What's up, everybody? This is Cortland from IndieHackers.com, and you're listening to
the IndieHackers podcast. More people than ever are building cool stuff online and making
a lot of money in the process. And on this show, I sit down with these IndieHackers to
discuss the ideas, the opportunities, and the strategies they're taking advantage of
so the rest of us can do the same. Today, I'm talking to Rob Walling. Rob has
been on the show plenty of times before. He is the founder of MicroConf, the best conference
for bootstrapped founders. He's the founder of Tiny Seed, where he invests and bootstrapped
founders. And he was also the founder of Drip, an email marketing tool that he sold for millions
of dollars. Finally, Rob is the host of a great podcast called Startups for the Rest
of Us. I recommend checking it out if you haven't yet. We actually recorded this interview
on his show, and I'm cross-posting it here for all of you to listen to. Enjoy.
I'm Rob Walling. You're Cortland Allen. We're putting this on both of our feeds. I can't
just do the Startups for the Rest of Us intro because people will be like, wait a minute,
this is on the IndieHackers feed. So I think we're coming out a day apart, but I'm excited
to sit down with you, man. Me too. You're always one of my favorite people to chat with
and podcast forum in real life too. And I feel like you asked the question on Twitter,
what should we talk about? And we got a million different answers. A lot of things. We got
a list of stuff we want to talk about, and so maybe we'll go along this time.
I think we can. I'm excited about it. Likewise too. I appreciate the compliment. I certainly
feel the same way. I really look forward to you and I sitting down because I feel like
we have enough shared views and enough shared world views of bootstrapping and indie hacking
that it makes sense, but the overlap's not a complete circle, like a Venn diagram. That's
just a circle. And so I always feel like I learn from you and I expand my thinking when
we talk.
Yeah. It's funny you say that. I listened to your
episode on My First Million, and I think near the end of the episode, you were giving startup
ideas and Sam Parr, I think was the one hosting that particular one. And he's a funny guy
because he's so disagreeable. No matter what you say, he'll just come out and be like,
I think this is absolutely untrue to say the exact opposite. And he's not afraid of looking
dumb and being wrong or whatever. And that is really entertaining, but I think you and
I agree on a lot. So we probably won't have that kind of talk, but agreement is also cool.
Oh yes, we will. Because I'm going to make me disagree with everything you said just
to do it. So well, the first thing I'm going to say is I just made an offer to a producer
who's going to really be heading up all the back office stuff for startups of the rest
of us, the micro comp podcast, micro comp YouTube. I want to define it. I mean, in total
inside baseball from one podcaster to another, but do you still do a lot of the work? I know
I don't imagine you do audio editing, but like, are you scheduling guests and putting
stuff into WordPress writing show notes? Or have you been able to like get that stuff
off your plate off my plate? That's the best hire I've ever made was I call her my podcast
boss. She was the producer for Mixergy. She still is a producer for Mixergy, but she does
the Andy hackers podcast now. And I just like have her do literally everything that you
possibly can that I don't feel like I need to be involved in. And so I like kind of being
involved in the guest selection. Who's going to come on? Who do I want to talk to you?
Because if like someone else is choosing who I talk to you, then like, I don't know, maybe
I could outsource that. But right now, like I, I like choosing, I want to talk to you
and I like sort of helping prepare. But what's cool about RA is I have her come on and even
these things that I want to do, like we'll be on a zoom call where she's sitting there
watching me work and offering suggestions. And so I'm not even like doing that alone.
She's kind of like podcast boss. She holds my feet to the fire. She makes sure I work
on it a few hours a week and she gives me like helpful feedback while I'm working on
it. And then I sit down, press record, talk to my guest, press stop at the end of the
conversation. We chat a little bit and then I do nothing else. I don't title the episode.
I don't describe the episode. I don't tweet about it. I don't release it. I'm on to the
next thing. And it's such a breath of fresh air because I think a lot of podcasts, you
know, people churn. Most podcasts don't last for much longer than a few episodes. And I
think it's because people get bogged down by all this extra work that they don't really
enjoy as much as they enjoy the conversations themselves.
Right. That's awesome, man. Well, I'm happy for you and I'm happy for me that next week
that I'll be in a similar situation. I mean, to be fair, I'm probably 75 or 80% of the
way to where you are, but I've just piecemealed it together with like a part-time freelancer
who does the show notes in a part-time, you know, an editor who does this and that. And
then there's some gaps there. There's always some gaps and I am the fallback, you know?
And with MarkerConf stuff, Zander, Producer Zander is a fallback. And so we're bringing
someone in to really backstop that. Finally, I mean, it should have been done last year
or years ago, to be honest, but it's just one of those things that you get, you do the
same thing for too long and you don't think about how it should change.
Right. You get used to it and kind of assume. And it's stressful being like, like you said,
there's these gaps. It's stressful having to be the glue that sort of glues all these
things together to fill the gaps because then it's like, it's almost in a way as if like
everything is a gap. Like you still have to worry about every single thing, every single
part of the process. And it's also stressful to like hire somebody and just trust them
to do everything. Yeah. Because like, they're not going to be as good at you as you at some
things. They're not going to have your particular eye for certain things. But the cool thing
is that they'll be good at stuff that you aren't good at if you make a good hire and
they'll improve your show in ways that you didn't really anticipate. And so I think a
lot of it is just learning to let go and have someone else do those things for you and see
what comes out and, you know, go with it. Yep. Yeah. And I've always been able to let
go, like when building SaaS companies, it's like, I can let go of customer support. I
was able to let go of software development. I can let go of customer success and sales
on and on and on. Letting go of like creative stuff for me, like writing and, and podcasting.
And that stuff's a lot harder for me, you know, cause it's like, there's so much subtlety
to it. It's less of a, less of a, here's a job description. It's more like you kind of
just got to do it, you know, and make it, make it good. And that's hard, right? There's
a, as a popular indie hacker, I won't say who it is. He has more than 40,000 followers
on Twitter and his Twitter account is entirely automated. He never tweets. He doesn't even
know what he's tweeting. There's a team of people who tweet for him and his Twitter
accounts fire. It's awesome. He tweets several times a day. People engage. Some of the tweets
are really personal, but he is like the ultimate in like being comfortable, I guess, letting
go of the creative element. I can't imagine doing that need either. That's awesome though.
I wanted to ask you, so indie hackers went invite only. Is that right? About five, six
months ago, five, six months ago. Yeah. I don't know if you've talked about that publicly,
but I'm just wondering like what was around that decision. And is that like, just, does
that just come with growth of a community? It was like, I mean, it was very simple. Spam
was out of control and I have been fighting in spammers from like day two of the forum
for like five years and they're so good. They're not just like people making little bots. Like
they are actual human beings sitting in offices somewhere on the other side of the world,
like getting paid to spam websites and not caring at all. And if you put up obstacles,
they will figure out what the obstacle is and try to get around it. And at some point
last summer, like I think we had like six or seven thousand people join and the hackers
and like 2000 of them were spammers. And I was like, this is a battle that I'm losing.
And I just want to go back to basics. I'm not obsessed with growth at all costs. Like
we don't need to have, you know, thousands of people joining every week. We can just
go invite only mode completely cut out the spammers and have the community sort of returned
to some level of normal normalcy. And I like the idea of an invite tree where you can see
every single person who they were invited by, who that person was invited by, who that
person was invited by, because then you start to build sort of like a sort of a clear picture
of, OK, this guy's a spammer. How do they get invited? Oh, all these other accounts
are spammers, too. And so we left it on invite only mode for, you know, the better half of
last year. And I'm pretty sure we've rooted out like literally 100 percent of the spammers.
Six months ago, when people complained about spam and any hackers, they were complaining
about like people posting escort ads and flag or pills ads today when people complain about
spam and any hackers just saying, oh, this person made a post that I didn't like, which
is a huge improvement. Yeah, that's a trip. So I never, I mean, I'm on indie hackers
relatively frequently and I never saw the spam. Was it just getting ripped out before
I saw it or what was it? Yeah. I mean, so what what time zone are you in here in the
United States? Central time. Yeah. OK. So if you were like in Europe, you saw a lot
of spam. So what happened is we would go to sleep. Our community manager would go to sleep
before and be overrun with spam. Or if like, depending on your browsing habits, if you
go to any hackers dot com slash newest and you just see like a fire hose of posts, a
lot of that was just spam. And most people don't go there. But like the people who do
go there, the people who want to curate the community and have, you know, some sort of
control over what makes it to the front page by uploading stuff. And like they were just
deluged of spam. And that sucks because if they can't go there and get a good experience,
you're not going to go there, which means no one's sort of giving us the signals we
need an uploading post to figure out what should go to the homepage. That's a problem.
A big you know, one of the things I was most frustrated with running drip was the the spammer
slash people who would hack not hacking, but they'd sign up for an account. They do phishing
attacks on it. Right. Or they would or they would send shady emails and get us on blacklist.
Like it was such a headache. And we had all these checks in. We had this code that would
validate. It was like credit card versus some actions in the app. I mean, you could call
it these days if we were raising funding, we would call it an AI thing. But it was just
it was just code that measured. We could detect patterns and behaviors. I hated it. And it
was one of the things that was when it was a smaller factor. But I remember being like,
I could see selling this company purely be on the worst days of those. Like when Derek
and I went to sleep and then at Sunday, you know, it was this Monday morning at 2 a.m.
and then like Russian basically spammers like created a bunch of accounts and a bunch of
phishing stuff. And I thought I could sell this company. That was early on, you know,
you're like 20 km or so that wasn't it. But did it do that for you? Did it did it ever
feel like, you know what, I could I could rage quit this thing up in here because of
this. Yeah, I never got quite to the point like I would quit because of this, but it's
super demoralizing because it's like the number one thing I think thing I think about every
day is like, how do I improve the community? How do I like promote the people who are doing
like a genuine, authentic job of contributing great content and stories? And then you have
these other people who just cause you to lose your faith in humanity. Just like total assholes
like sociopathic. They just don't care. You're trying to build a good thing. They're just
trying to ruin it. They're not even trying to ruin it. They're just trying to promote
their own thing. They don't care that it's going to ruin your thing. And I talked to
so many people who dealt with this problem and I was like famously at PayPal, you know,
they're like sending money over the Internet and a huge percentage of what they needed
to do to make that business work was get really smart at fighting fraudsters. And that was
super hard for them to do. And they had a super talented team to do it. I talked to
Amjad Massad at Repollet. So it's like an online sort of code editing tool and code
education tool. And it's like what are people he's repollet for? Building sorts of like
crypto bots to mine crypto using his server's bandwidth and costing the company a whole
bunch of money and they just don't care if they're going to ruin Repollet's business
if they can make a few thousand dollars. Time and time again, I talked to people who have
this issue where you just like deal with the worst people. So the Internet's cool because
you can reach everybody. You can reach all the good people, but you also end up on the
radar and straight in the crosshairs of sort of the bad people who don't care.
Yeah, when you get any modicum of success, I mean, we have tiny seed companies who by
the time they hit 20K MRR, 25K, so it's still relatively small. They are, if they send any
type of email, if there's any type of email sending capability, like people start targeting
them in terms of I'm going to do a phishing attack, I'm going to do a spam attack, I'm
going to send unsolicited email based on your good IPs.
This doesn't happen in real life as much. If you have like an events business or like
a store, you don't get people who come into your store and just yelling loudly to advertise
their product. You just don't deal with that many shoplifters and stuff. There's not as
many assholes when you can see people face to face. You can look the owner in the eyes
and see that it's a human. You're like, I don't want to ruin this person's business.
But online, people are just kind of assholes. They kind of default to like, everything's
a faceless corporation. If I can take advantage of them, I'll do it.
That's right. The anonymity is a real problem, is that they can remain anonymous. I mean,
we've seen that with online forums. It's like Facebook, I know people get out of control
too, but at least usually a real name is attached to it versus YouTube comments, even Reddit
to a certain degree. I think there's a big, big case to be made there.
Yep. But indie hackers is no longer invite only as of three weeks ago. So it is, anybody
can join. And now we have a whole process. A lot of it's manual where we'll like sort
of look at like your contributions. So when you join, you can't make a post, but you can
make comments. You can sort of help other people out in the community and contribute
and discuss and upvote comments. And essentially if you earn your way out of that sort of second
class citizenship, shall we call it, you'll get a little email from me and we'll promote
you and you can now be like a fully fledged member of the community.
And every now and then we'll just promote somebody. Like, you know, if we do an AMA
with somebody, we'll just kick them right up to a full fledged member because that's
somebody that we know and trust, but everybody else has to go through this process. And it's
really good at weeding out like who wants to be an authentic member of the community
and who wants to just do like a drive by, Hey, I'm launching my product today. Can you
give me access so I can launch today and then, you know, disappear and go somewhere else.
And it's, it's really funny to me like how people will literally ask to do that. Like
I get emails every, every day like, Hey, you know, I'm launching today. I haven't put any
work or effort into the community. Can you just whitelist me so I can do my drive by post?
Crazy.
Even when we got rid of the spam with the invite codes, I got DMS on Twitter from spammers
or like, Hey, I'm trying to post my Viagra pills thing and I can't get in. Like, am I
going to invite code? I'm like, are you kidding me? Why would you ask me this?
Yeah, it's crazy. It's like they think you're a customer service rep who just doesn't know
any better, you know, who's going to send that. That's such a trip, man. We had similarly,
it's off, you know, odd that a forum spam or four, we have forum spammers, community
spammers and email spammers are similar because we built up a thing. We architected it out
and we never got to build it, but it was a trust score. And it was like, when you first
signed up for drip, your trust score was like zero. And then depending on what you did and
your open rates and your click rates and what your credit card was prepaid or not, there
were all these factors. They were like 10 factors. Over time, that score would go up
or it would go down. And so if you had, you know, you got a bunch of spam complaints or
you got low open rates, like we would start to knock that down. And when you got below
a certain threshold, we'd block sending on your account. And when you obviously, you
know, you built it up over time. I think if you had a bunch of sends that went great,
you get up to 10 2030 or whatever. And so it sounds like you figured out a nice, perhaps
easy way to kind of hack that same thing with any hackers. You basically get a little score.
You don't see your score, but like, okay, below a certain score. I don't even look at
your comments and stuff above a certain score. Like admins can kind of like, we have some
moderators and stuff. You can kind of see, okay, here are the people this week who've
reached this score here, their comments, like who should we promote until a fully fledged
member? And it's, it's funny because like, you know, there's a whole black mirror episode
on this. It's like very dystopian when this woman has seen it. Everyone in society has
a little score and people can constantly score you. And she just has like the worst day ever
and gets like a negative score. And now she's like an outcast and she can't get an apartment
and can't get invited to parties. But I think in reality, it's not, it's not so bleak. It's
usually pretty useful and it makes the community better for everybody for there to be the score
that's invisible because so long as it's responsible and it can't be like gamed to like ruin a
perfectly good person's time. Uh, it works. Yep. Yep. I agree. So I sent a tweet out,
I found some pictures from microconf 2011. It was the very first microconf. And so this
is like 11 years ago. And I posted a picture of like, it's like Andrew Warner taking the
stage for the first ever talk and first ever microconf. And he looks, we all look super
young. I mean, cause it's 11 years ago. And so Andrew Warner, and then there's like me
and Mike Tabor and, uh, Ramit and Heaton Shaw and, you know, there's the Texan guys are
Sean Ellis and Heaton Shaw. So there's, there's just a handful of pics. It got me thinking
though, as I look back, I was like, man, we were really young and we didn't know what
kind of what we were doing. And here I am still doing, I was doing the podcast then.
Yeah. I was still, I was talking about startups. I was running events and I'm still doing those
things. And it caught me thinking, I don't often try to look out five, 10, 15 years.
Cause it's just so far in the future. But I'm wondering if you, if you have, you know,
do you ever think like, what am I going to be doing in a decade? Am I still going to
be doing something similar related to this? Or do I think I'm going to, you know, this,
I'll have a time doing this and maybe switch it up.
I live in the future, man. I'm like, I think way too much about the future. This is a good
book. It's called the time paradox where they talk about how a lot of our decision-making
and life comes down to sort of the default timeframe that we live in. And some people
sort of default to the past. Some people default to the present in certain situations. And
like, I think probably most tech founders and entrepreneurs are like very future focused
people, which I think correlates highly with like success because we're often thinking,
you know, what can I do now to get to this desired state five or 10 years from now? And
like that turns out to be a really good way to plan and strategize, but it's also not
the best way to sort of enjoy life in the present. And so, you know, I remember being
in school and going to MIT and thinking at the end of our sort of four years in our fraternity,
everybody could get up and you could just talk and give a speech and you could say whatever
you want. It was an awesome tradition because it's like, you just got 40 years to think
about what you're going to say and you get up and you talk. And one of the cool things
about it was everybody felt so lucky to go to that school. People would sort of default
assume that you were smart and give you the benefit of the doubt. But I thought a lot
about it and it's like, none of us are here because of who we are now. Like we're here
because of decisions we made when we were like 12 years old. We were like 13 years old,
like I'm going to take school seriously and I'm going to study for the SAT. And like now
10 years later, that's paying off. And that's something that never really, it's a lesson
that never really left me. You know, like the decisions you make now change your life
dramatically five, 10 years in the future. And so I hope that 10 years from now I'm still
working on Eddie hackers. If I'm working on any hackers 10 years from now, that means
any hackers is in an amazing place that I'm probably super jazzed about where it's way
bigger and more impactful than it is now. And if I'm not working on any hackers 10 years
from now, it doesn't necessarily mean it's a failure, but it definitely means I moved
on to something else that was more exciting. And it's not really my plan right now. Like
my plan right now is to try to build any hackers into like an institution, you know, something
that like really touches a ton of lives in a really positive way. And I think it already
does, but I think if you build a good thing, like bringing it to more people is an even
better thing. You know, if you build like a really cool tool or really cool, like, I
don't know, like, you know, sandwich sandwich shop and you can like franchise it. And now
more people in the world can eat that sandwich. Like that's a good thing. If you invent pen
a selling, you know, it's a hundred times better if you bring it to a hundred times
more people. And like, I've been trying to make any hackers a good thing and I want it
to bring it to, you know, thousands of times more people. And that might take five or 10
years. Yeah. Yeah. That's a, it's interesting you say that because obviously you and I've
both been doing this now for years, um, talking to, talking to and trying to help aspiring
and, and actual founders, I guess we're all actual founders, but founders who have actually
shipped in, you know, who are just working on it and want to do it. Yeah. And it wasn't
until the last couple of years really as like, I have this podcast, I have microconf and
now we're going to launch tiny seed out of it. And I started thinking like, what is the,
I think I'm, I think we're grown up enough that I need a mission. You know what I mean?
Like, what is the mission? And I've been honing it and refining it. And I still, I still struggle
with exact wording, but like the mission, I threw it out, uh, you know, I tossed it
to producer Zander. I showed A&R and Tracy and I was like, I think the mission, what's
interesting is the mission of all three of those properties is the same thing. The mission
of tiny seed, microconf and startups, the rest of us, it's all the same. It's to, it's to
dramatically multiply the number of self-sustaining independent startups in the world, you know,
and whether the wording exactly is it SaaS startups, is it this, but that's, I just want
there to be more and I want them to be self-sustaining. So look, maybe they took funding, maybe they
didn't, I don't give a shit. And in fact, I never have it. So, you know, I just don't
want the dogma, but so, so what's interesting is once I said that mission, I was like, wait
a minute. I've been doing that for like 16 years. I think more than that 17. So 2005
is when I started blogging about this and it's like, I didn't have that mission in mind,
but that is what I want to do now for me for the rest of my life. Like that's it. But for
the rest of my professional career, I'm sure I think I'll be working till I'm basically
keel over dead. But that was an interesting umbrella term for me to realize, you know
what, I don't need, I enjoy podcasting and I'm going to keep doing it, but I don't need
to podcast if I'm still doing something that follows that mission, right? And I don't need
to have an online community, you know, and I don't need to have a fund, but I think I
will be doing something under that umbrella forever.
I think that's a great, a great sort of vision. You know, like one of my heroes is Charlie
Munger. He has like a lot of writing and business advice that influenced me, just life advice
and ways to think that influenced me when I was younger. Dude is 98 years old. You know,
we did last year, like a podcast where he's distilling investment advice and talking about
how he's running Berkshire Hathaway with Warren Buffett. You know, he's 98. He's found what
he loves. He's, it's, I don't know, kept him healthy and mentally super sharp, just as
engaged as ever. I think that's a great goal. And I think, you know, your mission for microconf
is kind of like, not just microconf, but like everything you do, Tiny Seed as well. It's
kind of the same as mine. You know, I want more people to become financially independent
and free to live the lives that they want to live. You know, and I think that starting
online businesses is one of the best ways to do it. It's increasingly becoming accessible
and a good way for people to do it. And it's fucking encouraging to see everyone doing
it. And so like, that's my mission too. And you know, I was reading some, some research,
my buddy Julian turned me onto this researcher. Her name is Aaron Westgate. And she published
his paper about different types of lives that people can live that are good. And so there's
kind of this idea of like the happy life. And a happy life is characterized by, you
know, it's kind of the most obvious life that people want, like a life full of comfort and
joy, security, free time, you know, money, satisfaction. But then there's also like this
other type of life that people can optimize for, which is like a meaningful life. And
that's a life full of like significance and purpose and coherence and societal contribution.
And I think the older one gets, the more we think about living a meaningful life, like
what's the purpose of it all? You know, because more and more of our life is behind us and
less and less is ahead of us. And so we think, okay, what's the lasting impact that I'm having?
That starts to become much more valuable to us than it was when we were like 25 just thinking
about how to be happy in the short term. And so I think it's the same with the business,
you know, in a career, like it makes a lot of sense as we get older to think about like,
what's the impact of what I'm doing? How do I sort of tie all the things I'm doing together
into like some sort of mission and impact? And there's a lot of personal satisfaction
that comes from having, I think, a sort of meaningful, a meaningful life.
Yeah. Yeah. I always say, you know, freedom, I think entrepreneurs most should seek freedom,
purpose and relationships kind of in that order, although relationships probably before
purpose, I think, or in tandem with it. But like, I think that's one of the reasons I
sought entrepreneurship was the freedom from a day job and the freedom from being told
what to build and when. And I remember working, working, working towards it because I live
in the future like you do and just thinking to that day when I quit the job. And then
I got it and I was like, this is amazing. And it was amazing for like three months.
And then I was like, I'm kind of bored, you know, like, what do I need to do next? Because
I had freedom, but I really didn't have a purpose. I had a bunch of apps that were kind
of like, I'll had this autopilot traffic from SEO and ads and this and that, but like, nothing
was that interesting to me. It was just a paycheck and you know, it was a nice paycheck.
It was a hundred and I don't know, 120 to 150 grand, um, back, this is in 2007. So like
ran a long way. Yeah, it was great. And I was like, yeah, free. But then I was like,
well, I need, I need to find a purpose. And that was where I really double started doubling
down on talking about this on writing and doing the book and the podcast and all of
that came out in about an 18 month period. Um, because I was like, I want there to be
more. And here's the other thing, relationships, there was kind of no one else doing it. Like
I like Joel Spolsky was blogging in the early 2000s and he, but he started a software company
and then Patrick McKenzie started blogging a couple of years after I did. And he and
I ran across each other and I, and then I had heard of base camp, right? And they had
a disaster that I didn't use, but I'm getting to 2008, 2009. And I'm like, is anyone else
thinking about that or doing this whole, you know, the kind of indie hacker, like bootstrap
startup path. Is that a, is it a thing or am I the only one that's done it or will ever
do it? You know, cause I genuinely didn't know. And that was part of building the audience
that then turned into the community was like, I want there to be, I want to be able to hang
out with other people who talk about this stuff. Cause this is really interesting to
me. And no, no one else in my town gives a shit about this, but I need, can I find a
hundred people that I can get into a room with, you know, that care about it? And that
was a big thing. I mean, it's like that purpose thing that you're talking about, like freedom,
like when I talked to any hackers, the vast majority of indie hackers are looking for
some type of freedom. That's why they're starting their business. Cause they feel like they
don't want to work for somebody else. They want, they want more time. They want to work
with people they like, they want to create a freedom. They want financial independence
and no ceiling on their income. And I think that that is like a purpose, right? Like that
can be your purpose to like have this epic adventure that you're going on in order to
earn your freedom. And like you and I have both been on that adventure for some part
of our life, but then you get your freedom and you get there and like suddenly you lose
your purpose. You know, it's like you had this epic journey and you completed it and
you succeeded. And that's like now what, right? Like you're, it's like Frodo at the end of
the Lord of the rings, like the movie ends there. It's like, he cast the ring to the
fire. Like, I don't know. There's like 10 different ending scenes, but then it's over
and the credits, the credits roll and it's like, well, what did Frodo do after that?
You know, like sit around in the Shire, like telling stories about how he had this epic
adventure at some point. Like it's kind of hard to figure out what do you do after you
sort of accomplished your mission? Like, how do you find a new purpose? Right. And we can't
just get on the boat to the undying lands. Like, right. Yeah, he's not a thing. I want
to, I want to like piggyback on that topic because you've just talked about losing your
purpose or like you find it. It's the arrival fallacy, right? Is what it is. You arrive
and then you're like, once I will, I will arrive once I do this. And you do for about
a month or three months. And then you decide, Oh, I need to do something new. But we had,
I tweeted out and you retweeted. Thanks. You know, what should you and I talk about on
this episode? And there's a, there's too many topics for us to cover. But one that I think
is interesting is Arvid call said, please give them mental health topics in time. Building
anything is hard. Building it in the middle of pandemic seemed harder. Some people need
permission to let themselves feel this and you both can help there. And this obviously
is a topic that like my wife talks to my wife's a clinical psychologist. You should check
out the Zen founder podcast. If you want every week, she's releasing an episode on this topic
as a founder married to a founder, consults with founders and as a psychologist. But aside
from that, like you and I have shared our own struggles with, you know, building businesses
and mental health during, during that. So, um, why don't you start and then I'll go.
I think we both have more stories, you know, mental health is super important. You know,
I've struggled with like various mental health issues. Sometimes I've been very depressed,
I think three times in my life. And like one of them was this past year, I had a good six
months where I was just like, what's the point of anything? Well, I do anything, you know,
and it was a hard time because it's like the pandemic was very isolating. I had this road
trip that I've talked about where I was just like, not really seeing anyone and I moved
to Seattle and it was like kind of isolating as well. And I think for me, it really tied
into this, this topic of purpose because from like probably age eight, age 34, I've always
had this sort of like vision of like, what do I, what do I do with my life? And it's
like, I'm on this Epic adventure, right? I'm trying to build some very big ambitious project
and it's usually creative. It usually involves like building a website and designing it and
putting code together, which is like this awesome, you know, feedback loop of reward
and work and then reward and work. And I think for the first time since I was eight, I kind
of got off it last year and was like, well, what else is there to life? You know, and
I sort of found myself spinning and I wasn't sure what the reason was, you know, it was
like, it was all these like other proximate reasons, like, you know, is my relationship
with my girlfriend going okay? Or is it like my living situation? And it's really easy
to like sort of blame the wrong thing. But I think at the core, I just sort of lost the
drive that I had that filled up my days and like made every day feel like I was excited
to wake up and do something, you know? And I think everybody has their own like sort
of loop, their own sort of like, their own sort of like natural process where left to
their own devices, they'll do something. For a lot of people, it's like, I'm gonna look
at social media, I'm gonna come home and look at TikTok on my phone. For a lot of people,
it's like, I'm gonna come home and spend time with my family. For a lot of people, I dated
someone once, you know, she would just like impulsively just go out and just meet strangers
and she loved to do that. And that was like kind of her happy, like sort of resting place.
And for me, it's always like, I'm gonna sit down on my computer, I'm gonna code something
really cool and try to work on it. And like, I think without that, without replacing that
with anything, it was very easy for me to sit around and be like, well, now what, you
know, and like now I'm like dependent on other people to come in and like, you know, hang
out with me to do something entertaining or stimulating, or it was very easy to just like,
I start questioning my purpose in life. And so I don't know, I think this happens to a
lot of founders, you know, I've talked to a lot of people who have, it's kind of a cliche,
people like reach some like level of financial success, or they achieve some goal, and then
they're just like aimless. And embarrassingly enough for me, like it took me like six months
to figure out why. And then like, another few months, okay, what can I do that has like
meaning and purpose that'll, that'll be interesting and like, like, you know, fulfill me. And
then the answer is like, Oh, I should just work on any. Oh, yeah, like I'm working on
any hackers for more than just like, you know, like these sort of like, earlier reasons that
I'm working on it because it actually is fun for me. It actually is entertaining. It actually
is meaningful. Like I love the people that I work with, the people that I talked to,
the problems that we're trying to solve, like all the challenges in front of me with any
hackers in the way that I want to grow the site are really interesting for their own
sake. And so I had to kind of have this period of rediscovering why I'm not even rediscovering
it sort of changing the reasons why I'm working on the site and diving into those. And I'm
hoping that like, my entire life, I hope for everybody, this is the case that my entire
life is full of these epic adventures. And there's never really an endpoint, you know,
there's never really like a midlife crisis point where I'm done, and I've accomplished
the goal. And that's it, you know, I hope that I'm always sort of struggling towards
something that is really meaningful and really enjoyable in the meantime. And that even if
I never reached the end of that sort of tunnel, it's fun the whole way through.
Yeah. And I've seen I don't know if you've known people who retire, like who work a day
job for 20, 30 years, and then they retire, and they don't, they totally lose that meaning,
or folks who sell a company and don't have anything else to do, it can wreak havoc on
their motivation and their mental health. And you can go downhill, you know, it's kind
of a cliche at this point, like don't do that. Yeah, totally. But I think for me, it's like
I'd never, like, you don't, you don't realize you have until you lose it, you know, I'd
never had a second of my life where I didn't have something like that, you know, and without
it, I'm like, what's going on? I feel so like, what's sort of hard to diagnose.
I have 100% gone through exactly that. I don't even know how many times in my, in my life
from the time I was a teenager. And I've talked on this podcast about, you know, burning out
essentially while growing drip and just how hard some of that piece was. I don't know
if I had, I don't know what I had, if I had clinical depression for part of that, or if
it was just burnout, because it was just hard, you know, I was, I was stressed all the time.
Um, I was, it was a rough go, but what's interesting is more recently, like during COVID 2020,
I think a lot of people had a tough year that year for a lot of reasons. So, so did I. And
in fact, Sherry and I had just some, you know, we've been married 22 years now, like you're
going to go through ups and downs. And we had a pretty tough stretch there in the middle
of, of COVID. And I, there were a few days where I kind of didn't get out of bed and
I've never really done, I've never been that messed up before emotionally. And I remember
being like, I really want to keep doing like life. And I really wanted to hang out with
my family, but like, I don't have, I just didn't have the motivation to get up. I couldn't,
I couldn't look at my Trello board and say, I want to do these things. I didn't want to
do anything. You know, it was, it's, it's tough. And so I haven't traditionally been
like, I don't have depression, right? I don't, I don't have, that's not a thing that bligs
my life. In fact, I'm on the other side of the spectrum where I'm a stress anxiety person.
That's my whole family tree is all like alcoholics, drug addicts who are self treating themselves
for these anxieties, you know? And my dad, I've talked about this before, but he had,
he has OCD. He had OCD so bad. He didn't leave his bedroom for seven months when I was a
senior in high school and OCD is an anxiety disorder. So it definitely runs in my family
and it's something I've learned to cope with as an adult. Um, but I guess all that to say,
like this topic of founder mental health in general is it's always read and resonated
with me. And I think people never used to talk about it 10 years ago. And I think a
lot more of us talk about it these days. And I think that's probably helpful to normalize
it.
One of my favorite things about living on the West coast is everybody on the West coast
compared to the East coast in my experience is like, so like woo woo and like frou frou
like everyone on the West coast that I know, like has a therapist and on the East coast
is like a dirty word. Like you have a therapist, like what's wrong with you? Never tell anybody
about that. But like, uh, I have a therapist. He's awesome. He's like this like 75 year
old Canadian dude. I want to go a million miles a minute. You know, I talk so fast.
The second I get into therapy thing, I have like 15 things I want to talk about. He's
like, let's slow down courtland. Let's take our time and find your center and be one with
yourself. And I get like so frustrated for like the first five or 10 minutes. And then
I slow down. I'm like, okay, this guy's like, I want to smoke with this guy smoking because
it feels good. And I know that I need it. I need to chill out a little bit. And so yeah,
I think it's worth taking the time, whether you're a founder or not. I think everybody
needs to take the time to like check in with themselves and sort of work on your mental
health because I think it's, if your mental health is in a good place, I don't think it's
wise to take that for granted. And if your mental health is in like a tough place, obviously
it's like you got to prioritize that because that is sort of the engine that powers everything
else in your life. You know, and I think about it a lot when I think about like success and
people struggling to do things like everybody's going through different shit. You know, I
had so many, like I had a ridiculously good leave it to be for childhood. You know, like
I have zero trauma. I like zero like real true lasting hardships that I really had to
push through that like left a scar on me. And so like, I was like freed in my twenties
to just go tackle challenges without any mental health issues and stuff like that. But other
people are like struggling to get out of bed, you know, they're struggling to deal with
like terrible things that have happened to them. And they're trying to take on these
big challenges. And I think that like, it's really easy to underestimate that. And if
you're going through that kind of stuff, uh, if you were just sort of ignoring it, like
I think you're doing yourself a disservice at times in my life, I have ignored it for
too long. The other thing I ignored was physical issues. I know we're talking about mental
health, but like I had really bad shoulder and back pain, neck pain. Cause we all hunched
over our desks and I had it for years and it was kind of debilitating. It was to the
point where I was under constant pain. And why the fuck didn't I do something about,
I remember saying like, I don't have the time. And then I went to a chiropractor and a massage
therapist and it like didn't fix it quick enough. And I was like, I just don't have
time to carve out two hours a week to do this. So I, so I didn't do it. And it wasn't until
we moved to Minneapolis, I'd sold the company. I went to three different massage folks and
I found a dude who's really good and he, you know, integrates all these different things.
It hurts like crazy, but I went to him twice a week for months. And I just said, I'm carving
out this time. It also helped that I wasn't, I didn't still run the company so I could
just take a couple hours a week, but he, and it took him months and months to work it out
of me. And there were all these, you know, there's toxins and crap in your muscles when
they're like that. And I remember being like almost, I would almost get sick after her
because I had just let it go for too long. And it's like these chronic mental or, you
know, you don't, you shouldn't live like that. And I say that as much for anyone listening
as I do for myself in the future. I, I refuse to live like that again. You know, it's hard.
Like I think I met a person and she was like telling me about this phase of her life where
she was super grumpy and she was just kind of an asshole. And I asked her, I was like,
why are you such an asshole? Like, why were you being this way? And she's like, chronic
pain. She was like, literally had chronic back pain and it would fire up. And you know,
like, what doesn't make you a happy, agreeable person being in physical pain all the time.
It makes you really short tempered. And I think lots of people have like different things
like this that sort of affect us at a lower level. And that like, you know, bubble up
to how like we actually behave. And I think for founders in particular, we can be so single
mindedly focused on what we're working on, right? So ambitious, so driven. I got to work
on this business. It's got to take up every hour of every day. I've got to like, nothing
else is a higher priority. And like, it's easy to get into a mode where like, Oh, let's
put like working out on the back burner. Let's put mental health on the back burner. Let's
put like physical, like all the stuff in the back. That can, you know, that can come later.
And I think that that was like sort of a recipe for disaster. And it's really easy to like,
I don't know all these things. It's like, it's really basic advice, you know, get eight
hours of sleep, take care of your body, blah, blah, blah, blah, blah. But like, it's not
about whether you know that advice. It's about whether or not you're doing it. And I think
99% of people were not doing it. They're repeating it. You know, I'm repeating it, but not always
doing it.
Yep. Yep. And it wasn't until I retired from drip. Do you know tiny sees my retirement
project? That's what I put out to pasture. We were talking about it. I was like, yeah,
I could do this thing. Uh, just in my spare time. Um, but I want, so I want to switch
it up. We have, we have so many topics on this thing, but Liam Simons says, if you had
to fight one horse size duck or 100 duck size horses, which would you choose?
Uh, 100 duck size horses. Me too. Yeah. You imagine how terrifying a horse size duck would
be? It would say, I mean that beak alone, like those things are hard. I don't know if
you've ever been packed or like nibbled at by a duck or a goose. That stuff is scary
and their tongues are terrifying.
Have you ever looked like a duck in the eyes? Like any bird you look at, like licking their
eyes are terrifying. These deeply inhuman eyes. I can't imagine like a horse size duck.
I would rather do almost anything. So easy answer for me.
Meet me too as well. How about, um, oh, this is a good one. Greg Dignio says, at what point
in drip for Rob and an indie hackers for Cortland, did you guys want to quit? And why didn't
you?
Wait, why don't you go first? I mean, I guess you got already answered it.
I wanted to quit. I wanted to quit when Russian spammers were hacking us. I wanted to quit
when I thought I couldn't make payroll because I had over hired and I got a big tack personal
tax bill. Um, I wanted to quit when competitors would rip off my stuff. When, when we would
spend months building and thinking and marketing thing and someone would just rip it off shamelessly
and then, and the worst part was they would claim that it was their idea. And it was just
so I, I need to take, I take business a little too personal. I'm going to be honest and I,
that really, that kind of stuff really bothered me. Um, and, uh, even for, heck I wanted to,
when I left drip 2018, I had a, I took a few months and I evaluated, do I want to walk
away from startups altogether? Do I want to sell the podcast in micro cough? You know,
there were times where I was like, I don't know if I want to keep doing this. And I mean,
the reasons I didn't is cause I, we talked about it earlier as I can realize, oh, my
mission in life is this thing to, to promote entrepreneurship and to get more people finding
freedom purpose and relationships through it. And when I realized that it was like,
well, I already have these platforms. Why don't I build on them and just do more and
double down. And then in terms of drip, like the reasons I didn't quit when those were
happening was momentum. To your point earlier of momentum, like I just had momentum going
and I had a team I was working with and I couldn't just walk away. It's not like, like
if I was a founder, I may have like, I don't know, I may have trash some stuff, you know,
at a certain point, just table flip and say, this is too hard. And I could do an idea that's,
you know, more lucrative with for less work, but I did, but I had this team of, you know,
three, then five, then 10. And it's like, well, we're all, everybody's on board and
they kept me accountable unintentionally. They didn't come and say you need to be accountable,
but I felt the burden of like, no, I got, we, I had the vision. We all got on board
with this thing and I can't walk away from this, you know? Yeah. So he does a lot with
like founders were like, I think it's kind of a miracle. Like you've looked out into
the world, there's billions and billions of people who wake up every day at 9am and go
to a job. They don't even like that much and work that job and come up and they're consistent
and they'll do that day after day for years. Right. And I talked to a lot of founders and
it's really hard for founders to like our podcasters or whatever it is to last for more
than like a few months with like, ah, I give up, you know, it's too much work. And I think
one of the biggest difference makers there is besides the obvious, like I got to get
the bills paid is that accountability, right? It's the fact that like, actually have teammates
and a boss and people who are depending on me. And I think we're just tribal creatures,
like we're sort of wired to like not want to let down the people around us. You know,
if we commit to something and we agree to something and we have work that's waiting
for us, like it feels shitty to just quit and like not do that. And so I think one of
the best things you can do as a founder, if you really want to stick with what you're
doing, which is sort of necessary for succeeding is to surround yourself with people who you
feel accountable to, even if like you're their boss, you still kind of feel accountable to
your employees, to your partners, your co-founders, your team. And like, I love feeling that way.
Like I like my Ari, my podcast producer, I don't want to let her down. Like part of her
work is dependent on me getting the podcast out. You know, I can't like, and she keeps
me like, we have a calendar event twice a week. I got to meet with Ari. Like sometimes
I cancel, but like, I'll feel bad if I just abandon it, you know? And so I've also sort
of written off momentum. You know, I never really wanted to quit any actors at all when
things are going up and to the right. And then in the early days, I had this email list
where I would send out my progress every single week. Here's what I did. Here's what I did.
And people would respond. And so I feel super bad. I just didn't do anything for weeks.
It'd be embarrassing. Quite frankly, like what am I going to tell these people? I did nothing.
And so I had a lot of late nights on Wednesdays where I would just try to do something to
report because I was accountable. And the only time I ever got to feeling like, you
know, maybe this is what I shouldn't do was last year when I started feeling a little
depressed, a little bit down. Some of the things I was trying to do to grow the site,
like weren't working out. And so that sort of feedback loop I've talked about before
of, of, you know, positive things happening and encouraging you to try more things in
the future and being optimistic was sort of slowing down. And I was like, I'm trying these
things and that site's not growing like I want. And so like, maybe this is it, you know,
the amount of ideas and, you know, maybe I should rest on my laurels. I've done a good
thing and, you know, I wasn't working as much. Rosie Sherry, our community manager quit.
And so our team was like sort of winding down a little bit and we didn't replace her. And
so I had fewer of those mechanisms in place that keep you motivated. And it was the closest
I've ever gotten to wanting to quit and exploring like different things.
Wow. John Howard asks, I always love the conversations of the scrappy early days for indie hackers
and bootstrappers and then throws out a bunch of questions. What does it take to get to
an MVP? What does it take to get to dollar one? What does it take to define your audience?
I've been through it a bunch, but a framework is always fun.
My favorite framework, if I was an indie hacker right now, starting from nothing is to just
literally just solve someone's problem. Like any problem, but as little bullshit as possible
between you solving somebody's problem and getting paid for that as you can. And so Nathan
Barry has this excellent blog post called like the ladders of wealth creation. I recommend
it. And it's kind of like the way he puts it is like there's a sort of reliable progression
that you can take to like earn, build more wealth. And at the bottom ladder, you've got
like trading your time for money, like working for an employer, having a job. And the top
of the ladder is like, you're selling products, right? You've got like a social network or
marketplace or a subscription software business or something. And you try to work your way
there gradually. And I think what I would do is I would just start at the bottom. Okay.
I'm selling time for money. Well, how do I do that? But instead of working for somebody
else, working for myself, right? And so like you can go to, for example, and the hackers
is a website where people have tons of problems. You can go to any hackers, click monthly,
see the top posts for every month and like a top post for January is share your project
and I'll try to find you users. And there's 330 comments of people who are like, I'm working
on this project and I have a problem. I can't find any users. And there's this kind of this
one guy is going through replying to everyone and just trying to figure out what their problem
is and try to help them solve it. And like, I bet you 10, 20% of the people he talks to,
he could get on a phone call and be like, Hey, you know, 200 bucks, I'll do a consulting
call with you. We'll see where it goes. And he can make thousands of dollars tomorrow
with like five or six consulting calls, just cause he's solving somebody's problem. He
doesn't have to build a fancy website. He doesn't have to hire a team and build an app.
He doesn't have to do anything. Just literally like what's your problem? I will try as hard
as I can to solve it for people who are motivated to solve these problems because they think
they'll make money. And so if I were starting out, I would do that and just follow that
path and see where it takes me because when you solve somebody's problem, they pay for
it. Like that's a pretty good indicator that you're onto the right thing and you can maybe
tweak your idea to try to change your customer or the problem that you solve, but it doesn't
require you being particularly brilliant. It just requires you going to a source of
problems, which are really easy to find on the internet and then rolling up your sleeves
and doing something today, like right now.
Yeah, I'm glad you bring up the solve a problem because I always forget to mention it because
it is so ingrained in, it is such like a fundamental precept that I don't even bring that up because
I expect everyone already knows that, but they don't. And so I'm glad I'm glad. Yep.
It totally is. I forget. Well, of course you should solve a problem, but it's like, well,
not of course for some people listening to this podcast. It's of course, because I've
been talking about this stuff for 17 years and I, I think it's fascinating. We have the
micro golf state of independent SAS survey. We do a survey and then put out a report and
we talk about how people found that their startup idea, their SAS idea specifically.
And I just pulled the report up and 45% of respondents said it was a specific problem
that they were experiencing. And then it's another 22% a problem. My customers or clients
were experiencing. So you're at two thirds now. Another 13% was a problem or experience
at my day job. So now we're at 80%, another 11% a problem, a friend or relative was experiencing.
We're at 91% of hundreds and hundreds of respondents. So the rest is, I mean, we're at 91. Yeah,
we're at 91%. The last three are 8% said research, 1.5% said other and 0.2% said I purchased
the business. And so it's just like a problem that me or someone around me is experiencing,
you know, it is. And I think it's super important because if you're not solving a problem,
and that's where this is where like, I get a little prescriptive with the B2B versus B2C
thing. You and I've talked about this in the past. Like I just am so bullish on B2B and really
bearish on B2C, not only because I've owned, I think two or three products or companies.
One was an ecom site that served consumers, but because every B2C company, specifically a
subscription company that I see bootstrappers, they just, the churn is too high. They can't
find customers lifetime value. It's just the same problems over and over. So I never say,
never do this. But I say, you probably don't want to do this because the problems you solve
for consumers are just not as there's not as much value as if you solve it for businesses.
It's super true. You know, at the end of the day, like businesses have way more money than
consumers. They are more motivated to fix it. Most of the time, they have a gigantic list of
property to hire, they need to find office space, they need to market, they need to do sales,
they need to solve their own customers problems, they need an email solution, they need hosting,
they need accounting. Business have so many problems they need solved. It's just generally
a better bet to go that way. That being said, I do think if you're judicious about it,
and you want to do something that targets consumers, you can, you just have to really
think about the problem. Again, you can't think about like, oh, I want to build this solution,
I want to build this app or the service, you have to think about what's the problem I'm solving,
and like, what is the nature of this problem? Specifically, is this a problem that is lucrative
to solve? Because if it's not, you might solve it, you might get happy customers who say thank you,
and you're not making any money because they're churning or they're only, they're expecting it
for free. And so like, if you look at where consumers spend money, or even where businesses
spend money, I think the same formula applies. If you want to find a problem that's lucrative,
just look what people are paying to do, right? Every time somebody spends money, it's because
they're trying to solve a problem. People spend a ton of money on housing, people spend a ton of
money on transportation, people send so much money on education, it's crazy. I think that's what people
are like the most business like, where they think, okay, if I get this education, if I go to the
school or I take this course, I will then be able to use those skills I developed to go make more
money in the future. And so people are like willing to go into like hundreds of thousands of dollars
of debt to get education because they see how it will make the money in the future. And so I think
it's not a coincidence that like most of the people I know who have consumer businesses
that are successful are educating consumers in some way and helping those consumers become better
versions of themselves. Whereas people who are trying to sell like these little tools and apps
and productivity software, find it much harder because like the problems you're solving for
consumers is like, not that valuable. Like the average consumer like doesn't need a to do list
to organize her life, you know, whereas a business might need that because they have a bunch of, you
know, employees to coordinate, etc. And it's valuable for them. Right. Find a problem. And
then there's a bunch of different ways to do that, right? Like I'm working on this book, and I
have like seven different not frameworks, just thoughts of like, finding a problem looking
around you translate an existing idea to a new niche where it's like, Oh, CRM software. Well,
you know, who doesn't have CRM software is home improvement contractors. And you know,
who built a home improvement contractor CRM is Jonathan with builder prime. And he built it
to good revenue and then applied to tiny seed and he was in batch too. It's like,
just taking a simple idea of like, we're all familiar with CRM, but there are all these
spaces that don't have it, you know? And another one is like looking at a large space, competitive
space is if you're probably, if you're further along on the stair step approach, but that has
a hated competitor. And so for drip, it was infusion soft, right? And, and Marketo and Pardot
for, you know, I think for zero, you know, the accounting software, it was quick books.
They were the not quick books for Derek Reimer and Savvy Cal, very competitive space. But you
know, I, and I wouldn't say Calendly is a hated competitor, but there's definitely, you know,
were some improvements and some stagnation in that space. So there's, there's a bunch of different
ways. If you look around, the problem is, is it's the paradox of choice where there's infinite,
it's like, well, I could look anywhere for a problem. And it's like, well, maybe focus on
something you have or at a day job or friend or like, look at each of these things in turn and
keep a notebook around for a month. And, and then look at, you know, what are, what are your
expertise is in? If you've been a software developer at credit card companies for 10 years,
you probably know more about credit card companies and finance and banking than others. So maybe you
should lean into that a bit, you know, or if you've been all doing eat, you worked at Shopify
for five or 10 years. So it's like, you probably know e-commerce better than most people. There's,
there's opportunity there, you know, you want to do one more. Yeah. I could do these all day to
some of that. We had like a thousand questions. All right. Is this one Peter levels asked how,
how was the bootstrap scene in 2010 or earlier? And how did it change with indie makers, et cetera?
Were you around bootstrappers that long ago? Yeah. I was reading a bunch of base camp stuff back
then. Okay. Much of like, um, patio 11 stuff. I was reading Peltier and Balsamic back then.
What about me, bro? What am I chopped liver? I was writing all kinds of stuff. You know,
you're like, I, this guy's so annoying. I hate this guy. I just skipped, I just clicked my red.
Nope. And I spammed. But you've named everybody. That was it. I mean, in 2010, it was, I say
everybody I'm being a little facetious, but it's like there was Joel Spolsky. So that the only two
people I knew talking about entrepreneurship in any way that made, that resonated with me,
that wasn't just bullshit Silicon Valley. Everybody raised, raise, raise.com was Joel Spolsky,
who started blogging in 2000, 2001. And Paul Graham, who, well, you could say, well, he started
Y Combinator venture cap, but I was like, no, no, no. But he actually built a startup. He actually
sold it to Yahoo in the nineties. And then he thinks so pragmatically compared to a bunch of
the VC crap I was reading and ink magazine and red herring and all that stuff. So that was just
the two of them in the early 2000s. Then base camp came around and it was 2005, 2006, or it was
called 37 signals. First it was a blog. They were a consulting firm. Then they launched a SaaS.
And then it was me, peldy patio 11. And those are the only people that I knew until,
I don't know, 2008, nine. That was kind of it. What do you super niche? It was super nice.
There was, I mean, I did Y Combinator in January, 2011. And I remember going into it and talking
about Ramos. I really liked the base camp guys, like what they're saying. I remember Kevin Hale
from Woofoo came in and gave a talk and he was like, yeah, we never raise any money. We're making
like five million in revenue. We moved to Florida. It's pretty cool. And Paul Graham was like, he was
super pragmatic. He's like, don't raise more money than you need to. It kills a lot of companies
that could have had a 20, 30, $40 million exit. They swing for defenses, try to become unicorns.
And they weren't destined, their company can't do that. So don't raise that money and go for
the gold if you can't. And so he was even pragmatic about it. But like, there wasn't a lot out there
that was inspirational. And nowadays it's like a deluge. Like you could read and read, read all day,
listen to 15 different podcasts, and then discover another 200 podcasts and never get to the bottom
of it. It's just the secrets out, right? You can make money online, self in a self-funded,
self-sustainable way from the comfort of your own home. And I think that's the biggest difference.
And bootstrapping wasn't, I mean, it was kind of a thing, but now you say bootstrapping and
people know that's a movement. There are tens of thousands of us that want to do that. And
it just wasn't. There were a handful of people, there was no community, there was no central hub.
And in fact, that's why when we started this podcast and I wrote my book, it was still,
it was like startups for the rest of us. If you look back, this podcast should probably be called
bootstrapping, blah, blah, blah. But we didn't, while the term existed, it just didn't have the
resonance with this idea. It was more like, well, I want to do startups because they sound fun,
but I'm going to do it in a different way. It was really, really the angle there.
So do you think bootstrapping is still going to like, in my opinion, I think it's a less relevant
term than it was in the past. I'm wondering what your thoughts are like in the future of bootstrapping
and like how it is today. I feel the same way. I think you put out a post about this a year ago
where you're just like, is this really important? Is the funding mechanism, the most important part
of this business, or is the problem that you solve, how you go about solving it, how you grow it?
Isn't that all really important? I've struggled with that whole thing of like
scraping B posts. They're a tiny C company, but they're very public about their revenue.
They're doing north of a million dollars. And they got to the top of Hacker News with a post
that's like how we bootstrap to north of a million. And the biggest conversation in there
was just arguing over the term bootstrapping and whether they really bootstrapped because
they took tiny seed money. And it's like, if you talk to venture capitalists, if you raise
less than a million dollars, most will be like, well, they basically bootstrapped them. To them,
it's bootstrapping. But to someone who I've built businesses with literally zero dollars,
that is technically bootstrapping. But is it at all important to define? What if my dad gave
me 10 grand? Am I still bootstrapping? Yeah, compared to it. So that's where I've stopped.
It's not binary. I never thought it was binary. It's a continuum. I view there are people who
raise a little, raise a lot, raise half a million and are still acting like bootstrappers. They're
super capital efficient. They're super pragmatic. And they're building a real product for real
customers and paying real money. And that's what we all do, whether you have zero dollars in the
bank or half a million. I say bootstrapping mostly bootstrapped. Now you'll hear me,
you'll hear us say independent SAS or indie SAS because it implies, well, I'm not beholden to
anyone. Even if I raise money, I still have control of my company. I've toyed around with
all these terms. The thing I struggled with is in the state of indie SAS this year, the report's
not out yet. We did the survey. We said, what do you call your type of company? And we had all
these options. And it was like bootstrap SAS, indie SAS, independent SAS, blah, blah, blah. And
it was like overwhelmingly bootstrap SAS. Even people who had raised a hundred grand,
200 grand, 300 grand, you know? Yeah. Yeah. I think in a way, like the focus on bootstrapping,
even as a thing, it was sort of a reaction, right? It's a reaction to the fact that like
big tech really only cared about people who were fundraising. And if you wanted to get any sort of
media attention, if you wanted to have any sort of success, if you wanted to have any sort of like
support or resources, like you kind of had to go that path, which is not surprising because it was
like an early nascent days of startups, not that many people were doing startups. And so the people
who had all the money, the VCs sort of controlled the narratives. And so if you wanted to do
something outside of that path, like you had to be very vocal about the fact that this is different.
I am bootstrapping, et cetera. There's another way. And I think it's kind of like a measure of
success that like, that's not as important anymore, right? The fact that like, it's no longer a
shocking thing that you didn't raise a whole ton of money to start your company and it's still
successful means that like bootstrapping kind of like won its place as like a valid sort of a way
to sort of get started, which means it's not worth like glorifying quite as much as it used to.
You know, it was kind of okay. There's a lot of different paths. Everyone's well aware of that.
And pick your poison, you know, pick your preferred choice. So I don't know. I don't feel
like, you know, when any hackers started, I felt like there was like a big sort of fight. I was
always trying to wage like, you don't have to do it this other way. And the VCs, the investors,
like you don't have to do that. And now I'm like, do whatever. It's kind of obvious you don't have
to do that. I don't need to do that anymore. Now it's more about, okay, what do you want to do? And
how do you do it? There's all these paths and funding is a tool. And if you want and need that
tool, then do it. And if you don't, then don't. And that's, that's, you could be on, you could be on
indie hackers or part of microconf and you can raise money or not. It's just, we're all in this
building, you know, trying to become independent, sustainable companies. I find it interesting
because I, you brought up that bootstrapping and the real, I think religious adherence to it was
a reaction against the broader narrative of a venture funding. I had this exact conversation
about two weeks ago with a friend of mine. And I said, you know, I know that, and I think base
camp was a big part of that, to be honest, Joel Swelsky was a little bit of a base camp was so
vocal about it. And they got a lot of press about it. And I was talking to my friend and I said,
I understand why they did it. And, you know, I like Jason and, and DHH, they invested in
tiny seats first fund. They're mentored. Like I get it, but I actually think they went a little,
I think they may have long-term done some damage. I think by making it such a religious thing,
like they, you know, they, they used to say like, we, we, um, well, bootstrap will never take
funding. Anyone who takes funding is XYZ. They also would say like, we don't split tests. We don't
track in our funnel. Like we would never sell our company. Like planning is guessing. We don't
market. It just works. And they said all these things and they were shocking. And, but, but I
think a lot of people saw that or still hear it and think that that's the way to grow a business.
And I actually think it's not, you know, I think those are anti-patterns. Um, and I asked Jason
Fried about he's been to microconf. He and I've had breakfast. He was on stage. I did a Q and
A with him. I asked him about some of these things, you know, about like why I was base
camp successful. He said, we got a lot of things right, but we got a little lucky. And, and he,
he admits that, you know, they were early and they, they built, you know, they built a good product
and, and they did hit something just right at the right time. Um, but I do think that that narrative
is a bit of the religious nature of it or this utter black and white nature of it, I think is a
bit played out. And I think it's an anti-pattern. I think it's detrimental to new entrepreneurs
coming into the scene. There's like a sense in which it's like, kind of got to look at like,
why are people writing and saying the things that they're doing? And the base camp guys are just
expert markers. Like they are really, really good. I mean, they built productivity software
and they were like trailblazers. I mean, they created rails, you know, they were doing this
like way before everybody else, but also like they really got people excited about the fact
that they built productivity software. And how do they do that? By having great marketing,
great messaging. They always stood for something. They always had an enemy and you know, and like
the, the sort of point there wasn't necessarily like, let's be responsible stewards of how
everyone starts companies in the future. It was like, how do we get the word out about our
philosophy and our ideals? You don't do it by making lukewarm statements. You do it by saying
like fundraising is evil. You know, you do it by saying like, we're fighting against the big guys.
And like, that's the kind of messaging that resonates, that gets people talking. People
argue against you. People take a side, you know, even, and even on there, like I think it was rework
or it doesn't have to be crazy at work. One of their books, they have like a chapter that's
basically like pick a fight, you know, and they're just telling you their strategies,
like pick a fight. And I think that does create, if you are not the sort of person to think about
things deeply, it does create like religious zealots who, who take a side and who don't like
give the other side any real thought. And I don't think that's the best way to be as a founder.
You know, I think, I think the best way to be as a founder is when you're marketing,
pick a side, be super, you know, like out there and opinionated, opinionated exactly.
But when you're making decisions internally, be rational, do cost benefit analysis,
figure out what it is that you want. Don't close yourself off to any particular path
for religious reasons. I think that's good advice, not only for founders, but for all humans,
actually to just, you know, to evaluate both sides of that. I'm glad you said you're like,
they're expert marketers and they did this as marketing. The best marketing is when you don't
know you're being marketed to, right? This is what Steve Jobs and Apple did so well is he would do
these things that everyone would like want to be like, we're not going to live stream our product
announcements. It's like no other company does that. They want as many people to see it, but they're
like, no, no, thanks. Like we, it's this secret thing, you know, and, and base camp did well with that.
So I had DHH on Andy hackers a couple of years ago and we did like a debate. I'm like, all right,
DHH is like this fire brand on Twitter. Let's do a debate on like work-life balance, you know,
and I was trying to set him up with somebody that would be like his hated enemy, like key for
bar or something. And he refused. He's like, no, I'm not going to come on and talk to somebody that
I hate. So I had him talk to a Natalie Nagali who runs a very calm company, um, wild bit. It's very
bootstrapped. It's very like kind of in his style, but she had kind of a different point of view and
thought that DHH's point of view was unrealistic. And it was so interesting, the difference between
him on Twitter, starting these crazy fights, taking these like crazy hard line opinionated positions
and him, when you talk to him and it's like a real time conversation and he's utterly reasonable
and rational. And it's like, okay, you can see, you can see the difference, you know,
the marketing is like marketing. Right. Well, sir, we've been, we've been chatting for a while.
There's a lot of good, good topics here. I hope that, uh, folks in both of our feeds have, uh,
enjoyed this conversation. I'm at Rob Walling on Twitter. You are CS Allen. That's A-L-L-E-N.
And of course, anti-hackers.com. And I don't know, what do I say? Microconf.com. We, we do a lot of
things, but, uh, yeah, well, I think if you're an anti-hacker listening to this and you know,
you're considering starting a company and you want to like do something a little bit bigger, uh,
raise money from TinySeed. I love TinySeed. I think raising money is totally cool. And at the
end of the day, like TinySeed is sort of designed for people who have the bootstrapper mindset.
Um, you know, trying to find investors is, I think a big part of that is finding the right match.
And so I like what you're doing at TinySeed. I like anyone who's basically trying to help
anti-hackers. Uh, and so I'm, I'm putting in here an involuntary ad for your,
appreciate it, man, your funding mechanism here. Check out TinySeed if you're an anti-hacker.
Thanks. And yeah, this'll go live when applications are still open for our, we do, um, two funding
batches a year and in the U S and the Americas, and then we do one in Europe. And so if you hear
this and you get there quick enough, head to tinySeed.com slash apply and, uh, apply to our
accelerator. It's super fun. It's a year long remote and it is, um, focused on bootstrap and
mostly bootstrap SaaS. Cool.