Who is Jason Fried?

He is best known for co-founding Basecamp, a Chicago-based web application company that built the quite popular project management tool. He also co-wrote New York Times Bestseller Rework in 2010 with his business partner David Heinemeier Hansson, the creator of Ruby on Rails. Fried has been writing on the Basecamp blog for over a decade. Lately, he’s been writing always-honest, sometimes-controversial opinion pieces for Inc., covering everything from startup investing to why he gave his entire company a month off.

If you’re part of the startup and tech community, you know all of this already. You use Basecamp (and Highrise and Campfire). You’ve read Rework. You’ve shared Fried’s blog posts on Twitter. But, beyond the media gossip, blind opinions, and edited articles, there is a lot we never get to see or understand about popular startup founders.

So, really, who is Jason Fried?

I sat down with Jason to ask some of the questions we all want to know the answers to, but journalists never cover. Fried is perceived as wildly intelligent, hyper productive, and fiercely opinionated—but perhaps ego-driven, and a bit of a rebel without a cause. Some of that is accurate, but many likely misunderstand why Jason does what he does.

His genius lies in his ability to lead Basecamp with a maniacal focus on building only the best, most essential products and features; he is the ultimate editor. He is a minimalist at heart, with an eye for impeccable design. He is highly productive—but only because he can’t stand the feeling of wasting time; not because he thinks about “how to be more productive” the way so many of us do. He is fiercely opinionated—but not for the sake of controversy. It’s true: he tends to fight against archaic business mentalities like “more is more,” and “remote work is bad work.” But, his ideological assertiveness comes as a result of knowing that no one listens to or respects a founder who wavers—one who responds with “that depends” when asked the hard questions.

The thing that surprised me most during my interview with Fried was the number of times he mentioned his team. You can tell he is thinking about his team first and foremost whenever he makes a big business decision. The happiness and intellectual stimulation of everyone at Basecamp is what drives him—it is the reason he remains so focused, productive, and purpose-driven. It’s easy for a founder to say, “I care about my team.” But, when you hear Fried talk about the people he works alongside, it’s clear that he really means it. If Basecamp was a family, Fried would be the protective older brother.

In this exclusive interview, Jason shares his thoughts on: leadership, fears, (mis)perceptions, productivity, the future of our country, and why Basecamp will likely never go public.

If you want to better understand Jason Fried, keep reading.

Leaders are split evenly between a heavy emphasis on market research and a heavy emphasis on gut—where do you stand?

I’m very much towards gut. I think that you need to be in tune and feel the pulse of how people perceive your product, and how they use your product, and the problems they are really solving with it. I’m not data-driven. I’m not someone who looks at numbers to make decisions, but I look at trends and patterns to lead to new insights. I don’t take numbers as a “yes” or “no,” but they’re a part of what I do. Often times we’ll do things that the numbers say won’t work. Numbers can only measure what’s happened in the past. That’s valuable to know, but you have to trust your gut moving forward—otherwise you’re just going to be running in place.

What were you doing in between the time that you graduated from college in 1996 and started Basecamp in 1999?

A year before I graduated, the Internet started to take off and everyone was a beginner. I just started figuring out how to make websites and learned HTML on my own. Back then, it was really easy because there wasn’t anything fancy about it. I started doing some freelance work in college; I went to some websites that I liked and used, but thought could be designed better. I would email the websites and say, “Hey, I’m a designer. I think I can redesign your site and make it better for $500.” I picked up a couple clients and one of my clients offered me a full-time job as a designer in San Diego. My degree is in finance, but I didn’t want to work at a bank. So, I took the job and moved to San Diego for a while, but realized three months in that I wasn’t built to work for other people. I’ve always had jobs; ever since I was 13, I’ve been working. But for the first time, when I graduated from school, I realized I could do my own thing. I quit after 4 months, moved back to Chicago, and continued to do freelance website design until 1999, which is when I started Basecamp with two other guys.

What was the trigger that ultimately led you to start your own company? Did you have any fears?

No fear, actually. The fear for me was continuing to work for someone in a capacity that I didn’t really want to work in. What scared me was the idea of spending my day working on something I didn’t really care about. Taking a leap and starting my own company was more of a relief than something I was scared of. I wasn’t planning on hiring anyone—it was just me. At the previous job, I was getting paid $30,000 a year. So I thought, “If I can find a way to make $30,000 a year on my own, fine.” I think if I started a company and thought about hiring five people right away, the expense would’ve been too high. I didn’t even think of it as a company at first. I just wanted to figure out how to pay my rent, eat food, and have fun.

Did you have any trouble looking for a technical co-founder in the beginning, given that you had more of a design background?

If you haven’t done the job yourself, it’s very hard to hire for the job because you don’t really know what you’re doing. So, I always recommend people try and do the job first themselves so they at least understand a little bit more about what they’re trying to hire for. While I’m a designer, I’ve learned how to program over the years.

The reason I met David, my business partner, was because I was learning PHP and I got stuck, so I asked for help on our blog. He responded and helped me through the problem. I really like the way he approached programming and thinking about elegant code. I realized what I was struggling with, and also that David knew what he was talking about, so that’s how that came together.

But, if you’re completely blind to what you’re trying to hire for, it’s really easy to make mistakes when you hire people. If you don’t have experience with something else, it’s very hard to find someone who is good at the other skill. It is very easy to think that anyone is good because they know more than you do. But, it’s not about how much you know; it’s about the things you know and how you apply them. So, do the job yourself first.

What are some of the assumptions you’ve made in the past about work and life in general that you wish you didn’t?

I think it’s easy just to assume that you know the full story about some things. For example, I’ve learned that it often comes down to how customers use your products. We just assume that people understand our product or use it in a certain way because we [at Basecamp] use it in a certain way. And when you go out to talk to people, you realize that they use things entirely different than the way you expected them to.

It’s really easy to get stuck in the loop of just assuming that everyone is like you and if you do it one way, then everyone is going to do it that way. Lately, I’ve been spending more time listening to the stories behind why people use our products and realizing that there is a whole different set of assumptions people have coming into using our products than I thought they might initially. That’s been really eye-opening for me. You have to challenge the assumptions of what you think people are using your product for.

Is there anyone you feel you have to answer to, even though you’re running Basecamp?

Ultimately, it has to be for the customers. But, I don’t think about answering to anybody or anything. At the end of the day, you have to think about if you’re enjoying what you’re doing. It’s not really an answer—it’s more of a feeling: “Do I feel like what I’m doing is meaningful and am I satisfied deeply by this work?” Not every day—you have to do things you don’t want to do sometimes. But for the most part, I just want to make sure I am excited to go to work most days.

I also have certain values—I care about quality, clarity, and treating people well. So, as long as I’m excited to go to work, I can hold myself and the company to a high standard. Everything else just flows from there: that we’re going to make great products, treat customers well, and treat our employees well; that we’re going to keep a team together for a long period of time, and we’re going to run our business our own way and not have to answer to investors or markets. We’re going to do what we think is right, and hopefully that works in the long-term.

You are perceived by many as someone who is calm, cool, collected, and unfazed by others’ opinions of you. How true is that perception? Is there anything that stresses you?

First of all, that’s a skill you have to build up over time. I used to have much thinner skin. But, the thing that still gets to me is being misunderstood. When I see someone saying [Basecamp] made a decision as a company because of X, or that we’re writing more on our blog because we are trying to sell more ads? It’s not true, and that really bugs me. It’s always gotten to me. I feel like we always have our best intentions at heart. When I hear people say things like “37signals is just a marketing company. Their products are fine, but it’s all about marketing,” that kind of stuff bugs me still.

Personal attacks don’t really bother me because I know who I am, and I can’t control things other people have in their own minds.

The thing that stresses me out is that I have a lot of ideas, and I have a hard time dealing with the inability to act on all of them. I think a lot of entrepreneurs have this. I am also impatient, and that’s hard because it takes time to do something well. I am a really big believer in keeping teams together, so I worry about my employees a lot: Are they happy? Do they want to be here? Are they doing the best work of their lives? How can I allow my employees to do better work? How can I make the work more challenging?

That’s the stuff that’s important to me and keeps me going at night. Business is solid, so I don’t worry about numbers day-to-day. That’s just not the kind of person I am.

And it helps that Basecamp is a private company. 

That’s intentional, too. All companies start out this way, and some lose their way. It would be the worst part of my day if I had to worry about what the market thinks of our company, or what our stock price is doing. I don’t wish that on anybody. I have no interest in running a company like that, ever. These are conscious decisions you have to make as a leader when deciding what kind of company you want to run. You have to make sure you’re in control of those decisions; otherwise, you’re not running your own company—you’re running someone else’s company.

What is the greatest misperception you think people have about you and Basecamp?

That people think that we think there is only one way to do things—and that’s partially our fault for being outspoken. But that’s just something that comes with being outspoken: you have to take a position and you don’t want to always say, “It depends.” That’s not interesting or a good way to make a point.

I think there are hundreds of ways to do things. People who are far more successful than us are doing things completely differently than us. There are a lot of ways to do things right, and a lot of ways to do things wrong. All we have to share is our own experience about how we built a company. We’ve been in business for 12 years, and hopefully people see that there is something to learn from what we’ve done and that what we’re doing does work, but it’s not the only way.

Has growing Basecamp changed you at all since you started the company in 1999?

It hasn’t changed me much, I don’t think. But you’d have to ask other people because it’s hard to be completely honest when you’re speaking about yourself. There is a quote I like that goes something like this: “Success doesn’t change you; it reveals who you are.” I don’t think I’ve changed; I’m the same person I’ve always been. I’m growing as a person because I have more responsibilities and I’ve had more experience. But, fundamentally, the same things that have driven me still drive me today. It’s not things like money, ego, or success; it’s about quality, being proud of the work that I’m doing, and being able to create a company that people enjoy working at.

Is there anything you do that has made an enormous difference in the quality of your work and level of productivity?

It’s weird because we make tools for this, but I don’t think about productivity. Fundamentally, you have to understand what it is you are spending your time on. The thing I hate the most is wasting time. I want to make sure that whatever I’m putting my energy toward is meaningful. It doesn’t have to be profitable; it’s not about that. It’s more about, “Am I getting somewhere? Am I moving forward with this, or am I just spinning my wheels and wasting time?”

As long as I’m not wasting time, I feel good. For me, being productive is just about making sure that whatever I spend my time on is valuable and meaningful. That could be talking to an employee, coming up with a new idea, sharing an idea, refining a feature, or editing an article. I just want to make sure that whatever those things are, I’m making good use of my time.

Spending an hour on something meaningful is a far better way for me to spend my time than spending 10 minutes on something that’s not meaningful. Even if I’m spending more time on the hour, that’s fine for me. That’s how I think about things. And, that’s why I can’t stand paperwork or lawyers.

How do you want to be remembered when all is said and done?

I’m too young for that question! In general, that I was thoughtful and cared about my work.

You still have a lot of time to create. In that time, what’s the impact that you most hope to have?

I’m really starting to enjoy seeing people I work with grow. It’s something I never thought much about until the last couple of years. I would love to see some of the people that work here get better at what they do, and if I can help them think through things and find better ways of doing things, that’s really satisfying to me. Lately, I like sitting with designers, working through problems, and helping them see something they haven’t seen before—usually, ways to make things clearer or simpler. I love editing. I think the CEO job is really an editing position. To me, editing is the unheralded skill that makes the best people, the best. You have to edit down ideas and concepts. Everyone has big ideas, but you can’t do big ideas all of the time. So, how do you figure out what’s essential about an idea? I love that process.

People say Steve Jobs was great not because of the products he created, but rather, that he was ruthless about eliminating bad ones. It sounds like the process of editing you’re talking about.

Steve Jobs was a great editor, I think. Whenever I see an Apple product, the first thing I think about is all of the things it doesn’t do. I can see where they made decisions. Apple’s products have very clear decisions attached to them, unlike a lot of other products which try to do a lot of things and just add on more features. Most brands I really like have that editor at the helm who has a certain taste or vision or outlook on things. That’s where the best things come from. For example, a band could go into a studio and record 30 tracks, but they have to edit it down to 12. That’s what makes the album great: not the 30 tracks, but the 12 tracks.

When we wrote Rework, it was originally 40,000 words and we cut it down to 20,000 words. That made the book better. You can also over-edit, so you have to be careful not to go too far. But in general, editing well is what makes something great.

Lately, there has been a ton of cynicism about the future of our country. What are your thoughts on the future?

There is significant structural change that is happening in this country. We can’t keep thinking things are going to go back to the way they were, or that they should go back to the way they were. Things are changing and they have changed. There is a lot of romanticism around the way things were, and I think that just has to stop. Things move forward.

The good thing that I see, though, is that there are some wicked smart people in this country. I have a lot of more faith in the private sector than the public sector. I’m more of a libertarian kind of guy. I think the government serves a role, but I prefer more private sector innovation. If you look around, that’s where the more interesting things are happening. People I meet who are 21-years-old are way smarter than when I was at 21, so that’s always optimistic.

The biggest danger I see is complacency, and success breeds complacency. This country has had a lot of success over the last 100 years, so you get complacent—it’s just a natural tendency in humans. You have to have enough of a value system to realize when that’s happening, and to fight it. There are a lot of other parts of the world that are far hungrier than the United States right now—and hunger beats complacency almost every time. So we just have to make sure we don’t get too complacent. As long as we’re aware of that, I think we’ll be fine.