Jason Fried on fixing email

... and the amazing freedom of NOT building something for a billion people


July 21, 2020

(10 min read)

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A year ago I started looking for an alternative to Gmail (cuz: tech giants disenchantment etc). I checked out Proton, Fastmail, Tutanota, and another half dozen. Most of them felt like a flashback to the 1990s, and not the fun kind of flashback. In the end, I settled on iCloud / Apple Mail. But after six months, I gave up and went back to Gmail - found myself once too often in a place where I was in a hurry to dig up an old email and it’d be nowhere to be found.

So I started asking all my friends: "don’t you agree that email sucks? Let’s go build something better." And they talked me out of it: "Email is for old people. Young people don’t use it. Why go build AOL Dialup? Nobody uses email for communication. It’s just for signing up to online services and for newsletters. Gmail is fine. Gmail is BIG. Good luck matching all those features. And then you’ll need to build a backend, and it’ll cost you $20m a year just to keep that up and running. And if you charge for the service, you’ll have a tiny business." 

Then I woke up a month ago, and there was Hey. OMG, somebody did it! And they did it SO WELL. I friggin love it. It’s fun & has attitude. It kind of imposes a new workflow on you, and if you go with it, email will no longer rule your day.

So I called up Jason Fried, the cofounder & CEO of Basecamp. Ruby on Rails was built there. And Basecamp. And now Hey. I wanted to find out they did that.

The conversation starts with email, but it gets to broader insights around how to build great product and great culture, and lessons learned as an entrepreneur.

Bart Decrem: Email has been driving me bonkers for a long time. I was always asking: “Can somebody just build an alternative to Gmail? Why can’t we do that?” and people kept telling me it’s an impossible problem… and then you did it. Hey is amazing.

Jason Fried: Thank you. Reinventing email is a very hard problem, which is why people don’t take it on. And it’s also historically been a terrible business because it’s hard to compete with free, but there’s enough people who understand that free doesn’t really mean free anymore. Free means you give up your privacy. Free means you give up a lot of control. Free means big, huge brands or big companies are deciding what emails you should see. There's a lot of cost to that too. So we think at a hundred bucks a year, we can make a good business out of this and provide a really nice private, simple system for people. With a whole bunch of different takes on what email's all about.

Bart Decrem: Many people (me!), when they think of building successful and interesting products, want to build something that can reach a billion people and that to do that their products must be free… but I think there are times when you need to be willing to say “I’m going to build an amazing product, and I’m going to charge for it” or “my product is going to be for a very specific group of people”.

Jason Fried: Yeah I agree. Our feeling has always been, "Why do you need to build something for everybody?” It's an almost impossible task. And also it waters it down actually. So Gmail has 1.5 billion email users. At $100/year, if we get to 100,000 users, we can make a wonderful business. And 200,000 people have already signed up. We can build a wonderful business on this because our economics are different. We don't have 7,000 employees. We have 56 people at Basecamp. So we don't need to build something that's massive, for everybody. We can build something wonderful for some people and it can be very profitable and we can do a great job and take really good care of it and make something great. And to me, that's always been what's interesting - to build what you want, not what everyone else wants; build what you want and then find other people like you, who want something very similar to that.

That's enough for us. We don't need to dominate. We don't want to own everything. That's our point of view at least. Granted, you need companies like Mozilla and Google. There's a lot of things in the world that need huge, massive scale. We're just not interested in scale. In fact, I don't want it, which is why we charge for our products, so we don't run into the situation where we have billions of people using our stuff and that's a whole ’nother hard business to run.

Bart Decrem: But there's no way that this thing is not a big, scary bet for your company of 50. Email is completely monopolized. So how did you get to Yes on that idea?

Jason Fried: Because email sucks, that's why. And if everyone loved email, we wouldn't have done this. But you ask anybody about email they’ll say: "Oh my God, it sucks. I'm overwhelmed. I'm under a big pile of email. I'm always behind." I’ll ask: "How do you mark something to get back to someone later. What do you do?" and they’ll go: "Well, I mark it unread." Well, that's a workaround. Email's full of workarounds, it's not full of workflows. And people don't like email. It's not because email isn't great. Email fundamentally is great. And you know that because whenever you get an email from someone you care about, it's great to get that email. The problem with email is everything else.

Email is a wonderful thing and it deserves a refresh. It deserves some real attention from a company that actually gives a damn about it. And that’s us. Email is the most amazing thing because it's the universal common denominator across organizations of all sizes, across countries, across cultures. If you want to send someone a message, email is the best way to guarantee or be as close to guaranteeing that you can get it to someone else. SMS doesn't work that way. All these other things, they're not universal. The thing about email is, no one owns it. And that's why it's wonderful. And the thing is that there's so much opportunity to improve it.

When Gmail came out, it was a great improvement, but it hasn't changed much since. It's time to reignite what's great about it and do some brand new things and bring some new thinking to it. And I feel like the entrenched players, they don't really care about it that much. They think it's a solved problem. It's not a solved problem if everybody hates it. So anyway, all that stuff and our own personal frustrations about, "Why is this so hard? Why is this such a workaround? Why is this such a hassle? What can we do about that?” And so we set out to solve it and we absolutely think we have, with Hey.

Bart Decrem: That brings me to my next question - how have you guys built your culture? How do you create a culture where you're able to be this contrarian and willing to wait two years and expend X million dollars as opposed to trying to derisk it by doing something a little smaller or an extension or “a quick MVP”?

Jason Fried: Culturally at Basecamp, we're actually pretty risk-averse. We've been in business for 21 years, but we have one massive hit called Basecamp. Basecamp generates tens of millions of dollars in annual profits for us, for a small business. So Basecamp gives us the cover to do some strange things occasionally, like spend two years building an email system, which is what we just did with Hey. And if Hey didn't work out, we'd be okay because we're not putting the company at risk. Our culture is to take risks, but not to put the company at risk.

Bart Decrem: What are the three things on your wall that you live your entrepreneurial life by?

Jason Fried: Well, I think the things that I've learned have all come through, like realizing that most of the things you worry about don't matter anyway. There's a lot of work that you do that’s keeping you busy, but that’s unnecessary.

Next, most people have simple problems. Sometimes technology tries to make these problems more complex than they are. We've always tried to build the simplest possible things to solve basic problems that people have. I'm not interested in solving an email problem for the edge-case emailer who emails 4,000 people a day and has to run all these scripts and shortcuts. That's not what we're doing.

One of the real problems with software is that software has no edges and no limits, which is what's exciting about it, but also it's the biggest problem. Nothing is naturally pushing back on you to say, "Enough." 

One of the real problems with software is that software has no edges and no limits, which is what's exciting about it, but also it's the biggest problem. Nothing is naturally pushing back on you to say, "Enough." For example, if you had a bottle of water and it was heavier than you could hold, you would know that's a bad design. You'd be like, "Too much water or the bottle is too heavy. Or the shape is too weird." You would know naturally, physically, that that's not a good design. So physics pushes back on you. But with software, nothing pushes back on you. So you can keep expanding this thing to make it as big and as complicated as you want and there's no natural pushback. So you've really got to be very careful and have the discipline to say, "Enough. These are the problems we want to solve, let's solve them really well. We'll learn more as we go and we'll fix other things as we go. But what is the basic problem we're solving for each one of these things? And let's stop there and not get carried away."

Last thing is that small teams are critical. So at Basecamp, any feature we work on, no more than three people work on it, that's it. In most cases, it's two people. It's a programmer and a designer. One to one, that's it. The bigger the team, the more people involved, the more complicated it gets, the slower it gets. It doesn't get done faster. It gets done later. So small teams also help keep your discipline in check to make sure that you don't take on too many things that you just can't do. So that's our approach. Those are the things I've learned. I've learned other things, but that's fundamentally the stuff that I think really matters.

edited w Juwon Lee, founder of Chestnut.ai

bart decrem


entrepreneur, at mozilla. + surf & music production.


music production, apps & tech

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