DHH · 2025-07-12 · source ↗ · whole document (12)
Apple
`3:47:08`
Well, it wasn't a mobile phone. It was a mobile computer. And even more than that, it was the most important computer or it would become the most important computer for most people around the world. Which meant that if you liked to make software and wanted to sell it to people, you had to go through that computer. And if going through that computer meant going through Apple's toll booth and not just having to ask them permission, which in and of itself was just an dignity. When you're used to the internet where you don't have to ask anyone permission about anything, you buy a domain and you launch a business and if customers show up, boom, you're success. And if they don't, well you're a failure. Now suddenly before you could even launch, you'd have to ask Apple for permission. That always sat wrong with me. But it wasn't until we launched HEY in 2001 that I saw the full extent of the rot that has snug into Apple's apple. — For people who don't know and we'll talk about it, HEY is this amazing email
`3:48:09`
sort of attempt to solve the email problem. — Yes, I like to pitch it as what Gmail would've been with 20 years of lessons applied in a way where they could actually ship. Gmail was incredible when it launched in 2004. And it still is a great product but it's also trapped in its initial success. You can't redesign Gmail today, it just has way too many users. So if you want fresh thinking on email, I wanted fresh thinking on email. I needed to build my own email system. And not just my own email client. That's what a lot of people have done over the years. They build a client for Gmail, but you're severely constrained if you don't control the email server as well. If you really wanna move the ball forward with email, you have to control both the server and the client. And that was the audacious mission we set out to do with HEY. And that was what's funny, I thought our main obstacle here would be Gmail. It's the 800 pound gorilla in the email space. Something like 70% of all email in the US
`3:49:11`
is sent through Gmail. I think their world rates are probably in that neighborhood as well. They're just absolutely huge and trying to attack an enormous established competitor like that who's so actually still loved by plenty of people. And is free seems like a suicide mission. And it was only a mission we signed up for because we had grown ambitious enough after making Basecamp for 20 years that we thought we could tackle that problem. So I thought, hey, this is dumb. I would not advise anyone to go head to head with Gmail. That seems like a suicide mission. We're gonna try anyway, because you know what? If we fail it's gonna be fine. We're just gonna build a better email experience for me and Jason and the people at the company and our cat, and that'll be okay 'cause we're gonna afford to do so. But when we got ready to launch, after spending two years building this product, millions of dollars in investment to it. We obviously needed mobile apps.
`3:50:12`
You're not gonna be a serious contender with email if you're not on a mobile phone and you need to be there with a native client. So we had built a great native client for both iOS and for Android. And as we were getting ready to launch, we submitted both of them to the app stores, got both of them approved on I think Friday afternoon for the iOS app. And we then went live on Monday. And we were so excited. Hey world, we've been working on this new thing, I'd love for you to check it out. And of course as with anything, when you launch a new product, there are some bugs. So we quickly found a few in the iOS client and submitted a new build to Apple. Hey, here's our bug faces, can you please update? And that's when on help broke loose. Not only were they not gonna prove our update, they said, oh wait a minute, we gave you permission to be in the app store, but I'm sorry that was a mistake. We see that you're not using our in-app payment system, which means that we don't get 30% of your business. You will have to rectify that
`3:51:14`
or you can't be in the app store. And first I thought like, well it got approved already. We're running on the same model. We've run Basecamp on in the app store for a decade. If you're not signing up through the app and we're signing up our own customers on our own website and they're just going to the app store to download their companion app, we're gonna be fine. That was the truth, right? That was why I never got so fired up about the app store. Even as Apple started tightening the screws was like my business was okay. Now suddenly my business wasn't okay. Apple was willing to destroy HEY if we did not agree to give them 30% of all the signups that came through the iOS app. And it wasn't just about the 30%. It was also about splitting and not longer having a direct relationship with our customers. When you sell an app in the app store, you're not selling an app to a customer. You're selling an app to inventory at Apple, and then Apple sells an app to that customer. That customer has a purchasing relationship with Apple.