Jason Fried On Writing, Profitability, AI, and the Most Improbable Thing He’d Like To Do (but Probably Can’t)

Jason is the co-founder and CEO of 37signals (the parent company of Basecamp and HEY). During our talk, we discussed what he learned from his recent sabbatical, his views on writing, the future of AI and its implications for creativity, and more.

Jason Fried On Writing, Profitability, AI, and the Most Improbable Thing He’d Like To Do (but Probably Can’t)

It's not every day you get to chat with a legitimate legend. But that’s exactly what happened when we sat down for a Q&A with Jason Fried in a recent episode of our show, Subscription Heroes.

Jason is the co-founder and CEO of 37signals (the parent company of Basecamp and HEY), as well as the best-selling author of four books about work, design, and building calm companies. During our talk, we discussed what he learned from his recent sabbatical, his views on writing, the future of AI and its implications for creativity, and more.

Here are the key takeaways and biggest insights from our conversation with Jason.

As you’re coming off a four week sabbatical, what’s been most on your mind while you get back into the mix?  

Well, it's been good to know that the company can run without me. Not that I imagined it couldn't, but it's confidence-inspiring to know that you built a great team, you've got a great company, and things can run. So that was a wonderful realization to come back to. 

Also, whenever you come back from a break, you just see things through fresh eyes. I see some of our messaging, even messaging that I wrote, and realize it feels a bit dull. I want to get back and sharpen some things up. And I think there’s no way to really notice that stuff unless you’re away from it. 

Tell us a little bit about your sabbatical. What did you do while you were away? Did you read any biographies, watching anything inspiring?

I read a couple of books that are not business-related at all. But I typically don't read business books anyway. Mostly I went on a lot of long walks and just didn’t think about anything intentionally. Initially I had planned to take drum lessons, learn some Spanish, do all these things I’ve wanted to do. But then I realized that’s just work also. I decided that I didn’t want to work on anything for a bit. I thought, “what if I have nothing to do and nothing intentional to deal with?”.

And it was really nice to literally just walk around, to just be, and not really have anything on my mind that was important. And then if I came across something I wanted to check out or read or see, I would do that. I also went on some long drives. I like driving, but I haven’t really had the time to go out and drive lately. Normally, you wake up, you’ve got your kids, you take them to school, you’ve got work, you get back, you have dinner, then it's dark. So being able to go on some drives and not feel like I have this scheduled thing that's coming down on me in 35 minutes was actually quite nice as well. I think I'm so used to filling my time with things to do, so it was nice to literally have nothing to fill my time with.

I’m impressed by how much you write. How do you feel about your motivation for writing? Do you write for yourself, for your own satisfaction?

Basically, I write what I’d want to read. I have to write something that I wish existed, essentially. And I don't write as a hobby, so I wouldn’t be someone to write a novel or short stories. That’s not really my thing. I just like to share my point of view through writing. I've always written about what's been on my mind and tried to be direct and conversational about it. And some of the things I write could be six or seven paragraphs, it could take five minutes. Sometimes it can take an hour. Sometimes it could take a week of thinking about it and putting it down. It just sort of depends.

I think the best things though just flow out. There are no drafts. You just get it out there and move on, as if we’re having a conversation. But I think the most important thing I’ve found is that you have to write what you want to read and not write for anyone else. Otherwise, I think you're just beginning to imagine what other people want. And I don't think any of us are very good at really figuring that out.

When you’re writing something, if it’s not a one-and-done situation, then what’s the process?

If I’m writing something that’s going to have a permanent place on our website or something that has a really strong point of view, then I’ll usually toss that back and forth with David or someone else, try to get some feedback. But if it’s a blog post or something for Twitter or Medium, that's just extemporaneous writing. Very, very rarely would I share that with anyone ahead of time. 

The other thing is that I don’t write on a schedule. It’s not like every week I have to produce two or three things. Sometimes I'll go for weeks without writing anything. Other times I'll write a few things. Right now, I’ve got three topics on my mind I would love to write about this week, if I get a chance to. If I don't get a chance to, I'll do it the following week, or I’ll fall out of love with the ideas and they just won't ever get written. So that can happen too.

One of them I’ll go ahead and tell you about ahead of time… it’s about performance reviews. People will ask me how we do them and how often we do them and how we decide if someone makes the cut after a period of time. For me it always comes down to one question.

I usually give people about a year to sort of find their way — sometime a little less, sometimes a little more. But around that amount of time you can do performance reviews and look at all sorts of metrics. And then you can also ask yourself one question that answers all of them: “would I hire this person again?”. Would you rehire that person and would they rehire the job? Are they happy they made the choice to come here?

So I definitely want to write about that. Maybe I’ll do it this week, maybe I won’t. And maybe I just won't find enough to say. That's the other thing that happens sometimes. If I only have a paragraph or two, I’ll usually just write it up on LinkedIn as a comment or a thought versus using it as a post. But there’s no formula. It's just kind of what flows through the fingers.

Now do you still write all of the copy for the company?

I still write all of our marketing sites, all the key pages. There are some pages on Basecamp that I haven’t written and some stuff that was changed on the homepage, so some of that isn’t mine. But the top five pages on the site (landing page, pricing page, features), that’s me. That’s actually one of the things I enjoy doing most. I like coming up with new ideas and building new products. And then I love figuring out a way to talk about them and trying to connect with people who are shopping for them. So I would say that’s my primary contribution these days. 

I know you used to write out the UI first. Are you still doing that as the zero point or has the pitch taken the place of that?

So the pitch is always written. It's never performed, there’s not a meeting where I explain it. It’s written down. Sometimes there are maybe a few sketches to support the writing, to explain something visually. But everything always starts with writing. And the idea, the feature itself, a big part of it is deciding how we would write the screens. How would we explain what this is? Sometimes we’ll actually design the UI in words first, in a sense. Some features are more conducive to doing it that way. Others really need to be drawn out. But it shouldn't require anyone to have to re-explain or to explain it in a different way. So if we can't get it clear enough, then the feature probably isn't ready.

To me, that’s a staple of your products and one of the many reasons for your staying power. And it’s been almost 24 years now. What is your playbook for staying relevant and evolving?

Number one is that we've always run a profitable business. Staying power, at the most fundamental level, means “do you make more money than you spend so you can pay your bills?”. For us, when it comes to running a profitable business, it means keeping our headcount small, keeping our costs low, charging money for our products, not giving them away for free, and figuring out how to make money later. And then delivering a really high level of service, delivering unique products with a unique point of view. 

Then there’s the prolific sharing we’ve been doing for many, many years. We share without expectation of return — write books, write blog posts, do podcasts, share our insights, share design reviews, share code reviews, share as much as we can to show people how a business is run, and how we run ours.

I don't know which are the fundamentally most important parts, but I think it's a combination of all those things. You have to run a sound business, you have to make good products, you have to treat customers well, you have to treat employees well. I think also the mindset is important. We want to be there for the long-term. We've been here for almost 25 years. Can we be here for another 10, 15, 20? Hopefully, but I don’t know. But the mindset is that we’re here to stick around. We're not here to leave. And I think that is really important.

I’ve got to ask about the AI stuff. I know you've said in the past that computers will eventually program themselves. Do you think there's any way you can embrace AI?

I think there’s a real shift that’s happening right now. I don’t think we’re quite sure what’s going on with it yet, where it’s going to go. I think what’s going to be really interesting about AI eventually is more on the personal side of things. Like if you had a personal assistant that really understood your style. Once it gets to the point where you feel like you have a second brain or a second pair of hands that are yours, I think then it becomes very, very, very interesting and very, very useful. Because then it can really do things for you in your own style, in your own way.

Until then, it’s interesting, it’s fascinating. But I don't know how we would use it quite yet. I think the summarization stuff is pretty interesting. But the things is that we don't write super long documents that need to be summarized. We don't have 90-minute meetings that need to be summarized. We don't have long transcripts that need to be abridged. So it doesn't really lend itself to the way we work currently.

But I think it’s interesting, and I can see how people are adopting it. It makes a lot of sense, especially in big corporate environments where there's a lot of stuff going around that people don't have a chance to read. Frankly though, Midjourney is more interesting to me. The visual side of it is really fast, and I find that to be more amazing. But also… these are just tools. In the same way that a computer is a tool. Everything is a tool, and it's a great tool to have in the toolbox. I think it's going to unleash a lot of imagination and allow people to do things they could only think about before, but now they can actually do.

One more question: what’s the most ridiculous or improbable thing you want to do that you don’t think you ever will?

I would love to do a three month silent retreat. It’d be incredibly hard. And in my life right now, I simply cannot see how that could ever happen until my kids are out of the house. But I would love to see what that would be like.