Chris Lindland on Creativity & Play

Chris Lindland is a creative founder and entrepreneur. He built Betabrand, a crowdsourced fashion company that grew to $300M, launching products like Dress Pant Yoga Pants. Now, he leads OWOW.ai, an AI-driven entertainment platform. An Adweek Top 100 Creative, he focuses on technology, storytelling, and social engagement to drive business success​.

So, I start all of these conversations the same way, which I also do in my practice. I borrowed this question from a friend of mine who helps people tell their stories. It’s a beautiful question—big, though—so I tend to over-explain it. But before I ask it, just know you’re in total control. You can answer or not answer however you like, and it’s impossible to make a mistake. The question is: Where do you come from?

This is exciting. It's like a game. Where do I come from? I’d say I come from California, from my formative years as a kid. And as an adult, at some point, you just have to own up to where you’re from—and it’s California.

What was it like to own up to being from California? What are the challenges associated with that?

It was an interesting thing. I lived in San Francisco for about 20 years, and at some point, I became convinced that’s where I’m from—because it was the place I’d spent the most time. It was my entire adult life. I grew up in San Diego, spent childhood around L.A. and the Bay Area, but I ultimately spent the bulk of my adult life in San Francisco.

So, in many ways, I think that’s where I’m from. But because I’ve spent time broadly across the state, and I love it so much, that’s where I’m from. I don’t live there now, but that’s still where I’m from.

What does it mean to you to be from San Francisco? What happened to you there?

There was this gravitational pull in 1995, mostly through friends from high school who had moved there. I graduated from the University of North Carolina at Chapel Hill, and I didn’t feel like my future was in Carolina at age 21. So, I moved to San Francisco, thinking, "Oh, my friends are here, and they’re smart—we’ll figure it out."

And I did. I stayed there a long, long time.

Growing up in San Diego—what did you want to be when you were a kid?

Oh, you know, I never really thought about that. That’s probably part of why it took me a while to figure out what to do in my 20s. I was really interested in my friends, in getting away and doing stuff. I didn’t spend much time imagining what I’d be—I just enjoyed the people I was with.

And tell me, where are you now? What are you up to these days? Catch us up on where you are and what you’re doing.

Right now, I’m sitting in Chicago visiting my family. But generally, I’ve been living in Europe for the last year and a half—mostly in Paris, which is magnificent.

When I first encountered you—I can’t remember how it happened—but I was a huge fan of Cordarounds. Can you tell me the story of Cordarounds and how it came to be?

Yes. I was one of those people who, like you—and probably your listeners—had a creative need that needed to be satisfied as an adult. At the time, I was working in a business that felt very much like... a business. I wasn’t being as creative as I wanted to be.

So, I invented corduroy pants with horizontal cords, just on a lark. There's a long, complicated backstory I won’t get into, but basically, I knew people who talked a lot about fashion. I thought I’d make a pair for fun. Then I had a pair. Then I found myself single.

And women would commonly grab my leg at the bar and go, “Oh! They go in the other direction!” And I thought, this is marketing gold. I just wanted to—because I had done—well, I’d sold a TV show when I was younger…I had co-founded an internet startup. I’d always been doing creative stuff, but I wanted to do something that felt like a great portfolio piece. I expected to use that project to land a job in advertising or marketing. I assumed it wouldn’t go on very long—maybe three to six months. But it did.

I made corduroy pants that went in the other direction. I made a few hundred pairs and created a website I thought was funny. It was meant to be a portfolio piece, but that journey ended up lasting about 20 years. Technically, it was 17, but it just became the funny story that never ended. That project got me into the clothing industry for a long time.

You mentioned all these various creative projects—I wasn’t aware of the TV show or the startup—but how do you describe what you do? Or even just when you think about yourself, how do you talk about it?

I’d say that the thing that defined my career—particularly the clothing company chapter, but really before that as well—is that I was the person who had the big dumb idea, or fun idea, and it would stick in my head long enough that I’d feel impatient to bring it to life. Big or small.

When I was running Betabrand, that gave me the perfect outlet to do that on a weekly basis. I love sitting around batting ideas back and forth, then figuring out which one we can actually go make. That’s probably the thing I’m best at. I don’t know if I’m world-class at it, but I’ve spent a lot of cycles doing just that.

From Cordarounds—I was really a superfan—they always had entertainment baked in. They were fun, playful, novel, and totally unique. Betabrand ended up being a real pioneer. How do you think about the role Betabrand played? And of course, I want to talk about what you’re doing with AI, because it seems like you're once again at the front edge of tech or media. Is that how you think about it?

Let me go back to Cordarounds, because there are some values that came out of that which might help explain how I think or give your listeners some insight. When I started it, my intent was to create a website I knew was funny—mainly for my friends, people I thought were funny, so we could all have a laugh.

The site focused on the pseudoscience of horizontal corduroy: how it could improve your aerodynamics, reduce your crotch heat index by lowering leg friction. The motto of the company was, “An evil multinational corporation has to start somewhere. For now, pants.”

The whole thing was a joke. It had the attitude of Halliburton while being as small as a mom-and-pop store. The thought was: all these giant companies we see on skylines started small. Why not us?

“We” was me and my friend Enrique Landa—an incredible thinker and a blast to work with. He was also on board with the idea of going all-in with bombast and glory, fully expecting it would just be a website nobody visited. That would be that.

But because of the intentional stupidity of that site—and this was in 2005, mind you, when there really weren’t any digital-native brands—we were either the first or among the first to create an interesting web experience and sell directly to people. Like a catalog. We’d find people online, they’d shop, and we’d ship.

The whole idea was to create stories that lived in the pants. I gave people jokes to tell when someone asked about them. I’d already come up with every dumb line you could say about those pants, so I felt like I was feeding people small talk.

That became the core thesis of the company: make products with charm that spark conversation, and give customers a little backstory, some lore, or a silly factoid they could share. It turned out to be a great word-of-mouth marketing strategy. And because we put so much thought into each product, they ended up getting a lot of press.

I think you found it because New York Times Sunday Styles did a story on it. Peter, I think it was three months in when we struck PR gold—really quickly. That led to more and more stories.

To keep up with that momentum, I kept inventing new products. It proved to be incredibly fortunate—either very lucky or maybe very good—that we kept it going. That eventually grew into the company Betabrand, which became a kind of product-generation experience for people. We were creating and launching new products every day.

Unbelievable. Thinking back to that time—just to put it in context—a lot of my listeners or newsletter subscribers work in consumer research. We help companies, big and small, understand what’s happening in culture so they can stay relevant and resonate with people. We think about brands and culture in big, abstract ways. But you were effortlessly creating conversational, culturally relevant products back in 2005. I seem to remember the executive hoodie—wasn’t that one of them? It arrived just as Zuckerberg was getting attention for wearing hoodies. What were some of your other PR hits? How conscious were you of building products for culture, for conversation? Was it intentional? Where did that come from?

No, that was the whole point. We would start by figuring out whether there was a hook to a concept. Then we’d build a story around that idea and shape a product to match it. The products themselves were pants, jackets, shirts, sweaters, bags, shoes—ultimately, Betabrand made around 2,000 products. So it ended up being a lot.

But in the beginning, it was really about coming up with enough small talk for a product, or creating an experience that could carry a conversation—and then building the product to meet that moment.

Here’s an example I think came up when we talked the other day. I figured, if we’re going to have a holiday product, well—there’s a black sheep in every family. So why not make sweaters out of black wool only?

We figured out how to source only the black wool from black sheep, so the black sheep in the family could wear sweaters made from black sheep’s wool. It was a perfect gift idea. Everyone either is the black sheep, thinks they are, or knows who it is.

At the time, I was running the clothing company out of my basement. But once again, I had come up with a product people loved to write about and share. Amazingly, through Betabrand, I became the largest importer of black sheep’s wool from New Zealand. I was the largest consumer of black sheep wool in the world. That became one of those strange but fun achievements.

And again, it worked because there was an elaborate story. If there’s a black sheep in every family, now there’s something tailor-made for them. We repeated that process over and over with many different products. We loved it. We created small cults around each one. We were also very conscious about getting people to participate in the story behind an article of clothing.

That brings us back to the Zuckerberg hoodie, which was a good example. I saw that news story coming. I knew Facebook was going to have an IPO, and I figured, if we made a hoodie out of suit cloth and released it at the right time, we could ride the wave. The result was what PR people call newsjacking—inserting yourself into a bigger news story. And we did. We successfully made the official fashion story of the Facebook IPO. Our executive hoodies were covered all over the world leading up to the event.

All the venture capitalists who were about to profit immensely from the IPO were banging down our door to get one to give to Mark Zuckerberg. There were something like 30 unique requests to send it to him as a gift. We knew the IPO was going to be a generational event, and we found a way to insert ourselves into it.

I got really good at that. We would look ahead, see what news stories were coming, and then shape products around them. At the time, we referred to Betabrand as fashion’s first responder. We’d be the first business to respond to something that had just hit the internet—and we’d make a product around it.

Unbelievable. That’s so amazing. When you say “build,” can you say more about building a cult around a product? What lessons did you learn? I guess the underlying question is: does that playbook still resonate? I know you’ve moved on, and we’ll talk about that in a bit, but at what point does this playbook still apply? I mean, the principles seem like they would hold up, but I’m curious what you learned, and how things may have changed—if at all.

Well, I remain convinced that it still works. You can see examples of people who’ve done it even better since then.

Take Gymshark, for instance. They were incredibly smart. They found Instagram addicts who were also doing what you could call death-defying stunts in gyms. They had those people help define what it meant to be a Gymshark. As a result, the brand became this perfect cult, where the users got to define the rules and shape the identity—and an entire culture formed around that.

So yes, absolutely, I’d love the opportunity to find a cult and build something around it again. The way Betabrand worked, we didn’t always know which cults would find their way into our clothing. But we made a point to tell their stories as well as we could when they did. The origins of these ideas are often strange. I’m sure you’ve experienced that, and your listeners too. In one case, my friend Enrique and I went down to L.A. to check out a fabric shop we’d heard was huge.

We were just browsing, as usual—we’d often make funny samples for ourselves since we had access to manufacturing and could make custom clothes whenever we wanted. He found this fabric—silver lamé tiles that reflected light like a disco ball.

When we brought it back to our shop in San Francisco, it was the end of the day and light was beaming through the windows. They held up the pants made from this fabric, and the light bounced off them just like a disco ball. It cast light all around the sewing shop. It was beautiful.

We were laughing out loud when we saw them because we knew he had just created a masterpiece. As he wore the pants around, it had that same effect—people stopping him, saying, “Oh my God, where on earth did you get those? Please, where can I get some?”

But the funny part was, we only found about eight yards of the fabric. So we held a little contest. We made a few pairs for people who sent in the best pictures of themselves wearing Cordarounds. Then it got down to just three square feet of that fabric.

We treated it like cavemen carrying around an ember—clinging to the hope that one day we’d find more. It took years—three or four—before we finally found a supplier who could reproduce it.

When we did, we created the fabric and launched Disco Pants. And what was wonderful about them was that the cults found us. There were groups of people who really claimed those pants as part of their identity. One of them was BASE jumpers. I became, somehow, the Ralph Lauren of the BASE jumping community.

These folks were already filming everything with GoPro headsets, so they sent us the most unbelievable action sports footage. We’d cut it all together into these beautiful, crowdsourced videos. That insight—that the product worked because the customers were already filming themselves—was key. We asked ourselves, “Who else wears GoPros?” Then we got the disco fabric on them, too.

We found all sorts of lesser-known extreme sports folks—people who would never imagine having a sponsor—and we gave them disco by the thousands. For years, we received this endless stream of incredible footage. Another group that found us was Burning Man. I’ve never been to Burning Man, but every August, people started coming into the Betabrand store in droves as they passed through San Francisco on their way.

At one point, my friends started telling me, “You really need to go to Burning Man, Chris—because everywhere you look, people are wearing your clothing.” Thousands of people were incorporating our disco pieces into their costumes. When a cult finds you, that’s the best thing that can happen. Then you can sit back and tell their story.

Anyway, long-winded—but I loved that. I really did. Just this week, I found out that one of our BASE jumpers passed away. It hit me. I didn’t know him personally, but I’d seen this video—he says something right before he jumps off a cliff. It became a sort of tagline for the whole group.

It was sad, because you admire that kind of bravery. People who throw themselves off cliffs all over the world often form really tight bonds with each other.

In a way, I felt grateful that he’d gone this long, continuing in that life. He probably spent 15 years in that sport. The amount of adrenaline he experienced in that time is legendary. That’s amazing. I wasn’t aware of that story.

What do you love about that work? Where does the joy come from in all of it?

You know, I think I was telling you the other day—early on, when I was running Cordarounds, people would reach out to me. Names I started to recognize. They became repeat customers.

To me, that was magic. When we made those first products and I started seeing names on the orders that I didn’t recognize—names that weren’t relatives or old friends—there was this moment. That feeling when your creative experiment connects with people out in the world, with other creative people you’ve never met, it’s just really, really special.

I remembered your name. I remembered so many of the names of people who were into it. It was truly exciting. When you’re a creative person and you invent something, and then someone connects with it—it’s a thrill. Suddenly, you’re the kind of person who gets lit up by the idea that people out in the world are into what you make.

It’s a really beautiful experience to know that there are talented people out there, and somehow, you’ve made it into their wardrobe, into their imagination. And that feels great—because then you get to meet them, and you get to learn from them.

If you’re ever lucky enough to create something that builds a fan base—which you’ve done with your podcast—the reward often feels even bigger for the creator. Because what you launched, you now get to understand more deeply through the eyes of others. Anyway, long-winded.

No, not at all. We talked the other day, and I was living in Hudson. It was genuinely thrilling to talk to you, because my relationship with those pants and that sweater—it meant something. I had at least two pairs of Cordarounds, and I loved the black sheep sweater.

I didn’t realize there was a family insight built into it, which makes it even richer. But those were the kinds of pieces that hit you—and you just had to have them. What I love is that your product development felt deeply cultural and deeply social. And yet, small talk was like the litmus test. That’s what you used to know whether a product was good. I think that’s unbelievable.

It’s just so wonderful. And beyond all that—they made me feel good. I loved walking around in them. I was dying for someone to ask me about my pants, or to tell them it was a black sheep sweater.

It was really fun. Everyone in the creative field knows that feeling—when you’ve got a good one on your hands. We’re always trying things, and they don’t always work. But when something resonates, it’s so exciting. Another good example: we made yoga pants that women could wear to the office. When we launched our women’s line, that product took off. We sold millions of pairs.

But the idea that really took hold was how we presented it. My concept was that we’d only use models who had PhDs—or were in the process of earning one. That became our thing: the models must have or be pursuing PhDs to appear in our campaigns. It became a global news story. People loved that we were using models who were there for their brains—not just their bodies.

It was incredibly fun. The idea that, if you have a product that resonates with the smartest women in America—and those women are obviously smarter than I am—then their word-of-mouth is going to be more interesting, more thoughtful, more powerful. So we started with the word-of-mouth power of a tight, intelligent community. And because of that, it became a great news story.

We went on to sell millions of pairs. I mentioned that before, but it became the biggest product we ever released. And what made it even better was that it was rooted in something like intelligence—it just happened to be. That gave it this extra dimension, and I really liked that.

What would you say is the legacy of Betabrand? I know you’ve moved on, and we’ll talk about OWOW.ai and your take on generative AI, but how did Betabrand end? Or—did it end? What’s its legacy?

No, no—Betabrand lives on.

I sold it. It’s kind of a funny story. A long, bloody story. The company had grown to be quite large and was growing at a blinding rate in 2019. But by that point, let’s say our top 30 products were all yoga pants you could wear to the office.

And when the world of office workers left the office, well... you can imagine what happened.

Yeah.

It was like trying to sell surfboards when the ocean had frozen over. Extremely difficult. On top of that, we had a unique warehousing and shipping setup based in Hong Kong, which relied on air travel. And when something like 90% of Cathay Pacific flights were canceled, well—it was a perfect storm of collapsed supply and demand.

Eventually, I sold the business. But it still sells dress pant yoga pants by the zillions. That product became so absurdly popular that it overshadowed everything else we made.

I imagine people listening to this have experienced something similar—when one product works so well that all the other stuff that connects more to the soul of the company ends up getting pushed aside. At some point, I had to build a whole new brand identity around that single product.

So yeah, a lot of the fun, quirky products that brought you there—those had to go. Because when one thing is outselling everything else by a factor of 10,000 to 1, there’s a bit of cognitive dissonance in claiming you’re a freaky, Burning Man–inspired, base-jumper experimental clothing lab… and also the go-to source for professional women's officewear.

So we cut that stuff out. And now the company continues as that—the yoga pant company. But what’s sweet is that people still reach out to me—honestly, probably every three weeks—asking if they can get Cordarounds, or Disco Pants, or the Black Sheep Sweater, or one of our old jackets.

Part of me wishes I ran it like a weird, once-a-year clothing drop. Just one day a year where people could get their Cordarounds, and that would be it. I wouldn’t be in the daily grind of the clothing business—just one day of joy.

Amazing. I mean, in hindsight—and maybe this does it a disservice—but it felt like you were running a public lab. You had all these novel products, smaller hits, and then this one massive hit that just swallowed them all.

Yeah, I would say that’s fair. It’s interesting to reflect on this now, 15 years after that original concept was hatched. A lot has happened since then. Some of the claims to fame for Betabrand: Cordarounds was probably the first direct-to-consumer clothing line. Then Betabrand created a huge voting platform. We would post thousands of theoretical clothing designs, and we’d crowdsource the winners. Consumers would vote on which products we should make.

It was this wonderful system that gave our fans something to do—daily, even hourly. If you wanted to help us figure out tomorrow’s product line, you could vote, comment, give feedback. It made you part of the process.

We were trying to think of ways to make a clothing company into something people could visit daily and be part of. The whole idea was: can you create community through clothing? It really was like running an R&D lab.

Another claim to fame—we were the first business to do user-generated content. For years, we encouraged our fans to be the photographers of our clothing. What we did differently was that, instead of just adding customer photos to the bottom of the webpage as a tech add-on, we flipped the script. Customer photos came first.

The message was clear: this is about the community. Get involved. Help create things. Be part of the culture. If you’re really into it, you’ll meet people you like. That was the point.

Betabrand was meant to be exactly that. The name itself was intentional—it stood for a brand of products and people that are always in development. Where did that idea come from? It was kind of in the air at the time. This was late 2000s, early 2010s. You had Kickstarter starting to take off. Crowdsourced and crowd-oriented platforms were just beginning to gain momentum.

Our goal was to become the crowdsourced clothing company—a place where creative people could find an audience and bring their clothing ideas to life. Betabrand would serve as the manufacturer and the storefront.

Honestly, I probably took the first 10,000 photos of Cordarounds and Betabrand pieces myself. So I loved when other people started doing it, partly because it meant I didn’t have to anymore—but also because, by then, we had sold hundreds of thousands of articles of clothing.

With that many customers, chances are you’ll have some incredibly talented photographers and videographers in the mix. And if they want to put their work up, God bless them. Most of the time, they were better than I was. That became part of the culture: fans turning into creators. That was a real thrill for me. I got to sit back and watch creative people do their thing.

Some of our most popular products were invented by customers. Some of the biggest news stories came from ideas that originated with our customers. It was amazing—we let them do the job, and it worked.

I want to tell you a story about that—about the power of letting your customers create. One time, I was sitting at Pepsi. They had invited me to give a speech. I was checking my phone, and I got a message: Good Morning America wants the exclusive on the Suitsy.

My response was, “What’s the Suitsy?” A very creative guy had submitted a concept to our website—a zip-up onesie version of a suit, which he called the Suitsy. He had actually made a sample himself. It was just a post on our site, but within 24 to 48 hours, it went viral. All of a sudden, someone’s idea—just a photo, not even a manufactured garment—was getting global news coverage.

The same thing happened with another concept submitted by a DJ who opens for Paul McCartney. So he knows what it’s like to be famous, right? He wanted to create a retroreflective hoodie using the same kind of material that cyclists wear—fabric that glows brightly in iPhone photos. The idea was that the hoodie would make your face disappear in flash photography, making it perfect for famous people who want to go incognito.

He called it the Anti-Paparazzi Hoodie. That idea became such a popular news story, it was even featured as a question on Jeopardy! I loved being able to attract creative people—people far more inventive than I am—and then fan the flames and help promote their ideas. That was really the big idea behind Betabrand: attract brilliant people to the brand, and then give them a place to bring their ideas to life.

Amazing. So tell me about OWOW.ai. This is still really new, and I’ve had so much fun with it. What’s the story there—what are you up to?

Well, I think we all have our own AI epiphany origin stories at this point. At some moment in the last few years, everyone has created something with AI that made their jaw drop—something that made them go, Oh my God, I need to rewire my brain.

For me, after I sold Betabrand, I needed a full unplugging. I just wanted to zone out and stare at the Pacific Ocean for a while. Try to reset. So I went down to Costa Rica. The plan was to relax, surf, and just enjoy the sun for a few months. I figured that, at some point, I’d reemerge with a big new idea. What I didn’t know was that I had timed it perfectly… for the biggest rainy season in decades.

I’d been there before during rainy seasons, but this was next-level. Literally from day one, torrential storms hit every afternoon—starting around 11:30 a.m. and lasting until 5:00 p.m.

So for four or five days a week, the entire middle of the day was just an absolute deluge. I was stuck inside, which was the last thing I wanted. That was spring 2022—right when Midjourney launched. That’s also when DALL·E came out, and this thing called LION, which I thought was really cool at the time. There was also early stable diffusion stuff starting to emerge.

And because I was bored, I decided to take the deep dive. At first, it was just making me laugh. I was generating these crude, ridiculous images. Back then it was like, “Oh my God, this kind of looks like Bigfoot! It has twelve fingers and a cowboy hat!” And that was funny.

It only took me a minute to generate it. I was just completely charmed. Over those three months, I watched the tools improve—from day one to day ninety—and it really stuck with me.

There was this small, fun community starting to form on Instagram, people posting their creations. I began sharing images with them and learning from their creative process. You could actually see how people were getting better at prompting, how their techniques were evolving.

Then Stable Diffusion came out, and it allowed for these elaborate, recipe-like instructions to generate images. I just kept getting more and more interested. Fast forward a year, and suddenly you’re creating photorealistic images. That’s when I got into face-swapping technology and thought—why not create tomorrow’s entertainment starring us?

I started sharing the idea with a few friends who are investors. They were excited. They said, “We’d love to invest in you if you want to build this.” So we started working on it last November and created a company called OWOW.ai.

The real mission is to explore what’s now possible when you can stitch together all these technologies to let someone experience something that feels completely immersive—like, say, what it’s like to travel to Tuscany, without actually going.

You could see a version of yourself in Tuscany, experiencing it as if it were real. And it’s funny, and weird, and kind of inspiring. Commercially, sure—maybe it makes you want to book a flight. But more importantly, it’s about creating unique experiences that people can inhabit and shape with their own personality. Right now, it’s basically fun, highly curated deepfakes. We’ve built vast libraries of visual experiences that people can drop their faces into.

But the backend is what’s really exciting. We’ve figured out how to piece these systems together to create live experiences. You can broadcast them onto a wall, a TV, anything—and then let people add their faces, in real time. Suddenly they’re whisked into this imaginative world where they get to see themselves inside the story.

And mark my words—whether it’s us or twenty other companies—within a few years, we’re all going to be watching ourselves perform on Netflix. It’ll start with cameos—some charming little novelty. But eventually, it’ll grow into actual entertainment involving us. I’m not saying we’re all going to replace Harrison Ford and play Indiana Jones, but we’ll absolutely be able to be the sidekick—or the comic relief, or the random background character.

There’s going to be an entirely new kind of media when you can generate content that fast. And just for context, for people who aren’t deep into diffusion models like I am—that’s about two and a half years away. Once we hit real-time live video generation, we’ll be there. You’ll be able to create stunning, believable video starring yourself, your friends, your family—even your pets. And it will be affordable.

For me, I just want to work on this now, because it’s amazing to spend full-time playing with these capabilities and bringing them to life every week. It’s magic. Without a doubt, of all the creative things I’ve done, this is the fastest, most mind-blowing creative experience I’ve ever had.

It’s just so much fun. I’ve done a couple of batches myself, and I’m fascinated by the origin story. Maybe I’m overthinking it, but it seems like with Betabrand, the big insight was: we want to talk about the things we wear. If you build community around a product, it means making the product something people want to talk about.

There’s something similar going on here with generative AI or deepfakes. Like you said—with real confidence—we’re going to be watching ourselves. So I’m curious: what makes you so sure of that? What’s the insight? How did you arrive at that conclusion?

Sure. Well, first off, I can’t tell you the exact size of the audience that’s going to enjoy this. But let’s go back to the technology itself. Right now, we can generate a photorealistic image of you—Peter Spear—once per second. And we can drop that image into any creative environment we can dream up. They look real. They feel real. They’re funny, and meaningful, and emotional, depending on the context.

By the end of this year, we’ll be able to generate about three images per second. That’s already happening in labs, and even faster in high-end setups. But for most end-user experiences, it’ll be somewhere between two to five images per second.

By the end of next year, we’ll be pushing thirty images per second. Anyone in video knows that thirty frames per second is the standard for smooth, real-time video. So by 2028, we’re going to be looking at real-time, live video generation—fully photorealistic, and affordable.

You’ll be able to create a thirty-second video for five cents. Maybe it’s fifteen cents, maybe it’s fifty—but it’ll be cheap. So if all of that is possible—and it is—then I believe we’re going to see some incredibly interesting new forms of media emerge from it.

I think it’s going to be interactive. It’s going to involve us. Now, I can’t promise that everyone’s going to prefer seeing themselves in The Godfather over the original actors. But if media can be generated specifically to entertain you—to make you laugh or you buy something based on your interests and identity—that’s going to be a much more compelling experience.

Obviously, we’re building a business around this vision, so we’re hoping that this is the future we’re staring at. But the capability is already here. Right now, if we were plugged into Facebook, we could pump out custom static image ads featuring anyone who ever engaged with an ad. That’s already possible. But our approach is to enter this space through entertainment. We want to make stuff that’s truly fun. That’s how we’re finding our way in.

We’ve done this at big tech trade shows. We entertain people daily with this kind of stuff—but really, that’s just the first step. The first capability we focused on was simple: can we make Peter laugh at a picture of himself in a scenario we’ve cooked up?

For anyone listening, last year that meant three of us generating thousands—probably hundreds of thousands—of images just to find the ones where Peter didn’t have seven fingers. Or where people didn’t have a third arm sticking out of their chest. It was raw. We had to be very selective.

But now, the tech has progressed to a point where we can reliably prompt images with a high success rate. We're talking high 90s—in terms of accuracy—for generating an image that includes Peter’s face and looks good. That’s huge. It took just a year to get there.

So if you project forward another year, we’ll be generating images that include the exact glasses you’re wearing. You’ll be able to see the pores on your nose. That’s the level of photorealism we’re heading toward.

With that capability—and if brands are genuinely interested in creating experiences that people inhabit—then logically, they’ll want people to inhabit their brands using this new technology.

And the holy grail of personalization? It’s you.

So I do think some percentage of marketing will go in this direction. We’d be a stupendously successful company if just 10% of marketing became this personalized. If we owned even 1% of that space—with experiences that are truly immersive and compelling—we’d have a very strong business.

But beyond that, from a creative perspective, this is exactly what I want to be working on right now. The change ahead is going to be bananas, and it’s incredibly fun to be in it.

There are a couple of things bouncing around in my brain. You started out talking about people taking pictures of themselves—and it reminded me of something. Years ago, I was traveling abroad, a bit naively, and I visited some major tourist sites. I went to Egypt, saw the pyramids and the Sphinx.

I was excited to take a good picture of the monuments—but what I didn’t expect was how overrun it was with tourists. You had to wait in line to take your photo, and people were obsessed with getting a picture of themselves in front of these landmarks.

It got me thinking: this need for visual proof that you were there. I ended up taking an entire series of photos of people taking pictures of themselves—because I became fascinated by it. And so hearing what you’re saying, it just resonates. Of course we’d want to see ourselves—especially if given the opportunity to see ourselves in places other than where we are. That instinct is already there.

There’s definitely a powerful force of vanity behind it. But what we’ve found is that the most popular use of what we’re doing right now isn’t people making pictures of themselves—it’s making pictures of their friends or family and sending them.

Even better: dropping them into group texts. That’s where a lot of the magic happens. It becomes a fun icebreaker. People can be self-critical about how they look in photos, but when the image is being shared among close friends, in a playful way, they’re far less self-conscious. It becomes a shared laugh. It’s light, it’s personal, and it’s fun.

There’s definitely been this weird value shift—especially through Instagram—where people must officially see themselves in certain places. They’ll wait in long lines just to do that.

And I get it. It’s a moment in your life you want to capture and share. That’s perfectly fine. I don’t look down on people who do it—I just think it’s a fascinating commentary on how visual media works now. What matters most isn't necessarily the masterpiece; it’s the likes you’ll get on a photo of yourself standing 50 feet in front of the clock face. That’s the image that matters.

It’s nuts.

Yeah, it is nuts. But also amazing. I always like to be careful with this kind of thing. I don’t think it’s “crazy” as in something’s wrong with people. I know some people might see it that way, and they’re entitled to that opinion. But I just find it more amazing than anything else—that there’s this completely different experience that matters a lot to people. And there’s a lot to be learned from that.

I really appreciate that corrective, because I’m often that person—marveling at what we do as a species out in the world. My experience in Cairo was a lot like that. I was a solo traveler immersed in group tourist culture. I did a cruise down the Nile, and at every stop, people were lining up, waiting to have their picture taken in front of some ancient relic. Sometimes leaning on it It was such a funny phenomenon.

I’m glad to know that even back in the '90s, it was kind of like that. I hitchhiked from Cairo to Germany—that’s a longer story for another time—but down in Luxor, my friend and I were goofing around, and I wrapped him in toilet paper like a mummy.

He became the unofficial mascot for about 50 tourists who all wanted photos with “the mummy.” Stuff like that would’ve been Instagram gold today. But back then, it was just 35mm film, shared with a few friends: “Hey, here’s me with a guy dressed as a mummy in Luxor.” Anyway. It would’ve been perfect for the internet—if the internet had worked the way it does now.

We’re almost out of time, but I’d love to hear some final thoughts from you. What are your observations or lessons from working with generative AI? You’ve described OWOW.ai as your way into it—maybe not even the final form of what you’ll do. What are you looking forward to?

There’s no doubt about it: this is God’s supercomputer, and now we all get to play with it. That’s how I think of it. Some of my thoughts lately come from conversations with close friends I’ve known for years—people who are also entrepreneurs or deeply engaged in creative work.

One of my friends is a doctor, and she’s working on a concept around patient education. Each of us is focused really narrowly on the projects we’re building, so we’re becoming experts in specific slices of this world. In my case, it’s face morphing, generative speed, and how to use those tools to help people feel experiences. And that’s wonderful—but it’s limited.

There’s kind of a shared consensus among all of us: we should be practicing new skills every single Friday. Period. It’s the only way to even begin to grasp the full scope of what this technology can do. That’s how big of a deal this is.

And this isn’t hype. It’s not overblown. It’s real. I mean, if I can make my friends laugh with a high-quality video that would have taken nine months to make just a few years ago—and now I can do it in nine seconds? Come on. That’s not just faster—that’s a fundamentally different way of creating and communicating. Okay, nine seconds is a bit of an exaggeration, but my friend Tyler is a perfect example. He’s a super creative guy, great at video production. Now he makes hilarious AI-generated videos while he’s sitting on the can.

And they’re excellent. As a filmmaker in his previous life, he would’ve had to spend a ton of money and time to make those same things. But now we can all create music, videos, whatever—and sure, it might not have the laser focus of a trained artisan, but that’s okay. You might find that your love of music translates into fun little songs that entertain your friends and family. And if that’s what you use it for, you’re not a thief—you’re a creator. You’re just performing for a small audience.

I still can’t believe what we can do now. That sense of awe—it gets reinforced for me every week. And I’d really encourage anyone who hasn’t already guzzled the Kool-Aid to consider pouring themselves a little more. Because quarter by quarter, this stuff gets faster, better, cooler, more fun. And it’s going to completely reshape marketing, creativity, and entertainment in a very, very short amount of time.

Where would you suggest someone start? Like, I hear you talking about experimenting—but what’s a good first step?

Honestly, most people already have access to ChatGPT. I’d say: start there. Begin by uploading a photo of yourself. Start playing around. Ask it to be iterative. “Put a top hat on me.” “Add a parrot to my shoulder.” You’ll be surprised at how responsive it is.

Right now, those images take about 10 to 15 seconds to generate. It’s not instant—but just wait. In a couple years, it will be lightning-fast. That’s an easy way in. A fun way in. ChatGPT—especially with image generation—can blow your mind, even as a beginner.

And if you don’t know what to ask, there are great videos and forums out there where people share tricks, tips, and cool things you can do. It’s really fun to explore other people’s ideas. You get to see how they think—and how the machine responds. It helps spark your own ideas.

It’s one of those classic things: the more you play with it, the more ideas you get when you aren’t using it. Then suddenly, you’re racing back to it with something new to try. I’d just say: make sure you’re playing with it. Because play is absolutely the fastest path to the important insights.

Go be immature with it. Go be stupid. Do stuff that makes your friends laugh. That’s how you start to learn how to use it in smart ways.

Awesome. Thank you so much for accepting my invitation. It’s been really great to connect with you—and thank you for Cordarounds, the Black Sheep Sweater, everything you created with Betabrand… and now OWOW.ai too. It’s just so great to see someone so clearly having fun while doing fascinating work.

For the benefit of the listeners, it’s OWOW.ai—that’s O-W-O-W dot A-I. Go check it out. And if you have any questions, you can reach Chris directly at chris@owow.ai. We work with companies, events, developers—anyone doing creative things. So if it interests you, drop me a line.

Beautiful. Thank you so much, Chris.

Great talking to you today, Peter.

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