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My First Million

DHH: $100M+ Advice That'll Piss Off Every Business Guru

17 Mar 2026

Transcription

Chapter 1: How can you stand out in a crowded market?

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Are you able to give any ballpark for previous numbers? Let's just say ridiculous. I think that's a good ballpark, right? When you are introducing yourselves, what do you even say? Because you've done so many different things that I don't even know what you take credit for most or what you hang your hat on. Well, it all depends on the audience.

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If I'm talking to a bunch of car nerds, I talk about winning Le Mans. If I talk to a bunch of programmers, it's all about Ruby and Rails.

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Chapter 2: What does it mean to not give a damn in business?

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And if it's a bunch of entrepreneurs, it's usually about building Basecamp and 37signals.

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Chapter 3: What is the difference between liquid and crystallized intelligence?

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Have you ever said Basecamp's revenue? No, we've never disclosed the full revenues nor full profits. I think we've said tens of millions or something.

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Chapter 4: How do constraints breed creativity in business?

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I don't even know. That's one of the great privileges of being a private company. It certainly served us well for many, many years when we had the entire project management space in SaaS to ourselves. And we were laughing all the way to the bank because clearly someone else must have realized this was a highly profitable, not even niche, but category of software.

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And it just took a decade until anyone else woke up to the idea that this could be a good business. And then we had competition.

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Chapter 5: What can we learn from being publicly wrong?

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So very much enjoy the privilege of being a U.S. private company and not having to disclose that goddamn thing. Sam, have you ever been to, if you go to 37signals website, Sam, have you ever clicked at the bottom? There's this little tab that just says 1999. Have you ever seen this? Uh, no, I'm going to do it now.

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Chapter 6: How do taste and data influence business decisions?

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What's it say? It's amazing. So, so in general, I feel like you guys have done an amazing job of like planting your flag in the ground. I'm like, yo, this is what we believe. And rework was a fantastic book. Your website right now is basically kind of like rework. It's just a, 30 chapters of shit we believe, rather than trying to sell you on our software.

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Let me tell you our philosophy as founders and entrepreneurs. But if you click 1999, Sam, what do you see? I see a website, a page that looks sort of like it's from the year 1999, and it's all white, and it says 37 Signals Manifesto, and it's a 37-chapter book in plain text. And there's chapters like chapter 24, my cousin's buddy. And it says, my cousin's buddy is a web designer.

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And then you guys wrote, then let him do it. The money you'll save having your cousin's buddy build your website will be nothing compared to the cost of time and money to undo his mistakes. And so like very much, this is like this blast from the past. You guys have been doing this for like, you know, whatever, 27 years or something of,

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Chapter 7: What is David's perspective on using AI in business?

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saying what you feel unapologetically and having that be something that, like leading with the philosophy rather than leading with like, hey, here's our features and here's our products, please use us. Yeah, so a lot of it is simply based in the fact that neither Jason and I can shut up about what we believe.

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So it is a natural byproduct of us existing and working that we keep coming up with ideas takes on different topics in our industry, how to build a company, how to run a company, how to do technology, how to do design. And it would be an awful waste, in my opinion, if we didn't try to capture some of those observations and lessons and distribute them more broadly.

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But there's certainly also a more... economic side to it. When we got started, I think it's in Rework, there's a chapter about how to out-teach rather than out-spend the competition. And that was really our operating paradigm since the beginning, because we never raised VC. We never had more money than anyone else. We always had to earn the money we wanted to spend first.

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And that meant a whole host of constraints on how we could run our business and certainly how we could run marketing. Because if you don't have a bunch of money to buy ads and awareness that way, you have to earn it. And the way to earn it is simply to be interesting. I don't set out to be interesting as a objective. I try to be ruthlessly honest and very forthright in everything that I learn.

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And that in turn turns out to be interesting to some people some of the time. Because so much of business advice is either being given by people who aren't doing business We're observing and deducing, and there's an entire category of that, usually padded to fit exactly 300 pages. And maybe it has a funny exclamation point in the word **** instead.

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Like, I think that's the most popular genre right now of how to quit my **** job or something. That's what I see at the airports all the time right now. Or it is from entrepreneurs who are active, but very often have all sorts of liabilities in terms of what they can say because they have investors or they're publicly listed or whatever. And basically, Jason or I had none of those constraints.

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We were in the thick of it, are in the thick of it, running our own business, having to make more money than we spend. And also, we don't have any of the constraints.

Chapter 8: What lessons can we learn from taking on big tech companies?

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We don't have anyone... who could tell us no. Now, some days I wish there were people who could tell me no when I tweet out something stupid or write something harebrained, but the net sum, the moving average of that arrangement of doing something

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that is successful enough that people care about what you have to say, and then not having that course filter of, oh, I wonder what my investors are going to think about this, has produced over the last 25 plus years, a steady stream of observations, mission statements,

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crazy attempts to do this, that, or the other thing that very often ended up not being what everyone else was doing, partly because we weren't consuming the same water. Now, neither Jason or I have been In Silicon Valley, we're not products of that.

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However much I have tremendous respect for everything that's come out of that place, it does have a tendency to produce uniform thinking around a whole host of big topics. And 37signals was born in Chicago at a time where that had zero impact. tech community of note. It wasn't until much later and Groupon and all these other things that some life was bred into the Chicago tech scene.

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But when we were coming up, there was no one there. So we just had the luxury of distance to everyone else's echo chamber, which meant that original thought was possible.

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I'm not going to claim that all the original thought was good, but I will claim that if you look back upon some of the things that we wrote now 20 years ago, Getting Real, the first book, that manifesto from 99, Rework from 2010,

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A lot of that stuff still holds up because it's focused on fundamentals and focused on extracting lessons from our work, producing something that was worthwhile and lasted. All right, so this episode is all about excellence.

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A while back, I shared my personal framework for building excellence in my own life, and the team at HubSpot turned it into a 30-day operating system you can check out right now. It breaks down the systems it took me 10 years to figure out and shows how I actually use them day to day. These are systems that genuinely changed my life.

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So if you want to build a good life, scan the QR code or click the link in the description. Now, let's get back to the show. So 20 years ago, you were in your 20s, and I don't know how successful you were. I would imagine mildly successful, but still had a lot to go. And yet you were giving advice.

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