
I think a lot about.
So I had never thought before a couple of months ago,
and this may sound stupid in a way,
but I’d never thought, what is the kind of company
that I want to show up to work at?
So 14 years later, finally thinking about it.
But the real answer is like, when you’re a 22 year old,
just starting your company, or you’re in Silicon Valley
and you’re thinking funding rounds and exits,
you’re always thinking, what’s the next milestone?
Like, how do I just claw my way desperately?
However, whatever it takes, how do I get to that
next milestone?
It’s do or die.
And for some, you know, oftentimes it is do or die.
You don’t have the luxury, oftentimes, of thinking
about what kind of, or you feel like you don’t have
the luxury of thinking about what kind of company
you want to build culturally.
And so, I started at Atrium actually very much
in the same way, but like, what are the metrics milestones
we want to hit?
What’s the next metrics milestone?
What do we need to get to for a Series B
or a next round of funding?
And so, the problem with that was that a year in,
I realized, oh, shoot, I need to like,
there are like a lot of things that I’ve neglected
that are actually affecting our ability to execute.
And the number one thing there was,
what’s the culture going to be?
People didn’t know, like, what’s the alignment aspect
of like, what are we building?
What kind of company are we?
Who are we?
What are we building?
And then, what’s the culture?
How are we being intentional about it?
So, we did a lot to work on that,
ran through a collaborative values process over a year ago
where we brought the whole company together,
figure out what we care about.
And then more recently, I’ve been thinking about,
after a lot of this self-work in terms of making myself
feel kind of consistently good every day
and move my attachments to the outcome,
I’ve realized there’s a set of principles
that I want to implement at the company.
And that I think that execution will flow
from those things, right?
If we build a company that has a high empathy
for each other, where we have care for each other,
where people are very collaborative,
where people feel like the locus of control
for what’s happening is inside of them,
instead of outside of them.
Things are happening through them, not to them.
I think that all the execution will actually flow from that.
One of the things I never understood before,
which I feel like I really understand now,
is that saying that culture eats strategy, right?
I felt like I had very good strategy with Atrium,
but I forgot about culture in that first part of the company,
and now I realized how important it is.
So one of the things I’ll say that we’re doing
is recently I read this book called
“The 15 Commitments of Conscious Leadership,”
which is an amazing book,
but it’s really about building a certain type of company,
what the authors call a conscious company.
But I would centered around that locus of control question.
Do you have radical responsibility
for what’s going on in your life, in your company,
regardless of who you are?
And read that book, and I realized this is the type
of company that I want to work at.
It’s a company populated by team members
who really believe in these principles.
And so we’re kind of going through a process
of trying to implement that at our company.
And really culture is one of the highest.
It went from something that I didn’t prioritize
to my top priority.
– Yeah, well, and I think it’s really interesting
because you’d started Kiko out of school, right?
And so unlike some folks who maybe,
they go and they work at Google or Facebook or something,
and they maybe have a template
for the company culture they want to create,
this is something that you kind of had to learn
and adjust over many, many kind of company iterations
of various companies that you built.
– That’s right, we had never worked at a place
with good culture or a culture, right?
Because we had always worked at our own company,
so we were just making it up as we went along.
When you’re not intentional about your culture
or type of company you want to be,
then the culture ends up being the accidental collection
of good and bad choices and personality quirks
and good and bad behaviors that your founding
and executive teams propagate, right?
And it’s accidental, right?
And often times there’s things that are not good behaviors,
they get propagated culturally.
And often times people justify it because they’re like,
well, they conflate the correlation with causation, right?
They’re like, because we, you know,
or have behaviors where maybe we’re like a low empathy
company, let’s say, but they don’t call it that.
They’re just like, we make decisions
based on like meritocracy, right?
And they’re like, but the best idea is gonna win,
but then maybe that’s like because that’s a behavior
that they’ve propagated,
but that might not be the real reason
why they’ve actually been winning, right?
I think a lot of companies in Silicon Valley
kind of succeed despite their management actually,
not because of it.
And what I mean by that is like the idea was so good
that a bunch of 25-year-olds could run the company, right?
That core product market was so good,
it was just a rocket ship
and then people were just trying to hang on.
Now, eventually I think they do figure it out,
but often times in those early days,
and I think it’s actually quite, you know,
not intentional and often times not that good.
– Yeah.
You know, in our conversation today,
we’ve talked about all the things that you’ve changed.
– Yeah. – Right?
You’ve changed, you know, from consumer to B to B,
you’ve changed, you know, how fast you fundraise,
you know, there’s been a lot of different changes.
You know, is there anything that you feel like you,
like there’s a core that you’re like,
okay, there’s this thread that I’m trying to do the same
between all the companies,
or is it just really like iterating very quickly
and, you know, you’re doing a lot that’s different?
– Well, I think that core ethos of, yeah,
iterating quickly, you know, that’s like a YC ethos,
that’s something that we really did,
carry on at the very beginning.
So speed was, you know, something that’s pretty important.
I think that really being helpful in the community,
not just your startup, I mean, including your startup,
but also the community of startups,
that’s something that we learn,
the behavior we learn from, you know, the early days of YC,
and even like our community of friends who were founders,
who all became successful, you know, helped each other out,
and then now today, you know, it’s an ethos
that would take the atrium to really build a company
that’s, you know, kind of for startups, you know,
by startups that helps out these, you know,
fast-growing startups.
So that ethos is probably something
that’s pretty similar, you know, kind of similar
to like what you guys have at Andreessen, right?
Which is like, if we can, you know, be the most helpful
in terms of providing these networks of services,
that is something that is going to, you know,
kind of pay dividends for us as a brand.
You know, that’s something I believed personally,
and then also at each room throughout my entire career.
– Right, right.
Yeah, I mean, as you know,
one of the things that’s great about the Bay Area
is that it ends up being this very long-running,
relationship-driven place where, you know,
you meet people like, I mean, we met like 10 plus years ago,
right, and that’s the kind of interesting thing
where there’s many, many cases where you can work together.
And so, you know, focusing on value creation,
as opposed to like, how am I going to try to position myself
to like capture the most value?
Like, I think that, you know, like that certainly runs,
like I think it’s one of the very special things
about the Bay Area. – Absolutely.
If I think about where we’re at, you know,
where all the people who I, you know, saw in the early days,
like 13 years ago, all these different founders,
you know, these two-person startups
that won’t even anything, where they’re at,
their company might not have succeeded,
but they have like created some value here in Silicon Valley
by being in that ecosystem, being helpful,
and then, you know, maybe becoming an executive
at someone else’s company,
or becoming an investor, early-stage investor
at another company that really worked.
And so, there really is like a feeling
of if you kind of get out what you put into this community,
and that’s one of the things I really love about it.
– How do you think about the idea that, you know,
when you’re first getting started,
you’re a first-time entrepreneur,
there’s kind of like low expectations, right?
‘Cause you’re like, maybe this’ll work,
maybe this won’t work,
people’s expectations of you are like kind of low too,
’cause they’re kind of like, I don’t know,
who knows, you know, Justin’s often in San Francisco
doing this thing, he’s running around with a camera
on his head, and it’s just kind of a fun thing.
And then, now, several companies later,
because, you know, also you’ve raised money,
and because you’ve done a lot, et cetera,
you know, the expectations must be higher.
Like, how do you think about, you know,
how do you think about those expectations
managing your own, you know,
your own expectations around that?
– Well, I always think that every entrepreneur’s expectations
for themselves are very exceedingly high, right?
If you’re the type of person who was a PM or engineer
at, you know, one of these fan companies,
and then you’re like, I’m gonna start a startup
’cause I see other people doing it,
then you don’t think, you don’t go into it thinking,
well, I’m just gonna create like a whatever,
something that’s like a nice small business, right?
You go in being like, I’m gonna raise series A
from Andreessen, and we’re gonna be, you know,
this product that just goes,
the next Snapchat or whatever.
And so I think that, like, it’s always a battle
against your own, like, the kind of devil
on your shoulders telling you, you’re not good enough,
you know, you’re not doing well enough,
you could be doing better.
And I think the way that you win that battle
is by really internalizing and realizing
that whatever happens, you’re gonna be fine.
And you’re probably gonna be the same,
you’re not gonna be happier or less happy, actually.
And now most people do not actually successfully
internalize that well enough, in my opinion.
But it is true, I firmly believe it’s true,
and it’s something that the sooner you start practicing
that in your head, really, you know,
feeling that and experiencing that in yourself internally,
then the happier you’ll be.
And that’s not to say that a lot of, you know,
people I come into contact with, like, friends even,
or people who work for me are like,
well, my drive, like, that need to win at all costs
is my edge.
But I really don’t believe, I mean,
maybe that’s true for other people,
but for me, I never found that to be the case.
It’s like, no, it was just like the kind of unhappiness
that was created around it that would make it
actually less sustainable for me to continue on,
because I was always, you know, you can’t,
human beings don’t wanna live in a high stress,
high anxiety, stay for too long.
That’s how you can burn out, right?
So startups are not, I mean, contrary to popular belief,
it’s not a sprint, it’s a marathon, right?
There’s these overnight successes,
Twitch came out of nowhere, eight years from
incorporating that company to selling it,
almost exactly eight years, right?
So that is a long time.
And in order to last a long time,
you need to figure out a way that you are okay
with what’s going on, and what’s going on
is always gonna involve bad things.
Like things, you know, there’s gonna be good
and there’s gonna be bad.
So if you don’t figure out a way
that you psychologically are okay with that,
you’re gonna give up, and if you give up,
you’re never gonna see it to the ultimate potential
that whatever your startup is can be.
– Great.
I’m gonna throw in kind of two last questions in here.
One is, you know, what are you reading these days?
Do you have any sort of recommendations, podcasts
that you like, kind of media consumption
is kind of a way to learn yourself?
– Yeah.
– And anything sort of especially super impactful
over the last couple years that you wanna reference?
– Yeah, that’s great.
So reading a lot, actually,
’cause I deleted all the entertainment apps off my phone,
including the browser, and I’d locked it
so that I don’t can install new apps
’cause I was a total phone addict.
That includes Twitch.
– Wait, how do you lock?
How do you lock your–
– So you can lock installing new apps,
you can delete the app store
and put a passcode lock on it.
– Oh.
– And I gave my wife the passcode,
or she put in a passcode, I don’t know what it is.
– Right.
– So I can’t–
– This is like a parental lock.
– It’s a parental lock, exactly.
So I don’t have control over my own phone anymore.
But the consequence of that is I read a lot more books,
which is good.
A couple of ones that have been particularly impactful to me.
Number one is this book called The Untethered Soul.
So this book changed my life.
It’s really about the idea is that you are not
the thing that you think you are.
Most people go through life thinking they are the experiences
that they’ve experienced, the thoughts that they have,
or the emotions that they have.
But really, you’re just the observer of these things
that are happening.
And by creating, it’s almost like you’re watching a movie,
right, like a movie that has all the five senses,
plus emotions, plus thoughts.
So like a seven dimensional movie of the just end life, right?
And I think that was a very important message to me
to realize, like an internalize that like actually
these attachment, these things that I think will happen
that will like drive happiness, like experiences or events
or whatever will never actually drive
true internal happiness.
So amazing book, The Untethered Soul, highly recommend it.
Another book that I think made me a much better leader,
I was this book I read called Leadership and Self Deception.
Amazing book.
The book, the premise of the book is really there’s two ways
to treat other people inside the box and outside the box,
but really I mean like without empathy or with empathy,
like treating them like an object or a person, right?
And the idea, the fundamental idea behind the book
is if you treat people like an object,
number one, they don’t like it, right?
But the second thing is, if you treat people like objects
who are just there to fulfill something for you, right?
Like at work, it would be like to, you know,
hit some number or metric or whatever, do some job.
The problem is that you will lie to yourself about
when there’s negative situations about what your role is,
you’ll self deceive, you’ll say,
oh, this person is 100% at fault
and I’m 0% at fault.
And I found myself actually doing that a lot of times.
I realized, you know, I felt like I was,
you know, had a high degree of empathy for other people,
but I realized that was for people who,
I felt like we’re performing really good
where my observation was like high performance.
But I wasn’t, where my observation,
where my feeling was that there wasn’t high performance,
I felt like I would slip into this like low empathy mode.
And the problem is that when you’re in that mode,
you don’t admit, what are the things that I have done?
What, you know, Justin, what are the things I have done
to contribute to that situation?
So examples could be put someone in the wrong job,
didn’t give them clear enough criteria for success or failure,
didn’t support them with the right resources, right?
There’s many reasons why I could have contributed
to some situation failing.
And I found that like I would lie to myself in those situations.
So, you know, that was a really important book for me.
And those are probably two ones I really recommend.
– That’s great.
Are you doing a lot of podcasts right now?
– Listening to them? – Yeah.
– Been listening to– – That kind of entertainment.
– Yeah, I listened to some podcasts.
I’ve been listening to some of the Joe Rogan experience.
– Nice. – And that’s probably the,
this is probably it.
I like, I just listened to one with Alex Honol,
where he’s talking about climbing, you know,
so it’s pretty interesting.
– I’m gonna ask you the time travel question.
So if you were today, an enlightened, repeat entrepreneur,
to go back to yourself when, you know,
you’re 22, 23, just getting started doing this thing.
You know, what advice would you give yourself?
– When I’m just getting started, you know,
probably join Facebook.
No, but the, maybe the real answer,
I’ve actually, you know, I don’t really regret
any of the, like, economic choices or anything.
I think I’ve had this tremendous opportunity
to, like, build and discover these new things
and build companies and I wouldn’t trade it for anything.
I think the thing I could have done better
or, like, learned, you know, back then is,
you know, self-improvement is a thing.
You should probably, like, work on that.
Maybe that’s number one.
The second thing would be–
– Stop eating pizza at work.
– Yeah, stop eating pizza at work.
Number three would be,
you should, you know, things take time.
Like, don’t be in such a, you know,
it’s not, like, a one-year, one-and-done,
like, no, you’re a billionaire, you know?
Like, if you look at the, let’s say,
any sort of, like, the Amazon share price
or, like, market cap over time, right?
It looks, like, even through, like,
the last couple years looks like an exponential curve, right?
And so, you know, if Bezos had been, like, your,
you know, like, 15,
which is a long time to be starting a company,
like, oh, man, I made it, I’m done,
like, I’m gonna retire, like,
well, you know, the company would look a lot different,
right, so, you know, things take time
and I have to constantly remind myself that.
I think humans, you know, here in Silicon Valley,
especially, but then human beings in general,
are wired to, like, always want the new,
you know, look for the new thing.
What’s new?
What are you, like, what’s your new thing?
Something that everybody’s asking about in Silicon Valley?
They’re always, you know, that’s a question here.
But the best entrepreneurs here,
the ones who have created lasting companies
and lasting value, they stick with their thing
for decades, you know?
And that’s what impresses me most now
and I wish that I had kind of realized that, you know,
before.
– Awesome.
– Better late than never.
(laughing)
– Awesome.
Justin, thank you for coming by.
– Yeah.
– Thanks for having me. – Really good discussion.
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– Hey, I’m Andrew Chen from Injuries and Horowitz
and today we have Justin Kahn, who is one
of our repeat entrepreneurs that we are very excited
to be working with on Atrium.
And so we’re gonna talk a bunch about
what is it like to be a repeat entrepreneur?
I think we were just going through the list.
There’s like five different companies on there
and you’ve learned a ton from every single one.
And so we’re gonna do a series of sort of compare
and contrast across quite a number of topics.
But as a very first step,
I think it’d be awesome to have Justin talk about
some of the companies that you’ve been involved in.
And I know the company you were running when we first met
where you were running around with a camera on your head
is not actually even your first one.
There’s one before that called Kiko.
So why don’t you talk about Kiko first?
– Sure, yeah.
So I’ve been an internet entrepreneur here
for the last 14 years since 2005.
Our very first company was called Kiko.
It was kind of like Google Calendar,
but it came out one month before Google Calendar came out
and wasn’t really that good when I’m honest about it.
And so that company didn’t work out super good.
We ended up fire selling it on eBay
after several failed acquisition attempts
with the Sullivan Valley players.
And then after we did that, we started another company.
This one was even less well thought out than Kiko was actually,
which was the idea was we would create our own
live video reality TV show on the internet.
I do think that tapped into several things
that were in the zeitgeist
that actually have become popular now.
But unfortunately, we as talent in our own show
were not very entertaining and not very popular.
And so we launched this live streaming show.
We called it Justin TV.
‘Cause I was the only one in our four founders
who was stupid enough to put the camera on his head
and be like, I’ll make myself the subject of this show.
And you literally wore, I remember you wore a backpack.
– Yeah, so this was 2007.
So it was pre-iPhone, pre-good cellular internet.
So we had this computer in a backpack
with like multiple cell phone modem connections.
And we hooked it up to a camera.
So there was a camera, this computer virtualized the video
as a webcam, basically sent it over to the server.
And then we had this very hacky way of streaming it out
to the millions of people watching,
actually not millions, hundreds,
but the people who were watching at home,
they were following along, it was actually pretty fun.
They could text, we put our number up there,
they would text me, usually fairly offensive things actually.
But then eventually we launched this show,
people started coming because they were like,
what is this guy doing, this is crazy.
They were like, you’re very boring, I hate your show,
but I want to create my own live video stream.
So how are you doing it?
And then the light bulb kind of went off
and we said, aha, let’s create a live video platform.
And that became Justin TV, the platform.
And then after that, we ran that for a couple of years,
I’ve condensed it because it’s a very long story,
but we raised a bunch of money,
ran it for a couple of years,
hit the nuclear winter of video startups
where all the other video startups in Silicon Valley died.
We were pretty scrappy and survived on like a ramen budget.
Eventually decided we needed to pivot to some new ideas.
And from there we incubate a few ideas internally.
One of them was a video app called social cam,
which we spun off and eventually sold to Autodesk.
And another one was a site that we,
my co-founder really thought of,
which was the idea was focus on,
let’s focus on the video game related video on our site.
And that became Twitch, which kind of grew and grew and grew.
We eventually pivoted the entire company to Twitch.
My co-founder Emmett was the CEO of the company
and eventually sold it to Amazon for $970 million in 2014.
About five years ago.
Along the way started some other companies
to start this company called exec,
which is in the errand running/home cleaning space.
It’s kind of like a handy year home joy.
We actually ended up selling it to handy,
which through an act of God sold to Angie’s List this year.
And then more recently,
I’d been a partner Y Combinator for a couple of years
and then incubated a few companies.
One of those was this video Q&A app called Whale.
And then just fast forwarding all the way
up till the present day,
decided I want to really put all my eggs back in one basket,
precariously thrown around basket.
And so I decided I’d start a new company.
That idea was Atrium,
which is a technology enabled law firm for startups,
really trying to solve all the problems that I had
as an entrepreneur when dealing with legal.
To make legal faster, more price predictable,
more transparent for me, the business owner,
you know, the business manager.
And that’s what we set out to do about two years ago.
It’s going pretty well.
We’re serving a bunch of startups here in Silicon Valley
with all of their needs.
And it’s been great, but I’m sure we’ll get to that.
– Awesome, yeah.
Well, I think one place where I’m going to start on this
is a lot of the advantages of being a repeat entrepreneur
are that, you know, you can raise more money
and there’s more, you know, maybe easier to recruit talent.
And there’s, you know, there’s all these advantages
that kind of, you know, come along with that.
One of the disadvantages I find ends up being that,
you know, there’s so many like distractions, right?
Like you could, there’s a million different things
you could do.
There’s a lot of things pulling at your attention.
I’m really fascinated by, you know, your movement
from going from YC and an incubator
where you can maybe kind of dip into a lot of little things
versus kind of putting all your eggs in one basket
and trying to like start a company.
Like, you know, to talk to us about that,
that kind of decision.
– Yeah, that’s a great question.
So once you become, you know, successful in some way
in Silicon Valley, whether that’s, you know,
you’ve been the executive at a company
that’s, you know, rocket ship unicorn
or you’ve started a company, you know,
the world opens up, right?
People want you to be a VC.
They want you to, you know, work on projects with them.
You can start any company that you want,
which is great, right?
But there’s just paradox of choice
and focus can be a huge problem.
I know for a lot of friends of mine, it has been as well.
As an investor, as a partner at YCom,
there were some parts I really liked.
You know, I loved helping early stage founders out
and like really working with them on these problems that,
like I felt like for five to 10% of them,
it was like life changing, right?
Like me helping them out in a way,
I came up with some great idea
or helped them at a critical moment.
That was life changing.
But then there was a large majority of them
that probably could have been listening
to a YouTube video of me or this podcast
and like you get the same information, right?
And so I didn’t feel like the feedback cycle
was fast enough also as an investor.
And I didn’t really feel ultimately,
like after the first couple of years
that I was continuing to learn and grow.
And you know, I’m still in my 30s.
I was like, I need to do something
where I’m going to be forced to grow.
And really the number one vehicle for personal growth
that I’ve ever experienced in my life has been startups.
You know, so I went back to when I knew
and I really decided that in order to grow as a founder,
you know, we had a pretty big outcome with Twitch
and I’d seen a lot of different things
in order to really grow to the next level.
I would have to do something that potentially
could be even bigger.
And so I really felt like it deserved,
that deserved my full attention.
And so that’s kind of how I decided.
I don’t necessarily think it’s the right answer
for everyone because what I didn’t mention
was that I had selective memory at the time
and I forgot just how painful starting a startup could be.
And so for the first couple months of atrium,
I was like, oh man, this is a dream.
I’ve like finally leveled up.
I learned all these skills.
I’ve like, I made it as a founder.
And then reality boom set in.
And of course there were nothing ever goes according to plan.
There were pains, there were struggles.
And that was, you know, that’s part of the journey.
But then the good part is, of course,
when you experience pain, that is a catalyst for learning.
And so I really got what I wanted in the end,
which was forced to learn.
– Right, that’s great.
And I know one of the big differences
among some of the companies that you started
in the past versus atrium,
and something that you’ve talked a lot about is,
you had this sort of succession
of very like consumer oriented startup,
sort of like watching other people play video games.
Like that’s as consumers, basically.
And so very interestingly, atrium is a B2B thing.
And why did you choose B2B?
Was it just for novelty?
Was it just to push yourself?
Or do you think that there’s something different in mind
that maybe takes advantage of some of your new found skills?
– Yeah, well, Twitch, I guess, is really the,
it’s like the ultimate consumption thing,
’cause it’s you’re consuming someone,
consuming video games.
– Right, right.
– For me, I felt like maybe this was an analysis
I’ve done like retroactively,
but I think I’ve had this discussion
with a couple people with multiple time founders.
And when you’re an early stage founder,
when we started Kiko and then Twitch,
when we started Twitch, we were like,
or just in TV, it was like we were 23 years old.
And we had no skills.
I never had a real full time job in my life.
And even though we were programmers,
we were like new college grad programmers.
We were not good.
We were horrible managers.
We basically had nothing going for us.
When you have nothing going for you,
except for your like willing to put in hard amount,
like long hours on a lot of blood, sweat, and tears,
then you should focus on things that are like,
where there’s a lot of market risk,
because ideas where there’s market risk,
you can potentially win those, right?
Now, as someone who has abilities and skills,
where I’ve learned skills over the last 14 years,
you wanna focus much more on like execution risk things.
And so I felt like B2B startups
are more about execution risk.
I felt like this legal market,
particularly was already a big market,
and you just have to figure out
how to do it 10 times better, right?
And I felt like I had a roadmap
for how to do that in my head.
And so that’s why I felt that this was a better use of time.
‘Cause some of the consumer startups that I had incubated
and played around with post Twitch,
actually it was really hard to find product market fit, right?
Like, I don’t have any advantage
in finding product market fit with a consumer app
more than the 22 year old Justin.
– You might have a disadvantage.
– Yeah, I probably have a disadvantage
’cause I’m like already more set in my ways.
I’m like less in tune with the culture.
I’m like, I don’t know what the kids are doing.
So, with the Justin of today, invent the Twitch of today.
Like, I don’t think so, right?
Like I’m an old guy now, man.
(laughing)
It’s game over for me.
– I wanna unpack this market risk, execution risk.
‘Cause that’s obviously,
it’s such an important distinction,
but very colloquial, kind of in our understanding of it.
What do you mean by market risk
and sort of maybe new entrepreneurs
can have an advantage in market
and tackling something with new market?
How do you know if an idea has a lot of market risk?
– Sure, that’s great.
So, Twitch and H&M are the perfect examples, right, almost.
So, Twitch, it’s like when we started,
when we pivoted Justin DV to Twitch,
or even Justin DV is a good example,
but Twitch is the best one probably.
When we pivoted Justin DV to Twitch,
nobody believed that there would, this was a market, right?
No one believed, no investors,
very few of our even internal employees believed,
and even the founders were skeptical.
Emmett deserves the credit here, ’cause he had belief,
but a lot of the other co-founders were skeptical.
I’m like, does this exist as a business?
And so, the good part is that the competition there
was very low, right?
There weren’t experienced entrepreneurs being like,
this is gonna be a huge business, we should compete.
So, really it was, the entire thing was market risk
and figuring out, do we have product market fit,
how do we build product market fit?
– ‘Cause in that case,
you’re trying to be the first in the category.
There’s no substitutes really.
You’re watching someone else play street fighter
at the arcade, that’s a substitute.
– Exactly, you have a lottery ticket, right?
– You have a lottery, yeah.
– It’s a lottery ticket, and if you pivot a bunch of times
and listen to your customers,
you might be buying more and more lottery tickets.
But your lottery tickets are just as valuable
as the experienced entrepreneur’s lottery tickets
that he’s buying.
So, he’s a fool to play that game,
and I don’t think you see as many experienced entrepreneurs
playing that same game.
Whereas, with execution risk businesses,
my lottery ticket now is way bigger than the guy
who’s like the 22-year-old Justin, right?
So, for a B2B startup, I know, oh, I can attract talent.
I can hire a sales team.
I can raise capital.
And so, it’s a lot more, for something
where it’s very established that that’s gonna be a business,
or some business is gonna be in there,
it’s like he’s stupid to play against me, you know?
– Right, that makes sense.
Well, you know, and I always find it funny
that in the consumer startup world,
that if you look at the last kind of decade of hits,
if you were to tell people, oh, yeah,
the biggest hits are gonna be this app
that lets you get in strangers’ cars,
this app that lets you stay at someone
you don’t know’s like house,
an app where you swipe left and right
in order to meet people on the internet,
and an app that lets you watch other people play video games.
You would be like, that’s the craziest list of
billion-dollar companies I’ve ever heard.
And yet, that that is actually how consumer
the internet actually, you know,
the ecosystem unfolds, it’s insane.
– It takes a lot of people who have nothing to lose
to discover those ideas, right?
– Right, yeah, and so one of the things,
one of the clear advantages in all of this
is that, you know, let’s talk about fundraising,
and the decision on whether or not to raise
a bunch of money out of the gate,
versus doing the kind of, you know,
ramen profitable, you know, cockroach thing, right?
That’s sort of like, you know, one common contrast,
and then obviously you had a very unique
fundraising strategy as well.
So maybe talk about that decision,
and then kind of how you ended up pursuing it.
– Look, I’m not convinced that raising a ton of money
out of the gate is the right strategy.
You know, the Silicon Valley is littered
with dead bodies of these companies,
you know, the Juceros, and the Kools,
and like all these companies that have raised
a ton of money, and then like they,
when you have a ton of money, you spend a ton of money, right?
Now there’s other companies like the Jet.coms
that, you know, they made it work.
So, you know, I’m not convinced it’s the worst strategy ever,
but I’m not convinced it’s the best.
But for me personally, you know,
where it’s an execution risk business,
I’m too rich to like, fuck around with the like,
you know, okay, I’m just gonna do a seed round,
and like, and just like, take a long time, right?
Like for me, speed to market and execution
was really important, and I felt also like
this market really supported and required it,
because, you know, it is the legal space,
there is, you know, so a lot of value
in making sure that the clients and the talent,
the attorneys talent, and other legal providers,
like, think this company’s gonna be around, right?
So that’s very important.
And so, you know, this is a strategy,
I don’t necessarily recommend to anyone
who can raise a ton of money that this is the right strategy,
it’s just the strategy that we picked.
In terms of the tactics of like how we did our round,
especially our Series A, you know, my idea was,
because VCs are kind of naturally adjacent to legal,
right, like, for example, when you fund a company,
they need someone to help them on the legal side
with all of the, you know, paperwork
and the execution of that funding round.
We felt like getting a lot of VCs on our side
would be a good tactic, and so we ended up going out
and raising money for our seed round of, you know,
over 90 different investors from all over Silicon Valley
because I felt like it would be really good
to have those investors on our side
and recommending Atrium as a channel partner,
and so that was our tactic there.
– Right, and I think it’s something where,
you know, to your point, if something
that you’re working on is primarily execution,
then that means that, you know, you can,
there are times and places where you can use money
to solve it versus, it seems like, you know,
part of the market risk thing is it just, you know,
to your point, it sort of lets you buy more lottery tickets,
but it may not accelerate the process
of actually doing it, right, and so I think that,
that sort of feels like one main difference,
and then the other one is, you know,
that just to build on what you’re saying is that
if you are in an industry where trustworthiness
is really important, then being well-capitalized is key,
you know, the same way you wouldn’t, you know,
if you’re gonna, you know, for example,
you know, build a FinTech startup where, you know,
you’re gonna ask consumers to trust their money
with you, you know, like you wanna be legit,
you wanna be well-capitalized, you wanna have, like,
you know, super strong executives
and board members and investors, and like,
and that’s a strategy, kind of, that’s a little bit,
kind of, like, self-perpetuating as well.
– Yeah, that’s a great example.
If you’re gonna build, like, a new bank, right,
like an online, or like a mobile-first bank,
which is, I think, some people are doing,
would you wanna raise, you know, $1 million,
or $1 million seed round, or a $5 million seed round,
or a $50 million series A out the gate?
Obviously, if it’s available to you,
you want more money, ’cause you know people need banks, right?
It’s just a matter of can you do it better, right?
That’s a perfect example, and there’s, you know,
there’s many others here in Silicon Valley.
I think we’ve actually shifted more
as the cycle has changed over the last 10 years,
the tech cycle.
We’ve shifted more to these execution-risk startups,
and so, you know, you’ve consequently seen,
I mean, it’s a chicken and egg thing, really,
what came first, but like, you’ve seen these more and more,
like, bigger rounds, I’d say,
that are supporting these companies.
– Well, you know, one of my,
one of the partners here, Chris Dixon,
has talked about the idea that, you know,
if you have a set of problems that has not been able
to get solved and improved in, you know,
the 20 years of the modern internet,
then maybe all the techniques that we pioneered
in the last, you know, decade plus,
like being asset-light and just throwing software,
and just shipping really quickly, and being really lean,
like, maybe those techniques don’t work for a reason
in healthcare and fintech and legal services
in real estate, and like, you know,
some set of those things, right?
And so then, very quickly, you have to think,
okay, well, you know, if those techniques don’t work,
otherwise, it would have,
someone would have tried it already,
it would have, it would have sort of, you know,
a little bit like efficient market hypothesis.
– Yeah, that’s the thing.
– It would have kind of like happened already,
like, maybe you need a foundationally different approach.
And so, I think that is actually one of the reasons why
there’s more of these like, quote unquote,
full-stack startups that are going after
these really, really difficult areas.
‘Cause like, you know, otherwise,
you wouldn’t be able to do it.
– Yeah, well, running experiment right now.
– Yes, yeah, right, no, I think that’s right,
I think that’s right.
So, you know, one of the fun topics,
one thing that I have a tremendous amount of respect
for you on is you’re very, you know,
you’re always on the leading edge,
thinking about, you know, self-improvement,
how to sort of, you know, your own, you know,
personal performance at work, you know, at home, et cetera.
And obviously, one of the big things about, you know,
running a company is that it is enormously stressful.
Right? – Yeah.
– And so, talk to us about like, you know,
when you were a first-time entrepreneur,
kind of Kiko, Justin TV, you know,
how did you think about, you know,
managing the stress of, you know, running a company?
And what was your approach there?
And then let’s talk about kind of like,
the new and improved Justin now, you know,
kind of 10 years later.
– Yeah, so in the early days, you know,
10 years ago, I was not doing anything
in terms of like improving myself.
In fact, I think I used to think about people’s attributes,
maybe not your skills so much in terms of like, you know,
it’s your skills at programming or stuff like that,
but more of like your attributes.
Like, I don’t know if you ever played Dungeons and Dragons,
but when you create a character in Dungeons and Dragons,
you roll this like 20-sided die and, you know,
your strength, it’s like 14, your intelligence,
you roll it and it’s six or whatever,
and that’s what you have, you can’t change it.
And so I felt like people’s attributes
were kind of like that.
And so I never worked on that very much,
self-improvement stuff outside of, you know,
like yeah, I became a better programmer
’cause we were programmed, you know,
but I didn’t work on things to like make myself,
I don’t know, smarter, right, or harder working,
or like awake more hours of the day, right,
like alert more hours a day or anything like that.
So it was very happened, you know,
everything was kind of accidental.
Like we would, you know, I was not dealing with stress
well at all.
If there was a problem in the company,
I would be very emotionally avoided to it,
or I would like drown my sorrows in like alcohol, right,
which is not a very good coping mechanism at all.
And so, and then like, you know,
in terms of even just down to like
what we were like eating at lunch,
I was, you know, we were talking about this this earlier,
but I would, we would have like pizza every day
at lunch at Justin TV, and then I’d like fall asleep.
Like I’d go into like a carb comb,
like a carb comb in the afternoon, like every day.
And so now more recently, like with atrium,
it’s been a tremendous vehicle
for my own personal discovery,
because I experienced the stress again.
You know, I was like, oh my God, it’s stressful.
Again, this is crazy, why is it so stressful?
And so I started looking for ways to deal with that,
and I really, I mean,
if I had a number of things that started working for me
after I started really exploring it,
a number of things that started working for me
starting last year, you know, everything from,
friend of mine recommended a daily gratitude journal.
So I’ve just been doing that every day,
writing this gratitude journal, five minute journal.
You write down the three things every morning
that you’re grateful for.
And that seems like a very simple thing
and kind of hokey, actually, when I first heard about it.
But what I realized was it helps recontextualize
all the ups and downs that you experience
as an entrepreneur, especially, I mean,
the downs really, like throughout the day,
they’re not as big of a deal,
because in the morning, you’re writing down,
like, wow, I have this opportunity.
You know, I remember the day we came in and pitched,
you guys here, I wrote my gratitude journal,
I get to pitch, you know, Andrewson Horowitz.
That’s amazing, right?
Even whatever happens, that’s an incredible opportunity.
It puts me in the top 0.01% of people in the world
without opportunity, you know?
So that was like pretty amazing.
And then, you know, every day there’s something,
like if you really think about it,
there’s so many amazing things that happen to you
as a human being here in Silicon Valley.
Even just like actually one thing I think in the morning,
oftentimes it’s like the supply chain,
the global supply chain to deliver coffee
from like around the world,
so that I can grind up fresh coffee
and like a pour over in my Chem-X in the morning.
– Right.
– That’s amazing.
– It is amazing. – Like if you think about it.
– It’s totally amazing. – Yeah.
– Right.
– So the gratitude journal really working for me.
And then another thing–
– You’re still eating pizza for lunch every day?
– Yeah, so diet, another thing, I stopped eating pizza.
– So, entirely?
– No, well I started eating a ketogenic diet,
which is a high-fat diet,
but really the reason for me is like,
I just don’t get as tired in the day anymore.
And so that’s been really helpful.
And last year I was experimenting,
I did like some one meal a day, days,
you know, like four days a week.
Some of these weird like Jack Dorsey diets,
kind of Jack Dorsey light or whatever,
but it’s been good for me.
You know, you had to do what your body feels like,
it feels good.
So, you know, that’s some diet and exercise,
pretty religious about exercising,
you know, try to do something every day during the work days.
– Yeah.
– And then the last thing that was really big
is meditation for me.
Start off just with headspace, you know,
I’m not the type of person that people, you know,
assume would be a heavy meditator
or very introspective or anything like that.
But for me, just like starting off with headspace last year,
and then now I’ve been doing transcendental meditation,
which is kind of what Ray Dahlio talks about
and the principles, that’s worked really well for me
to just be more present during the day in my life.
It’s pretty amazing, amazingly profound effect.
– I feel like your Twitter stream
is part of your gratitude journal.
– Yeah.
– ‘Cause I read your Twitter stream and I’m like,
oh, this is like very philosophical.
You know, it’s not like just pulling out like,
oh, here’s a blurb from the latest S1 or something.
Like you’re like, you know, you’re like sharing ways
that the startup community can, you know,
to think about themselves.
– Yeah, the way I think about it is like,
if you want something to be part of your identity,
talk about it.
If you want to learn something, teach it.
You know, and I really believe that.
So for me putting out, you know,
what I’ve been doing on the mindfulness side
and for myself to be more emotionally kind of stable
throughout the days and weeks and months,
as a startup founder, that’s been really valuable to me.
So if I can spread that to other people,
it’s gonna help reinforce it as an identity for me,
but it’s also gonna hopefully help those people as well.
– Right.
You know, one thing I’ve been working on a lot as well,
the last thing I’ll say is just working on realizing
that your attachment out in the very early days
of Justin TV and Twit, Kiko and all these companies,
I had a huge ego attachment to the outcome of the company.
– Yeah.
– Right, my identity and the companies
were like very intertwined.
And more recently, I realized that was the same
at Atrium actually.
Like again, I was like creating that same pattern,
but it was like, it’s a very unhealthy pattern.
So what I realized was I needed to start telling,
reminding myself that no matter what happens
with this company, I’m not gonna be any happier
or any less happy in the long run.
There might be a short burst of unhappiness
if it fails or happiness if it succeeds amazingly,
but you’re not gonna get any happier.
Really, if you’re relying on outside things,
external factors to drive your inner happiness,
you will always be disappointed in the long run.
And the funny thing is I’ve actually run the experiment,
not an A/B test, but a linear experiment on that,
because we’ve had more and more success over time.
Like we started off really paying ourselves,
I think with Kiko, $7,800 a month,
but we only paid ourselves every other month.
And so then we raised funding for Justin D.V.
and we were able to make a little salary,
then we became profitable, we made a lot more,
and then we sold one company, then we sold a lot of companies.
And so we kind of ramped over time.
And after the basics of Maslow’s hierarchy of needs,
we’re taking care of, I felt like I could go out to eat.
I don’t know if that’s on one of those Maslow’s
hierarchy of needs, but after that basic thing,
I could afford to go out to eat.
None of it never mattered.
It never made me sustainably more happy.
And so just reminding yourself of that
and trying to remove those attachments in your mind,
it’s easier said than done,
but having that as like an active practice
has been really important to me.
– Let’s talk about mentorship as part of that, right?
So when you’re building Kiko, Justin D.V.
and you’re a first time entrepreneur,
there’s a lot of experienced people
who are kind of like, go ahead of you in the thing.
And so that’s fantastic ’cause you can learn a ton.
Would love to hear kind of who you thought of
as your kind of lifelong mentors,
people that have helped you for a long time.
And then the other problem that’s super interesting is,
then you start atrium and you’ve had
some major successes behind you.
And then in some ways, the number of people
you can learn from is a much smaller pool
and sort of like, how do you kind of curate your mentorship?
Maybe how has it changed over time?
That’s a broad topic, but would love to hear your opinion.
– Sure, absolutely.
So like the best part about Silicon Valley, in my opinion,
is that there are people here who have done it before
who are willing to help you.
That we would never have made it here even day one
without people who helped us when it was like economically
bad, waste of time.
We weren’t like, didn’t look like a hot prospect
company or anything, right?
So those people will, Paul Graham, great example,
founder of Y Combinator, Paul Buhay,
who is like a partner in Y Combinator,
but they invented Gmail inside of Google.
These are people who invested in us very early on,
mentored us very early on and helped us out.
And that was pretty amazing.
And really that ethos perpetuates itself,
because then as a partner in Y Combinator,
even today as an entrepreneur,
where there’s like lots of conflicting,
competing interests for my time,
I always make sure to spend a little bit of time
mentoring other startups,
because it’s kind of like a pay it forward thing.
And you do the thing that people did for you
when you were younger.
– One of the really obvious sources of mentorship
is actually peer mentorship, right?
And some of the folks that kind of came up with you
at the same time and ended up running
really interesting companies on their own.
And I know they all live in DeBose with you
in San Francisco.
Talk to us about some of your friends
that you consider your mentors.
– Yeah, so it’s great to have friends
who are kind of doing the same path in a lot of ways,
but are one or two steps ahead of you.
So it’s still a case.
Obviously Emmett, my co-founder who’s still running Twitch,
it’s over a thousand people.
I think it’s like 1500 people or something like that.
My brother, who’s COO of Cruise,
co-founder of Cruise, the self-driving car company.
And they’re like over a thousand people.
And Steve, the founder of Reddit,
they’re like 400 something people or whatever.
So, you know, seeing what their problems are,
you know, obviously the problems are always the same,
actually the problems are always like,
I don’t have the right alignment among my team
and I don’t have the right executive team.
It’s usually some variation of those things.
But, you know, hearing it from the horse’s mouth
is super helpful in terms of making decisions for me.
And then, you know, even outside of DeBose,
sometimes I venture into Soma
and having some of those, you know,
kind of early YC founders who have really made it,
you know, like the Drew from Dropbox, for example,
and just knowing like how do they think about
every, all those things, executive hiring, et cetera,
it’s been really helpful, helpful to me.
So, luckily here at Silicon Valley,
I have a lot of great resources.
And the last thing I’ll shout out is,
I have this new executive coach, Matt Mocharri,
who’s like amazing.
This guy is the guru.
He’s, you know, mentors a lot of different fast-growing
startups around here.
I just talked to him for like a 360 thing.
– Yes. – Yeah, yes.
– This guy. – Yeah, that was great.
– Incredible, highly recommend, can’t speak,
he’s like changing my life.
So, I feel like he’s an angel sent down from Heaven
to teach me, finally, after 14 years,
how to like manage a system.
And I’ve learned a lot from him, so.
– That’s great.
– Those are kind of three sets, you know,
executive coach, the peer mentors,
and then kind of those early stage mentors
that I had back in the day.
– That’s great.
And I know one of the topics that you must end up
talking about often is that when you’re building something
that has a little bit more just execution risk,
you know, you’ve raised some real money
to kind of get started.
A lot of it ends up being sort of like organizational,
complexity, company culture.
I know this is the big, big, big, big area focus for you.
And that’s something that is very different
when you’re trying to build something for the long run
versus when you’re kind of just trying to find
product market fit, and it’s kind of like 10 people,
and you’re just like, is this even going to make it?
Like, let’s not even work on this.
– Yeah.
– So talk to us about kind of how your approach has changed
on building the company and your leadership style.
– That is a great question because it’s something
I think a lot about.
So I had never thought before a couple of months ago,
and this may sound stupid in a way,
but I’d never thought, what is the kind of company
that I want to show up to work at?
So 14 years later, finally thinking about it.
But the real answer is like, when you’re a 22 year old,
just starting your company, or you’re in Silicon Valley
and you’re thinking funding rounds and exits,
you’re always thinking, what’s the next milestone?
Like, how do I just claw my way desperately?
However, whatever it takes, how do I get to that
next milestone?
It’s do or die.
And for some, you know, oftentimes it is do or die.
You don’t have the luxury, oftentimes, of thinking
about what kind of, or you feel like you don’t have
the luxury of thinking about what kind of company
you want to build culturally.
And so, I started at Atrium actually very much
in the same way, but like, what are the metrics milestones
we want to hit?
What’s the next metrics milestone?
What do we need to get to for a Series B
or a next round of funding?
And so, the problem with that was that a year in,
I realized, oh, shoot, I need to like,
there are like a lot of things that I’ve neglected
that are actually affecting our ability to execute.
And the number one thing there was,
what’s the culture going to be?
People didn’t know, like, what’s the alignment aspect
of like, what are we building?
What kind of company are we?
Who are we?
What are we building?
And then, what’s the culture?
How are we being intentional about it?
So, we did a lot to work on that,
ran through a collaborative values process over a year ago
where we brought the whole company together,
figure out what we care about.
And then more recently, I’ve been thinking about,
after a lot of this self-work in terms of making myself
feel kind of consistently good every day
and move my attachments to the outcome,
I’ve realized there’s a set of principles
that I want to implement at the company.
And that I think that execution will flow
from those things, right?
If we build a company that has a high empathy
for each other, where we have care for each other,
where people are very collaborative,
where people feel like the locus of control
for what’s happening is inside of them,
instead of outside of them.
Things are happening through them, not to them.
I think that all the execution will actually flow from that.
One of the things I never understood before,
which I feel like I really understand now,
is that saying that culture eats strategy, right?
I felt like I had very good strategy with Atrium,
but I forgot about culture in that first part of the company,
and now I realized how important it is.
So one of the things I’ll say that we’re doing
is recently I read this book called
“The 15 Commitments of Conscious Leadership,”
which is an amazing book,
but it’s really about building a certain type of company,
what the authors call a conscious company.
But I would centered around that locus of control question.
Do you have radical responsibility
for what’s going on in your life, in your company,
regardless of who you are?
And read that book, and I realized this is the type
of company that I want to work at.
It’s a company populated by team members
who really believe in these principles.
And so we’re kind of going through a process
of trying to implement that at our company.
And really culture is one of the highest.
It went from something that I didn’t prioritize
to my top priority.
– Yeah, well, and I think it’s really interesting
because you’d started Kiko out of school, right?
And so unlike some folks who maybe,
they go and they work at Google or Facebook or something,
and they maybe have a template
for the company culture they want to create,
this is something that you kind of had to learn
and adjust over many, many kind of company iterations
of various companies that you built.
– That’s right, we had never worked at a place
with good culture or a culture, right?
Because we had always worked at our own company,
so we were just making it up as we went along.
When you’re not intentional about your culture
or type of company you want to be,
then the culture ends up being the accidental collection
of good and bad choices and personality quirks
and good and bad behaviors that your founding
and executive teams propagate, right?
And it’s accidental, right?
And often times there’s things that are not good behaviors,
they get propagated culturally.
And often times people justify it because they’re like,
well, they conflate the correlation with causation, right?
They’re like, because we, you know,
or have behaviors where maybe we’re like a low empathy
company, let’s say, but they don’t call it that.
They’re just like, we make decisions
based on like meritocracy, right?
And they’re like, but the best idea is gonna win,
but then maybe that’s like because that’s a behavior
that they’ve propagated,
but that might not be the real reason
why they’ve actually been winning, right?
I think a lot of companies in Silicon Valley
kind of succeed despite their management actually,
not because of it.
And what I mean by that is like the idea was so good
that a bunch of 25-year-olds could run the company, right?
That core product market was so good,
it was just a rocket ship
and then people were just trying to hang on.
Now, eventually I think they do figure it out,
but often times in those early days,
and I think it’s actually quite, you know,
not intentional and often times not that good.
– Yeah.
You know, in our conversation today,
we’ve talked about all the things that you’ve changed.
– Yeah. – Right?
You’ve changed, you know, from consumer to B to B,
you’ve changed, you know, how fast you fundraise,
you know, there’s been a lot of different changes.
You know, is there anything that you feel like you,
like there’s a core that you’re like,
okay, there’s this thread that I’m trying to do the same
between all the companies,
or is it just really like iterating very quickly
and, you know, you’re doing a lot that’s different?
– Well, I think that core ethos of, yeah,
iterating quickly, you know, that’s like a YC ethos,
that’s something that we really did,
carry on at the very beginning.
So speed was, you know, something that’s pretty important.
I think that really being helpful in the community,
not just your startup, I mean, including your startup,
but also the community of startups,
that’s something that we learn,
the behavior we learn from, you know, the early days of YC,
and even like our community of friends who were founders,
who all became successful, you know, helped each other out,
and then now today, you know, it’s an ethos
that would take the atrium to really build a company
that’s, you know, kind of for startups, you know,
by startups that helps out these, you know,
fast-growing startups.
So that ethos is probably something
that’s pretty similar, you know, kind of similar
to like what you guys have at Andreessen, right?
Which is like, if we can, you know, be the most helpful
in terms of providing these networks of services,
that is something that is going to, you know,
kind of pay dividends for us as a brand.
You know, that’s something I believed personally,
and then also at each room throughout my entire career.
– Right, right.
Yeah, I mean, as you know,
one of the things that’s great about the Bay Area
is that it ends up being this very long-running,
relationship-driven place where, you know,
you meet people like, I mean, we met like 10 plus years ago,
right, and that’s the kind of interesting thing
where there’s many, many cases where you can work together.
And so, you know, focusing on value creation,
as opposed to like, how am I going to try to position myself
to like capture the most value?
Like, I think that, you know, like that certainly runs,
like I think it’s one of the very special things
about the Bay Area. – Absolutely.
If I think about where we’re at, you know,
where all the people who I, you know, saw in the early days,
like 13 years ago, all these different founders,
you know, these two-person startups
that won’t even anything, where they’re at,
their company might not have succeeded,
but they have like created some value here in Silicon Valley
by being in that ecosystem, being helpful,
and then, you know, maybe becoming an executive
at someone else’s company,
or becoming an investor, early-stage investor
at another company that really worked.
And so, there really is like a feeling
of if you kind of get out what you put into this community,
and that’s one of the things I really love about it.
– How do you think about the idea that, you know,
when you’re first getting started,
you’re a first-time entrepreneur,
there’s kind of like low expectations, right?
‘Cause you’re like, maybe this’ll work,
maybe this won’t work,
people’s expectations of you are like kind of low too,
’cause they’re kind of like, I don’t know,
who knows, you know, Justin’s often in San Francisco
doing this thing, he’s running around with a camera
on his head, and it’s just kind of a fun thing.
And then, now, several companies later,
because, you know, also you’ve raised money,
and because you’ve done a lot, et cetera,
you know, the expectations must be higher.
Like, how do you think about, you know,
how do you think about those expectations
managing your own, you know,
your own expectations around that?
– Well, I always think that every entrepreneur’s expectations
for themselves are very exceedingly high, right?
If you’re the type of person who was a PM or engineer
at, you know, one of these fan companies,
and then you’re like, I’m gonna start a startup
’cause I see other people doing it,
then you don’t think, you don’t go into it thinking,
well, I’m just gonna create like a whatever,
something that’s like a nice small business, right?
You go in being like, I’m gonna raise series A
from Andreessen, and we’re gonna be, you know,
this product that just goes,
the next Snapchat or whatever.
And so I think that, like, it’s always a battle
against your own, like, the kind of devil
on your shoulders telling you, you’re not good enough,
you know, you’re not doing well enough,
you could be doing better.
And I think the way that you win that battle
is by really internalizing and realizing
that whatever happens, you’re gonna be fine.
And you’re probably gonna be the same,
you’re not gonna be happier or less happy, actually.
And now most people do not actually successfully
internalize that well enough, in my opinion.
But it is true, I firmly believe it’s true,
and it’s something that the sooner you start practicing
that in your head, really, you know,
feeling that and experiencing that in yourself internally,
then the happier you’ll be.
And that’s not to say that a lot of, you know,
people I come into contact with, like, friends even,
or people who work for me are like,
well, my drive, like, that need to win at all costs
is my edge.
But I really don’t believe, I mean,
maybe that’s true for other people,
but for me, I never found that to be the case.
It’s like, no, it was just like the kind of unhappiness
that was created around it that would make it
actually less sustainable for me to continue on,
because I was always, you know, you can’t,
human beings don’t wanna live in a high stress,
high anxiety, stay for too long.
That’s how you can burn out, right?
So startups are not, I mean, contrary to popular belief,
it’s not a sprint, it’s a marathon, right?
There’s these overnight successes,
Twitch came out of nowhere, eight years from
incorporating that company to selling it,
almost exactly eight years, right?
So that is a long time.
And in order to last a long time,
you need to figure out a way that you are okay
with what’s going on, and what’s going on
is always gonna involve bad things.
Like things, you know, there’s gonna be good
and there’s gonna be bad.
So if you don’t figure out a way
that you psychologically are okay with that,
you’re gonna give up, and if you give up,
you’re never gonna see it to the ultimate potential
that whatever your startup is can be.
– Great.
I’m gonna throw in kind of two last questions in here.
One is, you know, what are you reading these days?
Do you have any sort of recommendations, podcasts
that you like, kind of media consumption
is kind of a way to learn yourself?
– Yeah.
– And anything sort of especially super impactful
over the last couple years that you wanna reference?
– Yeah, that’s great.
So reading a lot, actually,
’cause I deleted all the entertainment apps off my phone,
including the browser, and I’d locked it
so that I don’t can install new apps
’cause I was a total phone addict.
That includes Twitch.
– Wait, how do you lock?
How do you lock your–
– So you can lock installing new apps,
you can delete the app store
and put a passcode lock on it.
– Oh.
– And I gave my wife the passcode,
or she put in a passcode, I don’t know what it is.
– Right.
– So I can’t–
– This is like a parental lock.
– It’s a parental lock, exactly.
So I don’t have control over my own phone anymore.
But the consequence of that is I read a lot more books,
which is good.
A couple of ones that have been particularly impactful to me.
Number one is this book called The Untethered Soul.
So this book changed my life.
It’s really about the idea is that you are not
the thing that you think you are.
Most people go through life thinking they are the experiences
that they’ve experienced, the thoughts that they have,
or the emotions that they have.
But really, you’re just the observer of these things
that are happening.
And by creating, it’s almost like you’re watching a movie,
right, like a movie that has all the five senses,
plus emotions, plus thoughts.
So like a seven dimensional movie of the just end life, right?
And I think that was a very important message to me
to realize, like an internalize that like actually
these attachment, these things that I think will happen
that will like drive happiness, like experiences or events
or whatever will never actually drive
true internal happiness.
So amazing book, The Untethered Soul, highly recommend it.
Another book that I think made me a much better leader,
I was this book I read called Leadership and Self Deception.
Amazing book.
The book, the premise of the book is really there’s two ways
to treat other people inside the box and outside the box,
but really I mean like without empathy or with empathy,
like treating them like an object or a person, right?
And the idea, the fundamental idea behind the book
is if you treat people like an object,
number one, they don’t like it, right?
But the second thing is, if you treat people like objects
who are just there to fulfill something for you, right?
Like at work, it would be like to, you know,
hit some number or metric or whatever, do some job.
The problem is that you will lie to yourself about
when there’s negative situations about what your role is,
you’ll self deceive, you’ll say,
oh, this person is 100% at fault
and I’m 0% at fault.
And I found myself actually doing that a lot of times.
I realized, you know, I felt like I was,
you know, had a high degree of empathy for other people,
but I realized that was for people who,
I felt like we’re performing really good
where my observation was like high performance.
But I wasn’t, where my observation,
where my feeling was that there wasn’t high performance,
I felt like I would slip into this like low empathy mode.
And the problem is that when you’re in that mode,
you don’t admit, what are the things that I have done?
What, you know, Justin, what are the things I have done
to contribute to that situation?
So examples could be put someone in the wrong job,
didn’t give them clear enough criteria for success or failure,
didn’t support them with the right resources, right?
There’s many reasons why I could have contributed
to some situation failing.
And I found that like I would lie to myself in those situations.
So, you know, that was a really important book for me.
And those are probably two ones I really recommend.
– That’s great.
Are you doing a lot of podcasts right now?
– Listening to them? – Yeah.
– Been listening to– – That kind of entertainment.
– Yeah, I listened to some podcasts.
I’ve been listening to some of the Joe Rogan experience.
– Nice. – And that’s probably the,
this is probably it.
I like, I just listened to one with Alex Honol,
where he’s talking about climbing, you know,
so it’s pretty interesting.
– I’m gonna ask you the time travel question.
So if you were today, an enlightened, repeat entrepreneur,
to go back to yourself when, you know,
you’re 22, 23, just getting started doing this thing.
You know, what advice would you give yourself?
– When I’m just getting started, you know,
probably join Facebook.
No, but the, maybe the real answer,
I’ve actually, you know, I don’t really regret
any of the, like, economic choices or anything.
I think I’ve had this tremendous opportunity
to, like, build and discover these new things
and build companies and I wouldn’t trade it for anything.
I think the thing I could have done better
or, like, learned, you know, back then is,
you know, self-improvement is a thing.
You should probably, like, work on that.
Maybe that’s number one.
The second thing would be–
– Stop eating pizza at work.
– Yeah, stop eating pizza at work.
Number three would be,
you should, you know, things take time.
Like, don’t be in such a, you know,
it’s not, like, a one-year, one-and-done,
like, no, you’re a billionaire, you know?
Like, if you look at the, let’s say,
any sort of, like, the Amazon share price
or, like, market cap over time, right?
It looks, like, even through, like,
the last couple years looks like an exponential curve, right?
And so, you know, if Bezos had been, like, your,
you know, like, 15,
which is a long time to be starting a company,
like, oh, man, I made it, I’m done,
like, I’m gonna retire, like,
well, you know, the company would look a lot different,
right, so, you know, things take time
and I have to constantly remind myself that.
I think humans, you know, here in Silicon Valley,
especially, but then human beings in general,
are wired to, like, always want the new,
you know, look for the new thing.
What’s new?
What are you, like, what’s your new thing?
Something that everybody’s asking about in Silicon Valley?
They’re always, you know, that’s a question here.
But the best entrepreneurs here,
the ones who have created lasting companies
and lasting value, they stick with their thing
for decades, you know?
And that’s what impresses me most now
and I wish that I had kind of realized that, you know,
before.
– Awesome.
– Better late than never.
(laughing)
– Awesome.
Justin, thank you for coming by.
– Yeah.
– Thanks for having me. – Really good discussion.
[BLANK_AUDIO]
Want actionable advice from a founder who has built multiple tech companies and has invested the time to be open, introspective, and transparent about lessons learned?
In this episode (which originally aired as a YouTube video), a16z General Partner Andrew Chen (@@andrewchen) talks with Justin Kan (@justinkan). Justin is a repeat entrepreneur who co-founded Kiko Software (a Web 2.0 calendar that pre-dated Google Calendar by 4 years); Justin.tv (a lifecasting platform); Twitch.tv (a live streaming platform for esports, music, and other creatives now part of Amazon); Socialcam; and now Atrium, a software-powered law firm for startups.
Justin reflects on his journey and shares 10 + 1 lessons he’s learned:
- The paradox of choice: choosing a focus
- Tradeoffs between B2B versus B2C companies
- Market risk vs execution risk
- Fundraising strategy: go big or stay lean?
- Managing the stress of being a startup CEO (again!)
- Seeking out mentors, coaches, and peers for help
- Intentionally designing a culture to avoid the pitfalls of “culture eating strategy”
- Things he’s still doing in his latest startup—and things he’s doing very differently
- Managing higher expectations
- What he’s reading and listening to
- Bonus: advice he’d give his 20-year old self
The views expressed here are those of the individual AH Capital Management, L.L.C. (“a16z”) personnel quoted and are not the views of a16z or its affiliates. Certain information contained in here has been obtained from third-party sources, including from portfolio companies of funds managed by a16z. While taken from sources believed to be reliable, a16z has not independently verified such information and makes no representations about the enduring accuracy of the information or its appropriateness for a given situation.
This content is provided for informational purposes only, and should not be relied upon as legal, business, investment, or tax advice. You should consult your own advisers as to those matters. References to any securities or digital assets are for illustrative purposes only, and do not constitute an investment recommendation or offer to provide investment advisory services. Furthermore, this content is not directed at nor intended for use by any investors or prospective investors, and may not under any circumstances be relied upon when making a decision to invest in any fund managed by a16z. (An offering to invest in an a16z fund will be made only by the private placement memorandum, subscription agreement, and other relevant documentation of any such fund and should be read in their entirety.) Any investments or portfolio companies mentioned, referred to, or described are not representative of all investments in vehicles managed by a16z, and there can be no assurance that the investments will be profitable or that other investments made in the future will have similar characteristics or results. A list of investments made by funds managed by Andreessen Horowitz (excluding investments and certain publicly traded cryptocurrencies/ digital assets for which the issuer has not provided permission for a16z to disclose publicly) is available at https://a16z.com/investments/.
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