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

`2:30:30`

at 50, 60 people when none of those individuals or none of those roles. It's never about the individuals. It's about the roles. None of those roles are in your organization fulltime. Occasionally you need a manager. Occasionally you need a lawyer. I can play the role of manager occasionally, fine. And then I can…

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`2:31:31`

with your own quirkiness to a degree that isn't actually healthy. And I've certainly done that over time and we should have had someone mount or count the beans a little more diligently, a little earlier. This was part of a blessing of just being wildly profitable and selling software that can have infinite margins…

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`2:32:33`

Can we just linger on that advice that you've given that small teams are better? I think that's really less. Less is more. What did you say before? Worse is better. Okay, I'm sorry. — Worse better on adoption with technology a lot of times. And I think actually comes out at the same thing…

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`2:33:35`

They have so many more resources. They have so many more programmers. What if they take a liking to your little niche here and they show up and they just throw a thousand programmers at the problem? And my answer perhaps partly because I was like 24 was first of all, no, no care in the world…

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`2:34:36`

— Yes. — It's so fascinating and part of it's the manager thing. — Because humans don't scale. Communication between humans certainly don't scale. You basically get the network cost effect every time you add a new node, it goes up exponentially. This is perhaps the key thing of why I get to be so fond…

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`2:35:38`

that emerges from the code, from the product, from the thing you're working on in the moment. You know far more about what the great next step is, when you're one step behind rather than if you try 18 months in advance to map out all the steps. How do we get from here to…

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`2:36:38`

They're buying something because it's good. And the way you get something good is you don't sit around and have a meeting about it. You try stuff. You build stuff. — It really is kind of incredible what one person, honestly one person can do in 100 hours of deep work of focused work, even…

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`2:37:38`

Part of that story is Ruby. Part of that story is Rails. But a lot of it is also just me plus Jason, plus Ryan, plus Matt. That was the entire company at the time. And we could create something of sheer sustaining value with such a tiny team, because we were a tiny team. Not to…

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`2:38:39`

— How do you protect the small team. Basecamp has successfully stayed small. Has been the dragon, and you had to fight off. That like basically you make a lot of money. There's a temptation to grow. So how do you not grow? — Don't take venture capital. — Okay, that's step one. — That is point number…

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`2:39:41`

is to get to a billion dollars or more. Now the path to that usually does go through running established playbooks and then when it comes to software, the enterprise sales playbook is that playbook. If you're doing B2B software SaaS, you will try to find product market fit. And the second you have it, you…

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`2:40:44`

and 100% of the proceeds of that purchase went into my and Jason's bank account, personal bank account. Not a single cent went into the account of the company 'cause we didn't need the money to grow. What we needed or what we certainly enjoyed was to some extent maybe the vote of confidence, but…

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`2:41:45`

I wonder from, I'd love to hear Jeff's side of the story of like why, 'cause he doesn't need like the money. So it's really, I think it probably is just believing in people and wanting to have cool stuff be created in the world and make money off of it, but not…

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`2:42:48`

And his investment team said like, "Jeff, no way. This makes no economic sense at all. They're asking for way too much money with way too little revenue." And Jeff just went like, "I don't care. I wanna invest in this guy." Because to him at the time it was chump change, right? Like Jason…

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`2:43:48`

He gave us the economic confidence, but then he also gave us the confidence of a CEO running perhaps at the time the most important internet business in the US. Showing up to our calls, which we would have with him like once a year and basically just going like, yeah, you guys are doing awesome stuff…

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`2:44:49`

And certainly Amazon had a extremely long-term vision. So far longer than I have ever had the gumption to keep. Like I think of myself as a long-term thinker. I am playing a child's game compared to the game that Jeff is playing. Like when I looked at Amazon's economics around the dot…

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`2:45:51`

This is something about humans that don't appreciate so much that we take for granted the positive that a thing brings real quick and then we just start criticizing the thing. It's the Wi-Fi and the airplanes. — [DHH] That's exactly it. — But I think Amazon, there could be a case made that Amazon…

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`2:46:51`

If you are creating something of value that a lot of people love, you must create an equal and opposite force of haters. You cannot have people who love what you do without also having people who hate what you do. The only escape from that is mediocrity. If you are so boring and so uninteresting that…

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`2:47:52`

creating so many amazing products, not murder each other? It's a great story of like partnership. What can you say about collaboration? What can you say that about Jason that you love that you've learned from? Why does this work? — So first I'll say we have tried to murder each other several times over…

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`2:48:53`

And that we were able to stomach that level of adversity on the merits of an idea because it was about the idea. It wasn't about the person and it never really got personal. Not even never really, it didn't get personal. It wasn't like, Jason, you're an asshole. It was like, Jason…

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`2:49:54`

would see something that looks like I'm going after the man rather than the ball. And I do think I've tried to get better at that. But in my relationship with Jason, I think it's worked so well because we have our own distinct areas of competence where we fully trust each other. Jason…

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