My First Million: SPECIAL: The Tools in the Solo Creator Toolbox

All right.

Quick break to tell you about another podcast that we're interested in right now, HubSpot

just launched a Shark Tank rewatch podcast called Another Bite.

Every week, the hosts relive the latest and greatest pitches from Shark Tank, from Squatty

Potty to the Mench on a Bench to Ring Doorbell, and they break down why these pitches were

winners or losers, and each company's go-to-market strategy, branding, pricing, valuation, everything.

Basically all the things you want to know about how to survive the tank and scale your

company on your own.

If you want to give it a listen, you can find another bite on whatever podcast app

you listen to, like Apple or Spotify or whatever you're using right now.

All right.

Back to the show.

What do NASA astronauts, Olympic athletes, UFC fighters, and world-leading neuroscientists

have in common?

They've all been featured in The Salesman, an award-winning podcast featured in the HubSpot

podcast network.

The Salesman podcast helps B2B sales professionals learn how to find new potential buyers and

win business in a modern, effective, and ethical way.

I love the Salesman podcast.

Why?

Because where on earth are you going to see fighters and athletes talk about selling

stuff?

But look, we're all selling something, so it's kind of cool to get their perspective.

So listen, learn, grow with the HubSpot podcast network at HubSpot.com slash podcast network.

If your goal is to optimize for wealth creation, some of these apps or relatively smaller

ideas are actually significantly likelier to make you wealthy and perhaps be more fun

along the way.

What's happening, podcast listeners?

This is Sam Parr.

I'm currently walking around Soho in New York.

It's Friday after work, and I'm doing something I never do.

I'm listening to a podcast that I was on.

You see, a couple weeks ago, Sean and I appeared on the Indie Hackers podcast with Cortland,

and it was awesome.

It was really good.

And I'm listening to this right now, and I was like, I think our audience are you people,

MFM.

I think you guys would love this.

And so I'm sitting here on my phone walking from Soho up on the water up to my apartment,

and I said, you know what the hell we're going to air this.

So I'm doing it right now.

We're launching it.

I hope you enjoy it.

Let us know what you think about this.

My Twitter handle is TheSam Parr, Sean is SeanVP, and on your Spotify, there's this new feature.

They got this little bell.

Click that bell for me.

That way you'll get notified when new features and new episodes come out and let me know

if it works.

We'll talk to you soon.

Have a good day.

I'm going to enjoy the rest of my walk.

Listen how loud that is.

Can you hear that?

This freaking city.

It's so loud.

Oh my gosh.

Well, enjoy the podcast.

See you.

What's up everybody?

This is Cortland from ndhackers.com, and you're listening to the ndhackers 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 ndhackers 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 Puri and Sam Parr, two of my favorite podcast hosts.

You guys host the excellent show, My First Million.

Welcome to the ndhackers 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.

There we go.

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?

$9.

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 like, what's the valuation of Stripe?

I was more just thinking like, hey, I'm running this like really tiny, scrappy website.

Like, 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 like the perfect

sponsors for anti-hackers and Stripe was number one on that list.

Like 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 anti-hackers?

And so I was like, yeah, of course that's much better than getting a sponsor.

They, Sean, uh, Cortland, 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, they don't look identical, but yeah, they look similar.

But he came to my, he came to Austin like a month ago or three weeks ago and he came

over on like a Tuesday or 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 three or four a.m. like party and, uh, 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, now I got better things to

do.

Well, uh, last week for the very first time since the pandemic started.

Oh my gosh.

But yeah, he's like my right hand man at Andy Hackers, kind of in the same way that you

two work together on your show, my first million, uh, 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, uh, 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, uh, what happens is if you listen to

it, you know, most people who listen to it, they, um, 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, uh, 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 it's 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, I, 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, uh, 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.

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, uh, what is the typical aqua hire 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.

I think, 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, like a piece of heavy machinery behind it called, and it was, it said Van

Meer and our good buddy's last name is Van Meer.

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 Google Van Meer.

I'm like, is this like his great grandfather?

What is this brand?

I bet you do these tractor companies crush it.

How much does this Van Meer 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.

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.

I'm like, what the hell?

And they promised that it's going to make you like 0.5% more efficient and it's only

like $500 or whatever it is.

And I, so I did the exact same thing.

I saw this on this truck.

I'm like, I got to 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.

And if I just call an episode business ideas for 2021, it gets like twice as many downloads

as every other episode.

Cause people were 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 you take the medicine, it's supposed

to cure the problem and it's supposed to like be able to move on with your life.

And some people just love drinking Robotessum 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 get it for, they 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 Shab 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 contents 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 of 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 the beginning it was

more like evergreen hits, long form, super interesting blogs, like kind of like going

for home runs.

Like 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.

It'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.

If you're a 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're

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 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 started 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 to, 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, uh, they give me the swag.

And then I show up, well, at least when you're in person, it's, 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, would love to pick your brain

about X. You know, you start getting pulled into all these strategy things because you're

the smart, you 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 Coralyn, you were 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 thing,

you know, like 30 people or whatever, pitch for funding basically, and your funding is

just headcount and resources.

And 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 know, I 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.

You understand.

He's a founder, so you understood.

He said, I said, but, you know, there could be a model here that works.

Like here's what, here's what I would like.

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,

learn to learn 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 cruising,

do is doing what, just the parts you enjoy with none of the stuff you don't enjoy.

And then, and then it's like, it gets the itch to go do the thing again.

That's the pattern I've seen.

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 yeah, how dare you.

But there's like, you know, the people pleaser in me was still like a little bit hesitant

to like, just be fully honest.

But when I did, I was like, Oh, great.

This is no problem.

They understand.

And so, 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 you.

Yeah, they'll be a new you.

We've seen this turnover five times.

And there's also this middle ground, which is like, you, it does, 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 glum onto 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 trusts that you're building with your audience day after

day.

It's going to show up and prove into people that you actually are who you say you are

and you know what you're talking about.

And the 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 Sahil from gum road.

He started gum road, gum road's huge.

And that doesn't necessarily mean he's super liquid, right?

Like the company throws 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 Sahil.

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 it would be once every week, once every few days, somebody

just puts like $20, $25,000 and do his 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 this same path.

Yeah.

Well, 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 some way I got my hands on for our work week.

And I had what you call the four hour fever, which is when you finish 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?

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 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.

That'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 blog, essentially.

And then later, a podcast later, a newsletter, other things.

He translated his fame into access for deals.

So he invested in Uber, invested, I think, at Twitter, a couple, couple other big ones,

he 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 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 because 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, 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.

Tim actually knows him, but I'm out of him once and it seems 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 up market, raising money from investors, having

a team that you got to go into the office every day and rah rah, keep everybody happy

and keep everybody motivated, come up with your strategy.

So I 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 am I just going to put

away 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 me Tim Fares, it's like you said, he was like one of the only ones doing that.

It wasn't like a very clear path to follow.

Whereas now there's just so many different issues to get into.

You see that there's levels.

Yeah.

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 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, 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.

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 investments.

Like 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 just kind of took their best blog posts that they

had proven work to the best and they turned them into like bestselling 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 Corp, 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.

The subtle art of not giving a fuck.

It was, it 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 $2 or $3 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 can be ridiculously lucrative, but it's hard.

Like James Clear, again, he had a million email subscribers.

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

could probably negotiate to get higher than like the end issue standard of like 15 percent

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, so highest to lowest

was investing, advertising revenue, and then significantly blown 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 100 million plus.

I mean, being early to $100 billion startup 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, you know, for me, I used was this idea of a rolling fund, Sam

does SPVs and syndicates on Angelist.

So like, I'm pretty sure Tim was investing his own money.

Maybe there was like some back end deal where like, whatever, Sequoia gave him money as

a scout or something.

But I think he was just investing his own money.

But like, 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, you know, if people want to co-invest

in deals with me, I've been investing and here's, you know, 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, 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, my 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 $80,000 a year.

So that's like, you know, pretty much like a starting salary, you know, for, yeah, I

mean, that's like, that pays the bills.

That was my salary, you know, 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, or 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.

So and the startup investments take, you know, 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?

So a good fund might 3X in value.

And so, you know, a good fund, it could do better, but, 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 becomes like 30 million in equity

value.

And this is for something that I, you know, put that's, I just, 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 be 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, you know, Tim Ferriss, it didn't

exist for Tony Romes.

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, 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 and he's got like a job board.

And so he's big in Bitcoin and he's, that's what he's known for.

So he created Pomp's crypto jobs.com or something like that.

So he's making, I believe he didn't, he didn't confirm this, but you know, 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, you know, 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.

Tim Ferriss could have done that, right?

But they didn't have these tools nor awareness to use it.

They were following the traditional playbook, which was like, write books, give speeches,

like go to, go get paid $30,000 to go talk at some company.

And the last one was like, he created a TV show was like, you know, go for mainstream

media.

And, 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, I still don't think it's like

necessarily the most accessible path to start with, because you got to build an audience

first.

Right.

And that's a dog eat 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 pomp, pomp 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.

I'm not, 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.

All right.

Look, most businesses have something that I hate silos, say it with me, silos.

What does that mean?

It means different people are using different information across your company and no one

ever actually knows what's going on or they're using one source of truth.

It's a pain in the butt and it costs you money, it costs you time and it hurts.

It hurts.

So with the HubSpot CRM platform, you can bring all your data together in one roof.

So this is like sounds a little fluffy and these big words, but I'm going to put it together

in a very simple and easy to understand way.

Look, you have salespeople, they're going out and selling stuff.

They need context.

They need to know who's talked to a particular customer.

They need to need to know how that customer has interacted with your website, with your

customer service.

They need to know what's going on.

So when they go and talk to that potential customer, they can make the sale and they

can get it done.

Now most of the time they're going to be prospecting, spending tons of time researching.

How does this person know us?

How do we know them?

What's their background?

Yada, yada, yada.

That's a pain in the butt.

That is called silo information and wasted time.

You don't want to do that.

That is why HubSpot CRM platform exists.

So with the HubSpot CRM platform, we're bringing together all the data under one place with

no lags between marketing and sales.

Need to sync your data and keep it clean?

No problem.

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This is music to my ears.

So check it out.

HubSpot CRM platform, just go to HubSpot.com and save about a decade of tears and crying

and heartache over not being able to have your data across your business.

Check it out.

Okay.

So let's get into some ideas.

Let's talk about ideas that 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 Andy Hackers.

I'll go to the Andy Hackers product directory and I'll sort by, 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.

I was like 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 Andy 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 his thought 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 so it turns out 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 underinvested 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 now he's 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.

He was the guy who raised money from much 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.

So even 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.

And I was thinking like, oh, I'm also into a ton of like bro science as well.

So it's just like their version of bro science.

And we found, 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, was it horoscope or Sudoku?

Something like that where it was like the most like 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, like half of America because it's like 80% of women.

And it's smart too because it's daily.

Like you don't just check your horoscope once in the never again.

Like you come back and check it every single day.

It's like what we were talking about earlier with the news and entertainment, like 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's like, it connects

you with like kind of experts.

So it's sort of like, oh, if you're redoing your kitchen, you can actually like get a

15 minute video call with this, that person from HGTV, right?

So they found all these like, hey, Justin Bieber's stylist will like give you style advice

for 30 minutes if you want to pay 150 bucks or whatever.

And so it's sort of like cameo, but you're booking these like 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.

Like which, which vertical is it?

Is there 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, 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 while

we're fundraising.

Like he didn't say all that, but like you could tell it wasn't, 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 us 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, and then in like link in the bio is basically like an only fans to book a reading

with her.

And you go.

So I'm like, all right, hell yeah, let's book a reading.

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 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, 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, because 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, you know, Trajan or whatever.

It's like he's got a J in there, we can't, we can't date Trajan, 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, so looking at Valley doesn't talk about.

But B, there's just a lot of simple software solutions you could build that, that can get

you maybe not to a hundred million in revenue, but like, you get to 10 K a month to profit,

you can get to 50 K a month to profit doing these businesses and it'll make you rich.

Like, yeah, exactly.

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.

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 Miss Cleo, she had this like mystical hotline in

the nineties.

Yeah, you've heard.

Oh yeah.

Yeah.

Okay.

Like that business was crushing it.

Like they made like a billion dollars or something crazy about that.

Yeah.

I mean, she was just a hired model or like 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, you're gonna be our woman.

You know, you're our spokesperson and they paid her like not, you know, like a hundred

grand a year or some like normal salary.

And it was pretty wild.

And a lot of the 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 calm's biggest features is sleep stories and it's

paid feature, but like we, 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, just to tie it back into what we're talking about

earlier in the D to C space.

Like the fact that Tim Ferriss doesn't have his own like Neutropic 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 was Joe Rogan.

And you know, right?

He has like Alphabrain or whatever that, that, that supplements company is.

And I think Sam, you know, the numbers better than I do on this, but that's like a hundred

million dollar a year company, I think maybe I'm a little over.

It just was acquired the other day and 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 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 in 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 of donations.

And then as they get famous, like Ms. Cleo style, like, I think the top guy like has

like his own ramen noodle company and like put, 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 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.

Like if you're trying to learn 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?

Somebody had asked me this question or in our group chat, somebody asked this question

and I was like, it'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.

Because that could, 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 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.

And 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 brand 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 a hundred billion

dollar 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, um, I think next week we're having the co-founder of HubSpot on Darmash.

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 share

holder 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.

It's like, it's the greatest job on earth.

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.

You can see 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, um, 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, 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, he's a pen pal for inmates in prison.

And so he's currently pen paling with this guy who's like a mat who like taught himself

math and he like gets joy out of helping the guy's 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 loves, um, 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, um, coffee meets bagel.

So she's also a big shot.

And so, uh, he lives on the beach in Hawaii in a rental unit that he probably pays $10,000

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.

He doesn't have this need to be loved.

Jack doesn't really have that.

Uh, he, he, he, he only wants to be loved by his close friends.

And I think that there's something, uh, great to be said about like contentment and like,

uh, humbleness.

And you, you are happy with what you have and you don't nearly, we 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, any show.

But I kind of agree with you, Sam, which has its downsides, like not having a mission.

Sometimes it seems to get sad.

So I'll have to like pick a project, but go ahead.

I was going to say, I, I, so I totally disagree with what you said, Cortland.

And I kind of agree with what you said, Sam.

So 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, uh, 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, um, you're putting out 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, uh, 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'd like to do

if you started one of these companies, uh, secondly, working with a small crew 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, um, 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 were 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 was 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, at Stripe, you can see everybody's calendar and I just like pulled up Patrick

Collison'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, it's not, 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 to let, 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, 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 the 30 minutes, 30 minutes, 30 minutes.

Here the meeting is, 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.

Those are awesome.

It's 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 of months ago about like a project we might work on together,

and there's the two of us about like helping to fund like underrepresented minorities in

groups to like basically do cool things.

And so it's like, I don't know if he's a super human who just works 16 hours a day, but like

he's 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 probably you're right.

It's like not the most fun job.

He still has like a crazy amount of responsibility.

He could cut out the stripe part and do all those things also, right?

Yes.

Yeah.

If he wants to go to these things.

I 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 meet

some people like this who just like, they're not like driven by their desire if they're

desired, right?

Because desire is basically saying I lack something, right?

And so 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 and 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 acquires.

Like I don't have an end in mind, Sam, I don't know if you have an end in mind, Sam,

like when did, when do you quit HubSpot and what do 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 podcast stuff.

Uh, I'm happy.

I'm, I'm happy with my life.

I think that I enjoy, um, 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, 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.

Um, and so I'm, I'm a little, I'm quite in a satisfied area for now, but 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, uh, 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 going to quit and do something else.

You're 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 we're 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, 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 and 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 alarm waking me up saying, Oh, shit,

you got to do something and 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, 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 is 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 a generically a great workout, it's like, what are the most fun types of

workouts for me?

I want to do those every day.

And 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, then 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 asking.

Oh no, 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 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 if you want to have a good, enjoyable life, like you can't, you have to kind of

resist to that entrepreneurial urge to only care about the, you know, like, if you just

imagine, like draw, 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 every single dot along this line.

Because it's like so obvious is nothing new, it's nothing insightful, everybody's heard

this cliche, I've enjoyed 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, 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 till 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 in the process.

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

also?

I don't mind.

Like I just paid a guy $80 an hour to come to my house off task, grab it 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, no, 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.

This is 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, this 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 was like, 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.

He did a wrestling course and so I totally, 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.

I mean, 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 like studios that they set up for us.

And they're crushing it right now.

So here's our 21, by the way, they were basically like, hey, we're big fans of the show, right?

Because they are fans of the show.

I would be a fan of our show if I was, you know, a kid again.

And, um, and they basically reached out and they were like, Hey, your guys's camera stuff

like looks like shit.

Your sound kind of sucks.

Sometimes like, we're really good at this.

Do you want us to come like help you out?

Like I'll set your thing up for free.

Just sit, you know, basically like pick a weekend next weekend, the weekend after that.

When can we come and set your thing up?

Like I'm tired of listening to you guys with crappy audio and crappy video.

And so we were like, uh, 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 like, 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, here's, you could look like this famous guy, this famous guy or this famous

guy, which, which setup looks best to you.

And I was like, all right, fine, come on out here and give me, give me option C. And he's

like, great, we'll be there this Sunday.

They flew out here.

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, so what

would I get to do?

I'd, 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.

Uh, like, you know, they, they basically found some lights.

They 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 this setup.

And then they, they followed up and they were just like, you know, already I was like, dude,

I want to all help you guys out.

I'll mentor you guys.

I'll hook you guys up with your, you want another opportunity.

What do you want?

And they're like, I would just try to figure out what to do.

And what they figured out was there's a lot of podcasts like us out there that had really

good hour long content.

And what they did was they had, uh, from, from their own content, they had doubled into

the setup where they find talented video editors, basically overseas in the Philippines

or wherever else, and they train them on how to edit clips.

And then basically they have a business where they just charge podcasts was like us tens

of thousands of dollars a month.

Yeah.

Have you seen, have you seen ours?

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 YouTube yet?

Cause I'm trying to find you on YouTube.

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.

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 said their names 50 times.

Like, yeah, this kid Henry, Henry Bellcaster keeps sending us clips and, and then we're

in DMs with them.

And she wants like, dude, you're DMing Henry Bellcaster.

What, why?

And he's like, yeah, they do a great job.

They're 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 and the next, these guys will be making $1 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 it.

I mean, that's what my podcast editor did for me.

He basically kept sending me clips of my show where he had edited it, edited the episodes

better than I was editing them.

So I eventually just.

What does that do?

That does three things, right?

Like content creation, because that's, you're basically practicing that craft every day.

That's a really valuable skill to start compounding at a young age.

Second thing, you meet a bunch of cool ass people who are highly networked, they love,

they know you and trust you.

And if you ever wanted to do a thing, if you have bigger ambitions, that you can hit them

up in one call and you're no longer cold, you're warm.

And then the, and, 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 $1 to $2 million a profit off this business in the next couple of years.

That's, you know, you're a millionaire.

Congratulations.

You're doing 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'll 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 it.

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

working 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, whatever, follow Sam.

He's theSampar on Twitter.

I'm Sean V.P. on Twitter, SeanPurri.com.

Machine-generated transcript that may contain inaccuracies.