What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
More people than ever are building cool stuff online and making a lot of money in the process.
And on this show, I sit down with these IndieHackers to discuss the ideas, the opportunities, and
the strategies they're taking advantage of, so the rest of us can do the same.
All right, I'm here with Sean Purry and Sam Parr, two of my favorite podcast hosts.
You guys host the excellent show, My First Million.
Welcome to the IndieHackers podcast.
All right, let me ask you a question.
What was the valuation of Stripe when you sold to them?
I think it was like $9 billion in April 2017.
Three-part question that results in Sam knowing your current bank balance.
That was part one.
Okay, I'm not going to answer the third question.
I know what the third question is.
I'm not going to answer it.
What's the valuation now?
90?
It's $95 billion now, I think.
Damn, dude.
And by the way, it wasn't even risky back then.
Did it feel risky when you...
No, no, no, no.
It didn't feel risky at all at the time, because Stripe was obviously a good company already.
But also, that wasn't even on my mind.
I wasn't thinking, what's the valuation of Stripe?
I was more just thinking, hey, I'm running this really tiny, scrappy website.
How do I make enough money to pay my rent?
And so I was just trying to get sponsors.
And I had this giant list of the perfect sponsors for IndieHackers, and Stripe was number one
on that list.
And after I built up enough sales skills, I was going to reach out to them.
But before I got to that point, Patrick, the CEO, emailed me and was like, hey, can we
buy IndieHackers?
And so I was like, yeah, of course.
Yeah.
It's much better than getting a sponsor.
Sean, do you know Cortland has a brother?
Yeah.
I found this out the other day, that you have a twin brother.
Yeah.
But they don't look identical.
Yeah, they look similar.
But he came to Austin like a month ago or three weeks ago, and he came over on like
a Tuesday or a Wednesday, and we had a good time.
And then he ended up coming over on Friday, and we ate dinner.
And he was like, you guys want to go out?
And I'm like, no, I don't really go out, but Sarah, my wife was like, yeah, I'll go
out with you.
And they went out until like 3 or 4 a.m. party.
I can't even get my brother to go out with me.
I'm like, hey, dude, come visit me in Seattle.
And he's like, nah, I got better things to do.
Like I just saw him last week for the very first time since the pandemic started.
Oh my gosh.
But yeah, he's like my right hand man at IndieHackers, kind of in the same way that you two worked
together on your show, My First Million.
Why don't you tell listeners what your show is about in case they haven't heard it yet?
It's basically two dudes who started startups and have been doing it for like 10 years,
just getting together and shooting the shit about what other startups either are cool
that we've seen or we think would be cool if somebody started.
And so it's kind of it's basically a brainstorm.
And what happens is if you listen to it, you know, most people who listen to it, they,
you know, they get entertainment because it's kind of fun and it's off the cuff.
And it's, you know, me and Sam go back and forth a little bit.
But the big thing is it gets the wheels turning like once you start listening to this, you'll
just start seeing business ideas and opportunities all over the place, almost to an extent that's
kind of annoying.
It's a switch.
You can't turn off.
And that's how we're wired.
That's how we are.
And so we are kind of infecting other people with the same disease.
And a lot of people think that like we're just showing up.
And in some like in some regards, it's true and that we can totally go off the cuff.
But we also research way more than people probably think.
So throughout the week, we'll see stuff and like, I don't actually know how Sean does
it.
I think, well, he probably does the same thing, but I'll like get on the phone with someone
and I'll say, tell me everything.
And I'm like taking notes.
And I'm like, thanks.
So I mean, it's almost like, it's very like traditional journalism.
And I'm like, by the way, everything you say, I'm going to talk about.
So don't talk to me about anything you don't want everyone to know.
And it's pretty cool.
Well, I think the difference is a lot of people will be like, Oh, that makes sense.
You have the show.
So you do research for the show.
And the reality is that I think for the last 10 years, this is all we did in general.
We're just curious cats who like can't stop.
So in the same way that Sam's like, what was stripes valuation when you got acquired?
Okay, cool.
Then Sam will be like, you know, what is the tip of aqua higher worth?
And then he'll like, you know, you'll do all this research just for your own, you know,
shits and giggles.
And then that just gets stored in your memory bank somewhere.
So what happened was we just do that naturally as like a part of our daily work.
You know, like we're lucky that our work, our job kind of lets us just go down these
rabbit holes.
You see a business like today, I was going for a run and this, uh, this truck was driving
and it had like a, uh, like a piece of heavy machinery behind it called, and it was, they
said van mere and our good buddy's last name is van mere.
And so I was like, I was like, well, I'm just on this run where I'm supposed to be focused
on running.
And instead I'm like, I literally like pause for a second.
I had Google van mere.
I'm like, is this like his great grandfather?
What is this brand?
How do you do these tractor companies crush it?
How much does this van mere company make and like, what's their business model and like,
how long have they been around?
Are there any new companies doing this?
And so that's like a addiction that I have basically.
That's my process.
My process is constantly go around the world, observing things and then go down the rabbit
hole to figure out what's the backstory behind all that.
So I did that the other day that I've seen, have you ever seen these semi trucks and on
the back they have what looks like a tail.
It's like a, it's like a two foot, how do I describe it?
Imagine the back of a truck and it has these like wings, but they kind of curve in.
So it's like the end of a cube.
I'm not explaining it well, but the end of a cube, but it's got these wings that point
in.
So I saw one on these trucks the other day and I was like, what the hell is this?
And I looked this service up.
It's like a spoiler for a truck.
It's like a spoiler for a truck, but it doesn't look like a traditional spoiler, but yeah,
that's exactly what it is.
And I looked it up and I'm like, what the hell is this thing?
And there was a company based out of Redwood City making these and I just saw them on the
road.
And I promised that it's going to make you like 0.5% more efficient and it's only like
$500 or whatever it is.
And so I did the exact same thing.
I saw this on this truck.
I'm like, I gotta go know what this is.
And the company sold for $200 million, like not that long ATD dynamics, I believe is
what it was called.
And so anyway, this is like, yeah, we do the exact same shit.
Well, it's addictive to listen to you because even on my show, I'll do like a brainstorming
episode every now and then.
If I just call an episode business ideas for 2021, it gets like twice as many downloads
as every other episode.
Cause people are like, hell yeah, I want some free business ideas, but then I worry that
people who are like addicted to these types of shows aren't actually building stuff or
doing anything.
Cause you just want to hear more and more ideas rather than actually like start working
on something.
I call that getting addicted to the medicine where, uh, you take the medicine, it's supposed
to cure the problem and shows to like be able to move on with your life.
And some people just love drinking Robitessum every day at some point, right?
You don't want to get stuck in that pattern where you just want to keep getting more and
more advice, more and more ideas.
It's like, well, yeah, if it's for entertainment, which I think is what most people do, they
did get it for, they do use it for entertainment, not they want to have friends in their life
that want to geek out about business the way they do.
And we are like their friends who like to nerd out about business even more than they
do.
And I also think that like, we do have a lot of like legit ballers who are listeners.
I mean, if you said you're a listener, so there's not that many people that ever take
action on anything, but I do think we've got a really good ratio of that.
I think in the future, I think actually we should consider almost, I'm incredibly fascinated
with the idea of going daily.
We haven't discussed it yet, but it's like something I think about and like, because
I find myself listening to like Brennan Schaub and all these other podcasts, and I love them
because they talk about current events and they give their opinion on it.
And I think there's a world where we could kind of do that.
And the reason I'm saying that is we kind of already do.
So like when something happens, like the other day when Bitcoin like dropped, Sean did a
thing right away on a Sunday morning, and it was a huge hit.
And so like we definitely we don't do like a traditional maybe podcast like a lot of
people in our industry do where they're doing like interviews or something that's a little
bit more evergreen.
And we do evergreen stuff, but we definitely can react really quickly to things with our
angle.
And that's kind of intriguing.
Yeah, I think evergreen content is overrated.
I mean, it's kind of a cliche that that's the type of content you should be putting
your time into.
But if you're trying to do something that's entertaining, and you want people to come
back every single day, like nobody's really creative enough to make evergreen content
every single day.
But if you're just giving your opinions on the news, like shit happens, and people want
to know about it, and they like your personality, then you can just get on the air and just
be authentic or just write authentically with your voice.
And you can rack up like millions of listeners or subscribers.
In fact, this is how most of the big media companies online operate.
Sam, your newsletter, The Hustle, has a couple million subscribers just giving your opinions
and takes on the news.
Well, it started, I don't know if you know how it started, but it started off, when he
was at the beginning, it was more like evergreen hits, long form, super interesting blogs,
like kind of like going for home runs.
We're going to talk about a topic nobody's talking about in a way that nobody's talking
about it.
It's going to be amazingly manufactured.
And then we're going to distribute that and try to get that one blog post to like millions
of visits.
And it was working, but it was also like, dude, is this the treadmill I want to be on?
Or what if we just went lightweight daily, react to the news, summarize and react to
the news, give people what they need to know in five minutes and like not try to be a kind
of like genius original content creator every week as my summary at least, Sam, I don't
know if that's accurate.
That's very accurate.
It was hard.
I mean, I could do it probably, but it's a hard ass life and it's really hard to hire
for.
There's a reason why Casey Neistat did what he did for a year and then quit.
He was like, Oh my God, this is exhausting.
It's challenging.
Yeah, it's just too hard.
Like if your, if your goal is to produce content and your strategy is that you're going to
come up with new, interesting ideas for every video or every podcast and like that idea
is dead on arrival.
I think you got to index on some other source of novelty, whether it's the news or on this
show, like I don't ever come up with new business ideas.
You know, I just have people on who have their own business ideas and like that is an endless
process.
Like I'm never going to run out of people to interview who have cool and interesting
new business ideas.
And so that's just a much better way to go about it.
And I think you guys on your show, My First Million, you have, um, I don't know, you kind
of the same thing.
You're talking about other business ideas that others have come up with and you also
just got bought by HubSpot.
So I'd assume, uh, at least you, Sam, probably have some sort of financial incentive to keep
working on the show and making it.
No, I mean, so we, the podcast is his job.
Yeah.
The podcast is my job.
So when we, like we were going to sell, um, like they start reaching out to us and during
that time I had basically already made an offer to someone to be the CEO so I could
do a podcast stuff and they wanted to buy us and I go, okay, well I'm going to have
to rescind my offer to this guy because I was promising him that he's going to run it
independently and that's no longer going to be true.
So I did that with him and I go, but then you also have to promote someone from within
or hire someone to be like the boss because I'm not going to be the boss.
I would love to be here and continue doing and do content because I love it, but I'm
not going to be the CEO.
So I, and also there's no, we don't have an earn out.
Like there's no, there's like milestones that we want to hit, but like, I don't have like
money on the line in order to hit that milestone.
And so, um, it's a little bit different.
Like when you're saying like I'm in the trenches, I am, but like, if I, I would do it anyway.
I would say, I would say it's more like, uh, there's a period when you get acquired where
you're like, all right, give me the Kool-Aid past the Kool-Aid.
Like I'll drink it.
You know, like I think from, I think for a lot of people, I was this way at least I'll
just speak for myself.
There's a period where you're like, ah, they give me the swag.
And then I show up.
Well, at least when you're in person, it's a lot easier than when you're remote, but
like, it's very easy to just get swept up.
It's like, oh, I'm going to add you to this meeting and oh, we'd love to pick your brain
about X.
And you know, you start getting pulled into all these strategy things because you're the
stress smart, new, like high energy strategy guy who's not like scarred and jaded by all
past failures.
And so, you know, you, you start getting pulled into all these things and you're able to contribute
and you meet all these people and you're, you're at the cafeteria and you're like, God,
my life is no stress now because I sold my startup, like there's a period where you're
like all about it.
And then what I've seen, I'll just speak for myself.
There's a transition period where you're like, okay, like working super hard here really
doesn't really get me any more or less than, uh, if I just do what I enjoy and I work a
like a certain amount of freedom and lack of oversight.
I think you're talking about this a little bit earlier.
I did this at Twitch, which is the first year I tried to kill it.
I, uh, I did everything I could.
I wasn't like working a hundred hours a week, but the hours I was working, I was like, I'm
going to do the most high impact thing I could do for this company at all times.
And I'm going to be me on blast and I was doing it.
And then, then like a year in, I was like, well, I'm leading this team and at a big company,
it's really like you're doing all the jobs of a startup CEO without the upside.
It's like hire and fire people, set the strategy, dictate the roadmap, manage a whole, you know,
like 30 people or whatever pitch for funding basically.
And your funding is just head count, uh, and resources.
So it's like all the jobs of a CEO without the like actual freedom and actual upside
of a startup.
And so I went to the CEO and I was like, Hey, like, you know, I just hit my one year.
I'm thinking about what's next.
You know, it's smart to either like sign up now for another full year or like bounce if
I want to bounce.
And so I said, you don't have a lot of fun here, but like, if I'm going to do all this
work for a startup, I should just go start my own startup.
I should own all my upside.
Uh, you understand he's, he's a founder, so you understood.
And he said, uh, and I said, but you know, there could be a model here that works, um,
like here's what, here's what I would like.
And I, and so I like sort of laid out a role that I thought would be fun for me.
And it was basically like, you know, something I'm interested in with no direct reports with
no, like, kind of like, it's not like a mission critical project like the one I was doing
before.
So it's like more of a creativity fund, freedom project.
And I was like, you know, I'm going to work this hard and I still think I'll make an impact,
but I'm going to work like roughly this hard and I got all these other things I do.
The podcast is growing.
So like, if y'all are cool with all that, then I'd love to stay on.
And they gave it to me.
And I guess like, I've seen that that's a pretty typical path of a founder.
You go from like, I want to crush it, justify it, learn everything from this, learn everything
I can from this company and like prove myself.
Then you're like, okay, don't need to like prove myself so much anymore.
Prove myself, learned, learned a bunch of stuff.
It's kind of repetitive.
Now let me transition to either out the door or chill mode.
You know, where you're, you're cruising, doing what, just the part you enjoy with none of
the stuff you don't enjoy.
And then, and then it's like gets the, gets the itch to go do the thing again.
That's the pattern.
And they know that the buyers know that.
And they know that.
Yeah.
At first I was so afraid to be like, Hey, but I love, I really love these people and I connected
with them.
So I was like, Hey, I'm going to level with you.
And I was waiting for them to flinch and they're like, dude, we've seen this rodeo like a hundred
times.
Like we get it.
I know who you are.
I knew that when I got you, like, you know, when we bought the company and like, look,
I want you to be here forever, but if like literally Emmett, the CEO messes me one day,
he just goes, look, I know you're going to want to go start a company someday.
I wish we could keep you forever.
I know that's not going to be the case.
When you do your next thing, I'll be your first check-in.
And so that was like a totally different mindset than this.
Like what I thought would be, no, like what you're saying is bad and evil and how dare
you.
But there's like, you know, the people pleaser in me was still like a little bit hesitant.
Exactly.
Just be fully honest.
But when I did, I was like, Oh great.
This is no problem.
They understand.
Yeah.
And it's a big show.
Like, I think I'm the star.
And they're like, dude, there's thousands of people at this company and next year they'll
be in much.
Yeah.
There'll be a new you.
We've seen this turnover five times.
And there's also this middle ground, which is like you, it doesn't, who cares what the
paperwork says?
Like there's a handshake agreement that says you got your ethically say, I'm going to provide
value to you.
You're going to provide value to me.
Me personally, I'm still more important.
Like I'm more important to myself than that company is.
So I'm not going to like die to help you, but like we have a handshake agreement.
I'm going to give you value.
I'm also going to extract value.
And hopefully it's a 51 49 like when you get more value, but that's what we're going to
do.
Well, there's this path that I see a lot of people taking right now that Sean, you kind
of seem to be on and it's kind of like this individual, successful investor rich tech
guy path.
And it seemingly goes like this.
You build an audience for yourself.
You've got a podcast or you're on clubhouse or you're on Twitter all the time.
You just sort of put out your wisdom and your knowledge into the universe and the people
who like you glom on to you and the people who don't, don't follow you.
And you keep doing that day after day, week after week, like you treat that like a full
time job and you build an audience and you start to get to know a lot of people.
And through that you start getting access to investment opportunities.
So overall you're converting social capital into financial capital.
The social capital is all the trust that you're building with your audience day after day.
It's going to show enough and proven to people that you actually are who you say you are
and you know what you're talking about and then people come to you with deals and you
can invest much earlier than the average person gets a look.
So for example, someone who's doing this really well is Sawhill from Gumroad.
He started Gumroad.
Gumroad's huge and that doesn't necessarily mean he's super liquid, right?
Like the company's worth a lot, but like he hasn't sold it or exited.
So where is he going to make money?
Well, it turns out people really like Sawhill.
They like what he has to say.
And so he's constantly going on every podcast.
He's tweeting like it's his job.
He was early to clubhouse.
He's got a huge following on clubhouse and then he also set up a rolling fund.
And I don't know how often would be once every week, once every few days, somebody just puts
like 20, $25,000 and he was rolling fund for him to invest.
And now I think he has like $13 million that he's investing on behalf of other people and
he gets to keep a percentage of the profits and also a percentage of the money in total.
And that's pretty lucrative if you have a big audience.
So Sean, it kind of seems to me like you're going down the same path.
Yeah.
I think it's, I actually think it's fairly, it's, it's fairly paved this path, but I think
that it's like a path that's been paved, but then all of a sudden they built all these
new roadside things.
It's like, Oh, that restaurant wasn't here before.
Oh, there's a gas station.
Wow.
Now we can go way further.
Right.
That's what I see.
So, so I grew up and like, I, there's a couple of major influences on me when I was kind
of like making a shift into business.
And the first was Tim Ferriss, so somebody somehow, somehow, somehow, somehow, someway
I got my hands on for our work week and I had what you call the four hour fever, which
is when you finished the book for the next four hours, you're like, fuck everything in
my life.
I'm changing everything.
I'm like, I'm doing all these things.
Why don't I have passive income?
Why am I working so hard?
Why don't I have a virtual assistant?
Why don't I travel?
I, why don't I, you know, get fit?
Like you want to change all these things because he makes it seem so desirable and so achievable.
Right.
So that was the first big influence on me.
And a guy like Tim Ferriss, you know, in, in many ways when, you know, the person who
sort of shows you the way you're like, well, I respect you, I like you, but also I kind
of want to be you.
It's all I saw.
Okay.
Here's a dude who basically took his own life experiences, distilled it down into some kind
of operating philosophy and then packaged it up for the world to consume through books
and a blog essentially.
And then later a podcast, later a newsletter, other things.
He translated his fame into access for deals.
We invested in Uber invested, I think in Twitter and a couple, couple other big ones.
And also had like a great kind of like friend group that emerged from that was always hanging
with interesting people.
That seemed super fun to me.
So I really liked this guy's lifestyle and I thought, I didn't really even like decide
at that time, but I always just thought, Oh, that's amazing.
But to me at the time it felt like if I wanted to pursue that, it felt like saying, you know,
I want to go be LeBron James or like, I want to go into Hollywood and you know, be George
Clooney.
It just felt like a, well, that's a lottery game.
Like there's not, I can't name 15 Tim Ferriss's at the time, at least I thought there's only
a few people like this.
There's probably not a good path to bet on.
So that was the first influence.
Second one was Tony Robbins, same sort of thing.
I was like, Oh wow, this guy's great.
I discovered his content helped me out a lot, changed the way I saw the world with his operating
philosophy.
And I was like, I went to one of his, his events and I was like, holy fuck, there's
10,000 people in this arena paying thousands of dollars to like, like just attend this
guy's show, this performance.
And I was like, I've never seen anybody like this.
Never seen a speaker captivate people like this.
How the fuck does this guy do it?
And I was pretty like enamored with that.
I was very like intoxicating to see.
And I thought, okay, I don't really want this lifestyle.
Like just like with Tim Ferriss, I didn't want to write books and cause that seems slow and
kind of boring.
Just like Tony Robbins, I didn't want to go on tour, but I wanted elements of what they
had, which was a cool set of life experiences, which help you with, which you then distill
until operating philosophy.
You share that you build a big trusted audience.
And then you turn that social capital into financial capital so that that funds you doing
you full time.
Your job, your company is you.
And so I just thought, oh, that's pretty fun.
Like I think a guy like Tim Ferriss, I think he basically wakes up.
I don't know him.
Sam actually knows him, but I'm at him once and it's, he seemed like a pretty curious
dude.
What it seemed like his life is, is he wakes up, he's curious about a thing.
Like it might be because he's having some pain point in his life.
Like I want to lose belly fat or like, I just got diagnosed with this like disorder and
this is the traditional medicine, but it doesn't seem to work so well.
What are the alternatives?
And then he just goes down that rabbit hole.
He learns about it from the best.
He self experiments.
And then he comes out the other side and he teaches that to everybody else.
And I thought, oh, that's dope.
This dude just gets to be like a curious student and gets paid millions of dollars for it.
That seems like way more fun than what I was doing than a normal job for sure.
But even more fun than being a startup CEO, picking a market, raising money from investors,
having a team that you got to go into the office every day and raw, raw, keep everybody
happy and keep everybody motivated, come up with your strategy.
So I, I basically just looked at it.
Once I sold my company, I was like, all right, am I going to stop bullshitting or what?
Like, am I going to try that path?
Even though the odds seem bad or, or, or am I just, should I just put away that, that
idea forever?
And so I just decided to lean into it.
The odds aren't that bad.
At the time it felt really hard and impossible.
Well, to be fairs, it's like you said, he was like one of the only ones doing that.
There wasn't like a very clear path to follow, uh, whereas now there's just so many different
issues to get into.
He might be number one in that kind of field, actually Tony Robbins and others are kind
of a little bit bigger than him, but then then you have him, but then you have like,
you know, a rung down, you'll have, I don't know, whoever pick your favorite James clear
or, um, you know, Ramit Sethi or whoever.
And then you have in every niche, you have a thought leader.
So you realize, okay, it's not an all or nothing game.
Like at the minimum, I can land in kind of like level three right now and feel some version
of success.
And then if I just keep going, maybe I'll get there.
And I'm pretty like, I don't know, cocky slash confident.
So I was like, okay, you know, why not me?
Right?
Like I met Tim.
I was like, there's nothing, there's nothing magical about this guy.
Uh, it seems like a normal person, just like me, who like, he just did him on blast for
10, 15 years.
I could do that.
That seems, that seems doable.
So that's how I described this path.
And it's not always about an investments.
Make sure Tim Ferriss made a lot of money from investing.
But talking about James Clear, I just spoke with him and Mark Manson the other week.
They were both prolific bloggers.
And James Clear, for example, he was able to grow his mailing list to like a million
subscribers just from blogging consistently and it being really good at SEO.
And then they both wrote books and they're just going to take their best blog posts that
they had proven worked the best.
And they turned them into like best selling books.
Yeah, exactly.
And Mark, I think Mark's book, if you read like, I went and read like an annual report
from Fox or news court, whoever owns like penguin books or something.
And they're like, what's his book called?
It's like called like, fuck it.
I don't care.
The subtle art of not giving a fuck.
It was like, they like positioned it as like the breakout hit that saved the company.
I mean, it was like a pretty big smashing success, right?
It's huge.
It's huge.
I mean, people severely underestimate how much money you can make from a really good
book.
If you have a huge audience, like most nonfiction books probably sell a thousand or a few thousand
copies if you're lucky.
But the subtle art of not giving a fuck is sold something like 14 million copies.
And Mark probably makes two or three dollars a copy.
No way.
So you're telling me you think he made over $30 million off that book.
I think he made at least $30 million.
No way.
I so don't believe that.
That's amazing.
Yeah.
Books would be ridiculously lucrative, but it's hard.
Like James Clear, again, he had a million email subscribers.
And in addition to doing all the work of writing a book and getting all those subscribers,
he also did like 400 podcast interviews before the release of atomic habits.
Like these are like the top books in their categories.
But I suspect that if you have a huge audience beforehand, you can kind of play publishers
off of each other.
Like I've had multiple publishers email me about doing a book for indie hackers.
And you can probably negotiate to get higher than the industry standard of like 15% royalties
on book sales.
Right.
I don't remember if it's Tim that told me this or if I read it about him.
But I think he said in order, revenue streams were something like...
The highest to lowest was investing, advertising, revenue, and then significantly below number
three was books.
Right.
And that doesn't shock me.
I mean, I think successful tech startups are a lot more lucrative than books.
And I think Tim was like early to Uber or something crazy.
And Shopify, dude.
Just those two alone.
That's a whole other level.
It could be in the 100 million plus range.
I mean, being early to $100 billion showed up is among the best investments that any
human has ever made ever.
But even that, that's what I have to say when there's new stuff built on the road.
One of the things that for me I used was this idea of a rolling fund.
Sam does SPVs and syndicates on AngelList.
So I'm pretty sure Tim was investing his own money.
Maybe there was some backend deal where like whatever Sequoia gave him money as a scout
or something.
But I think he was just investing his own money.
But for example, we're nowhere near Tim's size.
No, we're not even close.
And I tweeted out, hey, I want to raise a rolling fund.
If any people want to co-invest in deals with me, I've been investing and here's an option.
Here's a link, basically.
And that turned in for me with zero outreach, zero meetings, and zero reaching out to my
own personal network.
So these are all strangers from the internet who just follow the podcast or follow me on
Twitter.
And that became $4 million a year of investable income.
Just to put that into terms, that's not a huge number, right?
I think Sam will probably invest even more, maybe five times more this year off his syndicates.
And he did the same thing.
He just leveraged his own fame to raise money.
And so if you just do the math on that, right?
So let's say $4 million a year.
Standard carry is 20%.
I don't take any management fees, but I could take a 2% management fee.
So 2% management fee, that's $80K a year.
So that's pretty much a starting salary for- Yeah, that pays the bills.
That was my salary.
That was my salary when I started, yeah.
So that's the first part.
Then you take the carry.
So you're basically saying of every $4 million invested, it's the equivalent of me getting
to write about $800,000.
Let's just round up to a million, a million dollars a year of startup investments.
And the startup investments take, let's call it 10 years to mature for that fund to fully
pay out.
So that's basically $10 million of money that I get to invest that I didn't have to take
out of pocket.
So that's $10 million of equity value without counting in the appreciation of any of those
investments, right?
And a good fund might 3X in value.
And so a good fund, it could do better, but even just like normal solid returns over the
10 year period would be a triple.
And so that would mean that my 10 million in equity value, it becomes like 30 million
in equity value.
And this is for something that I put, I just snap my fingers and turned audience into cash,
but it's a win-win.
It's not like I'm charging them something, I'm giving them access into A, my brain of
knowing what startup investments are good and bad, but B, my deal flow of deals they
could never get access to in the private market.
So you get this win-win with your audience, but it's pretty massive value.
And that vehicle, that rolling fund, that didn't exist for Tim Ferriss, it didn't exist
for Tony Ramos.
They had to find a different way.
It's just, everything's easier now.
Just like Stripe made it easier to take payments, like it's easier now to raise money.
It's easier to create merch, it's easier to create a course, it's easier to do all the
different business model tactics that you can do.
Like Pomp, Pomp is another kind of like solo creator.
He's got like a job board.
And so he's big in Bitcoin, that's what he's known for, so he created pompscryptojobs.com
or something like that.
So he's making, I believe, he didn't confirm this, but just my own kind of sleuthing here,
he's making almost a million dollars a year off his job board, right?
So he was like a high level person at Snap, at Facebook, whatever.
He's basically replacing that with a passive income stream.
Again, just snap his finger, spin up a financial asset.
Stephen Ferris could have done that, but he didn't have these tools nor awareness to use
it.
They were following the traditional playbook, which was like write books, give speeches,
go get paid $30,000 to go talk at some company.
And the last one was like, he created a TV show, was like, go for mainstream media.
And now we have like way more tools in our tool belt that we can use to generate much
more income.
Right.
And despite all these tools that help you make money, I still don't think it's like necessarily
the most accessible path to start with, because you got to build an audience first.
And that's a doggy dog world.
Like a ton of people are out there hustling, trying to make a name for themselves.
And most of the people I know who've succeeded are kind of like the two of you, where you
have these previous business successes that lend you credence and help your audiences
like build trust with you.
Yeah.
But by the way, we didn't, we didn't have that audience either like 18 months ago.
And neither did Pop didn't have that audience two years ago, three years ago.
So it can be built fairly quickly, but you're right.
Not everybody wants to or can.
But this is not a thing where I'm like, anybody can do it.
It's or sorry, it's, it's, it's anybody can do it, but not everybody can do it.
So it is open to all, but it is not going to be achievable by all.
Okay.
So let's, let's get into some ideas.
Let's talk about ideas that like the average person can do or build.
You guys have your own sources of ideas.
Sam, you've got the hustle.
You've got a team of journalists who are literally working around the clock to find new interesting
business stories and ideas to bring to you.
For me, I've got any hackers.
I'll go to the Andy hackers product directory.
You know, yeah, I'll just sort by like recently updated and then I'll look at who's making
at least $10,000 a month in revenue and just see what pops up, like see what cool ideas
people are working on.
You need like a growth rate one.
Yeah.
I should add that for sure.
I built this whole directory a few years ago and there's only like a hundred products on
it.
And I checked the other day.
Now there's like over 14,000 products where people will sort of share what they're doing
and how much money they're making and what they're working on and how they come up with
their idea and stuff.
So I should definitely add more features to it at this point because it's pretty cool.
But one of the trends I've been noticing is just people sort of deconstructing and making
like really small niche versions of big venture funded apps.
So a good one is like calm.com.
It's a big mindfulness and sort of meditation app and there's some others in the sector
that are making like tens of millions, hundreds of millions of dollars in revenue and they've
got like a ton of investment.
And then on any hackers, I've found people who are making like little small versions
of them.
So one of them is called mantra.
It was built by this guy a few years ago and you can look at his timeline and see like
exactly what a stock process was.
So he says he was lying in bed watching his girlfriend at the time use a daily affirmations
app and he figured he could build something better.
And so this is the very first app he's ever made.
And it's super simple.
Like I downloaded the app, you open it up and it's just got different categories for
affirmations.
So it's got like improve your sex life.
These affirmations will help create a more satisfying sexual experience in your life
and generate wealth.
These affirmations will help attract wealth abundance and prosperity to your life and
just stuff like that.
That's hilarious.
And then a few years later, 200,000 people have downloaded this app and he decided to
add subscriptions.
So he paid 20 bucks a year to get access to themes and music and whatever.
And I think he made $3,500 in his very first month.
He's got 10,000 reviews and the average rating is 4.8.
Yeah, he's doing pretty well.
So his latest update, he's now at $15,000 a month in revenue and he writes about how
he's completely underestimated how big his app could get.
He totally under invested in it.
He hasn't spent a single dime on paid marketing and instead he spent like the last few years
just working on other apps.
So he kind of regrets it and that was going back to work on mantra and give it more of
his attention.
Sean, you should tell him about Horoscopes because that's the exact same thing here.
What about Horoscopes?
Did we interview the guy?
His name was Ross.
There's this guy who raised money from a bunch of New York media folks.
Maybe he raised $15 million and his app was in the same space as this mantra app.
But basically, Cortland, did you know that women love Horoscopes?
I've yet to date anybody who wasn't into astrology, so yeah, I'm aware.
I dismiss Horoscopes as some woo woo nonsense bullshit, but even smart women like my wife
and Sean's wife are into it even if it's at a casual level.
I was thinking, oh, I'm also into a ton of bro science as well, so it's just their version
of bro science.
So there was this app that raised maybe 10 or 15 million and they're probably making
millions of dollars a year doing Horoscopes.
Then we went and found Horoscope, was it Horoscope or Sudoku?
Something like that where it was like the most old school, not nice looking website
and they were very likely could be making 10 million a year off of these things.
And it was just getting crazy amounts of traffic because the amount of people who read or consume
Horoscope content is like half of America, because it's like 80% of women check it with
Mombre.
And it's smart too because it's daily.
You don't just check your Horoscope once and then never again.
You come back and check it every single day.
It's like what we were talking about earlier with the news and entertainment.
This is something where you can collect subscription revenue and people aren't going to stop coming
back.
I was given an example of there's a guy who's building some app that connects you with experts,
so it's sort of like, oh, if you're redoing your kitchen, you can actually get a 15 minute
video call with that person from HGTV.
So they found all these like, hey, Justin Bieber stylist will give you style advice
for 30 minutes if you want to pay 150 bucks or whatever.
So it's sort of like Cameo, but you're booking these 15, 30 minute calls with the who's who
of fashion, beauty, home improvement, all these categories.
And I was looking at their number and I was like, oh yeah, that's great.
You've seen some growth.
Which vertical is it?
They're one winner and they were like, yeah, you know, it's spread out.
And I was like, yeah, but like, certainly one has to be doing better than all the others.
And they're like, yeah, actually astrology is doing pretty well.
And I was like, it's like not even on your site.
He's like, yeah, it's like over there on the far right under this thing.
Because even he was kind of like, you know, it's not the thing we want to lead with what
we're fundraising.
Like he didn't say all that, but like you could tell it wasn't the, it wasn't what he
thought would win, nor was it what they were promoting the most, but it was the thing that
was working the best.
And he showed me.
And so I went down the rabbit hole again, I'm professionally curious.
So I go on Instagram and I start finding all the Instagram astrology accounts, astrology
influencers basically.
And it's like 80,000, 90,000, 200,000, 500,000 followers.
And these are like, just like, you know, some chick in Florida or like, you know, some chick
in like Huntington beach who like, you know, dresses the way you would imagine.
And like her, her, every, every post is like, oh, you know, like the shockers are aligned.
And like today, if you experience a good event, it's because I told you this or whatever.
Right?
Like some bullshit.
And, um, and then in like Lincoln, the bio is basically like an only fans to book a reading
with her and you go, I'm like, all right, hell yeah.
Let's book a reading.
Let's see.
Let's go end to end with this, this professional curiosity.
And it's like sold out.
Just every session is booked for like weeks.
And um, and so what he was doing was those, some of those people were using his platform,
but even the others were just using a bootleg version of this.
It made me think there is an only fans for, uh, for palm reading, astrology, horoscopes,
you know, like sort of like relationship, like voodoo or whatever.
And like the same thing happens, not just like in America in India, this is a huge thing
in India.
When you have a kid, you take your kid to like the local guru.
Cause of course every village just happens to have like a mystical guru that lives there.
And he'll like, you know, he's like Rafiki holding the baby, you know, Simba, he like
looks at him and he'll just like, he'll write you on a scroll, like your whole life story.
And like the do's and don'ts, it's like, you know, don't eat black beans.
Don't get married in the month of September, you know, don't date anyone with the letter
J and in the name.
And it's like, and people believe this, like to their core, they're just like, Oh, you
know, he's a great guy, but like his name is, you know, uh, you know, Trajan or whatever.
It's like, he's got a J in there.
We can't, we can't date trade.
We got to break up with Trajan here.
And it's like, like people believe this in every, every walk of life.
And I think that's one area that like a Silicon Valley doesn't talk about, but, um, B there's
just a lot of simple software solutions you could build that, uh, that can get you maybe
not to a hundred million in revenue, but like you can get to 10 K a month of profit.
You can get to 50 K a month of profit doing these, it'll make you rich.
Like, yeah, we, uh, we like talk a lot about that on the podcast where like it's pretty
like raising money and going big.
I think it's sick and I'm happy that the people who do it do it and maybe I'll do it one day.
But if you're like goals to optimize for like wealth creation, some of these apps or smaller,
relatively smaller ideas are actually significantly likelier to make you wealthy and perhaps be
more fun along the way.
And a lot of them are just repurposing ideas that have existed in the past in some form
or another that used to be doing really well.
So you can kind of just look at like what people used to do that worked and then just
try it again.
So like the horoscope industry, you know, has always had these influencers who people
really trust.
And I don't know if you guys remember Ms. Cleo, she had this like mystical hotline in
the nineties.
Yeah.
Oh yeah.
Okay.
She had like a billion dollars or something.
It is.
Yeah.
I mean, she, she was just a hired model or like, I mean, she actually was well, she wasn't
mystical or she was like, she was like a professional palm reader, but like the owners of the marketing
company like heard her speak and they're like, Oh my gosh, like you are, she's perfect.
You're going to be our woman.
You know, you're our, our spokesperson and they paid her like not, you know, like a hundred
grand a year or something like normal salary.
And uh, it was pretty wild and a lot of this stuff seems scammy, but here's, there's other
examples.
Like there's like sleep is a great category.
So you're talking about calm and one of comms biggest features is sleep stories and uh,
it's a paid feature, but like we met, we know and have met owners of sleep apps that do
everything from, you know, just white noise or like raindrop sound effects or whatever
to sleep stories to sleep stories, but just in other languages and they just focus on
like, you know, the Spanish speaking market or whatever.
And there's just like an infinite number of these niches that exist both in software or
you know, D to C like, for example, um, just to tie it back into what we're talking about
earlier in the D to C space, uh, like the fact that Tim Ferriss doesn't have his own
like nootropic drink or like kettlebell brand left money on the table.
You know what I mean?
Like, and the person who actually did this really well, uh, was Joe Rogan and, um, you
know, right.
He has like alpha brain or whatever that, that, that supplements company is.
And I think Sam, you know, the number is better than I do on this, but that's like a hundred
million dollar a year company, I think it just sold.
Maybe I'm a little over.
Yeah.
It just was acquired the other day.
And, um, friends who know the company told me it sold for $350 million and that Joe owned
like 20% of it.
Right.
And so like he, hey, that's his, his own passion area.
He talked about it in new ways.
Why take sponsors money to talk about somebody else's brand when like you could just be part
owner or white label, any of these things, right?
So there's a whole suite of those types of ideas.
And this happens again, like to look at another country, look in India, all the famous like
kind of like gurus in India, it's like, Oh, this guy's a saint.
He only accepts donations and like makes millions of dollars off donations.
And then as they get famous, like miss Cleo style, like, I think the top guy like has
like his own ramen noodle company, uh, and like, right.
So he just licensed his face onto ramen noodles and crackers or something like that.
And it's like a billionaire from, from this ramen noodle company.
And uh, yet at the same time, it's supposed to be this like religious saint, just the
most basic stuff.
Right.
But like, we can learn from them.
I learned this, like, what is this solo, like kind of solo creator playbook where you got
to know what are all the tools in the toolbox and then use the ones that, that you want.
But actually I was going to ask you a different question, which is Joe Rogan remind me of
this.
Who is having the most fun with what they do for a living?
Uh, somebody had asked me this question or in our group chat, somebody asked this question
and I was like, that's a great question, right?
Because once you see that, you see a model you're like, and it's not, they're having
the most fun, but it's like, I think that would be super fun.
If that was me, it's kind of like one question, one version of the question, um, because that
because that can become a blueprint then like, why don't, why don't I just go in for that?
And my answer was Joe Rogan and I'll give you kind of my defense for Joe Rogan.
But I would love if you guys have other answers of somebody who you've seen just having a
blast or you they're having a blast and you think it would be a blast for you too.
I'm curious if there are any other answers, like the Joe Rogan reasoning to me is he basically
he's got the podcast, which like clearly he does for fun because he was doing it before
it made any money before he sold it to, you know, before he sold the rights to Spotify
for a hundred million dollars a year, he was doing it for free kind of in his, in his bedroom.
And when, when there was no promise of money.
So he's just meeting badass people, Elon Musk, Neil deGrasse Tyson.
He's just having conversations with interesting people through that.
He gets a bunch of fans who love him.
That sounds fun.
Then he loves the UFC.
He's the UFC commentator, but he also does it where he doesn't go to every event that
would be exhausting.
That would be like the trade-off where the job become the hobby becomes a shitty job.
Instead he's like, no, I'm only going to do the big paper views in Vegas.
So that's an easy flight for me.
I'm not going to travel around the world trying to chase this thing around anymore.
So that seems fun.
And then he's a standup comedian, which is like a hard challenge, super fun thing to
do.
And he sells out arenas all around the world.
And so like, and then he's got his brand alpha brain or whatever, and he works out all the
time.
Like Joe Rogan just seems like he is doing all the things he wants at the highest level.
And so it seems like that's a blast.
Who do you guys think is having the most fun?
Okay, I'm going to go with the founder CEOs of these humongous, like $100 billion plus
tech companies.
And so I'm talking about like the Patrick Collison's of the world, Bill Gates, Larry
Ellison and Oracle, Jeff Bezos and Amazon, just these absolute titans who are controlling
a ton of resources.
And they're not like just some hired guns, CEO who came in later on to like turn the
ship around.
Like these are people who are working on the projects that they started that used to be
tiny.
So it's kind of like their life mission.
It's kind of like their baby.
And once it gets big enough, like it takes a lot of work, a lot of heartache to get to
the point where they're at now.
But once it gets to that size, like you can kind of delegate most of the important, like
urgent work to other people, like your trusted lieutenants.
And then you're kind of, you know, in control of like a massive amount of resources where
you can work on your favorite thing, and you can do side projects and all sorts of stuff.
So I think that's kind of the most enviable position to be in.
We're having, I think next week, we're having the co founder of HubSpot on Darmesh.
And I'll ask him, but I talked to him regularly, and I'm almost positive he doesn't have any
direct reports.
And I'm also, you can look this up, actually, I think he's the largest individual shareholder
of HubSpot.
And his value of just HubSpot shares is over a billion.
And I was like, What did you do this week?
He's like, Oh, I bought my wife for her 40th or 50th birthday, I bought her this domain
called humanist.org.
It's like a, it's a, it's this like philosophy we buy into, and it's this community.
And I was like, Is this what you do for fun?
He's like, Yeah, I'll have to ask him, so I'm not insinuating this, but it appears as
though he's got a pretty nice life.
And I agree with you that having the resources of a huge company is quite amazing.
It's almost like you're at the top of a cult, where you've got millions of people and like,
you know, maybe they're not following you because they believe in you.
They're following you because they're getting paid, but they're still following you nonetheless,
they'll basically do whatever you ask them to do.
You can set up whatever lifestyle you want to do.
And you have a certain amount of power that I think comes from only having lots of people
working in concert with you, that you can't get just from having lots of money.
You know, you can deploy that money if you're super rich to get people to work in concert
with you.
But if you have a company, kind of everyone's bought into the Kool-Aid and they're pushing
in the same direction.
And you can launch any sort of cool, fun side project that you want to, or you could just
go take off for a few weeks and like people won't really notice that you're gone because
everything's sort of delegated.
And when I compare that to like the content creators of the world, like Tim Ferriss, I'm
sure Tim Ferriss has some fun, but it seems kind of stressful to like have to be Tim Ferriss
all the time.
By the way, it's definitely stressful.
My I mean, he's like, blogged about like depression and shit.
And he suffers.
Although I would say that's part job, part genetic.
But my best friend Jack Smith, Jack Smith sold his company for $800 million or something
like that.
He probably walked away with before tax nearly nine figures, so nearly $100 million.
He started the company when he was 23.
He quit working there at when he was 26.
He's now 33 or 32.
He lives in a house in Hawaii.
He has no social file.
He has a Twitter handle.
He has a Facebook profile, but he doesn't like he probably has 150 followers.
He's not trying to impress anyone.
He doesn't do any angel investing.
What he does in this free time is he's a pen pal for inmates in prison.
And so he's currently pen paling with this guy who's like a math who like taught himself
math and he like gets joy out of helping the guys like, yeah, I want to get this book.
And so Jack just buys him the book, like the math book and he enjoys conversing about it.
He he loves testing different supplements and testing different products on Amazon.
And he doesn't have that need to create content or be a big shot.
He's incredibly comfortable in his own skin.
His wife started coffee meets bagel.
So she's also a big shot.
And so he lives on the beach in Hawaii in a rental unit that he probably pays ten thousand
dollars a month for.
And I think he is having the most fun because he doesn't feel the need.
I think both Sean and I and probably you, Cortland, because we're like these like public
facing things.
We definitely have this need to be loved.
Jack doesn't really have that he he only wants to be loved by his close friends.
And I think that there's something great to be said about like contentment and like humbleness.
And you you are happy with what you have and you don't nearly you don't really need much
or want more.
And he's also not like on the content treadmill.
No he doesn't need to.
He's not on any treadmill.
He's not on the money treadmill.
He's not on the on the social climbing treadmill.
He's not on the content treadmill.
He's not on any.
I kind of agree with you, Sam, which has its downsides like not having a mission.
Sometimes it seems to get sad.
So it helps like pick a project.
But go ahead.
I was going to say I so I totally disagree with what you said, Cortland, and I kind of
agree with what you said, Sam.
I'll give you both.
So, Cortland, I totally disagree in the sense that what I've seen, at least, is the kind
of the CEOs of the unicorns.
Here's your day.
Your day is mostly a combination of people problems.
So like, you know, your whole job was to put the right people in the right places.
But then all but people are one of the like buggiest pieces of code out there, right?
So you're always debugging that you're always debugging people.
And then the second thing is you put not fire.
So there's like always a fire at any big company, any sufficiently large company.
There's always, you know, some rotating set of crises every month.
And you know, that requires your attention.
And so like, you know, I don't think when Zuck creates Facebook, he wants people to
be like sharing cool photos of their lives.
He doesn't want fake news, misinformation.
And like, you know how much of these guys's day has to like, go into like solving the
gnarly problem of the of the moment.
And so, so I think, you know, they try to hire away that.
But like, they're accountable for it.
And so they have to like, ultimately deal with with these problems, people problems,
then you have big company problems.
And the last bit is like, you sort of lost the magic and the connection and the fun of
like, building something yourself hands on, which is probably what you like to do if you
started one of these companies.
Secondly, working with a small group of people, because now the place is so large, you don't
even recognize people in your own company.
And also, like you lose the like, you, in order to make a large company run, you need
to recruit certain types of people, right?
You need generals of armies, and not like guerrilla warfare, like you're used to at
the beginning.
So a lot of your good friends from the beginning of the company have moved on to do other things,
if you're still there.
So I've seen there is a big trade off in addition to the cool stuff you mentioned.
And so that's why I wouldn't say there's too many trade offs for me to say, Oh, they're
having the most fun.
I think they're the busiest.
I can see it's striped, you can see everybody's calendar.
And I just like pulled up Patrick Colson's calendar, like, what's this guy doing this
week?
And I can see like every single event that's on it.
It's not.
Let's go, let's go, let's go.
It's one of two, right?
It's either 30 minutes, 30 minutes, 30 minutes, 30 minutes, and there's an executive assistant
or two dedicated to like, getting this, like they were, their job is his calendar, basically.
And like, everybody wants his time and he's got a, and he wants his own time.
And so, you know, there's 30 minutes back to back everywhere.
And then there's the other one, which is super sparse, where it's sort of like, well, I kind
of don't do anything now, which is sort of fun at first, but I could also just quit if
I really wanted to do nothing.
So instead I'm kind of like in this like slightly unsatisfying position of like, my job is not
to do any of the jobs.
It's a, and I'm sort of doing nothing, I'm supposed to think about the vision and shit
like that.
And so what do you think about that?
Is that true?
Which one is he?
It's the first one.
It's a 30 minutes, 30 minutes, 30 minutes, hear them, but also like, he does a lot of
projects outside of that.
And it's like very strictly like eight to five, nine to five, like then done.
There's nothing outside of that.
There are no obligations.
And like he is working on extra projects.
So he does, for example, the fast grants during COVID, where they're giving out money, which
is awesome.
Researchers are super awesome.
And this is like a kind of a fun project.
And before that, he was working with Tyler Cohen on doing a research project with like
why scientific progress has like slowed down.
He's also like learned to fly planes.
I was talking to him a couple months ago about like a project we might work on together.
Just the two of us about like helping to fund like underrepresented minorities and groups
to like basically cool, do cool things.
And so it's like, I don't know if he's a superhuman who just works 16 hours a day, but like he
is somehow finding time to work on all these cool pet projects with like small groups of
people and to fund it because he's got the resources of an entire organization behind
him.
So it's probably you're right.
It's like not the most fun job.
He still has like a crazy amount of responsibility to buy or whatever.
He could cut out the stripe part and do all those things also.
Right.
Yeah.
If he wants to go to the things, Sam, Sam brought up a good point, which is like, there's
the people who no longer are chasing desire and they're happy because they're sort of
at peace.
They're not just like at war with some part of their life.
And that's like, you know, the monk, but there's like the modern day monk and you would do
meet some people like this who just like, they're not like driven by their desire, if
their desire, right?
Cause desire is basically saying I lack something, right?
And so you're, you're agreeing to be unhappy with the current thing to go desire more.
And then there's like the people who I think me and Sam try to be more like right now,
which is, I don't think either of us try to be the guy with no desires.
I think we try to be, well, I have healthy addictions.
The things I want, I think are positive for me in the world and the pursuit of them will
make me ultimately better, healthier, have more fun and a happier person.
All right.
So like the, I got to choose an addiction.
At least I chose a healthy one.
And I think those are the people like kind of second, second, second most fun.
What's the end game though?
Cause I'm like, I guess in a way like me and Sam are like following your footsteps.
Like both of our companies got acquired.
Both of us are still working at the acquirers.
Like I don't have an end in mind, Sam.
I don't know if you have an end in mind saying like, when did, when do you quit HubSpot?
And when did you do after that?
I don't have an end in mind.
Like I think that you and I, Cortland are in different positions, maybe, well, you guys
don't have like, like, I don't have like a goal that I have to hit.
And if I don't hit it, I don't make money.
So like, truthfully, like my life is awesome.
Like I thoroughly enjoy what I do.
I spend most of my time doing a podcast stuff.
I'm happy.
I'm happy with my life.
I think that I enjoy being a HubSpot employee, inevitably, I'm going to quit.
And when I do, I probably won't start something.
I'll probably chill for three, four or five years and then start something.
But there, I don't really have an end game.
I do think about it a lot.
And it stresses me out.
So I try not to think about it.
I'm really trying to enjoy the journey as much as possible.
I'm in a position now that like, I have no once out of like, I have, I'm happy where
I am, I would be happy with significantly less though.
And so I'm a little I'm quite in a satisfied area for now.
I like, like I do experience envy, like, Sean, people love hit when he invests in their company.
And I'm like, fuck, that's like easy money.
That's a great deal.
And he also is really good at spotting them.
And so like, I experienced like envy or I experienced like, Oh, I want to do that too.
But it's definitely not like a, I'm willing to dedicate my life to doing that at the moment.
Sean, what's your end game?
Because you don't have some date, you know, in the future, like Sam does where he's gonna
quit and do something else.
You kind of just like staring ahead at the rest of your life.
So what's, what do you do when you don't necessarily have like a specific goal in mind?
Yeah, so I'm basically chasing this thing called the perfect Tuesday.
And what I realized was having these like goals or milestones or accomplishments is
a false promise you make with yourself where you're like, Oh, that's what I want.
And then, you know, as you get there, you're like, okay, well, you move the goalposts and
you want something more, right?
Like already I have more than I would have ever asked for 10 years ago.
And now I'm like, Oh, I want more, more, more, more of this, like this disease of more.
And so instead, I basically went the other way.
And I was like, okay, instead of thinking about what's this 10 year vision for myself
and what's the end game, it was sort of like, what's the now game?
What is the, what is the perfect Tuesday for me right now, the perfect average Tuesday.
And so I did this exercise once that kind of changed the way I look at things, which
is I said, what's the perfect normal day for me?
And I'm not perfect.
Like everything goes right.
But like, if I was just to do all the things I love in a normal day, what are all those
normal things?
And they're not that hard, right?
Like it's like, you know, I love to wake up without the alarm.
So like, I love to wake up naturally rather than an alarm waking up saying, Oh, shit,
you got to do something.
I'm feel groggy.
So now I wake up around 730, just gonna start going to sleep earlier because I got a kid,
but like, I don't wake up with an alarm anymore.
And so that, that already was like one thing is like, these are gonna sound really stupid,
but like, I'll just give you, I'll just walk you through some of the examples, like of
how stupid this is, which is like, I like, I love to shower.
Like I just love having a shower.
I'm like, I get great ideas in the shower, shower super relaxing.
I just noticed like on a normal day, that's like one of my favorite parts of the day is
taking a great shower.
And so then two things, I like started to appreciate this thing that seemed really mundane.
It seems like stupid to have a goal of taking a great shower every day.
But now I have a goal of taking a great shower every day because I know I love showering
a workout.
I love to work out.
So I want to have a great workout every day.
And not just like generically, a great workout, it's like, what are the most fun types of
workouts for me?
I want to do those every day.
So I have this day kind of mapped out where I'm like, these are the things I love doing
on normal days.
They don't take an outstanding event or it's not a vacation.
It's like, if my normal day was like this, I'd be a happy camper right now.
And then I, so I have like a great day that I mapped out in a great, what's a great week?
Meaning like, what's the thing I do once a week?
I'm not going to do it every day, but I want to do it once a week.
What's a great month?
What's the thing I want to do once or twice a month that I'm not going to do every day?
And then what do I do once or twice a year?
And so I wrote those out and I, I love this exercise so much.
I had my mom do it.
I was like, mom, you're getting old.
You got to be having great days.
All right.
Like, you know, you don't think of yourself as an ambitious person, but you should be
like, you've, you've, you've did all the hard work.
You raised the kids, you worked your whole life.
Like now you should just be maximizing joy.
I should also be maximizing joy.
This exercise helps me maximize joy.
And so now I'm basically just chasing, architecting my life so that I'm having that perfect Tuesday
as often as I can and getting as close to it as I can.
And same thing with the things I want to do every once a week or once a month.
So I know it's a little bit convoluted, but that's what I'm after.
I know.
I love it.
It makes perfect sense.
I think out of every group of people on the planet, entrepreneurs have to be the most
neglectful of the present moment.
Like we're always obsessed with some huge goal we've set, you know, we're going to build
that company.
We're going to, you know, launch this app and we kind of forget about the days in between
now and then, you know, like we just sort of neglected it.
We neglect the present for the future, which is done because the present is what life is
made out of.
It's made of an endless string of present moments.
And so, uh, if you want to have a good enjoyable life, like you can't, you have to kind of
resist that entrepreneurial urge to only care about the day.
Like if you just imagine, like draw, uh, draw a line and that's the time of your life.
Right.
And like, let's say it's a year or 10 years that line represents.
And then like you have this milestone at the end, this goal at the end you're shooting
for and you have two options.
Either you say, I'll be happy when I get to the end.
Okay, cool.
Or you say, I'm going to have fun the whole way, all along the way, right?
Like it's very obvious when you draw that line, which of these diagrams is better.
The one where you have fun just in that dot at the end or the one where you have fun on
the, every single dot along this line, as it's so obvious is nothing new.
It's nothing insightful.
Everybody's heard this cliche of enjoy the journey, not the destination.
Like when I look at that diagram, I'm like, what the fuck?
Who cares what that end destination is?
I want this, like this line to be dope.
I want to be, I want to be having fun all the, all the way, especially if this line
represents 10 years of my life, then like I got to make that, that happen.
And so that becomes the focus.
Well, I think the issue is like people hear this and it's almost like a cliche and that
doesn't mean that it's wrong.
I think a cliche is something that's smart enough that it became common advice.
You know, it's about the journey, not about the destination, but it's still hard enough
that people have been repeating this for years and people still don't understand or follow
it.
You know, I think people hear this from a couple of rich guys like you two and they're
like, okay, yeah, it's easy for you to say.
But in their shoes, they often see themselves as having to have this difficult, arduous
journey to get to the point where they have enough money and then they'll use that money
to have a good journey and do something else.
So like Sean, you are at this point where you can design this cool life for yourself
in part because you have enough money that you don't have to go to a nine to five job
ever again.
And so when you say this, it's not like, it's not easy for other people to follow that advice.
Well, so what I'm saying is what I'm basically saying is I'm not telling people don't chase
the money.
I guess what I'm telling people is it's a false choice that you either, you know, you
suffer until you have money or you have fun, but you don't have money.
There are plenty of examples.
And so if there is even one example, that means it is possible.
There are plenty of examples of have funny, have fun and make a ton of money as a byproduct.
So if that's an option on the table, you're crazy for settling for anything less than
that, if you're a sufficiently talented person, right?
If you're a talented enough person, which most people are who are listening to this,
if you're sufficiently privileged and you have your faculties about you, that is an
option on the table, you know, have a shit ton of fun and make a shit ton of money, both,
then choosing one or the other is a silly option.
Okay.
So question for both of you, what's your favorite example or story of how somebody can do that?
Like if you're an indie hacker right now, you're just starting out, you got nothing.
How can you do something that works and that makes money and that's also allows you to
have fun.
Can I give one?
Yeah, give me one.
All right.
I was at a friend's house yesterday and he was like thinking about starting a he wanted
to help kids start shit.
And I'm like, basically, I think that like, if you wanted to if you are 18 years old,
and you had a summer and you wanted to build a business that made $100,000 a year, I think
it would be shockingly simple, not easy, it would be hard physically, to just dominate
Yelp for a local service that would take you only like three to six weeks to like master.
So maybe trimming trees or something like that.
I think that you could probably crush it that way and make hundreds of thousands of dollars
in a relatively straightforward, non intellectually challenging, low risk way.
I think that that that most people could probably do that, right?
I think it's low risk.
I don't think it's super like strategically difficult.
But also is that like fun?
Like how many people really enjoy going out in the hot weather and like trimming trees?
I don't mind.
Like I just paid a guy $80 an hour to come to my house off TaskRabbit to power wash.
And he had like a rinky dink $250 washer or whatever.
And I asked him what his plans were for the day.
And he was like, I've got eight of these planned.
So I mean, like, and is power washing that like I know does anyone love it?
I don't know.
But it's kind of fun to like start a job and finish it and you can work outside in the
sun.
Okay, I've got one.
It's a company, another company that I found on indie hackers.
It's called high performers.
So the guy calls it masterclass as a service for pro athletes.
So I'm looking at this guy's timeline.
His first post is from November 2020.
He says, I spoke to five pro athletes, and I've got one of them to partner with me.
And then he helped this guy's athlete create a course, it's basically like a PowerPoint
presentation he created.
And he put it on Udemy.
And then he helped this athlete sell the course to his own followers on social media.
And so now, eight months later, he's got this whole process on repeat.
He's hired a salesperson to do all the outreach.
So he only has to do the part that he likes, like actually working with the athletes and
creating the course.
And he's making $10,000 a month, basically just doing what he loves and just making money
in the process.
And the idea isn't even that creative.
I mean, it's just masterclass for a niche.
I did this with...
There's this guy named Ben Askren, who's in the UFC.
And he's an Olympic wrestler.
And I was a fan of his, I became friends with him on Twitter.
He started talking to me about digital stuff because he didn't know anything about it,
although he had a huge following.
And I was like, why don't you start a course?
He's like, I have no idea how.
I was like, dude, I'll just call you once a week for like four weeks and we'll get the
shit done.
And he did it.
And he's got a wrestling course.
And so I didn't charge him anything, I just wanted to become friends with him.
But he would have paid, he offered to pay me money.
So I agree that that could definitely be a thing.
Right.
And you literally did that for free.
I mean, so that was just because you have...
Yeah, I think it's different.
People have fun doing different things.
So I'll just speak for myself.
If I was 21 again, or 22, or whatever, and I'm like, all right, how do I have a bunch
of fun and make a bunch of money at the same time?
What I would do is actually very similar to these guys who hooked me and Sam up with our
podcast studios that they set up for us.
And they're crushing it right now.
So here's...
They are 21, by the way.
They were basically like, hey, we're big fans of the show, right?
Because they are friends of the show.
I would be a fan of our show if I was a kid again.
And they basically reached out and they're like, hey, your guys' camera stuff looks
like shit and your sound kind of sucks sometimes.
We're really good at this.
Do you want us to come help you out?
I'll set your thing up for free.
Just basically pick a weekend.
Next weekend?
The weekend after that?
When can we come and set your thing up?
I'm tired of listening to you guys with crappy audio and crappy video.
And so we were like, okay, and then they showed us their YouTube channel.
They're like, oh, here's my YouTube channel.
I don't have a ton of followers, but just look at the quality and you'll see, would
you like to look like this?
And I'm like, hell yeah.
And then he sent me a menu.
He sent me three setups.
He's like, you could look like this famous guy, this famous guy, or this famous guy?
Which setup looks best to you?
And I was like, all right, fine.
Come on out here and give me option C. And he's like, great.
We'll be there this Sunday.
They flew out here.
They hung out.
They did the hard work.
They didn't ask for anything in return.
And I was like, dude, let me pay you guys like something like this is, you know, so
what would I get to do?
I'd meet somebody who I'm really like, I'm a big fan of.
I would hook them up with something using a skill that's pretty easy to learn, really.
Like they basically found some lights that drilled into the wall and then they like picked
the right microphone.
They plugged it into the right slot and whatever they just, they did the setup and then they
they followed up and they were just like, you know, already I was like, dude, I want
to, I'll help you guys out.
I'll mentor you guys.
I'll hook you guys up with you.
We want another opportunity.
What do you want?
And they're like, yeah, we're just trying to figure out what to do.
And what they figured out was there's a lot of podcasters like us out there that had really
good hour long content.
And what they did was they had a, from, from their own content, they had stumbled into
this setup where they find talented video editors basically overseas in the Philippines
or wherever else, and they trained them on how to edit clips.
And then basically they have a business where they just charge podcasters like us tens of
thousands of dollars a month.
Yeah.
Have you seen, have you seen ours, Cortland?
Yeah.
They look super good.
I see them on Twitter.
Yeah.
We pay them 30 grand a month.
They look super good.
Have you put them on a YouTube yet?
Cause I'm trying to find you on YouTube.
No, we are.
We suck at that part right now.
Forget that.
But I guess my point is these guys are making 30 grand a month just off us as one client,
right?
And they can make, they probably can't charge everybody that much, but they can have like
20 clients doing this and basically they're just doing labor arbitrage, talented people
in the Philippines.
Um, and then they're, they're getting to meet like yesterday's all in podcast, which is
like one of the most famous business podcasts.
It was like the whole first half of the thing was all about these guys.
They said their names probably 50 times.
No way.
You're kidding.
They talked all about him.
Like, yeah, this kid, Henry, Henry Bellcaster keeps sending us clips and, uh, and then we're
in DMS with them.
And Jamal's like, dude, you're DMing Henry Bellcaster.
Why?
And he's like, yeah, they do a great job.
They were like, it was like a professional infomercial for them.
They've become friends with these guys.
They're hooking them up with great content and sure enough, those guys started paying
for it.
And, and you know, the next in the next, these guys will be making one to $2 million a year
of profit if they play their cards, right?
As 22, 23 year olds just for operating a like, you know, sweatshop of video editors in the
Philippines.
Right?
That's what they're doing.
I can't believe they pulled that off.
They told me that they were going to try and do that.
And I was like, yeah, I mean, it'll work.
And these guys kept at it, kept at it, kept at it.
They killed me.
And what the podcast editor did for me, he basically kept sending me clips of my show
where he had edited, edited the episodes better than I was editing them.
So I eventually just hired him.
So what does that do?
That does three things, right?
You get good at content creation, because that's, you're basically practicing that craft
every day.
And that's a really valuable skill to start compounding at a young age.
Second thing, you meet a bunch of cool ass people that are highly networked.
They love, they know you and trust you.
And if you ever wanted to do a thing, if you have a bigger ambitions that you can hit them
up in one call and you're no longer cold, you're warm.
And then the last, and they know you're good.
They know you hustle and you do good work.
And last thing is they're going to make at least half a million dollars, probably close
to one to $2 million a profit off this business in the next couple of years.
That's you're a millionaire.
Congratulations, right?
You had a bunch of fun doing it.
So that's a, that's an easy example to me of something I would have done if I was their
age.
Okay.
So if we distilled this into like a playbook that people could follow, first you find something
that you genuinely like and you take the time to get really good at it.
And then you look to find somebody who's like famous or cool, who's not really doing that
good of a job at that thing and you do it for them for free and they'll probably take
notice because these are like hard workers who really want to get better at whatever
it is they're doing.
And so they'll hire you or they pay for your thing and they'll probably mentor you and
you can just repeat this playbook for anyone you like and make a ton of money in the process
while also getting to meet your heroes.
That's one path.
That's one path that works.
There are many.
That's one.
Cool.
Well, that's a good takeaway to end the show on.
Sam Sean.
Thanks for coming on.
Can you let listeners know where they can go to find your podcast and whatever else
you're looking on?
Yeah.
You can find our podcast.
You may have to scroll all the way up to the top of the charts because we're pretty high
up there now.
So just go all the way up to number one and then we're just below that.
So my first million in the podcast app store or whatever.
Follow Sam.
He's the Sam Parr on Twitter.
I'm Sean VP on Twitter, SeanPuri.com, that's my newsletter.