#98 Sahil Lavingia: Observing the Present

Transcript from https://podmenti.com/t/fc8ae99cdab6bdee

I wish I knew earlier that like
My company was still my responsibility. No one was gonna fix my problems. They were investing.
Because they believed in me and they believed in my potential.
But it was up to me to to to still
sort of take that potential energy and turn it into kinetic energy. It wasn't a handout. It wasn't like
you know, you're gonna get these people to come in to your office and and help you solve problems day in, day out. No one's gonna make you rich. Like, you know, people people are busy.
Solving their own problems.
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My guest today is Sehil Living Yeah.
Sahill was the second employee at Pinterest and left to start building Gumroad, a service that's helped creators earn more than three hundred million.
We talk about the hardest skill to succeed in business.
What he looks for when hiring.
What it's like to try and build a billion dollar business, his worst mistake.
Patterns of success, patterns of failure, and so much more.
It's time to listen.
And learn.
You were born in New York, but you grew up in Singapore. What was that like?
Yeah. It was interesting. Singapore is a very unique place. Uh a lot of people who visit describe it like a
city playground where it's just insanely safe. It's
super clean, you know, people joke about the fact that you you know, you get
beat up for chewing gum or or whatever. Um
Which is
Not true, but
Not inaccurate.
Either kind of it it it's it's uh
It is a it is a good heuristic to describe Singapore, I think.
But yeah, it was just I think living in a place that felt so different from everywhere else. And Singapore, because it's such a young country.
It doesn't have the same
sort of, you know, identity almost issues that a lot of other countries have in terms of like this is the way that we do things.
Singapore if you read about Liquan Yu or any of the
founding story of the country and things, like they just pick and pull ideas from
Everything, you know, s libertarians I know describe it as like
A utopia because there's no minimum wage, zero.
There's basically a flat.
tax. I think it's around fifteen percent flat, no matter how much
You make, there's no capital gains tax.
Uh
And so libertarians love it. Uh, but then you know, the sort of more progressive socialist kind of people that I know also love Singapore because it's sort of
you know, they the eighty percent of the housing there is built by the government.
Uh it's it's a very
uh sort of top down
Centrally planned.
country, it's a single city state.
Country
And so I I I just love it because people love to
use it as an example of
their viewpoint. Like it's a really interesting kind of roar shark test for like the
For the the things that people like.
But you know, it's young, it's small.
And so in terms, you know, it's never been in a in a war.
And so I think there are just things that allow it to do to do things.
quote unquote better than than other folks.
And then I would say the other thing that I just, you know, took away from Singapore is just it's pretty ruthless. It's like a pro very pragmatic as a country place. They're very strategic about how do we grow this thing, right? Like how do we structure this place in a way that if you look at the GDP of Singapore over the last like fifty, sixty years, it's
like the fastest growing startup you've ever seen, you know.
Well that was the from Third World to First, right? Liquan U and and sort of like his
Unprecedented taking a country
in a generation and basically
uh making it wealthy.
Totally. And you know, there's a there's a lot of things you can't control, like they're just you know, where it's located.
on the map is really important.
in terms of the trade routes, Singapore's sort of like the largest port in the in south south east Asia, but
It took a person, I think, just like George Washington, right? Like it you need
the ingredients, but then you need kind of the the chef as well to kind of put them together.
How long were you there?
I was there from age five to seventeen.
So most of my childhood.
What was school like there?
I don't I don't know how to compare it because I that's the only context I have. I I think it's relatively similar, uh to
to schools here, um though certainly like doesn't have some of the same issues around
you know, what you've been reading about racism and
anti Semitism and sexism and all these things. Like Singapore doesn't feel like it has much of the same bag. It has other other issues
For sure.
I would say
the the emphasis there was so much on getting a secondary education
It was like
Everyone knew without any doubt that they would go to college.
And it's a very it's very sort of financially motivated place. And so typically people will pick the jobs that will make them the most money.
It's sort of very uh
Very capitalistic in that way.
It's interesting how those expectations shape outcomes too, right? It's like you're expected to go to college there, you're expected to perform academically, I believe. I think expectations cannot be underrated, and I think
Uh and
your peer group also can't.
be underrated. Like I I think there's so much emphasis on
on sort of the system that you're a part of, uh you're
sort of your set of teachers, et cetera. But honestly, I think the biggest thing is just like you're kind of the average of your five friends, you know? And if you
hang out with certain people, you're gonna end up in a very, very, very different place.
Based on based on that kind of like that osmosis that that you'll go through and the sort of like this this sort of socialisation.
you know, that that you'll have as as a kid. And I think that happens super early.
And certainly, yeah, Singapore. It just, you know, it's it's a pretty ruthless it's a pretty ruthless place. Like the idea that
There's no fat people, for example, in Singapore. It just like doesn't really exist as a concept.
And I don't mean that in any sort of derogatory way, but there's just people in general there aren't overweight, uh, and part of that is
in in the local school system, if you
are overweight.
You go through a a program.
Like yes, part of you skip lunch.
And you go through a program
that you basically run around a track instead of eat lunch. I mean it's like a sort of a
a regulatory a regulatory system and you know, there's also uh national service. Everyone
who's Singaporean, if you stay in Singapore, I chose to leave and go to school in the US.
you have to go through national service, right? So you spend two years
becoming, you know, sort of like a
a perfect adult, quote unquote, right? Like you learn these things, like in general, people who go through that are less likely to
to get into trouble and and things like that. So there was a lot of
It's it's hard to unpack exactly like, oh, you know, if we took this and applied it here, you know, it would fix this problem, but there's just so much culturality around.
Just holding holding the people to a very high bar.
And then when you do that, like the next generation, you know, is brought up with these sort of values and is willing to do that for the
sort of for the next generation, et cetera, et cetera, so.
I wanna explore something you said there about sort of the you are the product of the five closest people you hang around. How do you use that information to consciously
choose um the people that you're hanging around.
I'm really mindful of
of that. Oh you know, like in terms of
The books that I read
uh the people that I listened to
uh the tweets that I follow.
I think
It's
It's super important to
to really, you know, it's sort of like you are what you eat, right? The the companies that you work for.
I think like I've never read a book and and and come out of it being less convinced of the argument.
Even though I was
not on the side of the argument. Like when you spend that much time
sort of looking at a subject from a specific perspective.
you just end up becoming more empathetic to that point of view.
And it's like doing that.
en masse, right? When you go on the on your phone, you're kind of seeing
the way that a certain group of people
see certain things. And I think this has actually sort of been accelerated with COVID because you don't have maybe some of the back and forth. You're just you can't, you know, it's sort of this very asynchronous
Medium.
And so you end up just like absorbing
All of this content.
And your perception is your reality. So I think you just inevitably
Inevitably kind of
become closer to
those sorts of people which I think can be a great thing if you wanna be a great
business person, for example, you can read books by great business people and of course they're selling things, like you kind of
have to be mindful of maybe what their incentive structure might be.
But you'll get closer to
figuring out like what are the sort of attributes that make
Someone like Jay Z Jay Z or someone like Steve Martin Steve Martin, right?
And I I spend a huge amount of my time reading those sorts of
Those sorts of books as well.
What about the people you physically hang around with? Like do you call sort of friendships when you're like this isn't serving me? Or how do you think about that?
Yeah, this is something I struggle with a lot, I think.
There is a large expectation around friends and like what friends
mean and you know, S Silicon Valley is kinda funny because there's this concept of
we're friends and I like to joke that we're startup friends because it's such an overused word. And what it means is like we met once in person for coffee.
And if they you know, I need something from them, I'll send them an email and they'll reply to my email. It's not like we hang out
at the bar, you know, like you know, like all these sorts of things. Unless it's sort of some situational thing that arises typically from some sort of business reason. And that might just be a differentiator between friends in
School and friends, you know.
In adult life.
I'm not really sure'cause that's sort the only sort of career path that I've I've sort of taken.
But yeah, it's it's
I always struggle with with that idea that we need to be friends with everybody.
Uh there are people that I talk to all of the time.
But I wouldn't consider them even friends of mine. We just happened to be
valuable for each other, very symbiotic relationship.
And then there's other people that I'm friends with that
I would consider
Close, close, close friends with.
that I haven't talked to in in months. Uh and so I r I really I think those can be separated.
But yeah, I I spent a lot of my time thinking about how do I spend more time with certain
Pipo
Which I think can be a trap because you don't want to
You know.
get into this this place where you're just like, How do I meet this person? I don't think that's the right approach.
But it's more like how can I figure out how to become closer to the type of person that this kind of person is.
And in general, if you do that over time.
I feel like opportunities to meet these kinds of folks will will will come up and show up in your life.
Organically.
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Where did the idea from Gumroad come from and how did you get started?
Yeah, so Gumroad
I wanted to sell this pencil icon that I designed for a Mac app.
And
I had a Twitter account, I had a dribble account, I had a few thousand followers. This is twenty
Eleven.
And I just wanted to sell them this thing. I kinda called it like a lemonade stand. I just I don't need a whole storefront on it. Like I need didn't need all of this infrastructure.
I just needed like a little table and you know, I wanted to sell this icon for a dollar and and and you know, these people who are already following me
you know, I can just share it with them and they can choose to buy it or not and
you know, they they enter in their credit card information.
They get an email receipt with the download or they get the download maybe in line even.
Uh, and just made it super easy. And so
I thought that would exist and it just didn't exist. It f it felt like a very large disconnect.
Where I was like, Oh, I I'm gonna go sell this icon to this audience.
And then it wasn't possible. So that you know, that was Friday night and then I ended up building gummer that weekend.
And then launched it.
Launch it Monday.
On Hacker News and
It did.
well, I think, uh, and then, you know, a few months later I ended up
Starting starting to work on it.
full time race raise some money from folks like Naval, et cetera.
That's what I've been doing since.
What was the process of ra raising money like?
I mean this is a
This is like I don't know, a really good example, I think, of like figuring out how you get to spend, you know, time with certain folks, like the way that I structured the life my life before before I even I wanted to fundraise or thought about it as an idea. I felt like I wanted to be a founder and so I spent a lot of time hanging out with founders, hanging out with early employees, working at an early
stage startup. I think that's sort of the best thing that you could do.
Yeah, I left
US C to go do that.
And so I had a network just from building stuff, meeting with people, people wanting to recruit me for their companies. I'd started to build
a a relatively strong network of people like Naval and Seth Goldstein from Turntable and
And Samuel Shaw from Haystack VC now and
when I w sort of had the opportunity to raise money, when s one one investor suggested, like, hey, this thing looks really cool.
Have you thought about
doing this full time, I know you're at Pinterest, but you know, this is certainly something you think you know, you'd probably be able to raise money for. And I was like, I really had no idea that I could do that. It was not in my mind at all.
That I could be a founder that early that quickly.
Uh, and so I said yes, and then I just told all of these people that I had met out of the context of raising money.
It's like hey
We met about this
Three months ago or six months ago or or
Or what have you.
I have a startup, like, you know, I'm st
That I'm gonna raise money for? Are you interested in
It was honestly a a relatively smooth transition because I built up these relationships with people around just talking about product and talking about there was no agenda.
I wasn't selling them anything, so I'd sort of already
effectively sold them on my abilities.
To build stuff.
And be really committed to that path.
And so when I decided to raise money
It I'd almost done all of the work.
You know, accidentally.
And then it was just sort of like going through like okay, what are the terms?
You know, what are the sort of the like the legal
paperwork side of things, but it was a relatively smooth, smooth process.
What do you wish you knew about raising money that you know now?
I mean I I I I would say I I think every f founder thinks that raising money is gonna change their life. Like you're gonna get all of these phenomenal people on your cap table and you're gonna
hang out with them all the time and they're gonna help you, you know, recruit and build product and figure out go go to market strategy and
The truth is, like, all of these folks are very busy. Some of them are running their own companies.
Uh, many of them
or in many, many, many companies.
Of which you are
At least not in the beginning, one of their
sort of top.
few and and the way venture returns work is it's sort of a power loss. So if you're not
They're Uber.
You know, it's a different
the way they think about you might be a little bit different. So I I wish I just knew that. I wish I knew earlier that like
My company was still my responsibility. No one was gonna fix my problems. They were investing
Because they believed in me and they believed in my potential.
But it was up to me to
To to still
sort of take that potential energy and turn it into kinetic energy. It wasn't a handout. It wasn't like
you know, you're gonna get these people to come in to your office and and help you solve problems day in, day out. And I this is an experience I've talked to so many founder friends where they feel like
Here's the sales process.
is is so good. The this is what they do, right? They're selling cash to get on your cap table.
And they're really good at that.
Uh, but it's like the second they sell you the car.
They they're they're they've sold you the car. I mean they you know, they've done the ninety percent of the
of the of the work if you know, to sort of precede it investors, it does change a little bit later on, I think.
And so I just wish I knew.
Not in any
In any
in a way that says oh these people aren't helpful or whatever, but just the incentives and it's just the model in which they operate
And so I can understand okay, this is as a founder
what you expect from me, what I owe you, quote unquote, and how I should
Sort of go about it.
But you learn you learn pretty pretty quickly that that that that was the expectation and that you just need to
Like anything, like no one's gonna
No one's gonna make you rich. Like you know, people people are busy.
Solving their own problems.
were the expectations on you that you would become sort of like this billion dollar business that you you haven't accomplished yet?
Uh and what's that been like?
Yeah, it was, I think. I mean
Silicon Valley is
is a game of finding these crazy outsized returns. It's
You know, the the sort of common adage is you know
thirty percent of your companies die.
thirty percent of your companies return less than one X. And so you kinda need the last third
And really the top ten percent of the of of the best that you make to return over ten X of the sort of initial principal capital.
And often a lot more if you want to return any meaningful returns to your investors,'cause this is an illegal liquid asset class, right? You're giving money.
to a to a to a venture capitalist as a as a as an L P and they're gonna hold that capital for
ten plus years, right? So you kind of expect more than market returns if you're if you're
If you're signing up for that.
So yeah, that was totally the expectation. And that's not just the expectation. I think some people really focus on and on venture capitalists and the in the zeitgeist, but
It's also the expectation for the early employees because the early employees might only have
half a percent of the company, one percent of the company, two percent of the company.
And so they also are looking for I mean they're turning down offers for you know from
Facebook and Google and Uber at like you know, for hundreds of thousands of dollars to work at your
Your rinky dink startup.
There's a there's a whole system I think is modelled off of
For this to be worth it for everybody that you need to get signed up.
to even get to the to any end result that's interesting.
You need the promise of or the potential of there needs to be a billion dollar plus outcome here.
That's it's kind of like when you look at the music industry.
you know, or the NBA or anything.
It's not that everyone has the expectation that they're gonna become LeBron or Kanye West or anything like that, but
The idea that it's possible
And that one person is going to
Win the hunger games.
is going to really kind of it drives the level of
competition and
sort of work ethic that I think you
frankly, just don't get when you don't have
those those those crazy outcomes as a as a possibility, right? Like Jeff Bezos doesn't need two hundred billion dollars or whatever he has now, but
For some reason
No one does. I don't know what you do with that much money.
Um
But for some reason it's
Still.
cre like America I think
It still has like this phenomenal culture of
Innovation that I think is largely driven by this
Weird.
relatively abstract.
number on the on the wall that everyone can see.
You know.
Did you feel any sort of disappointment or w or did they make you feel disappointed in terms of not accomplishing that as quickly as maybe it was anticipated? I mean
Yeah, I mean
They're
There definitely was some disappointment. Uh I mean I had
I had so many wins so early.
I dropped out of school and then I was the second employee at Pinterest at eighteen and then I started a company at
nineteen and raised a bunch of money from really great investors and
And you know, raise like ten million bucks.
by the time I was twenty one or something like that. So I just felt like
If this was gonna work.
These are sort of the things that you need to see.
Right. But but that's kind of a delusion. It's like when your team gets to the semi finals. Like it doesn't you still have to uh you're still
Less than halfway there, right? Like you there's still work to do.
uh but but you have so much evidence that you're like, oh this mu you kinda start believing something that might not be true. But it was it was mostly internal disappointment. The nice thing about the portfolio theory that VCs have is
They don't care that much about you if it doesn't work either, right? So
They're all they're sort of focused on
on other things they're kinda content to let you
figure it out. At least the good ones are, they kinda understand that.
I think um
But it was certainly d I mean, it was certainly disappointing, I think.
To admit
when we did the layoffs, that was like the big moment.
that you know, there's really no going back from that.
Right, like you're sort of saying
Hey, this thing that we all signed up for. Like we literally cannot
possibly keep going on this path. We need to you know, we cut
seventy five percent of the staff from twenty down to five people in twenty fifteen.
And then TechCrunch uh wrote about it.
And so, you know, it's just like oh wow like the you know, you we really we really failed and
And even though failure is such a
meme almost at this point.
in something you read about when it happens to you, when it really, you know, even though you knew the odds coming into it, when it when you realize like
Oh, you're part of history? Like
This is uh you are the example that other people might be referring, you know, when the it it feels very, very different.
Do you actually feel like you failed? I did for a long time.
Yeah, I mean
You know, I was living in San Francisco, everyone's raising money and everyone's talking about how many employees they have and how much revenue they're doing and how fast they're growing. So it's certainly in that
Cultural context it
Feels like
You show up and it's like how's Gummer go? I mean that's the qu those are the questions
It's not malicious, these are the questions that people tend to ask when you go to these house parties. Like
Yeah.
Like how much of you know, what are you doing? Oh, where do you work? What do you do for them?
Gauging your
sort of like where you are. Where are you in the hierarchy? How useful are you gonna be to me? Yeah, something, you know, this is I I assume it happens in any boom town, right? Like people are there for a specific reason.
Typically sort of
accelerating their career.
It definitely when you hear that question a lot and you're
kind of responding to it a lot.
you you kind of end up
sort of conflating that with your whole identity.
And it took me leaving San Francisco.
And
moving to Provo, Utah and and and there the questions were very different.
You know, it was like hey
Are you married? Where are you from?
Do you go to church?
Just different different kind of questions. It's it maybe a similar thing's happening. They're also trying to figure out where you stand on the
on in their own journey. Where do you fit in their journey, right?
Uh and they're they're also trying to form a connection around the common topics that you both are probably interested in.
But
after a while of that, you f you I kind of forget, Oh, I'm I I am a COVID. Like I've that all kind of like
I almost forgot about and and really that I think distance was what got me to write that

I wouldn't I would not have been able to write that article like sitting at a coffee shop in San Francisco.
Right, like just the
The ego, the
The self
Consciousness of it.
I think I needed that distance to be in the middle of
people who didn't really like to to be so outside of that.
to to to really kind of look at it.
you know, and feel like I'm it was almost like an out of body experience where I was kind of like analyzing
the life like I was writing
a biography of
Of somebody else, you know.
It was so f foreign.
At that point.
Th there's people that sort of ascribe your value to your position and what you do and what you can do for them. And then there's people who want to know who you are and and
sort of have a a relationship with you. And then I think if we hang out with people that
uh ascribe value to our our rank or position or some sort of authority or knowledge that we have, then we become wrapped up in that. And we we have to see ourselves as that. And that can be a very
Very bad thing over the long term. I'm curious as to um what your worst mistake was, like what led to it.
Uh, how did you recover from it and how did you learn from it? What happened?
Yeah, I mean I think I mean, to your point, just quickly, like, you know, it kinda goes back to what we're talking about Singapore and like the average of your five friends and stuff, right? It's sort of the same thing. The questions that everyone in your group is asking of themselves ends up
being the question that you're gonna start asking
yourself too.
In terms of the worst mistake.
Definitely
Like one one that
is very
raw because it has like a very specific number tied to it is we
We started racing the series B, we started
Talking to investors about it.
And so for context, like we raised a seed round of a million bucks, we raised a series A of seven in twenty twelve.
Kleiner Perkins and then in twenty fourteen, twenty fifteen.
We're growing sixty percent a year, we thought we had
It wasn't gonna be easy, but we thought we had a shot.
And we started talking to investors around the series B, we wanted to raise maybe fifteen, twenty or so million dollars.
To keep going.
And very quickly realized like this was gonna be a pretty hard uh
A hard path if if we were to succeed at all.
And
Concurrently.
Our office lease was expiring.
And so we had this thirty three thousand square foot office we were p spending ten grand a month for
And we had the you know, we and we were growing.
You know, startups like you have to signal that you're growing. You can't say, Hey guys
We're gonna take a break, figure this thing out.'Cause
Everyone's gonna look at that.
And say oh these
Like as a venture capitalist, you don't want those people. You don't want to back those people. So you're you're you're
You sort it becomes a self fulfilling prophecy when you do that. So you have to kinda keep going, assuming that things are gonna work out for at least a certain period of time.
And so that's what we did. We signed a lease for a new office.
So we could scale from twenty people to forty, fifty people.
Or so.
It was twenty five thousand dollars a month. We paid a big deposit, six figure deposit on it.
and moved and then, you know, a few months later it was like
We're probably not gonna raise money. We're not we certainly are freezing hiring now.
And
What are we gonna do with I mean the office was just this overbearing thing. You like walk into a cavern, it felt like
You know?
Uh it was it was brutal. And then when we
We went down from twenty to five. Guess what? We're still in this office.
This office could hold forty plus people and there's like four or five of us a day.
It was
painful. And so ultimately I I had to make the decision to kill the lease completely.
And we lost, you know.
Mm.
couple hundred thousand dollars. And uh luckily we we've we found a
we found a new tenant to come in, but we you know, we still lost we ended up still losing, yeah, probably a hundred or so thousand dollars through the through that process. And what I should have done
In hindsight.
Of course, hindsight's twenty twenty, but what I should have done is
told the team, Hey, we're not moving offices, we're just gonna renew this lease.
But then again, if I followed that on you know, that advice, who knows what would have happened. V Cs might have pulled out even sooner and
You know?
it could have been it could have been worse. Uh but that definitely very painful.
V and and that w really that taught me this very deep lesson.
Of like commitments and debt and like really feeling like you owe someone something. Like I really don't like being in that place where I have to establish.
This almost goes back to what we were talking about before too.
Or you have these friends and you kind of
There's a sort of an expectation that like you're gonna be friends with someone for life, or it's bad that you kinda go separate ways, you know, something must have gone wrong or something.
Uh we still have, you know, in marriage, the divorce is still maybe that's fine. Maybe it's just what happens, you know, that might be the right thing.
I think we we definitely have a lot of attachment to these ideas.
And that's another one of them, I think. You know, it's it's the same thing. It's like I I really
Try to form build relationships with people that feel at will.
They feel like we're both reupping.
To keep this thing going.
on a very frequent basis with my employees, with with uh my investors, with
with other folks that I talk to. It should feel very
Oh not transactional. It feels transactional.
Uh and maybe maybe that maybe it is transactional.
But it it doesn't I don't know, it feels just voluntary. It feels like something we're signing up for and then that makes that makes me feel a lot better about it.
And you guys are profitable now, right?
Yeah.
In twenty fifteen we we
We sort of January we knew this was gonna be brutal.
We spent nine months, we raised a small bridge round, two million dollars at four X liquidation preference, uh, from from Kleiner and uh and s Mark Cuban and some other folks. And
Spend nine nine or so months.
really trying to make it work, like ch sort of focusing almost completely on what can we do to grow the business faster.
And then we we failed to do that. And so luckily I told the team like
You know, they have full awareness that this was
Likely the path was gonna lead to mass layoffs to save the company. And that's what we did in October, November. We we downside from 25, got rid of the office.
Finally found a new tenant.
And
You know.
Got profitable.
made ten thousand dollars one month and it was like
A dream.
Uh'cause not only do you make ten thousand dollars, your runway goes from
you know, a certain finite number.
to infinity.
Right. And
Excel starts erroring out and you're like
Yes, like this we can we can do this forever if we need to.
And that's roughly where we've we've been since, where we're kinda growing. We're doing it in a way that we think we can do sustainably without
betting the company to to do anything.
Uh certainly means we have to
You know, we're constrained in many ways. We can't just say, Hey, we're gonna launch this totally new product, put a team of twenty on it.
Um but so far it's it's worked.
Worked pretty well for us.
Do you wish you would have done that sooner?

Yeah, that is that is a decision that I think, yeah.
Uh I I and this is
As I sort of
do more investing, it's something I communicate to to founders a lot too, is like, look, this is what you need.
to stay on this path.
This is the venture back path.
It's actually relatively objective. You need to be growing. In the article I say twenty percent month over month, but it can be ten percent. It just needs to be
sort of exponential or
Or so.
or polynomial or whatever the correct math term is.
And if you're doing that you can stay on this path. If you're not doing that
It's gonna be tough. It really you know, maybe s pre seed seed A a little bit different.
But if
you know, at sort of at some point around series A, series B
That becomes sort of
like the end all be all, it becomes the most important thing in which all of the other things can't outweigh that.
And I I knew that. I I saw that in the numbers. Like that was evident to me, but I didn't make the connection with how important it was.
How fundamental it was.
For this path and I wish
You know, a year.
Before I did or so.
You know, we said, Hey, look, we're not growing as fast as we need to be growing.
Like let's pause.
We don't have to do anything drastic'cause it's still early.
But let's pause, let's recalibrate.
And you know, and let's let's figure this out.
And certainly yeah, certainly wish I I would have done that. We would have avoided a lot of a lot of pain.
But
It it is what it is.
I've spoken with a few entrepreneurs who've sort of been VC backed and then uh one way or another got off that train and then
came to a path of profitability that was sustainable and
It it's almost unanimous that everybody wish uh they just would have done that from the get go.
instead of and maybe that's just a you know an outcome bias, right? So you you didn't hit the sort of like
big massive unicorn, you know, thirty X.
uh win and so you you're left with profitability, but lots of companies die trying to get to that stage too.
Yeah, totally. I I do think there is a level of outcome bias. There I think there is also a level of
One of the reasons
To raise money is a social one where it gives you a sort of credential.
that is very useful. I can still to this day go into a room and say, hey, I raise money from Naval, Max Leftchin, Client Perkins.
Kisaka.
First round.
And people will take me seriously for that, right? Just because of that, yeah, the signal value.
And so there is like this kind of
I think people might
Uh
sort of forget when you when you get through the whole thing that you're still taking advantage of some of those things. And maybe, you know, it's kind of like
Maybe you should get into Harvard.
and and put the you know the acceptance letter on the wall.
But not actually attend, especially now. Right. It's sort of that. Like maybe you should t like say that you they were i gonna give you the money and not take it or something. I don't know how you would frame that in a way that doesn't make you sound
Bad, but
uh or maybe raise raise a small seed round or something. Um but again, like being that strategic about it because it feels manipul you know, like venture is such a long term game, you can't
You can't think like that and I wouldn't recommend it.
But
There is an outcome bias. I mean, I I do agree with you almost every single person I meet who runs a profitable business.
Especially one powered by software.
they wouldn't trade it for the world. And frankly, like their cash flow looks better.
than most folks that I know who are
On paperworth a lot of
A lot more money.
I still haven't resolved that for myself because I still feel
That
sort of aspirational quality, right? Like I still feel
There's something about
stripe. Like there's something about Airbnb. There's something really cool about building something so meaningful. And I think part of that for me is
It's a it's a unik experience.
There are a lot of these other businesses and
They're great and they give you like a phenomenal quality of life.
and tons of freedom and time. And and and certainly if you're if you are are running one of these other companies.
You don't have a lot of those things. You don't have a lot of freedom. You don't have a lot of time.
Like you're living in San Francisco.
regardless of what happens with Covid and remote work because you need to be there.
But yet there's still something about that. I think it is that like you you have a certain set of experiences.
When you get to this place
that people like me just frankly want. Like we want to hang out with these sorts of people and have these interesting conversations.
And it makes it easier to do that.
But it it is weird. It it fe it it it does feel like even even
Acknowledging it, like being aware of it doesn't make it
go away, you know?
What do you think is the hardest skill to transfer to other people that's necessary for success in business?

Yeah, the the skill that's been really top of mind for me right now.
Is
The ability to save other people.
Time.
Basically what I mean is
There's certain people that go about their lives. I try to be like this.
But they just
operate in a way.
That
Yeah.
requires less of everybody else for them for the equivalent amount of success in that relationship.
Right. So
For example, someone who sends calendar invites, someone who's very diligent about taking notes and following up and
you know, people like you you put like the link to to have this conversation right into
the the Google Calendar invite a lot of people. Like they'll just put in the email. I'll have to go find the email. Like there's just a level of
Care?
It feels like you're you're almost like
It's like a concierge service for like the getting to spend time with this person.
And then there are there are other folks like the they're just being responsive. Like there's just things that like
lead to a a less
l less level of stress.
in everybody else around their lives and it's so rare. It's so rare I found
And I think it's because everyone else is also trying you know, is time very time sensitive too about their own time.
And so they end up
sort of operating in a way that's saving them time by sort of maybe pushing that burden onto other folks, right? You're sort of like playing hot potato with the task that no one really wants to do, but it's the people who are like, I'll do that.
I think that I think people underrate when you're that type of person.
you know, as a as a as a CO, as a founder, those employees that do that
We'll win.
Like they will get whatever they want.
Because
Those are the folks I really want to surround myself with because I care about, you know, my quality of life and my time.
And as a as a investor and as a as a even as a
I don't know, as all of these other roles I really like how can I save you clicks? How can I save you time?
Uh like when I send calendar invites, I put my name first instead of the other person so that
In their calendar it shows up.
You know, and otherwise you have all these countervice of just your name and you can't see who you're actually talking to. It's just like small things where I'm like, How can I just really streamline everybody else's life?
And the beauty of software is you can now use a lot of software, like
Calmly and
Zapier and and these
air table, et cetera, and these tools to like hook up these things so that everyone I think can operate like as if you had
A full time Yay.
running your life for you.
You just now pay.
couple hundred bucks to three or four different tools that
Give you that.
That's actually a even better experience because software
Is often
A little bit more.
uh foolproof than than than a human being.
Yeah.
I like how you you said that. That's something I I've thought a lot about. Um
And and I
find myself lacking in some areas, but definitely there's a lot of people who are more thoughtful about how they approach it from the other person's point of view.
Which is how do I make this easy for them, especially if you're you're asking them to come on the podcast or you're asking them to do something for you. Like you're doing me a favor.
Uh, I don't wanna send you fifty five emails trying to schedule it. I definitely don't wanna
you know, make it hard for you to hop on board and follow the instructions and like do all of that stuff and
But there's a lot of people in life. Like I remember going through this before when people would be like, Let's go for coffee. And you know, it's like thirty-five emails to go for a thirty minute coffee. And you know, at the end of the day, you're like, That's ridiculous. Like I don't want to do that anymore. I just stop replying to those. Yeah, it's it's it's like when people ask you, even people who I know.
They're like, Hey
Do you want to catch up next week?
And I know.
That they have a reason for this.
But they won't tell me the reason. And I always I I I just ask people now, I'm like, hey, what you know, what what do you want to talk about?
I don't know, it's like a power information asymmetry thing. But I think it's mostly just time. It's mostly like
I wanna I need to do something. Hey, Saho, can you talk about this next week?
Not really maybe even thinking about the fact that like you know exactly
You're gonna show up and know exactly what we're talking about, and I'm gonna show up and know nothing. And by the way, if you tell me
I'm happy to do the work ahead of time. Like I'll go read stuff. I'll like I will get you the answers.
So when I show up
Uh, I can I and then the other great thing is maybe we don't even have to have the meeting. Like maybe everything that you need for me I can just give you.
But you don't give me that opportunity. And so there is this like interesting like
People who view time as
the thing that they're trading and then to people who
sort of like can can transition to value.
For example, there's a if you're a founder
You you want a hundred thousand dollars from me or something like that.
you know, as you mentioned, like you're doing me a favor and it's like how can I
Like how easy can you make it for me? How easy can I make it for you?
And there's certain founders who make it so easy for me, I just reply to the email and I just say, I'm in for
For that. Like C seeing.
you know, Angelus to to wire the money. Like I they made it so easy for me. They gave me all of the things that I would want.
And then there are other folks who are like, Hey, I have a great idea.
Do you have time next week?

Sign this NBA. Yeah, sign this NBA.
Th there's also a l another level to this, which like outside of maybe professional relationships, but there's people who make it difficult, and then there's people who actually like
It it it's not a conscious process, but they make it exceptionally difficult. It's like they wanna go to dinner with you, but they want you to convince them to go to dinner.
With you. You know what I mean? Like there's a there's another layer to this, which is like
It's not easy and it's not middle of the road. It's actually quite complicated. Like you're put on the
Now I have to convince you sort of side of this.
Yeah, it's weird.
Um, wanna talk to you, w what other skills do you look for when you're hiring?
Communication is a huge one. It's similar to that, but people who overcommunicate, people who are
always thinking about
you know, the next day, the next week, the next two weeks, the next month, the next year.
And telling me
What they need from me.
how they feel about our relationship.
People who are very good at doing that.
It's it's it's low stress. It lets me
solve their problems before they need them solved potentially.
It makes me feel confident that they're in a good place and that they have what they need.
It's it's like static electricity, where like you you know you ever go too long without touching something, you hit something and you just like your like skin fries for a second.
It's like but if you did that all the time, it would never happen. Like
That's how I think about communication, especially within a within sort of like a high stress, high functioning organization.
Where that's gonna happen.
very quickly and you need to constantly be like tapping and like being like, hey, this is what's happening now, this is what's happening now, this is what's happening now.
And so I think people who are really good at
sort of ambient signaling saying, like I don't need to ever go to them and say what's going on. Like I just know. I wake up, I check Slack, I do whatever, I just know what they're doing.
To me, that's the dream. That is just like a phenomenal, phenomenal thing. I think an ability to write really, really well is key to that.
Yeah.
Part of that is just the medium in which so much of this com communication happens is via writing, especially now with remote work, et cetera.
Um but in general I just love when people
When people do the work of
You know, not just sending me the email, but writing the email, revising the email, revising the email, sending that email.
like the the the the the brain waves that they they've sort of like spent on that.
with the context they were already in is going to save net net save so much time for everybody involved. And then the the level of conversation is so much higher because instead of going like
It's just like
I'm gonna spend five minutes on this thing, but when you get it, it's already gonna be at like level ten. Because it's already at level ten, I can
Get it to level fifty.
Yeah, and and I'll give you the time that you gave me. Like I'll I'll I'll I'll pay you back.
very, very quickly and will build a very high quality
Relationship.
I would also say like
I like people who are very
is kind of transactional, frankly. Like I like people who are like I'm here
There's
To do this job, this is what I came here to do.
I'm really excited about speeding up the site. That's all I care about. And
like ninety nine percent of our conversations are around that.
Uh, and I spend you know, I might be working with these people on a daily basis.
And so I think I I like that too, when people don't feel the need to package up.
or bundle a relationship and say, Hey, we're co workers, so we need this, this, this, this, and this. We need you need to come to my birthday party, you need like
I like uh
You know.
And that's definitely a change for me sort of ten years ago, but I like people who are like, This is the way that we interact.
Like we talk every day, but it's about
investing or it's about you know, we talk every day but it's about
this other thing or, you know, and and and and and sometimes it's just like totally random stuff. Like there are people that I would never consider
quote unquote friends of mine, but like when I need to talk about like oil painting or something, like this is the person that I talk to and we'll talk for hours about it.
And then it might be like
Six months until we talk again.
And it's it's fine. Like we might even forget that the other person exists. And and I I actually think like a l life built of relationships like that, it gives you way more relationships.
And it you know, it it's sort of like having a a friend group of
thousands of people or having a company of all these sorts of people.
So I really like people who think like that, where they're very sure about what they want. They're feel they feel very good about where they're at in life.
And all they're looking for is this like is our relation to Phil like one thing.
that they need. They're trading.
X for Y.
And I just I I really like knowing that that's what someone is expecting of me. And I can just offer that.
And feel you know, and and feel really good about that.
And f and focus on that, you know? Instead of it's like when s someone's like
How can I help? You get nowhere.
But if you say, hey, I need help with this very specific thing, an intro to X, I can do that. Like that's I I'll do that, you know, just forward me an email.
you know, with the your the blurb in the deck and I'll forward it and ask for an opt in. Like that's that's purely automated. I'm that's that's purely a
a process that I go through. I could I could at some point and will automate that completely.
Agree, that that that's also making it easy for you, right?
Through investing and through Gumroad, I mean you've dealt with
probably thousands of entrepreneurs at this point. What are the common patterns of success and failure that you've seen?
Yeah, I think w one big one is is they build stuff.
They actually build stuff. In the early days, it was the it was the only group of people that I hung out with. Like I wasn't just hanging out with startup people, I was hanging out with the people who
went through some stuff to get there.
Um, it's like often the people the best people in the industry are the ones that didn't go to school for that industry because it it means that they had to cross all of these things.
To get into it.
Um if that makes sense. So people who people who build stuff, I think I was surrounded by those people when I get it started getting into it more and meeting thousands of people.
Realize a lot of people don't actually
build stuff. They don't know how to build stuff.
they need help. This kind of goes back to what we're talking about again. Like, you know, they're people who need all of these things from other people. And I don't like those people. I like the people who are like, I I want this for my life.
I wanna build a company. I wanna build an app.
I want to be a musician. Like it could be I want to write a book.
I need all of these things from other people in order for me to do that. I mean
That is
a very uh
uncontrollable way to live your life. Right. Like to to say I w it would be the equivalent of saying like I want to make a movie.
I have a great idea.
Right, like and and the world is full of these kinds of people. And so that's a big one. It's like well
Make a movie. You have an iPhone.
Like w show me, show me like a cool thing that you've made. There's TikTok now. I mean like there's things you can even put this stuff on.
Like show me what you've made.
Uh there's a great book, Rebel Without a Crew.
by Robert Rodriguez, who directed uh Alita Battle Angel, a taxi driver, and and he it's it's basically he talks about his journey and it's it's like it's like the lean startup apply to filmmaking or something like that, where he just he literally says
Okay, I live in this town. These are the things I have in my town. I'm gonna make a plot.
That involves
These
Things because that's what I have right now.
And then I'll make another movie, you know, like we'll we'll take it, you know, it won Sundance or whatever. Like it it
That's what got him started. And and that those are the people that I look for. The people who want something so badly that they just figure out.
How to do it.
And they're okay with like not maybe a sort of
having their first thing be just like the dream project. They just get started.
And then they
they figure things out as they go. And so building stuff, people who don't ask for permission, people who have hard skills
people who really try to save people time and are are really feel grateful.
Um, you know, like they they feel like, wow, I'm so lucky to be in this place. Like how can I make it as easy as as possible for everybody?
People who don't think of it like a numbers game where I just need to send a hundred emails and what three people are gonna say yes. It's like
I'm gonna send three emails, I'm gonna spend three hours on each one, and all of them are gonna say yes. I I think that's possible. I think
a lot of people underestimate how possible that is.
And people who read a lot. I would say this is the other thing, is people who
And it again sounds I don't know, like when I say these things it it makes it I'm like
These are just basic expectations I have.
Almost, but it but you might be surprised at like how few people
deeply read about
Anything, let alone their subject. I mean their own
industry
Their owners.
don't you know, the the set of problems that they're interested in. Someone might say, Hey, I'm really interested. Like I
From their tweets, it seems like they're really interested in healthcare. Like they think healthcare is fundamentally broken. It's totally messed up in the US.
We need to go
And by the way, this could be someone who's like, We need to go this way or that way. Like I don't know exactly what you know, this is a abstract example.
But if you said, hey, okay, cool, what's the best book that you've read on healthcare in America and like why it's gone to the way it is and and what the right answer is?
I a lot of them will say I haven't read a book.
I write a book about it.
I've read a lot of tweets. I've read a ton of tweets. I've read a lot I've listened to a lot of podcasts with politicians about this.
And celebrities about this.
I've read some, you know, Atlantic thought pieces or something like that. I have I've subscribed to a few subsecs.
But to like have you deeply like gone into the subject.
And the the the filter that I use is if you remove the social incentive.
So much of this you've done because of the social incentive. It's to comment. It's to go to work and talk about something.
It's
You know, the reason I think people don't often read a lot of these old books is because like that social incentive goes away. You know, you read this book.
And then
You're smarter. But
That's it. But I can't signal that easily to other people.
Yeah, I can't yeah, exactly. Yeah, it's like oh man, like I read this phenomenal book on like I'm reading a book right now on whales.
Um
I don't know why. Like someone I like.
tweeted about the book and it seemed interesting and it's quite it's interesting. It's a very interesting book.
I don't know why I'm reading it. I
Haven't talked to anyone about it.
It's full of really fascinating stuff.
But like very, very few people I think do that, you know? And but but ironically almost almost in this sort of paradox.
When you do stuff like that.
Short term I think that's true, but long term
Over time I really think
That's uh clear I'm doing it. Like I th there is still a reason I'm doing it. Just like
a much larger, longer time horizon. And I this has happened so many times, or I'll randomly run into somebody.
Someone who maybe is exactly the perfect person to like propel me in my career.
And
They'll be like, What you know, what book are you ready? And I'll be like, Oh, I'm reading like
A face like glass, it's like young adult fantasy thing or whatever.
And they'll be like, that is my favorite book.
That is my that that has happened to me so many times. And guess what?
I'm now their the the they want to hang out with me all day long.
Not to talk about this other stuff, but just to talk about you know, like they finally have someone else that they can talk of. So I do think it's it's it's sort of that sort of impatient with, you know, impatient patients, uh
you know, kind of a sort of thing. Impatient you want to be impatient with results, I guess.
But I I definitely notice that in people. Like there it's very rare to to meet someone who's genuinely just like exploring things that are at the sort of limits of their interest to kind of figure out what's new and different. And it's selfish of me. I like those people because they can teach me about all this new weird stuff.
that I can go explore myself.
But I find that sort of innate curiosity that isn't tied to a social thing or a
financial thing is
is r is relatively rare. And maybe that's just quote unquote privilege, right? Where it's like, Oh, you've achieved X Y Z thing is sort of the philosopher king thing. Like now that you're here, you can spend all this time
Messing around.
Uh and figuring out.
These things. Um
But regardless, I mean that is something that I I look for.
in the in the people that I hang out with.
That's interesting. I want to dive a little bit into that. What's your ideal ratio of sort of exploring broadly to diving deep into a certain subject, do you think for reading?
I I I would say I spend almost all of my time exploring broadly. Like I go deep
Very, very, very rarely.
Um
Even with authors, like it's pretty rare where I find an author where I I'm like, This person is so good, I need to read everything that they've written. That's happened a couple times.
Like Matt Ridley recently was one of those people for me. But even like when you read his books, it's like every book is
different. One's about genomics, one's about
Risk one's about
Virtue one's about
evolution, one's about innovation now. Um and
Th there's clearly a a a thread, right? Like you can kinda see the rational opt you can see like what's
what's w where he's coming from and certain his sort of fingerprint is certainly on those books.
But even he is it seems to me is just exploring these things broadly.
Because I think like
It makes those connections when they happen like just so much more satisfying.
When you find a connection between
I don't know, the way that
Mole rats like resemble
Like the way humans used to be.
And and maybe like there sort of we figured out that there's this sort of like middle ground of social you know, there's like packs, there's pack pack animals, and then there's like
you social animals, the collie animals that are like bees, ants, and mole rats, for some reason.
Mul rats are also part of this group.
And then there's humans. You know, it's just interesting. I just think it's like, oh, maybe maybe there's a way to apply like this is like a startup and this is a mid sized company, this is a large company. I don't know.
But I think
So it for me, so many of the insights, like the easy insights, have already been solved. If I just go deep, it's gonna take like literally you have to go to the bottom of the ocean.
to get like if you go deep in quantum theory.
There's a lot of books you're gonna have to read to get to really the frontier.
But if you go broad, I feel like
I feel like there's just so much more avenue there.
Like there's just so much more freedom.
Like it doesn't take that far to to end up in like totally unknown territory.
Uh it's it it's and and even if it i if there are other people there, there's like four of you.
You know, there's like four people on Twitter that are talking about
like the the commonality between like
Yeah, like animal relationships and like
company organization dynamics. It it's yeah. So I I always think that like that's a better that's a better approach.
I frankly very rarely go deep on on reading, at least.
What are some of the books that have had the biggest influence on you in terms of your thinking around entrepreneurship or investing?
How to win friends is my f my sort of top
w recommended book. It's almost you know
kind of a cliche, I feel like, at this point to recommend that book, but it is like the canonical example for me of this saving other people time. Like that whole book is about like how do I
operate in a way that makes everyone else's life just really clean, really stress free, really easy.
And so then everyone's gonna wanna work with you and and be your friend.
And and so I think that is a really great book, Thinking Fast and Slow.
Is a is a really great one.
Um, all of the Matt Ridley books I think are really, really, really good. I think understanding
uh your mental prison almost like understanding the constraints of your brain physically and your body f like just where you came from, like what led to this moment, I think is just so helpful.
um in terms of like feeling like oh these are the things you have control over, these are the things you don't have control over. Um
David, uh
Deutsch's books I just read The Big Beginning of Infinity and The Fabric of Reality.
Those books.
It's actually currently the thing that I'm thinking the most about.
Is is the fabric of reality.
Um
It's it's it like
I you know, I I don't know, you learn about, you know, parallel universes and and sort of quantum mechanics and things in high school, you take a you know, an elective or or what have you.
And you kind of get it.
intellectually, but like really spending hundreds of words like
or hundreds of pages like in this person's head and the way they think about it.
and how that relates to like free will and like just like really been interesting for me'cause that's one
You know, one one question I always I I think about a lot is like when you decide to do something, like you know, like when I decided to leave San Francisco and move to Provo.
Was it the stuff in Provo that made me open minded? Was I open minded when I decided to move? Like where did I have the learning? Where is that? Like is it a discrete system? Is there a point? Is it you know
And so I've just been thinking a lot about like
You know, like when I have an idea, when I decide to respond to a question you have, where is that even coming from? Like I just speak. I don't I can't tell you like where, you know.
It's very weird. And so I've been like really interested in like in the sort of parallel universes and
and quantum mechanics to'cause I really think like
When you when you learn the answer
Like there there is an answer. Like one you gotta believe that, I think, uh to keep to keep pursuing this kind of stuff.
But when you figure it out, like when you realize like oh the reason
that, you know, like I don't know, like a hot water cleans stuff faster than cold water. Like when you know the physical reason behind that.
It feels good. It feels like you have a grip on
the your life, you know, like it you can actually apply it in a way in a way, you know.
Wait, why why does hot water clean stuff faster than cold water?
So I think it's because you know
Temperature and heat is just the particles are moving faster. There's just more
things moving around bouncing stuff. So I think when you're cleaning stuff, like you just like have more particles like hitting stuff off that, you know, ends up dislodging
Peace.
molecules or or what have you from the
From the material. And so I think it's literally just like
clo the collisions are happening at a faster rate.
I think. But you know, just like things like that where you're just like I don't know, it g it fe it feels very satisfying for me to know.
Uh life is weird. I mean like life is very strange.
Um and I think you go through this middle where you you you you're born and you're like the world is flat and like the skies no above us and the you know and gravity it just makes sense you can like
obviously flying would be weird, like what you know, like
You just kind of take these and then you learn
All of this weird stuff, like we're on a ball of fire.
Just like shooting through
Like the void.
Like right now we're like what?
Um
You know, just crazy. Uh
And uh luckily we have like some rock around the ball of fire. The sun doesn't even have that. You know, just like just weird stuff. And then
And then I you I feel like just I'm just like floating, like I have no grounding in reality. I'm just like learning all these things. My life is like what is death and this and like it's just crazy.
And then it you know it.
once it once you start to read that stuff, I feel like I'm going back to that first place where it's all actually incredibly simple.
It's just a bunch of dots moving around and you know, bouncing off each other and at you know, different levels of extraction, you can use the phenomenon to explain different things.
Just like the earth and the sun, they're just two particles in space, just like
When you're cleaning something.
Yeah, it's just two particles in space or whatever. And then atoms, you know, there's like it kinda goes all the way up and down.
It's like a fractal pattern.
It just m makes me feel like I understand and I can like move forward without like
walking through a wall accidentally or something. You know, like it just
something like that. I don't I don't know where I'm going with this, but I I I I do enjoy like really feeling like I understand. And that goes back to the entrepreneurship stuff too, like just figuring out like what I can
What I can deeply understand, like reading the PayPal wars, reading in the Plex.
a lot of these books are just really important because you you are building a company, you're hiring folks
It's like why start from scratch, right? When you have all of these resources from people who've done it before and
And and the lessons aren't that like it the world hasn't changed that much in many ways. You can sort of like straight up apply.
a lot of this stuff and copy paste it.
There's a lot of timeless lessons from that. As you were you were talking, I was saying oh I was thinking that maybe you can just appreciate the beauty of the the world in a different level.
uh with with y that sort of understanding. And I think that that's really important to be able to do in terms of
Um quality of life, maybe. I want to come to happiness later, but switching gears a little bit here, what are you most insecure about?
I I am definitely insecure about like w wanting stuff.
I mean I I still think I am driven by
a level of of ambition and want.
for something. Even though I have read all of these books and I feel like relatively
good about what I understand about the world and how little it really matters. Like it there is something satisfying about it and
And so I'm definitely kind of like insecure.
About the fact that I
have those wants and desires. Like I think I don't know if they will go away. But I'm you know, I always try to
try to figure that out and unearth like why similar why like why am I like this? I don't have to solve the problem, but just understanding
Where this comes from.
it just gives me a l a level of sort of like closure almost of like okay, that's just the way I am. That's because of this thing.
I can't change it.
I can't get taller. I can't do that.
Right. Like there's just certain things and that's that's that's fine.
So that's that's that's a that's probably a a big one.
And then just like figuring out
I'm I'm sort of insecure with
how much I work, like how m I I I work a lot, um, I enjoy it a lot.
I I'm insecure about the fact that I enjoy it so much, even, you know, like I go on Twitter and I talk about maybe not working so much, but I just genuinely really enjoy
Enjoy it.
And so yeah, there's a lot there's a lot of things like wanting a nice house or whatever too, right? Like the basic things that people
people seem to seem to want um
And then you know, starting a family. Like that's the
That's a scary prospect as well that I
I hope to make like the focus of my life in the next like ten years or so. Why is it scary?
It just feels like it it feels like I'm I've been so self centered my whole life.
You know, it's it's basically everything I've done was for me.
And
you know, I got married in last year in December and that was like the first time that I you know, I was like, Okay, this is like we're signing up for it.
You know, something
Pretty big.
the the the the ideal relationships that I like with most people.
Uh for me, um
Just email me every six months. We'll check in. See how the marriage is going.
And uh
You know, like
I moved up to uh
Portland, Oregon recently. That's the first time I'd ever move to a place
As a group decision. It wasn't just me just saying, Hey, I'm gonna go do this, you know?
uh'cause I want to. And so that was like that's a there's a set of learnings that I need to go through, I think having children. Like I think that will be really meaningful and
But yeah, I think it's just like important for me to figure out like how do I live a life that sort of like the vision
uh of what's important is is is slightly larger.
Children are amazing, man. Um
Yeah.
Just so incredible. I'm excited. I'm s people ask me like what are you excited about? Like Gumroad and I'm always like having kids, like honestly, like
Five years from now or so, like
That that's definitely like what I
I'm aiming aiming for and I think everything else is sort of like
A kind of a distraction almost, like just to keep me busy until I get there.
Well, talk a little bit about your writing process. You're pretty prolific on Twitter. That changed about, I don't know, eighteen months ago or something. It just your style sort of changed a lot and ever since then.
Um, you know, uh I think you've got a lot of traction on there. So I wanna
I wanna learn about your w writing process a little bit, how you come up with ideas, how you
put them into pithy, uh sort of like
Tweets and
Talk to me about that.
I have a lot of conversations. I would say my life is sort of pretty distinct in two distinct buckets. I'm either like having an interesting conversation with someone or I'm
spending time totally alone, especially with COVID. There's no kind of like in between or social events or other background noise. Like it's really just like
We're talking or we're not talking like sort of feels like that.
So a lot of a lot of the tweets like
I s when I started learning how to how to oil paint, I realized like the fundamental skill in painting was observation. It wasn't like paint application and like knowing color theory. It was like can you even see
What's in front of you well.
And if you can do that, then like copy pasting that onto a piece of paper with some dirt and oil is actually the easy part.
Uh and I I I think the same thing with with writing. It's
It's like
living a life, like having a conversation with someone
It's almost meditative.
you're like having the conversation, but you're also listening to yourself have the conversation. And I think that's really important because you're you're sort of like your own editor where you you you can't change what you're doing and saying in the moment, but like maybe you can note it for like f the future use and that's how you improve as a communicator and
a conversationalist and I think writing is kind of similar where like I'm I'll be having a conversation with someone
And I'll
somehow like subconsciously sort of pin that little moment, like bookmark it of like I I said a sentence.
Within a rant about a certain topic.
That's
I should tweet. I should just literally take that

And go tweet it.
Uh and and that's a lot of my tweets. Um and then a lot of them are, you know, those sentences that I save and then I just like stare at for a long time.
Or there there are things that I just can't stop thinking about. They're I often feel like
It's like food poisoning or something.
Where it's just like in my system and I can't get it out and I can't stop thinking about it.
Every day I wake up and I like for some reason the stupid it's like a song stuck in your head. It just comes up again.
And I found one of the best ways to res it's it's it's like resolving a, you know, a problem in in therapy or something like that. Like once you figure out
Like what it is, why it is, you package it up in a way that gives you clarity. It's kind of like untying
you know, a certain like a string with a bunch of knots in it. You finally can see this thing for what it is.
And then I would I often share it. And the sharing is is really
cathartic for me because it sort of gives it to somebody else. It's like that's your food poisoning now. Like you go, you go, you go think about this for a while. I'm done. I did the work.
uh for myself. I you know, I've digested this thing.
Here you go. Have fun with it.
And that's a lot of how I kind of
how I sort of like to think. And I would say the other insight that I think has really worked for me.
is I always try to figure out like, does this apply to a lot of the things in my life? Like
I think if you take a if you take it from a very sort of entrepreneur business focus
you're gonna end up with like a very kind of narrow
Set of thoughts.
But if you if it I often will and and that's
a lot of the conversations that I'm having, but also a as a writer, as a painter, as an investor, as a
husband is other things that I
Do now.
If I can s take the same lesson and apply it to all to the other things.
And it sort of feels like a universal truth.
then I often like like those are those that's sort of sort of a filter that I use to like vet the quality of of something that I
That I would share.
As well.
One of the things that you said there that struck me was observing and
Talk to me a little bit about how we can become a better observer of the present.
Yeah, I mean I think a lot of it is is is paying attention and taking notes.
Uh this was the
One of the first times I had this experience was I was painting a rock. I was in southern Utah with like an oil on canvas and I was painting a rock.
And I spent three hours. It takes me roughly like two to three hours to like plain air.
Paint something.
And
I remember like
Sure.
Month.
I couldn't
Me, probably even today, I could draw.
I could draw that rock out for you. Like the the angles and the shape and the proportions.
you know, roughly um
If if I asked you to draw a dollar bill, like you wouldn't
I wouldn't be able to do it, you wouldn't be able to do it. We've never spent that time like genuinely staring and paying attention.
to a dollar bill.
I know what you would draw. I know what I would draw. R we draw this rough thing with like
A one here and a one here and like
A circle on this side. Something.
But we we have we had the silhouette almost, like the we have the shape and the yeah.
Yeah, it's like when you have when you're a kid and you draw the sun and you have the rays, right? Like
There's a symbol that you're storing. You have the almond eyes, you have
You know, like the nose that's like three big kind of three semicircles.
Um
But you've never actually like studied.
What this thing actually is and looks like.
And so I think
A lot of it is just doing that.
I think
you can improve like the the time that you're taking and that's what being present is to me is like just really
Focusing on the present moment and like noticing as many things as possible, which sounds easy, right? And it it it's almost paradoxical. Like you're obviously here.
Like what does that mean? You're obviously looking out through your eyes, you're smelling things through your nose.
But like
If I said, okay, when like how many times did you blink in the last three seconds, you wouldn't even remember the last time you blinked.
Clearly you blinked. Somewhere in the last like your eyes aren't drying out, right?
But like
It this is something that you literally saw.
Like you saw yourself do that.
But it's gone. Like your brain didn't even remember any of that stuff.
Um and so I think that's a big part of it is your brain, unless you you tell the brain you signal to it.
Hey.
This is important. Like make a note of this because I'm gonna need this later.
Mm.
To survive.
Or or you know, to d like some of these very fundamental biological uh
Incentives.
It's gonna forget because guess what? Like you have a finite number of neurons, you have
energy and you know, it to energy is being expended. Like, you know, there's the sort of the the famous adage of the sort of like the chess players that burn like eight, nine thousand calories a day are like doing this insanely intense
Exercise effectively. Um so I think that's a big part of it is like you need to figure out like what is the uncomfortable
What is like the the exercise version of what I'm doing?
Right. Where I'm not just
Yeah, like
I don't know, drawing dragons out of my head, but I'm actually like figuring out like okay what are
what are the fundamental building blocks that lead to me being able to do a certain skill and then
And then, you know, kind of a tree structure and then figuring out, okay, that means I need to learn perspective.
That means I need a draw.
hundreds of boxes in in perspective.
Once I can do that, then I can draw.
Ants,'cause ants are a little bit more structural or something like that. Then I can draw maybe like looser looser animals like uh you know, things with fur and
and and things like that. And then I can I can do cars and blah blah blah. Like are you gonna scale that up? And then you like a a dragon is sort of like a cat with wings that breathes fire. Like it has the the body proportions roughly of a cat.
And that's where the dragon dragon like comes from.
But the f like some people I think they just look at they they don't do the work of figuring out like what is the path that leads to this.
They just
say, Oh, that I I wanna do that. Right. So it's kinda the same thing. It's like the way you you have to learn
what you need in the moment. And you can't really it's like, you know, you gotta learn addition to learn math, uh to learn multiplication, you gotta learn multiplication, to learn division, you gotta learn both of those things to learn.
Algebra, you gotta learn algebra to learn.
Geometry, I think, you need those things to learn trigonometry, you need those things to learn pre calculus, like et cetera, et cetera, et cetera.
Um
And if you miss one of those things.
You you can still get by in life, right? Like you can still like ace the tests and
And draw the things when you need to, you can memorize, but you don't really have a a deep understanding of that. And it's kind of the same thing with with being present. It's just like
I think p some people go really far.
And they just
they feel like they need to do all of these things, but the truth is you just need to be there.
And you need to stop thinking about other stuff.
And you just need to like really
Like it has to hurt.
Almost like yeah, you have to be so focused, like you're working out. Like th I'm spending an hour
Trying to figure this problem out.
Um, and I think most people they they they might think about it like, Oh, I just need to
meditate. But I meditation is is almost work. Like it it it I think it is it is like a you know like exercise physical physical activity.
This has been awesome, man. I really appreciate you taking the time to talk today.
You're welcome. Thanks so much for having me.
Mm.
Hey, one more thing before we say goodbye.
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