In this conversational interview, Daniel and Sam explore the emerging archetype of "first of kind" designer founders—individuals who are the first to apply design thinking to new technological frontiers and thus must create their own playbooks. They discuss why this group is distinct, noting a historical risk‑aversion among designers that can be mitigated by visible role models and concrete examples. The pair reflect on how a video‑series format became the chosen vehicle to surface these stories, allowing each interview to feel like a unique medium while collectively expanding the narrative around designer entrepreneurship. Throughout the dialogue they reference several pioneering designers—Henry Modiset, Julie (a former Facebook designer), Susan Care, Colin Dunn, Nicholas Jeff, among others—highlighting their motivations, the importance of ownership, trust, and accountability, and how modern tools such as AI are lowering barriers to entry. The conversation underscores the need for permission‑granting narratives, the value of sharing textured, real‑time learning, and the potential for these stories to inspire a broader, more diverse cohort of designer founders.
Chapters
I was really.
You.
You completely locked in. You should do more of these.
Thank you. Seriously, do you want to develop a show with us? Oh, do I want to what? Develop a show with us.
What would it be?
What would it be? Talking to designers. I'd love to talk to designers, dude. Yes. There are very original and unique stories.
I mean, that's why it's been so fun to do this with you, is because a lot of these aren't out there. So hopefully we get the opportunity to expose them to a bigger, wider audience.
Demystifying. What I think are these. I've been using the term first of a kind, where they are the first to kind of dabble in the space, make something new, but also have to kind of, like, drum up a new playbook.
Why do you think it's a new playbook?
Because nobody had done it before. The technology has emerged. It's kind of happening in real time.
They kind of crack. Put a crack in the dam for this kind of founder.
And I think it's a pretty provocative idea. Idea to put into a bottle and have as a record.
I'm curious for you, now that it's, you know, the YC call for designer founders out there, there's a lot of chatter now about designer founders. What was the seed for you? Or do you remember going back and thinking like, oh, this is the archetype, and whether it was an individual, whether it was a company, whether it was a technology, was there some kind of unlock for you where you started to identify this as an investable type of founder?
I think it's a confluence of things. It's a set of folks who have achieved a degree of seniority, have gotten their tours of duty at startups, and now are seeing more examples out in the wild of people doing this successfully. When you have an Ivan at Notion, a Kari at Linear, when you have a Brian Teske stand at a design conference and insist the world needs more designers, that's a different sort of galvanizing force than the five years preceding. But on top of that, I think the tools are legitimately allowing for people to start to explore and expand their capabilities as practitioners. People are looking for permission to act. I feel like sometimes people lose sight of what they're capable of because they're so focused on what they're doing today. And we can all fall into our own patterns. Right of work. And so if a seismic change happens, we can either put our heads down and stick with the work that we know, or we can use it as an opportunity to take A step back and say, well, this seismic change is happening. All of it feels like a jump ball. That's maybe an opportunity for me to try something different.
I know we talked first in the meadow or in the forest.
The redwood grove.
The redwood grove. One of the personality traits that you highlighted for me, which I hadn't really thought that much about, was the designers as a species were risk averse.
Yeah.
And so I wonder if part of why that needs to be said and why someone needs permission is because innately there's some degree of risk aversion from the new.
There's almost like a risk aversion to the unknown. And new technologies and new examples out there in the world reduce that risk. It makes things more tangible. It requires less imagination. And now you have more working examples to draw from. You're not starting with a clean slate. You're starting with a mood board. You're starting with an idea, a presence, a brand, a figure, talking points, examples, stories. What I appreciate with this whole exercise has been your enthusiasm around giving people the chance to just tell that story, give it texture. Give texture to the designer. Founder journey to the designer who doesn't have a relic or playbook or, you know, a thought piece online to help inspire their actions, but instead is working from an intuition and a sense of like, oh, this is maybe the time for this thing to exist, or, what if I try this out? What if I move in this direction and let's just see what happens. It's not coming from a place of necessarily having like 20, 25 years of experience that earns you the right to make something or to put something out in the world, but instead, the only obstacle, the only threshold to cross, is one's lack of courage or, like, lack of impetus to just try something new, even if it fails completely in the.
Redwood forest is where this kind of took root in terms of an idea. I know we didn't capture all of it on camera, but when the camera's cut, my impression was that you really are onto something with highlighting these new Personas and this new archetype of a founder. And so, you know, with Indy, we are so driven by the idea of fewer constraints, more independence, more ability to pursue what's uniquely you in doing that. It felt like there was a whole new category of founders to project that message onto and give them permission in many respects. And we iterated on different formats for how to do that, but the one we landed on was this video series. So I'm curious, from your standpoint, you know, why this Felt like the right format. Did you get out of it what you'd hope to get out of it?
Yeah. It was surprising to sort of see how in spite of it being one format, it felt like six different formats, six different venues, six different subjects. The vibe of each conversation was as much a reflection of who we were talking to as where we were talking to them. To me, it also illuminated how starkly different each person was, how their approach to technology and to designing. You know, I sort of drew a circle around them, but I realized, like how big that circle was and how.
Many more people were. I was blown away by that. I mean, genuinely. So much of startup content is like pretty cookie cutter. You kind of, kind of know what you're going to get with different Personas. This one, every single one of those is a discrete delivery vehicle for information and experience totally unique to that individual. I thought it was so cool how that comes through.
Yeah. And my hope is that it then kind of creates not only space for additional voices to ultimately come forward and share those stories, but I think it also kind of broadens the archetype a little bit totally. And how one can apply oneself as a first of a kind designer, as somebody to be the first to try some commentatorial new weird space that hasn't done before. And that you don't need the permission of somebody having come before you to act on this intuition and to act on the circumstances immediately in front of you. The thing that struck me was how. How each conversation felt like a moment in time. And that I came away from every convo feeling that much more bullish about the individual, that they had more in front of them, that they were an active participant rather than a passive participant. And I found it more inspiring than I was expecting to, because you get a chance to build relationships over your career and realize that every person is on an individual journey. And some of those journeys are bursty. But each of us has legs to run. We have room to be able to contribute in new and surprising and startling ways. Didn't have plans before our conversation out at the redwood grove to stand in front of a camera and talk to folks. Right. That was not remotely of any interest to me. But I realized that those conversations that I find most invigorating are often just trapped between a coffee date or a catch up or a lunch. And that sometimes in those conversations, when I invite a third party or when I reflect back on it, it's like there's a turn of phrase, a kernel of an idea that's much bigger than that one conversation. And so maybe we should start to encapsulate that and find a way for that idea to grow elsewhere and in places far afield from where we are. And so that's. That's. That was sort of like the genesis of the whole idea. And I appreciate that you kept at it. You're like, if you want to do this, we can do this. Like, I can remove the obstacles. Like, are you gonna talk about it or are you gonna be about it? And I really felt like that's definitely.
One of our phrases.
What I appreciated was, like, your awareness of your subject, of who you're talking to. I appreciate that you. Yeah. You knew how to motivate me to act well.
I was so impressed with how quickly you came up the learning curve too. I mean, the energy with which you put into becoming the best possible person to pull these stories out of people. I think you. To me, at least, what I saw was someone who was taking that stewardship, responsibility, whatever it is, pretty seriously. Maybe we should go through each of the interviews.
Yeah, yeah, yeah.
And talk about why they fit that mold of first of a kind of Henry Modiset.
Henry Modiset.
When you deconstruct that a little bit, you don't end up describing how, like, most companies do management. And so, like, what the hell is up with that? These, like, maybe three things that matter. There's ownership, trust, and accountability. The best designers, they want to get hard problems, they want to own them, and they want to be trusted to figure it out, and they want to be held accountable to impact.
Colin Dunn was a designer who, to me, was constantly circling around the startup journey for himself.
For me, it was always about the right. Finding the right problem. I was patient, I waited. And when I was working at Universe, I noticed that some of the designers on my team were using AI in their work. And that was the first clue to me that, oh, there's something here.
Jessica Hisch, I mean, her work is so distinct, so prolific.
Always putting out that, like, I'm just happy to be here vibe. I just want everybody to be happy. I want you to walk away and be stoked. I want you to feel like you're a better person at the end of it.
Yeah, yeah, yeah, yeah, yeah. So Julie, first of a kind in so many different ways. You know, she and I grew up together at Facebook.
I think I've always wanted to start a company, and I think I had a lot of respect for the people who went out and made something out of nothing. I found that very brave I found that very courageous and try and work at a place like that. That's how I ended up joining Facebook. But it was still in my mind that like, I would want to do that one day. I think if I could have done it earlier, I would have. But I. I think I was just too scared. I was too scared because I didn't think I knew that I could do it.
Nicholas Jeff he is first of a kind in so many ways. You know, material design launches Byline Nicholas Jykov it's like spotting like Bigfoot in the forest. It's like there he is.
In general, like any other companies that I've been to that are like willing to establish pathfinding teams, kind of did so with a similar mindset of like, design is important, but it's important in an ambiguous future looking way that you have to kind of take a risk to staff people working on it that way.
Susan Care is maybe the first.
This was the one where I felt like you were like actually nervous.
Yeah, I think I was nervous because she is a living icon in so many different ways is the person you want to. Want to be. You want to have that degree of influence over an industry.
After Apple, I just felt as if I would never have thought of myself that I might find job happiness at a Fortune 500 manufacturing company. Just wouldn't have, wouldn't have dawned on me. After Apple, I followed Steve Jobs to next. He said, why would you want to twiddle bits for the rest of your life and never make more than $20,000 when you could be the creative director of a Fortune 500 company?
After the first conversation with Henry, I realized actually the reason why that conversation worked was because I was learning something new in real time. And if I can just do that every single time, then I think overall the conversation would have gone in a good place. And that turned out to be the case for all six. So thank you.
Well, you're welcome. But I mean, you made it. You made this experience and you ran with it in ways that are uniquely you too, which I was really happy to show up.
What are we gonna call this thing, Daniel? What are you calling this thing, Sam?
