Remote Work Interviews

Conversations with leaders and innovators about how industries and organizations think about the future of remote work.
How HubSpot Is Building Remote Work Into Its Company Culture
Katie Burke: Chief People Officer at HubSpot
Why It Doesn't Have to Be Crazy at Work
David Heinemeier Hansson: Co-Founder & CTO of Basecamp
March 19, 2019
Interview by Sophia Bernazzani
Photography by David Heinemeier Hansson
David Heinemeier Hansson is the co-founder and CTO of Basecamp, a project management and team communication software designed to help teams work together calmly and productively.
David Heinemeier Hansson is the co-founder and CTO of Basecamp. He's the creator of the web application framework Ruby on Rails and has co-authored several books about remote work and the future of work, including REMOTE: Office Not Required and It Doesn't Have to Be Crazy at Work. In this interview, he speaks with Owl Labs about the future of work, why remote work will evolve to become the way business is done, and why ambition can be a weakness for some entrepreneurs, instead of a strength.

Owl Labs (OL): For those of our readers who aren't already familiar with your career, you created the web application framework Ruby on Rails, you're co-founder and CTO of Basecamp, and you've published several best-selling books, the most recent of which was It Doesn't Have to be Crazy at Work. My first question is, do you sleep? My second, more serious, question is, how did your career trajectory evolve from programmer to thought leader?

David Heinemeier Hansson (DHH): To answer your first question, yes, absolutely. Sleep is one of those underrated keys to success– I was going to call it "trick," but that's too Silicon Valley. Sleep is a basic human need that many entrepreneurs and people in the tech community have been neglecting for too long.

There's also been a general contempt for it in some ways – lots of people think that, in order to get more things done, you need to put in more hours to be more productive. When people believe this, they take advantage of every hour that's available in their day for working, and put sleep on the back burner. They might work for 40 hours at the office, and then put in an additional 40 hours outside of the office, and they think they've created a solution that only requires them to sleep for five or six hours a night each week.

I think that's absolute nonsense. We take a different route at Basecamp, and remote work and sleep are both a part of that conversation about how to use the time that you have more efficiently, rather than try to add hours to your work day. Eight hours in a day and 40 hours in a week should be enough time, and getting sleep is critical to being the most well-rounded and cognitively present person you can be at work.

In terms of my history, I started working on Ruby on Rails and building Basecamp back in 2003. Our origin story of Basecamp, formerly known as 37Signals, was made possible with remote work. My co-founder, Jason Fried, started a company called 37Signals back in 1999 with three other co-founders in Chicago, and they started a blog called Signal v. Noise that's still publishing today, 20 years later. At the time, I was in Copenhagen, Denmark, a fan of the company and a reader of the blog, and in 2000 or 2001, Jason posted a question on the blog about PHP.

I had done some PHP hours, but I knew the answer to that question, so I wrote Jason back. We started emailing back and forth, and he very quickly decided it was easier to hire me than it was to learn how to program, so we started working together remotely, seven time zones away. In fact, for the first six months of working together, we never even spoke on the phone, it was all via email or instant messaging. After six months of working together, we finally had a phone conversation, and after a year, we met in person.

I continued working out of Copenhagen as we started working on Basecamp, and the whole company was founded on the remote work concept that time and space don't really matter when it comes to building cool products and productive teams. In fact, we came to see working remotely an in different time zones as an advantage, not a disadvantage. Once I started working full-time on Basecamp, in the mornings before my teammates in Chicago woke up, I would have several uninterrupted hours when I started working in the morning when I was extremely productive. Then, later in the day, I would have three or four hours of overlap with the team in Chicago, when we could catch up and collaborate using instant messaging and virtual meetings.

We quickly realized that uninterrupted, solo productivity time was incredibly important, because when I moved to Chicago to work with the team in 2005, I started coming to the office, where I was getting less work done. At the time, we had a traditional open office in Chicago, and I found I couldn't get good work done there. So shortly thereafter, I started working from home again, even though I had moved from Copenhagen to work with my teammates in Chicago.

Even though we had an office, even though we were in the same city, and even though we had all the tools we needed for physically working together, I realized that working in an office wasn't a  great way for me to work, and it wasn't a great way for us to work as a team. So as we grew the company, we maintained the remote work ethos and kept hiring people wherever they lived. We would – one of the first programmers we hired was from Boise, Idaho, which isn't exactly the tech capital of the world, nor is it a commuting distance away from Chicago. It was simply where a great programmer happened to live.

Today, we're a team of 54 people at Basecamp, and only about 12 of them are in Chicago. On any given day, there may be three of them who go into the office, and the other 50 work wherever they're most productive which, in most cases, means working from home. In some cases, it means working from a coffee shop co-working space. That's how we came to build a remote company– not because that was some ideological choice we made, but it was a necessary one, because I was in Copenhagen and we wanted to work together. That experience made us realize that it was a better way to work, which we've carried with us in the nearly 20 years since then.

Sleep is a basic human need that many entrepreneurs and people in the tech community have been neglecting for too long. Lots of people think that, in order to get more things done, you need to put in more hours to be more productive. When people believe this, they take advantage of every hour that's available in their day for working, and put sleep on the back burner.

OL: What do you think other entrepreneurs and founders can learn from your experience when it comes to building a company – whether it's remote or co-located or hybrid – that's less about grinding and hustling, and more about building a sustainable business that allows you to enjoy your life outside of work?

DHH: That's the question that motivated us to write our latest book, It Doesn't Have to Be Crazy at Work. Our story of building Basecamp, the story that I've known for almost 20 years, is how we've grown from small software company of 4 people in the beginning, to a sustainable company of 54 people today, earning hundreds of million dollars in revenue over the years. I could not and still cannot find my mirror in the tech industry ethos of success, entrepreneurship, and heroic depictions of what entrepreneurs are supposed to look like. We identified that mismatch between what companies that do well are supposed to look like, and what our team looked like, and thought we had a bigger story to share.

We lead a company of 54 people who are happy working for us, Jason and I are very happy and involved with the business, and we have over 100,000 very happy customers. This seems like a way of working and living that should be normal. It shouldn't be this exotic thing when co-founders and employees only work 40 hours a week or, or when a company fully embraces remote work. We wanted to make a compelling, cohesive case for why entrepreneurs should consider that path.

For me, how you build and run a company is heavily influenced by your perceptions and beliefs when it comes to ambition. I believe there's been a dramatic hyperinflation in entrepreneurial ambition, particularly in the U.S. and when it comes to startups. We've narrowed the acceptable range of what entrepreneurs should be aiming for down to unicorn – a private company with a valuation of over $1 billion. That's it. Every tech company should be striving to become a unicorn, and if they're not on their way to becoming a unicorn, they're some degree of failure. That's a very impoverished view of entrepreneurship if you ask me.

If we're only focusing on achieving unicorn status – which only about 300 total companies have – we end up deeming any company that doesn't achieve unicorn status a failure, and we end up squashing a lot of good ideas and people in pursuit of that.

We wanted to try to reset what else being ambitious can look like as an entrepreneur. You shouldn't have to apologize for wanting to build a wonderful, small-to-medium sized, sustainable business that you can run for 20, 30, or 40 years, without ever having the aspirations of becoming a unicorn or hiring thousands of people.

We've narrowed the acceptable range of what entrepreneurs should be aiming for down to unicorn – a private company with a valuation of over $1 billion. That's it. Every tech company should be striving to become a unicorn, and if they're not on their way to becoming a unicorn, they're some degree of failure. That's a very impoverished view of entrepreneurship if you ask me.

DHH: We live our beliefs and values in a few ways at Basecamp. For example, we don't believe in goals and KPIs. A big thing at most companies is KPIs – key performance indicators, and BHAGs – big hairy audacious goals. There are so many metrics for measuring the business, which the team constantly has to beat, month over month and year over year.

This strikes us as an unnecessarily stressful treadmill. If you meet your goals one quarter, there's always another quarter coming up with even higher goals. That's the nature of quarters– there's four of them per year, there's 40 of them per decade. If you're constantly on a path where things have to get bigger and grow faster and faster, and then grow exponentially, because that's the only way you can get to unicorn status, companies can end up in a dark place that leads entrepreneurs to encourage shady business or leadership practices because they're under so much pressure to get results.

When company leaders are under this much pressure and have started to cut corners to achieve goals, they may start engaging in behaviors current unicorns have been caught up in – whether they're mistreating employees like Uber or abusing user data like Facebook, there are so many pressures to obtain the maximum from your company and its employees because leaders are stuck on this treadmill of ambition. We wanted to send out a message to say that it doesn't have to be like this.

First of all, building a small company that brings in $1 million a year and can support four people should be considered a wonderful success. In fact, when I look back at my entrepreneurial trajectory, I had as much fun if not more fun on the days when we were a team of four people as I do today when we're 54 people.

The memory of the good ol' days is a powerful thing for entrepreneurs. We talk to lots of other founders who like to reminisce about the early days. They recall the times when they could act fast and weren't tripped up by the bureaucracy of a larger company, and in remembering these times fondly, they sometimes reflect on the day-to-day of their current job and wonder why they're doing what they're doing.

One of the reflections I often use when I talk to entrepreneurs who have starry-eyed unicorn dreams for their companies is by asking, "Do you think Mark Zuckerberg is enjoying his job? Do you think he's been having a good time at Facebook for the last three years? Is that where you want to end up?" My guess is, probably not, and there's a long list of company leaders who I think are enjoying themselves a lot less now than they were when they first started out. Entrepreneurship can be less than exploding cars and action scenes all the time while still being successful. You can be ambitious and want to create a 20-person company that focuses on the simple, mundane aspects of doing good work.

At Basecamp, we curtailed our ambition about a year and a half ago, when we decided we were big enough, and didn't want to get any bigger. We've actually instituted a hiring freeze on the day we celebrated the highest revenues Basecamp had ever had. We didn't do a hiring freeze because things were going poorly, we instituted a hiring freeze because things were going well. Jason and I both came to the realization that we liked to do the work aspects of our jobs. I like to program, he likes to do design, and at 54 people, we can spend a material part of our day doing those things. But if we continued to grow the company to the point of 100, 200, 300, or 500 people, we wouldn't be able to do the work we enjoy anymore. You can't be an executive leading a company of 500 people and also spend the majority of your time programming. So we decided we were big enough, and we stopped hiring.

And again, we wanted to broadcast that message that that was acceptable, and not a declaration of failure by arresting your appetite for endless, exponential growth. Unless you have a conversation with yourself and the people you're working with about what is enough, nothing may ever be enough, and you may already be off to a bad start. The second part of that equation is, once you've clarified that world domination isn't your one solitary ambition, and that you don't have to capture every single customer that exists in this world, then you can focus on what happens in the day-to-day at your company, and making those 40 hours per week count.

Once you've clarified that world domination isn't your one solitary ambition, and that you don't have to capture every single customer that exists in this world, then you can focus on what happens in the day-to-day at your company, and making those 40 hours per week count.

OL: Not on working more than 40 hours for the sake of growth alone.

DHH: Exactly. There are so many entrepreneurs who are obsessed with getting more hours out of the day.

I don't wish there were more than 24 hours in a day. In fact, there are plenty of hours in the day, and I only need 8 of those for work. That's enough. There's an obsession with the quantity of hours that people dedicate to work, which leads to some of the terrible stories we hear that are presented as though they're aspirational. I remember Marissa Mayer bragging about how she preferred working 130 hours a week, which only required her to be strategic about when she took showers and bathroom breaks. That doesn't sound like the life of a successful executive who's worth millions of dollars to me.

The human body is simply not built for the sort of exhaustion or physical abuse that comes from working that much in a week, but when we have celebrated executives from the most successful companies on the planet endorsing these practices, it's essentially being endorsed as an aspirational lifestyle – the lifestyle of working yourself to death.

Even since the very early days, at Basecamp, we've always said that 40 hours is enough, and we focus on making those 40 hours count. If you're only focused on getting in more hours of work, you're not focused on the quality of each individual hour of work – which is what really matters. Most people simply don't have more creative juices in their body than they can expend over four or five hours during the work day. In fact, I'd say a day where I can spend four or five dedicated hours digging into one task or problem, uninterrupted, is a fantastic day.

There aren't any ways to squeeze out three times as much of that in a single day. I don't know any programmers or writers or leaders who on any sustainable basis can extract 12 hours of truly productive time, day after day. It just doesn't happen. The human mind isn't built for that, even if your body could keep you awake and alert for that long. But we keep laboring under the illusion that that's possible – that you can go three times as fast if you work three times as long. But the truth is, if you attempt to do this, you'll only go maybe 80% as fast as you would normally because you end up adding net-negative value to your pursuit.

If you're a programmer who keeps working after already putting in 12 hours, you'll end up putting more bugs in your software that other people then have to spend an inordinate amount of time pulling out of the software the next day. If you're a writer, you'll keep writing crap you have to rewrite or spend hours editing the next day. So many people who work in the tech industry don't focus on what the output of their work is – they're only focused on what the input is: how many hours they're putting in. What does it matter what we're putting in? Shouldn't you be focused on what we're putting out? When we do look at what we're putting out, we'll come to realize that the model for what is healthy for humans and how to get them to their peak creativity and satisfaction is nothing novel or groundbreaking.

For 100 years, people have been studying workplace dynamics. In the 1920s and 1930s, Henry Ford realized that even on the assembly line making the Model T, forcing workers to work more than 40 hours a week ended up being counterproductive. They made more mistakes, got injured, and weren't effective. We had a roaring-age capitalist recognize that 40 hours in a work week was enough nearly 100 years ago, so it blows my mind that now, in the 21st century, we have a new crop of executives who think they know more than decades of scientific and academic research, all of which say the same: that leaving time for sleep, recuperation, creativity, exercise, and personal enjoyment are all critical to building a happy and productive workforce. It's bullsh*t.

Decades of scientific and academic research say the same thing: that leaving time for sleep, recuperation, creativity, exercise, and personal enjoyment are all critical to building a happy and productive workforce.

OL: Speaking of, I saw you recently called out a CEO on Twitter who was sending Slacks to his team members, compelling them to come into work on weekends if they weren't on track towards hitting their KPIs for the month. How should company leaders be responding if they're tracking behind on goals and metrics?

DHH: My biggest issue with that CEO was the phrasing he used in his message to the team. He said, "The KPIs we agreed upon aren't being met." What do you mean, "we"? A big issue I have with the modern vernacular around work is how executives couch conversations about goals and targets by saying, "We're all partners, we're all peers, we're all family here."

No, we're actually not. If you're a CEO who has the power to fire people, and you're telling your employees what goals they need to meet and when, and you're couching it in pseudo-friendship language, you're actually doing everyone a disservice and being abusive. At least the robber barons and their managers didn't make things confusing or unrealistic – they simply said, "come do this job or you're fired."

Now, we've couched modern workplace communication in a cotton candy language that's used to camouflage how unreasonable leaders' demands can be. If a CEO puts out unrealistic targets and goals, somehow it's a moral failure on the part of the workers if they're not living up to the metrics set by company leadership in response to the board of directors or the stock market. It's abusive, it's counterproductive, it doesn't work, and it should be called out.

Calling out bad behavior and poor business practices out is part of what we're trying to do with both the book and on social media. If you call things out enough, you will eventually change the culture. We've seen this happen over and over again in different domains because culture is very changeable. When you're one small part of a culture, it can seem like it's an immutable force that no single individual can have an impact on, but now, that's not true.

Think about the #MeToo movement, for example. Ten years ago, powerful people in the film industry were getting away with horrible things, and if you were a part of that culture, it likely didn't feel like things would ever change, and that there was no way to hold these powerful people accountable for their actions. And then all of a sudden over the last few years, people have been held accountable and punished for their actions thanks to the courage and strength of many individuals coming forward and speaking up. There was a change across the entire culture because of the actions of individuals who said, "Enough is enough. Time's up."

I think something similar can and will happen with work practices. I've started to see those cracks forming from the stories individuals are sharing about big, successful companies doing bad things, and I'm encouraged that we see more of those stories every year. And by virtue of the fact that, in the U.S., we're almost at full employment, it's very easy to get another job in the tech and creative industries, which means that people have options and don't have to take bad behavior from bad bosses. They can change jobs.

Part of the mission that we've taken upon ourselves is to educate people about the fact that work isn't like this everywhere. Unfortunately, sometimes workers fall into a sense of learned helplessness, where they keep working in a known abusive environment because they think that's what work is like everywhere. And we want to call out just how untrue that is, so people know that there are companies with different ideals and practices that are inspiring instead of stressful, and as the title suggests, work shouldn't feel crazy. So we wrote a manual for things to look out for when you're thinking about leaving your job, or taking a new one.

If you call things out enough, you will eventually change the culture. We've seen this happen over and over again in different domains because culture is very changeable. When you're one small part of a culture, it can seem like it's an immutable force that no single individual can have an impact on, but now, that's not true.

OL: I'd love if you could go into more detail about the ways you reinforce reducing craziness internally within the team at Basecamp, whether that's done at team all-hands meetings, or by setting working hours using Google Calendar, or by setting "Do Not Disturb" hours on Slack. How are you evangelizing and setting an example of what not being crazy at work looks like?

DHH: Even if you buy into the value system that I've presented, you still have to learn and build the skills and the mental frameworks to do it effectively. These are specific techniques and tactics that you can use to curb ambition somewhat, and we refer to it as protecting your time so you're able to do good work during working hours, instead of being forced to work longer hours to get things done during your personal time.

One of our strategies for protecting people's time is by skipping the game of calendar Tetris at Basecamp. At most companies, calendars are shared and open, so every employee sees each others' schedules and set meetings during their colleagues' open blocks of time. When everyone's time is available in that way, it's hard for people to plan their days around doing their best work, and instead, they get pulled into meetings. We want coordination and taking other people's time to be manual, annoying, and difficult.

Here's how we do it: If you're trying to coordinate a meeting between four people, there's no technology to help you do it. You have to contact each person individually and ask if they can meet during your proposed time. And if someone says no, you have to keep going back and forth with everyone to find a time that works. In short, it's a pain in the ass. Because you can't see everyone else's calendar, you're forced to do this manual song and dance to set a meeting, and that's exactly how we like it, because people won't go through that inconvenience unless they really need to hold a meeting. The policy also helps communicate that that open space on someone's calendar doesn't make them available for wasting time. The default policy is that open space on someone's calendar means they're working, which in most cases, is a better use of time than a meeting. Not all meetings are bullsh*t, but many of them are. They can waste time and cost money in terms of company resource allocation, when people already have plenty of work to do on their own.

Another technique we use to protect people's time is we don't hold status meetings. We think they're a poor use of working hours because, after explaining what you're working on in five to 10 minutes, you spend the rest of the time listening to other people do the same. Status updates are much better when they're written and shared amongst the team, because then, people can read the updates at their leisure when it makes sense for their schedule. When you leave people's time open for capture with open calendars, and when you encourage that capture with things like status meetings, you end up punctuating people's day in a manner that's completely unproductive.

If you take a work day, and then you break it into work moments, by scheduling meeting after meeting, with only hour-long spurts of free time in between, if you need a little time to get into your working flow, your day will fly by, without getting much done. Other companies might encourage you to work additional hours from home, where you can work uninterrupted into the night, but instead, we use those strategies to protect our employees' 40 hours each week so they can use their mornings and evenings for self-care, recuperation, spending time with family and friends, and of course, sleeping.

We've also instituted office hours at Basecamp to protect people's time. Many companies make it as easy as possible to reach anyone else in the organization to ask a quick question or to chat, and it institutes a de-facto policy of being available at any time to answer work questions, and of taking the liberty to interrupt everyone else, constantly. It holds back people's own learnings, too. If you're encouraged to ask your colleagues questions as soon as they pop into your head, not only will asking that question interrupt the person you're messaging, it also keeps you from trying to find the answers to questions and learn something new on your own. In this way, we avoid a crazy organizational structure where people's time is punctuated by meetings and interruptions all day.

Instead, we use the concept of office hours, where experts within the company set aside a dedicated period of time each week where they make themselves available to answer questions about their field via chat. That way, if you're working on a new feature in our product and need the assistance of one of our Javascript experts, you can book time with them during the time in their schedule they've designated as office hours, where they're available to be interrupted if needed.

It encourages people to think about their questions and prepare for chatting with the subject matter expert ahead of time, which invariably leads to a clearer conversation, or even independent learning. It also allows people to arrange their schedules so they can plan for interruptions and get heads-down work done at other times during the day.

All of these ideas work together to protect our employees' time, and not simply for the sake of protecting the number of hours each of us has during a day. The ultimate intention is to protect the integrity and connectedness of time during the work day so our team can take advantage of back-to-back hours in their schedule for deep productivity, rather than endless interruptions from meetings and chats.

One of the nightmare scenarios that could happen with greater remote work enablement would be if people are shackled to work 24/7 simply because the technology makes that possible. And if there's no clear boundary between work and life, we'll end up working way too much.

OL: A lot of companies are building policies to enable remote work, flexible schedules, and working from home. Do you think that's a step in the right direction towards making work less crazy, or do you see examples of remote work being used in a way that further reduces work-life balance? How can companies build remote work policies that lead to greater productivity and improved work-life balance, instead?

DHH: Remote work has the promise of being much better, but unfortunately, that promise can go unfulfilled in some cases – and sometimes, it can very well end up worse. One example of this is live chat, which can make things better or worse for a company trying to implement more flexible work policies.

Chat can be a wonderful tool for getting those quick answers and working collaboratively on the fly, but just as easily, it can become an oppressive river of disruption for everyone's attention. If you constantly have to keep half an eye on a scrolling chat window, it's very difficult to dedicate all of your attention and focus on the task at hand. That case is where chat can, unfortunately, be one of those tools that ends up making remote work worse than working in an office.

You need to establish ground rules around how and when chat is used within a company. What kind of things do we use chat for? It shouldn't be used to make material decisions, for example, when only those employees paying close attention to the chat window can participate in the discussion.

That's one of the limits we put on chat at Basecamp: It isn't used to make important decisions. Instead, if you have something important to propose or address, you have write it up. We write up full memos and present complete ideas to other people, give them the opportunity to digest those ideas, and respond in their own time. The problem with chat is that most discussions within chat are by their very nature in-the-moment ideas and knee-jerk reactions. Most decisions are better-made, and most contemplation is higher quality, if it's allowed the time to percolate first.

A couple years back, Jason wrote about the idea of giving everything five minutes. Because an instinctive human reaction to new or discordant information is to reject it in response, chat shouldn't be the medium for presenting and discussing those new ideas, because chat is predicated on the idea of thinking and responding in the moment. Instead, if you set the expectation that colleagues should think about new ideas and proposals for a day, before reconvening in a meeting to discuss, you'll get better digestion of ideas and better collaboration over solutions.

Another key aspect of enabling remote work in the right way is by doing it in a way that gives employees more freedom, not less. When they start allowing remote work, many employers are concerned about what people will do with that freedom. They have ideas in their heads that everyone is going to goof off at home by playing PlayStation, doing laundry, or watching TV. But if you have a healthy company culture, in most cases, the opposite will happen, and remote workers will end up working too much without a clear delineation between work time and personal time. It may not seem like much of an imposition on your personal time if you keep answering one-off emails and chats into the nights and weekends, but simply because work can happen anywhere with today's technology doesn't mean it should happen anywhere. You shouldn't have to be available to work while you're at your kids' soccer game, out to dinner with your friends, or anywhere else you take your smartphone during your personal time.

One of the nightmare scenarios that could happen with greater remote work enablement would be if people are shackled to work 24/7 simply because the technology makes that possible. And if there's no clear boundary between work and life, we'll end up working way too much. What we've found at Basecamp is that we have to explicitly remind and encourage everyone to work a 40 hour week 75% of the year, and then during the summers, we work 32 hours a week because we take Fridays off. We set and repeat the company-wide expectations: Don't work on the weekends. Don't send people emails at 10 p.m. expecting a response. Companies can set good examples in employee handbooks and within teams, but if the CEO and the executive suite are online and sending emails out at 2 a.m., that will trickle down into workaholism, so these practices need to be modeled from the top.

That is the dystopia of remote work – the worst case scenario where we'll be worse off than we were when you had to wait until Monday morning at 9 a.m. to address the company because the technology that enables remote work will also enable our own workaholism. But when it's used for good, remote work provides the promise and opportunity of giving people more autonomy and control over their lives to integrate work the way it fits best. That way, when kids are sick or errands need to be run, taking a couple of hours away from work during the day won't prevent anything from getting done. People will be able to have calmer lives, at work and at home, where work can be integrated in a balanced, sustainable, and healthy way, instead of being driven by the whims of a demanding boss or workplace culture.

The idea that you can't develop a culture if you're not all sitting together all the time struck me as completely unimaginative. If you perceive your company culture to be the foosball table, catered lunch, and ping-pong, you're not understanding what actually makes up a strong company culture.

OL: What are some of the biggest misconceptions about Basecamp and how you've built it, or just about building remote teams in general? What do people read about you and immediately think, "That wouldn't work for us"?

DHH: The most common opposition to our description of work is, "That's easy for you to say now," because our business is so established. People sometimes think we've reverse-engineered calmness now that we've reached a certain point of maturity and growth, and that when we faced difficulties as a business, we put in more hours. People have an instinctive gut-reaction of disbelief when we share our story of how we work, either because they're a new business, or they're stressed out by the goals they have to reach for.

People don't believe me when I say we've never worked 120-hour weeks even when we were bootstrapping things, which I find so profound. It's profound to me that saying we work a traditional 40-hour work week is met with disbelief. People are so trapped in the idea that, in order to successfully build a company, you have to put in heroic quantities of work as simply the table stakes for life as a startup founder or entrepreneur. People think it's not a choice, and we're pushing back on that idea and saying, it is a choice – and it's one that all companies should make.

When you're the person starting the company and setting the policies, everything is absolutely a choice you can make. At Basecamp, we've made a lot of choices about how we structure our organization and how we've massaged our culture to be one that protects time and ensures we can all be as productive as we need to be within 40 hours each week. Making it feasible in someone's mind that working this way is possible is a surprisingly difficult step – let alone convincing them that this way of working is better than theirs.

In my opinion, this is an affliction that's unique to the American workplace. There are plenty of companies built throughout the rest of the world where people don't work like this, and there are plenty of prosperous companies that propel complete societies to be healthy and happy and wealthy without adopting the practices we see burning out employees here.

Although this sense of disbelief is unfounded, it's unsurprising. It's the same disbelief that led us to write our previous book, Remote: Office Not Required, back in 2013. We were met with utter disbelief when we proposed that successful companies could be built completely remotely. One of the early push-backs we received when we shared how we worked successfully as a remote company was that it's impossible to build and maintain company culture if employees are distributed.

The idea that you can't develop a culture if you're not all sitting together all the time struck me as completely unimaginative. If you perceive your company culture to be the foosball table, catered lunch, and ping-pong, you're not understanding what actually makes up a strong company culture. There's a difference between material perks and culture, which we believe is the sum of what we do and how we act and who we are when we work together. Those concepts are incredibly malleable and designable, whether you're sitting together in the same office or whether you're working remotely around the world.

In my experience, company culture is easier to design when you're all working remotely because you have to write things up and document processes and policies. You have to commit, in writing, to what your values and techniques are so everyone at the company can understand them. Our belief in the value of documentation is what led us to write the books, both in a practical sense of describing what we do, and in an aspirational sense of reminding ourselves and others what we should do and what we should value.

There's growing skepticism about the fact that technology isn't an inherently good thing, and successful unicorn companies aren't inherently worthy of praise. These companies and innovations are worth our skepticism, investigation, and sometimes opposition, and the readiness with which users and journalists are digging into that gives me hope for the future.

OL: Are you optimistic about the future of work being less crazy and more flexible? Do you think the tech industry needs another stock market crash to happen for people to stop chasing IPOs and unicorn status so easily? What is your outlook on what the landscape of work will look like 10 years from now?

DHH: I'm very optimistic about the future of remote work because it's starting to shift to become the default option at a lot of organizations. Most companies being founded and built today realize it's much easier to start out as a remote company. First of all, you don't build up a lot of organizational plaque that you have to scrape off once you convert to a remote culture, such as changing communication protocols and collaboration frameworks that have to evolve to fit the medium.

Second of all, it's just cheaper and easier to do than starting a co-located company. You don't need to rent office space, you don't have to buy fax machines or chairs, and there's a lot less friction getting in the way of simply starting to do the work. So I'm encouraged by the companies I'm seeing starting out, or evolving, into fully-remote companies.

Unfortunately, the jury's still out on whether it's the type of remote work that's being adopted is healthy or unhealthy. In some ways, it's possible to end up with a fully-remote company that's worse off than a co-located one. Part of our eagerness to share our version of what the healthy version of work, and remote work, look like is so we can influence those seeds that are being planted right now that, in ten years, will turn into the next defining companies of our industry. Our industry and our workforce need those seeds to be planted in fertile soil and not turn into distorted industry outgrowths that aren't healthy or happy for anyone.

I'm less certain about if we can arrest the sense of  ambition hyperinflation that forces company founders and leaders to chase the wrong numbers in pursuit of the current definition of "success." You may actually be right that we could require a full reset – a crash, a recession, or a cautionary tale –  before some of the worst behaviors and excesses are pulled back.

Right now, the people who play the game are being rewarded lavishly for it. Right now, it doesn't matter how many people they burn out, or how many billions of dollars they burn through. It only matters if they can grow their top-line revenue, and as long as we're stuck in that mode of institutional reward, we're going to see more employee and user abuse, more excesses, and more companies that don't pay attention to some of the fundamentals of building a strong company because they're being rewarded by the markets either way.

Look at a company like Uber, which is likely one of the most culturally bankrupt companies to make it to unicorn status, and those corporate and culture transgressions have done nothing to arrest its ascent. Uber will IPO, and I'm sure its leaders will be rewarded lavishly, and that's the market sending the signal that none of these things matters – only revenue does. It doesn't matter if you abuse your employees or your customers or their data, so long as you're bringing in money.

That's an unfortunate reflection on the nature of late-stage capitalism, and I don't think crashes are generally good things for countries and markets. They don't usually end up hurting the people who should learn a lesson – in many cases, crashes end up hurting employees without millions of dollars with stock portfolios and 401(K)s. But sunlight is the best disinfectant, and the economic party over the last decade is likely coming to its own end naturally. My hope is that, if we hit a recession soon, companies learn to fix bad behaviors so their employees don't jump ship as readily.

Cracks are forming in the ubiquitous startup and tech company culture in the U.S. that values the hustle and the grind. Now, where Uber and Facebook were previously revered as companies that were connecting the world, there's growing skepticism about the fact that technology isn't an inherently good thing, and successful unicorn companies aren't inherently worthy of praise.

These companies and innovations are worth our skepticism, investigation, and sometimes opposition, and the readiness with which users and journalists are digging into that gives me hope for the future. The fact that journalists and the media industry have woken up to that, instead of simply being cheerleaders for the tech industry, helps provide users, customers, investors, and regulators a critical lens through which to view the innovation that's happening so quickly, we don't always notice if it's being done exploitatively. Greater transparency and a healthy dose of skepticism give me reasons to be optimistic.

Key Takeaways


1. 40 hours a week should be enough time for employees to get their work done. If it's not, your metrics for success or your quantity standards are off.

David firmly believes that the key to achieving bigger and better metrics and growth isn't putting in more hours – it's done by dedicating working hours to work quality and productivity so leaders and employees are able to focus and think at work, and recharge and rest during their limited personal time.


2. Remote work policies should be used to give employees greater flexibility and work-life balance, not so they can put in additional hours every week working from home during their personal time.

David hopes for a future wherein remote work policies are widely adopted as a way to give employees the freedom and flexibility to build work around life, instead of the other way around. That said, he sometimes sees remote work policies and technologies used to compel employees to be available for work at all hours of the day, which he believes would be an inappropriate application that leads to workaholism.


3. Use tools like office hours on chat to protect employees' time during the work day so the team can work as productively and free of distractions as possible.

At Basecamp, the team isn't allowed to check out each others' calendars and book meetings on a whim, and they're discouraged from sending chats on an instantaneous one-off basis. Instead, Basecamp employees set office hours on a weekly basis, so they can set aside time for answering colleagues' questions without being distracted constantly throughout the week.

To learn more, read our interview with 15Five Chief Culture Officer Shane Metcalf next.

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