Apple

`3:45:03`

And I continued that work over many years. Jason or I actually in I think 2004, 2005, did an ad for Apple that they posted on the developer side where we were all about like Apple is so integral to everything that we do and we look up to them and we are inspired by them. And that love relationship actually continued for a very long time. I basically just became a Mac person for 20 years. I didn't even care about looking at PCs. It seemed irrelevant to me, whatever Microsoft was doing, which felt like such a relief. Because in the '90s, I felt like I couldn't escape Microsoft and suddenly I had found my escape. And now I was with Apple and it was glorious and they shared so many of my sensibilities and my aesthetics and they kept pushing the envelope, and there was so much to be proud of, so much to look up to. And then that sort of started to change with the iPhone, which is weird because the iPhone is what made modern Apple. It's what I lined up in 2007 together with Jason for five hours to stand in the line

`3:46:07`

to buy a first generation product where Apple staff would clap at you when you walked out the store. I don't know if you remember that. It was a whole ceremony and it was part of that myth and mystique and awe of Apple. So I wasn't in the market for other computers. I wasn't in the market for other computer ideas. I thought perhaps I'd be with the Mac until the end of days. But as Apple discovered the gold mine, it is to operate a toll booth where you don't have to innovate, where you don't actually even have to make anything, where you can just take 30% of other people's business. There was a rot that crept into the foundation of Apple and that started all the way back from the initial launch of the app store. But I don't think we saw at the time, I didn't see at the time just how critical the mobile phone would become to computing in general. I thought when the iPhone came out that like, oh, it's like a mobile phone. I've had a mobile phone since the early '90s.

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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

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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

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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.