This is an auto-generated transcript of Never Enough Podcast Episode 3. It may contain minor errors.
Andrew: Dude, what's going on? What have you been doing today?
Jason: Well, I recorded a podcast earlier with someone else, which was good. I'm just kind of trying to wrap up—going on a little quick trip up to a renovation project I'm doing up north a bit. So every six weeks or so I got to go up for a day or two to review current work on a project and then come back.
Andrew: What's your usual day look like these days? Are you busy? Are you chill?
Jason: Been a little bit more chill, although I'm about to get busy—we're about to work on some new products. So that's kind of a fun thing. But it's been fairly chill this year so far actually. I would say I'm trying to take a little bit more advantage of free time during the day because I've got kids, and at night it's basically right after work, it's all family time. And the weekends are actually not that open either. So kind of during the day is sort of my open time.
Andrew: You guys a couple years ago released Hey, which is a really awesome email client. And then you guys just launched Hey Calendar. I'm curious—why launch a calendar product?
Jason: My wife has this huge paper calendar in our kitchen for our whole family. It's better than any digital calendar I'd ever used. Kids could scribble on it, we could put stickers on it, like we could look forward to things—"it's like 10 days to Hawaii" and there's a countdown on each day. And all these things that you're like, why can't digital calendars do this? And why on digital calendars does a doctor's appointment I'm dreading have to be the same as a birthday party I'm looking forward to? Like, they're just these bullet points with times. Everything's treated like it's going to be a meeting.
Andrew: You had a tweet the other day that was really interesting. You've built this huge software business over the last 25 years. Financially you've been incredibly successful. I would assume that you have enough money that you don't need to keep working. You wrote a tweet about why you keep going and what drives you. Can you talk about that?
I've always been motivated by being pissed off at something, frankly. I just got on the board of the HOA—the homeowners association. I got on the board and I looked at the budget and I saw that we're spending $10,000 a year on this software and it just pissed me off. It was just like—why is this acceptable? It's not. It's just purely not acceptable. I've always been motivated to just make much better versions of things and charge very very fair prices for them.
Jason: Like with Basecamp, for example—you cannot pay us more than $299 a month, period. You can have 9,000 employees. We cap the amount you can spend at 300 bucks. Hey's $100 a year. I just don't like the idea of software being expensive. If you can build something at scale, typically price should be coming down. Software is one of these things that you basically build once and you replicate a billion times for free. It just bugs me that something like that should be expensive.
Andrew: I remember one time I came to you and I said, Jason, I'm doing this software company and I want to give you free shares in it. I sent you the docs, the contracts. And you just said, "I don't want to do a contract. I don't want to deal with that. Just tell me that if something goes well, you'll take care of me later." You more than any other entrepreneur I know—you don't do stuff you don't want to do and you've structured your life and your business in a way where you never have to. Where does that come from for you?
Jason: I value independence, basically. Independence for me means the ability to do what you want to do, how you want to do it, and not have to answer to anybody else or have to ask for permission. I'm financially independent at this point, so I don't need 3% of your company. I just want to help you because I like you, we're friends. I don't need the financial ties to it.
Andrew: What about that Airbnb investment you turned down?
Jason: I was offered the opportunity to invest 100 grand into Airbnb when Airbnb was running out of their apartment originally. I think they had like eight people. I didn't do it at the time because I didn't want to go through the process of the paperwork. And also they weren't profitable, and for me it was important to invest in profitable businesses. I mean, looking back now you can see—but it's cost me money in a sense. I also was offered 1% of Intercom for advice. I didn't do the paperwork.
Andrew: Externally looking at you—I always go, Jason's got it all figured out. Obviously you don't. What are those areas where you still get frustrated?
I don't have it all together. With work we have it pretty together. But there's things I don't know how to do—like we've grown our business to a certain level, I don't really know how to grow it beyond that. And I don't need to grow it beyond that, but I really don't know how also. I've gotten much better at acceptance—just like, I don't know how to grow a business beyond the business I've grown. I'm not some great CEO. I'm just the guy who knows how to run this business. I fit into this suit. I don't fit into some other suit. I fit into this one really well. It's tailored for me. And it works. I'm okay with that.
Jason: People will often tell me, "you guys have left so much money on the table and you guys could be so much bigger." And I'm like, yeah, probably right. I don't really care though. And maybe that's just because we've gotten very lucky and we don't have to care. I'm perfectly okay with that outcome too.
Andrew: About 10 years ago you guys announced that you were going from multiple products to focusing just on Basecamp. It's exciting to see you in this moment of expansion. Tell me—when you guys made that decision to just focus on Basecamp, what happened over those 10 years that caused you to start all these new products again?
Jason: We went all in on Basecamp and either folded existing products in or spun them off. Built an extraordinarily good version of Basecamp—Basecamp 3, and then Basecamp 4, which is the best version we've ever had. But I found that working on one product—I thought I was going to love that—we made it really, really good, but every once in a while you have a new itch. I found that I just don't want to suppress. I don't feel good when I suppress.
At our core, David and I and the rest of the company—we make things. We're makers. We like to make new stuff. And sometimes what happens is you come up with a direction or a strategy and you stick to it because you made the promise to yourself. But then you end up cheating yourself because you're stuck to something you said in the past that was true back then but is no longer true. So we had to eventually be honest with ourselves again.
Andrew: Is there a fantasy of not doing what you're doing?
Jason: Yeah.
Andrew: Was that too quick of a yes, by the way?
Jason: Yeah, very, very quick. The industry that you and I are in—it would be insane to think about closing a business that does tens or hundreds of millions of dollars in revenue. But there's this tiny part of me that thinks it'd be amazing just to close the business.
Andrew: I was going to catch up with you because I know you've hired a bunch of CEOs to run businesses. I've not done that. I don't know how to do that. I am afraid I wouldn't trust someone enough to do that, and I'm afraid that I would get in the way actually.
Andrew: It's really hard. You think about it as—your business is like a child and a new CEO is like a foster parent. Except it's a foster parent that you watch. And some foster parents abuse your children, some dress them in ways you would not like. And some of them are wonderful. And it's really hard to predict what you're going to get.
Jason: So it's kind of like the difference between being the owner of a soccer team or the star player. And being the star player is really cool, but it's also stressful and hard on your body. So it's a hard decision.
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