If you want to build a successful business, you have to be ready to work 24/7/365 to have a shot at success… or do you? Both Natalie Nagele and DHH bootstrapped their internet businesses to millions in revenue, yet they took different paths to get there, with DHH only putting in a small number of hours vs Natalie who ate, slept, and breathed her job as a founder in the early days. In this episode we discuss whether or not DHH's approach is truly repeatable for others trying to get their businesses off the ground, the limits to human productivity and happiness, and the role that society and hustle culture in shaping how we feel about our work as founders.
People-First Jobs – Natalie's new approach to finding jobs with healthy work environments
Wildbit – Natalie's bootstrapped software business
HEY – DHH's new approach to email
Basecamp – DHH's project management + internal communication tool
@natalienagele – follow Natalie on Twitter
@dhh – follow DHH on Twitter
What’s up everybody? This is Courtland from IndieHackers.com, and you are listening to the Indie Hackers 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 did they get to where they are today? How do they make decisions both at 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 certainly deserve one.
Natalie Nagele is a former guest on the Indie Hackers 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 10 years now and generates many millions of dollars in revenue from multiple products including Postmark, which I happen to think is the best transactional email service. I use it for Indie Hackers and 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 Heinemeier Hansson, 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, a popular programming framework. He’s a New York Times bestselling author. He’s a professional racecar driver who took first place in his class at the 24 hours of Le Mans.
He is also one of the primary reasons why Indie Hackers exists. I can say without a doubt there would be no Indie Hackers if David’s talks and his writings that inspired me 11 or 12 years ago had not happened. David, thank you for the inspiration and welcome to the show.
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. It’s so hard, in fact, that success requires going through the grind and putting in excessive hours. What’s wrong with this picture in your view?
Starting with my own personal experience, which was one, I could not recognize in that image. When we started Basecamp back in 2003, we went the other way around. Basecamp started as a side project. So rather than pouring in 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 the technical underpinnings of the system when we got started.
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? Forty hours a week seemed like such an enormous amount of time to someone who - I had gone to Copenhagen Business School, I’d had other clients, and then we did this thing on the side.
So transitioning into the 40 hours work week was already a bit of an abrupt or harsh transition and one where I thought there was 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 the sense of, can I work creatively for 40 hours a week? Absolutely not.
A great day for me, a wonderful day, a homerun day, is four to five hours of concerted, creative effort, deep work, deep thinking, programming, that kind of stuff. Then there’s still hours left over to do all the other stuff, to send emails, to talk to the team, to figure out what we should do next.
So when I hear these stories - and they’re not really even 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 other bullshit, derogatory terms for working sane, reasonable hours.
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 established conventional wisdom for good reason.
First, it was studied ad nauseum by all sorts of people in the business world, but not for benign reasons. They were studied for productivity reasons. The example that I always give is Henry Ford putting together his assembly line going, “Do you know what? Forty 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. If we work 40 hours a week, that pans out.”
So I’m just leaning on that. No inventions here, no great insight, just leaning on the fact that, first of all, this is 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. The number is zero of the number of people until I was about in my early to mid-20s and I started to hear about Silicon Valley, dot-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 believe it, I just went, this is bananas. And this sense of, this is bananas, was 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 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 commission 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. “If you want to be a successful startup founder, you’ve got to pick two out of five. Either you can sleep --
I remember those.
-- “or you can exercise, or you can have a life, or you’re going to crush it at business.” And I just went, “This is so stupid,” literally stupid, as in dumb, unintelligent. I can’t stand it. Alright. I’ll just stop there.
It’s funny. You said you max out at four to five hours of creative work. One of the things that we obsess about on our team is the ability to allow our team to maximize the time when we can get that deep work done. That’s my everything. My whole brain functions around this.
The signs show, there’s no more then. 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. It’s why we ended up with a 32-hour work week, 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 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?
For the most part, I don’t disagree with anything that you’ve said. 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 use was, I don't think we could have done it ten hours, that’s for sure.
But 40 was really, really, really tough in the early days because of the pure, simple math of, we have to write the code. Well I wasn’t writing the code, but we have to build the software, design the software, think about the market, and then support our customers. I think that support piece is where we always found ourselves shifting paths.
Anything that resembled a 9 to 5 was because we have small teams. Neither Chris nor I write code ourselves. But they were tiny teams. It was like, “You guys focus on this. Focus on supporting. It’s doing down. Make sure it doesn’t go down anymore.”
Then it was like, “Alright. Let’s go have dinner, then we’ll come back and all do support.” You love your first customers, so I guess, David, I would love to know, in the early days how did you guys pull that off?
We’ve been Basecamp customers since the very beginning. I asked Chris this morning and he said, “I think we were number 800,” something early, early, early. So to Courtland’s point, Wildbit would not have existed if it wasn’t for 37Signals.
But I think one of the things that we always found so inspirational in the early days was if you emailed support, you’d get a response from Jason. It didn’t matter. Sometimes it would be at night, sometimes on the weekend.
So I guess maybe you can help me figure it out, cause that was always one of the things that I felt like, I don't know how we would find all of the time to do all the things that were important and sill do it in less than a 40 hour work week.
I think that’s a great point, because Jason did support at Basecamp for the first three years. It took three years before we hired someone else. At the end, he was answering I think 150 or 160 emails a day on support.
Part of this was setting expectations. 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 the guy goes out of his way to say, “You know what? I’m going on vacation, but don’t worry. It doesn’t matter. You can call me 24/7. Here’s my personal cell phone number. I always pick up, whatever it is.”
I wasn’t on trial for murder. I was buying a piece of real estate. 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 24/7?” This guy offers up, on his own, “I’m available 24/7. There are no boundaries. My life is your life.”
Then I talk to the lawyer in Denmark, and there we had a little bit more pressing thing. I forget what it was. But this is Thursday afternoon and he’s like, “Alright. Just want to tell you, I’m out tomorrow and I’m out on the weekend, and we can pick this up on Monday.”
The contrast between those two things was amazing. And do you know what? I had more respect for the second guy. I had more respect for the Danish lawyer who simply said, “It's almost 4:30. I gotta pick up my kids and we’ll talk about it on Monday.”
Do you know what? That was totally fine. He set realistic expectations. I think that there’s so much of this sense of how much time we have to put in, how much we love our customers. We’re just not setting boundaries, and we could. That’s what Jason did in large part in the early days.
He would sometimes answer late at night because he’d been out all day. There was not a 15 minute response time in the early days. If you caught Jason while he was at the keyboard, yeah, you’d get an answer right away. It usually would be very short. If it was a feature request, the answer would be even shorter. It would just be the word no.
I remember those days, too.
It was a different approach, but it was an approach that was targeted toward, “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.
We found over and over again that whatever pushback we would get from someone, like, “Hey, I’ve been waiting,” 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, but because we believe that we have to do this and it’s simply false.
I’ll give you another quick story. Before we started doing product development, Jason would do consulting work. And at the time, in the dot-com boom, the normal approach was you get a request for a proposal, and Jason would send back the standard proposal. That would be 25 pages.
One time he went, “Why am I wasting my time writing 25 pages? No one reads this shit. Let me try 12.” So he cut it down to 12. Same business. No one canceled. No one didn’t go through the contract. “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 a single page longer.
Exactly, and that was the insight. Customers just care about, “How long is this 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. There’s so many of these shortcuts we can take if we allow ourselves to do it.
I think part of that goes with, you also have to love yourself. I don’t mean that in an egotistical way, but in an Eric Fromm kind of, you have to have confidence in yourself to say, “I’m also a human being. I’m also worth recovering. It’s worth spending time on the weekends on something else, and in fact I’m both a better support person, I’m a better product person, I’m a better software engineering, I’m a better writer if I take the time to step away from the work.” The recovery time is just as important as the activity time if you want to do well.
A hundred percent. The recovery’s everything. I guess the part that I’m challenged with is, I look at businesses as seasonal. You have these early days and then you get the privilege of having people that work for you. You get the privilege of having a larger team, and these things become easier the more support you have. Profitability helps.
But if I started today, and I say this all the time, I’d be scared to death to start today because the world is so different from what it was. Our oldest product is 14 years old, too, so I don't know that I could pull it off. It is noisier. It’s harder to get it out there, and without an existing audience I’d have to build something new and do all these things.
I think, to me, working less is a goal, in the way that profitability is a goal. I would say that if I was 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. I think a lot of Courtland’s listeners are 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.
At some point the side project does enough to just cover it, to get them to that point where they’re 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 the starting point. That’s the scariest-shit place to be, because you’re not profitable. You’re barely making do, and now it’s chasing that real, true calm and the ability to create this thing that it sustains you and doesn’t suck all the energy out of you.
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. So I like to spend time with people. I have a group that I meet with every month. It’s manufacturing and car dealers, all kinds of stuff that’s not software.
They have similar experiences. There’s that initial season of a business where it is a ton of work. You’re just chasing that profitability. You’re chasing this ability to be calm and be restful, but it takes a while.
I agree with everything you say. My whole company, everything we do is especially for the team to sustain this peace and this ability to create a space for deep work. But as an entrepreneur, that wasn’t my experience. Early on it was, you’d just take a deep breath and you’re like, “Let’s keep running and let’s get at the profitability. Let’s make sure it supports our family. Let’s make sure it supports our team, and let’s protect the team.”
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 didn’t want them working a minute over 40. So there was slack to pick up.
I don't know, maybe the answer is 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 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 24 hours, 7 days.
You know, I’ve built infrastructure products. It’s a little bit different. But there’s a space in there, right? We should be chasing that calm. I mean, I don’t want to work 40 hours. I don’t work 40 hours. I don’t even what 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 the privilege of having a team support you. That’s the privilege of massive profit to sustain me. That’s the privilege of having products. I have a lot of products, so they give me some security and a little risk tolerance.
But there is that moment, those early days, where I think it’s hard, and I don’t see working more than 40 hours as some kind of failure. I think promoting 80 hour work weeks, you and I are in a hundred percent agreement that that hustle porn stuff is not interesting.
It’s dumb and it’s a bunch of, sorry, mostly white men who, that’s how they support themselves to feel good. 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 where you’re pushing. You’re pushing hard to get at that place where it’s stable.
I think that totally encapsulates the healthy anxieties that a lot of entrepreneurs sit with, but I want to push back on it nonetheless, because first of all, it wasn’t our experience. It is possible that we have a complete unique experience, but I don't think so.
And the reason 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 general contractors, or whether they were something else.
There was just a core 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 I totally agree with you that there’s a difference between feeling personally glorious because you’re putting in all this and it’s about exhibitionism and about these other things. And then there’s the internal side of it, which is, I should say, the chase.
To some degrees I think they’re flip sides of the same, similar addiction, a similar addiction to the rush of the start of the work, of chasing as you say. I think that word is interesting because that word was never something that came up for us, for me, the chase.
That sense of, “I have to fight before I can get to calm” strikes me as just one path. There’s also a path where you can start, as we did. Basically it 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 well enough for us to switch over, and it wasn’t hanging on by our fingernails. The reason we waited a whole year, we could probably have switched over to Basecamp, I don't know, after three months. You think that you’re just at the limit. We could just barely make expenses.
We waited until there was enough, there was 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 fulltime on Basecamp, to I think the ten employees we had - I don't know, I’m trying to remember the timeline here - four years later, you could 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 where we were choosing habits and we were cultivating habits that felt authentic, because there’s this idea that we’re going to do our damn best work in those four hours a day.
I don’t want to sound that glib about it, but I also want to say that running a company of four people, two of them were Jason and I. There were two employees, then there was Jason and I. It’s 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. The early days, much easier for me in terms of -
I’d love Jason’s perspective on that.
Actually, I took it from him. It’s his glib response that it only gets harder.
But let me ask you this, then, cause I think this is where I struggle. I don't remember chaos in the early days. That’s not what I remember. I remember this motivation, this intense desire to do this thing.
Yeah, but that’s not fair because you and Jason have built this incredible business and also this incredible following based on your ability to create these moments. You're on Twitter, you're writing books, you’re doing all these things.
You are chasing something as well. 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. Our brains are wired differently. They’re not better. They’re not worse. They’re just different.
I do think that it is a chase, but it’s also this, you commit to something. It’s like if I was a violist and trying to be spectacular, I would practice like a crazy person, cause it’s built in my brain to 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. I’m thinking of it as 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, Chris and I go on vacation together, and we have the luxury of being husband and wife and also cofounders, and we’re sitting on vacation 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 that can’t be bad, because this is how we’re wired. These are people who think about other things, and we can have hobbies. Chris has lots of hobbies. I know you have hobbies, all these things.
But it is. It’s this desire to do this thing. Maybe that isn’t work, how you define it, but to me that’s work. That’s still this, “I need to go away on a beach somewhere for a couple days and legit read trashy novels to stop thinking about work,” but it’s work.
I think it’s okay to work longer hours in the beginning and strive for a balance or a harmony of those two things, but to acknowledge that entrepreneurship is 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 required and what we want to do. There are entrepreneurs who just want to work more hours.
You and I agree on that a hundred percent. The whole, “You can’t build that without working 80 hours” is bullshit. I know that, especially if you realize that in the early days what everybody realizes. Everybody has the same trajectory, is to do business. They start off and they’re getting shit done and then at some point realize, “I gotta 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.”
We have to get out of it anyway. I tell me team, “You pay me to think. You don’t pay me to sit there and do support,” cause I’m not useful that way. So a hundred percent. To do the business, to grow the business, to do something special, to have meaningful work, I have to get out of it. But in the early days, I can’t. Who’s going to do that work for me?
I would posit, again, the work you think needs to be done often does just not need to be done. The lawyer that ways, “I’m available 24/7. You can call me any time,” he clearly thinks of himself, “I’m doing important work here. When I take a call on Saturday, this is 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 think entrepreneurs are that special. I think they get molded from social pressures in all sorts of ways, and I think American pressures that mold people are particularly harmful. If you compare them to entrepreneurs from other areas of the world, do you know what? The Danes are no smarter. They’re no lazier, none of these things.
The natural percentage of entrepreneurial DNA I would think is probably the same in Denmark as it is in the US. Maybe there’s some sort of bloodline, whatever. But you end up with completely different experiences. I think this is why comparing cultures is such an important thing to do.
I think one of the blessings that I’ve had has 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. Just those experiences taught me that, I’ll tell you, the Spanish approach entrepreneurship very¸ very, very differently than the Americans. Yet Spanish businesses exist. Spanish society exists.
All these things exist, and it’s also, me looking at the three different cultures, I think it’s fair to have value judgements about that. I think Americans are doing it wrong. 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 that 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 a hundred percent in your intentions on this, is “You know what? The entrepreneur 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 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. That’s just for show. That’s essentially bullshit. And I need to internalize that if I’m going to get ahead here, I should model what my boss is doing.”
That whole psychology and power dynamic, of course, is also not something I’m observing or inventing. This is just established organizational psychology. There’s modeling going on, and the way you build culture is not by what you say, it’s what you do. And all these other factors to it I think lead up to the fact that it’s very difficult/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, in your early days, “We don’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 so, I’d take objection to that.
I think the habits you form in the early days are incredibly hard to shake, and they form these organizational grooves. They can be redirected, and you can retrain them, but it’s very hard. 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, whether it’s crazy or not, everything is 80 hour weeks or we don’t have boundaries and we don’t have these things, and then you end up in Magic Land afterwards where you can do all these things.
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.
That’s why I can’t commit to this license that basically says, “No, no. You’re 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 getting to the point where what’s actually important, we have so much focus on “How many hours do we work?” and so little focus on how well we spent 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? Cause there’s such a lack of focus on making the eight hours count.
I want to jump in here a second, David, because you’re talking about something important, which is that in the early days, instead of working as many hours as possible and working on everything, it’s better to identify what matters, cut out the cruft and spend your time on the important stuff.
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.
Quite frankly, 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 a hundred percent sure. There are lots of things I thought were going to pay off that didn’t. There were things that I wasn’t that confident about that 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 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, 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. One of the key points it takes out is, don’t just track your hours. Track what you spend your time on.
So let’s say you worked 60 hours. You break that down, and you see where does the time go? Let’s just take a hypothetical 60 hours here. Well, I spent 20 hours, I don't know, networking, going out to coffee meetings, or -
I don't think that’s what Courtland was doing.
I don’t think so.
Probably writing code.
I actually did break down my time by category.
Well then I’m fascinated to hear what your breakdowns are, and I’d be very willing to critique the breakdown and 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? And the research on that one is just universally clear. No, it does not work, is less productive, will end you up with more bugs and more rework, and all these other things.
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 are very few other things that we do at Basecamp that I enjoy more than programming something that engages me.
Yet even with that, with all that passion, with all that energy, with all that 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, “Hey that was four hours very well spent. Let’s spend the time on something else, like talking on a podcast or whatever.”
My basic 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, alright. 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 do as an entrepreneur. That’s a society 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 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 worth some reflection. 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. How is this possible? I think you should 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 European/Scandinavian tradition into American work culture.
So I’m not from America. I don't know if you knew that, but I was born in Russia, so 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 I very much admire the Russian work ethic. But they work hard as shit.
But no, I think to Courtland’s question, and I think it was a really important one is, I believe, and I don't know, David, if 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. 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’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 Courtland’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.
I think I live more in the middle where I say there is 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 with David, and Jason, and Basecamp and this idea that we should create balance and we should be working on the right things and we should have clarity of thought. 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. Thirty people, tons of money. If I screw one up, it’s going to be okay.
I was saying the other day, a bootstrap business is invincible to some degree. I don’t bet the farm. So it’s a beautiful thing, I can take risks all day long. I can launch products. They don’t work out, it’s okay. 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 work less than 32 hours a week,” they don’t have the support. And I’ve done that. I’ve had talks. I’ve gone on stage and had these conversations, and people come to me and say, “Natalie, that’s amazing but what do I do?” And 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, so when it comes to drugs for women, it doesn’t process. The way that they cured ailments in women, it just doesn’t process.
So 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. This is an immense project that she’s working on. This is going to be, if it succeeds, 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’s she’s wrong, or she’s doing it wrong?
I look at her and I think, “Holy crap, you’re changing lives,” not that email isn’t a wonderful thing. But I build software for email. Okay. I told my team, “Eh, we don’t go around saving lives here.” She is, and she’s working like a mad woman, and 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. She’s going to accomplish it, and 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, and that 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’ve said.
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 their 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. So say someone who’s a, I don't know, exploitive hedge fund manager, whatever boogie man 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 has very effective work habits and a they’re very good at what they do. What they do is just terrible.
These configurations are all possible. So if we divorce this sense of worth from someone, 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, “Amazing mission you have. Have you thought about how you work?”
The Effective Executive is one of those books. 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 a world-changing, hugely aspirational mission, that they are 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. 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.
You see, for example, the studies on what happens to empathy in people who don’t get enough sleep and enough being qualified as eighty-hour plus. They are 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 Wry Science.
That 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 controversies.
But these things often go hand in hand, that people go “Well it’s unrealistic to sleep 80 hours a week if you’re someone out there crushing it,” because hey, that time could be used for hustling. If you just slept six hours a night, you have another two that you could use for some of this. It just doesn’t work.
So my critique is twofold. There’s a procedural critique. This is 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.
I can see how it gets confusing and we let this thrash back and forth. There’s also then a life critique, essentially saying, on the last day are you going to regret it? It’s a cliché at this point that no one on their dying death bed wishes they spent more time at the office.
Do you know why it’s a cliché? Because it’s true. And do you know why it’s true? Because it’s been studied ad nauseum. The Harvard Longitudinal Study that went I think 80 years, tracing people from the early 20th Century all the way through to now, goes through what happens to people who aren’t maintaining social relations and what happens.
The health effects, the regrets, they’re just monumental. And part of my critique here on that level is I don’t want you to regret your life. And I think you - 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, “Do you know what? This wasn’t worth it.”
Because the other part that comes into this is, most businesses fail. Most entrepreneurs need more than one shot and several of them will never make it. That’s just the facts. The facts are, most businesses fail and most entrepreneurs 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, and it didn’t work, which is the most likely outcome, you get to your 40s and you’ve now spent your 20s and your 30s obsessed with this, chasing whatever you were chasing and it didn’t work.
Are you going to wake 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 first of all, the procedural critique, I think you can get to the same place without that regret.
This is part of the package I’m trying to present here. I think it’s more effective on a literal sense, in terms of productivity output impact, let’s just say 40-hour work week to make it that concrete even if it isn’t, I think it’s a much better bet.
First of all, Basecamp wasn’t the first thing we tried. We tried other things prior to Basecamp and they 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 a string of projects, businesses, preceding Basecamp that didn’t work, and it was fine. If Basecamp hadn’t worked, 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 succeeded, we were going to be destitute, which I think is - that gets us back into a societal critique here, I think that is a driving force.
In the US, entrepreneurship feels like an insanely high stakes business for a lot of people, because literally they’re putting it on their credit card or home mortgage loans or if 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, “Go slower. Do it more measured.”
Our experience at Basecamp, we spent over a year. I think it was almost 18 months from the launch of Basecamp. 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 $4,000.00 a month after a year. We did that after two weeks. So even on our own metrics, Basecamp was a roaring success.
The numbers are ridiculous today. We’d be written off as a failure. But still, even with that success, we went, “All good. We’ll just keep doing our clients. We’ll keep doing our other stuff, until we get to the point where 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 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.
I would just wait until the odds were in my favor. That’s what we did with Basecamp. We didn’t go fulltime with Basecamp until the odds were stupidly in our favor, where of course it could have failed, but it wasn’t like, “Aah! Almost there.”
We had a very similar journey cause 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 real, genuine privilege. You’re right. Maybe there is a bigger societal conversation around the value we place on entrepreneurs and to 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.
But we had a place of immense luck and privilege to be able to say, “We have a successful consulting business. We’re making millions of dollars in consulting. Let’s create a product. Let’s see if it works.” It worked. It grew fast and it was like, “Oh, let’s go. Party time.”
But for people who don’t have that one of the things that we’re working on, I think a lot about how entrepreneurship in the US, and I imagine it’s similar in other places, is really a young person’s game. It’s a difficult track in the US. For those who can’t - David’s 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 what is the average age of startup founders, and it was much older than people thought. It’s a Silicon Valley narrative that you need Stanford dropouts to do -
That wasn’t my point. My point was -
Just to say that the risk so far -
I haven’t seen that. I don't know. Funded or unfunded. But I’m saying, 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, 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 that is reality right now. This is the America that we live in. For our team, I have tons of people on my team who would love to start a business, and it’s really freaking hard and the risk is high. It’s easier, Chris and I were young. I was a waitress on the side. That’s how we lived.
We lived off of my waitressing salary, and every dollar that went into the business went back into the business and it was great. 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. It was great. It was such a romantic, lovely story, but we were young.
Today, I’ve got two kids in private school. I have a mortgage. I have all this stuff. I have parents, grandparents, all these things. Where am I going to start a business? It’s almost like you need something like an Earnest Capital or a whatever because it’s hard as shit and I think acknowledging that some of these people, like the folks that listen to Indie Hackers, have fulltime 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 the right amount of time.
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, and to us as well. I say this all the time when people are like, “How did you get your first customer?” I’m like, “It doesn’t matter. You’re never going to be able to replicate that, ever.” It was 20 years ago, it was 16 years ago. It’s never going to happen.
But those things, it was luck. It was different. I think that we should be a little kinder to people who are trying to do it for the first time and maybe the way that you guys did it should be an aspiration as it was for us when we were younger trying 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 a reasonable 40-hour work week is actually counterproductive, and that that is better spent doing other things, that you’ll make better decisions for your business, that you’re hurting yourself. You worked, clearly, more than that. So I'm curious, do you agree that the grind doesn’t work? Do you think that you were getting any advantage at all by working harder?
The reason I ask this question is that I think a lot of founders who in the thick of it, when they sit down at the end of the day and are thinking, “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 I just work a couple extra hours tonight, I can get through this email que. I can release this feature. I can get a little bit ahead.” So Natalie, do you agree that you don’t incrementally improve your chances by working a few extra hours?
We’re stuck on this hours thing. I think I’m struggling a little bit because if I look back, all hours aren’t created equal. We’re not doing all the same things in those hours.
So I think maybe some of it is that David and I agree on a lot of this but we’re defining hours in a different way. So for me, to answer your question, no. I’ve always said, launching a feature a week late, nobody has ever made more money because they launched a feature first or they launched a feature a week earlier.
We don’t set deadlines like that. We don’t push our team to kill themselves to launch a thing because we said we were going to launch it on Tuesday and it’s Tuesday and we’re not ready yet. Never, ever, ever have I seen that to be true. Maybe in some crazy startup funded world you have VC ‘s breathing down your neck and that becomes a rule. It’s not reality.
But I think as a founder, these things in our experience came in waves. They came in different experiences. I consistent 60 hour week is madness. You’re just going to get tired. To me, I always refer to it as a fog. Your brain gets into a fog, and then I’m not making good decisions.
So I do everything in my power to stay out of the fog, because my job is to have clear vision forward. If I don’t have clear vision, I’m not doing my job, and that’s what I tell me team. That’s what you pay me to do.
But I think the early days, those hours were different. I absolutely agree that if our team or whoever was writing 12 hours of code a day, that’s insane. You’re going to make mistakes. You’re going to do stupid things. But there were times when we spent planning all day with the team or things like that and I would throw in a couple hours of support at night.
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. For me, personally, it’s also this thing of having support, knowing that folks, that are buying into this crazy idea that we had early on, are stuck.
Again, a lot of what we build, people rely on to do their work. So if they’re stuck, it’s a big thing. So I don’t want to go to sleep at night knowing that I’m holding somebody back, somebody who is also trying to build a business, and somebody who also has a team and doing these things.
So there are these personal things, and that mental weight is heavier than doing that extra hour or two of support before I go to bed or before I do anything. And that stayed consistent. We really don’t work a lot but the hours are different.
There are times when at night I'm thinking about stuff, or to me, working is reading a business book. People might disagree on that, but to me, if my mind is in that mode, not working to me is 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 the most amazing experience ever. That’s when I’m not working.
But reading a business book at night, to me, is working, because sometimes I get exhausted and I have to put it away, but I’m not in front of the computer. I’m not answering email. So 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 cliché as that also sounds, and knowing that I have to set clear time when I can focus and when I’m most productive. To me, that’s morning. That means Tuesday and Wednesday mornings you can’t book a meeting with me. You can’t do anything.
That’s my thinking time. I might not even open my computer. I might take a walk. I might read a book. I might watch some videos of other entrepreneurs, whatever. That’s my thinking time, but I earned up to that. 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 or on Thursday mornings when I have my leads team.
So I just think they’re different. Maybe that’s a better conversation. It’s less “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.
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 this 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.
I brought a book and I’ll probably just read after we’re done. And that’s the way I try to schedule my time. 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, that I have clear vision.
In the early days I can say that there would be, one I was young. I had no idea what the hell we were doing. So 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 leader. I’m going to research something here,” and just kept pushing through. Also, I have a cofounder. Chris and I, we’re not one. We’re two people. So there is this trick where our 40 hours are really 80 hours cause there’s two of us.
Same with David, in the early days.
Yeah. You get lucky. We definitely got to tag team on a lot of stuff. 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, “All right. How’s this doing? Is it okay?” and then you split up again. That is a huge benefit. Not that I recommend cofounders, cause I see that go wrong more than it goes right, but a spouse is fine, I guess, for me.
I would totally recommend cofounders. I think absolutely, trying to put everything on your own shoulders not only is difficult from an hours perspective, having 40 versus 80. I think it’s also just immensely difficult from a psychological perspective.
I sound like a broken record, but 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. So we got to know that like, “Hey this is someone I would want to start a business with.” We’re not blind dating our way into a marriage here. In your case it was literally a marriage.
Literally a marriage.
This was more metaphorically speaking with Jason and I, but the sense of 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 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 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. When we announced Basecamp, he had 3,500 RSF subscribers on SICOM versus noise, 3,500. Most cats have more followers on Twitter today than we did when we launched Basecamp.
Now that was clearly an efficient 3,500, let’s call it that. There were a lot of business owners, and even that took five years to build. There were five years of history from 37Signals starting in ’99 until Basecamp was launched in 2004.
Part of this feeling difficult or harder today is a lack of - patience sounds so scorning. That’s not what I mean. I mean that there are no overnight successes. That was true 20 years ago and it’s true now. You couldn’t, 20 years ago, be a total nobody that no one knows, no audience, no following, launch a SaaS system and boom, there it goes. No.
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. So right there, that’s going to be true always, the survival rate of a business that lasts 20 years. What do you think the odds of that are? In software? Less than 5%.
I know that.
Two percent, three percent? So if we are to impart any quote/unquote wisdom, we have to accept the fact that we are exceptional, whether we were from 20 years ago or we were from yesterday, the number of businesses that get to live, software businesses particularly, that get to live for 20 years, it’s almost nothing.
Part of that is there’s only so much you can 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? Again, this is why you say, “Let’s be kind to founders.” I a hundred percent agree.
The hardship of a lot of situations is 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. I’d rather be harsh in the moment and then kind over time, in the sense of this sense of regret on the last day. It’s a terrible thing.
Writers have literally been writing about this topic for millennia. One of the main things I took out of the stoic principles of meditation, to The Shortness of Life or any of these other tomes from stoic philosophy, was this focus on even 2,500 years ago, someone would wake up on the last day and think, “Fuck, I misspent it. I misspent it. Here I am, 75. I look back and 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 are different types of hours. There’s this 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 with Basecamp. With Indie Hackers, 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.
Quite frankly, I enjoy having such a variety of things to do. I spend a lot of time reading, just as Natalie does. 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 enjoy doing in your day-to-day life, rather than only having your job be a bunch of drudge work?
I think I good way of looking at this “I enjoy my job” thing is, I love working at Basecamp. I really do. I think about this all time. I think, “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.”
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 savor it. 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’d just gorge on them.
That would not be good. There are things you like in life that you savor and you have just a bit of it. I love programming. I come back to this. 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 enjoy them.
I used to be all about racecar driving for a while. Not all about, but I liked it, and now that’s coming to an end. I’ve done it for 10 years. It doesn’t have the appeal. Programming still has the appeal. I’ve been doing it for 20 years, love doing it. But I want to savor it.
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 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.
I love the setup where I get to work on programming for let’s say four hours a day. 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 a gold star and they get framed. 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 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. Now that 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’ve all believed [SIC] 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.
This is why I’m so passionate, because it feels like in the seed, in the narrative of entrepreneurship, we found a secret. I’m trying to tell everyone what the secret its, that there isn’t that much secret to it. The recipe is not complicated.
That doesn’t mean it’s (not) hard. 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. To me there’s some liberation in that. I think there’s a lot of comfort, unfortunately, in this sense of, “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. 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’m sorry if the author’s listening to this. I mean no harm. But I just intensely dislike the book, how it’s written and the anecdotes and the ethos.
But I also love, love, love the triangle, the radical candor versus ruinous empathy. I think there’s a lot of ruinous empathy going on in entrepreneurial podcasting and writeups and articles, where we try to be kind by not telling people, or indulging them in ways.
It ends up not being kind, and you’re 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, this idea of brutal truths. You’re just an asshole. Radical candor is you legitimately care, but you still tell people the hard things. That’s what we’re trying to do.
And I can only do it objectively, obviously - well, not objectively at all. I can only do it subjectively from our experience. But it’s not stylized. That’s one of the critiques I often get is - well maybe it is stylized and I’m 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 exotic approach to it. No, it’s not exotic at all. That’s literally our message. This is banal. It’s this absolutely banal, simple, not complicated, yet hard approach to business that millions of businesses have gone through.
That Harvard study you talked about, Courtland to your question, was at the end of the day the thing that mattered was human relationships, or relationships with other people. So I think for me, the answer to your question of whether if you love the stuff will you on your last day regret it, is only true if that was the only thing you cared about.
So I think for my experience, and for us and for the team, everything is around these relationships, that we look at Wildbit as a way to enable life outside of work. Wildbit exists to enable a life outside of work. Everything we do is around creating this stability and safety and security and fulfillment so that people are better humans all around.
It’s the same in our own lives and it’s a balance of spending that quality time with my children. I’m raising two daughters. 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 excited about the work that I do and the volunteering work.
Back to the same thing, to your point, these are different hours, and maybe that’s where it’s easier to measure, to some degree, a software developer’s hours than it is in my view maybe my hours. Because a lot of it is work. I don't know. It's all interchangeable and it’s all exciting.
I don't know, David, if you agree, but if I’m on Twitter, I feel like I’m working. The only social media I have is Twitter so it ended up being work. The people who follow me know me as Natalie from Wildbit. So anything I say on there I think about. There’s some kind of mental load around it, so even that’s work, to me.
So they are different, but as long as you’re not prioritizing that over people. To me work/life harmony is when you work with people who are self-driven and motivated and you’ve given them an environment where they feel connected and there’s purpose - I’m not absolving myself from that responsibility. It’s my responsibility to give them that environment.
Their careers matter to them. Their life matters more. So if life impacts work and work impacts life, my job, and everything around Wildbit is to look at it and say these things have to fit together. They can’t be these two segmented pieces because you’re asking for too much.
It’s not going to work. There’s going to be this abrasive experience between the two, where I want work to support life and to create a space for it, but also if you’re working with people like you and others who care passionately about this stuff.
I’m privileged to work with folks who genuinely care about this stuff. Part of that is because Wildbit’s a place where you’re supported to care about that, and you're respected and cared for. I know there are a lot of places that don’t do that, and people don’t do their work, not because they’re lazy but because they’re not being treated well. That’s not the case here.
But when you do work with people like that, it is okay to be excited about work. We have these flexible work hours. People always ask us about that. We have 32 hours but flexible hours. I don’t care when you work. We don’t keep Slack open. Nobody had to check in. I’m not counting how many hours you spend in your seat. I could care less.
The idea came out simply because life happened between 9 and 5. 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. You can’t fly after 5:00 when it’s dark out. It’s not feasible, or, “Oh, shit. It’s not windy today. Let’s go. I have to go now.”
Wildbit enabled both of them to get their license. Not because I’m special but because I looked at it and said, “I don’t give a shit when you work. Make sure you get good quality work done. I’m going to give you all the space in the world to do it.” But let those two things meld together. Cause there’s times, especially in remote work, I mean the gift of remote work is you're allowing those things to meld together.
If you can do that, you can be highly motivated. You can work hard in 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. Self-connection is extremely important, too. You’re getting all these things to work together. That’s harmony. That’s the ability to put those together.
Balance to me is like a seesaw. One’s up, one’s down. That hard line ruins the support that you can give to a human being to say work is part of your life. You have to work., You have to make a living and also hopefully you like the work you’re doing.
It’s in your brain. 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 6:00, 9:00 to 6:00, because shorter days are more productive.”
To me, it’s much more valuable to have those three consecutive days off because of rest. The thing that we learned is that people, without thinking about it, are subconsciously solving challenging problems and run to work on Monday like, “I got it. I figured it out.” Their mind is thinking about their careers, this job, this work that is fulfilling, and Wildbit creates a space to do it while working. So it all flows together.
So I don't know. My team reads books on things on the weekends and they practice other things and they extend their skills. I don’t want to just talk about programmers. All kinds of people work for us. 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.
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. 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. We were joking at 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. I’ll I’m asking is you backtrack it and allow entrepreneurs to approach life and work the same way on day one. I’m saying that with the full authenticity of that’s literally what we did. Literally what we did. What you just described, that’s how I’ve been working for 20 years.
Does anyone look at the amount of output that we at Basecamp were able to produce in that time and say, “Oh man, you guys were such slackers”? No, they don’t, because you know what? Hard work is not about the hours. 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, what comes out of it. Those four hours, making those hours damn count. I work incredibly hard within that regime, the regime of making those four hours count for all they’re worth. Very hard worker at that, very much not a hard worker when it comes to what happens beyond the fortieth hours.
I’ll soften things just a smidgest and slightest of ways to say, when I talk about 40 hours, I’m talking about averages. Was there ever a week where I worked 50 hours or even 60 perhaps because we some emergency or things were down? Of course there was. But there were also plenty of weeks where I worked 20 hours. 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, 40 hours -
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. As you say, in the early days I was the only person who managed the servers. I wrote the code. If the server went down, I got up.
Do you know, one of my favorite stories, when Beanstalk was young, every day at 4:00 it would go down, because everybody started committing their code. We used to use Campfire, and we had an open Campfire chat for our customers.
Every day at 4:00, Chris and I would get into Campfire and all these customers would pile in. We’d be like, “Hey, sorry guys. Give it an hour. It's going to be fine. What are you doing? What are you guys working on?” It was such an - I’m actually a little nostalgic for those days.
But yes, out at down times, 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, there were weeks when it was hard or there were things going one. All of a sudden there are a bunch of things.
There are 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. All those moments. And then there’s weeks or months where we’d go to breakfast at 11 a.m. cause the team was working in Russia.
We were like, “Alright. We’ll start at noon” and check in and do those things. So it’s probably true that if it averages out, probably somewhere like 40 to 50 hours a week if we’re really talking hours. Definitely not 20 hours a week.
Right. I agree with that. I mean, you can do 20 hours a week when you’re building something, not when you’re running something. That’s a lot more difficult. We could build Basecamp, the initial version of the software, on 10 hours a week.
We built Postmark in three months.
Right. It is fair. 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 life and everything.
I don’t qualify, let’s say Dostoyevsky’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 it’s fair to have a discussion of what counts as work. What I count as work, for me, for the 40 hours, is doing the code, doing the one-on-ones, 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 working two jobs once that’s factored in. That’s entirely true.
[UNINTELLIGIBLE] to Congress? Does that count as work?
Exactly. It did. That, I did take the time off from work to write and travel for. But I want to be careful that we don’t give entrepreneurs the license to think that, 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.
We’re arriving at a very similar place here.
The 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. It’s plenty, and in some ways it’s a liberation to have these constraints. That’s what I found.
In some ways, once we had kids, it became even better. The limits were harsh. Now, my day will start at 9:15. Why? Because I have to drop off my son at 9:00 and I can’t start at 9:00. We can’t have a meeting then. And it’ll end at 5:00. That’s 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 squander most of their time, as we’ve said, in terms of, does it go to the right things? No, it doesn’t. And if there are no boundaries, it will expand until it consumes most of it.
It’s like Post’s 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 in letting them subsume it, which is also why I think - I looked up the stats while we were talking about successful entrepreneurs.
The average age for a successful entrepreneur is 40. I think part of the reason for that is that the 40 year old has some constraints on his time. When you’re 19, yeah, you can 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.
That’s a caricature. Obviously, there are plenty of 19 year olds who do have all sorts of accountabilities and constraints on their lives. But there is the myth of the young entrepreneur as one that does not have to account for things. I don't think it helps them. I think they end up working worse. I think they’re worse off.
I remember this. 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. I marveled in that, and it left a deep scar in me.
I wasn’t that disciplined. Let’s 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, all totally fine.
But the end result was not nearly as productive as watching James deal with the constraints of his life. I went, “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 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. They’re gift. 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 the constraint of immediately saying, “Oh, shit. We have one less day. What are we going to do?” And that was such an impactful thing on our team because we had no meetings, we thought, and then we found all kinds of meetings to cancel when you lost a day of work.
I think the most critical part, 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, at 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 are these the people that are working on it?” And that constraint of losing a day, the big panic for everybody was, “We’re not going to get enough done.”
I had such a strong feeling that we were going to be better working less, and they were so worried. There was a lot of anxiety and some moving and shaking of things that had to change,. But if we were to say given what I know now, and starting out again, the things always figure out longer term and then you can start asking why.
I think the thing that most founders don’t realize is you get on this rat race to some degree. I call it The Beast. You start this business. It turns into a beast. By design a business wants to be bigger and fatter. 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. 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 too far away.
The joke I always made was it’s hard to spend a million dollars. Everybody thinks they have a billion dollar business, and then when you actually sit down and do the math, you’re like, that’s not even important.
If you start moving backwards and you’re like, okay well even if you won a million dollars and you have 30% profit margins, and you get to $3 million, can you get the $3 million? Probably you could.
And then it’s not so scary anymore and you’re not chasing these massive things that are like, oh, I’ve gotta do this thing.” Stop. You just have to stop at some point and say, “Alright. Why do I work? Why do I do the things that I do? Why did I start this business? Why do I keep working here?”
I do think those moments when you answer that, why you create constraints for yourself or you create a clearer purpose for yourself, because it is to some degree this open-ended thing that we’re doing. You can be a billion dollar business. You can be a mom and pop shop. You can be everything in between, a solo, a small giant.
There’s a book that I love very much, and I think when Beau talks about the seamstress, the woman who designs dresses. She could be as big as Dior and she’s like, “Not interested.” That was it. It’s all these ranges in between. But to get to that point you have to truly understand why. What is this? Why am I doing this thing?
In the early days, I think that’s a tricky one. Maybe that’s a good measure or a good answer to, Courtland, your question earlier. How do you know what to work on? Maybe you start with figuring out why and what. What are you trying to build here? Why are you doing it?
If you’re doing it because you want to be financially independent, the number’s not that big. For most people, it’s not going to be, I need a million dollars a year or some crazy number. If you’re doing it to be in control, you don’t need to be a 600-person company. You could do that with three people.
There are all these things that if maybe as an early founder you stop to say, “What’s the point here?” Cause you get to say that. That’s the whole point of being a founder. 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. I’m “leaving money on the table.” I’m air quoting here. And that’s okay. We’ll grow a different way. But that’s 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?” There’s nothing that would destroy me more if my name was anywhere near something like that.
But that’s just my choice. I get to design it, but I’ve had those moments of true clarity. Chris and I have gone away and sat down and wrote copious documents of like, “Well where do you want to be? What about three years, five years? We have kids now. How long do I want to keep working?”
You start writing it down and it definitely changes things. But I don't know if we did it very much. Well I know that we didn’t do it in the very early days. It was like, “Oh, I’ve got to build a business. I don’t want to go to college.” That was it.
There was no big, grandiose plan, and maybe that’s why you chase things in random directions, because it’s hard to know where you want to go. I don't know that at 19 we would have been able to say where we wanted go. That changes when you have families and when you get older and see things a little bit differently.
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 come in from the outside world. They come in from your social group, your peer group, your environment.
I live in San Francisco. I’ve talked to a lot of founders here. A lot of people are chasing this billion dollar unicorn status for no other reason than that everybody around them seems to put that on a pedestal. I think it’s extremely important to be mindful about that.
But David made a point earlier that we never quite resolved, which is that you as a founder also have an effect on your team. They 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 that 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 practical sense, this is going to sound funny but Chris used to send an email on Sundays to the team. He would have some crazy idea on something. He was like, “We should build this.” And he started sending these emails on Sundays. It would always be Sunday because we had a weekend and his mind’s racing.
At one point we were like, “You have to stop doing that. You’re totally wreaking chaos. Who talked about that? I think Dharmesh maybe talked about that once, where he would send a bunch of shit around and everybody’s like, “You gotta stop.” Oh, no, it was Hiten.
Hiten Shah, yes.
Hiten said it.
It was Hiten bombs.
Yeah. That’s right. And so I think from a very practical sense, they say that founders cast a big shadow. It’s truly understanding what you’re doing. Some of that we just don’t let go back. Remote work helps, but some of it we don’t let that go back into the system. We 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 work less than the team. They definitely take a cue from me but in the early days, when we were obsessed, we were a very small team. We were working with people who were excited about what we were building.
We all collectively, to be honest, had to remove some of those habits. When there were five of us, it was a collective. This was a long time ago. They were building a product in Rails, and it was exciting. It was like, “Oh my gosh. We’re going to this thing. We’re going to host people’s code. They’re going to think that’s crazy. We’re going to do it anyway.”
There was this immense energy. We untangled ourselves out of that partially by having lives. We started getting married, having kids, and realized very quickly that’s not the reality that we want, but also slowing down and figuring out that there’s purpose and meaning.
Now, we take a tremendous amount of vacations. I’m always focusing on the team. I think my problem now is that I find my team working more than 32 hours sometimes. 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 loud and clear that, “You’re not my mom, and if I’m excited about something I would like to be able to work on the thing that I want to work on.”
This was challenging for me, but I found that I have to say as long as it’s not consistent, as long as it’s not burning out, as long as it’s not causing any issues on your family, I’m not going to be your mom. I’m not your mom. But Wildbit 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 adjust the scope. So that's where I’m trying to find balance.
Sometimes those things are tricky, but that’s the message consistently, over and over again. If the reason you’re working more or you’ve 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.
We’re going to stop that thing. We’re going to re-adjust 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,” I’m not going to be like, “No, please wait until Monday morning at 9:00 a.m. to touch that.”
They’ve pushed that back on me pretty heavily, which was funny because it’s how my brain works too. There’s moments where I’m like, “Chris, watch the kids. I gotta go write this thing.” That’s okay for me because I feel like that’s my job, that’s my business.
They’ve pushed back on me and said, “We promise we’re okay. We’ll let you know if things are getting out of control, but sometimes we want that opportunity to be inspired and go to great work. Please don’t stop us. That would be ridiculous.”
Completely agree with all that. It’s true for myself as well. That’s why I like this averaging out concept, that an individual week spiking is not a big deal. You take it up some other week or you take it out some other week.
I do that all the 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. I think that makes total sense and why it’s important to zoom out and look at long term trends and not be an hour Nazi on the per-hour basis of it. Just see, is there an overall sustainable trend here?
And then to enforce that with being what you want to happen. Natalie, as you say, now being someone who doesn’t work those crazy hours, it was the same for Jason and I. If we wanted people to take vacation, we had to be authentic about that and take vacation.
In earlier years we had this very misaligned or poorly thought out idea of unlimited vacation days. This was in the early 2010s or something. What ended up happening was no one took any vacation, because they purely took their cues then from what someone else was doing.
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 racetrack 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 there. That adds up to weeks and weeks out of a year, but it didn’t add up to, I was offline for three weeks straight.
So people took the cue that, “Oh, I should not take two and three weeks’ vacation. That’s clearly not kosher.” And when we found that out or at least internalized those lessons, we were like, “Well yeah, that’s dumb.”
So now we have very explicit vacation time and just say, “Hey, you should be taking this time. Hey, here’s some free packaged vacations that we’ve designed for you that you can take. We’re going to pay for them. We’re going to do all these other things to encourage you that we’re not just saying these things. We’re doing these things. We mean these things.” I think everything we’ve talked about, we’re so much in alignment here. The only point of contention would be to back this out to include day one founders.
If you promise to average it out.
I promise to average it out and I’ll give you 6 to 12 months to average it out.
Not 20 years.
We’re in complete agreement, and also again, accounting for where the time is spent I think was really an important point, Natalie. If you are including, “Well, this is the time I spent reading, or this is the time I spent tweeting in general,” fair enough. I would clearly also at 50 or 60 hours if you took all the influences or activities I could take that could possibly make me a better executive or make me a better programmer or make me a better human.
That would make me a better executive and a better programmer. That’s probably true. So it’s not like there’s the 40 hours and then all rest of my time is lying perfectly still doing nothing. That’s not a thing.
Not with three kids.
It’s not an ideal I try to put up, either.
David, most of the people listening to this 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 your closing message for somebody who’s in that situation and has that mindset?
Know 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 your feeling were not true of the US in the 70s and 80s. It was not true - well that’s 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. You might have feelings of guilt. This is society 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 what I enjoy doing.
It’s your second job.
Bringing a message, saying, “Hey, we’ve got to realign this. We can.” The current myopia in particular with startup founders, particularly what they hear out of San Francisco, VC-funded companies and so on, there’s deprogramming that needs to happen.
It’s like if someone was in a cult. They learned things that were not true. So first of all, you’ve got to tell them all the things that were not true, that they’re not true. Then you have to 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. There’s a lot of others like you and it feels like you’re all in it. It feels like you have a place to belong.
Do you know what? You can find a different place to belong. I’m trying to have one place. There are 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, VC, 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 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 don’t think your brain is processing fairly or even usefully.
I think, for me, and for any founder starting out, just as 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 creating space to think. So I have empathy for those early days. I think over this conversation we ultimately come to an average where we agree.
But 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 in clear thought, with clear thought. Spending more time thinking about what we want to build and why we want to build it, and what those real goals should be and what kind of business I want to be in, instead of thinking about the product and how are we going to ship it and how are we 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, identify where you were trying to go.
If that is, “I just need enough money to support myself,” well then 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 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.
So 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 didn’t stop to think about why. Why did we want to do this? What were the ultimate goals and how far did we want to run?
Those conversations you should have with yourself frequently. In 20 years, that was not one conversation. That is a continuous conversation of what 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 launched a next 10 year strategic plan. So here’s the next decade.
That’s my problem. I’ve got another decade in me, and then I don't know what’s going to happen. I might open a hotel or something. But you can’t have those conversations without stopping and creating quite space for yourself.
So those moments where people know us and get excited about all these things we do, they didn’t come from chaos. They came from calm times thinking about stuff and the faster you can get yourself to there the more success will be an option, a viable option versus the statistic of failing. Whatever that failure statistic is, it’s so scary.
Well 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 what other things you’re working on.
Sure. It’s called Hey, H-E-Y. It’s hey.com. We are in crunch mode right now. It’s pretty crazy. It’s eight hours a day, five days a week. Already right there we’re working 20% harder than Natalie’s team, which is funny because that’s leading up to, we launch in April and May 1st we start our summer hours, which is also a 32 hour work week 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’s wonderful.
I’ve been emailing for a good 25 years at least. I don't know if there’s any other protocol outside of HCDP 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.
I 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 paid product. It’s an email server that allows you to escape Gmail and all these other things, and love email again.
So that’s what I’ve been focusing on for almost, what has it been, 18 months? We’re coming up on the final two months here now of running it. 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 [email protected] and that’s how you get on the list. There’s no way we can just type in your email address. You’ve got to send us a story. About 30,000 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 is when it’s coming out.
Who’s processing those emails?
We’re filing them all into essentially a monster spreadsheet. I forget what we’re using, some system where if you send an email, it goes into the system. Just reading through 40,000 stories is something, so we’re just cherry picking out of it. It’s just going to be the list.
The funny thing that the gift here, at least as I have heard it from some people who have sent the message was it allowed them to reflect on what they like about email. So it was more of 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 similar position to David. You had just released a brand new product called Conveyor. Can you let listeners know where they can go find out more about what you’re working on today?
Yeah. We’re working on a fun side project right now called People First Jobs, peoplefirstjobs.com. David’s seen it. It’s going to launch hopefully around April 1st, at the end of March.
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. People would come and look for a job and the emails would say, “Well if not you then who else? I want other companies like you.”
We want to focus on behaviors and less on perks and benefits. So 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, flexibility, and benefits, absolutely, as well.
But I think a lot of job boards don’t pay attention to the behaviors. People ask in interviews or find out too late that these companies don’t create the fulfilled environment that they want. So we’ve been spending a bunch of time talking to tons of companies, talking to job seekers which is really fun and asking questions like what’s missing in a typical job posting?
That’s been fun. Those answers are fantastic. We’ve been sculpting this thing, hopefully launches at the end of March. Our team’s been working hard, but it feels fun and special. We’re talking with some great companies. We’ve 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 excited.
So we’ll see. But it’s meaningful work. Wildbit is on this big 10 year strategic plan, and the big realization for us was that Wildbit doesn’t have to be a software company. It could be a company of really smart people doing work that they care about.
So 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, then understanding what the profits are for and then generating a back end to other work.
So 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. So we have these four day work weeks. What are we doing on the fifth day? Thirty people times one day. In 52 days, that’s a lot of time that could be spent doing meaningful work for our communities, for ourselves as human beings, for each other.
So it’s just a lot of fun stuff. The plan is starting to come together, and it’s 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.”
It’s not money. That’s fine, but what’s going to keep me here so that I’m 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 multiproduct.” And when you guys were like, “Hey,” I was like, “Okay, good.”
You know, things change. 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.”
So that’s just one, but there’s a couple projects coming out this year. The rest are secret, but the teams had a lot of time to play. So we’re still very focused on our products and they’re growing well, but we’re having some space for some more fun things, and that’s been wildly exciting.
Super fun to hear both of you talk about the way you run your companies and what you’re building. I’m looking forward to using all of this stuff. Thanks, David. Thanks, Natalie, for coming on the show.
Court, thanks so much. This was great.
Listeners, if you enjoyed this episode, let me know on Twitter. I’m @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 hash it out and talk through it. Thank you so much for listening, and I will see you next time.
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