The Story
This episode starts with a joke that lands because it is barely a joke: the guest has built something "incredibly exciting and incredibly boring," which turns out to be custom accounting software. Paul Ford and Rich Ciotti bring on Craig Mod, who lives in Japan and has the kind of work life that breaks ordinary bookkeeping tools. He is an American citizen, pays taxes in Japan, still has to file in the US, earns money through memberships and books, and runs a one-person creative business spread across countries, currencies, and institutions. That setup alone explains why off-the-shelf software starts to feel less like help and more like a trap.
Craig is a good guest for this because he is not a tourist in tech. He has been programming since childhood, studied computer science and fine arts, and has spent years moving between software, publishing, design, and art. His writing life grew out of that mix. He built his own membership program instead of using someone else's platform, then used that support to fund long solo walks across Japan. Those walks become nightly dispatches, photographs, and eventually books. It's a striking life, but the business side of it is a mess in the way many independent careers are a mess: several revenue streams, paperwork everywhere, and a lot of dread when tax season arrives.
That dread is what pushed him to build. The software he describes is less a reinvention of QuickBooks than a personal command center. It tracks income, expenses, expected taxes, and medical receipts, and it remembers the forms and patterns from prior years. The point is not novelty. The point is relief. He wanted a system that fit his actual life instead of forcing his life into someone else's categories.
From there the conversation widens. Rich and Paul use Craig's project as a way to talk about AI as software, not magic. Rich keeps bringing the discussion back to a grounded point: if you understand how software gets stood up, you can do a lot with these tools. Craig's accounting app is one example of what happens when a person with domain knowledge and technical fluency finally gets tools that let him make exactly the thing he needs.
Then the tone shifts. Craig raises a darker question about abundance, meaning, and what happens if machines take over more of the labor that once structured human life. Rich pushes back. He thinks that ten years from now, much of this will still look recognizable, with people using AI in ordinary ways inside ordinary organizations. He does not see AGI swallowing everything so much as culture slowly absorbing the tools. The disagreement never turns into a fight. It feels more like three people circling the same uncertainty from different angles.
Main Themes
The clearest theme is that AI becomes interesting when it leaves the demo stage and enters some annoying, specific corner of real life. This episode is about taxes, receipts, and filing obligations, but that is what makes it persuasive. Craig did not build software to prove a theory. He built it because his life had too many exceptions for standard products to handle cleanly.
A second theme is that the people getting the most out of this moment are the ones who already understand how software is put together. All three speakers keep returning to that gap. Craig can build his own tool because he knows the stack, the architecture, and the logic behind it. Rich and Paul are blunt that this is still out of reach for most people, not because they lack intelligence, but because software knowledge has usually been taught through frameworks and jobs rather than through a plain-language map of how systems fit together.
The last thread is about limits, both human and technical. Craig sees AI opening extraordinary creative and practical power while also stirring up old fears about value, work, and purpose. Rich answers with a more grounded faith in human habits and human mess. Between them, the episode makes a useful point: the future may arrive through very strange tools, but it will still run into ordinary people, old institutions, and the same unresolved questions about what matters.
Full Transcript
Hi, I'm Paul Ford. And I'm Rich Ciotti. And this is the Aboard podcast, the podcast about how AI is changing the world of software and the world in general. And Rich, we have a very special guest in the studio today. Yeah. We're going to talk to him. And he has something both incredibly exciting and incredibly boring to share. And I think that's going to be cool. I love both of those things. Me too. Let's do it. Let's play that theme song. Richard. Yes. What is our company? What do we do all day? We are Aboard. We are based in New York City, but we've got a team around the world that comes in, understands your organization or business, puts really talented people to sort of triangulate on what you need. And then we use all these incredible tools to solve problems for you. We're an AI transformation shop. We don't just come in and like, come on, let's unleash the agents. No, we don't do that. We think about what you need, and then we're in all sorts of interesting places nowadays, Paul. So first of all, things are going good. If you want to talk, it's a wonderful time to reach out. It's busy. The shop is busy. But you and I have shipped software for over two trillion years. Yes. And I'm going to tell you something about AI. You ready? Go. It's software. Yes, it is. It is just software. It's weird. It's different. It's got a different shape. But if you can understand how to stand up a piece of software, you can actually get some of this exciting super revolution into your org. So give us a yell. Aboard is very reachable on the internet, on the web via hello at aboard.com. We'll give you that email again when we get out of this podcast. Let's do it. What do we got here, Paul? Well, we have an old friend of sort of everything. I mean, many companies ago, I think we started talking to this person. This is Craig Mod. Craig. Hello. Welcome, Craig. Hi. It's good to have you here. Thanks for having me. I want you to explain who you are in a second, but I'm going to tell you the specific reason that we reached out was that you wrote a blog post. You reside in Japan, and you have very complicated accounting issues as an American residing in Japan, working for lots of different companies, mostly around the design and consultancy field. And so you set out. I remember when AI started, somebody took me aside and they were like, could we build our own QuickBooks? And I was like, never do that. That's the worst idea I've ever heard. And then you went ahead and did it. And it worked really well for you. And so I think we just want to talk about what it's like to build your own accounting software. Yeah. The most exciting subject that has ever been on Earth. I mean, way to set up a cliffhanger, Paul. Before you do that, Craig, tell us about yourself, but also tell us about the skills you feel like you're pretty comfortable with. Yeah. I mean, I've been programming since I was like eight. So I have this long technical background. And then I've been involved with books and publishing forever as well. And so those are like the two things, books, making books, making physical books, and then doing technical stuff. I actually got a degree in computer science and fine arts. It was like this weird double thing. Anyway, it was good. OK. So I'm very comfortable in the land of technology. And then as e-books and all that stuff started coming on board, I was very comfortable with that while at the same time looking to McSweeney's as kind of a, you know, North Star for making cool physical things. And I've been doing that for a decade. For all the product managers out there who don't know, just go to like McSweeney's.net. You'll get a sense. Yeah. So those are the two universes I've been living in, like a big kind of deep technical world and all the technical stuff I've been doing has kind of been in support of publishing or writing or whatever, things like that. Craig, would you say you had a career at the intersection of technology and the liberal arts? Would you say that? I would. Yeah. That's a horrible thing. But you're not coding every day. You're not coding every day. No, no, no. And I was in my 20s, you know, but mostly it was personal projects. It was weird like database stuff. You know, I had a fellowship at Fabrica. This is like this sort of digital art collective thing in northern Italy. I'm absolutely nodding as if I have any idea what that is. Jonathan Harris, remember number 27? Anyway, like all the, you know, Casey Rees, you know, all the, you know, John Maida, obviously, all the old digital art people. I was kind of like in that zone and trying to like emulate them and following them around the world. Okay. So, non-tours, but you bring together communities to go around and do things and you are a very serious photographer as you go on these very long walks. Yeah. Yeah. I mean, most of the walks are solo, so like 30, 40 days alone, which is not indicative of anything broken or weird. No, it's totally normal. That's called a guy going for a walk, Paul, just to clarify for you. But the whole point I was getting to before that debacle is that you are a publisher and you have a community around these sort of community building non-tours. Yep. And you have to manage this because obviously no money ever changes hands, but somehow money comes and you have to manage the money and there's all sorts of stuff going on. Sure. Yeah. Paul, just give me a sec here, okay? I'm going to take a look. Craig, how do you make money? So, I started a membership program. Okay. I've been writing a newsletter for 15, 16 years. And eight years ago, seven and a half years ago, I hit a wall and I couldn't get anything published where I wanted to get it published. And I thought, I'm worthless and I have no value and I should go live in a dumpster. Yeah. But membership programs were becoming a thing. And I wrote a piece for Wired about how digital books didn't become what we thought they were going to become, but membership stuff and online publishing is kind of more interesting than it's ever been. Substack world. Yeah. Right at the beginning of that Substack stuff. And so I launched a membership program. Your own. My own thing. Yeah. Because I'm pathologically incapable of being on anyone else's platform and launched that. And then from that, I divined a weird permission to start going on these huge walks that I wanted to do in Japan. Okay. So I've walked from Tokyo to Kyoto three times. I've walked thousands of kilometers all over other parts of Japan. And I walk and I do these pop-up newsletters. And the membership program essentially funds it. It gives me permission to go do these because people are paying me to go do the stuff. You've got enough of an audience paying you. Okay. And then from those, I write books basically. As I'm walking, I'll walk for eight hours a day. I'll talk to people along the road, photograph, take notes. And then every night I write 2,000, 3,000 words and then that goes out every night. And so it's this weird aesthetic practice that I'll do for 40 days in a row. Wow. And then you end up with this corpus of 60,000, 70,000 words at the end of it and all these photos. And then you can kind of distill that into a book. And that's kind of been the process over the last six, seven years. And I had a book come out with Random House last year, which was kind of making me official in a way. Got it. People suddenly go, as long as you can say like Random House, then people go, oh, you are a writer now. Yeah. This is real. Yeah. So, okay. So you've got sources of income from the members paying you to be members of your org. So membership, book sales, that's it basically. Yeah. That's the big income. Right. And so a little messy. Yeah. A little messy. Well, because I live in Japan, I have, you know, whatever. You have bank accounts in both countries, America and Japan. Ah, so you've got that issue. I'm a U.S. citizen and you always have to file in America even though there's a tax treaty. So all the taxes I pay, I pay primarily a hundred percent in Japan. Then those get carried over as part of the tax treaty, so you can offset your American taxes with that, but you still have to go through the filing process. It stinks. America is the only country in the world, except for one other little country that makes you do this. If you're not a resident, but you have citizenship, you have to file the full thing. But you love this. This is fun. You love taxes. I don't know about this one. There is the amount of anxiety I have in January every year. Oh, yeah. Panic attacks. Really? They're going to take everything away from me. I'm going to lose everything. You don't understand the scarcity mindset that like just does not disappear. We understand. When I got married, my wife found like a box of receipts and papers and it was like, it was like a year to unpack everything that had not been dealt with. No, the scarcity mindset. It's just crippling. To be clear, I'd paid everything and added up to like Income, expenses, expected tax estimates, just so like a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just dump any kind of medical receipt form. So it's collecting that. And then it knows what forms I submitted last year. And so it has a running tax estimate for the year. And then medical, there's like a thing where I can just Counter argument here. Let me reduce the pessimism for a second. For a sec. Go, go, go ahead. Finish your thought. I don't want to hear from you anymore. I don't want to hear from Craig. But I don't think it's a bad thing. He's staring into the darkness. I have a lot. But I think what's interesting is I think actually on the other side of this is a place of deeper, more interesting meaning where it's like we're forced to contend with these questions of why are we here? What are we doing without this kind of scaffolding? You think humans are gonna do that, Craig? I'm saying this is the optimistic view. This is the optimistic view. I'm looking at the people who have great abundance. Yeah. And we're all looking at them. And I don't think any of us are going, I want to do that or be that. And so that's weird that maybe there's a certain kind of educational component or spiritual component that's missing. Right. And it may just be in our code. And that's why I say, I don't know if we get over the finish line here. You know, and maybe our thing is to like just barely get the machines over and we hand off all our knowledge and then we disappear. That could that could also be, you know, the next hundred year outcome. Yeah. Okay. Okay. No, no, no. I actually like, okay, I have a different point of view. I know where you're gonna go. You're gonna, you're gonna, but I'll tell you what, I know where I'm gonna go. Don't speak for me, Paul. I'll speak for you. I'll tell you what I see. Tell me where you go here. Yeah. And then I'll do, I'll do me. I increasingly am of the opinion that if you come and if you came into this room 10 years from now, this company is still going, you know, maybe we've grown a little bit and you sit down and you talk to someone and you talk about how they're using AI, it will be very legible and many human behaviors will be exactly the same. And we won't have achieved AGI and everyone will be sort of on the cusp of another big thing. Like I really, I see this one kind of slowly starting to get eaten up by culture. And so I'm just like, I know where you, I've been where you've been. Like I go back and forth on it, just kind of like you do, I'm sure. And just like, is this it? Are we done here? Is this, you know, all those things I learned, do they matter? But every time we pressure test them, just more and more human behavior spills out and it turns out we're not going to change. So I mean that overlaps with my perspective on this and my perspective on. You don't even need to state it then, do you? You know, that's a good point. No, you go ahead. Thanks for listening, everyone. How does it overlap and then we'll clear it out. No, I, when I got to law school, I was really thrown off by the fact that everything was open book. Rich went to law school, by the way. I went to law school. And it was very strange to me that final exam, open book, the bar exam, the bar exam is open book. Yeah. Bar exam is open book. I didn't know that really. Yeah. Yeah, but it's useless. But you guys, it's a pretty big book. No, no, there's no book. There's nothing you can take. There's nothing to help you. Because they're going to cover the vast array of law or like of all law. That's what I'm saying. Like you need a library. Wait a minute, no wait, the bar exam is not open book. Yeah, there we go. Thank you. All my exams in law school were open book. Okay. Every single one, which was like not unusual at all. I think a couple I had like legal writing that were not obviously, but most were open book. And it threw me off. And when you look at law, you mentioned the law and how good it is at like writing a brief or a memo that's in legalese and that makes an argument. The truth is the best lawyers are very creative. Now, can the models get there? Let's park that question for a second. We can always ask that question. But the truth is the really thoughtful, creative thinkers around all this stuff. And that is where all the quality lies. Like the best tax lawyers, which are the most expensive lawyers, like not only know the code, but know how to like piece together strategies around tax strategy, for example. Really boring shit, but that is a product not of any knowledge, but a product of their creative and sort of deductive thinking, right? And I think you can find that in a lot of things. And I think all of this stuff, I have not seen a lot of quality, frankly. Like it's been two years now. Everybody's just having sex with that prompt box and I have not seen anything like, wow, that is an amazing output. I've seen all kinds of things that look like a lot of the same things. But I'm not seeing anything except, and why, Craig? And you know this as well as anyone. And the truth is you have to come at it from such a different place and reset a lot of assumptions to do something exceptional. That's still the case, right? Whether it be product or design or anything else. And so I think the limitations we're hitting are not the systems. They're the humans falling into a lull here because we're just blown away by this right now, right? Well, I mean, let's throw it back to Craig, which is you sat down and consulted with yourself and you made a piece of software that you are using to achieve a goal. And it's working because you're paying your taxes, I'm assuming on time, and you're getting money back and things are working. Yeah. Okay, so you are in that 5% of people now, and it's you and you know the whole stack and you've been doing it for a while, right? But let's just coach people a little bit at the end of this, right? If you wanna get over from that 5% back into that, if you wanna get out of that 95%. Well, there's also the assumption that the five, the tools will get better and the five will be 10 and will be 15. It'll probably welcome more people in. But I don't think anybody has an instant answer for this. I don't either. Where should people start? Where do you, if you were to sit somebody down who's interested in this world and wanted to do something like what you did, where would you start them? Catholic church, maybe. Okay, there you go. Just go. Try to find God. It's hard. I think it's a hard answer. I think it's a really hard answer. It is. I'm throwing it out because I don't think anybody, I mean, I don't have a starting point right now because every time I try to come up with a starting point for someone, it involves taking apart the history of tech over the last 25 years. Absolutely. I mean, the starting point is being really curious when you're young and just being in love with this stuff. I mean, I just love this stuff. We're lucky. I just love it. And so for me, getting this God-like piece of software that I can go deeper than I've ever been able to go building things that I've wanted to build as quickly as I can build in the exact way I want to build them, to me feels, that's what feels so magical. And that's why for the 95% that aren't touching all this stuff or using it, it's hard to explain how special that feels. It would be like you had candlelight and then somebody gives you a nuclear reactor and a bunch of stadium lighting, and now that's your reality. You can stadium light 24 hours a day. You can do anything. We lucked out in a way. Without flashlights in the middle. Just straight to incredibly. I feel the same. I think we did. I think like, you know, when I think about the domain knowledge necessary for you to pull off what you did, it is web architecture. It is the difference between APIs and websites. It is servers. It is clients. It is Python. It is JavaScript front-end tech. Like I've got 20 things that you kind of need to conceptually understand in the abstract. And I think here's what I do believe. I do believe that that architecture can be taught, but it's been taught and learned in terms of specific implementations. And that's how people pick it up. You get on a project and we're gonna be using Tailwind. What's Tailwind? Here we go. Okay. And I think that all of that's gonna get really abstract. But teaching that kind of architecture and blueprint for how software comes together, like nobody does that. That's not how we teach it. It's also, does a 45 year old bookkeeper wanna go learn that? No. Right. No. But there are plenty of mid-sized orgs that might make a... I think organizations is another podcast we could talk about how orgs can help people as, you know, kind of elevate. I was talking to somebody in publishing and it'd be really amazing for them to get more of their backlist exposed so they could do stuff with it, et cetera. Anyway, okay. There's another option, Paul. What's that? You can call a board. Yeah. Or you could call Craig, but he would... Craig will probably say no, but a board will say yes. Yes. This was a really fun conversation, Craig. I think we feel like we could keep talking. Yeah. Well, can I just inject something at the end here? Absolutely. Yes. Like the negative whatever thinking