The Exchanges

Q to give advice when there's so many people that are more successful than me. They should be giving advice, you know, this sort of imposter syndrome stuff. How did you justify teaching fundamentals, teaching advice, and writing a book on work when you're still in your twenties, and there was probably a thousand people that were above you that could have been like, what the hell does this guy know?

A 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 gonna call it like I see it, when I see it, whether I'm 19 or 15 or 46 or 37. And the other aspect of that is that both Jason and I did spend quite a long time working for other people. Now, long time in the grand scheme of things. Did we spend 20 years? No, but I'd been working since I was 15. Uh, well, even earlier than that, but I'd been working for other people directly in the sense of I have a boss since I was 15. So by the time I'm 26, I've been In business, to whatever degree that is, either as an employee or running myself for a decade. Now, I don't even think you need that. I think what you need is exposure to novel terrain, With enough sort of influences and being informed somewhat of what other people think, and then like your token generation machine will start producing if you are of the kind of constitution that I am, which is one of the ways I try to internalize the best lessons from what I'm going through is to share. Is the old adage that nothing makes you learn a subject better than trying to teach it.

AI assessment note: “I've been blessed with a completely irreverent personality that thrives in exactly those kinds of circumstances.”

Q Because it's very rare. I mean, building, he's built like the 17 largest company in the world. That's rare. It's also very rare where he's been at the helm the whole time. Uh, is there anything, anything cool about like the evolution of like a computer nerd to being like a proper CEO of a 10,000 person company? Is there anything cool that you can, I can learn about that?

A What's funny to me is that you posted 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 of 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 what he is also is now the head of this giant corporation that is responsible for, I think I saw something like, 15% of, I mean, 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 internalizing into his character composition. He's very much still the computer nerd, and I think this current phase that we're in with the AI and the agent explosion just demonstrates that to a T. 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 got to 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 like, 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 it was just really early on it. And so much of that came from that ne…

AI assessment note: “Not true at all. He's still a computer nerd. Absolutely.”

Q But you won, you won, right? I mean, you got, you got the outcome you wanted?

A Largely, right? We got what we launched, what we thought we were due, right? We thought we were due that you could launch a free app in the app store if you did no sales activity on that app, and then you did all your own business, right? Like Jason and I was 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're paying a thousand dollars to buy to use the system with us. Like, 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 end of where I wanted technology to go. Because if we just rewind a bit, this entire business, my entire career is premised on two main things. The internet? Open source. And 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 stuff, 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. So, No permission tech, no permission platform. This i…

AI assessment note: “Largely, right? We got what we launched, what we thought we were due”

Q But you won, you won, right? I mean, you got, you got the outcome you wanted?

A Largely, right? We got what we launched, what we thought we were due, right? We thought we were due that you could launch a free app in the app store if you did no sales activity on that app, and then you did all your own business, right? Like Jason and I was 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're paying a thousand dollars to buy to use the system with us. Like, 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 end of where I wanted technology to go. Because if we just rewind a bit, this entire business, my entire career is premised on two main things. The internet? Open source. And 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 stuff, 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. So, No permission tech, no permission platform. This i…

AI assessment note: “Largely, right? We got what we launched, what we thought we were due”

Q to give advice when there's so many people that are more successful than me. They should be giving advice, you know, this sort of imposter syndrome stuff. How did you justify teaching fundamentals, teaching advice, and writing a book on work when you're still in your twenties, and there was probably a thousand people that were above you that could have been like, what the hell does this guy know?

A 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 gonna call it like I see it, when I see it, whether I'm 19 or 15 or 46 or 37. And the other aspect of that is that both Jason and I did spend quite a long time working for other people. Now, long time in the grand scheme of things. Did we spend 20 years? No, but I'd been working since I was 15. Uh, well, even earlier than that, but I'd been working for other people directly in the sense of I have a boss since I was 15. So by the time I'm 26, I've been In business, to whatever degree that is, either as an employee or running myself for a decade. Now, I don't even think you need that. I think what you need is exposure to novel terrain, With enough sort of influences and being informed somewhat of what other people think, and then like your token generation machine will start producing if you are of the kind of constitution that I am, which is one of the ways I try to internalize the best lessons from what I'm going through is to share. Is the old adage that nothing makes you learn a subject better than trying to teach it.

AI assessment note: “I've been blessed with a completely irreverent personality that thrives in exactly those kinds”

Q Because it's very rare. I mean, building, he's built like the 17 largest company in the world. That's rare. It's also very rare where he's been at the helm the whole time. Uh, is there anything, anything cool about like the evolution of like a computer nerd to being like a proper CEO of a 10,000 person company? Is there anything cool that you can, I can learn about that?

A What's funny to me is that you posted 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 of 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 what he is also is now the head of this giant corporation that is responsible for, I think I saw something like, 15% of, I mean, 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 internalizing into his character composition. He's very much still the computer nerd, and I think this current phase that we're in with the AI and the agent explosion just demonstrates that to a T. 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 got to 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 like, 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 it was just really early on it. And so much of that came from that ne…

AI assessment note: “Not true at all. He's still a computer nerd. Absolutely.”

Q your company where you are making decisions to last five or 10 years out, uh, or being, you know, like longevity decisions versus short-term decisions? Like, do you actively think about that on a regular basis? Or maybe I could even ask you the other way around. Whichever is easier. What decisions would you make differently if you were just trying to like, you know, get in and get out?

A Good question. I think on the longevity front, the number one objective, both Jason and I, is to ensure that 37 Sigils is still a place we want to work. Not just want to work, but like to work is 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. And I find that tremendously sad, not because they can't achieve other objectives in their life, like maybe they have a tremendous exit and then they, Grit their teeth for the two to five year exit period when they're on hold up and earn out, and then they go on living merry good lives. Great. Lovely. I I'm 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. And work is full of Individuals, even at the highest levels, the CEOs, the founders, we're 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. And Jason and I, from the get-go, just set the objectives, like 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 and the n…

AI assessment note: “on the longevity front, the number one objective... is to ensure that 37 Sigils is still a place we want to work”

Q your company where you are making decisions to last five or 10 years out, uh, or being, you know, like longevity decisions versus short-term decisions? Like, do you actively think about that on a regular basis? Or maybe I could even ask you the other way around. Whichever is easier. What decisions would you make differently if you were just trying to like, you know, get in and get out?

A Good question. I think on the longevity front, the number one objective, both Jason and I, is to ensure that 37 Sigils is still a place we want to work. Not just want to work, but like to work is 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. And I find that tremendously sad, not because they can't achieve other objectives in their life, like maybe they have a tremendous exit and then they, Grit their teeth for the two to five year exit period when they're on hold up and earn out, and then they go on living merry good lives. Great. Lovely. I I'm 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. And work is full of Individuals, even at the highest levels, the CEOs, the founders, we're 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. And Jason and I, from the get-go, just set the objectives, like 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 and the n…

AI assessment note: “on the longevity front, the number one objective... is to ensure that 37 Sigils is still a place”

Q Gurley's book, and then I just looked it up, uh, and it's like a, it's like a, a study. And the reason I'm bringing this up is I've been, I've been obsessed over that fact. I was, that just seems astronomical. And then you brought up the idea of crystallized versus liquid, uh, Knowledge, and it just solidifies that. It kind of adds to that. Isn't that a crazy stat?

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

AI assessment note: “That is wild. And do you know what's funny?”

Q Gurley's book, and then I just looked it up, uh, and it's like a, it's like a, a study. And the reason I'm bringing this up is I've been, I've been obsessed over that fact. I was, that just seems astronomical. And then you brought up the idea of crystallized versus liquid, uh, Knowledge, and it just solidifies that. It kind of adds to that. Isn't that a crazy stat?

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

AI assessment note: “That is wild. And do you know what's funny? I mean, we all read”

Q Are you able to give any, uh, frame or any ballpark for previous numbers, if you're comfortable, so we understand?

A Not really. I mean, let's just say ridiculous. I think that's a, that's a good ballpark, right? And certainly if you compare to any of the public SaaS companies, like as we were in a different industry, right? Like often industries have a tendency to core less around a certain profit margin. And it seems like public market SaaS is core less around like, I don't know, -10% or something -20%. Ridiculously long stretches of unprofitable growth, partly because there's all these other hacks of 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 could just focus our time on what we like to do. And you know what? It just so happens to be that neither Jason or I love running minutiae A-B test to squeeze out 0.01. And That's very often what's needed if you want to tweak something. You run a thousand of these experiments, right? Like, not two. You just, you stick to it and you keep grinding away. And I think grind is actually a good word here because this is something I often hear entrepreneurs talk with such pride in their voice. Yeah, I, I grind. Like, this is why I'm working a hundred hours a week or a 120 hours a week. I'm just grinding, grinding, grinding. …

AI assessment note: “Not really. I mean, let's just say ridiculous.”

Q Are you able to give any, uh, frame or any ballpark for previous numbers, if you're comfortable, so we understand?

A Not really. I mean, let's just say ridiculous. I think that's a, that's a good ballpark, right? And certainly if you compare to any of the public SaaS companies, like as we were in a different industry, right? Like often industries have a tendency to core less around a certain profit margin. And it seems like public market SaaS is core less around like, I don't know, -10% or something -20%. Ridiculously long stretches of unprofitable growth, partly because there's all these other hacks of 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 could just focus our time on what we like to do. And you know what? It just so happens to be that neither Jason or I love running minutiae A-B test to squeeze out 0.01. And That's very often what's needed if you want to tweak something. You run a thousand of these experiments, right? Like, not two. You just, you stick to it and you keep grinding away. And I think grind is actually a good word here because this is something I often hear entrepreneurs talk with such pride in their voice. Yeah, I, I grind. Like, this is why I'm working a hundred hours a week or a 120 hours a week. I'm just grinding, grinding, grinding. …

AI assessment note: “Not really. I mean, let's just say ridiculous.”