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 Ben Orenstein and Derek Reimer on the Art of Product podcast.
They've both been on the show before, Ben is a co-founder of a company called Tupel,
which has got to be the best tool for remote pair programming, and Derek is the founder
of a company called SaviCal, which is what I use to schedule meetings, podcast recordings,
and literally any type of appointment where I need to see if my calendar matches up with
the other persons.
In this episode, I talked to Ben and Derek about community building, about long-term
goal-setting, and about building a dream team of people that you actually enjoy working
with at your startup.
If you liked the episode, make sure to head over to their podcast, The Art of Product,
and subscribe.
So Jared and I were noticing that you have not been very active on Twitter lately.
I'll just come out and say, I don't like tweeting.
I don't like being a personal brand that much.
It's a lot of effort.
It feels like a sort of endless treadmill where you can never really win.
You're just always sort of running off of it, and the seconds you stop, you die.
And so I just stopped, which I guess means I'm dead.
But I think for me, building a community, the cool thing is community goes on without
me.
I can step away for a week or two or a month, and Andy Hackers goes on, because I am not
the value for Andy Hackers.
It's everybody in the community making posts and talking to each other and leaving comments,
et cetera, et cetera.
It's like I have the opportunity to build something much bigger than myself.
And every now and then, I find myself backsliding.
I talk to a friend who's just crushing it on Twitter, or their newsletter just hit 200,000
subscribers.
I'm like, oh, man, I'm doing it wrong.
Should I do that?
And then I ask them what their goals are for the future, and they're like, well, I hope
I can turn my audience into a community so that I can take a breather.
And I'm like, wait a minute, I'm already there.
So I probably should, quote, should tweet more, and it would be nice to tweet more.
But it takes a lot of energy and effort to try to get the community going where I want
it to go and have the sort of life that I want it to have.
And that's what I'm spending 99% of my time doing.
Yeah.
I have this weird, I mean, yeah, I have this drive to do more Twitter, or when it's good,
I find it really engaging and fun.
And the people I follow are really interesting, and so I like reading it.
And I feel like I for sure am making new connections there, which is awesome.
I'm sort of viewing Twitter now as the first stage in my long-term recruiting pipeline,
where it's like, let me start having random interactions with Twitter folks so that maybe
when they start getting a little bit bored, maybe they DM me, or maybe when I DM them
in six months, they're like, oh, yeah, yeah, I've been seeing your stuff for a while.
So there's real, potentially massive business benefit to it.
And so I have this kind of, it's value with a side of addiction, where it's like, I just
key, it's really gonna suck me in for longer than I want, or anytime I run into something
challenging, like, let me just go open Twitter for a while.
Yeah, I have this thing that happens where I'll sit down on my computer, I'll type in
and it'll just automatically fill in news.ycominator.com, or I'll type T, and it'll automatically fill
in twitter.com, and I'll press enter, and I'll have some reason to go there.
Like, I went to Twitter to DM you about this podcast, like 10 minutes ago.
And then I literally just spent five, I blackout, spent five minutes scrolling down the feed.
I forget why I'm there.
Then I'm like, what am I doing?
And I have to retrace my stuff, and I'm like, oh, yeah.
So they've got the formula locked down, they hired these psychologists, they know exactly
how to do it.
And it's called Hooked, about how to build habit-forming products.
And it goes into the psychology of novelty, and how we are inherently addicted to these
processes like slot machines, where we can't really control, and we don't know what we're
gonna get.
And scrolling down a feed, where every other post is garbage, but some of the posts are
like gyms in the rough, that is somehow evolutionarily connected to our drive to, I don't know, hunt
through the bushes for berries and stuff.
And so we're sort of rewarded, I think, psychologically for doing that, and I think these psychologists
have figured this out, and put it into their apps, and if I can get a little bit of that
into any hackers, then I have a much more successful website.
Are you happy with how the community's going?
Like who's in the community, and how they act, and what they do, and all that?
I'm happy with the trajectory, especially over the last couple of months.
And I think that that is, as a founder, that's what you live and die by, the trajectory.
Are the numbers going up?
Because once they are, you can imagine some promised land where they are at an awesome
place, and the people that you want in your community are in your app, or using it, etc.
And even if you're at a high level, like I just saw Facebook reported, they've lost
users for the first time.
And Facebook's huge.
They have billions of users.
I bet you nobody there feels good that the trajectory is down, right?
So it's not about the absolute number, it's about where you're headed.
I for sure would like any hackers to have a lot more, I think, experienced founders
on it.
Right now, I think it's a little bit, like Twitter, you go to Twitter, like everybody's
on Twitter.
You can learn anything from anybody on Twitter, whenever they have the desire to tweet it.
And on any hackers right now, it's mostly like your peers, especially for an early
stage founder.
And I would like to do more to organically bring people into the community, and that's
a tough problem.
Because you can do it in inorganic ways.
I can host somebody from an interview, or have somebody on for an AMA.
But everybody knows, this person isn't really here, they're just sort of doing a drive-by
participation.
And so you've got some strategies in the pipeline, we're getting more, I guess, influencers,
so to speak, and experienced founders who participate, I think, regularly.
And that would be awesome.
That's kind of the holy grail.
Yeah, I don't know how it happened, but in my mind, somehow, indie hackers became associated
with like, you're new to it.
You're trying to get into it, you're trying to break in, and it's like a supportive group
of people that are going to, they're all kind of have the same, the same goal there.
That sounds always been.
But it's, I mean, it's, it's, it used to be more story based, I used to like, bring people
on and tell their stories.
But like, the community forum itself has always been more of like, you're new, you know, you
just started, you're struggling, or you just recently succeeded, and you want to tell everybody
about how you did it.
So you say you that that's how it is, you want to bring more experienced people in.
Is it important to have like, cover more use cases, like, can it can it just be for the
new people as like a springboard, get your going thing or
I don't want it to be that way.
In part, because it's ripe.
It's like, okay, well, the point is like, grow, get bigger, you know, and it's like,
all right, that's fine.
Like, I'll grow and get bigger.
Like, any hackers doesn't have a business model, like I abandoned, like, it's not making
money.
And even if it was, it wouldn't move the needle.
It's ripe.
So it's like, okay, what's impactful?
Well, there aren't that many successful early stage community state communities for early
stage founders, like they don't really exist at a large scale.
And so getting bigger and being more impactful that way is what matters.
And I think for that to work, like you can't be a school, right?
Like Harvard's very successful.
But guess what, like, everybody either drops out or graduates, like they don't come back
repeatedly.
And so Harvard's like undergraduate class size stays the same, right, whereas a real
community like Twitter, or Hacker News or Facebook or something like ideally it's growing,
which means people aren't churning or graduating.
And so if it's only a place you come to when you're early stage, and then you like wash
out after a certain point, you're like, thanks for the information I'm out, then we're not
really succeeding at growing.
And so that's kind of a tough nut to crack, been trying to crack it for a long time.
Oh, no, I was gonna ask, like, this is sort of related to what what's go the community
dynamics that I see going on, especially in like a lot of indie hacker, like self identified
indie hackers is like the trend of like putting the little like progress bar for revenue in
their on their Twitter bio and like doing a lot of like revenue sharing and even seeing
this more and more happening with like, people who are further along, like just constantly
continuously posting MRR updates and, and like spending a lot of time on Twitter and
stuff.
And I wonder, like, do you think that's like a healthy pattern for like, is that encouraging
good behavior?
Is this just creating like an inferiority complex among some people as they evaluate
their peers?
Like, what are your thoughts?
Yeah, those dynamics, cost and benefits, man, there's nothing that's truly pure.
That's all good.
And I think at the end of the day, like this revenue thing, if I've learned anything, it's
one of the very first strategies that happened in the hackers, besides the name was like,
people respond to revenue numbers, when people see money, they immediately think of how that
would apply to their life.
It's very inspirational to see a dollar amount.
And I think if we're trying to inspire people, like you need to give them a goal that they
can relate to, you know, if I told you like, hey, you know, I just ate 120 hot dogs in
an hour, learn how you can do it to like, you're not going to read that book, because
you don't want to eat 120 hot dogs in an hour.
But if I'm like, hey, my business is making like, I'm on Peter levels, his Twitter profile
right now, he's got that bar.
And so it's like his bars got all these little green dots, and then he's got some white dots
for like how far he hasn't made it.
And he's $2.8 million a year, and to his $4 million a year target.
I don't know why that's his target.
I don't know when he set that target, like it wasn't his target starting off, but like
he's advertising that and people who see that are like, dang, this guy's got it together.
He's one person making all these fun businesses, tweeting all these cool things.
And he's making $2.8 million a year, like, I should start something, you know, and it
really does get people to start stuff.
Like I've seen it and heard it year after year after year after year, that people are
inspired by these stories.
And so that's the good side.
The downside, as you pointed out, I was like, yeah, some people probably feel inadequate.
People probably feel like they're not making enough or doing enough.
But I think that happens anyway.
And I think the costs are maybe worth the benefit.
And so I like the fact that there's diversity, like not everybody needs to do that.
It shouldn't be like the main focus.
But I think that it does help.
It does get more people trying to do this.
And I think the world's a better place if more people realize they can start something
online and make a lot of money and attempt to do it.
You mentioned that you were that the trend was good.
So are you are you tracking like monthly active users or something like that?
Yeah, we track like what I care a lot about is basically like participation, like how
many people are commenting, right?
And when they comment, like we actually measure like thoughtful comments, not just like, oh,
congratulations, which is not a very thoughtful comment, it's helpful, whatever, but like
people leaving like, you know, almost like a textbook of wisdom and reply to somebody
else's comments.
It's been steadily going up as is retention recently.
And so there's a really good numbers like those are things to track.
And like that is not easy to do with where we are right now, because it's just a lot
of modeling like what we want the community to be.
And I think if you go to like a website like Hacker News or Reddit, it's just so new every
day.
You know, we were talking about psychology and novelty, Twitter, this is the same way
like you go there, you don't know what you're gonna get.
It's different every day, right?
If you go to Harvard, it's the same every year, it's the same classes, right?
So eventually you graduate, because even though it's helpful, you get bored.
And I think when any hackers for the longest time, it's been kind of the same posts over
and over again, you know, like, after six months on any hackers, like, this is your
fifth time sharing what product you're working on, or, you know, talking about how to do
SEO.
And it's up at some point, like I get it, you know, and so a lot of it, I think comes
down to inspiring people to have discussions that are like, seemingly off topic, they're
like, not necessarily like, how do you grow your business, but then might be like, okay,
what do you think about like this new, this news that happened?
Or what do you think about, you know, what are your New Year's resolutions, or like things
that are tangential to being an indie hacker, but that like, if you're going to talk to
anybody else on earth about these things, you might feel happier talking to another
person who sort of like you another founder, then like some random person on the internet.
And I think that's kind of the heart of a community.
It's bringing people together who are similar and have a lot to talk about, rather than
constraining the focus of conversation on only a particular topic.
I have an idea for you, and it might be a terrible one.
But I was invited, this was a couple of months back by another founder who had started a
circle community for SaaS founders over a certain revenue level.
And I think I had like mentioned somewhere that like, I'd crossed this milestone.
And then he was like, Hey, just noticed that.
And by the way, I started this thing.
And there's just, you know, it's like a relatively small group of founders.
I don't know all of them directly.
I'm familiar with them from kind of Twitter and just our industry, but like, it is definitely
a smaller, more constrained group.
And I would say this is, it's not quite the same level as like a mastermind group where
I feel like I can share every single detail about my business, but it is inherently a
little bit more constrained.
And so there are more kind of interesting conversations going on, I'm finding in this
like more private venue.
So it's still like, I would say it's, it's community, but it's a little more constrained.
It's like kind of siloed in a, in a smaller group setting where then people can feel like
they're even more open.
And I wonder if something like that, like as you're looking for people to graduate from
kind of earlier stage where like everything's public because there's not much proprietary
to hold in, you know, and not just talk about publicly, but as the stakes get a little bit
higher, I, I know in myself, like I share less of the like really key behind the scenes
details because some of that is like the secret sauce for what's making the business work
right now.
You know?
Yeah, exactly.
And I think that's just natural, right?
At some point, like you just don't want to share everything with everybody and something
like Twitter.
Okay.
Like you have every day you see this huge threat or some founders sharing all their learnings,
but it's like, that's the numerator.
What's the denominator founders who aren't saying, saying anything, you know, much, much,
much, much larger, like, and I don't have those kinds of numbers to like hope for that
sort of outcome.
And so we have thought about like the sort of like a cohort based approach or like small
groups of like revenue level type things.
But like, in my mind, that's kind of a solved problem in a way, it's very ad hoc, like there's
so many Telegram groups and WhatsApp groups and founders who talk to each other.
And it's just millions of those, to be honest, and they work, but there isn't like a place
to go where like, there's a sum total of everybody's knowledge except for perhaps Twitter, Twitter
is probably the best community of startup founders, in my opinion, but it's missing
some things because it's kind of everybody is not just startup founders.
And so a little few things get sort of lost in the muck.
But yeah, I mean, I think it's a good idea, it's just difficult to harness.
And it's like, not perfectly in line with our goal, which is like, okay, how do we become
like an open community for everybody?
And if people want to have these like little small communities, I think that's awesome.
It's not what we're trying to do.
And to be honest, I'm not sure if we could facilitate that as well as like a good, you
know, I message group or something.
But I mean, there is also like the Reddit strategy or Reddit is like one community supposedly,
but actually, it's like a combination of like, thousands of subreddits that like sum together
to make one homepage.
And like, that is kind of a clever way to like, use the smaller group strategy to accomplish
the bigger group strategy, which I think is really interesting.
And so we thought about that too, with any actors groups, but it's still a lot of work
because then you got to get people to like, get these small, tiny communities up and running.
And that's hard.
It's almost like running a little startup, right?
Most subreddits fail, and they're hard to get traction on just like the main websites
hard to get traction on.
And so it's a fun problem.
It's like all incentive design and like, trying to think about like psychology of how people
work, you know, it's not like a very clear, well defined, SAS problem where your software
either does the thing or it doesn't.
It's really, I think a study in like human psychology, like what gets somebody to open
a website every day?
Like what gives them that little hit of joy?
And it's difficult because people don't necessarily report accurately.
Like you don't really know, it's hard for people to tell you why they go to Twitter
every day.
Like the Twitter team probably knows a lot more about why people go to Twitter every
day than the average Twitter user.
And I'm not sure that's the case with most software.
I think it's usually the other way around where the companies are trying to figure out
from their users why they use it and the users know the people making it might not.
Was the community thing always the goal of IndieHackers?
I feel like I remember the day, like my interaction, like my, I think the first time I came across
you was I think the podcast seemed like, oh, Kirtland just has this cool podcast.
Like was it always the goal to just like, I want to get thousands of people and teach
them how to like help them, have them help each other and build businesses?
Yes, that was the goal.
In fact, the goal was not to have a podcast.
It was like on my list of things not to do early on.
I don't want a podcast for the same reason I don't like Twitter.
I don't want to be on the treadmill running and endlessly producing content and that being
the thing.
And I was okay with doing that with like the email list and the interviews that I used
to publish to the website.
So IndieHackers started off as like a blog that was just nothing but interviews.
It didn't look like a blog, but it's essentially what it was.
I was like, okay, I'll do this temporarily, but it's only to like bootstrap an email list
that I can use to bootstrap traction for a community and the community will run itself
and I can sit back and like collect my page.
You know, that was kind of the goal.
And so the very first day of IndieHackers, there was a link at the top that said community
forum and you went there and it was just like, okay, sign up if you're interested in this
because I wanted to gauge interest.
And so like it was kind of cool to watch that plan unfold and like work out and there's
some unexpected stops along the way.
Like it did start a podcast obviously and that's like arguably one of the most popular
parts of IndieHackers.
But yeah, I think the whole point is to have a community.
And I think beyond that, like if you could build a big enough community at the very top
of the funnel of entrepreneurship where people are just now starting to figure out they want
to do this, there's so much you can do later on in the funnel in terms of redirecting people
where you want them to go, whether it's fundraising a particular type of way or using a certain
set of products, like that's a very powerful position to be in.
And so I got to crack the community nut first.
And that's a hard one to crack.
But if I do, there's a lot of options.
So you feel like it's uncracked still?
Oh, for sure.
It's like constantly plateauing.
And then it's like, okay, well, you hit product market fit for like one level of community,
but like not for the next level.
And it's difficult to get it to the next level.
But like right now, it's like maybe 11, 12,000 visitors a day come to IndieHackers and three
or four thousand of them are signed in community members.
Like I think it can be 10 times that it's not going to be easy to get there.
But once it is 10 times that, like I feel much more like, okay, I've sort of, I've sort
of cracked this nut, like it's a significant percentage of new founders actually come here
rather than like, you know, four or five percent.
Does Stripe, whoever you report to at Stripe, like sort of encourage you to set growth targets
on those numbers?
A little bit.
Yeah, definitely.
I set growth numbers when I joined, they were astronomical.
We actually have hit a few since then, I was like, that's crazy.
But also like it's been five years, four years and so I would have hoped to have hit more.
But it's pretty hands off.
Like no one at Stripe is like breathing down my neck asking me where our numbers are, etc.
I can easily go months or upwards of like, you know, close to a year without necessarily
reporting in to anybody if I don't choose to do that, which is really nice.
So I get to choose where I want to spend my time.
And yeah, I mean, recently we like kind of reconfigured our numbers, like we're trying
to figure out, okay, what do we need to do to get to the next level?
Like what's important here and like you'll probably see the indie hackers homepage change
a lot in the next few months to sort of accommodate like the one goal that we have right now,
which is getting more people to leave thoughtful comments and to getting like sort of higher
profile people in there as well.
So right now it's like the homepage is like we've got a job board and we've got meetups
and we've got a list of podcast episodes and a link to our store and like none of that
has anything to do with the goal that I'm talking about.
So very easy to get distracted with the community.
But so I mean, are you getting are you getting bored of this particular problem?
Not at all, man.
Like, I've had periods I was just talking to Rob Walling about this last week about
how like, I strangely just like deliberately decided like maybe it's time to think about
other things.
And then I wasn't very happy.
I'm like, what's missing from my life, you know, I'm like, oh, it's because I like I've
always worked on like some ambitious project with some like huge goal at the end.
And it's not even like hitting the goal that matters, right?
It's the fact that like you have this like optimism for getting somewhere and you have
these like tricky problems that like occupy your mind and like fill up your days that
it's just really rewarding to work on.
I mean, I have a couple startup ideas, but it's hard to imagine any that are like more
engrossing than like, I'm trying to become the biggest community for startup founders.
And I get to talk to people all day, people like you guys and people like you want in
the actress forum, who are really interesting, who are all doing super interesting stuff
who are all like themselves, like on their own, like sort of epic journey request.
And I get to sort of design this website where like, I don't know, like I'm not like some
big company where there's like this huge development deploy process, like I just get on have an
idea I click deploy, it's up in like five minutes, I break the website all the time,
no one even notices, and 10s of 1000s of people a day come through and use the changes and
remark on them and comment on them like it's a really addictive feedback loop.
And so I think like the long term goals and plans are very ambitious and seem like very
meaningful to me.
And even the short term sort of day to day is very addictive.
And the same way that Twitter city did addicted.
So I don't know if it would be wise for me to just quit and do something else for the
sake of novelty.
And I think I have a lot of unfinished work to do.
Like I didn't think about this when I started Indie Hackers, like it was wasn't my plan.
I didn't think it was going to be infinitely great and infinitely entertaining and stuff.
But I'm glad that I lucked into working on something where I feel that way.
And I'm sure like by the time at the next plateau, it's still it's gonna be a new set
of challenges that are like, very different, you know, and I'm grateful for that.
I heard you on some podcast recently, I can't remember who you're talking to, but you said
something like very frank, which was along the lines of like, I've got this stripe stock.
And so I know I'm basically set financially at some point.
And so I'm like, I'm chilling.
I'm like gonna figure out what I want.
I'm not about money anymore.
Like, I don't have to worry about money anymore.
So like, all right, well, what, what's the point, right?
And I think for a lot of Indie Hackers and founders, like, it's not popular to say it's
more popular to be like, I'm only in it for the mission to help the world.
But it's like, no, we're all real people, like money matters, and you can do good things
with money.
You can make your life better.
You can make your family's life better.
You can have more time and freedom to do other things that are meaningful.
And so I think we spend so much of this time on this, like, this journey and this challenge,
like, to make enough money to be financially free, to have more free time to work on the
things that we want.
Right.
And then like, once you sort of get there, you realize like that journey is over, sign
for a new journey.
Right.
And a lot of people, like, especially in Silicon Valley, they're just like, all right, let
me just set the bar higher.
I made $10 million.
Let me make 100.
I made 100.
Let me make a billion.
And to me, like, that's not like something inherently wrong with that, if you've really
considered it, but I think if you're just automatically doing it, then I think you're
there's probably like, you know, room for improvement in your thought process, you could
be a little bit more deliberate about what you want to get out of life.
And so I'm sort of in a phase where I'm thinking about that.
And it's made me like a lot more about like the mission of indie hackers and like how
I spend my time.
I mean, I'm sure you guys are not in that, like, too far from that.
Tupel's doing pretty well.
And like, Savvy Hal is like, I don't know, I see a lot of Savvy Hal links.
And so at the end of the day, like, whether you're there or not, or not, like, you're
gonna have to start thinking about that pretty soon.
And it's not necessarily the wrong answer to be like, okay, I did the thing, I'm gonna
go work on something else.
Like, I talked to founders all the time on the podcast, who will have this riveting story
of how they started their startup, and all the challenges they overcame and where they
are now to show their revenue numbers, then after I stopped clicking record, they're like,
I can't wait to be done with this, you know, I have 10 other ideas I want to do.
And there's nothing wrong with that.
You know, I think it's part of life that you move on to new projects and things, especially
in the tech industry, with the average job 10 years, like two and a half, three years.
So as a founder, you're working like probably three times that before your business is like,
quote unquote, successful on you.
And I think about moving on to something else.
People ask me pretty frequently, like, oh, like, you think you're gonna sell some day
or like, how long do you think I'll do this and this, the way I feel about it is kind
of like, as long as it is interesting, as long as it's stimulating, and like, not fun
necessarily, but you know, like, I'm growing, and it's challenging, and it's a challenge
that I relish, the idea of just like, oh, sell the thing, and then now you have a pile
of the money, not appealing at all, but it would be more like, there's this really cool
thing over here that I can't stop thinking about.
That would be like the more likely thing that I'm like, oh, I have to step away from this
because I have to go do this other thing.
Is tuple still this really cool thing that you can't stop thinking about?
Currently yes.
Yeah.
What makes it that?
Well, my job keeps changing, which is the thing I love.
It's like we're nine people now, it's like the like, we're taking on more and more things
and like, doing all this hiring, and so it's, I think it's partly the dynamic nature of
it.
Like, it's like, it's like, I'll figure out a project and then wrap it up and be like,
okay, now to dive into this thing over here that I have no experience with, and I'm going
to try to figure out from scratch.
A lot of people don't like that.
Like, I talked to a lot of people who are like, I just like to code, you know, or I
just like this thing, and my job is changing, and I've gotten away from why I wanted to
do this in the first place.
So it's pretty unique that you like, you like the fact that it's changing.
Yes.
I mean, yeah, it's, it's mostly good.
Sometimes I do miss just like the simplicity of the coding or it's like, I will do a thing
today that I know how to do.
It's kind of nice.
I like that it has a nice, nice bound boundary around it, but overall it suits me nicely
that way.
Yeah.
What about you, Derek?
How's Savi-Cal?
Yeah, I would say I'm, I'm having a blast.
So I just hired my first engineer, first full-time engineer.
So it's like a big, just cross that like huge milestone where it feels like I've just unlocked
a major cheat code, you know?
And it's crazy because I mean, now this, this brings me back to thinking of when we first
grew the team at drip, you know, five years ago or so, six, no, no, probably like seven
years ago, actually.
We've hired our first engineers and like had to flip out of that mode of like, I'm just
kind of the soul maker into, I am helping, you know, shepherd along some other people
who are trying to level up their skills and build their career and do their best work
and execute on their, their passions.
And I get a ton of joy out of that.
Like I don't know how I would, I don't know how it would be if I were trying to like manage
a really large engineering team.
Like I'm sure it would, you know, become the job would, the nature of the job would change,
but for now, like the thought of like building a small team, managing a small team and like,
you know, just being able to like watch people do their best work and help facilitate that
gives me a lot of fulfillment and also I know it's like super good for the business.
You know, it's like, um, it's just going to be such a, such a multiplier.
So these are still like, I'm in that really, really fun phase and I'm, I'm a little bit
scared that at some point something will change and like suddenly I'm finding myself like,
oh, I just don't enjoy the job as much anymore.
But I don't see that on the near term horizon, which is, I'm glad about, I feel thankful
about.
I was thinking the other day, how crazy it is that were the types of conversations that,
you know, I'm having with, with other founders and stuff where, where we're actually grappling
with this concept of like, what happens when you have so much money, you never have to
work again.
And just like, I was just thinking about how crazy this is probably like, if you know,
my relatives overheard these types of conversations or just people from past generations were
like, you couldn't just build a business that might in the span of a couple of years make
you more money than you could ever spend in a lifetime.
And yet these are like problems that a lot of us are like having to potentially grapple
with and it comes with its own set of set of problems around like, well, if I don't
have to work for money anymore, then what do I do with my time and how do I not get
depressed?
And so it's fascinating to me that these are, these are, these are the conversations that
are happening more and more in large part because of what tech enables.
Yeah.
I talk a lot about like freedom being like, like one of the main goals a lot of indie
hackers have and starting their businesses and there's like all these different types
of freedom.
Like the most common ones like financial freedom, like I don't want to have to work for somebody
else to earn my money.
I want to be able to make money however I want.
And then like time freedom, which is just like, I want to work on my own schedule whenever
I want.
Many days a year, a few days a year as I want.
And very few people like to your point Ben, like want to just retire and sit on a beach
and do nothing.
Like people just want to like, they still want to work.
They just want to control like when, when they work and how much they have to, which
is awesome.
But I think there's like these other types of freedom that are a little bit underrated,
like creative freedom, like working on whatever you want is really nice to have as a founder.
And then Derek, you're hinting at like, I think like people, like the ability to like,
like you have a job, you don't really choose your teammates that much, but when you run
a company, you can hire anyone you want.
You can be super nepotistic.
Like I hired my brother immediately when I joined Stripe.
I'm like, I'm not joining Stripe unless you guys hire my brother.
And like Patrick's like, well, I guess I did the same with my brother.
So it's like, all right, fine.
And like, that's super cool.
Like we sit on zoom and talk and my mom's like, who can I join and listen and she joins
and listens in.
And it's just like, this is great.
I could do this indefinitely.
And like, there's this concept of like work-life balance versus I think work-life integration
is the other sort of proposed thing.
And I like work-life integration.
I'm like, what if work doesn't even feel like work?
You know, what if I'm like shooting the shit with like my brother and my friends while
also working together in this cool challenge, you know, and you watch movies like, um, like
I don't know, any movie where you've got like all these experts, like working like Oceans
11 or something.
And it's like, these people are working together, but they're like friends and they're kind
of like a squad.
And nobody talks about doing that with their business, but like you can absolutely do that.
You can just like put together a team of people you really like have tough challenges you
go through together and it's way more rewarding.
Like to me, like that's addictive.
And so that's something I've been thinking about with Andy hackers too, like, okay, who
do I want to work with a lot and like actually just be friends with.
And I think that I don't want to manage a hundred people.
I don't want to manage 50 people, but like 10 people where we're all like super close
friends and like we all kind of buy into the mission and like, we're like super smart and
like talented and we enjoy working with each other.
Like that to me is the dream and I could do that indefinitely on almost any project.
Yeah.
That's, that's honestly been the new joy of running tuple these days is building the team
out and adding awesome people to it and having that sense of like, Oh, another amazing person
just joined this.
It's not a family, but you know, it's a, it's a collection, like we're a collection of people
and we're around a shared goal and it feels great.
And like, I've, I've always been someone who's really picky about people.
So I've been very selective about who I add to my friend group and who sticks around and
all that.
And this is like a mini world where it's like we control the gate at itself.
It's like we can, we could just shape this group of exactly how, how we want it.
It's pretty awesome.
Yeah.
Yeah.
My dad did this when I was a kid.
He was part of like this, I guess elite squad of furniture makers and it was just like eight
guys and then this big warehouse and my brother and I would go in to visit him as kids and
he was like the furniture finisher.
So they'd have all the furniture together and it would just look this ugly piece of
wood and he would just come in and like lacquer it and what, whatever he did and just made
it look beautiful.
All the different colors and stuff and he would also like, you know, make some furniture
for himself.
He'd make my mom these like beautiful jewelry boxes, but then everybody else in his squad
had like their own goal or their own like skill, you know, someone would like be kind
of the architect and like sketch out like, here's what the furniture is going to look
like.
And somebody would like, you know, I have no idea what the jobs are, but someone like
would cut it and they'd be so precise and they were all super good and they all trusted
each other and they would just be hired to like build this like really cool furniture.
Like Elton John had them like do his like living room in Atlanta and they had like all
this stuff and all these pictures of you so proud of showing me and it's just like, I
don't know.
I don't talk to very many people who've built that for themselves internally at their company,
you know, who have like this like very specialized team of people they really like to hang out
with.
And I think that takes time, you know, building that and like finding out how to get that
is hard.
One of the hard things is that like, you don't necessarily have the luxury to do that upfront.
Like upfront, you're just like, we need to survive, you know, our company isn't necessarily
profitable yet.
Like I got to hire like the absolute best person for the job that I can find.
And maybe that person is one of your friends and maybe you can convince them to leave their
job for you or something at that point in time.
And so I think that might be one of the reasons why it's tough.
Like maybe you have to start that way to really get there.
You know, like maybe I wouldn't be able to convince my brother to join me now, but because
I convinced him in the beginning, like he's here.
But I'm going to try.
Like that's, that's one of my goals of many.
Yeah.
I think even if you are, have the means to hire those people and, and are persuasive,
it's still hard because it's hard to really know if someone is going to fit and work correctly.
Like, like we've, we've had some people that we thought would that didn't like, I've, I've
messed this up several times already.
Of course.
We've had sort of had to continually edit the team and like also, or move people around
like like, Oh, we thought this was going to work well, but actually you should maybe be
over here and work with this person on this thing.
It's just, it's, it's, I think it's a really hard challenge.
Even when you're no, you can do like, no, you want that and like possibly can, can afford
it.
Yes.
It's like, it's, it's easier with friend groups because you just have fewer expectations
of friends.
I have like maybe one or two friends I've like really lost touch with are like, you
know, sort of removed from my life ever.
And I'm 34, but with like employees, the expectations are just so much higher for someone to do
a good job, to be consistent, et cetera, et cetera.
So it's like, yeah, I guess you do end up editing a lot more.
You can't just like stop, kind of, kind of stop talking to this employee, you know?
It's true.
It's true.
Or sit a friend down and say, you know, I've reached a new level of scale and I think we've
kind of, I've kind of outgrown you.
You don't quite fit anymore.
Good luck in your next venture, right?
With your next friendship.
Do you guys ever feel like, uh, like because you're sort of locked into your companies
that you're missing out on other things?
Like are you like, look at all this web three stuff.
Like I'm missing out, you know, or like, oh, if only I had this other idea, like the time
is right.
But I'm like, you know, I gotta finish what I've started.
You ever have any regrets?
I'm definitely still in the, I'm in the honeymoon phase of Savvy Cal.
Where like I know how difficult that first, like my last, my experience over the last
three years has been a primer, just a reminder on just how hard it is to get something off
the ground where you like the spark is lit.
You've started the small little fire that's going to grow into a much larger campfire.
And like, just to get that is so difficult because there's so many variables you're trying
to solve for like, is this the right solution for the right market and how do I reach that
market and on and on and on.
And now it feels like I've, I've figured out enough of those variables where like, okay,
we fixed, you know, eight of the 20 variables.
So now we can just work on optimizing other variables.
And so right now I'm like, okay, it's just starting to work.
I feel so relieved about that.
So I feel an immense sense of calm about that.
And like, man, I really don't want to go back to the beginning anytime soon.
Yeah, there's like an intense amount of focus that you need just to have things succeed.
And it's like, it's very easy to underestimate, but it's also like, I don't know, it's like,
there are times where I'm just like, if there's something interesting, like even like a side
project, I will feel sometimes guilty, like, Oh, I have this energy to spare.
Like shouldn't I be like putting this on my main thing?
Like, and I, I don't know if it's healthy, you know, like it is good to have diversity.
It's like probably helps prevent burnout and whatnot, but it almost feels like I'm cheating
on my girlfriend.
You know, it's like, I don't know if I should really be doing this, you know, and I wonder
if like, like, like, how do you feel?
Yeah.
And like with Tupel, I mean, like you've got a team.
Yeah, I know.
I feel that way with, with side project things for sure.
Like I worry about the message it would send for me to like, pour a decent amount of time
into anything else really, but I don't know at the same time, like side projects are kind
of what made Tupel a bigger success, I think like it was the small things I had launched
before where I learned, like cut my teeth on how to do this.
So I, I kind of think of side projects as education is like a pretty darn good habit
to keep going.
Yeah.
Back when I considered myself more of a software engineer, like my biggest issue was like every
time I started startup, like four years later, I'm just like, I have no idea what the state
of the art is with coding.
I'm still using what I started four years ago and like things have changed like dramatically.
Now I don't even care.
I've just given up.
I'm just like, all right, whatever.
I'm ancient and that's fine.
But I have to say like, I feel very like I kind of did a deep dive into this like web
three stuff after being a hater for so long and it's super interesting.
It's very, it's very mentally like compelling and engaging.
And there's a part of me that immediately started thinking like, okay, are there end
roads here to Andy hackers?
And then I was like, I did my sort of normal exercise, which is like, if I'm excited about
something, I will table it for a month or two and see if I'm still excited because otherwise
I'll just be like a crazy kid in a candy store, just bouncing around from aisle to aisle.
And it's been a couple months and I'm less excited about it.
I'm like, okay, maybe this is not the right approach.
I have other things to do first, but I'm still kind of excited about it.
And I see all these smart people working on all these cool projects that are like, I don't
know, they claim to be at the forefront of the next generation of the web.
And there's a part of me that feels like maybe they are, you know, and I feel the same way,
you know, like I feel like I'm ambitious, but it's very difficult to not, to not want
to jump into that kind of stuff and to not want to incorporate it.
And it's, it's underrated, you know, even if your startups four or five or six years
in, like you still have to focus, like it almost never goes away.
Yeah.
I see it as a gift to have something to be able to, to really focus in on hard that,
that I know has like the feedback loop is that things are working.
And so that to me is like, that is really important that for my brain to be happy is
like, I, I'm brushing this boulder forward and, and it's making progress.
And I think it's, it's definitely a different, for me, it's a different mental head space
to be in like, I'm just kind of playing in the sandbox.
You know, maybe if I were to dive into web three, it'd be just like wrapping my mind
around these different tools and experimenting and creating and putting stuff out, but there's
no actual like boulder being pushed.
But I could definitely see like in a different phase, like I think I would have to be in
a different phase where I could really embrace, you know, that kind of like playing in the
innovation sandbox.
But I think it's a, it looks like a lot of fun.
What about, I mean, what other like intellectual pursuits do you guys have outside of your businesses?
Like if any, you know, is it just like, for me, it's like, I would love to read more.
My brother reads all the time.
I feel like so guilty by comparison, because this guy's reading like two books a week.
And I'm like, I would love to do that.
I don't, but I've been focusing on like, having a more of a strategic approach to my personal
life lately and my dating life.
And that's been really fun.
But you know what I did?
That's, it's been like one of the best purchases of my life is I bought a karaoke machine,
which is literally just like a speaker with some cool LED lights and a few wireless mics.
And I plugged it into my TV, and now when friends come over, I put like YouTube karaoke
on my TV.
You can just like play whatever karaoke video you want on YouTube, and I forced them to
sing with me.
And it's amazing.
No matter how good or bad someone is at singing, it's always, you know, like maybe a beer too.
It's always super fun by the end of the night, and people never expect it to be that fun.
That's great.
I love that.
I went to a karaoke place in Hong Kong, I believe it was, and it's like the private
room style.
It's like you get your own setup, just like buyers, like it's like maybe 10 people.
That was that was a super fun version.
So it helps people get over the stage, right?
Right, exactly.
Because it's just your friends.
Yeah.
And you're like sometimes like you start off in a song and you're like, actually, no, this
is way too hard.
Nevermind.
I thought this is gonna be cool.
I'm out.
I have a list of karaoke songs on my phone.
Yeah, me too.
It's really like three lists.
And one list is like things I should try.
And then one list is like my go to songs, like these are songs that I know are good.
And the other list is called bad songs that seem like they'd be good, but are in fact
bad.
And these are the songs that I've tried and I was so confident in the beginning and I
just like could not finish like they're just too far out of my range or something.
So that's that's a great list to have.
It's good to crash and burn and learn from it and then write it down exactly write it
down.
So you don't forget because you'll just go back to those songs.
I think Billy Joel is that for me, we're like, I love his music and there's so many songs
I want to sing, but like he is just he's a tenor and I just have not.
And so this is just I just can't unfortunately, I have like there's like too many artists
for that stuff for me.
I love Adele can't sing any of her stuff.
I'm like, I like same Smith can't sing any of his stuff.
Like I like the strokes can't sing very much of it.
Yeah, I'd say for me, I'm I mean, I'm definitely the founder that can get extremely hyper obsessed
with like my business, which is probably not surprising.
A lot of us are that way, I think.
So like the struggle is to yeah, to like leave room for other intellectual pursuits outside
of like just pouring all my energy into my business.
Like I play the piano and I haven't really played much lately, but I would love to do
more of that.
You know, like I have I have a keyboard that I bought a couple of years ago.
It's not doesn't get touched very often.
So I'd love to do more of that.
And you know, reading is always something that I also want to do more of, but just never
make the time for and it's I've gotten frustrated with myself in years past, like setting goals,
you know, beginning of the year, like, all right, I'm gonna try to, you know, try to
build this this habit in.
And I've sort of come to embrace that, like, you know, there are certain seasons where
I'm just probably not going to be as diligent in these other areas, but something I keep,
I always want to keep checking in with myself on, like, are you getting too out of balance?
Because I think that's one of those things that can lead people to burn out and it can
sneak up on you before you even realize it, right?
I struggle with this because I'm like, yeah, I should be, I should live a balanced life,
right?
Like balance is so important.
And then like, I start doing it.
I'm like, oh, balance is so boring.
It's like the most boring thing ever, and you read like any biography of like anyone
who was just like, I don't know, had like a book written about them, like, they have
the most wildly imbalanced lives, they just go hard on something, you know, they're neglecting
some other thing.
It's not super sustainable, but we're all gonna die anyway, so that you don't have to
sustain it.
And it's just interesting, you know, and so some days, some weeks, I'm just like, I'm
gonna go to the gym, I'm gonna work out, you know, I'm gonna maintain my relationships
with friends and work a healthy amount and then step away from my computer and I do it.
And like, it does feel good, it's really nice.
But there's like this internal drive to like be out of balance, you know, sometimes you're
just like craving certain stuff.
So maybe there's like, I don't know, a formula for like, maintaining like, like the right
amount of imbalance, you know, like, to allow yourself to just like go hard, but like not
to the point to burnout, like just like just shy and then bring balance back in.
I haven't figured it out yet.
I'm just amusing.
I like that though.
I love that.
I find it really fun to obsess about Tupel, like people are like, oh, how many hours how
about like, so you're working crazy hours, like you're a startup person, you must work
crazy hours.
I'm like, not really.
I don't, I don't like do like, but in seat crazy hours.
But if you asked me like what percentage of time I'm thinking about a business thing,
it's a lot.
So it's like total hours of brain sweat is really high, but it's, but none of that feels
unfun to me.
Like I like to get obsessed with the thing and then just think about it a lot.
So yeah, that's the dream, like something you want to think about something you want
to talk about.
Yeah.
And it's just burning out like from that sort of work, that sort of effort.
So by the way, Derek, uh, one, one quick thing.
So just today I was opening up our old Slack instance.
So we moved to discord for like chat stuff, but we have, we have a Slack that's been around
for awhile and I went to our old Huzzah channel.
So we have a channel like posting wins and it's this record going back to like 2018 or
so of like really early Tupel wins and it's just like, it's just the three of us just
like posting like, I just like, look at this new subscription, $200 a month.
Oh my God.
Like it was, it was the time where we were, I was posting a screenshot of like every stripe
charge into the Huzzah channel, like a hundred dollars, $200 and like, we're all freaking
out.
Um, and like all the numbers, like we hit 50 calls today, like all the numbers like hilariously
small.
Um, and it was so like fun to just sit down, like, like, like scroll through that with
like Joel and Spencer.
So you're like about to like have another person on the team, totally recommend having
some sort of place that you can throw like happy like celebrations that you're going
to be able to keep and like someday look back on.
Yes, that's great.
We have a hooray channel that's uh, uh, but it's like, hasn't been used much.
There were a few old, like a year ago I posted like 4k MRR or something was like, and we
were like, Corey and I were celebrating and then we just haven't like kept that up, but
I'm definitely going to like reboot that channel.
And it's just so fun to have another person who's like spending their full time effort.
Like I'm, it's going to be a lot less lonely, not that I was like feeling super lonely before,
but it just, it's going to feel so good.
Yeah.
Teammate.
Totally.
I think it's going to be a big, a big change for you and a really positive one.
And the Huzzah channel, I think it's just a great practice because there's so many
inboxes and channels that like can have really bad news in them where it's like, you might
just open email and go, Oh God.
Yeah.
So it's nice to have one where every time you see the notification pop up, you're like,
yeah.
Yeah.
I love that.
It's fun.
Yeah.
That's kind of funny.
Things aren't intentional.
It's just like more likely there will be bad news, you know, you get sort of intentionally
design.
Okay.
This is a good news channel.
Exactly.
And it's, and then like other people started using it, which is cool.
Like other people are posting in design.
This is fun.
And like it almost becomes a way to keep tabs on different parts of the business.
Like engineering has like posted like some small bug was fixed or like this, like this
thorny problem that I'm working on is like now resolved or great message from my customer
like came in the customer support channel or we just closed a deal over here or like
this.
It's, it becomes almost like a heartbeat of the, the happy thing.
Yeah.
And it's great.
It's great to be able to celebrate what other people are excited about when at the moment
that they're excited about it, you know, which is something that's, you know, if you're not
delivered about that, it's especially with a remote team, it may not end up happening.
Right.
So someone's just having a little party of one in their own office, but not like to share
the joy, you know, totally.
It's the Huzzah channel is the gong ring of the distributed startup.
Yeah.
I love it.
It's like a company retreat band to make it like fun or cool or interesting.
Yeah.
That's a good question.
So we surveyed everybody and asked like, are like, what things have you done in other retreats
that like worked well?
Like, what would you like to see us do?
And the, the, not like the unanimous response back was like, we don't want to do any, you
know, structured corporate-y thing.
We just want to hang out with each other and like enjoy the social time.
And so we, we've scheduled nothing right now.
Like effect, like no awkward icebreakers.
Yeah.
And there's like a day kind of blocked off for like, okay, if we're going to, if people
want to ski or do like outdoor wintery activities, this is the day for that.
And then there's like a couple of days where it's just like, these are now like, you know,
explicitly not for that, but they're also not explicitly for anything.
It's like, we're going to be in the house hanging out.
We're going to like each, each of the founders like took an evening, like to cook a meal.
It's like each of us is responsible, like make dinner with the team one night, which
I think it's kind of fun.
But like it's basically, and then we have a ton of board games and card games and stuff
like that.
It's like a jokey machine.
I'm telling you.
It's a, it's a good idea.
I like it.
Um, I can see if I can get that shipped to Northern Vermont in a hurry.
This is how you can tell you're somewhere far away when the Amazon prime delivery times
are like five days.
Like how do people live like this?
But yeah, so, so I have some backup ideas.
Like if after the first day, it's like, actually we're kind of bored.
We could use a little structure.
So I have some ideas for things to do.
Like actually, actually scrolling through the Huzzah channel today, we were, we all
had the same thought.
Like it would be fun to pick out a couple of these and show people just like, this is
back when Spencer and Ben were really excited about a hundred dollars, like, or like, you
know, one new customer or, you know, hitting 50 calls and just might be kind of a fun to
sort of show.
Like this is 2019.
It's not that long ago.
Yeah.
Yeah.
I think it's going to be fun.
I'm, I'm totally an extrovert.
Like I'm, I'm Spencer says I'm a dog, like he's a cat and I'm a dog and like I super
ebb.
Like I'm just excited to have everybody in the house.
Like it's, I think it's going to be delightful.
How do you get everybody excited to come?
Cause like there have been times in the past and maybe I'm just not that much of a team
person.
I remember having like an internship in San Francisco when I was like, uh, God, I must
have been like 21, 20 years old or something.
And the team was always doing stuff like, yeah, we're going to the ball game, blah, blah,
blah.
And I was like, I'm out of here.
I'm going home to do my own thing.
Uh, maybe it's cause I was like so much younger than everybody, but I think it's, it's difficult
to get everybody like excited to see each other, especially with a remote company.
I bet.
Like, I mean, it's like people don't necessarily have like that close of friendships and relationships
and like a remote company.
Yeah.
We'll see.
I don't know.
I'm not sure if everyone actually is excited.
I think, I think we've, we've all agreed.
Everyone agreed.
Like, we'll see what the vibe is like when they get here.
I think, um, I think culturally we sort of hired for people that are interested in like
social interaction.
Like we have a team that I would describe the team as, as warm.
And so like we've, we've hired people that have some of that, that warmth, like they,
they, they like interactions, they value other people, they, they take some joy from that.
And so I think we've kind of built a group that is fairly wired for that, but, but we'll
see.
Cool.
Best of luck.
Let me know how it goes.
Thanks.
Yeah.
All right.