What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
On this show, I talk to the founders of profitable internet businesses, and I try to get a sense
of what it's like to be in their shoes.
How do they get to where they are today?
How do they make decisions, both with their companies and in their personal lives?
And what exactly makes their businesses tick?
And the goal here, as always, is so that the rest of us can learn from their examples and
go on to build our own profitable internet businesses.
Today we're going to discuss a very important topic, work-life balance and productivity
as a founder.
And joining me are two very special guests.
Neither of them needs an introduction, but they both certainly deserve one.
Natalie Nagel is a former guest on the IndieHackers podcast.
You might remember her from episode number 90, which is one of my favorites.
Natalie is the CEO and founder of Wildbit, a bootstrapped and profitable software business
with unusual longevity.
She's been doing this for 20 years now and generates many millions of dollars in revenue
for multiple products, including Postmark, which I happen to think is the best transactional
email service.
I use it for IndieHackers to send millions of emails every month.
So Natalie, thank you for Postmark, and welcome back to the show.
Thanks, Courtland.
I'm so excited to be here.
We are also joined by David Hahnemeyer-Hansen, better known by many as DHH on the internet.
David is the founder and CTO of Basecamp, another bootstrapped and profitable software
business that does many millions in revenue and has been influential for decades.
David is also the creator of Ruby on Rails, the popular programming framework.
He's a New York Times bestselling author.
He's a professional race car driver who took first place in his class at the 24 Hours of
Le Mans.
He is also one of the primary reasons why IndieHackers exists.
I can say, without a doubt, there would be no IndieHackers if David's talks and his
writings that inspired me 11 or 12 years ago had not happened.
So David, thank you for the inspiration, and welcome to the show.
Well, you're too kind, and thanks for having me here.
I can't wait to talk about this.
Yeah, let's jump right in.
David, you are an outspoken critic of the hustle culture that has almost become traditional
wisdom in the tech industry, which is that if you want to build a company, it's hard.
And it's so hard, in fact, that success requires going through the grind and putting in excessive
hours.
What's wrong with this picture and your view?
Well, it started with just my own personal experience, which was, one, I could not recognize
in that image.
When we started Basecamp back in 2003, we sort of went the other way around.
Basecamp started as a side project.
So rather than pouring in like twice the normal working hours, we poured in about a fourth
or third of the normal working hours.
The version of Basecamp that still operates today for tens of thousands of happy customers
that have been around for 16 years and made over a quarter of a billion dollars was written
on 10 hours a week.
That was how much time I dedicated to sort of the technical underpinnings of the system
when we got started.
And I thought when I transitioned from working 10 hours a week to 40 hours a week, that holy
shit, what am I going to do with all this time?
40 hours a week seemed like such an enormous amount of time to someone who had gone to
company business school, had other clients, and then we did this thing on the side.
So transitioning into the 40-hour work week was already a bit of an abrupt or harsh transition.
And one where I thought there was just plenty of time.
I couldn't even use 40 hours a week.
I still can't, seriously.
When I look at my day-to-day, I can't use 40 hours productively in sort of the sense
of can I work creatively for 40 hours a week?
Absolutely not.
I can work creatively.
A great day for me, a wonderful day, a home run day, is four to five hours of concerted
creative effort, deep work, deep thinking, programming, that kind of stuff.
And then there's still hours left over to do all the other stuff, to send email, to
talk to the team, to figure out what we should do next.
So when I hear these stories, and they're not even really stories.
They're posted as requirements.
When I hear these requirements, that unless you work 80 hours a week, unless you do all
this, you're bound to fail, you're not really serious, you're just running a lifestyle business,
all these are the bullshit derogatory terms for working sane, reasonable hours.
The amount of hours that workers fought very long and very hard to be able to secure this
idea of eight hours for work, eight hours for play, and eight hours for sleep.
I didn't make that shit up.
It wasn't like a DHH invention that we should work 40-hour work weeks.
That was just established conventional wisdom for a good reason.
First, it was studied ad nauseam by all sorts of people in the business world, and not for
benign reasons.
They were studied for productivity reasons, like the example I always give is Henry Ford
putting together his assembly line going, do you know what, 40 hours a week is the right
number of hours.
If I make workers work 50 hours a week, I get cars that are broken and need to be returned
and need to be fixed.
And if we work 40 hours a week, do you know what, that kind of pans out.
So I'm just leaning on that.
No inventions here, nothing great insight.
Just leaning on the fact that first of all, this was what we did for about 70 years in
terms of executive approach to business.
And then I grew up in a country called Denmark where no one worked 80-hour weeks.
Literally I knew no one.
Number is zero of the number of people until I was about in my early to mid-20s and I started
hearing about siliconvalley.com, boom, I never heard of these ways of working.
So to hear that that's a requirement to start a business, it just bounced off my skull.
That is obviously preposterous.
And then to hear people actually believe it, I just went, I mean, this is bananas.
And this sense of this is bananas was actually more or less the title of our latest book.
It doesn't have to be crazy at work.
It could have been called, it doesn't have to be bananas.
It doesn't have to be crazy at work.
And we put forward an idea, basically just recounting our own experience.
Hey, you can work 40 hours a week, you can build a great business that does hundreds
of millions of dollars in revenue or less.
That's not even an interesting bar to me, just this permission really to say, you can
be an entrepreneur, you can be a startup person and also have other things in your life.
For a while, one of the things that inspired the book was I kept seeing these tweets, like,
if you want to be a successful startup founder, you got to pick two out of five, either you
can sleep or you can exercise or you can have like a life or you're going to crush it at
business.
And I just went like, this is so stupid, like literally stupid as in dumb, unintelligent.
And I just, I can't stand it.
So all right, I'll just stop there.
I don't have any voices that's going to be so disappointing.
It's funny, you said you max out at four to five hours of creative work, right?
One of the things that we obsess about on our team is the ability to really allow our
team to maximize the time when they can get that deep work done, like that's my everything,
my whole brain functions around this.
And the science shows there's no more than you can't do.
The best brains in the world can't do more than four hours.
Your people who think for a living, your writers, your creatives, they can't do more than four
hours.
And it's actually why we ended up with a 32-hour workweek because we were like, well, what
the hell are we doing for the rest of the time?
How much meetings do you have?
How many things do you actually need to do outside of your work that you're hired to
do this deep work, this unique ability that we all have as knowledge workers?
And I think for the most part, I don't disagree with anything that you've said.
I think that the big challenge that I have from our experience is that in the early days,
without the support of a team, I think starting a business to us was, I don't think we could
have done it in 10 hours, that's for sure, but 40 was really, really, really tough in
the early days because of just this pure, this simple math of like, we have to write
the code.
We're not writing the code, but we have to build the software, design the software, think
about the market, and then support our customers.
And I think that support piece is where we always found ourselves shifting past anything
that resembled a nine to five was because you spend most of the day, we've always had
small teams, neither Chris nor I write code ourselves, but they were tiny teams.
And so it was like, you guys focus on this, focus on supporting it, it's going down, make
sure it doesn't go down anymore.
And then it's like, all right, let's go have dinner and I'll come back and I'll do support
now because I want to make sure our cut and we love your, you love your first customers.
Right?
So I guess, David, I just would love to know, like in the early days, how did you guys pull
that off?
Because I remember one of the things that, so we've been base cam customers since I think
the very beginning.
I don't, I asked Chris this morning and he said, I think we were like number, I don't
know, like 800 or something, something early, early, early.
And you know, to Cortland's point, while that would not have existed if it wasn't for 37
signals.
But I think one of the things that we always found so inspirational in the early days was
we, you know, if you email support, you get a response from Jason.
And that was like, so, you know, it didn't matter.
Sometimes it would be like at night, sometimes on the, you know, and so I guess just maybe
you can help me figure it out because that was always one of the things that I felt like
I don't know how we would find all the time to do all the things that were important and
still do it in less than a 40 hour work week.
I think that's a, that's a great point because Jason did support at base cam for the first
three years.
It took three years before we hired someone else.
And that was at the end, he was answering, I think 150 or 160 emails a day on support.
And part of this was setting expectations and I'll give you a brief story.
I recently had to deal with two lawyers at the same time, one lawyer in Denmark about
some family business and one lawyer in New York about some real estate there.
The lawyer in New York, the first call guy goes out of his way to say, do you know what?
I'm going on vacation, but don't worry, it doesn't matter.
You can call me 24 seven.
Here's my personal cell phone number.
I always pick up whatever it is.
I wasn't on trial for murder.
Like I was buying a piece of real estate, right?
Like it totally did not matter.
There was absolutely zero urgency.
I asked for zero urgency.
I wasn't like, Hey dude, so are you going to be available 24 seven?
This guy offers up on his own.
I'm available 24 seven.
There are no boundaries.
My life is your life.
Then I talked to the lawyer in Denmark and there we actually had a little bit more pressing
thing.
I forget what it was, but it, this is like Thursday afternoon and he's like, all right.
Just want to tell you I'm out tomorrow and I'm out on the weekend and we can pick this
up on Monday.
And like the contrast between those two things was amazing.
And you know what?
I had more respect for the second guy.
I had more respect for the Danish lawyer who simply said, do you know what?
It's almost four 30.
I got to pick up my kids and we'll talk about it on Monday.
Do you know what?
That was totally fine.
He set the realistic expectations.
And I think that there's so much of this sense of like how much time we have to put in, how
much we love our customers.
We're just not setting boundaries and we could.
And that's what Jason did in large parts in the early days.
He would sometimes answer late at night because he'd been out all day.
Right?
Like there was not a 15 minute response time in the early days for, if you caught Jason
while he was at the keyboard, yeah, you'd get an answer right away.
It'd usually be very short.
And if it was a free to request, the answer would be even shorter.
It'd just be the word no.
And then, I remember those days.
So it was sort of just a different approach, but it was an approach that was targeted towards,
do you know what?
I'm not going to let this consume my life.
Customers are important.
Early customers are even more important, but they will still respect you, even if you have
boundaries for your life.
And we just found that over and over again that whatever pushback we would get from someone
like, hey, I've been waiting a little.
It was such a small percentage.
There's so much of this we put on ourselves, not because customers require it, not because
it's required for business, because we believe that we have to do this.
And it's simply false.
I'll give you another really quick story, which was before we started doing product
development, Jason would do consulting work.
And at the time, dot com, boom, the normal approach was you get a request for proposal,
and Jason would send back the standard proposal, and that'd be like 25 pages.
And one time he went like, why am I wasting my time writing 25 pages?
No one reads this shit.
Let me just try 12.
So he cut it down to 12.
Same business.
No one canceled.
No one didn't go through the contract.
So let's try that again.
Six pages.
Nothing.
Three pages.
Nothing.
One page.
That was where it ended up.
We used to do one page proposals.
That's all we did.
We wouldn't do them if they were single page longer.
Exactly.
And that was the insight.
Customers just cared how much is it going to cost?
How long is it going to take?
All the other stuff about, am I going to hire you or not hire you?
That was long since decided.
So I think there's so many of these shortcuts we can take if we allow ourselves to do it.
And I think part of that goes with you also have to love yourself.
And I don't mean that in an egotistical way, but sort of in an Eric from kind of you have
to have confidence in yourself that saying, I'm also a human being.
I'm also worth sort of recovering.
It's worth spending time on the weekends and something else.
And in fact, I'm both a better support person.
I'm a better product person.
I'm a better software engineer.
I'm a better writer.
If I take the time to step away from the work and that the recovery time is just as important
as the activity time, if you want to do well.
A hundred percent.
I mean, the recovery is everything.
I guess the part that I'm challenged with is I look at businesses as kind of seasonal,
you know, and then you have these like early days and then you get the privilege of having
people that work for you, right?
You get the privilege of having a larger team and then like these things become easier.
Obviously the more support you have, profitability helps.
But if you like, if I started today and I say this all the time, like, I think we scared
to death to start today because the world is so different from when it was, you know,
our oldest product is 14 years old too.
And so it's like, I don't know that I could pull it off because it is noisier and it's
harder to get it out there.
And you know, without an existing audience, I'd have to build something new and do all
these things.
I think to me, working less is like a goal just in a way as productivity is a goal, right?
And I would say that if I was, you know, starting out, let's say I wasn't 17, 18 years old and
I had kids and a mortgage and all these things and you're chasing profitability and I think
a lot of Cortland's listeners are kind of in this in-between phase that they have jobs,
but they also have this thing they want to do.
And at some point there's going to be that flip, right?
At some point the side project just does enough to just cover it, right?
To just get them to that point where like, I think I can do it.
I think I can jump.
I think I can become an entrepreneur without having this other thing that's paying the
bills.
But that's like the starting point.
That's the scariest shit place to be because you're not profitable, right?
You're barely making do.
And now it's chasing that real true like calm and the ability to create this thing that
it sustains you and doesn't just like suck all the energy out of you.
And I do think, at least in my experience, and I try to spend a lot of time with non-software
founders because just like you, I can't stand the noise.
It tortures me.
And so I like to spend time with people like I have a group that I meet with every month.
It's like manufacturing and car dealers, all kinds of stuff that's not software.
And they have similar experiences, right?
There's like that initial season of a business where it is a shit ton of work.
It's like you're just chasing that profitability.
You're chasing this ability to be calm and be restful, but it takes a while.
And I do.
I agree with everything you say, and my whole company is like everything we do is especially
for the team to sustain this piece and this ability to create a space for deep work.
But I don't know, as an entrepreneur, that wasn't my experience.
Early on, it was you just take a deep breath and you're like, let's keep running and let's
just get it to profitability and let's make sure it supports our family and let's make
sure it supports our team and let's protect the team.
I mean, that's another thing I think we should talk about or at least think about.
Those early days for us were a lot of picking up the slack, so the team got their 40 hours.
I don't want them working a minute over 40.
And so there was slack to pick up just in the way that, I don't know, I mean, maybe
the answer is, well, I could have set boundaries, but I also think some of that is that motivation
and that desire and that excitement of starting something new and wanting to get it to profitability
as fast as possible so you can't hire that next person that's going to help, you know,
hire your first support person, hire somebody who's going to be on call to help you out
so you're not on call in 24 hours, seven days, you know, I build infrastructure products.
It's a little bit different.
But I do think that there is, there's a space in there, right?
We should be chasing that calm and those, I mean, I don't want to work 40 hours.
I don't work 40 hours.
I don't even want to work 32 hours, to be honest with you.
I want to work a lot less than that.
But that's a privilege, right?
That's privilege of having a team supporting me.
That's privilege of massive profits that sustain me, right?
That's privilege of having products that, you know, I have a lot of products.
So they give me some security and low risk tolerance.
But there is that moment, those early days where I just think it's hard and I don't,
I don't see working more than 40 hours as some kind of failure.
I think promoting 80 hour work weeks, we, you and I are in a hundred percent agreement
that like that hustle porn stuff is not interesting and it's dumb and it's a bunch of sorry, mostly
white men who that's how they support themselves to feel good, right?
That's how they make themselves feel big and powerful and strong by saying, I work more
hours than you work, even though the hours are stupid and they're not accomplishing anything.
But I think for the non 80 hours, there is that moment in time when you really need,
you just, you're just pushing, you're pushing hard to get it to that place where it's stable.
I think that totally encapsulates the healthy anxieties that a lot of entrepreneurs sit
with.
I don't want to push back on it nonetheless, because first of all, it wasn't our experience
and it is possible that we have a completely unique experience, but I don't think so.
And the reason why I say that was, again, I grew up in a country, Denmark, where I knew
some entrepreneurs, they didn't work materially different, whether they were bakers or whether
they were sort of general contractors or whether they were something else.
There was just a core, I think internalized respect for the boundary of the 40 hour from
a social perspective, not necessarily because they invented it, no, they just lived and
worked in an environment, in a society that had decided that there was no glory in work
beyond that.
Now, that's not quite what you're talking about.
I totally agree with you that there's a difference between sort of feeling just personally glorious
because you're putting in all this and it's about exhibitionism and about these other
things.
The internal side of it, which is sort of, I should say, the chase.
To some degrees, I think there are flip sides of a similar addiction, of a similar addiction
to the rush of the start of the work of chasing, I should say.
I think that word is interesting because that word was never something that came up for
us, for me, like the chase.
That sense of I have to fight before I can get too calm strikes me as just one path.
There's also a path where you can start, as we did, Basecamp was a side project and we
weren't in a chase.
We weren't in a rush.
We waited more than a year for Basecamp to be sort of well enough for us to switch over
and it wasn't sort of hanging on by our fingernails.
The reason we waited a whole year, we could probably have switched over to Basecamp like,
I don't know, after three months.
You think that you're just at the limit, we can just barely kind of make expenses or whatever.
We waited until there was enough.
There was sort of buffer enough that it didn't feel like an existential fight.
And then the chase from there was also not a chase.
The time it took us to go from the four employees that went full-time on Basecamp to I think
the 10 employees we had, I don't know, I'm trying to remember the timeline here, like
four years later.
You can see that there was no chase.
We weren't in a rush to add more employees, which meant that every step of the way, it
was pretty calm.
We were paying ourselves normal salaries, we were paying people normal salaries.
We were working normal hours.
We were setting habits, we were choosing habits and we were cultivating habits that felt sort
of authentic to this idea that we're going to do our damn best work in those four hours
a day.
Yeah.
And then there's just stuff otherwise too.
I don't want to sort of sound that glib about it.
But I also want to say like running a company of say four people, two of them were Jason
and I, right?
Like there were two employees and then they're Jason and I.
It's just not that much work on the organizational side, for example.
In fact, I would arrest saying it gets easier.
For me, it's gotten harder.
Like the early days, much easier for me in terms of...
I'd love Jason's perspective on that.
I'm pretty...
Actually, I took it from him.
It's his glib of response that it only gets harder.
That has literally been our experience.
I'll take that.
But let me ask you this then, because I think this is where I struggle because I don't remember
like chaos in the early...
That's not what I remember.
I remember this motivation, this intense desire to do this thing.
I think...
Yes.
I remember because you and Jason have built this incredible business and also this incredible
following based on your ability to create these moments.
I mean, you're on Twitter, you're writing books, you're doing all these things.
You are chasing something as well, right?
It's just defined in a different way.
And I think entrepreneurs, by their nature, you start something because you have this
audacity to believe that you can do this thing, right?
Like our brains are wired differently.
They're not better.
They're not worse.
They're just different.
And I do think that it is a chase, but it's also this...
You commit to something.
It's like if I was a violinist, I would practice...
And trying to be really spectacular and I would practice like a crazy person because
it's built in my brain to just continue to evolve.
I don't support the idea that we want to run this way forever, but I do want to acknowledge
the founders that are starting out that are like, I go to sleep and I wake up thinking
of this thing, right?
It's like I'm in this...
I'm thinking of it when I'm putting my kids to bed and trying hard as shit to turn it
off.
But I'm excited.
It's part of my DNA.
It's part of who I am as a person.
And even now, working 32 hours a week, right, I still...
It's...
Chris and I go on vacation together and we have the luxury of being husband and wife
and also co-founders, right?
And we're sitting on vacation.
We're like, we're not going to talk about work.
We're not going to talk about work.
But can we talk about work?
And it's exciting.
And it's fun.
And it's simultaneously a personal fulfillment to me and also this thing, this project that
we're working on that's really exciting and these people that I love.
And maybe that's why I don't see 40 hours.
I might not have been in front of a computer or sitting at my desk, but my brain is thinking
about this business.
And I think a lot of entrepreneurs will say, like, that can't be bad because it isn't...
This is how we're wired.
Like this is...
There's people who think about other things and we can have hobbies and Chris has lots
of hobbies.
I know you have hobbies, you know, like all these things.
But it is...
It's this desire to do this thing.
And that's just...
For me, that's also could be...I mean, maybe that isn't work how you define it.
But to me, that's work.
That's still this like, I need to go away on a beach somewhere for a couple of days
and legit retrashing novels to like stop thinking about work.
But it's work.
And I think it's okay to work longer hours in the beginning and just strive for a balance
or a harmony of those two things, but to acknowledge that entrepreneurship is...it's an obsession.
It's a passion.
It's an incredible motivation to build something.
I think that's totally fair.
But then let's draw the line between what's sort of required and just what we want to
do.
There are entrepreneurs who just want to work more hours.
You and I agree on that a hundred percent.
You and I agree on that.
The whole, you can't build it without working 80 hours is bullshit.
And I know that.
And I mean, especially if you realize that in the early days, what everybody realized,
everybody has the same kind of trajectories through business, right?
They start off and they're just like getting shit done.
And then at some point realize, I got to get out of the business and think about the business
from a high level.
And I can't do that if I'm hustling or whatever for 40 hours a week, right?
We have to get out of it anyway.
I tell my team, you pay me to think, you don't pay me to sit there and do support because
I'm not useful that way, right?
So a hundred percent.
To do the business, to grow the business, to do something special, to have meaningful
work, I got to get out of it, right?
But in the early days, I can.
Who's going to do that work for me?
I would pause it again.
The work doesn't...
The work you think needs to be done often does just not need to be done.
The lawyer that says, I'm available 24-7 and you can call me at a time.
He clearly thinks of himself like, I'm doing important work here.
When I take a call on Saturday, that's just to keep a client.
I wouldn't keep it otherwise.
We start telling ourselves all these stories about what's required and what's necessary.
And the reason I think I come at this with a different perspective is I literally grew
up in a society where this didn't happen.
So this is why I reject the notion that this is in the DNA.
I don't actually think entrepreneurs are that special.
I think they get molded from social pressures in all sorts of ways.
And I think the American pressures that mold people are particularly harmful.
If you compare them to sort of entrepreneurs from other areas of the world, like, do you
know what?
The Danes are no smarter.
They're no lazier.
They're no...
None of these things, right?
Like the natural percentage of, say, entrepreneurial DNA, I would think is probably the same in Denmark
or as it is in the US.
Maybe there's some sort of bloodline, whatever.
But you end up with completely different experiences.
And I think this is why sort of comparing cultures is such an important thing to do.
And I think one of the blessings that I've had have been living in three very different
countries for sustained periods of time.
I lived in Denmark for 25 years.
I lived in the US for 15 years, and I lived in Spain for 10 years.
And just those experiences taught me that, like, I'll tell you, the Spanish approach
entrepreneurship very, very, very differently than the Americans, right?
Yet Spanish businesses exist, Spanish society exist, like all these things exist.
And it's also sort of me just looking at the three different cultures.
I think it's fair to have valued judgments about that.
I think Americans are doing it wrong, right?
On the grand scheme, I think the grand narrative about entrepreneurship in America is, in my
opinion, severely worse than the one that exists in, say, Denmark or in Spain on all
the levels, not just on an individual level for the entrepreneur, but for the people who
work for that entrepreneur.
Because one of the things I keep hearing, and I trust you 100% in your intentions on
this, is, you know what, the entrepreneurs can work 80 hour weeks or 100 hour weeks or
whatever, but they'll shield all of that from the employees and the employees will just
work 40 hour weeks.
I don't believe that.
I literally don't.
I think workaholism trickles down.
And I think the sort of ambitious employees who see what the boss does, they'll see what
the boss does, not what they say.
So if you say, do you know what, working 40 hours a week and sustainable hours, it's really
important to me, yet meanwhile, you're obviously working 80 hour plus weeks.
People just go like, yeah, do you know what, that's just for show.
That's essentially bullshit.
And I need to internalize that if I'm going to sort of get ahead here, I should model
what my boss is doing.
That whole sort of psychology and power dynamic, of course, is also not something I'm observing
or inventing.
This is just established organizational psychology, right?
There's modeling going on.
And the way you actually build culture is not by what you say, it's what you do.
And all these other factors to it that I think leads up to the fact that it's very difficult
slash impossible to have an entrepreneur, have a boss that puts in twice the amount
of work than the workers do.
Even if you on the surface say, this is not what I want for you.
You could still say, of course, well, in the early days, I didn't even have employees.
So before we have employees, we're going to go bananas, we're going to work 80 hour weeks,
we're going to do all the things that sort of need to be done.
And yet even still, I take sort of objection to that.
I think the habits you form in the early days are incredibly hard to shake.
And they really form these organizational grooves.
They can be redirected and you can retrain them, but it's very hard.
And it's much easier to simply go into it, thinking, I'm going to build a business that
is sustainable in terms of profitability, in terms of how it's worked, in terms of our
relationship with employees and with customers, and we'll have boundaries on day one.
I don't believe that there's this phase you have to go through where everything is, whether
it's crazy or not, everything is 80 hour weeks, or we don't have boundaries, or we don't have
these things.
I mean, in magic land afterwards, where you can do all these things, I don't think that's
a...
I think we get what we've been getting by the approach we've been taking.
You absolutely describe the dominant approach to business on the healthy side.
Well, healthy, we're having a discussion about that.
Not on the performative, like, oh, I'm so good because I work 80 hour weeks.
No, no, no, just on the internalized perception that entrepreneurs in the US have about what's
required.
So that's why I can't commit to this license that basically says like, no, no, you're actually
doing it right.
If you are working 80 hours a week, this is all good.
This is okay.
I don't think it is.
Again, I'm just me here, I'm talking anecdotal data based on my experience in the US, and
then my experience watching entire societies structured like this, and saying, I don't
think it's necessary.
And I think getting to the point where what's actually important, we have so much focus
on like, how many hours do we work, and so little focus on how well we spend the time.
So our entire project at Basecamp, and you mentioned this at the beginning too, has been
how can we spend the hours that we have better?
Because there's such a lack of focus on making just the eight hours count.
I want to jump in here for just a second, David, because you're talking about something
important, which is that in the early days, instead of just working as many hours as possible
and working on everything, it's better to identify what actually matters, cut out the
cruft, and just spend your time on the important stuff.
And I think that's obviously great advice, if you can do it, I talked to a lot of early
stage founders, it's their very first time being an indie hacker, they've never started
anything before.
And they're not sure which of their efforts are going to pay off, what's a waste of time,
what's important to work on.
And quite frankly, you know, I tracked my time when I was working on indie hackers,
I had a few 60 hour weeks in the early days, and that's because I also wasn't 100% sure.
There are lots of things I thought were going to pay off that didn't.
There are things that I wasn't that confident about, that actually ended up being very important.
Do you think it's realistic to expect early stage founders to not work as many hours and
to be able to identify exactly what's worth working on?
Yes.
I mean, I'm going to go kind of hardline on this simply, in part to play the counter melody
to the dominant narrative, but also because it's legitimately what I believe, and it's
legitimately what I've lived and it's legitimately what I've observed.
I think the problem here is thinking, like, first of all, that you can't figure out what
the right things are, or you can't analyze your time.
A great book that I found is called The Effective Executive, I think it's from like the 60s or
the 70s or something like that.
One of the key points it takes out is don't just track your hours, track what you spent
your time on.
Let's say you work 60 hours, and you break that down and you see where does the time
go?
Let's just take a hypothetical 60 hours here.
Well, I spent like 20 hours, I don't know, networking, going out to coffee meetings or
I don't think that's what Cortland was doing.
I'm probably writing code.
I actually did break down my time by category.
Well, then I'm fascinated to hear what your breakdown are, and I'd be very willing to
critique the breakdown of what you could cut.
Before we get into the specifics of that, I'll just say, this is something that can
be communicated.
You can have a fair discussion and you can learn from other people about what are valuable
things to spend your time on.
Let's take code, for example.
Is it valuable to try to squeeze eight-hour coding sessions out of every day for seven
days a week?
The research on that one is just universally clear.
No, does not work, is less productive, will end you up with more bugs and more rework
and all these other things, which is why I really like to program.
It's literally in my top three things.
I program an inordinate amount of time for someone in my position at a company like ours
simply because I love it.
There's very few other things that we do at Basecamp that I enjoy more than programming,
something that sort of engages me.
Yet, even with that, with all that passion, with all that energy, with all that sort of
interest in the programming, I realize I hit that wall after the four or five hours and
I don't try to squeeze blood from a stone.
I accept.
Do you know what?
That was a good day's work.
I'm not done and I'll go back to it tomorrow and I'll be giddy about getting back into
the editor and getting back into it, but also just say like, hey, that was four hours very
well spent.
I'll spend the rest of the time on something else, like talking on a podcast or whatever.
My basic kind of calendar has not changed in 20 years.
I will start my mornings doing stuff like this, entering email, tweeting, reading, whatever,
and then around noon, I'll realize, all right, now it's usually after lunch, I'll get into
the deep work and I'll have my four hours after that to do that deep work.
Again, I accept that in the US, we look like freaks.
We look like weird outliers that are spewing completely unrealistic expectations of what
you can actually do as an entrepreneur.
That's a societal critique.
The fact that we are an outlier and that it feels so unrealistic that you can spend just
40 hours a week on your business in the early days is a societal critique.
I'm just here bringing the message.
It's not widely distributed.
There are entire societies that are structured differently and do not go through this.
I think that's just worth some reflection.
You can go like, how is it that you can have a rich, prosperous society like the Scandinavian
countries or you can have Spain who's even on the other end of the spectrum of how many
hours you should be working every day, and yet they're flourishing.
They have good lives, they do creative things, they invent things, they do things like, how
is this possible?
Then I think you should just use that as an opening, that we're not discussing Martians.
This is not invented peoples.
These are actual different ways of doing it.
We look so weird at 37signals simply because we are importing a European slash Scandinavian
tradition into American work culture.
I'm not from America, actually.
I don't know if you knew that, but I was actually born in Russia.
I have a little bit of another culture to also base things off of, so it's not purely
American, although I wouldn't say that I very much admire the Russian work ethic, but they
work hard as shit.
Now, I think to Cortland's question, and I think it was a really important one, is there
is, I don't know that I could have given you an answer, I believe, and I don't know if
David, you agree with me, but when we started off, when you guys started off, we had the
privilege and the luck of being able to do what we did because the market was extremely
different back then.
If we're really talking about these businesses that we've built, these SaaS businesses that
we launched, and I think you guys wrote a blog post about it, and that was monumental
for us because there was a SaaS product launching maybe once a week, maybe once a month.
There was no product hunt.
There was none of that stuff, and that's privilege.
To have these conversations now to say that the way that we did things before is the same
way you can do it now 20 years later feels like a privileged perspective to me.
I don't argue.
I don't know anything.
I've never lived in Denmark.
I don't know anything about that culture except what you share, but I do think that we are
to Cortland's question.
In this country right now, I agree that we have big issues with how we treat people,
how we treat employees, how we view these things, but I do think we're speaking in absolutes.
It's either you build a business working 10 hours a week or it's 80 hours a week, and
I think I live more in the middle where I say there's a 60-hour week and you're not
a bad person.
You're not stupid for doing that, but you're like, I don't know what's going to work or
you're trying to focus on this and on this at the same time.
If we spoke more in aspirations to say, we agree with David.
We agree that and end Jason and base camp and this idea that we should create balance
and we should be working on the right things and we should have clarity of thought and
as entrepreneurs, we should be emulating behavior we want to see on our teams, all these things.
I agree with you on all of them, but for these people who are just starting off, I think
there is this question.
It's much clearer to you now in hindsight to say, what was the right thing to work on?
I can tell you right now that even some days today, I'm like, I think this is the right
thing, but I have the privilege of tons of money behind me.
30 people, tons of money.
If I screw one up, it's going to be okay.
I was saying the other day, a boot shaft business is invincible to some degree.
I don't bet the farm.
It's a beautiful thing.
I can take risks all day long.
I can launch products.
I don't work out.
It's okay, and all these things, but that's a lucky place to be in.
If I came and told a person right now, hey, look at me.
I'm doing great.
Everything's good.
I'm doing less than 32 hours a week.
They don't have the support.
I've done that.
I've had talks.
I've gone on stage and had these conversations.
People come to me and say, Natalie, that's amazing, but what do I do?
I don't know what you do.
I don't know what the right answer is.
I don't know.
I met a woman who started a pharmaceutical company.
She worked in Big Pharma and realized that most pharmaceutical companies are owned by
white men.
When it comes to drugs for women, it doesn't process.
The way that they cured ailments in women, it just doesn't process.
Anyway, she goes and she starts this totally new pharmaceutical company that's focused
on creating drugs for women, delivering them in a means that makes sense and not the way
... This is an immense amount of project that she's working on.
This is going to be, if it succeeds, really life-changing for women, for the industry,
and all these things.
She's passionate about it, she's excited about it, and she works so hard.
I've talked to her about it, but she's got older kids, and she's like, you know what?
This is my life right now, and I'm so excited to make an impact and make a change.
Would you say to her that she's wrong, or she's doing it wrong?
I look at her and I think, holy crap, you're changing lives, and that email isn't a wonderful
thing.
I built software for email.
I tell my team here, yeah, we don't want to save lives here.
She is, and she's working like a madwoman.
I don't know.
I don't think that makes her less than, or not smart enough, or a poor entrepreneur.
I think that's just a person who's passionate and excited about something she wants to get
done, and she's going to accomplish it.
I don't know.
Could she accomplish it working 20 hours a week?
Probably not.
I think an important thing to start with is to divorce our feelings of worth as humans
from how we work.
It's possible to be a wonderful human and work in very ineffective ways.
I'm not saying that's true of this story you say.
If we start by divorcing this thing that good people can work in bad ways that make them
less effective, that to me doesn't strike me as profoundly controversial of a statement.
I know lots of people who are good people who, for whatever reason, don't have the most
effective work practices.
That doesn't take anything away from the mission, from who they are, or whatever.
I also know, in fact, prime critique of mindfulness and life hacking and whatever is that it's
completely divorced from ethics.
Say someone who's a, I don't know, exploitive hedge fund manager, whatever bogeyman we can
come up with, if we train that person to simply have good effective work habits, you can have
a quote unquote bad person who have very effective work habits and they're therefore very good
at what they do.
What they do is just terrible.
These configurations are all possible.
If we divorce this sense of worth from someone, like are they a good human or whatever from
how they work, I think it's possible for us to engage a productive conversation where
we can say, like, amazing mission you have.
Have you thought about how you work?
The executive is one of those books, right?
It attacks directly this notion that just because we put in a bunch of hours, that means
that those hours count, or that they're great.
They may not be.
I don't know anything about the particulars, but as with anything, I think we should examine
them.
Because isn't it even more important that if someone has sort of a world changing, hugely
aspirational mission, that they are as best equipped to make that happen effectively?
I think it is.
That's part of the critique I'm putting forward here is that it's a critique of work methods
that I literally do not think you get more impact, right?
In fact, I think it's net negative.
I think once you cross over, generally speaking, that 40-ish hour threshold that I would go
so far as to say that the vast majority of people who end up working 80 hours a week,
they are less effective than the people who work 40 hours a week.
Simply because of all these negative consequences that come from being exhausted, myopic, not
removed from the work, all these other things, right?
You see, for example, the studies on what happens to empathy in people who don't get
enough sleep and enough being qualified as 80-hour plus.
They're just horrendous.
There's a great book called Why We Sleep that goes over a bunch of these studies.
One of the studies it goes over, I think it was in that book, it might have been from
Rice Science.
The book turned out to be controversial for some reason.
I don't know why I didn't read it.
I sleep eight hours.
I don't know.
But that book had some controversy.
But these things often go hand in hand, right, that people go like, well, it's unrealistic
to sleep 80 hours a week if you're someone out there crushing it, because like, hey,
you could be used for hustling.
If you just slept six hours a week or a night, you had another two that you could use for
some of this, right, and it just doesn't work.
So my critique is twofolded.
There's a procedural critique simply saying, this is not effective.
If you want to be more effective, and who doesn't want to be more effective?
We have some things to say about how many hours you should work and how those hours
should be spent, and how they should be grouped, and how you're slicing them up, and so on
and so forth.
And then there's, I can see how it kind of gets confusing, and we let this kind of thrash
back and forth.
There's also been a life critique essentially saying, on the last day, are you going to
regret it?
And do you know what?
I mean, it's almost, it's a cliche at this point, that like, well, no one under dying
death wish they spent more time in the office, right?
Do you know why it's a cliche?
Because it's true.
And do you know why it's true?
Because it's been studied ad nauseam, the Harvard longitudinal study that went, I think
like 80 years or something like that, tracing people from like the early 20th century, all
the way through to now, goes through like what happens to people who kind of aren't
maintaining proper social relations, and what happens on like the health effects, the regrets,
like they're just monumental.
And part of my critique here on that level is, I don't want you to regret your life.
But you know what, I think you're, I'm not talking about you, I'm talking about universal
you.
I don't want entrepreneurs to end up on the last day thinking, you know what, this wasn't
worth it.
Because the other part that comes into this is most businesses fail.
Most businesses need more than, or most entrepreneurs need more than one shot, and several of them
will never make it, right?
Like that's just the facts.
The facts are most businesses fail, and most entrepreneurs sort of, they never make it.
So if you spend, let's say, from your 20s to your 40s chasing businesses on this path,
trying to get them off the ground, trying to do all of it, right?
And it didn't work, which is the most likely outcome.
So you get to your 40, you now spend your 20s and your 30s obsessed with this, right?
Like chasing whatever you were chasing.
And it didn't work.
Are you going to wake it up on the other side thinking, shit, I wish I spent my 20s and
my 30s somewhat differently.
I think the odds of that are very, very high.
And I think that's just tragic.
Because I think you can get, first of all, the procedural critique, I think you can get
to the same place without that regret, right?
So this is part of the package I'm trying to present here is that I think it's more
effective on a literal sense in terms of productivity output impact, that to work out, or let's just
say 40 hour work week to make it that concrete, even if it isn't.
And I think it's a much better bet.
Because I looked at first of all, basecamp wasn't the first thing we tried.
We tried other things prior to basecamp and it didn't work.
And you know what, I have no regrets about that time, because I didn't put in 80 hours
a week on it.
I didn't trade my 19 through 23 on all the things I tried that didn't work.
I had like a string of projects, businesses in the wake of or not in the wake, preceding
basecamp that didn't work.
And you know what, it was fine.
And if basecamp hadn't worked, do you know what, it would also have been fine.
We weren't putting it all on the line.
It wasn't this big monumental bet that if it hadn't succeed, we were going to be destitute.
Which I think is, this gets us back into the societal critique here, is that I think that
is a driving force.
In the US, entrepreneurship feels like an insanely high stake business for a lot of people,
because literally they're putting it on their credit card or home mortgage loans, or they
don't have any of that.
And if this thing doesn't work, they're really shit out of luck.
I don't think we should be doubling down on that.
In fact, I think we should retreat from that and say like, go slower, do it more measured.
And this is why we put our experience at basecamp that we've spent over a year, I think it was
almost 18 months from the launch of basecamp.
And you know what, at the time, basecamp was already a success from day one.
We thought we were going to have, I forget what it was, that we were going to do $4,000
a month after a year, we did that after like two weeks.
So even now on our own metrics, like basecamp was a roaring success, even numbers are ridiculous
today, right?
And we'd be written off as a failure.
But still, even with that success, we went like, oh, all good.
We'll just keep doing our clients.
We'll keep doing our other stuff until we get to the point where like, there's nothing
on the line.
That's the other part of the whole entrepreneurial narrative that I just can't stand.
Is this sense of like high stakes gambling.
I hate fucking gambling, casinos are horrible.
I want nothing to do with it.
I want nothing to do with anything where the odds aren't essentially in my favor.
And I will just wait until the odds are in my favor.
That's what we did with basecamp.
We didn't go full time with basecamp until the odds were stupidly in our favor.
Of course, it could have failed.
But it wasn't like, ah, almost there.
Okay, so we had a very similar journey, right?
Because if we did consulting, we didn't fire anybody when we stopped doing consulting.
So until Beanstalk made enough money to cover everybody's salary that was on the team, we
did not stop doing consulting.
So I hear you.
All of those things are correct.
But that also came from a place of like real genuine privilege, right?
Like you're right.
Maybe there is a like a bigger societal conversation around the value we place on entrepreneurs
into our economy and how we should be supporting them better and how these shouldn't be these
insane high stakes games.
I agree with you and all of that.
But that is like, you guys had a place, we had a place of immense like luck and privilege
to be able to say we have a successful consulting business, making millions of dollars in consulting.
So like, let's create a product.
Let's see if it works.
It worked.
It grew really fast.
And I was like, oh, let's go.
Party time.
You know, like, but for people who don't have that, when I talk, one of the things that
we're working on, I think about a lot is how entrepreneurship in the US, it's really and
I imagine it's similar in other places, is really a young person's game.
Like it's it's a really difficult track in the US.
If you look for those who can't see David shaking his head no at me, the average age
of a startup founder, I think is 42 funded or not funded?
I forget what the statistics were just that there was this whole push on essentially a
data analysis on like, what is the average age of startup fund founders?
And it was much older than people thought that it's a Silicon Valley narrative that
you need like Stanford dropouts to essentially do that.
What was my point?
My point is just to say that like there's the risk profile.
I haven't seen that.
I don't know.
Funded or unfunded.
But if you want to start a product, if you want to start a business and you don't have
parents money, you don't have a side gig, you don't have all these things, it's going
to like that is hard.
You have a mortgage.
You have children.
You need health insurance.
We don't need to talk about that here, but I know we both have strong opinions on that.
But this is reality right now, right?
This is this is the America that we live in.
And like we talk about like, how can we internally for our team?
I have tons of people on my team would love to start a business and it's really freaking
hard and the risk is high.
They have it's it's easier.
Chris and I were young like what I was a waitress on the side.
Like that's how we lived.
We lived off of my waitressing salary, you know, like and then every every dollar that
went into the business went back into the business and it was great and we went we used
to trade with the local restaurant.
We did their work and they would pay us and we would eat in a nice restaurant.
That's how we got to eat out.
I mean, it was great.
Right.
That's such a romantic, lovely story.
But like we were young today, I got two kids in private school.
I have a mortgage.
I have all this stuff.
My parents that you know, like currently all these things, I don't know that I, you know,
where am I going to start a business?
It's almost like you need something like an earnest capital or like a whatever because
there's it's it's hard as shit and I think acknowledging that like some of these people,
like the folks that listen to indie hackers have full time jobs.
There's their 40 hours and then they're trying to do this thing on the side and they're trying
to make the right decision and do it at the right amount of time.
And I think philosophically I believe in everything you're saying, I think in a practical sense.
I just don't know that what happened to you guys is that repeatable like we were and to
us as well.
Like I say this all the time and people are like, how'd you get your first customer?
I was like, it doesn't matter, you're never going to be able to replicate that like ever.
Like it was 20 years ago, 16 years ago, it's never going to happen.
But you know, those things, it was luck, right?
Like it was different.
And I think that we should be a little kinder to people who are trying to to do it for the
first time.
And maybe maybe the store, the the way that you guys did it should be an aspiration as
it was for us when we were younger, trying to try to do this as well.
But it can't be the only way.
One of the things that David has said that I want to hear your opinion on Natalie is
that the grind doesn't work, that any hour you're working over, sort of like a reasonable
40 hour work week is actually counterproductive.
And that that is really better spent doing other things, you'll make better decisions
in your business that you're actually just hurting yourself.
And you worked clearly more than that.
So I'm curious, do you agree that the grind doesn't work?
Do you think that you're getting any sort of advantage at all by working harder?
And the reason I asked this question is that I think a lot of founders who are actually
in the thick of it, when they sit down at the end of the day, and they're thinking,
you know, I want to work humane hours, I want to work reasonable hours, but I feel like
I haven't reached this goal.
And I'm pretty confident that if we just work a couple extra hours tonight, I can get through
this email queue, I can release this feature, I can get a little bit ahead.
So Natalie, do you do you agree that like you don't actually incrementally improve your
chances by working a few extra hours?
Can I start by I think something that we're stuck on this hours thing, right?
And I think I'm struggling a little bit, because if I look back, like, they're all hours aren't
created equal, right?
We're not doing all the same things in those hours.
So I think maybe some of it is like, David, and I actually agree on a lot of this, but
we're just defining hours in a different way.
So for me, to answer your question is no, like I've always said launching a feature
weekly, I will, nobody has ever made more money because they launched a feature first
or they launched a feature week before they were, you know, a week earlier, right?
Like, we don't set deadlines like that.
We don't push our team to like kill themselves to launch a thing, because we said, we're
going to launch it on Tuesday and it's Tuesday and we're not ready yet.
Like, never, ever, ever have I seen that to be true.
Maybe in some crazy startup funded world, you have VCs breathing down your neck and
that becomes a rule.
It's not reality.
But I think as a founder, like these things in our experience came in waves, right?
Like they came in, in different experiences, a consistent 60 hour week is madness, right?
You're going to, you're just going to get tired.
And to me, I always refer to it as like a fog.
Your brain gets into a fog, right?
You're not, and then I'm not making good decisions.
And so there's, I do everything in my power to stay out of the fog because that is my
job is to have clear vision forward.
And if I don't have clear vision, I'm not doing my job.
And that's what, you know, that's what I tell it, like that's what you pay me to do.
But I think the early days, like those hours were different.
Like I absolutely agree that if we were, you know, if, if our team or whoever was like
writing 12 hours of code a day, that's insane, right?
You're not, you're going to make mistakes.
You're going to do really stupid things.
But there were times when I spent, you know, we spent like planning all day with the team,
you know, or things like that.
And then like, I would throw in an extra couple hours of support at night.
And to me, they're different.
It's a different way of thinking.
It's using a totally different part of my brain.
It's empowering.
It's also for me personally, it's also this thing like having support, knowing that folks
that are like buying into this crazy idea that we had early on stuck, like, and I look
at, you know, a lot, again, a lot of what we build, people rely on to do their work.
So if they're stuck, it's like a big thing.
So I don't want to go to sleep at night knowing that I'm holding somebody back.
Somebody who was also trying to build a business and somebody who also has a team and doing
these things.
So like, there's also like this personal thing and that mental weight is worth more or is
heavier than like doing that extra hour or two of support before I go to bed or before
I, you know, I do anything.
And that stayed consistent.
I mean, I really like, we really don't work a lot, but the hours are different.
There's times when at night I'm just thinking about stuff or, you know, to me, working is
reading a business book.
People might not disagree on that, but to me, if my mind is in that mode, like not working
to me, spending time with my children, when I'm on vacation, when I'm watching a movie,
when I'm reading some trashy fiction book, like I did two weeks ago, it was brilliant.
It was like the most amazing experience ever.
That's what I'm not working, but like reading a business book at night to me is working.
And so sometimes I get exhausted and I'm like, I got to put it away, but I'm not in front
of the computer.
I'm not answering email.
I'm not so, so they are, I think those hours are different and maybe it is that reflection
on what am I spending my hours on?
I've come to a point where I clearly understand the value of working on the business, not
in the business, as cliche as that also sounds.
And knowing that I have to set really clear time when I can focus and when I'm most productive.
And for me, that's mornings and so Tuesdays and Wednesday mornings, you can't book a meeting
with me.
You can't do anything.
My executive position keeps up.
And that's my thinking time.
I might not even open my computer, right?
I might take a walk.
I might read a book.
I might watch some videos of like other entrepreneurs, you know, whatever, like that's my thinking
time.
But I earned up to that, right?
Like I got to a point where I could do that, but those hours are radically different than
the hours I spend in one-on-ones with my team, you know, or on Thursday mornings when I have
my leads team.
So I just think they're different.
I don't, maybe that's the better conversation is less like work 40 hours and it's figuring
out where you're spending your energy and what's taking that energy away and what's
fueling your energy and where, you know, for today's call, I knew we were going to have
this call today.
And I said, you know, I'm not going to do anything else today.
I'm going to have the space to think about this, enjoy this time together so I'm not
focused or worried about the next meeting or where I'm heading out next, you know, and
I brought a book and I'll just probably read after we're done.
And that's kind of the way I try to schedule my time.
But so I don't know if it's 40 hours or 60 hours.
It's trying to make sure that I'm operating mentally at the capacity that creates clarity,
right?
That I have clear vision.
And in the early days, I can say that there would be, you know, one, I was young, I had
no idea what the hell we were doing, you know?
So there was like, there wasn't this conscious thought, like, oh, I have to be really smart
and think about the business.
But it was like, okay, we did support here.
I'm going to talk to the team here and research something here.
And, you know, just kind of kept pushing through.
So I have a co-founder, like Chris and I, we're not, we're not one, right?
We're two people.
So there is this kind of like trick where our 40 hours are really 80 hours, right?
Because there's two of us.
And so if you're...
Same with David in the early days.
Yeah.
I mean, there's the, you're, you kind of get lucky.
We definitely got the tag team on a lot of stuff.
You know, you, you focus on the product, I'll focus on the support and the customers and
all of that and come back together at some point and say like, all right, how's it doing?
Is it okay?
And then you kind of split up again, right?
That is a, that is a huge benefit.
Not that I recommend co-founders because I see that go wrong more than it goes right.
But you know, a spouse is fine, I guess, for me.
I would totally recommend co-founders.
I think absolutely trying to put everything on your own shoulders, not only is difficult
from an hour's perspective, like having 40 versus 80, I think it's also just immensely
difficult from a psychological perspective.
I agree.
It's just usually trying to hate each other.
Yeah.
So I think that is definitely a risk, which is another reason why I would, I mean, I sound
like a broken record, but like, I recommend looking at some of these stories like the
one I had with Jason, where we didn't start Basecamp like, Hey, oh, you're Jason.
I'm David.
Let's start Basecamp.
No, we worked together for years in advance, right?
So we got to know that like, Hey, this is someone I would actually want to start a business
with, right?
And dating our way into a marriage here, where, I mean, in your case, that was literally
a marriage.
Literally a marriage.
This was metaphorically speaking with Jason and I, but just the sense that like, Hey,
it's good to share the workload with someone.
And it's good to figure out first whether that's suitable or not.
One thing you mentioned earlier that I also just want to flag is I don't think the world
is different in the sense that it is harder today than it was then, I think it's the opposite.
I think I would love to start today versus 20 years ago in terms of the reach and capacity
to get off the ground.
I remember the stats from the early days.
So when we announced Basecamp, we had 3,500 RSS subscribers on Sickle vs. Noise, 3,500.
Like most cats have more followers on Twitter today than we did when we launched Basecamp.
Now that was clearly a kind of an efficient 3,500, let's call it that.
Like there were a lot of business owners and whatever and in that, and even that took five
years to build.
There were five years of history from 37 signals starting in 99 until Basecamp was launched
in 2004.
So part of this, I think it feeling difficult or harder today is a just lack of patience
sounds so scorning.
That's not what I mean.
I mean that like there are no overnight successes.
And that was true 20 years ago and it's true now.
Like you couldn't 20 years ago just be a total nobody that no one knows, no audience, no
following, launch a SaaS system and boom, there it goes.
No.
And I know this because plenty of SaaS companies launched in 2004 and 2005 and they're not
around anymore.
We are the exception, Natalie, simply by the fact that we stuck around, right?
So right there, that's going to be true always.
Like the survival rate of a business that lasts 20 years, what do you think the odds
of that are?
Like in software, less than 5%, 2%, 3%.
So if we are to impart any quote unquote wisdom, we have to accept the fact that we are exceptional.
If we were for 20 years ago or we're from yesterday, the number of businesses that get
to live or software businesses particularly that gets to live for 20 years, it's almost
nothing, right?
So part of that is that like there's only so much you can kind of take from that because
everything will be an exceptional tale.
But if you're going to chase the exceptional, why not do it on the best terms?
And again, this is why you say like, let's be kind to founders.
I 100% agree.
My hardship of a lot of situations is just unfathomable to me.
And I want to be so kind that they don't end up wasting 20 years of their life and regretting
it.
Like I'd rather be like harsh in the moment and then kind over time in the sense that
this sense of regret on the last day, it's a terrible thing.
I mean, writers have literally been writing about this topic for, I mean, millennia, right?
Like one of the main things I took out of the stoic principles of meditations or the
shortness of life or any of these other tomes from stoic philosophy was this focus on even
2500 years ago, someone would wake up on the last day and think, fuck, I misspent it.
I misspent it.
Like here I am, 75, I look back and like life was too short.
And why was it too short?
Because I spent it poorly.
So that's a cheery note.
I think this is an interesting point about enjoying working on your business, enjoying
the time you're putting into it.
To Natalie's point, there's different types of hours.
There's this sort of deep work, this creative work that quite frankly, you can't do more
than four or five hours of per day.
But as a founder, you've got other things you can do.
I know DHH, you've got a variety of things that you've done for Basecamp.
With Indie Hackers, like I work on the podcast, I'll travel to other cities and go to meetups
and meet all sorts of founders.
I write a lot of code, I do a lot of emails and writing, and quite frankly, I enjoy having
such a variety of things to do.
I spend a lot of time reading, just as Natalie does, and a lot of this stuff is stuff that
I would do for free.
Do you think that you're necessarily going to regret spending lots of time working if
you can align your work, I guess this concept of work-life integration, with things that
you actually enjoy doing in your day-to-day life rather than only having your job be a
bunch of drudge work?
I think a good way of looking at this, I enjoy my job thing, is I love working at Basecamp,
I really do.
Like, I think about this all the time, I think about, do you know what, I could literally
do anything, anything.
I have enough money that I could quit, I could do anything, and this is what I'd like to
do.
Like, first of all, that's just such a liberation.
But what I also like, I like truffles.
I like chocolate and strawberries, and I like to savour it.
Like, I could buy all the strawberries in the world, and I could dip them all in chocolate,
and I could just gorge on them all day long, I could just gorge on them, you know what,
that would not be good.
There are things you like in life that you savour, and you have just a bit of it.
And I love programming, I come back to this, I mean, I'm astounding myself, I've done a
lot of things over 40 years, very few things have stuck.
I used to be madly into video games, now I just kind of enjoy them.
I used to be all about race car driving for a while, well, not all about, but I really
like it.
And now that's sort of coming to an end, I've done it for 10 years, it doesn't have the
appeal.
Programming still has the appeal.
Doing for 20 years, love doing it, but I want to savour it.
And I feel like the chance of me wanting to puke from it, as in the strawberry case, is
if I try to gorge on it for like 80 hours a week, I'm going to puke.
I'm going to end up burning out on it, and I'm not going to enjoy it for the next 20
years.
And this is part of what I just I love this setup where I get to work on programming for,
let's say four hours a day, I mean, I don't get to work on programming most days for four
hours a day.
Those are the wonderful days.
Those are the days that deserve like a gold star and they get framed and they go whatever.
I want to keep doing that for the next 20 years or 40 years.
I'm not in a sprint, I'm not in a chase.
I'm trying to design life on like the first day, the middle day and the last day to be
pretty much the same.
This is why I brought up the case about my schedule does not look materially different
today than it did 20 years ago.
I mean, now there's three kids, so some of the non-work activities look substantially
different, but the work part doesn't look that different.
And it was just as sustainable and just as enjoyable in many ways on day one, as it is
now on day, whatever day it is after 20 years, and it's immensely possible.
I all believe that this is some exotic thing that we found that we are uniquely qualified
or was just an artifact of time or some of these other things.
I don't believe that.
I think truly, objectively, this is accessible to far, far more people than believe it.
And this is why I'm so passionate about it because it feels like in the sea, in the narrative
of entrepreneurship, we found a secret.
And I'm trying to tell everyone what the secret is, that there isn't that much secret to it.
The recipe is not complicated.
That doesn't mean it's hard, like all businesses are hard and the vast minority of them will
make it to 20 years, but it's not complicated.
It's hard, but it's not complicated.
And I think to me, there's just some liberation in that.
I think there's a lot of comfort, unfortunately, in this sense of, well, business is so hard,
no one knows anything.
It's all just these stereotypes we throw out to make founders feel good about themselves.
I don't think they always help.
I think one of the books, one of my favorites, it's funny, one of the books I've read recently
that I hate the most and yet also like the most is this book called Radical Candor.
I absolutely, I'm sorry if the author's listening to this, I mean no harm, but I just intensely
dislike the book, like how it's written and the anecdotes and the ethos of whatever.
But I also love, love, love the triangle, the radical candor versus ruinous empathy.
And I think there's a lot of ruinous empathy going on in entrepreneurial podcasting and
write ups and articles where we try to be kind by not telling people or sort of indulging
them in ways that like, it ends up not being kind.
And you are actually much kinder to people if you give them the radical candor.
You care, that's step one of radical candor, you can't just be an asshole, like this idea
of brutal truths is like, you're just an asshole, right?
Radical candors, you legitimately care, but you still tell people the hard things.
That's kind of what we're trying to do.
And I can only do it objectively, obviously, but not objectively at all.
I can only do it subjectively from our experience, but it's not like stylized.
That's one of the critiques I often get is like, well, now, well, maybe it is stylized
and I'm just unconsciously unaware of it, that's entirely possible too.
But we don't try to make it stylized.
We don't try to make it like, well, this is this sort of just exotic approach to it.
No, it's not exotic at all.
It's literally our message, is this banal, right?
It is absolutely banal, simple, not complicated, yet hard approach to business that millions
of businesses have gone through.
That Harvard study you talked about, to answer Cortland to your question, was that at the
end of the day, the thing that mattered was human relationships or relationships with
other people, right?
And so I think, for me, the answer to your question of whether, if you love this stuff,
will you actually on your last day regret it, is only true if that was the only thing
you cared about, right?
So I think in my experience, for us and for the team, everything is around these human
relationships that we look at Wildbit as a way to enable life outside of work, right?
So Wildbit exists to enable a life outside of work, right?
Everything we do is around creating this stability and safety and security and fulfillment so
that people are better humans all around, right?
And it's the same in my own, in our own lives, and it's the balance of spending that quality
time with my children, and I'm raising two daughters, and we talk about work at the dinner
table because we can and because I think it's empowering to them to hear about what their
mom does and the ability to accomplish what I have as a woman, but also seeing our relationship
together as a family, but also being really excited about the work that I do and the volunteering
work and all these things, they're all, that's back to the same thing to your point, is these
are different hours, right?
And maybe that's where, you know, it's easier to measure, to some degree, a software developer's
hours than it is, in my view, maybe my hours or another, because a lot of it is work.
I don't know.
It's all interchangeable, and it's all exciting.
Like I don't know, David, if you agree, but like if I'm on Twitter, I feel like I'm working,
right?
Like to some degree, it's some type of my, I know the only social media I have is Twitter,
so it ends up being work.
And so like the people who follow me know me as Natalie from Wildbit, and so like anything
I say on there, I think about, and it's, there's some kind of mental load around it.
So even that's work to me.
And so, you know, they are differences, but as long as you focus, as long as you're not
prioritizing that over people, right?
Like that, to me, work-life harmony, and this is what we talk about, is when you work with
people who are self-driven and motivated, right?
And you've given them an environment where they feel connected and there's purpose and,
you know, I'm not, I'm not absolving myself from that responsibility.
It's my responsibility to give that environment.
Their careers matter to them.
Their life matters more.
And so like, if life impacts work and work impacts life, right, like my job and everything
around Wildbit is to look at it and say like, these things have to fit together.
They can't be these like two segmented pieces because it's, you're asking for too much.
Like it's just not going to work.
There's going to be this really like abrasive experience between the two where I'd rather
be like, I want work to just support life and to create a space for it.
But also if you're working with people like you and like others who really care passionately
about this stuff, right?
I'm privileged to work with folks who genuinely care about this stuff.
You know, part of that is because Wildbit is a place where you're supported to care
about that, right?
And you're respected and cared for.
And I know there's a lot of places out there that don't do that and people don't do their
work because they don't, not because they're lazy, but because they're not being treated
well.
And so that's not the case here.
But when you do work with people like that, you know, it is okay to be excited about work.
Like we have this flexible work hours, right?
People always ask us about that.
So we have 32 hours of flexible working hours.
I don't care when you work.
We don't keep Slack open.
You know, I don't want you.
You guys to check in.
I'm not counting how many hours you spend in your seat, right?
Like I could care less.
And the idea was, came out just simply because life happens between nine to five, right?
Like we have two guys who became private pilots and I learned this, I didn't know this, but
to become a private pilot, you need to have a lot of hours and you can only fly in very
good weather.
And so it's, you can't fly after five when it's dark out.
Like it's just not, not feasible, you know, and so, or, oh shit, it's not windy today.
Let's go.
Like I gotta go now.
Right.
It's enabled both of them to get their license.
Not because I'm special, but because I looked at it as I don't give a shit when you work,
make sure you get really good quality work that I'm going to give you all the space in
the world to do it.
But let those two things melt together, right?
Because there's times when, especially in remote work, I mean, the gift of remote work
is that you're really allowing those things to melt together.
And if you can do that, you can be highly motivated.
You can work really hard and whatever that looks like for you, and also have this incredible
experience in life where you're making connections, you're connecting with your family, with yourself
as a human being, right?
Like self-connection is extremely important too.
You're getting all these things to work together.
That's harmony, right?
That's the ability to put those together.
I actually really dislike, I know we talk about this a lot, this like balance or this
thing where like balance to meet, right?
It's like a seesaw, one's up, one's down.
And that hard line, I think really, it really ruins the support that you can give to a human
being to say like, work is part of your life.
You know, you gotta, you gotta work, make a living.
And also hopefully you like the work that you're doing.
But it's in your brain, right?
Maybe David's right, and we're not different.
Entrepreneurs and the individual contributors that work for me and the rest of the team,
they think about this stuff too.
They think about the product.
We do these three-day weekends for a reason, not because they're more productive.
Everybody always asks me, why don't you finish work at six, nine to six, because it's shorter
days are actually more productive.
To me, it's much more valuable to have those three consecutive days off because of rest.
And the thing that we learned is like people, without thinking about it, they're subconsciously
solving challenging problems and run to work on Monday and they're like, I got it, I figured
it out, right?
And it's like, you know, their mind is thinking about their careers, this job, this work that
that is really fulfilling and why it creates a space to do it while working, right?
So it's like, it all flows together.
And so I don't, I don't know, there's my team, like they read books on things and they, on
the weekends and they practice other things and they extend their skills, you know, I
don't want to just all talk about programmers, like I've got all kinds of people work for
us and they do it for work, but they do it for themselves.
But they have fulfilled lives where they spend time with their families and their friends
and their hobbies.
And that's the holy grail, right?
You can do both.
You can be motivated and excited and passionate, but also make deep, meaningful connections
with human beings.
And that's it, right?
That's all that matters.
That's when, to David's point on your last day, you're going to be like, this was a good
one.
All I ask is extend that to entrepreneurs on the first day.
Everything you just said is a hundred percent true.
I mean, we were joking at the top of the start here where we're going to be in 90% agreement.
There's literally a hundred percent overlap and agreement between what you just said.
All I'm asking is you backtrack it and allow entrepreneurs to approach life and work the
same way on day one.
And I'm saying that like with the full authenticity of like, that's literally what we did.
Literally what we did.
What you just described, that's how I've been working for 20 years.
I mean, does anyone look at the amount of output that we at Basecamp were able to produce
in that time and say like, oh man, you guys were such slackers?
No, they don't.
Because you know what?
Hard work is not about the hours.
That's such a, I mean, no one here said it, so I can say it, it's such a stupid way of
looking at it.
Hard work is about the intensity you bring to it, like what comes out of it.
Those four hours, making those hours damn count.
I work incredibly hard within that regime, right?
The regime of making those four hours count for all their worth.
Very hard worker at that.
Very much not a hard worker when it comes to like what happens beyond the 40th hour
or whatever.
And also, I mean, I'll soften things just the smidgest and slightest of ways to say,
when I talk about 40 hours, I'm talking about sort of averages.
Was there ever a week where I worked 50 hours or even 60 perhaps because we had some emergency
or things were down?
Of course there was.
But there were also plenty of weeks where I worked 20 hours, right?
You average it out over a year, you look at it, and then you see, am I working about 40
hours?
That's the call I'm making.
Is that A?
If I averaged it out over 20 years, I bet I worked a lot less than 40 hours too.
If you say that, then I will agree.
I'm not averaging it out over 20.
That's too lenient.
I'm averaging it out over, let's say, six months or a year.
Some reasonable amount of time that can account for the unexpected, can account for the disasters.
And I mean, as you say, in the early days, I was the only person who managed the servers.
I wrote the code.
And if the server went down, I got up, right?
Do you know one of my favorite stories?
So when Beanstalk was really young, we had every day at four o'clock, it would go down
because everybody started committing their code.
And like the server, and we used to use Campfire.
And we had an open Campfire chat for our customers.
And every day at four o'clock, Chris and I would get into Campfire.
And all these customers would file in and we'd just be like, hey, sorry, guys, give
it an hour.
It's going to be fine.
What are you doing?
Like, what are you guys working on?
It was such a messy little nostalgic for those days.
But yeah, just, yes, outages, downtimes.
I also think if you're really talking about the ebbs and flows of the business, then I
think we're probably not far off.
Because I do believe that in the early days, even for us, you know, there were weeks when
it was hard, you know, like there were weeks when, or there was just things going on, right?
Like all of a sudden, there's just a bunch of things, right?
There's lawyers, and there's this thing, and there's that customer wants this kind of agreement.
And you're like, I don't know, should we do that in the early days?
You don't know, you know, all those moments.
And then there's weeks or months where like we wouldn't, like we'd go to breakfast at
like 11am.
Because the team was working in Russia, we're like, all right, look, we'll start at noon,
you know, and check in and do those things.
So it's probably true that it's averaged.
If it averages out, it's probably somewhere 40 to 50 hours a week, if we're really talking
hours.
And it's definitely not 20 hours a week.
Right.
I agree with that.
I mean, you can do 20 hours a week when you're just building something, not when you're running
something.
That's a lot more difficult.
We could build the base cam, the initial version of the software on 10 hours a week.
We've all postmarked in three months.
Right.
And the other thing I'd say is, is it is fair that like, no, I don't classify say reading
under work.
So almost everything I read, and that includes most specifically philosophy or sociology,
hugely impacts how I work, how I think about the business, how I think about, well, life
and everything, right?
I don't qualify, let's say Dostoevsky's notes from Underground as working, even though it
totally was.
I've referenced that perspective many times since reading that book, it's left a deep
mark in that.
So I do think that that is, it's fair to have a discussion about like, what actually counts
as work.
What I count as work for me, for the 40 hours, is sort of doing the code, doing the 101s,
doing customer support, doing the books, doing whatever, the specific finances, accounting,
whatever else that we did.
I don't count either, and perhaps I should, my agitation for democratic socialism on Twitter
as work either, maybe it should count and maybe I'm actually working two jobs once that's
factored in.
That's entirely true.
But I just...
Going to Congress.
Does that count as work?
Exactly.
Well, it did actually.
I did take the time off from work to write and travel for.
But I just, I want to be careful that we don't give entrepreneurs sort of the license to
think that actually averaged out over a year, 60 hours is a good, reasonable, sustainable
workload.
I don't think it is.
I agree with you on that.
And I think we're arriving at a very similar place here where the actual work that we've
talked about, what are the things that constitute work, not notes from underground, not social
democratic agitation on Twitter.
If you take these things out, get to the 40 hours and it's enough and it's plenty.
And in some ways, it's a liberation to have these constraints.
That's what I found.
And in some ways, once we had kids, it became even better.
The limits were really harsh.
Now my day will start at 9.15, why?
Because I have to drop off my son at 9 and I can't start at 9.
We just can't have a meeting there.
And it'll end at 5.
That's just when the day is over because I have other responsibilities.
It's such a gift to embrace those constraints and say, work must happen within this.
Because most people, they squander most of their time, as we said, in terms of does it
go to the right things?
No, it doesn't.
And if there are no boundaries, it'll just expand until it consumes most of it.
It's kind of like, what is it, post-law or something, work will expand to fill the time
available.
That is absolutely true on the broad scale too in terms of the entrepreneur and letting
them sort of subsume it, which is also why I think I looked up the stats when we were
talking about the successful entrepreneurs.
The claim was that they're far more, the average age for successful entrepreneurs is 40.
And I think part of the reason for that actually is that the 40-year-old actually has some
constraints on their time.
When you're 19, yeah, you can totally spend 80 hours a week or 100 hours a week.
You can work in really stupid ways and it has zero consequences because you've got nothing
else in your life that you're accountable to.
I mean, this sort of caricature, obviously there are plenty of 19-year-olds who do have
all sorts of accountabilities and constraints on their life.
But there's also sort of the myth of the young entrepreneur is one that doesn't, one that
does not have to account for these things.
I don't think it helps them.
I think they end up working worse.
I think they're worse off.
I remember this actually in 2005, we hired the second programmer at Basecamp besides
me, James Buck.
And when James joined, he had two kids.
I saw the immense productivity of someone who had to stop work at a certain hour.
And I marveled in that and it left a deep scar on me because, do you know what?
I wasn't that disciplined.
Let's just call it that.
I had a lot of work-life integration, as you said.
I'd sometimes end up working late in the evening because I took hours off in the middle
of the day, perhaps to go to a racetrack or something else, and all totally fine.
But the end result was not nearly as productive as watching James deal with the constraints
of his life.
And I went like, do you know what?
That's good.
That's actually good.
I'm envious in some regards of your hard constraints because they take some sort of the trouble
of sticking to it for yourself.
This is one of the other things I found about working out.
I am almost physically incapable of working out unless I have an appointment with someone
that will charge me money if I do not show up.
It's just not a thing that can happen otherwise.
You need the hard constraints.
I need the hard constraints.
And they're actually gifts.
So if we can gift entrepreneurs something, it is to not feel ashamed about the constraints
they have, especially if they're older entrepreneurs and they have very harsh limits because life
is there.
You go like, lucky you.
One of the funny things that happened when we switched to 32-hour work weeks was that
constraint of immediately saying, oh shit, we have one last day.
What are we going to do?
And that is, that was such an impactful thing on our team because we dropped random.
We had no meetings, we thought.
And then we found all kinds of meetings to cancel when you lost a day of work.
And I think the most critical part, especially, and maybe this is, David, to your point, the
thing that we didn't see when we were younger, the ability to stop and ask why.
Why are we doing the thing that we're doing?
Why are we spending the time on this thing?
Even to this day, I have 30 people and we're still like, are we sure this is the right
feature?
What's our reasoning for thinking about this feature?
Why do we want to work on it?
Why is this the scope?
Why is this the people that are working on it?
And that constraint of losing a day, the big panic for everybody was like, we're not going
to get enough done.
And I was like, well, I had such a strong feeling that we were going to be better working
less.
And they were so worried.
And there was a lot of anxiety and some moving and shaking and things that had to change.
But if we were to say, given what I know now and starting out again, the thing is always
figure out longer term.
And then you can start answering asking why.
I mean, I think the thing that most founders don't realize is you get on this kind of rat
race to some degree, I call it like the beast, right?
You start this business, it turns into a beast.
And by nature, just by design, a business wants to be bigger and fatter, right?
That's its natural state.
It just runs and runs and it'll take everything out on its place.
And if you don't stop to measure why you're doing the things that you're doing, what is
the ultimate outcome?
I've been thinking a lot about founders in general.
And you have companies like ours who really care about their teams and all these things.
But sometimes forget to even think about themselves as founders in that process and are chasing
these mile markers to some degree that they don't realize either don't need to be attained
or they're just too far away.
The joke I always made is like, it's actually really hard to spend a million dollars.
Everybody thinks they have to be a billion dollar business.
And then when you actually sit down and do the math, you're like, oh, that's not even
that important.
Why can't I be?
And if you start moving backwards and you're like, okay, well, even if you wanted a million
dollars and you've got 30% profit margins and you get to three million, can you get
to three million?
Probably you could.
And then it's like, not so scary anymore.
And you're not chasing these massive things that are like, oh, I got to do this thing
and go to, you know, and so you just stop.
You just got to stop at some point and say, all right, why do I work?
Why do I do the things that I do?
Why did I start this business?
Why do I want to keep working here, right?
All these things.
And I do think those moments of when you answer that, why you create constraints for yourself
or you create a clear purpose for yourself, because it is kind of to some degree, this,
you know, open ended thing that we're doing, right?
You can be a billion dollar business.
You can be a mom and pop shop.
You can be, you know, everything in between a solo, you know, small giants is like a great
book that I love very much.
And, and I think that when Bo talks about like the seamstress, you know, the woman who
designs dresses and she could be as big as Dior and she's like, not interested.
You know, and that was it.
I mean, it's all these ranges in between, but to get to that point, you have to truly
understand why.
Right.
Like, why, what, what is this?
Why am I doing this thing?
And in the early days, I think that's tricky one, right?
And maybe that's a good, a good measure or a good answer to Cortland your question earlier,
like, how do you know what to work on?
Maybe you start with figuring out why and what, like, what are you trying to build here?
Why are you doing it?
You know, if you're doing it because you want to be financially independent, that number's
not that big.
You know, for most people, it's not going to be, I need a million dollars a year or some
crazy number, right?
If you're doing it to be in control, you don't need to be a 600 person company, right?
You could do that with three people, you know, there's like all these things that if you
maybe as an early founder stop to, to say, well, why, what's the point here?
Right?
Cause you get to say that that's the whole point of being like a founder is like you
get to define the whole thing, not just how much money you make, not who you work with,
but what it looks like.
We have no sales team, right?
Everybody, like I'm leaving money, leaving money on the table.
I'm air quoting here.
And that's okay.
Like I'll grow a different way, right?
But that's just the way I've chosen.
I don't like sales.
I don't like the way that feels.
I don't want anybody on my team sending their seventh email.
Hey, I haven't heard from you.
Are you dead?
Like there's nothing that would destroy me more if my name was anywhere near or something
like that.
But that's just my choice.
And I get to design it, but I've had those moments of true clarity, right?
Like I've, Chris and I have gone away and like sat down and wrote copious documents
of like, well, where do you want to be?
Well, what about three years?
Five years?
We have kids now, right?
How long do I want to keep working?
Right?
And all these things that you start writing it down and it definitely changes things,
but I don't know that we did it very much.
Well, I know that we didn't do it in the very early days.
It was like, Oh, I got to build a business.
I don't want to go to college.
That was it.
It was, there was no big grandiose plan.
And maybe that's why you kind of chase things in random directions because it's, it's hard
to know where you want to go.
And I don't know that at 19, we would have been able to really say where we wanted to
go.
That changes when you have families and when you get older and see things a little bit
differently.
But that question of why people don't answer, I just want to cut in here for a second and
say it's super important to be aware of what you want because you made a great point.
Ultimately, if you're not the one deciding on these goals and recognizing them, they
just sort of come in from the outside world.
They come in from your social group, your peer group, your environment.
I live in San Francisco.
I talked to a lot of founders here.
A lot of people are chasing this billion dollar unicorn status for no other reason than everybody
around them seems to put that on a pedestal.
And so I think it's extremely important to be mindful about that.
But David made a point earlier that we never really quite resolved, which is that you as
a founder also have an effect on your team.
They kind of get their social cues from what you're doing as well.
And if you're working a lot and you're obsessed with your company, maybe they'll take that
cue.
Natalie, how do you get around that at Wildbit?
I know that your company is a part of your identity to some degree, and then it seeps
into different parts of your life.
Can you protect your employees from that and protect their ability to have separation and
balance?
Yes.
In a really practical sense, this is going to sound funny, but Chris used to send an
email on Sundays to the team and he would say he'd have some crazy idea on something.
He's like, we should build this.
And he started sending his emails on Sundays.
And it would always be Sunday because we had a weekend and his mind's racing.
And then at one point we were like, you have to stop doing that.
You're totally wreaking chaos.
Who talked about that?
I think Darmesh maybe talked about that once too, where he would send a bunch of shit around
and everybody's like, you got to stop.
Or no, it was Heaton.
Heaton Shaw.
Yeah, Heaton said it.
And he was like, you were running it.
It was Heaton bombs.
Yeah, that's right.
That's right.
That's right.
And so I think from a very practical sense, they said founders cast a big shadow.
And it's just really, truly understanding what you're doing.
Some of that we just don't let go back and remote work helps.
But some of it, we just don't let that go back into the system.
We just make sure that the team is shielded.
There's one thing, though, that I've learned, outages aside, because those things happen.
But I found that now I really, I work less than the team.
So those things don't really, they definitely take a cue from me.
But in the early days, when we were really obsessed, we were a very small team.
And we were working with people who were really excited about what we were building.
So there was, we all, I think collectively, to be honest, had to remove some of those
habits.
There was like five of us.
It was a collective, this was a long time ago, right?
They were building a product in Rails.
And it was super exciting.
And it was like, oh my God, we're going to do this thing.
And we're going to build hosted, we're going to host people's code.
They're going to think that's crazy.
We're going to do it anyway.
All of these things, there was this immense energy.
And we untangled ourselves out of that partially by having lives, like everybody started getting
married and having kids and realized very quickly, that's not the reality that we want.
But also just slowing down and figuring out that there's purpose and meaning.
And now it's, we take a tremendous amount of vacations, right?
I'm always focusing on the team.
And I think my problem now is that I find my team working more than 32 hours sometimes.
And I have to go in there and be like, what are you guys doing?
Get out of there.
I don't know why you're in there.
But their feedback to me has been pretty loud and clear that like, you're not my mom.
And if I'm really excited about something, I would like to be able to work on the thing
that I want to work on.
So I found this is, this was really challenging for me, but I found that I've had to kind
of say, as long as it's not consistent, as long as it's not burning out, as long as it's
not causing any kind of issues on your family, I'm not going to be your mom, right?
I'm not your mom, but like while that can't be setting goals that require you to do more
work than we are saying should be done.
So if you're doing this work because our goals, our timeline, our projects are more effort
or more whatever than they're supposed to be, then you need to push back.
You need to speak up.
We need to know that.
And we will just adjust the scope, right?
So that's where I'm trying to find balance.
And sometimes those things are tricky, but we're really, that's the message consistently
over and over again is if the reason you're working more or you decided to work on a Friday
is because you're pushing this thing because you promised to deliver it and it's just not
coming together fast enough, then no, like we're going to stop that thing, right?
We're going to read read, read, readjust that thing.
We're going to rethink about that thing.
But if you're working on a Friday because you got crazy inspired and you're like, holy
shit, I figured it out.
And like, I'm going to go, like, I'm not going to be like, no, please wait until Monday morning
at 9am to touch that like, and they push that back on me pretty heavily, which was funny
because it's kind of how my brain works too, right?
There's moments where I'm like, Chris, watch the kids.
I got to go write this thing.
You know, and that's okay for me because I feel like that's my job is it's my business
and all these things.
And they've kind of pushed back on me and said, like, we promise we're okay.
We'll let you know if things are getting out of control.
But sometimes we want that opportunity to just be inspired and go do great work.
And please don't stop us.
That would be ridiculous.
Completely agree with all that.
I mean, true for myself as well, right?
That's why I like this averaging out concept that an individual week spiking is not a big
deal.
Just you take it up some other week or you take it out some other week.
I do that at all time.
I'll work on a Saturday because I know I'm going racing next week and I won't be in on
Friday or Thursday or whatever.
So I think that makes total sense.
And why it's so important to zoom out and look at long term trends and not be like an
hour Nazi for like on the per hour basis of it.
Just see is there an overall sustainable trend here?
And then to sort of enforce that with being what you want to happen.
Natalie, as you say now, being someone who doesn't work those crazy hours, there was
the same for Jason and I.
If we wanted people to take vacation, we had to be authentic about that and take vacation.
Because in earlier years, we had this very misaligned or poorly thought out idea of unlimited
vacation days.
This was in I think the early 2010s or something.
And what ended up happening was no one took any vacation.
Because they just purely took their cues then from what someone else was doing.
And for example, for me, I didn't take a lot of explicit vacation because I was always
taking these mini vacations.
I'm going to a race track so I'm going to be out for two days.
I'm going to be out for two days there and I'm going to be out for two days here.
And that adds up to weeks and weeks out of a year.
But it didn't add up to like, oh, well, I was offline for three weeks straight.
So people took the cue that like, well, I should not take two to three weeks vacation.
That's clearly not kosher.
And when we found that out, or at least internalize those lessons, we were like, well, yeah, that's
dumb.
So now we have very explicit vacation time and just say like, hey, you should be taking
this time.
Hey, here's some prepackaged vacations that we've designed for you, you can take and we're
going to pay for them.
We're going to do all these other things to essentially encourage you that we're not just
saying these things.
We're doing these things.
We mean these things.
And I think everything we've talked about, I mean, we're so much in alignment here.
The only the only point of contingent would be to to back this out to include day one
founders.
If you promise to average it out.
I promise to average it out.
I'll give you six to 12 months to average it out.
Not 20 years.
Then I think we're in complete agreement.
And also, again, I mean, accounting for where the time is spent.
I think it was really important point, Nelius.
And I mean, if you are including like, well, this is the time I spent reading, or this
is the time I spent tweeting in general.
Fair enough.
I mean, I was clearly also at 50 or 60 hours if you took like all the time I sort of all
the influences or activities I could take that could possibly kind of make me a better
executive or make me a better programmer, make me a better human that would make me
a better executive and a better better programming.
That's probably true.
So I mean, it's not like there's the 40 hours and then all the rest of my time is just laying
perfectly still doing nothing.
Right?
Like that's not a...
Not with three kids.
And it's not an ideal I try to sort of put up either.
David, most of the people listening to the show are super early stage founders.
They're just trying to get their businesses figured out.
A lot of them are struggling to do so and probably feel a lot of pressure that they
need to work harder, maybe unsustainable hours to get things done.
What would be sort of your closing message for somebody who's in that situation and has
that mindset?
No, that it's not a requirement.
Know that others have gone through this process exactly where you are now and they didn't
work 60 or 80 hours a week.
Know that the pressure you're feeling is the pressure of a specific society in a specific
moment of time.
The pressures you're feeling were not true of the US in the 70s and 80s.
It was not true.
Well, that's actually 70s and 60s.
Let's go to that in terms of executive time spent and whether it was seen as generally
a good thing, whether hard work was equated to just more hours or a global thing.
This is not how people work in other societies on a grand scale.
You can absolutely opt out of that.
It's going to feel hard and it's going to feel like you might have feelings of guilt.
This is society just imposing this on you.
This guilt is not built into your DNA.
It's not native.
It is the product of decades of societal priming.
You are a product of the societal forces that you grew up in and America has profoundly
unhealthy unsustainable thoughts on work, particularly right now.
I think it takes a concerted effort to push that culture back.
That's kind of what I enjoy doing.
Getting a message basically saying that like, hey, we got to realign this.
We totally can.
The current myopia we are in particularly with startup founders, particularly what they
hear out of San Francisco, BC funded companies and so on.
There's deprogramming that needs to happen.
If someone was in a cult, they learned things that were not true.
First of all, you got to tell them all the things that were not true, but they're not
true.
Then you have to sort of take them out of that support system.
There's a lot of belonging in that.
There's a lot of belonging to be a unicorn chasing founder because there's just a lot
of others like you and it feels like you're all in it and it feels like you have a place
to belong.
Do you know what?
You can find a different place to belong and I'm trying to have one place.
There's going to be a lot of different places and a lot of different camps, but tech startups
in particular have been dominated by the Silicon Valley, BC, work crazy hours, camp.
We have to blow that shit up.
Natalie, you have successfully made the transition from being a founder whose life was almost
completely consumed by her business to being someone who's found a degree of balance, who's
found a way to bring a team into this that also has a lot of separation and a lot of
healthy habits.
What's your advice for other founders who maybe started off working unsustainably but
are now trying to make the same kind of transition that you have?
I don't disagree with David's perspective on this insane culture and I would never ever
advocate an 80-hour anything because I just don't think your brain is processing fairly
or even usefully.
I think for me and for any founder starting up, in my view, the goal should always be
profitability as fast as possible.
The goal should always be mental clarity as fast as possible because success highly depends
on your ability to think further than the next two days or the next week.
You can't have that mental clarity in your business if you're not really creating space
to think.
I have empathy for those early days and I think over this conversation, I think we ultimately
come to an average where we agree.
I want to say that in hindsight, what I believe we could have done differently, Chris and
I, in our 20 years was spending more time with clear thought, spending more time actually
thinking about what we want to build and why we want to build it and what those real goals
should be and what business I want to be in instead of really thinking about the product
and how we're going to ship it and how we're going to do these things.
The faster you can understand that you've made it or that you've gotten to the minimal
that you need, the faster you can slow down or maybe you didn't have to be speeding up
all the way there but if you were, really identify where were you trying to go.
If that is, I just need enough money to support myself, well, once you get there or figure
out a way to get there creatively and that's a different conversation but once you can
do that, then you can stop and say, okay, we're safe now.
Let's figure out where do I want to go?
What's the best path forward?
You can't really do that if you're not clear of mind.
If you're not spending the time quietly thinking about what you want to do and why you want
to do it.
I guess I don't disagree with David on most of that.
I just think our experience was different in the early days probably because we really
just didn't stop to think about why.
Why did we want to do this?
What were the ultimate goals and how far we wanted to run and those conversations you
should have with yourself pretty frequently.
In 20 years, that was not one conversation.
That is a continuous conversation of what do I want to do?
We have this now, we're setting off on the next 10 years, we're celebrating 20 in October
and we've just launched the next 10-year strategic plan, so here's the next decade and that's
my promise.
I said, I got another decade in me and then I don't know what's going to happen.
We might open a hotel or something, but the next decade is, but you can't have those conversations
without stopping and creating quiet space for yourself.
Those moments where people know us and get really excited about all these things that
we do, they didn't come from chaos.
They came from calm times like thinking about stuff and the faster you can get yourself
to there, I think the more success will be an option, a viable option versus the statistic
of failing and whatever that failure statistic is, it's so scary.
Natalie, David, I appreciate both of you for coming on the podcast and indulging me for
such a long time to talk about this important topic.
You both have pretty cool stuff you're working on, David, in your case, a new email product
that's not out yet, but I'd love it if you could tell people where they can go to find
out more about that and also what other things you're working on.
Sure.
It's called Hey.
H-E-Y.
It's hey.com and we are in crunch mode right now.
It's pretty crazy.
It's eight hours a day, five days a week, so already right there we're working 20% harder
than Natalie's team, right?
Which is funny because that's actually leading up to we launch in April and May 1st we start
our summer hours, which is also a 32-hour workweek that we run in the summer.
It's an integrated email service with its own clients and a whole new spin on how to
deal with email, making you love email again, if you ever did.
It's for people who care about email and want to see email be a better experience because
email is actually wonderful.
I've been emailing for 25 years at least.
I don't know if there's any other protocol perhaps outside of HTTP that has mattered
as much to me as email does.
It has certainly created more meaningful connections to people than any social medium I've ever
used and I just can't wait to share our vision for how to make email lovable in a way that
doesn't rely on spying pixels or advertisement or anything.
It's just a paid product.
It's just an email service that allows you to escape Gmail and all these other things
and love email again.
That's what I've been focusing on for almost like, what has it been, like 18 months?
We're coming up on just the final two months here now of running and I've been using it
myself now for a good six months at least and it's great.
If you are interested, you can send a story about email, about how either you love it
or hate it to iwantathey.com and that's how you get on the list.
There's no way you can just type in your email address, you got to send us a story.
I think 30 or 40,000 people have already sent us a story about how they either love or hate
or usually both love and hate email and yeah, April, this one's coming up.
Who's processing those emails?
We're filing them all into essentially a monster spreadsheet.
I think we're using, forget what we were using, some system where if you send an email, it
goes into the system and yeah, I mean just reading through 40,000 stories is something
so we're kind of just cherry picking out of it and it's just going to be the list.
The funny thing is that the gift here, at least as I've heard it from some people who've
sent the message was it allowed them to reflect on what they actually like about email.
It was more of a gift to the person signing up than perhaps it is that I'm going to sit
down and read 40,000 stories because I'm not.
Natalie, the last time that you were on the show, you were in a pretty similar position
to David.
You had just released a brand new product called Conveyor.
Can you let listeners know where they can go to find out more about what you're working
on today?
Yeah, we're actually working on a fun kind of side project right now called People First
Jobs, peoplefirstjobs.com.
David's seen it and it's going to launch in hopefully around April 1st at the end of March
and it's a job board but instead of following jobs, you follow companies.
The idea was that we don't hire very often, we're a small company and people would come
and look for a job and then they email us and say, well, if not you, who else?
I want other companies like you.
We want to focus on behaviors and less on perks and benefits.
What makes a People First company?
The ability to create a fulfilled work environment, the ability to do deep work, the ability to
have this work-life harmony, all these things, flexibility and benefits absolutely as well.
I think a lot of job boards really don't pay attention to the behaviors and people ask
in interviews or find out too late that these companies don't actually create the fulfilled
environments that they want.
We've been spending a bunch of time talking to tons of companies, talking to job seekers
which has been really fun and asking questions like what's missing in a typical job posting
and that's been really fun.
Those answers are fantastic.
We've been kind of sculpting this thing, hopefully launches at the end of March.
The team's been working really hard but it feels really fun and just special.
We're talking with some great companies.
We had a bunch of companies who signed up who want to be People First, everything from
software companies to backpack companies and other companies that are just really excited.
We'll see, but it's meaningful work which, while it's on this, I said this is like 10-year
strategic plan and the big realization for us was that while it doesn't have to be a
software company, it can be a company of just really smart people doing work that they care
about.
For us, everything right now is aligned around defining what that means a little bit more
but to be able to have the products but also projects, some maybe that make money, some
that are meaningful, and then really understanding what the profits are for and then generating
them back into other work.
I want to create a double bottom line where we can measure profits from the products and
then put them at the top and then figure out how we spend them.
We have these four-day work weeks, what are we doing on the fifth day, 30 people times
one day.
For 52 days, that's a lot of time that could be spent doing really meaningful work for
our communities, for ourselves as human beings, for each other.
There's just a lot of fun stuff.
The plan is starting to come together and it's just been tremendous fun for Chris and
I to look again to understand why and to look into these next 10 years and say, I want to
be here and it's not money.
That's fine, but it's actually going to keep me here so that I'm really excited.
After doing something for 20 years, and I imagine, David, similar stuff, I know you
guys were never going to launch another product and I was like, oh, we're definitely still
going to stay multi-product.
Then when you guys were like, hey, I was like, okay, good.
Things change, right?
We all grow and change.
I think for Chris and I having this opportunity to say, let's create a people first jobs because
it's meaningful and maybe it doesn't work out, but maybe it's great and it's important
to us.
That's just one, but there's a couple projects coming out this year that the rest are kind
of secret, but that the team's had a lot of time to play.
We're still very focused on our products and they're growing really well, but we're having
some space for some more fun things and that's just been wildly exciting.
Super fun to hear both of you talk about the way you run your companies and what you're
building and I'm looking forward to using all of this stuff.
Thanks David.
Thanks Natalie for coming on the show.
Good.
Thanks so much.
Yeah, this was great.
Listeners, if you enjoyed this episode, let me know on Twitter.
I am at CSAllen.
Feel free to send me a tweet and let me know what ideas you have for topics of discussion.
Guests, I should invite on the show.
Anything you're struggling with as a founder that you want more clarity or insight on.
I would love to host a couple of experts to just sort of hash it out and talk through
it.
Thank you so much for listening and I will see you next time.