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topic: transcript-lex-474-2025 ✕

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DHH2025-07-12transcript-lex-474-2025source ↗context

`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…

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`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…

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`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…

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`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…

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`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…

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`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…

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`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…

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`3:52:16`

So if you wanna give discounts or refunds or whatever, it's complete hell. If you want to easily support multi-platform that's complete hell if someone signs up for HEY on their iPhone and they wanna switch to Android. But that billing relationship, it's tied to Apple, it's complete hell. For a million…

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`3:53:21`

such noise that they will regret it. And that's exactly what then happened. We were blessed by the fact that we launched HEY one week before the WWDC, their Worldwide Developer Conference. Where Apple loves to get up on stage and harp on how much they do for developers, how much they love them and why…

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`3:54:21`

but we had to build some bullshit dummy account such that the app did something when you downloaded it. That was a rule that Phil Schiller seemingly made up on the fly when pressed for the fifth time by the media about why we couldn't be in the app store when a million other companion apps…

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`3:55:24`

Tim recently revealed that it has cost well over a hundred million dollars in legal fees to carry on this battle against Apple. We, for a hot moment, considered suing Apple when they were threatening to kick us out. We shopped the case around with a few law firms and perhaps of course they would tell us…

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`3:56:25`

no board would've signed off on this lawsuit to a professional CEO, no freaking way. So the fact that they've been able to beat Apple in also the most hilarious way possible, I think it's just incredible. 'Cause remember their first victory in the case was actually not much of a victory. There were…

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`3:57:26`

that the rule of law in the US now is that you can launch an app in the app store. And you don't have to use in-app payment, but you can have a direct billing relationship with a customer if you just link out to the open internet when you take the credit card and…

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`3:58:27`

to this day sort of the unreasonableness of principles. Yes, that's what I love. I think sometimes maybe even with founders you can get worn down. It's a large company. There's a lot of smart, quote, unquote, people around you lawyers and just whispering your ear over time and you're like, well just…

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`3:59:29`

after 25 years would come to an end because Apple would burn us down or I would burn the business down over this fight with Apple. But I think you also need that level of conviction to be able to even drive the day-to-day decisions. One of the other Apple examples, and I know we…

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`4:00:31`

you can dilute yourself into thinking that you can dictate all terms at all times and there are no long term consequences. Apple is learning finally, the fact that there are long-term consequences and that developers actually are important to Apple's business. And the relationship is not entirely one sided. We don't owe our…

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`4:01:31`

that I created in the most unreasonable way possible? Couldn't we have found a better way to do this? I think they're going to get forced to do a better way. But did you also have to go through the indignity of having a criminal contempt charge against you getting referred to prosecution? It just…

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`4:02:33`

So like Apple is a truly special company. We mentioned Amazon, there is no company like Apple. — I agree, this is why the disappointment is all greater. Because we had such high aspirations and expectations to Apple that they were the shining city on the hill and they were guiding the industry in a million positive ways…

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`4:03:34`

So they have to wash that off first I think before they find their wear back. But Apple's been in a mirage before, I mean Wozniak and Steve Jobs started this thing in the garage, has great success with the Apple II. He hands the company over to a sugar drink salesman who tanks the company…

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`4:04:35`

or something like that, right? So you can get diluted into thinking that something is forever when you're in the moment. And they seem so large. Apple could absolutely stumble and I think they have more reason to stumble now than ever. They're behind on AI, terribly behind. Their software quality is faltering in a…

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