What's going on man, bro? I just went to the Louis C.K. show at Madison Square Garden this
past weekend.
Oh, nice. How was it? It's been a long time since I've been to a comedy show.
Have you even been to any comedy shows? I don't know if you've ever told me.
I've been to lots of comedy shows back in San Francisco, like pre-pandemic. I used to
go with Celeste all the time.
Ah, that's true.
I've been seeing Louis C.K. He's a pariah. I mean, he masturbated in front of a bunch
of women and I thought that was a wrap for him.
Yeah, exactly. So actually, you know Dan Shively, right? My best friend from San Francisco,
he was a comedian and the only reason I would have gone to the show, because it's all super
controversial is Dan just messaged me out of the blue and he's like, hey man, I got
three tickets to Louis C.K. Do you want to go? It's going to be in Madison Square Garden.
He was flying from Arizona. So I'm like, all right, man. Yeah, absolutely. And I brought
my girlfriend along. She didn't tell any of her friends that she was coming. We get there.
It's hilarious. It's like, you know, 10 men for every woman that you see like just around
in Madison Square Garden. Every single one of the women clearly is just like the wife
or the girlfriend of some guy that they're with. There are no groups of women. There
are no like gay men, right? It's exactly the kind of crowd that you would expect. Like
a bunch of like white, like 20s and 30s guys. And then even the show itself was hilarious
because the first joke that he makes is like, thank you guys all for coming. I know every
single person here has someone in their life that doesn't know where they are. Like you
lied to about what you're doing on this kind of Saturday night. I don't know. I'm not going
to spoil the set, but it actually was really funny because I was there with Dan. Dan spent
five years like really seriously trying to become a comedian. I don't know. Did I tell
you about the time that Dan and I went to an open mic in San Francisco?
Yeah. You told me this because you did stand up yourself too, I think. And you had never
done stand up before. So you just kind of like did it. And then did you do good? Did
you bomb? I can't remember exactly the exact same thing is like, it's like, I don't even
agree that I did stand up. It was, he wanted to do stand up and he's like, Hey, I'm going
to do open mic and I need you to be a good friend and come with me so that if I bomb,
like you can bomb before me. And it was the worst experience I've ever had. It was good.
It was, it was a fun learning experience, but dude, I don't know if I told you like
the details are, we had like a gentleman's agreement where we're like, okay, I'm going
to have like a five minute set. He's going to have a five minute set. We prepared them,
but we like, we're like, we're going to walk in separately. This is like, you know, in
San Francisco, just a small bar, like 50 people and a, you know, a lonely mic on a stage.
And we like went in and pretended that we didn't know each other. And the idea was that
like he would sit in the middle, support each other and like laugh at my joke. That's genius
plant in the audience. Exactly. And I was going to be the plant for him, but I go first
and my, my like, first off my set sucks. So every joke that I give, he's laughing hysterically
and the entire room is dead. Silent. Um, dude, we got, we got Sean here and Ben. Hey guys,
can you hear us? Yeah. What's up guys? Can you hear me? Yeah. Hey, what's up? What's
up dude? Sean. I love your setup. You are, you're a price right now. Yeah. We got, uh,
we got like put my studio out. Yeah. Let me tell you a story. Okay. It's probably been
like a year since we last spoke. I moved to Seattle. I completely got out of the tech
game. Like half the people I know in San Francisco, I don't even talk to anymore. Almost none
of my friends in Seattle know anything about tech, our startups. They don't even know what
I do. Like I tell them what I do and they just look at me like with their eyes crossed.
But the other day I was sitting next to my girlfriend and she was checking her email
and I see these like two little diamond emojis in her inbox. I'm like, what is that? And
it says, you're a fucking newsletter in her inbox. Sean Puri, five tweet Tuesday. And
I'm like, wait a minute, Sarah, like how did you, how did you find like, why are you subscribed
to this? And she didn't even remember. She was like, oh, it's just as interesting. I
like this. I like this guy. So in my mind, I'm like, holy shit, Sean has made it. He's
crossed over into your girls. You're mainstream now, man. You're huge. Like you're like, I
feel like you've made it as a content creator. Well, I at least, at least I've made it. That's
the one thing that I always wanted was the tagline of being, of having made it. You know,
it's funny. I, uh, a long time ago I was doing my first startup when I was like maybe 21
years old and we had this terrible idea, but at the time we thought genius idea to somehow
we were going to promote our restaurant startup through viral YouTube videos. And I was really,
if we were honest with ourselves, we just thought going viral would be cool. Uh, but
we just wrapped it as a justification to waste a bunch of time trying to go viral. So one
of the things we did was, um, a challenge where we would brush our teeth with Wasabi
cause we were starting a sushi restaurant. And um, so we did this thing where we brush
our teeth with Wasabi and then we're like, you know, spitting it out. It's terrible.
It's like, you know, mouth's burning or whatever video doesn't go viral, maybe 400 views or
something like that, which like honestly I give myself a little credit for it. That was
actually a good idea for, for a channel just like, you know, punking yourself basically.
I think that's a lot of big channels have been built that way. Mr beast bit right there.
Yeah, exactly. Like milk boys, jackass type of thing. And so we, um, then later I was
at a casino one time and this guy points at me and he goes, and this is like, you know,
more recent and I think he, all right, this guy recognizes me. He's going to say something
about the podcast or the newsletter or milk road or something like that. He goes, you're
the Wasabi guy. I saw you brush your teeth with Wasabi and I was like, wow, that's a,
that's amazing. Like a decade later, this is a, it's like that 400 views is still paying
off.
There's only 400 people on earth who know you from that and everybody else.
And recognize me cause I look a little bit different than it is. Like, thank God. That's
what I wanted to be known for. We're finally. Yeah, exactly. Finally I knew it. It was like,
I told you so moment, but there was no one to tell. Uh, your, your numbers are huge.
Like I think last year you came out on the podcast and I was like a year and a half ago
and you were doing like a few hundred thousand downloads a month, which at that time was
already bigger than any hackers. Like I'm like, you know, around that number. And then
now you're like, I think my first million, even Sam get like 2 million downloads a month.
Is that right? Yeah. Something like that. That's a ridiculous amount of traffic and
like listeners. And I'm thinking, do you guys monetize from ads? Do you actually are just
HubSpot?
Well, we basically sold all the ad inventory. So HubSpot runs all the ads, but that's okay.
It's still good. Like, uh, that just means we don't have to do ad sales cause as it grows,
we get paid more. So it's not like, uh, like basically just saying somebody pre-bought
all of the inventory at a set rate. And then if we grow, we get paid more, which are you
like getting a cut of the ad revenue? Cause I feel like the ad revenue is like, I don't
know what the more downloads we get, the more we get paid. That's a sweet deal. Yeah. And
not only that, but you can do whatever side projects you want. So you and Ben here started
a newsletter. This one, my girlfriend doesn't subscribe to that I know of called the milk
road. It's a crypto newsletter. I want to talk about that cause you just sold it and
you guys could do anything, do whatever you want. Why did you start a newsletter about
crypto? Like what, what's the origin story?
First of all, let me introduce Ben because I think people don't know that the real main
character of a lot of my stuff is Ben actually. So this is Ben Levy. He, uh, we met a couple
years ago and it was sort of just like he was in a mastermind group that I was putting
together where there was like six CEOs or something like that. And his business was
actually somewhat boring. It was like, you know, doing well, but it was like kind of
a boring business. His updates were always, yeah, there's, you can tell he wasn't even
that excited about it, but every time somebody else in the group had something, he had like
the most on point strategy or advice or just like cut to the chase kind of like, um, comment.
And so I was like, I like this guy, Ben. And I was like, he seems kind of bored with his
business. I wonder if I could just pitch him like, yo, let's do something else. Hey, what
if you just stopped? And, um, and he was also just like, yeah, actually let's try something.
And so we tried one project, it went well, and then we tried another and now we've done
like four or five things together. The latest of which was the milk road.
So why did you do a newsletter? I mean, like, was it to make money? Uh, was it just cause
it was fun? Uh, obviously like it did very well, but like, what's the point what's going
through your head is like, this is the thing that we can work on together. Two reasons.
One was we thought it would work. So a lot of people overestimate like how much they
love one topic. I think it kind of underestimate that winning, like just succeeding is in itself
pretty fun. And so I had a very high conviction that this would work. So I was like, okay,
I know I'll have fun simply from the fact that this is going to work and we can talk
about why I thought it was going to work. But the second thing is me and Ben had been
increasingly interested in crypto. So I have this like, you know, philosophy, which is
sort of like, how do I give myself an excuse to do the thing that I'm already spending
my extra hours doing? Meaning like if my, if my interest is always already going in
that way, can I productize that? Can I, can I wrap that into a business? And I don't always,
but this one I was like, I clearly could. We were like, you know, a newsletter, probably
not the biggest business, but it would work. It would be a business. The second thing was
like, this will be a great excuse to force ourselves to learn about crypto every day
and meet a bunch of other people in the space. And I told Ben at the beginning, I was like,
probably some investment we're going to make off of this is going to make us more money
than the newsletter will basically just create a surface area for serendipity, create just
like a bunch of space for good luck to happen. Cause I figured crypto was where a lot of
luck was going to happen. So that was the mentality going in. And, um, there was just
a bunch of like good inspiration for why we thought this might work.
Do you think that, uh, that's how it turned out that an investment or two that you've
made from your newsletter has made you more money? Or do you think like selling your newsletter
and having ads on there, maybe the opposite, maybe the opposite. We've made a bunch of
money selling the newsletter, but one of the things we did to promote the newsletter was,
uh, Ben, you can describe my, my, my, what I thought was a genius marketing move that
actually turned out to not be so genius. Yeah. I mean the way we, the hook initially
was like, Hey, we're going to put a million dollars into crypto. And this was like, this
is about a year ago when crypto is still in the bull market. We're like, we're going to
put a million dollars into crypto and we're going to turn it into 10 this year. Uh, I
think we put 250 K into Luna subscribe, subscribe to the newsletter to see how we do it. Right.
This was like a, it was like bait. Watch me try to turn one into 10. And, um, that was
pretty juicy, but we, it said turned a million into like 200, just losing money in public
is one of the best marketing hooks. I think. Let me mention something that I think is really
brilliant and super underrated and what you just said, which is the process of like selecting
a thing to work on, especially if you, let's just be honest, like you're kind of in this
position where you kind of have, fuck you money, you have a lot of different options.
Um, so many people think, well, what am I passionate about already? And I want to go
work in that. One of the cool ways to like create passion is just to enter a space and
then win in it. And then you end up getting all these other byproducts and like, you know,
sort of happy outcomes. You learn a lot about crypto, you make a lot of different connections
with people, what you want, and you're doing something that makes money and like that intersection
is where you want to be.
Yeah, exactly. I did a kind of an audit, which was like, yeah, what do I want to do? I was
like, what do I want to do? And at first I was thinking, I think the way most people
think, which is like, what should I do with my life, my career. And I thought about like,
you know, some like distant goal, like, Oh, I want to make this much money or I want to,
uh, achieve X and change the world and whatever. And, and there was something that just wasn't
sitting right with me about that way of thinking. And I, I felt like it was a little bit just
too artificial. It was like, um, this sounds good, but I don't really know. Like, it sounds
good when I tell people and it's almost like I'm performing for them with check out my
ambition. And instead I was like, what do I actually want? What do I actually want?
And I was like, let me zoom all the way back into today. Like what is a great day feel
like today? Forget what career, what my longterm plans and ambitions are like tomorrow. What
would make that day really enjoyable? Like what's an average day need to look like that
includes work. Cause I don't, I'm not satisfied if I just like do nothing like that's actually
pretty boring for me. Um, so I'm going to work, but what type of work is actually fun
to do on a day to day basis so that the day itself is the payoff, not I'm going to grind
it out and suffer for some future payoff. Um, that like, you know, may or may not ever
come. And I did that for like all of my twenties, you know, in my early twenties it was like
grind, suffer, sleep in the office. Um, future payoff, billionaire on the cover, you know,
Forbes 30 to 30, whatever the stupid goals I had was, that was like a way I thought about
things. And now I'm like, what does a perfect Tuesday look like? I was like, Oh, wake up.
I wake up without an alarm clock. That would be nice. Right. Uh, cool. Uh, opening part
of my calendar is clear. I maybe I'll just check in with kind of like the, I liked, I
don't want to work totally alone. I don't like that. Let me check in with my one business
partner early in the day. We kind of riff on what would make today great. Right. And
then I don't want to have a bunch of employees that I'm like managing and one-on-one I don't
want my calendar to look like that. I don't want my calendar to be a bunch of calls. And
so I really just zoomed in on what's a great day. And I realized in that process as a ma
I literally mapped out like a schedule of a great average day. And I, by the way, I
think everybody should do this. You should, you should map out a perfect Tuesday for you.
And it includes all the little things like, you know, I'm like, I realize it's like, dude,
one of the best parts of every day is like when I shower, I just, I love taking a shower.
It's just like, feels so good afterwards. I get a bunch of great ideas, really relaxing.
Um, I'm not on my phone. Like, you know, there's just like a bunch of benefits to it. I'm like,
okay, it sounds silly, but that's actually an important part of my day. All right. Walking
my dog. There's all these little things I enjoyed that I was like, I need to make sure
that happens. And the one most important one was I like just being curious and then letting
like following my curiosity. So I thought, well, how can I be professionally curious?
Can I get paid to be curious? Is that if that was my career, then what would happen? And
so that's where I started thinking, why, why not do something like a newsletter? Because
if I was going to do a newsletter about crypto, which is the thing I was most curious about
in those months, then I would get to just like, go read a bunch of stuff, go meet a
bunch of cool people, blah, blah, blah. And then cool. At the end of the night, I just
packaged that up into a newsletter that, you know, summarizes the most interesting things
I saw or I heard about. That seems like a fun project to work on. And that's how we
decided.
It's funny because this is like rich guy stuff. And I think it should be everybody's stuff.
Like I talked to people who are second time founders are third time founders and they're
saying the same stuff. Like, what would I like to do on a day to day basis? You know,
what makes me happy? And I talked to first time founders. I'm like, what is going to
make money? How do I quit my job? Like, I have no ideas like what will work, you know?
And I think that like, I'm interested kind of in the disparity between you, Sean and
you Ben, because it sounds like Ben, I don't know a ton about your backstory, but like
you're working on a business that wasn't working that well. And here, Sean is like already
like sold a company, like making all this money from his podcast, which is like humongous
investing. And I think when you have this dichotomy between like two different founders
who are in two different places, you might want different things. Like my boss is a billionaire
and he came to me at some point a couple of years ago. I was like, hey court, let's work
on this project together. And on one hand I was like, oh, this is a cool pet project
of his that he really wants to work on. But on the other hand, I'm like, he already has
like, you know, $10 billion and I have like some like infinitesimal fraction of that.
Like we have very different goals. So like Ben, like what was your, were you on like
this perfect Tuesday grind of like, you just want to have a newsletter that's going to
be fun for you?
Yeah, I definitely am a little more focused on like, yeah, I want to make a certain amount
of money, but it's not like my only goal. I'm like, yeah, I want to do it a specific
way and I want to have fun and I want to like chase the things that are interesting to me.
Whereas like, you know, for example, my little brother, he's like, he's like, oh, stuck in
the SMB Twitter world where he's like, oh, if I can start a housekeeping business tomorrow,
that makes me 10 grand a month, I'll do it. And I'm like, yeah, I definitely don't think
like that, but probably a little bit more than Sean is on the spectrum of like, yeah,
I want to do things that have an outcome. And I think Sean is slightly under, under
playing that because I think he cares too, but I think it's mostly like, there's many
ways to win. And like, there's a certain way that we try to win the game.
How do you win? Like Channing and I have a newsletter. It's not that big, you know, it's
like 125,000 people. We make $0 from it. Like we don't know how to win with the newsletter.
How do you win with the newsletter?
Yeah, I mean, I think the main things that I think we won with were one brand like, which
I think you guys do a good job with too. You know, we tried to stand out from the crowd.
I think there were, and I don't know, Sean, how you feel about this, but there was, you
know, we could have been called crypto daily or eat daily. Instead, we tried to pick something
that people really resonated with and we tried to build like a cult. And I think we saw that
on Twitter, a lot of people would resonate with the cult and the things that we did.
So I think that's one. I think too, we tried to write for ourselves. Like I think early
on we were like, Oh, who, who is this for? Is it for someone that's deeper or like our
moms? And like the reality was we were just like, let's just write what we like. And if
we like this, we're going to bet that thousands of other people will. And then three, I think
trying to get good at monetizing, which for us is we trained a kid from the Netherlands
to be really good at ad sales. I don't know, Sean, what else from your perspective do you
think we got right that helped us win?
Well, I think it's kind of two separate questions. One is what makes a newsletter work? What
does the newsletter business even look like? And then the second is things that we did
specific to milk road that, that actually like worked particularly well. And by the
way, I, I think what you did with indie hackers is exactly, uh, like that is the, that is
a winning formula. And yeah, it's not, you didn't do it through the newsletter, but you
did the same idea, which is you pick basically a niche that you understood that you could
speak to of people you like to be around. You built a brand around it with a cool name
and then you started figuring out what content they like on a regular basis, success stories,
uh, horror stories, um, you know, like tips and tricks, whatever. And you started providing
that to them on a consistent basis and whatever the outcome was, I doubt you could have predicted
that at the beginning. So even though I was kind of like a little bit on the hippie enlightened
path of like, what does my perfect day need to look like? Um, part of working on something
was like that this is going to succeed. It's going to be something that people like I like
and the market likes it, meaning it makes money and like, don't get me wrong. I love
money. My podcast called my first million for a reason. I really enjoy the sport of
making money. But what I realized along the way was I just looked at a pattern. Every
time I do something opportunistic cause I'm like, this will make money. My results are
worse than the things that I do because I'm like, this would be dope and this would be
dope happens to be a better starting point for me than this would work or this would
make money.
So this would be dope is like the first filter. Then secondly, do I see a path? Do I think
that there's a way for this to make a bunch of money or give me some other big benefit
that I'm interested in? Um, if so, then like green light go, go forward. And business is
like a skillset. So it's like, you know, I can go to my sister's preschool business and
help her make more money because there's just a skill of business about how to increase
revenue, how to, you know, decrease your costs or increase your margins, how to reinvest
that in a way that like grows the business, uh, how to structure your business in a way
that's like tax advantage.
Like there's all these like skills that go into a bucket when you're good at business.
So once I realized, Oh, you could just apply that to anything. I could take a podcast,
which is not typically something people make a lot of money with and I could find a way
to make a lot of money with it. For example, with our podcast, I think the first year we
made some tiny amount of ad revenue, 30 K, 70 K, something like that. But I realized
pretty quickly, Oh, ads is a really poor way to monetize a podcast. The better way to monetize
this podcast is like, look at what is this asset actually creating and then figure out
the best business model for that.
So what I realized was this podcast is attracting a bunch of entrepreneurs who either are already,
you know, somewhat successful or, you know, soon to be successful and they have really
high trust, right? It's not the biggest audience. It's not Mr. Beast, like 80 million people
watching a video, but it's now, I don't know, like 150,000 people. But back then it was
much smaller. Maybe let's say at that time, 30,000 people listening to an episode, but
they're listening to me with my voice for hours a week in their ears and they've learned
to trust me and like me and like hear stories.
And I'm like, I have this free avenue to build a whole reputation with them. And how do we
monetize that was we launched a fund and we just got like, you know, only the top hundred
or 200 wealthiest people in the audience to give us money. And now we invest $10 million
a year into startups. That turned out to be a way better business model. You know, investing
$10 million a year into startups using capital raised from the podcast listeners was a way
better business model than ads. But it's only because, you know, took something that I thought
would just be dope to do and then bet on myself that later I can figure out business model
that will work.
Is there any I'm curious. I mean, that's the some of the ways that you were able to kind
of parlay assets from your podcast into investing. Is there an extent to which you did anything
similar with the milk road and like, what's the equivalent crypto play is? Oh, man, these
people trust me and they'll do whatever we say, like, let's launch our own coin and then
get people to invest in that. But you didn't do that.
Yeah. Now, part of the important part of our trust is to not abuse it. So like, yeah, we
wanted to launch a fund if we thought that we could generate like alpha above just saying,
go buy ETH and go buy Bitcoin if you believe in crypto. Right. So it's like, do I believe
I can outperform ETH? No. So I'm not going to do that. Oh, cool. NFTs are hot. Should
we launch a milk road NFT? I don't know. We got a good brand. We've got a bunch of people
here. They'd probably buy it. Then what? Like, I'm not trying to sell you a door to nowhere.
So we couldn't figure out what the hell the purpose would be of the NFT. So we just never
did it at that time. And so, you know, part of the reason you can build trust is because
you know how to not abuse it. So we did. We didn't abuse it there. So what did what did
we actually do? We were like, well, we have a bunch of crypto readers who are interested
in crypto investing, things like that. And there was a bunch of advertisers who wanted
to advertise with us. So that that paid the bills on a month to month basis. So, you know,
I know you guys are indie hackers. You guys like numbers. We were doing, I don't know,
probably what was it been like between one and two million a year in revenue was kind
of like the rate we were at. Now we were in year one, we sold the business one year in.
So, you know, we kind of jettisoned a little early there, but it was working. The business
was profitable. It was doing, you know, seven figures of revenue. And more importantly,
we realized, OK, there are multiple ways you can parlay this audience in the future. What
we decided to do was say, let's use this as an excuse to learn and get smarter about crypto,
because getting smart and crypto can be a very financially lucrative thing for you.
Invest in projects that we're seeing early on. And we're able to get on the cap table
because when we go to the projects, we say, hey, can we invest in this? By the way, like
we can mention you in Milk Road and get you in front of a huge number of people. So we
provide some distribution, some initial launch users that you can't otherwise get. So we
did invest. We did learn. And now we'll see over the next five years if those startups
that we invested in turn out to be big winners or fizzle out.
Like did you share numbers about like how many subscribers you had? Like if you have
a newsletter in crypto and it's doing, you know, seven figures in revenue a year, like
how big does that newsletter have to be?
We didn't share that. But yeah, I think if you can get a newsletter, I think in general,
if you can get a newsletter to let's call it 100,000 to 150,000 subscribers, which is
I think where you guys said you're at, and you have high engagement. Do you have a high
open rate?
Yeah, we are at mid 30s, 30, 40 percent.
Great. So we were like 42, 43, something like that percent open rate. Now, the hard part
is we were every day we're here. So we're three times a week, which is I thought was
a lot. But you guys are daily, which is an insane way we do.
We did five now, six days a week. So but three is not bad. I thought you were going to say
once a week. So three is not bad either. My guess, you guys are you guys have you said
120 K subscribers? Yeah.
So let's say, I don't know, something like 50,000 people open every email you're sending
that three times a week. Ben, what's the math on that? What should they be generated? Let's
do this real quick. Live. So
yeah, I think our back of the envelope is like for every 50 K subs, you should be able
to make like fifteen hundred dollars a day in ads. So I think you should be able to sell
each ad for each day for like thirty five hundred.
Oh, that's a lot of money. I like the sound of that.
Yeah. Right now, we're selling you guys could be making something like between let's say
conservatively five K a week and aggressively ten K a week on your newsletter.
I love this free consulting, by the way. Yeah. Yeah. By the way, I actually think and now
I have a more updated view of this, which is that you should not sell ads on your newsletter.
You should figure out what what ad should go in the newsletter and then you should build
or own a piece of that right company. Wow. Yeah. Like Joe Rogan does. Right. He's like,
I'm going to make my own supplements and then advertise my own show on my show instead of
advertising somebody else's stuff on my show.
Yeah. He does both. But like and both is probably the like the actual optimal thing. So you
can like fill the full inventory. But I would just take the approach of if I'm going to
build this audience and I'm going to promote a product, I'm going to also own the majority
or at least significant stake in that product that will hold you true to two things. Number
one, you'll only promote stuff you actually like and believe in.
Number two, you'll only get you won't just try to grow your sub list to grow a top line
server. You will go for quality of reader and trust built with that reader because they
are going to actually be your customer. You're the one putting in the ad slot. So you need
them to be not just a bot. You need them to be like a real human being who's got income,
who trust you guys and has needs. And you can fill those needs with like some product.
This is all excellent advice. I'm taking notes. So I think the other part that I'm the most
curious about is just the growth part. Our newsletter has been kind of stalled around,
you know, like 125 K people and you guys grew your newsletter in record time from zero to
whatever it was, something that was worth selling. How do you grow a newsletter so fast?
Uh, yeah, there's a bunch of different ways. I think, uh, rain, you know, the best way
is your content is so good it gets forwarded or your content so good when you post it on
Twitter or other places, people click, they read, they subscribe. That's the best way.
So you basically blog your way, right? You do one off blogs and somebody says, that was
dope. I'd like some more of that please. And then you say, this button gives you more of
that on a regular basis. That's the best way to grow a newsletter. There are other ways,
you know, referrals and you know, word of mouth. So you build the referral program or
an ambassador program, things like that. You could do paid acquisition. So people do paid
acquisition. They, they buy by readers and it sort of goes like, as you would guess,
it sort of gets worse and worse the further down that spectrum you go, the further away
you go from, I post it, organically people see it, they read the content and they say
more please. Right. That's like the gold standard and the, the sort of like the worst is, you
know, the, the all time worst is you, I don't know, by, uh, Indian fake users. That's like
the worst. Right. So how do you grow a newsletter? You can choose where you want to live. I think
for you guys, the better case would be, you know, like how much traffic does like an indie
hackers get? Do you guys talk about that? Yeah, a couple million visits a month. Great.
So why are you not growing the newsletter faster from that? Right. Cause it was like
you mostly driving people to sign up for the community, sign up for the website, sign up
for the forum, which I think there's another piece that I actually want to get your opinion
on. I mean both of those, both of those opinion on, which is like kind of the secret to the
way that we run the newsletter as just a couple of people. We don't have a big staff. The
way that you run the entire website is we kind of leverage the power of crowdsourcing.
So right now we put out three newsletters a week. We have like a really talented like
New York times journalist who is our editor, but what she's doing is she is finding like
the best content that kind of fits a basic theme for our newsletter. Like, you know,
we've got three main stories. It's kind of a rip off in a lot of ways of the hustle.
It's got that kind of like magazine style. Um, but we don't directly control the content.
We don't like have like a staff of writers. So we're not writing them out. Exactly. So
like the, like what Ben said, like you're kind of building this cult, you have your
own voice. That's something that we don't necessarily have that much control over. That's
your opinion on this. Yeah. Curating works like a, my five tweet newsletter, right? So
I would do this thing five tweet Tuesday was basically like, Hey, I'm on Twitter all the
time. I see, see interesting stuff. Ben sees interesting stuff. This is Ben's super power
by the way. He's a great curator. Um, and we just show you like, yo, if you didn't want
to waste your time on social media this week, just read this email. It's five of the most
interesting tweets. One will make you laugh. Two will make you think, and one you'll disagree
with, but it'll force you to kind of like articulate your, your own thoughts in your
head. And that's kind of the, the core core format. And so that's a fully curated thing,
but it has a little bit of commentary from me in it. So it's like, here's the tweet,
here's my take, here's the tweet, here's my take. Um, and people love that email. That's
a good email, but it doesn't build the same level of trust or value as like, you know,
original content does. So it's, uh, you know, depends on the goal. I started that one because
I was like, look, I got this email list. I just don't want it to go stale. If I don't
send anything for eight months, this is worthless. If I have to write that original content,
I don't have the time right now. I'm running two businesses, so I can't do that. So I needed
something in the middle, something to just keep the list warm. And that was my, uh, my
solution. It's kind of like Tim Ferriss is like five bullet Friday or whatever, or it's
like, okay, I've got this huge audience in my podcast. People love me. I might as well
have like some very easy to curate newsletter. Exactly. Monetize. Exactly. The other thing
you do, Sean, like I think that's cool is like you've got your podcast, right? What
you talked about, which is huge and like feeds into this, how much work does it take you
to do your podcast? Because we are trying to get better at podcasting and like, this
is like, I don't know, like our sixth or seventh episode where Channing has joined me. Channing
is like at my college library right now or something. Where are you Channing? Are you,
did you use a comic? I am just a, I'm, I'm just a nerd. Like this is a, this is an Instagram.
This is, I read this article, my girlfriend sent this to me to like poke fun at me about
like how they're, how like a lot of like millionaires and like startup people are spending whatever
they'll spend like hundreds of thousands of dollars for someone to kind of like bus in
a podcast background library with like color coded books. But, but I'm, but I'm just a
nerd like this is just like, these are the books I've been toting around for. How many,
how many of those books have you read? Give me a percentage of books. I'm on, I'm on,
I'm on about 50%. I just got three books this like literally this morning I read a book
a week. Like it's just like a constant, constant thing. It's all Channing does. He just reads
every time I talk to this guy, he's telling me about a book he's read. All right. So I
don't know if you guys can see this all kind of all frame maybe, but I have these four
books on my bookshelf here for, um, how many, how many of those books have you read? Sean?
This book is called tango lessons. Uh, I don't even know if there's, Oh, there are words.
Why is that a book and not a YouTube video? Let's be honest. You could, you could go on
Etsy and you could buy, it's called cream colored books. And so you just buy these neutral
white looking books that look good. They look good on your shelf. And so, uh, that's the,
that was literally my book. So you did that. You did the, you did the, you did the books
in the background thing and you only got four and one of them is on tango. Are you trying
to learn how to tango or is that just like, no, I just read that for the first time. I
didn't even know what was on there. I just knew it was a cream colored book. I didn't
need, I didn't decide the designer was like, you need books to look sophisticated. And
so she sent me a link and I bought it. Um, so that's, you know, that's, that's how I
roll. But, uh, okay. So you're saying podcasting, uh, what's your question about podcasting?
You're a, we were talking last year, you're talking about how the all in podcast is billionaires
talking about billionaire shit. We're talking about your show. My first million is like
millionaires talking about millionaire shit. And the milk road is kind of the same, you
know, it's like Eddie become a millionaire with crypto. And then Andy hackers is kind
of like thousand errors talking, talking about thousand issues. We interviewed people making
like 10 grand a month and like that's, that's life changing. And on your podcast, you also
interviewed Peter levels. I think Sam brought him on your show and you're like, who's this
guy and like, why do we want to talk to him? You know, no, no, I'm a fan of Peter, but
he, uh, he did come on and he had one of the highest like rating episodes. He's got a huge,
he brings an audience. People, a lot of people want to know how to just be one, one guy and
just make it. But I remember Sam talking about like, why would you spend 60 hours a week
trying to make, you know, a hundred thousand dollars if you could spend 60 hours a week
trying to make a hundred million dollars, right? It's kind of like a very different
ethos. What do you, what do you two think about that?
I had the same bit of advice given to me. My dad told me that he goes, you know, uh,
this is when I was doing that restaurant idea, which is like the very first idea I had very
first business idea ever had was to create the Chipotle for sushi. So it's a stupid idea,
but I started winning business plan competition. So I thought it was the best idea ever. Now
my dad was like restaurants. Well, you know, son, not only do they always fail, even when
they succeed, they don't do very well. No, it's going to be huge. It's going to be a
chain. And he's like, okay, maybe. But he's like, you know, um, you're doing this deal
right now or like you're trying to put this one thing together and if it works, it'll
make $150,000. Uh, I'm doing this deal. He worked in the, he worked for BP, so he worked
in the energy industry and he's like, you know, there is no meeting for a deal that
has hundreds of thousands of dollars. Like there, there has to be an extra zero or two
for there to even be a deal. Like they don't deal in numbers less than that. And, um, he's
like a small project and a big project. If you, if you're working on them, we'll both
take up all your time. And I actually think that's very true. I think there's this big
misconception about like passive income. Very rarely do you find something that's truly
like passive income. Um, and most of the time if you want something to succeed, you're going
to put in, you know, pretty solid effort, pretty solid hours, unless you, until you
build up enough expertise that you can do something in three hours that takes somebody
else 30 hours to do, which does happen and now has happened for me in a couple of cases.
But at the beginning, you know, before, when you're pre-rich, when you're prefigured shit
out, um, you should just plan that whatever you're doing is going to take up all your
work time. And so you just are deciding, am I going to spend all that work time on something
small or something big? It's up to you. Um, the odds of success are not that dramatically
different. I would say maybe when you get to the category of I'm trying to build a billion
dollar company, the odds are, are somewhat different, but to build something that's going
to make millions of dollars versus hundreds of thousands of dollars or tens of thousands
of dollars, they're kind of the same likelihood of success. It's just, uh, you know, project
selection.
Okay. So let's get you on the record here. Uh, would you say officially right now that
you think that indie hackers is small boy stuff?
I think the way you guys are doing it is officially certified grade a small boy. Yes. Let me tell
you why you got bought by Stripe. Amazing. That's big boy stuff. It's been six, hold
on six, six years. And this is the phone that was out when you got, that's not even a phone.
That's like calculators. This is a blackberry. Uh, this is a, this is a small, this is how
I texted you. Congratulations when you got bought. How are you still flipping up the
top of the phone to like access the buttons? So, um, vesting out your full term and more,
I believe is small boy stuff. If you want to be an entrepreneur, cause basically what
you did, I don't know if you want to be an entrepreneur, maybe you don't. If you don't,
that's then it's not small boy stuff. If you said, no, I want to have like super chill,
I want to read five books a week and chill, like fantastic. Then you're doing, you're
living life on your terms. That is not small boy stuff. That is big boy stuff. But if you
wanted to be an indie hacker or you wanted to be an entrepreneur, the not doing entrepreneurship
for six years is probably not a good idea, right? Like, uh, you know, you don't just
like take off six years of your prime to not do it. So let's ask that question. Yeah. Do
you want to be an entrepreneur or do you want to have a really dope, fun lifestyle doing
something else? What is the goal? What's your role model? Peter levels is my role model.
He's one of the reasons that I started indie hackers and he's an entrepreneur, but like
more than anything, he just a creator. He tweeted something like people who are always
saying everything I do turns to gold. I've made millions of dollars. Like here's a list
of 96 projects I've made. Only four have made any money, right? He's just building shit
cause he likes to build shit. I'm kind of the same way, right? Like I left San Francisco
a couple of years ago. Sean, you and Sam talk about like this chat group that you're a part
of where it's everyone is like trying to blow up. I was in it. Yeah, I was in it. I was
like, you know, I'm not as excited about this shit as these guys are. Like you're all trying
to blow your Twitter accounts up to like a hundred thousand people. I'm like, I just
don't care. I mean, you get kicked out cause it sounds like it sounds like you're saying
you quit, but it sounds like, I think I got kicked out. He just, he just wouldn't, he
didn't talk to me. Not for me. Not for me. Right. Like I think there's a bug of just
like making more and more and more and more money that hits a lot of people and it's super
motivational. Right. But for me, it's like, I actually just like building stuff. Okay.
Okay. So you like building stuff. You want to be a creator now. Okay. Let's, let's go
on those terms. Last six years. How many things have you built and how many has Peter levels
built? If he's the, if he's the MJ of the, you know, the indie hacker, right? He was
the MJ of indie hackers. Let's say, um, are you Kobe or are you, I don't know if you're
an NBA fan, but like, you know, where are you? I'm like, I'm like that kid. He was at
my high school who was like, you know, second string on the basketball team, not wearing
all the gear, but all the gear, I got the Jordans, right. I'm practicing my jumps, but
I'm like, I'm not getting play time. But I think for me, it's like, we built some cool
shit. Like we have this huge directory of products at any hackers. We have this cool
community. Like I just want to be a builder. How about, how about you? Are you, are you
similarly minded? Is that your goal too? I mean, so we kind of have different trajectories.
The Cortland was doing startups and kind of had an aspiration to do startups, you know,
forever. I mean, he was lugging around like a, a bill Gates book when he was 13 years
old, he went to MIT, almost quit MIT to do a startups. Um, and I was like the old school
entrepreneur in a way that you don't make money, which is like, I just wanted to be
a novelist. Look at the books behind me. Right. You can kind of, you can kind of put this
together. And the way that I ended up going in this direction is, you know, I wrote a
novel, I got a literary agent, my agent was like, called me up on the phone and he's like,
Hey, I just want to let you know, you know, the, of the five bestselling authors that
I represent the like top bestselling one, he like works full time as a firefighter.
Uh, the second full time, like, yeah, it's like, he's like, he's like, just to be clear
like, these are the winners. Yeah. If you achieve all of your dreams, like you're going
to write like, you know, five hours on weekends. So at the exact same time, Cortland's like,
we lived, we lived in San Francisco together. I was like in this shitty sales job that I
was like, you know, this is going to be a dead end. I just got a call from my agent.
That's like, you're going to be doing that forever. And Cortland's like, well, if you
want to write and if you want to do that kind of a thing, like if that's your, your version
of being like kind of a billionaire, why don't you teach yourself how to code?
And so became a developer. I got tons of free time. And then Cortland started to hit a home
runs with the beginning of any hackers. And he was like, Hey, can you help me with, you
know, can you help me edit these interviews? Can you help me like reach out? Can you help
me build a forum? And it was like ticking off.
And now you're a millionaire. You can write as much as you want. I would say Channing
is someone who's living his perfect Tuesday every day. He's got a very strict regimen
knows exactly what he wants to do. And half of our conversations are about books he's
read. And the other half is about how much he loves his life because he's doing exactly
what he wants to do every single day.
You're like, bro, this phone call telling me how much you love your life. I can't get
this every day.
I'm a little jealous.
No, that actually has happened that you know, another thing I think is different in my life
that I've tried to build. I don't know if this counts, but it's like a circle of like
real friends. So Channing, you and I were talking about this the other day, like real
friends versus deal friends, right? I had like all my deal friends when I lived in San
Francisco, people that I would talk to, we would chime around with, we would work together,
you know, we would do deals together. And then I left SF and I realized like, I don't
talk to any of these people anymore. Was that a real friendship? And everyone says that
everyone loves on podcasts and say, I'm friends with so and so we're friends. But it's like,
we talk once a year about business. It's like that really a friendship? Or do you just get
like social status from saying that you're friends with that person? Whereas in Seattle,
like no one I know knows anything about startups. And we hang out and talk about totally unrelated
shit and like about our personal lives. And so I think for me, I've been focusing a lot
more on like making real friends, which I didn't have when I was in San Francisco.
Yeah. And very underrated too, because it's really hard to make friends as an adult. I
feel like friends was kind of like spoonfed to me, like when I'm in school or in college
or especially now with like remote work, it's like, man, even those like kind of like the
deal, even your deal friends are kind of gone. If you, if you don't go to an office every
day for a lot of people, right? Like they're not doing deals, they just, those are coworkers
and they kind of hang out together. And these aren't the people I would pick to be my friend,
but I see them every day. So, you know, why not? And so I think it's great that you actually
have that. And isn't that like one of the most commonly linked things to like happiness
is like basically having like a really strong community of like, you know, family and friends
basically soul searching last year. And that was like the answer to everything, your community
and like a sense of purpose. Those two things, if you got those, you're on the track to be
happy and if you don't you're probably screwed. But also like what you said was another common
thing that I heard in the tech industry that it's, it's hard to make friends as an adult.
And then when I came to Seattle, I started meeting people who'd sort of lived in Washington
their entire life and I would tell them the same thing. I, you know, it's so hard to make
friends as an adult and everyone just looked at me like I, like I had two heads. Like why,
why is it hard to make friends? They're like, I have a ton of friends. I've lived here my
whole life. I've got hundreds of friends. I've never left. And I thought about that
and ultimately like it's kind of easy, right? Like I've been doing it now too. You just
like when you meet somebody instead of only hanging out with them one on one, you introduce
them to all of your other friends. And then more importantly, when people invite you to
stuff, you just say yes and go out. You just go, right? It's actually not that hard.
Yeah. Tony Robbins has this thing. He says, he's like, people live this box life. He's
like, you sit in your house, which is a box, and then you stare. He's like, you go to work,
you get in your box that has wheels. You drive to your box building and you get in the box
there. You sit in your cubicle, that's another box. And then you type on your box and then
you get back, you eat your lunch box and then you go back and you get back in your box car.
You go back home to your box. You watch the box on your TV and then you go to sleep, right?
Like when you're hungry, you go to the box in your fridge and you just grab the first
thing you see and then that's it. And he's like, that's not right. Don't live this box
life. You should have some like variety and spice and twists and turns and some flexibility
with the way you live. And I think it's worth kind of like looking at, like zooming out.
You know, like when you take off in an airplane and everything starts to look like ants, it's
like you kind of just like third person, look at yourself and zoom out and be like, damn,
I am living kind of a box life. And like, maybe like I started doing this, I started
biking to work and it took me twice as long to get to work. And I was having three times
more fun. I was like, this is way better than what I was doing before, where I would take
this efficient Uber to work. And instead I started either walking, which took me 45 minutes
to walk to work, or I would bike to work. And it was like, even if it was cold and bitter
and terrible it was still better than the box life. And I think that there's like, there's
some wisdom in that.
I can relate to this a lot because I feel that the easiest way to get trapped in the
box is to really love the box, right? I feel like you love the box. I'm like, I've heard
you-
You're comfortable.
Yeah. Well, so it can be a kind of a comfort trap. And I mean, I don't know, I just think
back over 10 years of my life and it's like finding comfort zones and then occasionally
like getting riveted out of those comfort zones. Those were all the A, the like cool
stories in hindsight, but there were also all of these crazy learning opportunities
that gave me tools that I could then use to like break through in other areas, just to
be specific. For example, I had to get a job when I was in San Francisco. I'm not exactly
an introvert, but like I ended up getting this sales job and I was like, definitely
not looking for that. It was sort of hardcore copier sales, walking into buildings, not
fun work, but then I had to figure that out. And then the skills that I learned from that
in weird ways contributed to writing. I had a higher pain tolerance, right? It contributed
to just my personal, like my self concept of like, no, I can fucking learn anything,
et cetera. And a really interesting insight into how to break out of that box. I heard
from Sam on your show where he mentioned he has his four values that he figures out how
he can like kind of level up on whatever every year. And for him, it's fun, family, finance
and fitness. And like those different buckets, he just says, okay, what, what like, you know,
sort of fitness project? Do I want to like push my limits and get out of my comfort zone
on? Right. And just knowing that one little heuristic, he doesn't have to know in advance,
like what particular projects, like that's, that's still this mystery box, right? And
it's going to naturally lead him to go into these weird adventures. And I heard that and
I immediately ran to Cortland and was like, ah, it's sort of similar to my thing, right?
Because I've got, you know, connections, that's like connections, craftsmanship, contribution,
uh, in character. And it's like, it's, it's, yeah, it's just like easy to remember, but
I mean, it's, it's this thing that like in a way forces me to do random shit, character
cocaine.
You know, it's, it's actually a good point. A good bit of life advice is ask yourself
different questions. So if you ask yourself a question, most people, most people's quote,
the quality of questions they ask themselves are terrible. Most people's questions they
ask themselves are basically insults wrapped in a, in a question. So it's like, why do
I always do this? Or why can't I, why can't I find somebody? Why am I so blah, blah, blah.
So it's basically, those are the insults. That's like the worst type of question you
can ask yourself. The other bad trap, which a lot of successful people fall into is they
keep repeating the same questions that get them the results they're already getting.
So I call this the, the stressor achiever persona. It's basically, it's a person who
achieves things, they're stressed out the whole time and their life is like very narrow.
Like they're just really going on some track, some ladder. And that ladder first was go
to AP biology and AP English, and then get to the, get to the good school and get to
the good school, get to the good job and get to promotion, get to the manager. And then
even when they go to entrepreneurship and they're like, yeah, F the career ladder. Then
they're like, I raised my seed round, then my series A, then my series B. It's like,
you're just found a new ladder, bro. Like you're just, you're still ladder. You're still
on some track. And, um, not to say the tracks are all bad, but they lead you to just like
narrow your sense of what's possible and what the questions you ask yourself on a day to
day basis. So a question that I think is worth asking is what's the, what's something I'm
looking forward to a lot. What's something I'm really excited about in my life right
now? And when you ask this, it's surprising how hard it is to come up with this. It's
kind of disappointing how hard it is to come up with a good answer. The other disappointing
thing is if the thing you're saying, the thing you're excited about is like six months away,
it's like, wow, all right, that's a lot of hours between now and then, you know, like,
and can I pull the future forward? Can I pull some fun forward? And as soon as you ask yourself
that question, sure enough, you're like, well, I can just go do that tomorrow or I'm going
to fucking go to the zoo tomorrow, or I'm going to like, I'm going to call a friend
and we're going to go play some tennis. We're going to go do something and you will find
yourself pulling it forward. And so whichever area of your life you are like caring about,
like the family, the fitness, the fun, the finances, whatever it is, like, it's good
to think about what's a better question I can ask myself because most of life is just
a dialogue you're having with yourself. And rarely do we upgrade that dialogue. We have
the same old, same old conversations with ourselves. And like, if you change that, all
your actions then change. And I think that's like a really underrated thing that most people
don't do.
I think in that vein, one of the things you can do that's like pretty creative and will
get you thinking differently is to literally just impersonate other people when you're
asking yourself these questions. Like I'll do this with podcasters sometimes. We're like,
how would Lex Friedman ask this question, right? If he was talking to you, it'd be like,
oh, you know, Sean, like, what's the biggest source of love in your life, right? And he
was just, I would never think of that question, but like, he'll think of that, right? Next
question.
Or like, yeah, how would Patrick call us in like interview or Tyler Cowen or how would
you like ask a question? And I think there's just something that happens when you impersonate
somebody else that you instantly adopt an entirely new perspective on the world that
you just wouldn't naturally come to on your own.
Totally. I'll give you an example of that. We have a buddy, me and Ben have this buddy,
Suli, who's like, you know, one of our best friends, but also kind of like a business
mentor. So like on a personal level, we're really good friends. From a business point
of view, he's like a black belt and I consider myself like a blue belt or something like
that. So I'm like, I try to, you know, spar with him so I can see where I can improve.
And he helped us out a lot with the milk road. And I remember we had the conversation about
when to sell or should we sell? And it was like, Hey, it's kind of crazy to sell this
thing one year in when it's working. Like it's, uh, it'd be one thing if like this was
a bad business, but this is actually a good business and we're like, shouldn't we just
hold onto it? And it's like, he asked a bunch of questions that like, I've now hung out
with him enough that I already knew what he was going to ask. And therefore like I could
actually just simulate the whole conversation in my head and get to better clarity. And
um, I'll give you an example of some of the questions that he asked, but I, it's like,
I could have bet you $10. He was going to ask these questions, which is, you know, he
would point out that, well, if you're thinking about selling, there's a part of you that
wants to what, why, why do you want to, because you're saying it's a great business, blah,
blah, blah. Like, cool. And you, you wouldn't even consider this unless there was something
is, are they offering an outlandish price? Is there something, some risk you're worried
about? Is there, um, something else you want to go do? Like, what's the reason? And so
he asked that and that, that got me to get more clear. The other thing he said was, I
was like, yeah, we're just getting started with a lot. He goes, well, there is another
possibility, which is all the easy stuff is done and now comes the grind. And he's like,
so which is more true? Um, are you just getting going and like, now it's going to get easier
from here or did you take all the low hanging fruit and it's going to get a lot harder from
here. And, um, and again, like forget the, I asked these questions because for somebody
out there who's got their business and they're thinking about what to do with it, these are
really useful questions that are high level. These are black belt questions, not like beginner
questions. But the second thing is to your point, I kind of knew what he would say on
a bunch of the things that I was going to bring up. And it actually, what ends up happening
is I just start auditing and editing my sentence before it even comes out of my mouth because
I'm like, I know I can't get away with saying this bullshit around this guy because he sniffs
out bullshit. So let me just cut the bullshit out to begin with and not even say it. Um,
like you'll let yourself off the hook, but if you impersonate him, you know, he wouldn't
let you off the hook. He would never let me off the hook. Like this will happen often
with when I'm hitting a plateau or complaining about something. It's like, Oh, it's so hard
to do this. It's like, I know that he would be like, yeah, didn't these other five companies
do it? So like clearly it's doable. Like are they smarter than you or is there something
that's so unusual about your circumstances that you can't do that? Like, so then I'm
like, yeah, let's not waste the breath talking about how difficult something is when clearly
it's possible and I just need to spend my time thinking about possibilities instead
of thinking about woe is me.
So clearly you decided to sell, you went through that process and you successfully sold. So
like any high level or low level tactics that you have for selling and negotiating?
Yeah. I want to know about negotiation specifically. Channing and I just went through like a pretty
high level negotiation with like literally a dude who's bought and sold like 250 companies
at some of the biggest companies. And I think I would've gotten burned in that negotiation
if I hadn't already been burned kind of in like an earlier negotiation. Like I learned
some tactics. I'm like, I got to fucking do this next time. And like luckily they got
that result. Like how do you, how do you guys approach negotiation to try to like make as
much money as possible when you were selling the milk road?
Ben, I'll let you kind of give me, give him, give him your take on what your, cause this
was, I think your first big negotiation like this cause it, cause selling your company
I think is one of the highest stakes negotiations you're going to do, right? You've put years
of effort usually into the thing. Uh, it's your baby. You don't want it to fall apart.
You also want to don't leave a bunch of value on the table by agreeing too easily. Uh, you
don't get a lot of reps at doing this. So it's hard to get good because you do it. Never
done it before. If you're lucky once every few years, this was my second time doing it
was Ben's first. So Ben, I'll let you go. Then I'll give you kind of my take too. Yeah.
On the previous point too. Like I think when we were going back and forth with Suli, like
every three hours we would be like in a group chat, we'd be like, Oh, we should sell. And
then three hours later be like, no, we're not selling. I remember there was a specific
moment where he's, he was just like, what is your visceral reaction to selling? Yes
or no. Like just type yes or no immediately. And that's what you guys should do. And like
that I remember that he would see like our three dots typing. He's like, so what do you
want to do? Right? Simple question. So do you want, do you want to sell or keep running
the company? And then it'd be like our dot, dot, dot typing some essay with pros and cons.
And he's like, guys, you should just have a visceral reaction to the idea of selling
or not selling and like start with that. Then we'll go from there. We'll add analysis later.
And then I think, I think in terms of like negotiations, like, yeah, it was kind of my
first rodeo. I would say one, you know, at the beginning we were just kind of fishing
around to see what was possible. And then two, I think the main thing we did is we brought
more people to the, to the party. Uh, so like as soon as we knew someone was interested,
like I think first thing we did is we kind of set a rough number or a rough range in
our head where it would be kind of a doable deal. And then we went and we found three
or four more interested people to put them against each other, to talk, to kind of practice.
By the way, I should say that wasn't the initial instinct that I think most people have, which
is, it sounds obvious, right? It sounds like a normal, it sounds like a very obvious point,
but your instinct when someone's interested is to go deeper and date them. And instead
what you do is you actually stall them for a second. You're like, Oh, they're interested.
Great. Fucking ignore them and go get three more interesting people. Uh, because like
this will never work without that. Um, and you will never maximize unless you can go
get some more people to the table where I think the initial instinct is, Oh, they asked
us for this. Let's give them that document tomorrow. And then, then they want to meet
again and let's meet again. Let's get hot and heavy with this party real quick. Cause
Oh, they said all the right things and it sounds like it's going to work. And in actuality,
it's the time to immediately sprint on other options.
What, what prompted you to do the like counter instinctual thing then in this case,
Just experience like the same thing happened last time where I was like, Oh, okay. I understand
now how this works. And fundraising is the same way. Like, uh, you know, I realized that
these are auctions and uh, once you decide that you might sell, you need to run the auction,
but to run the auction, you need all the parties interested at the same time. Every time delay
costs you money. So that's where I was like, okay, now I know how to play this. And we
initially didn't plan for it. Like we were, we reached out to somebody basically being
like, Hey, can we advertise with you guys? You have a crypto audience on your website.
Like they might want to read our newsletter. Could we do like a swap or like, we'll pay
you a dollar for somebody that subscribes like what, you know, you're interested in
something like that. And they were like, no, but we actually really liked the milk road.
We would actually buy it. And then it was like, Oh, great, cool. Let me get back to
you. Uh, let me think about if we would want to do that. And then we had our conversations
and simultaneously booted up like, well, if we're going to talk to them, who else would
be the people that we would talk to you, make the hit list and start those conversations
ASAP.
Yeah. And I think the other thing that I thought was helpful is like one of the frames it's
really, I thought it was really easy to be like dreaming about how much money we were
going to make and be like, Oh, now I'm just dreaming and hoping that this happens. And
I think one of the frames that Sean really hit a lot was like, look, even if we don't
sell here, we're going to learn a lot about the business and how, like what people are
interested in, what they're not interested in, where we need to get better. So I think
try to like, we tried to embrace that, like, even if this deal doesn't happen and we want
it to, we're going to get a bunch of data points of things that people are curious about.
So like if we come back in a year or two, we're going to be way stronger for these reasons.
Yeah. That's a really, really important one. Another thing that Suli had taught me, he
had done this with his business. He's like, had this beautiful rosy picture of his business.
I was like, Oh, of course somebody will want to buy this. And he went and he tried to sell
it himself. And immediately the market's like, at first they're like, wow, great business
would love to learn more. And as they learn more, they're like, ah, this and that, and
Oh, you only do this. Like, have you thought about this? And it's like, why do they keep
talking about those three things? They're missing the big idea, the big, the good parts.
It's like, actually, those are what's important to them as a buyer. And you, if you do that
with enough people, you get a real objective opinion about what your business is worth,
where it is strong, why the, why they value it at anything, um, and where it's weak. And
then you're like, Oh, okay. You know, like let's take a newsletter, for example. Oh,
you value this on, are they valuing this on profits revenues, or do they look at the subscriber
engagement and then assign a value per subscriber? Um, Oh, interesting. Once I know how they
think about this and what they're worried about, then I know if I was going to sell
this 12 months or 24 months from now, that gives me a blueprint. That gives me a roadmap
of how to make my business a lot stronger and more valuable to the objective person.
So that's one component to it is learning that that's true. And then the other is this
great quote that after we got acquired by, um, by my previous company got acquired by
Twitch. Um, Emmett, who's the CEO of Twitch and the co-founder of Twitch. He, he has this
great phrase that he learned from Paul Graham from, from Y Combinator. He goes, he goes,
what is he goes, birds fly, fish swim and deals fall through. And so that's the other,
like he, anytime someone would come to the table and be like, super proud, like, Oh,
we had this great meeting. They're super interested. And then they start forecasting all this stuff.
He's like, great, just know birds fly, fish swim and deals fall through. And then he would
say that, and you can see they're like, okay, buzzkill. Sure enough. Uh, it's, it gets even
better. We get the term sheet or get the, get the contract. Oh yeah, we're just working
on the last few details. Sure enough, deal falls through. And the same thing happened
in our acquisition process, which was first of all, uh, we had to go in with this mentality
that most likely don't start dreaming about all the shit you're going to buy. Uh, most
likely there's no deal to be had. Let's go in with that understanding that that is the
likely scenario. And, um, that means two things. Don't check out of running the business and
start imagining a world where you don't have to work and don't have to do hard things.
And secondly, don't like count on these coming through that way you're emotionally detached
and can actually not be desperate when it comes to, to the negotiations because a negotiation
will go in the favor of whoever has more leverage. And the, the, the thing that nukes all like
logical leverage is your emotions. If your emotions are desperate to buy or desperate
to sell, you have lost all your leverage in that one emotional swing. So you have to be
emotionally detached.
I mean, there's a similarity between the acquisitions of indie hackers and milk road, it sounds
like, and that like, you know, this wasn't just like a project of like, Hey, let's go
try to get acquired. You said you were reaching out about advertising and then like this other
avenue opened up. And I wonder if that ads or if that like sort of enhances your, a little
bit of your emotional attachment because like the roadmap that was, you know, sort of in
your head before that was like, you probably knew what the next six, 12, 18 months probably
were going to look like. Whereas if you're like, you know, this is kind of a fire sale
or something, you know, we, we really want to get out for whatever reason. It seems that
you're a little bit more desperate. It's something that you're, you're explicitly looking for.
You're going to be way more better to not need to sell. Right. Yeah. Always better.
And there's really three to three buckets. You could be in, you could be Instagram and
it's like, yeah, we're the next big thing and everybody wants us. You have a very different
negotiation style, practice and outcome. Then there was like where we were with milk road,
which is we have a good business that we like, we don't have to sell it, but if the deal
was right, price was right, partners were right. People were right. Then we'll do it.
And then there's the shit's not working. What can I do to like, you know, scrap some value
out of this for myself, my investors, for my sanity, for whatever else, right. To land
the plane because the engine's on fire and just be honest with yourself, which category
are you in? And once you know which category you're in, you have like a slightly different
tactic and I've done the second and third before and I've never done the first. But
I don't think it takes much skill to do the first. When you're the first one, you hire
a banker and you need to run the process. Like it's just, it's straightforward. Yeah.
You know, you pick the highest number. Yeah. Everyone's coming inbound and everyone's outbidding
each other because you have the in demand hot thing. But I wanted to say one more thing
about deals falling through because I think this is really important, which was we got
to a point where we had two offers that side by side were about equal. One was a bit better.
And one had been like a lot more thorough and diligent and like, you know, lots of conversations,
lots of questions, lots of sessions, you know, talking through different problems, whatever.
And the other one was still a little bit earlier in the conversation. And we had a conversation
with, I think, I forgot who it was, Bology. I think I called Bology and I was like, yo,
what would you do with this? And he said something really smart. He goes, I gave him the information
with the offers, but I didn't tell him how they were on slightly different timelines.
One was more mature than the other. And when I said that at the end, he goes, oh, forget
everything I just said. He goes, most deals will fall apart twice before they happen.
This other one you're telling me has almost, you know, you've both walked away twice already.
And so this is a real offer and it's a serious offer and will likely close. This other one
is you're still in your honeymoon phase. You haven't walked away yet. They haven't kicked
the tires in the most serious way yet. You need to discount that by maybe 50 to 90 percent.
He's like, so you thought these were close. They're not close. And he turned out to be
completely correct in that analysis. And so I would say the two takeaways for somebody
who's trying to sell their business is the rule of two, you're going to break up twice
before you before you end up getting married, most likely. I don't know if that happened
for you guys, but it's very, very common to sort of like feel like there's no deal happening
twice, either because of a legal reason or a finance number or some other holdup that
pops up. And then also, if you're in the case where one deal has actually gone through that
process and gone through the fire a little bit, gone through the diligence and the other
one hasn't, you have to apply a pretty aggressive discount factor to all the terms. We we had
like the exceptional story where like the day between stripes saying, hey, we want to
buy any hackers. And that's like having agreed to numbers and have attorneys like drafting
a paperwork was like four days. It was like, wow, boom, wham bam. And then and like a later
negotiation that I've gone through, it was what you're talking about, like two, three
months of like tense conversations. This might not happen. Prepare for the worst case scenario
before things like concluded. I think that's like that's why I know I did the first one
wrong conversations about like, oh, we could just walk away like just like feeling that
heat. What we didn't feel in the original. Yeah. Yeah. They said that you should push
hard enough or like it might not work. Otherwise, you're giving up too easy.
Yeah. You haven't found the line yet. You haven't found their actual line and they haven't
found yours. Exactly. Yeah. The other two things that I thought were interesting is
I think we at least I learned in this, like we would ask for something from the guys we
ended up working with and they would just say no. And I was like, oh, wow, they're pushing
back pretty aggressively and we're still interested. So, you know, there are ways to push back
and not turn the other party off. And then, too, I thought it was destiny when they invited
us to dinner and it was the same restaurant that Sean went to when he closed his Twitch
deal. I was like, oh, this is happening. Wow. Sean was up. I didn't know that. No,
both in both cases. It's the other party who said, come, let's meet here. And it just happened
to be the same restaurant in San Francisco both times. It was kind of crazy.
Well, listen, guys, you've taken up a lot of your time. Thanks a ton for coming on the
show. Shane, the story of the Milk Road. Where can people go to find out, you know, what's
next for you guys? What are you guys working on? Where should people go?
Yeah. So we're brewing something up that I think is going to be pretty fun. And I think
right now the place to do that is to go subscribe to the newsletter. I actually want to publish
a lot more about the Milk Road story. So the origins, the how we grew it, the how we sold
it story. So I'm going to publish that if you just go to just go to Seanpuri.com. So
it's S-H-A-A-N-P-U-R-I. So I don't know if you guys put that in the description or something.
Just go there, put your email in. And that's where we're going to send that. And me and
Ben are going to start putting out a bunch more kind of amazing content. Like I'm basically
going to not start another business. I'm just going to put out incredible content for the
next like edit a few years.
Ben, what about you? Where are you at?
I'm on Sean's list too, but I've been guest posting. I wrote my first one last week. And
you can follow me on Twitter, Ben M. Levy. I need to get rid of that M. I need to make
my Twitter handle better. For now, Ben M. Levy.
Who's got Ben Levy? Who is this guy?
All right. Thanks, guys.
Awesome.
We'll see you in the next one.