DHH on how f*ck you money changed every decision he made.

Sam Parr

"Are you able to give any ballpark for previous numbers?"

MFM

Let's just say *ridiculous*. I think that's a good ballpark, right?</FormattedResponse>

Sam Parr

"When you are *introducing yourselves*, what do you even say? 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*." </FormattedResponse>

MFM

Well, it all depends on the audience. 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 on Rails*. And if it's a bunch of entrepreneurs, it's usually about *building Basecamp and 37signals*. </FormattedResponse>

Sam Parr

So, have you ever said Basecamp's revenue?

MFM

No, we've never disclosed the full revenues nor full profits. I think we've said *tens of millions* or something—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, legally, someone else must have realized this was a highly profitable—not even a niche but a category—of software. 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. So: very much enjoy the privilege of being a U.S. private company and not having to disclose that goddamn thing.

Shaan Puri

Sam, have you ever been to—so, if you go to Thirty Seven Signals' website, Sam, have you ever clicked at the bottom? There's this little tab that just says "**1999**".

MFM

Have you?

Shaan Puri

Ever seen this?

Sam Parr

No. I'm going through it now. What's...?

Shaan Puri

It's amazing. So, in general, I feel like you guys have done an amazing job of planting your flag in the ground—like, *this is what we believe*. *Rework* was a fantastic book. Your website right now is basically kind of like *Rework*: it's just 30 chapters of "shit we believe" rather than trying to sell you on our software. Like, "here, let me tell you our philosophy as founders and entrepreneurs." But if you click 1999, Sam, do you see?

Sam Parr

I see a website — a page that looks sort of like it's from the year 1999. It's all white and it says **"37 Signals Manifesto."** It's a 37‑chapter book in plain text.

Shaan Puri

**Chapter 24 — "My Cousin's Buddy"** "My cousin's buddy is a web designer." And 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." So it's very much this blast from the past. You guys have been doing this for, like, you know, twenty-seven years or something — saying what you feel unapologetically and having that be something that leads with philosophy rather than leading with, "Here are our features and here are our products; please use us."

MFM

Yeah, so a lot of it is simply based on the fact that neither **Jason** nor I can shut up about what we believe. It is a natural byproduct of our existing and working together that we keep coming up with 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. 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. But there's certainly also a more economic side to it. When we got started—I think it's in *Rework* [the book Rework]—there's a chapter about how to "out-teach" rather than "out-spend" the competition. That was really our operating paradigm from 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, and that meant a whole host of constraints on how we could run our business and, certainly, how we could run marketing. If you don't have a bunch of money to buy ads and awareness that way, you have to earn it. The way to earn it is simply to be **interesting**. Now, I don't set out to be interesting as an objective. I try to be **ruthlessly honest** and very forthright in everything that I learn, and that, in turn, turns out to be interesting to some. So much of business advice is either given by people who aren't doing it or by people who are merely observing and deducing. There's an entire category of that—usually padded to fit exactly 300 pages and maybe it has a funny exclamation.

MFM

In the world right now, the most popular genre seems to be *"how to quit my job."* That's what I see at the airports all the time. Sometimes it comes from entrepreneurs who are active, but very often those people have all sorts of liabilities in terms of what they can say — because they have investors, they're publicly listed, or whatever. Jason and I had none of those constraints. We were, and are, in the thick of it: running our own business, having to make more money than we spend. We don't have anyone who can tell us no. Some days I wish there were people who could tell me no — for example, when I tweet something stupid or write something harebrained. But the net result, the moving average of that arrangement — doing something successful enough that people care about what you have to say, and not having that coarse filter of, "Oh, I wonder what my investors are gonna think about this" — has produced, over the last 25+ years, a steady stream of observations, mission statements, and crazy attempts to do this or that. Very often those attempts ended up not being what everyone else was doing, partly because we weren't consuming the same water. Neither Jason nor I have been in Silicon Valley; we're not products of that. I have tremendous respect for everything that's come out of that place, but it does have a tendency to produce uniform thinking around a whole host of big topics. Thirty Seven Signals was born in Chicago at a time when that city had zero tech community of note. It wasn't until much later, with Groupon and other companies, that some life was breathed into the Chicago tech scene. When we were coming up there was no one there, so we had the luxury of distance from everyone else's echo chamber — which meant original thought was possible. I'm not going to claim that all the original thought was good. But I will claim that if you look back at some of the things we wrote twenty years ago — *Getting Real*, the manifesto from 1999, *Rework* from 2010 — a lot of that stuff still holds up because it's focused on fundamentals and on extracting lessons from our work, producing something that was worthwhile and that lasted.

MFM

**Alright, so this episode is all about excellence.** 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, 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.

Sam Parr

So, twenty years ago you were in your twenties, and I don't know how successful you were. I would imagine you were mildly successful but still had a lot to go. And yet you were giving advice. I think a lot of people listening—myself included—when I hear you talk about *teaching versus teaching versus spending* [**unclear phrase**], I think that's great advice. But I'm like, I don't want to give advice when there are so many people who are more successful than me; they should be giving advice. You know, this sort of *imposter syndrome* stuff. How did you justify teaching fundamentals, giving advice, and writing a book on work when you were still in your twenties, and there were probably a thousand people above you who could have said, "What the hell does this guy know?"

MFM

Part of it, I think, is genetics. I've been blessed with a completely irreverent personality that thrives in exactly those kinds of circumstances. I don't give a damn what people think I can and can't say. I'm going to call it like I see it when I see it—whether I'm 19 or 15 or 46 or 37. The other aspect of that is that both Jason and I spent quite a long time working for other people. Not a lifetime in the grand scheme of things, but I've been working since I was 15—well, even earlier than that—but I've had a boss since I was 15. By the time I was 26, I'd been in business to whatever degree that is, either as an employee or running myself, for a decade. I don't even think you need that. What you need is exposure to novel terrain with enough influences and being informed somewhat of what other people think. Then your token generation machine will start producing if you are of the kind of constitution that I am. One of the ways I try to internalize the best lessons from what I'm going through is to share. There's the old adage that nothing makes you learn a subject better than trying to teach it. It's very much true when it comes to this. There's also a great paradigm of **liquid versus crystallized intelligence**. If you look at Nobel Prize winners in physics, chemistry, math, and so on, they all do their formative work in their twenties. Then there's a decade of application in their thirties, and they often get the Nobel Prize in their forties for the work they did in their twenties. Part of that is just biology. I remember when Mark Zuckerberg said something in February that was hugely controversial. He said something to the effect of, "young people are just smarter," and everyone was like, "You can't say that, that's wrong." Well, it's not wrong in a certain category of intelligence—this form of liquid intelligence: smart, fast synapses firing. Young people are smarter in that way, just like they run faster. You don't see a lot of 42-year-old 100-meter sprinters; that's not part of human performance. You get the payoff when you get older, because you have more crystallized intelligence and can make more connections. If you look at Nobel Prize winners in history, I think the average age is, like, 80—those connections come later. I have tremendous respect for that crystallized intelligence. I also respect liquid intelligence: it's both very smart and very quick, and also totally ignorant. It has no sense of the broader world, no sense of what you're allowed to do or not allowed to do, and no sense that someone who knows more means you should shut up. I look back on that time and feel so glad I embraced all that ignorance with the hubris of 20. That's how we change the world in a very literal sense—new ideas very often come from that vector.

Shaan Puri

No, nobody loves a cautious 20-year-old. The **co-founder of HubSpot** came on this podcast. He talked about how, in his first company, he was making everything up. In his second company he thought, "Oh, now I know how I'm going to do everything differently," and it totally failed. He said, "Just because I was ignorant doesn't mean I was wrong." There's something to that idea — you can be both ignorant and correct. </FormattedResponse>

MFM

I'd go so far as to say that **ignorance is a benefit** for a huge class of problems. You are cursed when you've been through the loop once. When you know too much, you cannot *unsee* in the same way. You will be locked into paradigms and thought patterns. If you want to break those paradigms—if you want to break those thought patterns—you kind of have to start from a clean slate. Now, that's not universally true in all cases, but I do think it describes the case that Jason and I went through. We had some input which was working for other people, working at a crazy time in our industry—maybe the second-craziest time next to right now, which was the dot-com boom and bust. Both of us went through it, both on the way up and on the way down, and saw all the dynamics play out. If you compress those years from, let's say, 1997 to 2001—like, that's only four years—that was instruction worth a decade, at least maybe two, because there was just so much happening. You got all the explosion of "here's the internet, what are we gonna do with it?" You built wild castles in the sky that came tumbling down in 2001 as the dot-com boom burst. So we had all those inputs—those experiences—and then we kind of started in the desert when Jason and I got going with Basecamp. This is back in 2003. We started working on it when it was still a wasteland. The dot-com bust had exploded everything. You had programmers going back to being chefs or gardeners or whatever. There was simply no work to be had because the whole industry blew itself up. In that wasteland we just went, "Oh—do you know what? We now have to be scrappy. We now have to rely on ourselves. We have to be tremendously productive because we can't hire a team of 50. We can't buy tons of servers. We have to use open source because we can't afford licenses for Oracle databases." All of those constraints applied to our situation and then produced an explosion of creativity, because that's what very often happens when you are deprived in all the right ways. You will find out, "Oh, there's a better way to do this." You will find out the optimizations. A parallel to today is the big scary moment for the US AI industry when DeepSeek put out R1. Some of this is mythology, some of it is bullshit, but the storyline at the time was they could not buy NVIDIA CPUs due to export restraints. They trained the whole thing on 5,000,000. I know there's reservations and asterisks behind that, but the fundamental principle was they came up with some novel new techniques of using vastly less compute to still get quite far. I think that applies very much to our situation at the time. We just didn't have millions of dollars. We had a consulting business that we had to make pay for all these experiences we wanted to do, and therefore we just had to be radically more productive. On the technical side, this was the birth of *Ruby on Rails* for me. I could not use the same technology everyone else was using because I had a tenth, a hundredth, a thousandth of the capacity. Therefore I had to use something else. I had to use something, or come up with something, that allowed me as an individual programmer and technical person in the whole operation to build Basecamp by myself on the technical side. I am forever grateful that these were the constraints we were under. If we had raised, I don't know, $20,000,000 and hired a hundred people, we would just do the same stuff as everyone else and we would never have come up with Ruby on Rails.

Sam Parr

Do you guys want to hear a *crazy stat*? Nobel Prize–winning scientists are **22 to 25 times more likely** to be in some type of performing class—so acting, magicians, singing—or some type of art, like drawing, or whatever.

MFM

Is that right?

Sam Parr

**"22 times more likely."** I read about that in Bill Gurley's book, and then I looked it up — it's a study. The reason I'm bringing this up is I've been obsessed with that fact; it just seems astronomical. Then you brought up the idea of *crystallized versus liquid knowledge*, and it just solidifies that. It kinda adds to it. Ain't that a crazy stat?

MFM

That is wild. Do you know what's funny? We all read whatever we want into factoids like that. But when I was a kid, what I really enjoyed being was the **Dungeon Master**. I played **Dungeons & Dragons** and other role-playing games. Most people just want to be a character; I wanted to run the world. So I think there were some early indicators that I like to *world-build*. Also in games, my favorite game of all time is *Civilization I* — the original Sid Meier game — which is obviously about world-building. So some of those things were present early on. Having positive experience building and bootstrapping with others — having to convince people, before you even have money to pay them salaries, that they should go in your direction, that we should work on this thing together, that you should come into my dungeon — is, I think, exceptionally good preparation for running communities, running open source, and running a company.

Shaan Puri

You know who else's favorite game was *Civilization*? **Mark Zuckerberg**. You know who else—oh no way—both of them have talked a lot about playing *Civilization* early on. I feel like they almost had to stop talking about it for a while when the PR got kind of bad. It's like they wanted to play god a little bit, but now it's cool again. Speaking of **Facebook** and **Zuckerberg**, you got a lot of things right. I think you were really early to remote work as a concept. Being profitable as a strategy was somehow contrarian at the time, but obviously important. One thing you famously got wrong was you wrote a post called "Facebook Is Not Worth $33 billion" (you wrote this great post in 2010). I think Facebook had probably just gone public or was close to it, and you basically said Facebook's a great success—500 million people use it—but it's not worth $33 billion. You laid out the case as to why that was not true. Now, looking back on this, do you just look at that as "I got it wrong," or do you think the kernel of what you were saying was right? How do you think about this blog post now?

MFM

I love that blog post. It's funny because people often pull it forward to *dunk*. They say things like, "Hey—look, seventeen years ago you got a thing wrong."

Sam Parr

And.

MFM

What I love even more is it's often because, right? You're like, "Hey, wait a minute — isn't your business to be wrong nine out of ten times? Wasn't your last fund just wrong on the vast majority of the investments that you made?" Oh, okay. Well, let's start from that premise. But I don't even care. I love that article because it's both a good example of being wrong and accepting that in terms of outcomes, yet trying to draw better conclusions than just, "I got it wrong at the gambling table." Like, "I should have bet on Facebook — if I had bought the stock at that time rather than say they weren't worth it, I would have made so much money." A great term that I learned from this poker book is called *resulting*. In poker there's this concept: you analyze — well, not just analyze — you consider the odds given the cards that you have and the cards on the table. What are the odds that you're going to make whatever hand you're trying to make? If you delude yourself into thinking, "I should keep playing 16% hands; I should just go all in on 16% because, do you know what, I won the last three," you're a fucking idiot and you're going to lose all your money. That's not how to win in poker. The way to win in poker is to make sure you predominantly play hands that have the best odds. Conversely, if you go all in on a hand that has an 87% chance of success and you lose, you're an idiot if you draw the conclusion that you shouldn't have gone in on that hand. You totally should have gone in on that hand. So *resulting* is evaluating your decision on the basis of the outcome alone. Now, obviously you can't fully divorce those two things, but you have to evaluate on a longer trend line. Everyone is going to miss a shot — not just one shot. They're going to miss a hundred shots, a thousand shots, a million shots over the course of their careers. In fact, this is why the VC parallel is so important. VCs have gotten tremendously rich being right 10% of the time. I mean, isn't that — I mean, that's an incredible stat: you're able to build such wealth by being so wrong so often. But let's even dig into the merits, because I love that case too. When I did that analysis on Facebook, they did not have a monetization strategy. What they had was a lot of traffic. I paired, or pattern-matched, that traffic on — I don't know if this is too far — but there was something called Blue Mountain, I think back in...

Shaan Puri

2,000 website.

MFM

Yes. They were tremendously popular at the time and had a ton of traffic. Right now, all that traffic was ruined because they did not have a mechanism for turning that traffic into gold. It was just trash — *trash traffic*. It was just people who wanted an e‑card. What are you going to do with that? Maybe today you could make it work, but they certainly couldn't at the time. My analysis was: **Facebook is trash traffic**. It's just a bunch of people talking about all sorts of stuff that isn't *intentional* in the way a Google search, for example, is. At the time, the **surveillance capitalism** paradigm was probably already well under construction but not widely distributed. This was the *alchemy* that was going to turn absolute trash traffic into gold. Surveillance capital flipped it on its head: it did not matter whether intent was there. If we know everything about everyone at all times, all that matters is eyeball time. Now we can pinpoint whether something should be shown or not on the basis of who they are, not what they're talking about. They could be talking about the most deranged, stupid stuff and we could still make better ads happen because we can target those individuals better than a golf magazine online can target with golf ads. I don't know if that person currently has buyer's intent for a new set of clubs, but Facebook probably knows whether you're within ten miles of the golf store right now, whether you're driving toward it, and whether you could be swayed one way or the other. I didn't see that. I did not realize the power of that alchemy. By the way, nobody else did either — because if they did they would have said, "Holy shit, Facebook has invented alchemy. Why are they only worth $33,000,000,000? They should be worth half of $1,000,000,000,000. Let's just go all in, bet the house." No one did that. Anyway, I love it for all these things. I love it for the resulting effects. I love it for this example of alchemy: when someone really figures out a complete unlock on the entire internet business at that right moment, when they also have all this trash traffic that would otherwise have been worthless. And I just love being able to say, "Do you know what? I was wrong." I remind myself of that at least yearly, sometimes more often—especially when some VC wants to dunk and pulls out a sixteen‑year‑old blog post. Sit back and smile. Yes, you should have some humility about your predictions. </FormattedResponse>

Sam Parr

Can I tell you guys about a funny interaction I had with your business partner, **Jason**? So **hey.com** — if you guys are listening, go to hey.com. That's one of my favorite landing pages. You guys are wonderful at writing copy; you're obviously great at design, but copy is the *forgotten* skill set in internet... internetting is sort of a lost art. You guys have not lost it. You and Jason both have it. I texted him and said: > "Hey, I'm working on a new landing page for my thing and I'm using hey.com as inspiration. What's the conversion rate of your landing page? Because it looks great, it sounds great — is it effective?" He replied: > "You know what, I haven't really looked at it." I was like, "What do you mean you don't look at the conversion rate? You don't know if it's working?" He said, "No, I've never really thought about it. I just know that it felt good and I think it's good, therefore we just ran with it." I was in awe of that reply. It was the opposite of what I would have expected. Can you talk a little bit about the tension between good taste — which I think you have — and also following data? Because you have bills to pay, outcomes you want to achieve, and you want to be great. You race race cars — data matters, like the weight of your car. I don't know anything about racing; precision matters, data matters, and yet you seem to be a follower of *taste first*.

MFM

**This is the luxury of margins.** We have had the luxury of margins since day one because we built something people liked, and we did not balloon the company to chase that interest. We grew the company as we needed—exactly to the point where we were not *deadly frustrated* by our lack of progress on the ideas we had. That meant that, right from the early days and through some periods, we had ridiculous margins. I mean, truly. When I was telling others about our margins in confidence, they were like, "No, no, no—you've got to mean gross." And I said, "No, that's net." They responded, "What do you mean? I've never heard of a business like that."

Sam Parr

Are you able to give any frame or any ballpark for previous numbers, if you're comfortable, just so we understand? Not...

MFM

Really. I mean, let's just say—ridiculous. I think that's a good ballpark, right? Certainly, if you compare to any of the public SaaS companies... we're in a different industry, right? Industries have a tendency to coalesce around a certain profit margin, and it seems like public-market SaaS has coalesced around, I don't know, 10% or something... 20%—ridiculously long stretches of unprofitable growth. Partly that's because there are all these other hacks for how you get money out of the business while leaving nothing for the shareholders, like stock-based compensation and so forth. But that's a different discussion. Our focus from the beginning was: the more margin we have, the more freedom we have. The more freedom we have, the more we can just focus our time on what we like to do. It just so happens to be the thing that Jason and I love—running minutiae A/B tests to squeeze out 0.01. That's very often what's needed. If you want to tweak something, you run a thousand of these experiments, not two. You just stick to it and keep grinding away. And I think *grind* is actually a good word here, because this is something I often hear entrepreneurs say with such pride in their voice: "I grind—this is why I'm working 100 hours a week or 120 hours a week; I'm just grinding, grinding, grinding." I'm like, okay—I don't want to do that. My life is far too interesting to waste it grinding. Grinding is the stupid shit you do in World of Warcraft when you're a peon. No thank you. I don't want to do that. So can we just get to a place where our intuition affords us the success of our intuition—affords us the ability to just do whatever the hell we want, whenever the hell we want? That'd be a great place to be. We arrived at that place very early on in the life cycle of the company. But I will also say, what's interesting about this is that I like numbers. I actually like statistical analysis; I like rigor; I like the confidence intervals—not to the...

MFM

I wanted to run these A/B tests myself, but I have great respect for the statistical tradition. For many years we essentially had a data scientist on staff—someone who would crunch those numbers, do those reports, and try to eke it out. After trying that for over a decade, Jason and I finally came to the honest conclusion that we never did what the numbers told us to do. What we would do was whatever the hell we wanted to do. If the numbers supported that, we'd say, "Those are good numbers." If the numbers didn't support it, we'd say, "Yeah, I don't know—there's probably some factor you haven't calculated." At the end we asked ourselves, why are we doing this? Partly we were doing it because we listened a little too much to other people telling us, "This is how you're supposed to do things." Now, I am not saying this doesn't work for some definition of "work." I'm saying we didn't need it, and that is a much nicer place to be. If you are able to get there, you should embrace it with full gusto. If you have the margin to avoid wasting the precious hours you have on this earth doing stuff that would bore you mindless—don't. We never had the obligation to squeeze the lemon for its last drop. We never had investors going, "Hey, why is this quarter 14.79%? You promised me 16.25—go get the last two percentage points for me." We never had that pressure, and therefore we got to act reckless—in some definition of prudent business operations. I'm immensely proud of that recklessness. First of all, we have outlasted about seven generations of competitors and others in the **SaaS** space who did all of that right: who did all the statistical analysis, who squeezed the lemon all the way, who debased their copy because for a hot second it converted slightly better. We didn't, and we're still around. So part of what I take away from that is: (a) what a nice run, and (b) maybe all the statistical analysis is a bit of hocus-pocus. I don't say that because the numbers aren't right or because the math doesn't work, but because very often the missing ingredients to getting to the **capital‑T truth** are unknown. When you keep drilling down on a set of data that is highly limited and does not describe the world as it exists, you're going to steer yourself blind. You're going to think you found the truth, but you're not hearing from all the customers who aren't signing up. You're not hearing from the word‑of‑mouth that takes 18 months to materialize, because those things can't get computed.

Sam Parr

"But isn't that an absolute? I think your way works wonderfully, and I identify with it — I want to copy you. But you're on the board of *Shopify*. They probably break so many dogmas or rules that you believe in, and it's worked out really well."

MFM

Totally. This is the great thing: Siszek — is this Polish or Czech? I think a philosopher has this great monologue about how he *"hates wisdom."* I'm like, how can anyone hate wisdom? The reason he says that is: for every wise axiom you can find another that says the opposite that also sounds wise. Both of them were extracted from moments of success for that individual in those circumstances. That's a bit of a deflating thing, because it can very easily sort of descend into, "nothing matters, nothing is true, and everything is just postmodern." I don't believe those things at all, but I do believe that **wisdom is very contextual**. This goes all the way back to Newton and Einstein and the theory of relativity. When you go fast enough, all the neat physics rules that are really helpful for calculating the apple dropping on your head just start breaking, and suddenly time and space and everything is relative. So you've got to know your universe. You've got to focus on your set of circumstances and what works in your context. What works for a startup and a small company selling to other small companies is not going to be the same as what works for a Shopify.

Shaan Puri

"What — what's the most interesting thing you've learned from being in the **Shopify** business, **Toby**? If I just asked: what are the biggest lessons or takeaways — that come from letting a smart person go experience a new, novel environment? I'm always curious: what's one or two things that stand out to you?"

MFM

Good question. Some of it is just awe. Like, **Shopify** last year grew almost **30% year-over-year**. I would have been happy to go 30% year-over-year. Very early on in our life cycle they're doing it from a base that's just unfathomable. The law of big numbers gets kinda wacky, right? When you're already doing billions and billions and you're growing at that rate, it feels like you found a glitch in the matrix somehow. What I love even more about it is you can come up with all sorts of reasons for why that is. But, you know, even at the board—**even Tobi**—we don't really know. Like, why did it take Shopify, what, **22 years**, to get to this moment where it just had its best year since the craziest of the peak COVID years? Isn't that fascinating? In many ways the company is doing what it's done since Tobi created **Snowdevil**: "I just want a toolkit for me to create a great-looking store rather than be in the bazaar of Amazon." A simple mission, and they've just been chipping away at that for **20+ years**. Suddenly the charts just go—don't, don't, don't—and all these theories are just that: we don't actually know. The amount of stuff that people don't know is amazing. I mean, I wrote a blog post a while back basically putting that to the...

MFM

Of **"nobody knows anything,"** and I think that's a good general take on the big questions. Nobody knows anything whether we're talking about climate change, what **AI** is going to look like in two years, or why **Shopify** was able to grow 30% year over year in 2022. No one knows anything. We can have all these theories, but very, very little of it gets reduced to irrefutable proof in the sense of a math equation.

Sam Parr

We could talk about this Board of Directors of **Shopify** forever—it's so fascinating. On Toby's bio for the board of directors, the last sentence says that he was on the core team for **Ruby on Rails**, so I assume you've known him for close to 25 years. Are there any cool stories you've had about him, or leadership lessons we can learn? It's very rare—he's built the 17th largest company in the world, and it's also rare that he's been at the helm the whole time. Is there anything interesting about the evolution from a computer nerd to being a proper CEO of a 10,000-person company? Is there anything cool that you or I can learn about that?

MFM

What's funny to me is that you posit that as he went from one form to another form—not true at all. He's still a *computer nerd*. Absolutely. As much as I'm a computer nerd; actually, he's more of a computer nerd than I am most days. The direction of travel—him sending me cool tech stuff and me sending him cool tech stuff—I think it's in **Toby**'s favor, so he's still that person. Now, obviously, he is also the head of this giant corporation that is responsible for, I think I saw something like **15%** of world e‑commerce—a notable share of world GDP. I mean, that's mind‑blowing in a way that I'm really happy that **Toby**, at least, doesn't give any appearance of having internalized that into his character composition. He's very much still the *computer nerd*. I think this current phase that we're in with **AI** and the agent explosion [AI agents] just demonstrates that to a tee. He was incredibly early on this stuff. Some of the public memos that are out from **Shopify**—you can check their dates and then you can check **Toby**'s predictions—and I just gotta give immense respect to that, because I was not that early. In fact, **Toby** helped drag me into the light on some of this, and some of it was also just that I had to see with my own eyes the agents do what they're now capable of doing before I fully flipped on it. But he was just really early on it, and so much of that came from that nerd perspective.

Sam Parr

Mostly, we've had a lot of really amazing people on here. The *ballers*—like Dharmesh from HubSpot—will reference Toby as, "he's the guy who does that": someone able to see a little bit into the future and behave in such a way that he's often just right.

MFM

Totally. I mean, some of it is because he's really smart; some of it is because he's got that nerdy conviction I think similar to what I have. I'd like to believe that we're similar in many ways — that's why we get on so well. We've known each other for twenty-plus years. Is that a little bit of isolation? Maybe. Because of that nerd upbringing: the whole world telling you X and you actually go, "let me just check under the cover" — oh, do you know what it says? Y. I'm going to bet on Y even if the whole world is in on X. To see that continuity, I should say, is incredibly rare. I think part of that is the answer to *why now with **Shopify***. Do you know what? *Compounding determinism* over twenty-some-plus years has a tendency to add up, and it adds up in irregular ways where it sometimes takes quite a long time before the inflection comes. I mean, we say this, but **Shopify** went public — over a decade ago — at a $1 billion valuation. That's a Hall of Fame early investment you could have made, because Shopify didn't do what so many other companies do now, which is essentially reserve all the upside to insiders and their VCs and then go public when it's already kind of plateaued. From where they were to where they are now, it's been an amazing ride for the public investor if they were along for it. But yeah — tremendous respect. It's funny, because I just joined the board a year and a half ago, and it came out of a conversation where I was making the argument to **Tobi** that boards are bullshit and that all the boards I've ever been on were boring snooze-fests, dealing with minutiae to rubber-stamp things for auditors and whatnot. He was like, "I don't know — I think we have a pretty good board." I was like, "Okay." We started talking, and then we had talked for a few hours — five — and then suddenly I came to a realization: do you know what? Yeah, I probably had just been bored because I'd been dealing with things at a scale too similar to my own, and I wasn't learning anything. **Shopify** is dealing at a universe apart in terms of scale while still using some of the same things that I'm passionate about. Shopify is the biggest **Ruby on Rails** shop in the world. Obviously I'm very passionate about that. Many of the other aspects of it have great overlap, but I don't know that scale. I'm like, "That sounds like a fun challenge — let's just do it." And, of course, Tobi's right: is there bullshit on the board of that scale? Of course there is. But it's actually a small minority, and most of it is just really interesting stuff dealing with problems I would never see day to day in my own business.

Shaan Puri

"You mentioned, with AI, you're like, *Toby* kinda dragged me into it a little bit. What's been your evolution with AI? So, a couple years ago, what was your opinion? What were you playing with? And then now, what do you see?"

MFM

I thought it was amazing since day one and I've been a fat GPT user since the first days of that interface. I just loved that we were able to make computers do this right from the get-go. I really like computers — I like them for their own sake, not even always for productive purposes. Some of my favorite time is just sitting in front of the computer doing computer stuff, learning computer things, even if it's not directional toward a specific goal. Even from the beginning, when ChatGPT was "dumb as rugs" and couldn't count the R's in "strawberries" — which is fascinating — I still didn't get it. Now I look into a lot of it: how transformers work, temperature, all of it. I still don't fully get it. Yes, I know "next token," but how does it turn into this? How does it cosplay so well as an intelligent being? Maybe the reason I'm surprised is because I have the wrong model of human consciousness. Maybe human consciousness is far closer to token prediction than any of us would have cared to admit or even investigate seriously before. The models as we have them, as they came to be, work quite close to that, and we have discovered intelligence in some sense. But the timeline is still: from the get-go, awesome — love it. It's not changing my day job. The reason I say that is I'm very particular about how code looks and what it feels like. I was about to say correctness — that's not even the top part of it. I'll get to correctness when I love the aesthetics. On aesthetics alone, the models were just not that good for a really long time. The other part of it was the early AI — not even agents, because they weren't agents; they weren't doing tools. The early LLMs, the early AI, were autocomplete. You're in your editor and then it tries to complete the rest of it. I hated that: it was like having someone interrupt my train of thought every five seconds to usually be wrong. And I mean "wrong" not in the sense of whether the program executes, but wrong in the sense of, "This is not the code I want to write, and I don't like what you're producing." I didn't like that form of using AI and therefore didn't really use it that much for quite a long time. I used it as a pair programmer, as a better Google, as a better Stack Overflow: "Here I have a problem, can you have a look at it?" You taught me what the solution was, and then I would go off and write it.

Sam Parr

And.

MFM

This takes us all the way up to the interview I did with **Lex Fridman** in the summer of last year, where I was essentially giving this spiel. I was saying things like: "I don't like what it produces. I'm extremely impressed. You'd be a fool not to take this super seriously and see it as a directional path for where we're going, but it's not in my business yet." I even — I think in early December — did another interview; I had some revisions on it. From there, it felt like those realms could have been a decade apart. The models that dropped in late November — I think **Opus 4/5** was November 27 or something — that class of intelligence suddenly switched from "I don't like what it's making" to "holy shit… what? How? Okay, I'm gonna merge." The last three months, I'd say, have been the most churn in my mental approach to computers in the entire time I've been using them. More deep questions and more workflow changes have entered my personal life — my day-to-day life, my eight hours in front of that little screen — than at any time before that. And now I'm probably and *thoroughly pilled*. I don't necessarily say that lightly, because that also means I'm actually now in the herd. The herd — certainly out of Silicon Valley — is like **"AGI is imminent,"** and even between now and AGI we're going to go through such an intelligence explosion that… hold on to sucks, right. Yeah — I'm actually now in the consensus on that, which I'm always a little skeptical about. I always want to try to look for the other angle, but it's just undeniable at some… [sentence trails off].

MFM

You just gotta admit the math, and that the agents are **incredibly capable programmers**. I thought, when I talked to Lex last summer, that it was going to turn everyone into a project manager of the old type — the kind of project manager who's not really doing the work, just telling other people what to do. But that isn't true at all. It's more like I've grown **18 arms** and **seven more brains**: I'm operating **22 screens** and I'm still doing all of it, even if I'm not typing every character myself. My progress, when the stars are just right, is **unbelievable** — and **incredibly addictive**. In some sense, that's a little bit like that Facebook thing. You know what? I was wrong about how quickly this was going to radically change everything. I thought it was going to happen, and that we'd have a few years, right? Then suddenly, from December onward, we live in a completely different world.

Sam Parr

I have to thank you for that **Lex Fridman** podcast — a great podcast, six hours long. But I bought three ads with Lex Fridman, the ad for my company **Hampton**. The first ad went on during, like, an Iran war segment, and I was like... </FormattedResponse>

MFM

That was not my target audience.

Sam Parr

"That's not going to work. The second one was like a Jeffrey Epstein video, or... I don't know — it was like *'sub'*. And then the third one was you, and I was like, 'Yes.'"

MFM

Got it.

Sam Parr

"And so, your episode actually made our ad **profitable**. Thank you."

MFM

For that, we go. </FormattedResponse>

Sam Parr

Are you—you know, I read your work. I've read your books; I think they're great. I copy a lot of your stuff. I'm inspired by your stuff because I want to build a company like you. What about what you guys have built today do you think is foolish? Or, what have you built over the last twenty years that a lot of entrepreneurs and business owners admire, but you think is silly to replicate today? What would you advise someone who has, like, a $2–$3 million company and wants to be a bootstrapped $50 million‑a‑year company—or whatever you guys are—and be as profitable as you are and have this life? **Don't actually copy what you see now, because that won't work today.**

MFM

I don't have a straight answer to that. Partly it's because I can see some of the things we've historically been doing work less well than they had. Some of it is exactly this: being able to generate attention is not as transferable to business outcomes as it used to be. There's a great book by Gary V. called *Jab, Jab, Jab, Right Hook*. I love the book and the concept. The basic idea is: "give, give, give—jab, jab, jab a hundred times; just give, be kind, go out there, share all the stuff; and then occasionally you give a right hook: a call to action—'buy my stuff.'" The point is that those occasional right hooks are what pays for the a hundred jabs, because occasionally a right hook lands. What I've seen—and some of it is just a reflection of the dynamics of social media—is that the right hook doesn't travel anymore. All the main social media outlets—X in particular [X, formerly Twitter], where both Jason and I are strong—the algorithm is just never going to show you stuff. It used to be that having a ton of followers meant that a ton of people just saw your stuff. Now the great irony is that this is what people complained about on Facebook back in, like, 2012: "I have all these followers but I can't reach them unless I buy ads." Yeah—that's the demise.

Sam Parr

Of BuzzFeed and all these huge companies. Exactly—the deep...</FormattedResponse>

MFM

That's not actually quite what's happening now. From what I can tell, ads on **X** [the platform formerly known as Twitter] still don't really work. We tried them a bit — maybe they work better now — but they never worked for us. What works is **"viral"**: sharing really interesting stuff. I don't mean "viral" in a negative connotation. It can be positive — you share something novel with people who are interested, and they engage with it. But the trickle-down has kind of stopped. That trickle-down used to look like this: I share a lot of interesting stuff on a daily basis, and then occasionally I ask you to check out my new product. That pathway to "check out my new product" stopped working. So I'm not sure our historic, long-run strategy of *build a large audience and then good things will happen* is necessarily true anymore. I think there's still something to it, but is it viable as your sole strategy if you're someone new? I don't think it converts or works as well as it once did. That's the thing that doesn't work now. I still wouldn't discourage sharing. For your own edification, you should try to share interesting things. That's actually how you learn more: when you try to teach what you've internalized, it sinks in deeper. I also think it's good to share for the sake of sharing, regardless of the outcomes. But I can also see what happens to people who share, share, share and never see anything back — the odds of that person ending up bitter are pretty high.

Shaan Puri

One of the things that both Sam and I love is anybody who *plays their own game by their own rules*. I think whenever we had Jason on—or you on—that's one of the things we like and respect the most. In fact, I almost joined 37signals when I was very young. I was applying to two jobs: one was in San Francisco, in the tech world, and the other was going to be with Thirty Seven Signals. "Oh really?" I went to San Francisco instead.

Sam Parr

But did you get the interview, Sean?

Shaan Puri

I did get the *interview*, but I got the other job first, so I never even took it — I never even... [sentence trails off]

Sam Parr

Went with that. That's awesome.</FormattedResponse>

Shaan Puri

But it was a company I was studying. It was like, if I'm going to join one company, I like these guys. I like how they roll. I like that they have their own drumbeat. You guys have, for a long time, just done things your way. I think, for you, you're kind of an *engineering hero* for a lot of people. Sam and I are not developers, but a lot of developers respect you because you have a strong opinion in the way you roll technically. I think there's the **37signals** part of things, and then there's the outside-of-it part — like doing the races and just living life a certain way. We talked to Jason about his houses and how he's a craftsman, that he has taste and things like that. I'm curious who kind of inspired you. Who are people that you liked something in their blueprint — either how they ran their company, or how they had these side quests outside of their work that was cool and maybe made you want to do the races and dedicate yourself in that sense? Is there anybody you've looked up to, that you've stolen a little bit from their blueprints?

MFM

Completely. I mean, in fact, my entire early career was just finding people who I really liked and looked up to and saying, "I'm just gonna copy the motions." I didn't even know if I fully understood it, but if I just moved my hands the same way and danced the same dance, maybe I'd get a little bit of that magic. One of the ones I think of — maybe Jason aside as well — is **Ricardo Semler**, who wrote a book called *Maverick*. I think it was published in the nineties. </FormattedResponse>

Sam Parr

Oh — with the Brazilian guy.

MFM

Yes.

Sam Parr

I've seen that *book title*. Can you tell us about it? I know a couple, yeah.</FormattedResponse>

Shaan Puri

What's his story?

MFM

Amazing book, amazing story. Ricardo Semler — I think he inherits or takes over this huge industrial Brazilian company that makes pumps for, I think, oil tankers or something. It's the last company you'd imagine being innovative in work practices, and yet he approaches the company with an irreverence to how things are done that would make both Jason and me blush. We try to be relatively radical in what we prescribe, but he really gave us — he certainly gave me — permission to think very differently about how to do things. One example I remember is how he looks at employees and the value they bring over a much longer period of time. He gives the example of this one guy who, almost every week, sits at his desk with a newspaper open and does nothing. You're like, "Why would you pay a guy to sit at his desk and read a newspaper?" Well, it just so happens that occasionally some of these pumps fail in really spectacular ways in far-flung places, and he's the guy who has the capacity to get some oil tanker out of a predicament immediately. One of those rescues will pay for his salary seven times over. I love that anecdote because it's something I've struggled to implement at Thirty Seven Signals [37signals], which is the best kind — right? I've been practicing this for literally two decades: divorcing this sense of *Protestant work ethic* — the idea that if your hands aren't moving for forty hours a week you're not working. That's not the value this individual brings to the corporation. I love that Semler has a million suggestions on how to run a company. We took a fair bit of inspiration from him for both Getting Real and Rework — not quite in the same form he uses; he tells more of a story, a narrative, which is great. Huge fan of him. Another one is Kent Beck. Kent Beck is the author of *Extreme Programming*, one of the heretical software methodologies back in the nineties when everyone was stuck on Rational or the waterfall method, or doing big upfront designs — large manuals before you write a piece of code. Kent Beck was one of the absolute pioneers of a completely different way of working: the agile way. Now that word has stopped meaning almost anything because today it just means "software development." No one is going to tell you they're not agile, except for the really edgy people who've now started to turn away from agile, which is fun to watch. The mainstream adoption of agile didn't happen in '99 or the early 2000s. I saw Kent Beck on stage in 2001 at a Danish conference; he had complete and utter command of the room as he delivered his sermon on software methodology, and I was just in awe.

Shaan Puri

By the way, his LinkedIn—his LinkedIn is hilarious. His bio says: "Of the handful of people who have shaped how we build software, Kent is the **raised middle finger**."

Sam Parr

And he's giving a [unclear: "kent"], it looks like. It looks like he's giving a university graduation speech, and he's wearing a tie-dyed Oxford button-down shirt.

MFM

Amazing. I love **Kent** and everything he's contributed to software development, both in terms of his methodology and his craft. My favorite book on the nitty-gritties of programming is a small book he wrote in the 1990s called *Small Talk Best Practices*. It's quite short, and it is the most influential book on how I write software that I've ever read. Now, it's funny: I've mentioned this book many times over my career, and at one point it was not available as an e‑book—you could only find the print versions. I managed to create so much demand that, I think at one point, a print edition went for $4,500. Now it is available online; you can just buy the PDF. It still totally holds up in this day and age, even though most people are not programming in Smalltalk. Smalltalk is incredible, and Kent wrote not just that craftsman's book about craftsmanship but also reshaped how software methodology is done. Finally, I'd say **Mats**, who created **Ruby** back in the 1990s, opened my eyes to rearranging the priority list. When I got into programming, most programming languages were sold on things like "I'm the fastest," "I'm the most correct," "I have the least memory usage," "I'm the most like C," "I'm the most safe"—all those adjectives. I was like, "Yeah, yeah, makes sense. I should pick the fastest, the one with the least amount of errors." Then Mats comes in and says, "No—Ruby is designed to make the programmer feel good." Like, what? What did you just say—it's about *programmer happiness*? What hippie-dippie bullshit is this? How are we going to create correct programs that make us lots of money if we're focused on programmer happiness? That was a real mind-blown explosion, and it was also the inflection.

MFM

Of my professional career as a programmer, I'd been using a bunch of other tools before—looking at what's most efficient and how to get the fastest. Then, suddenly, I discovered **Ruby** and realized that writing it can be an intensely satisfying experience: making it beautiful. We talked a little bit about those aesthetics earlier, and why I didn't like AI autocompletion for so long was because it interfered with that massaging of the *"Ruby poem."* I've now spent well over 20 years absolutely loving the **Ruby** programming language because some guy in Japan rearranged the priorities of what was permissible to care about as a software developer.

Sam Parr

We have this thing, David. I'm now gonna call it the **MFM lean**. Sean, do you want to show them the **MFM lean**? We—you had us both. If we sit like this and we're just like, "you've got us to fall down..." [gesturing]. *If you're listening on Spotify, you have to go on YouTube to hear this part.* If you've gotten us to fall down your slippery slope, you made a comment about **longevity**, which is pretty cool. You talked about how all these people tried all these tactics and it didn't work. We weren't too trendy, and now we're sitting here and we still have lasted. You've built this amazing company that has made — I don't know — hundreds of millions, maybe billions, in cumulative revenue. Is there anything you do on a day-to-day basis within your company where you are making decisions to last five or ten years out? Are there *longevity* decisions versus short-term decisions? Do you actively think about that on a regular basis? Or maybe I could ask you the other way around, whichever is easier: what decisions would you make differently if you were just trying to, you know, get in and get out?

MFM

Good question. I think on the longevity front the **number one objective** Jason and I have is to ensure that *37* is still a place we want to work — not just want to work, but *like* to work; it's our favorite place to work. I see and talk to a lot of entrepreneurs who are in a hurry because they managed to build a company they don't like and they would love to get out of it. I find that tremendously sad. Not because they can't achieve other objectives in their life — maybe they have a tremendous exit and then they grit their teeth for the two- to five-year exit, and they're on hold-up and earn-out, and then they go on living merry, good lives. Great, lovely — I am glad for you. That's not what I want. I want to arrive at a station in life where I don't have to do things I don't want to do if they're not in service of a meaningful burden I have chosen to carry. Work is full of individuals — even at the highest levels, the CEOs and the founders — who are stuck in these loops that they actually kind of hate, and the only reason they're doing it is because of some begrudging obligation to investors or outcomes or whatever else have you. Jason and I, from the get-go, set the objective that we're not going to fall into that. We're not going to be instrumental about how we built this business because we're seeking the *after* — we're committing to the *now*. The now has lasted for twenty-seven years, and in my case for twenty-five years (I joined up in 2001), so that seemed to, actually counterintuitively, work for longevity. </FormattedResponse>

Sam Parr

Do you still go through quarters or months of angst where you're like, "We're right in the middle of this; this is frustrating to me. I don't want to be doing this, but we have to do it," or does that not even exist in your world? </FormattedResponse>

MFM

No, it's never been there. I'm not saying I've never—I've never been stressed. I certainly have stress points, not that many. I mean, I can literally remember almost all of them, but it's not because I'm *grinding towards some outcome*. It's usually those moments of stress because *external forces* have conspired against us for a hot moment, and we gotta figure our way out and that...

Sam Parr

Actually, well, *that's surprising.* Even when you went to launch, you said, "Hey — you're not, like, you know, we said we want to launch on this day; we will. Let's get all of our ducks in a row and make sure this launch is good." And if it doesn't feel good, I feel like it's shocking.

MFM

No — that's amazing. I think that's important. We were fortunate enough to have early success that, many years ago, we reached *escape velocity*: if this thing implodes, I'm not going to be out on the street. To me, that was the baseline. I grew up in Denmark, working class, where I did have, occasionally, near the end of the month, no more money. OK, well great — I guess we're eating at the grandparents' for the next couple of days because that's just what it is. If you grow up under those circumstances — and I actually have no qualms about that; most of all, that was great and I treasure having been brought up that way — it did leave me, for some time, with a sense that I would like to be at a place where I don't have to worry about the end of the month, whatever that means. We reached that place quite early because, in part, we were not just putting it all in. We took money out from day one — almost; not quite, year two at the very latest — we were pulling out profits. Then we had Bezos buying secondaries from Jason or I. That just set a baseline — they're like, "Alright, now we're pretty set." The next couple of years were very nice, and we ended up really early at a stage where I felt like we were in overtime. In 2008 I was like, "It's all gravy; I've already done the touchdown. I've already secured the base here." So if this stops tomorrow, I will look back on the whole thing with immense gratitude. What a privilege to be able to work on these incredibly satisfying products that customers really like, to have kicked off Ruby on Rails, to have been there at the birth of SaaS, to have seen everything. Wow. That is not something everyone can say, and I got to do it. So now I'm in *fluffy land*. If this ends tomorrow, I can be at peace with the whole thing. I think actually having that — I will use the word *instrumental* — detachment from the outcomes of the business allowed us to be better business people. It allowed us to have less ego attachment to specific outcomes that we did not have any power to influence anyway. The vast majority of anxiety that wrecks entrepreneurs and builders all the time is about forces outside of their control. The best you can do is do the best you can do. I don't have another 200% in me. I know I found the steady state where I get maximum productivity out of myself, and it's not by sleeping two hours a night for three weeks straight. I know exactly where that road ends — no, and it's not a place where I want to be. I am going to be exhausted, stupid, and full of mistakes. So we're going to build the setup in such a way that if Hey was going to flunk, okay — still plenty of margin. We still have base camp. We still have a bunch of other legacy products that are paying the bills, and way more than that. We get to have fun. We get to chase our ideas. We get to be ludicrously ambitious in our definition of it, which is: let's go head to head with Gmail — a great product that's free — and ask someone to buy an email system that we just came up with. I mean, that is a ludicrous mission, if I've ever heard one, and it worked. Hey is now — what, are we on year five? — millions of dollars. It's been a great success. It was a quite stressful birth, not because of anything we did up to launch, but because of what Apple did after launch. That's one of those scenarios I talked about where outside forces will apply stress to you, and in fact you should not shy away from that. I look back on that experience with Apple with, again, tremendous gratitude. I'm so happy Apple chose to be such a greedy dick about it because otherwise... </FormattedResponse>

Sam Parr

You—well, you have to give context. The context is: I think you complained that they were taking a **30% cut** from the App Store. Is that right?

MFM

Yeah. We launched **Hay** on the same premise we'd always had with **Basecamp** in the **App Store**: this is a companion app to a web product. We're not selling anything in this App Store. In the meantime, since we had launched, **Apple** had changed its mind. It wanted more—more. So we were met with this *shakedown demand* that unless we used in‑app purchasing and therefore gave them **30%** of our revenues, they would "destroy our business." When you first hear that, you think, "Wait — we've been building this for multiple years now, invested millions and millions of dollars, and it could all disappear if Apple just decides that we shouldn't get to live." Well, that sucks.

Shaan Puri

Sorry. So, what actually happened? They said, "So you have a button in your app that basically takes you to the web where you can pay for it." Great.

MFM

We didn't. You're saying, "We didn't"? </FormattedResponse>

Shaan Puri

Oh... you—oh, you just had it where you sign up on the web. It's a *companion app*.

Sam Parr

And so, wait — we have to give context. So hey.com, or *Hey* [email service], is a Gmail competitor, yes? So, presumably you would need your customer to have Hey at the bottom of their iPhone so they can click and read their mail.

MFM

Correct — you're not going to be competitive with an email service if you don't have an iPhone app. As it just so happens, most of the people who spend money on mobile software and subscriptions are on the iPhone. Therefore this was the admission to market: we did not have a viable business without this. We thought, "Hey, we know Apple wants to take **30%** if you're selling something through the App Store, so let's just not do that. Let's do the sale entirely on our own properties," so that we wouldn't rely on Apple for any marketing or anything else where they could have a legitimate claim that they own some of our business. Once people had signed up on hey.com for their new, amazing email address, they would go to the App Store, download the companion app, and log in with the credentials they already had. That kicked off this completely nonsensical battle with Apple, where, at the bottom of it, they were just like, "No — I just want **30%** of your business. What are you going to do about it?" They of course assumed that we, like virtually every other software company they've tried this shakedown tactic on, would roll over and accept it as the cost of doing business. But because our circumstances were as they are — and as we've been discussing now for quite a while — Jason and I just said no. We're not doing that. I would rather burn down millions of dollars built over two years than pay the gangster shakedown. I think that took Apple — well, I know it took Apple — by surprise, because we then entered into a two-week-long, very public skirmish over these terms and ended up in a place where Apple let us be and essentially rewrote the rules to fit the exemption around us and our email product. But not before causing a tremendous amount of stress during that two-year period.

Sam Parr

So that — but you **won**, you won, right? I mean, you got the outcome you wanted.

MFM

Largely right. We got what we launched—what we thought we were going to do. We thought we could launch a free app in the App Store, do no sales activity on that app, and then run our own business. Jason and I were like, we’re not looking for a handout here from Apple. We’re not looking for Apple to give us a bunch of customers. We will find our own customers, thank you very much. But we want those customers to be able to use the computer in their pocket that they paid $1,000 to buy to use the system with us. How should Apple have a say in whether your personal pocket computer should be able to be used with Hay? That just seemed preposterous and very much the wrong direction for technology to go. If we rewind a bit, this entire business—my entire career—is premised on two main things: the internet and open source. What those two share is that there’s no one to ask for permission. If I use a piece of open source software according to its license, I can do whatever the hell I want. If I publish a website on the internet and it’s not exactly CSAM, illegal things, selling drugs, I get to do it. I don’t have to ask anyone for permission. There’s a little bit more permission these days, but especially in the early days, no permission. No-permission tech. No-permission platforms. This is what I like. So this whole idea that now computing was going to be gate-kept by two companies—Apple and Google—was completely incompatible with what I wanted to see in the world. Therefore we had the margin to be able to do it. This was a new product; yes, we’d invested millions of dollars, but we still had the other thing. So we went to the mat for the principles of it—for our own integrity, for our own goddamn indignation over just how wrong this was and how much of a betrayal it felt like. I’ve been a Mac superfan—freaking twenty years. Jason and I— I don’t know if you talked about this—but Jason and I did an ad for Apple. You can still find it on YouTube, I think, in 2003 or something, where we’re all about like, “Apple’s amazing,” and we need these beautiful computers to do all our stuff. It was on the Apple website for quite a while. So it’s not like I came in with a grudge. I came in thinking there was a mistake. This was how the whole thing started. That turned out as well as it could have, but it did inspire me to explore new terrain. If I hadn’t had that experience, would I have built my own Linux distribution that is now used by tens of thousands of people? Would I have discovered this wonderful new world of the Linux operating system—of Hyperland, of Arch, of mechanical keyboards, and all this other computer stuff that exists outside of the walled Apple garden? No, I would not.

Sam Parr

"What device are you taking this call on? What are you on right now?"

MFM

I'm doing this call from my **Framework** desktop running **Omachi**, and my *delicious mechanical low‑profile keyboard*, and it all just worked beautifully. There is a piece of **Apple** in the equation: I still have an **Apple 32‑inch** monitor. I bought three of those when they came out for different locations, and they still work great. In fact, they work better than great — a wonderful monitor — and they work well with **Linux**. So there's still a little bit of Apple...

Sam Parr

"You told that story with the *veracity* — the *anger* — of a Shakespearean actor. The way your voice goes up and down was striking."

MFM

There is *definitely* some **fierce Viking blood** being awakened around here.

Shaan Puri

"Your ancestors will be so proud. *I love this.*"

MFM

*I hope.*

Shaan Puri

This is amazing, **David**. Thanks for coming on, man — we appreciate you doing this. Everyone should follow you on Twitter and the blog. Go use all your stuff — you guys are awesome. **Sam** and I have been inspired by you and **Jason** for a very long time. You do things your own way, and I think that's the highest compliment we can give. </FormattedResponse>

Sam Parr

You said you were quoting someone. You said **"I hate wisdom."** I could say that's a beautiful quote, but that's not the truth — it's not how we feel about your wisdom. So, thank you so much.

MFM

"Oh, thank you."

Sam Parr

"That's it. That's the pod."