
We chat with Paul Ford about the strange paradox of AI that makes ideation blindingly fast but leaves the hard work of product thinking as slow as it ever was, why the best thing you can bring to this moment might be taste rather than technical skill, and what it actually means to build a company around tools that didn't exist two years ago.
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Paul Ford
Sometimes you can replace a designer with a robot that just says, we need to do more research before the work can happen. Right? And that's the thing I actually like about designers. They're like, hold on a minute, we need to bring it in. We need to understand. And it can drive you crazy when you're pitching a project and trying to get it over the line. But they're right. We have to get context before this product can get moving. And it's going to start with mood boards and ideation, but it's going to end with us sharing a language with the customer. It's visual and it's words and its texture and its vibes and it's all of that.
Eli Woolery
Paul Ford likes to call himself a fun Cassandra. Someone who, like the priestess in Greek mythology, sees trouble coming, but unlike her, tries to make the warning as entertaining as possible. He's the writer, developer and co founder of the tech agency aboard who saw Claude code drop last November and immediately understood it was going to change everything, while finding to his surprise that most people around him simply weren't seeing it that way.
Aaron Walter
That same instinct is what drew him into AI early. Where others hedged, Paul dove right in. Vibe coding nonstop, running full enterprise subscriptions for his entire team and building in earnest. But he's not a fanboy. He's a critical optimist who believes something important is happening right now while holding equal concerns about the companies pushing it, the students expected to learn from it, and the decades of hard won knowledge that might be quietly evaporating in the the rush. Paul is also an English major who sold an agency, a developer who thinks in prose, and he's a father of 14 year old twins. He is one of the most multidisciplinary thinkers that we've encountered on the show. He won the National Magazine Award for writing an entire issue of Bloomberg Business Week dedicated to explaining programming to mass audiences. A 38,000 word essay called what Is Code? A regular contributor to Wired magazine and published in the New Yorker and MIT Technology Review, he's one of the rare writers who can make the inner workings of software feel urgent and human.
Eli Woolery
So he's exactly the kind of thinker this moment needs. Someone who can write code and read the room and who cares about quality as much as velocity. He can also make you laugh while explaining why you should probably be just a little bit worried. This is DesignBetter, where we explore creativity at the intersection of design and technology. I'm Eli Wooler.
Aaron Walter
And I'm Aaron Walter. If you're hearing this you're not currently on our Premium subscriber feed. DesignBetter Premium subscribers enjoy weekly episodes. That's four episodes per month rather than just two, and all of them are ad free. Plus you'll get an invitation to our monthly AMAs with the smartest folks in design and tech. And if you subscribe at the annual level, you'll also get our Toolkit, a collection of our favorite design and productivity tools like Perplexity, Miro, Read AI and more. You'll hear a preview of this episode, but if you'd like to hear the full conversation, please consider becoming a Premium Subscriber@designbetterpodcast.com subscribe the podcast is available to everyone through our Skype Scholarship program, so if you can't afford a subscription, just shoot us an email@subscriptions.com we'll help you out. We'll return to the conversation after this quick break.
Eli Woolery
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Paul Ford
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Aaron Walter
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Paul Ford
Come share the warmth of stories passed down through generations.
Aaron Walter
This is a place with a past
Paul Ford
that is fully present today and all yours to explore.
Eli Woolery
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Aaron Walter
And now back to the show.
Eli Woolery
Paul Ford, welcome to Design Better.
Paul Ford
Thank you so much for having me.
Eli Woolery
We're so excited to have you. Our mutual friend Meredith at the New York Times invited you to their wonderful location and we heard rave reviews. So we thought we gotta get you on the show. And I have been listening to some interviews, one most recently with Slate magazine, I think it was that you're on and there was something that caught my attention where you called yourself a fun Cassandra and I thought that was great. And for folks that don't know the Greek mythology reference, Cassandra was this figure that made these dire predictions in not such a fun way, but you spin it in a fun way. So maybe you could speak to that a little bit and how that shapes your attitude towards our current era of AI.
Paul Ford
Yes, okay, so I make predictions sometimes and sometimes they're pretty good. Like I can go back and find I saw that this was going to be a big deal and it'll be like some boring web thing. I'm wrong a lot too, by the way. I can absolutely find tons of places where I made very bad predictions, but every now and then I kind of nail it and AI hit and claude code hit and it hit around November and my background is as a developer and a writer and I was just like, oh, this is going to be a really big deal. And I was really surprised, I think, to find that people weren't seeing it in the same way that I was. And so I felt that I'd fallen back into fun Cassandra mode. The worst prediction I ever made that was also the truest was I saw Gamergate happening and it was all this conflict online about just, if you don't know what it is, go read the Wikipedia page. And I just went like, if you want to know what the future of American electoral politics looks like, it'll be like Gamergate for the rest of your life. And it was like the saddest thing to be right about. I like to pick a culture. I'm a very anxious person and so I poke around. So I think with AI, I feel very much like the Fund Cassandra because I'm like, I think this is a really interesting empowering tool. I think we should be very critical of it. I don't know if I love the companies that are pushing it as hard as they are. I think the entire tech industry. Eli, you're in Stanford area, you've seen how ridiculous the billboards are. But at the same time, there clearly is something here. Work is getting done very quickly and things are changing. And so it's not even a prediction, it's an observation. But it still didn't register as good news for a lot of people.
Aaron Walter
Before we hit record here, you said some stuff that very much resonated with me. A little setup here for our listeners. You run an agency called Aboard Co Run Co Run. All right, so you're a key figure in this business and it's a rather forward thinking business in that it's an agency and you're using AI to provide services and build software for your customers. Now most folks would think like, hey, that sounds like a bad business model because AI isn't putting us out of a job. And you're sort of embracing that. It is not. It's actually accelerating. Accelerating. We can come back to that topic. So set that to the side. But you said that with your clients, the way that you're using AI is making the ideation like, let's explore the ideas accelerate like crazy fast. And then the last part of actually building the thing out, it's as slow as ever. In fact, maybe slower. I'm experiencing this right now. I'm working on a small project. I'm building my own website. And once you kind of get through the clear ideation, the building is still just a slog. It's just still a lot of shit you gotta do. I'm curious to hear how this is playing out for you and your colleagues professionally.
Paul Ford
It's really tricky and it's really hard to articulate. And I think it's because people are seeing these wild results at the prompt. You're typing things in and you're getting a PowerPoint deck or it's writing you all this code and it's incredibly fast, it's incredibly high velocity and it's very easy to get a very standard thing, even a pretty big standard thing to exist. So what's a standard thing? A standard thing is an outline for a research report, a business case for something, a summary of a lot of documents, a PowerPoint that looks kind of like all the other PowerPoints. And a lot of times that's actually better than many of the materials that you might have had before. And so that gets really exciting and motivating to people. But I've been kind of vibe coding nonstop since November. Less because I need to for work and more because I sort of on the hook to understand and what I'm finding. We're finding this throughout the company because I'm not the only one. There's lots of people building. We sort of went in all full enterprise subscriptions. Every engineer in the firm, everybody we work with is using this stuff. Even though a lot of the things we're delivering are not super AI, but are just classic software, just faster. And we had a client come in in the sciences and they built this very intense machine learning model and they were having trouble getting people using it and they're like, could we just get an LLM in front of this and could we do some other stuff? One of our heads of engineering built out a really nice workflow driven, multi step wizard style interface for this. It's just very mature. He's been at it forever and it feels dangerous to show it to them because in three days I can get you kind of a miracle. But after that it just becomes product again. We got to have meetings to talk about what we want and we got to iterate. The coding is really fast, but the thinking is actually not that much faster. It's maybe a little bit faster or possibly a little bit slower because we have so much more product to work through. And so this dynamic is really tricky because once people get that taste of the incredible acceleration, they're like, well now it's always going to be like this, it's always going to be this easy. We'll just type it in But I actually don't see product going away. I think everything still needs to be there.
Eli Woolery
I think it's interesting as you're talking about it and also as listening to you on the other show. It got me thinking about this project I did years ago, which was for a friend of mine who runs a commercial real estate kind of education company, and he wanted to build a product that he saw a need for in that market. And I didn't know anything about commercial real estate at the time, nor do I now, really, but I was like, okay, yeah, I'll help you with this project. And I designed all these screens, and we had a developer team working with us, and it made me think I could have built that prototype now in like a day. But the rest of it, you know, you had to handle some sensitive financial data, things like that. I still couldn't do that on my own. At least it seems like, okay, the prototype's really accelerated the rest of it. There's still a lot of complexity, and people need to have some deep knowledge. And now there's things like Mythos coming around where it's like, there's some serious vulnerabilities in the things we're building. So that stuff's all pretty interesting.
Paul Ford
I want to throw back to you as design leaders, because I think this is really tricky. So I love designers. Sometimes you can replace a designer with a robot that just says, we need to do more research before the work can happen. Right. And that's the thing I actually like about designers. They're like, hold on a minute. We need to bring it in. We need to understand. And it can drive you crazy when you're pitching a project and trying to get it over the line. But they're right, right? Like, we have to get context before this product can get moving. And it's going to start with mood boards and ideation, but it's going to end with us sharing a language with the customer and with the client and with the user. And we need to have that language. And it's both visual and its words and its texture and its vibes, and it's all of that. And what's very wild about this moment and that prototype you could build in a day, and the stuff that we build, the language kind of comes for free because LLMs are language machines. And so the common language and understanding that used to take months to understand, and it used to take you a really long time to internalize. People had all kinds of processes and forms they filled out and things that they did. You can get that at the snap of a finger. And what's weird is the person on the other side is like, wow, you really get it. You figured it all out. It looks like you did that work. And that is a dangerous one because I think it's very good for closing a deal. Disclosure gets really tricky. I've tried to be really, really transparent with Buy and be like, hey, just so you know, I used AI to help me generate this PowerPoint. I don't really necessarily know what's in this prototype. I sent someone an example from a little, like, product generator tool I was playing with and they're like, wow, can I have that idea? And I realized I didn't know what that idea was. Like, I hadn't looked at it. I just showed them a thing and I was like, absolutely. I hope you make a billion dollars. We're in this very weird world, but I don't really know. Maybe we can pick up the language more quickly and so on. But that part of the work, where you're a really good partner long term, where you really understand their domain, where you think about where their revenue comes in and you think about where their success comes in, or their clients and their stakeholders, and you build that shared understanding that was always really a critical part of design as a practice. I feel it's under threat. And it's not because the code is really fast. It's because it's almost like we've done a magic trick and it's embarrassing to have to go back and be like, no, that was just a magic trick. I don't really know what your business is.
Aaron Walter
How are clients receiving this idea of, I'm an expert, I know software, I've been at this for decades, and I'm going to go out and use AI to generate this thing for you real quick. Do they feel like I got gypped, I could have just done that, or is there like an interesting conversation that unfolds with them?
Paul Ford
It actually turns out that you need a ton of domain knowledge to pull something across the line. There's a reason why 85, 90% of these projects are failing. And the problem is that if I didn't really understand the full web stack top to bottom, I don't think I could build you a platform the way I'm doing now so quickly. Right. So I think what's weird is that we learn this stuff as a set of particular techniques and tools. A web person might learn about different approaches to CSS and CSS frameworks like Tailwind, and people learn in terms of JavaScript, and they learn in terms of TypeScript. There's this body of knowledge that's very associated with specific technologies and that is not necessarily relevant for building and learning now. So I think you have to kind of know that stuff just to understand what you're building today. But the broader architectural understanding is really hard to pick up because everything has been taught in terms of these specific skills and methods and approaches. So I think it's a struggle. The clients, they're coming to us and what they want, they've heard it can be faster and cheaper. That's sort of where they're coming from. Better doesn't even come into the conversation. I'll tell you why. Really big orgs, they can get really great service. They can get Salesforce to stand and sing and dance for them. Small business gets software as a Service. They spend 50 bucks a month or 200 bucks a month, and that's it. Everybody in the middle, which in America gets up to companies that are making $10 billion a year, is actually kind of stuck. They can't get what they need out of the big platforms. They're too big for SaaS. Their margins are tight. And if you hire a CTO, they're going to want a team, and Suddenly you're like $20 million in a hole on tech. And so for them, they're going like, wait a minute, I can finally have this thing. We can get off the spreadsheets. Ethel in accounting won't be the only person who can run payroll. They're excited, but all they've done is pattern match. That AI could get them out of that. Everybody's triangulating and they're triangulating around cost.
Aaron Walter
I keep thinking about ownership lately as I vibe code my way through a million different products and projects and things that I want to make. And recently I'm vibe coding, I'm building some stuff, and my GitHub account is just exploding with all these projects. And I'm looking at the git commits and it's like, has attribution to Claude and it really burns my butter. Like, wait a second. Okay, I know that you're writing this code, but I'm coming up with the ideas here. And I'm curious about this ownership thing in a client services relationship. And I can't help but think, because I have a background in painting and drawing, that the art world has already been through this. You take, for example, somebody like Jeff Koons. Listeners, if you don't know who Jeff Koons is, Google it. You will definitely Know Jeff Koons, the balloon dogs, the chrysanthemum puppies.
Eli Woolery
Ceramic Michael Jackson.
Aaron Walter
Yeah, ceramic Michael Jackson. All these different things that he would manufacture, which is he would basically create kind of like a factory and say, I want to make this idea, go make it. But he's the guy with the idea. And of course the layer behind that is Marcel Duchamp and the famous toilet, the R Mutt toilet. And it feels like software is in the rmut moment where we are making the thing. It's a human idea and the software is a participant, but not the originator. How does this sit in a client relationship or even as an individual software maker?
Paul Ford
I come out of journalism and writing and we've been through all of it before. We've been devalued before, right. So it's very strange to be in the industry where everybody was the most valuable human being who ever lived and watch them go through that process. Because one thing I learned as a writer is that your work is very rapidly devalued and you don't fully have control over it a lot of the time. And so like, you have to negotiate where you're going to come down on that. I don't think programmers have ever had that problem, or if they have, they have, but there's just more fluidity for them. And you're right, Claude's name is on most of those commits. Here's what's changing. There's kind of two ways to be a services firm, or there used to be, and one was time and materials and I'll just bill you for time. And the other is delivery based. I will get the thing done and then I will give it to you and you will pay me in installments for getting it done. And they're very different in a funny way. And we were very much always a delivery based shop. Because what time and materials tend to optimize for long term is change orders. We got it done, but it's not quite done. I need you to give me a little more money and so on. And if you turn that around, the delivery base is like, yeah, we might have to cut scope here and there, but I promise you it will be done. So now what's funny is that the promise can be kept if somebody's good with these tools. Not everybody is there yet, but I think they will be like, I think, yeah, maybe only 15% of AI projects are making it over the line, but it'll be 20% and it'll be 30%. It'll get better. And so Delivery is much less risky than it used to be. And I think where this ends up and what I'm finding that people want to buy from us is to have us as an outboard auxiliary product team for the long haul. So I'm going to pay you X dollars a month, and you're going to be in slack with us, and you're going to be using AI, we're going to be using AI, but we're also going to be doing our stuff and shipping our software, and there's going to be bugs and so on, and you're just going to be on the team with us. And I think that that relationship gets really, really fluid because what that does is and what I see people doing, and I think they're getting in trouble this way. They keep trying to use this stuff, the value for themselves or hide what it did so that it looks like it's their work. It's actually an understandable instinct. Like, I don't want you to know how little I did here. I want you just to see and understand that I'm really good at my job. And then when they get caught, it's really, really bad. And I think that's very dangerous. I think you need to disclose when a human did something when it was produced by a process, when it's automated, all of that stuff is actually really important. And I also think the buyer is interested to lean in and have that relationship. So I think that's changing. But it's very early days, even though it feels late.
Eli Woolery
I have a slightly different conundrum than Aaron's, which is I've been using the tools a lot for our illustrations, and I have a little bit of a background in illustration. When I was younger, I did a lot of it. But now we're producing things at such a cadence that I can't spend a week working on an illustration necessarily. And we'd also love to have the budget to hire an illustrator and Art direct them. But it's just me and Aaron. We're still just. Just trying to get to the point where we can solidly support ourselves. So at some point, maybe we get there. But the conundrum I have is I will Art direct something. And for instance, recently we've been doing these illustrations around Stranger Things because we had the Stranger Things writer Paul Dichter on the show recently. And so I'll have, like, Demogorgons in a writing room together or Demogorgon Waiter, that kind of thing. It's fun and interesting, and at the same time, I'm seeing, like, the influences it's pulling from. And at one point, I posted one of These illustrations on LinkedIn, I think, and somebody just wrote Maurice Sendak. And I was like, yeah, I'm pretty sure that it hoovered up all of Maurice Sendak's work. And it's drawing from that to create these things. And there's other illustrators out there who have real big problems with them and hate the tools. And it's understandable, but I'm still at the point, like, I'm creating something. I feel creative, but there is that tension. Like, man, it's just these systems have hoovered up every bit of human creativity and are, like, regurgitating it back at us. So I'm just kind of curious where you sit on that spectrum.
Paul Ford
Oh, don't worry. I have a really easy solution. No, I mean, it's a nightmare. It's an absolute nightmare. You know, I gotta tell you, we have a newsletter. I have a newsletter. Mostly I write it. We dabbled around and we just kind of gave up and went back to stock because it feels off. And it just did feel off. I'm with you. I like playing with these things. And I've been interested in generative digital art for 30 years, and so I see it as a continuation of that. But it slammed into culture so hard, and it slammed into culture with so little context and so few rules attached that it starts to kind of blow up in your face. Like that feeling you're having. To me, that's an early indicator that you probably won't be doing this forever. You'll find some other way to make work, or you'll go to stock or you'll hire somebody or so on, it feels like a stopgap. And if it was a good product that really had clear provenance and you understood what was going on and people were being compensated, you'd probably be all in. I think this is just culture. When the robot makes it and it looks like Maurice Sendak, and it really does, it feels like you're kind of ripping off the estate of Maurice Sendak, and that wasn't your intention. And it's just kind of gross. And you don't want that to be your product. But at the same time, if you don't have a picture, no one will look. And so we're all triangulating through this and trying to figure out what the parameters are. So for me, as a journalist, writer, who's still out there, sometimes it can't touch a word. I won't let it touch A word. But I will let it help me gather links and I will let it make bullet points about those links so that I can go read them and figure out what I think. But I won't let it do that part of the thinking for me, just some of the searching. And then as a coder I'm like, go to town man. Just have a good time. Let's get you some open source libraries to learn from and so on. I'll give you a funny example actually. So I don't know if you guys are familiar with this world, but there's a whole world of they call it Algoraves and there's sort of little computer programming languages that output music instead of code or instead of applications. Now there's one called SonicPy, there's an old one called Csound, and there's a website if you go to. It's just called like Strudel CC. It's like a JavaScript like thing in your browser. But you can write relatively good beats with a little bit of bass behind them. So it's fun. And I had an LLM produce some really sick beats. It was great. And it was doing them in code and you could see the code. And that is so radically different in my head from using Suno to fake music. There's no vocalism, it's just samples chopped up. It's 808 drum machines. It's very familiar. And so you could go do that right now and you could also say, hey Claude, I want you to make me a really cool song using strudel and cut and paste it. And it would play the song and it would sound pretty good. It really, it did sounded pretty good. Nobody cares about that. Nobody's saying, oh boy, you cheated. Because it's kind of music as coding. So the boundaries are very fuzzy. There's lots of counters that you can offer. So I think it's just gonn really painful years and many lost friendships as we figure out what the boundaries are. And it's gonna turn out that we were too willing to dabble. And it's gonna turn out that they're using it all day when they said they never would. We're just headed for it. There's kind of no way to stop it. Cause there's too many humans.
Aaron Walter
You wrote a great piece on Wired called To Own the Read Shakespeare.
Paul Ford
Oh wow. Deep cut. Okay. Yes.
Aaron Walter
Really resonated with me because the crux of this is this kind of back and forth recurring battle from tech bros VC types. Very analytical, kind of leaning towards the developer world fighting and basically posting memes about anyone who studies liberal arts, poetry, people like me study painting and drawing, that the only thing that we can do is clean floors. It's interesting. The premise that you have is that those are the people who will be ascendant in this changing world. Could you walk us through your thinking there?
Paul Ford
You know, it's funny because recently there was an article finance companies having to resort to liberal arts graduates because
Aaron Walter
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Paul Ford
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Episode: Paul Ford: Writer, developer & "fun Cassandra" on why everything is changing (but not how you think)
Date: June 3, 2026
Host: The Curiosity Department (Aaron Walter & Eli Woolery)
Guest: Paul Ford
This episode explores the transformative impact of AI on design, technology, and the creative process. Paul Ford—a multidisciplinary thinker, award-winning writer, developer, and co-founder of Aboard—shares why he positions himself as a "fun Cassandra" about rapidly shifting paradigms in design and software. The conversation dives into the realities of generative AI, ethical dilemmas around ownership, accelerating ideation versus slow execution, and challenges to creative and organizational culture.
On Design’s Core Role:
“We have to get context before this product can get moving. And it’s going to start with mood boards and ideation, but it’s going to end with us sharing a language with the customer … and it’s all of that.”
— Paul Ford (10:41)
On AI’s Acceleration Limits:
“The coding is really fast, but the thinking is actually not that much faster … It’s maybe a little bit faster or possibly a little bit slower because we have so much more product to work through.”
— Paul Ford (09:03)
On Ethical Tension in AI Art:
“When the robot makes it and it looks like Maurice Sendak ... it feels like you’re kind of ripping off the estate of Maurice Sendak, and that wasn’t your intention. And it’s just kind of gross... But at the same time, if you don’t have a picture, no one will look. And so we’re all triangulating through this.”
— Paul Ford (20:31)
On Disclosure & Trust:
“I think that’s very dangerous. I think you need to disclose when a human did something, when it was produced by a process, when it’s automated, all of that stuff is actually really important. And I also think the buyer is interested to lean in and have that relationship.”
— Paul Ford (16:35)
On the Enduring Need for Humans:
“There’s a reason why 85, 90% of these projects are failing. And the problem is that if I didn’t really understand the full web stack top to bottom, I don’t think I could build you a platform the way I’m doing now so quickly.”
— Paul Ford (13:14)
| Timestamp | Key Segment | |:---------:|:---------------------------------------------------------------| | 04:58 | Paul introduces the “fun Cassandra” idea and what it means. | | 07:49 | AI’s impact on ideation speed vs. real-world product-building. | | 10:41 | The necessity of design context and shared language. | | 12:56 | Transparency about AI’s role with clients. | | 15:56 | Discussion of ownership, creative attribution, Koons/Duchamp. | | 16:35 | The imperative of disclosure in AI-generated work. | | 20:31 | Grappling with AI-generated art and the “cultural stopgap.” | | 23:42 | Ford’s case for liberal arts in the AI era. |
Paul Ford brings a mix of wit, humility, and deep concern, delivering his cautionary observations in an engaging, highly informed style. The conversation is frank about the disruptions AI and automation bring, yet is also hopeful about the urgency for maintaining human connection, meaning, and skill—particularly in design, ethics, and creativity. Ultimately, the episode suggests AI won’t eliminate the value of design or creative endeavor, but it will force practitioners to revisit what expertise and partnership really mean, and to navigate new, sometimes uncomfortable boundaries.
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