Cults & Culture with Soleio

Yeah, this week's was a fun one. I have only known Soleio over the Internet. One of the first design hires of Facebook, design leader at Dropbox. We also get into his experience as an investor. He's kind of lived multiple lives as both an angel investor and then starting a firm and then going back to being an angel investor. And some of the investments he's led have just been epic. All time companies from Figma and Vercel and Banta to Replit and Perplexity. He has his finger on the pulse of design forward. Founders can kind of see and understand their DNA in ways that were really interesting to me in terms of risk aversions, blind spots and in many respects what makes a great Design forward founder kind of sets him up and sets him apart from so many angels where he has like a very specific focus on the type of company and the kind of founder he likes to back. And as you look at his portfolio, if you look at his backstory, it all pairs up, you know, in this conversation we cover all of that and more. Excited that we finally got the chance to meet, to have this conversation and ultimately to share with you all. So I hope you enjoy this conversation with Soleo Cuervo.

I read somewhere that the things that really bug us, the things that anger us, is almost like diametrically opposite of what we value.

Have you found that to be the case?

Absolutely.

Okay.

Yeah. Where clutter. I like things that are orderly. I like being a trim little boat in the world. Just simple.

A trim little boat in the world. Yeah, it's a great metaphor. I've never.

It's like two trim little boats too small to clutter up.

Does that show up in other parts of your life? The trim little boat metaphor? We don't know each other, but I've watched your arc. Yeah, we were talking on the way down because I don't know you as the Facebook designer. I know you as the investor.

Interesting.

And so that's where. That's my point of reference for you. So as I've kind of. Yeah, I went back and I listened to a bunch of stuff you've done and we've followed each other for a while on Twitter and gone back and forth. I really enjoy your perspective, but your investing looks like it was a. You say trim little boat, then it got a little bit bigger. From the outside looking in, it was like this studio. It was a space, it was maybe a consultancy, but it had a fund attached to it.

All of the above, it was a happy meal.

What wasn't Right about that configuration for.

You, it was a lesson that I still have to relearn. Simple beats clever every time. It was too clever. So the genesis of Combine was a series of conversations I had with my then partner, Adam McKella. And we wanted to explore the hybridization of a venture firm in a design studio.

Was there a model you were trying to emulate that was doing it in a different capacity but not in design? No, no.

It more or less like it was accelerator esque, but along a very particular vector, which is how do you equip startups with design capacity by default rather than maybe one of the founders is a designer? Not in a lot of cases. They've never even hired for design. And so if you are building your dream home and you're looking for an architect, it's helpful to have a friend who's an architect just to help you understand and navigate the world and know what questions to ask to even just not just to ask candidate architects, but to ask yourself, like, what is it that I actually need and want? How much am I designing? We thought that by exploring the hybridization of a venture firm and a design studio, we could perhaps materially increase our ownership stake in the businesses we back, increase our likelihood of success and build a unique sort of business. Something that would be novel and new. A Happy Meal, the big learning. And let me know, are we recording?

This is how it works. This is exactly how it works.

So the basic idea there with this hybridized design studio is could we potentially offer founders a Happy Meal and solve a lot of problems simultaneously? Initial financing.

So you would be the first check. That was the idea.

It would be very early and we would have enough funds to be able to even.

Because up to that point you were just investing off your own balance sheet. You were an angel investor.

And to be honest with you, one of the things that served as a prototype for Combine was the work that I did with Dropbox and Figma. My first interactions with Dropbox were by way of all these conversations that came from my time after Facebook. Six years at Facebook, we built an incredible design culture. We had probably the best design team in tech. When I left, all of these startups needed help with just that basic question. It's like, how do I hire a designer who's half as good as your summer intern? I don't know how to source, I don't know what to look for.

And it was all on the hiring front. It was like, help me that you can find the talent.

This is predominantly on the talent front. Some of the fastest growing startups were acutely feeling this problem. Enter Dropbox. Two friends of mine, I started this business called Cove. They had ended up selling it to Dropbox and they were sort of drinking from the fire hose of need on the design front. They had, I think, two or three designers on staff and they're like Soleil. Can you help Dropbox in the way that you were helping me?

Dropbox was not small at this point.

No, no, no, it was definitely not. This was early 2012 robots.

But we're talking hundreds of employees.

Hundreds or maybe a thousand. No, no, no, it was not that big. It was just over 100 employees. But there was. The bulk of the company were engineers. They had very lofty aspirations and incredibly growing business. Their product roadmap was extraordinary in terms of its ambition. But they had two to three designers. It's like, who's going to design all this stuff?

Did they have design leadership? Did they have design language?

I mean, they had an early design team. Okay, no design leadership.

I mean, my sense was that back then design leadership was still kind of an emerging field.

Correct. I would agree with that statement. Dropbox was unique in that it was one of the most successful prosumer consumer businesses that was touching not just one device in the manner that, say, Facebook found its success in desktop, web. Dropbox needed to work on Android, on iPad, on PC, desktops, Macintosh. So it was working in the background, but it had a lot more surface area than meets the eye. And all these surfaces had to work in concert, not merely within an ecosystem supported by Dropbox, but for hypothetical new devices. If Google launched a smartwatch, how would Dropbox work in that context? So it was a very different stripe of designer than the kind that we hired at Facebook. I discovered that by working more closely with startups, not only could you deploy capital into them, but you could also ask for advisory shares. As a case study, Dropbox was important because it was more than just like, write a check, send me updates. It was one day a week.

And was it intentional when you wrote that first check into Dropbox? Okay, you said investment advisor.

The same chart that they showed at IPO with these stacked cohorts, 4% of signups convert into paying customers was the one that they showed me in 2012. I'm like, I love this. What a beautiful business. Right? It's magical.

Seemed so. Not opposite, but like a completely different business than Facebook than the one you were raised in.

And not only a different business, it was a dramatically different culture, I think.

So how did you contrast it back.

Then it felt like being a foreigner in a foreign country that you admire.

Yeah.

Imagine living in Japan for two years.

Yeah, right. Don't speak the language.

You appreciate all the niceties. You share certain common qualities. In the process of being there, you realize, oh, this startup has been around.

And successful for four years without me.

A lot of its DNA is pretty well baked. And I think the context there is kind of important because they were the front runners. They were the category defying business.

Sure.

Facebook, we were the insurgents. We were building product in an era where people thought, why bother? There's already a winner in this Space. It's called MySpace. They've got 12 times more users than you guys. And the thing that people overlook is it took us like five years at Facebook to run down MySpace in terms of like Maus. Yeah, I remember April 2009. Yeah, April 2009. Right. We didn't get that for free. And so, you know, we were a hyper competitive, hungry, almost paranoid culture. Move fast and break things meant something on Facebook. You go to Dropbox, they don't want to hear about move fast and break things. Why? Because its success as a business came from its stability, its reliability. I remember Drew Houston would have this onboarding talk and they would. He would often describe Dropbox as like space shuttle quality software that would sit on your computer. Right.

And space shuttle quality, that was like, no failure rate.

This thing has to be so has to be the most reliable thing on the planet to you because you are essentially entering an agreement to put your most precious belongings, your data, into this service. You don't want to ever second guess it. Right. You want to feel the assurance that I can toss my laptop into the ocean and all my stuff is safe in Dropbox. And that was sort of the promise that was made. Every successful startup culture develops a lore right. Through its earliest successes.

What was the lure of Facebook News Feed?

Yeah, because Newsfeed was, I think, the first time the company showed its larger aspirations. Somebody once called it our Death Star moment. And I love the analogy. If you set aside the negative connotations. Right.

I saw some interview where someone was pressing you on what did you mean by. Do you remember? It looked like a 60 minute interview or something. They were like, what did they mean by domination? And then to pair that with that was like, ooh.

It's been reported that in Friday meetings early on that Mark used to end the meetings by saying domination. Is that true? That is true. So tell me about that. What were those Friday meetings and what did that mean? Domination. Yeah.

Yeah. You answered that very diplomatically.

Well, that was a really tense conversation.

I didn't like it.

Oh, dude, they put us in.

He.

It felt like we were sparring.

Oh. It felt like as a viewer, he.

Was angry, and I was.

He just kept getting angry. He kept getting angrier at the end. And I felt like at the end you had, like, found your calm because he hit you with that. He hit you with that one. At the end. I was like.

I also realized that, you know, I was upset because I felt, like, a little bit trapped. It's like, guys, why don't we set up this meeting? This dude clearly has an agenda for what story he wants to tell. He just needs me to spit out the words.

Right.

But I think you didn't give him.

The Death Star back then.

But I think what I was trying to impart on him was that, like, look, we're fighting for our lives.

That was what I took away from it.

Like, we did not take for granted the fact that we were gonna be successful by default just by showing up. We had to earn every single victory along the way. And frankly, there were much more successful companies that were now left to rubble. Right. That was at least the way that we internalized.

We lived through it. We watched all these.

Nokia got vaporized across the street from us.

Amazing, right? I mean, literally, the Business Week was.

Putting them on the COVID and saying, these people are going to dominate the future. They're gonna. They're gonna spell out the whole way the. The world's gonna work in the next five to ten years. Four years later, gone. And so we were an intensely and rightfully paranoid environment. We weren't nefarious in our product motivations. We were just trying to stay relevant in people's lives.

And how did the lore of Newsfeed then, like, fuel it? You know what I mean? Like, how did it embolden people? Like, for the business, it was like, remember, this is who we are.

Yeah. It emboldened us on a couple dimensions. The first is that newsfeed revealed the company's sheer ambition. It surprised people outside the platform and users like, oh, my gosh, this is not what I signed up for. This is actually really novel and new and borderline, like, dangerous. Like, what's going on with my data? Like, who can see this stuff? There was enormous blowback.

I remember I was there. Protesters. We had protestors outside of the building.

We had to exit out through the parking lot. It was low key scary. And I think the Rubicon moment was watching the newsfeed Privacy Team spin up an initiative to listen to what users were saying, build the privacy settings people wanted, and shipped that days later. It showed that being wrong was forgivable, but being slow was not right. And it showed that our conviction on what we think could be an amazing experience for end users. We may not execute on that perfectly with v1, but v1.1 will get us there, v1.2 will get us there. And we can iterate our way towards what people actually want as long as we're listening and responding in real time. And so I think that what it kind of fused in the culture was like, we can take bold bets, we can fix our mistakes quickly, as long as we move quickly. And we can't expect people to necessarily understand what it is that we're trying to accomplish at the onset, Especially if it's transformative, that all transformative technology disrupts things. It can sometimes be dystopian, it can sometimes be scary and unnerving, but that's a byproduct of progress. You have to kind of move people forward and impute change. And if that change is in fact good of the long arc, then it's worth it. And it requires a backbone of steel sometimes. And I think that was the move fast and break things.

I love that it codified into mistakes are okay, slowness is not. Yeah, that's so good. What was the lore of Dropbox and how did that get communicated?

I think the lore at Dropbox is thinking through all the details, chasing down that edge case, that bug. It was almost a very MIT esque way of thinking about product. Get the whole program in your head, understand all of its endpoints, make it spatial to quality software. Right. And imbue it with a certain amount of whimsy and delight. The service was the first SaaS company that I can think of that had colored pencil drawings kind of intermixed in the product and in the marketing materials. We formalized that with illustrations. One of the first things that we did when I joined Dropbox full time to run the design team there was to build an official illustration team, both to scale that practice within our design group, but also to embrace that aspect of our culture. We had gone through a short work Sprint, where we stripped out all the illustrations from Dropbox and it felt cold and utilitarian. And we sort of lost the soul of the business in that. And we realized, well, actually illustrations are great not merely to kind of give flesh and taste and personality to the product, but there's something a bit more fundamental to it. That's. We are visual communicators. We can convey really abstract concepts visually in a MANNER that like no. 10 or 12 or 15 words can really capture. We didn't have ChatGPT back then to give us, like, you know, product copy. Right, right, right. And even then, people sometimes don't read. They sort of glance over it. They don't understand these abstract concepts such as backup and cloud storage and synchronization, but they would understand a picture of a laptop on fire and a smiling face reassured that all of his stuff is sitting inside of a Dropbox in the cloud. Right. In the sky. Right. We are visual creatures. And so illustrations ended up serving the purpose of reinforcing key concepts and ideas at different parts of the product journey. And I can't imagine a world where Facebook would have had an illustration team. In fact, I remember on Hacker News, the product tour, the first product tour that John Yang created for Dropbox, that sort of was a storybook walking you through what is Dropbox and welcome to it. That got sent around Facebook sort of under the premise of, like, maybe we should do something like this. And I distinctly recall responding to that good old reply all saying, like, guys, no, that's like, not way.

That's interesting.

Facebook way.

Facebook Way was what people first.

You don't use Facebook because we spin up a storybook telling you how wonderful the world is with your friends. You don't need that story. You just need your friends on the service sending you photographs, messaging you, adding you. You need, like, your high school sweetheart joining in the service.

Right.

And seeing that notification and being able to browse your photos. Facebook was in the background. Facebook was not. We were the vessel. We were not the main attraction, and that was not the Facebook way. We were much more obsessed with product mechanics than, like, storytelling.

So is there anything to you being a Facebook six years and only two at Dropbox about those two cultures or companies?

You realize that company culture does get set early on, and it's really hard to shape company culture that far into its journey.

Yeah.

Whereas, you know, I joined Facebook in 2005. We were very much pre News Feed.

Yeah.

It was just an idea in the sky.

Yeah.

And so to be able to directly contribute to company culture, did it feel.

Moldable back then, even in 2005? It started when?

2004.

Oh, wow. Okay.

Yeah, absolutely. Yeah. Because again, we didn't have any real successes on our belt in a global sense.

But Dropbox was established. It came out of the gate hot.

Yeah.

You know, it was that first kind of consumer.

Consumer SaaS business. I can't name a consumer SaaS business before pre.

No, I think that's right.

Maybe AOL. I guess you can call that SaaS, but not really. That was more like ISP. I'm really grateful for the Dropbox experience, though, because I think it taught me a combination of things. It kind of ran the things that you learned at Facebook through a different context and sort of. It provided, like, almost like a purifying test of, like, what holds true irrespective of Facebook and Dropbox, what's sort of generally true. But then I think for me, it kind of taught me which parts of Facebook came from me and my own sensibility. Which parts do I think I value and can authentically project into the world?

Is that clarifying to try to. I don't think I've given those things to Dropbox and realize, like, oh, no, that's me. That's not Facebook or Dropbox. That's just who I am.

There's a little bit of that. And then you also realize the extent to which you don't really know a culture or nation until you confront a different one. And so it made me appreciate the extent to which, like, Dropbox was able to succeed in a vastly different context than Facebook. And a lot of it stems from the business model. It stems from the founders and their personality traits and what they value and then how that gets magnified across a culture. I think culture is probably the deepest moat one can create, and that's a very real. It's a very real thing.

It's a real thing. But it's really hard for particularly technical people to wrap their heads around because it's not quantifiable. It's not. In a lot of ways, people don't think it's measurable. It's not immediately even obvious how to shape it intentionally.

For some people, I think it could be measurable.

I think that's right.

I think there are ways to codify it. A dear friend of mine, Ben Barry, he created the Analog Research Lab.

No, I know. We love. We passed the red book around.

Oh, yeah.

I keep trying to get him to.

Make a red book.

He wants an indie red book.

Little Red Book is incredible. And I think what I love about the Little Red Book is they put in that extra effort to kind of encapsulate things that they. That Facebook sort of held dear. It was almost like a. Not a founding document, but it sort of. There was like a constitutional aspect.

I love that.

Yeah, Right.

So it becomes almost a Reference point for people. It's your point. Like, what's the Facebook way of doing these types of things? How do we think?

And there might be other ways to do other things. Right, of course. But this is just the way that we are gonna do this.

Yeah.

Right. And then that way, if you join, you can understand not the long history of like, oh, these are the glory days and all the stuff that happened before.

This is not a victory lap.

Yeah. It's more like general purpose knowledge. This is the way.

As you read that red book now, do you look and say like, oh, that was me.

Yeah, yeah. Oh, yeah.

What are the parts of that that jump out?

The quick shall inherit the earth. I'm a failed Catholic code naming things. Like we had our first UI library we called Canon.

Oh, I love this. That's amazing. So good.

Because it's true.

It's true.

If, you know, inspiration is so finite. Right. If you don't act on it, it just sort of goes away. Right. And so sometimes the best way to kind of capture lightning in the bottle is to be faster than lightning. You have to just be faster.

Well, I think that's one of those things that you actually can condition yourself to either way. Like either you condition yourself to act on that inspiration and the interesting thing that happens from there is you get more of it and yet the more you ignore it.

Yeah.

The further and further you get from it.

I remember years ago I came across this incredible, like simple article called the Manifesto of Done. And we would go out for beers.

I love that name.

That's incredible.

Yeah.

We go out for beers and I would read it aloud to people.

Is that right?

Yeah.

Beat poet in the corner. I love this.

And it was great because I felt like in some respects it was a form of like, not indoctrination, but kind of. You know, Peter Thiel famously said that startups are like cults. And so there was an element of cultishness to this focus on speed. That's how we thought about design at Facebook. It was a capacity for speed. How can we prototype and build something so that we don't spend a bunch of engineering resources? How do we just get the thing out the door without even having to spin up an engineer? We would ask designers to push production, like write code on their first day. It was kind of, you know, shoot first, ask questions later.

Yeah.

Now there's a lot of. There's a lot of trade offs that come with that approach. I think the glass ceiling that Facebook will always grapple with is if you move really rapidly. That's sometimes hard to align with trust building. It can be unpredictable. And I think that trust often requires.

Predictability from the outside looking in. Has it been what's it like to look back and see how that move fast, break things? The quick shell inherit the Earth has tried to adapt to like this now. Global scale, massive impact, and much more complex business units.

Yeah. I think part of it is seeing how they execute with an incredible amount of pace across these different business units.

So you've still been able to keep that as a core value.

And they have. I mean, the degree of complexity is extraordinary.

Yeah.

I'll caveat all this that I've never worked for a company that's bigger than 2,000 employees. So Facebook is as foreign to me.

Is that as big? When you left, it was only. It was less than 2,000 employees.

Yeah. It's as like Facebook is as foreign to me of an organization as Japanese government. I know it exists. I know it works. I don't know how it works. But I do appreciate from the outside, from across the street, that they do respond much more rapidly than you would expect. Small teams do get incredible things done quickly and they're okay with making mistakes and reversing course. They may say, hey, the Metaverse headsets are the future, and realize, oh, wait, actually, maybe smart glasses are a better form factor. So we'll do that and then we'll keep working on this. But this is clearly the future. Right. This is where we see market pull. And that's fine. That's okay. I think that that what any great company in software has to do is be able to demonstrate deft at scale. And I do admire the company for being able to do that even many, many years later. The fact that they launched Threads, a tiny team inside of Instagram. Right.

Within days. Incredible.

And it's well executed. It has a lot more polish around.

You're not moving over the threads.

What's that?

You've not moved over to Threads?

I still use it, I think I haven't quite figured out. So we used to call it the juice with Newsfeed. I love this Newsfeed juice. There was sort of like a je ne sais quoi to like, stuff that would get distribution on newsfeed. And it's kind of like the Matrix. You can sort of intuit like this will probably cook. This has got juice, right?

Yes. You can't figure out the juice.

It's a total black box. Right. And I feel like with Twitter now, X, I, I understand what gets juice. You know, you can sort of see when it shifts with threads, I'm like, I can't quite predict what's the kind of content that resonates in this platform yet.

Same, same.

That's not a criticism. It's more like I've got to put in more time and energy to explore what it is or not. Or not. With threads, there's a different sort of pace to it and there's like an agreeableness. I don't know how I can contribute.

In a meaningful fashion, being such a disagreeable guy. Oh, that's funny.

But I love its design, its execution. I love that it is kind of putting forward new voices. It feels like a more social network than.

I get that too. It's definitely a warmer, fuzzier place to hang out.

Yeah. Yeah. X has.

Feels like a battlefield.

Yeah, it's awesome. It's like a town square.

Town square with landmines buried everywhere.

What's that? It's like the Gangs of New York. That is X to me.

It's totally X.

And so there is an entertainment factor to it for sure.

In and of itself. Totally. That's so real.

Yeah. But I do admire how Meta has evolved, has kind of imputed on itself a desire to evolve. Right. And it's really comfortable with just being almost unsentimental about its own success. You know, we would redesign things all the time under the premise that, you know, it's like a. If we don't kind of self disrupt, some guy's going to show up across the street and do it for us.

I'm going to put a pin in it because I want to go back to the Happy Meal thing, but this is something we've been talking a lot about, which is like, tech doesn't value the past. It wants to look forward, it wants to work on the future.

Yes.

Whereas in other creative fields, even in design and other categories, they draw so much inspiration, they hold so much regard for the past. Tech doesn't do that.

Why do you suppose that is?

You had a tweet the other day that actually made me revisit this thought, and that was the one about sci fi. So I wanted to believe that, like, oh, it's the. You know, the tech doesn't value art and it doesn't value. It doesn't value outside input because it.

Believes you can build up from first principles.

First principles. There's too much baggage in this old stuff. The people who actually build the future aren't tied to the past in any meaningful way. They're not coming From a place of understanding. They're bringing this first principles approach to it. And so why reflect? But then you. I don't know if you even remember this tweet, but you were talking about, like, the influence of sci fi. And I guess what that made me realize, like, I'm not a big sci fi person. And so maybe part of what I'm missing in that draw to the past or to other cultural reference points was that they're just not my cultural reference points. I don't maybe watch the same movies, I don't read the same fiction, I don't read the same science fiction. Maybe it's being informed by something that I don't fully appreciate. And so I think there's probably something in there that gets closer maybe to an understanding of reference points and culture in a way that I want to pull it from fashion, or I want to pull it from art, or I want to pull it from these other places. It's just a different way to frame it.

Yeah. And I think, you know, environment does breed culture in many different ways. If you use New York as a foil to Silicon Valley. Silicon Valley is new.

Yes.

The environment screams what's next? Command N. There's no legacy. I have a barn in my backyard that's allegedly one of the 14 oldest structures in Los Altos.

Is that right?

Yeah.

Amazing.

But when was it built? 1910s. There was a post office box down the street from me in Chelsea that, you know, is hundreds of years older than that barn and has no historic status whatsoever. Right, right. And the reason why I think this is relevant is because I think people who came to the Bay Area, you know, og Silicon Valley, they were a part of the post World War II sprawl. It was all new. Nothing was precious. Anything that was done could be redone again. And so I think that one of the things that is striking to me about the Bay Area in particular is that that sense of what's new, that sentence of frontierism, puts people in a stance where they're not looking to adhere to anything because there's nothing really to adhere to. This grove was the same 10 years ago, pretty much the creepy house was there 10 years ago. Right. But software has moved on and moved on, and some of the hardest working people that I know are also the most successful because it's. There's an obsession. The social currency is what's next? What's next? What's next? It's not like what you accomplished five years ago.

We moved out here for two years in 2010, and I remember taking my oldest daughter, who at the time was probably 14, to middle school and as we were driving, you know, we come from Utah. Utah is a very, we love it. But there's like a, it's a funny. It is not a culture of the new. It's very rooted in like pioneer and history and lore and Mormon, you know, like all of that stuff. As we were driving to school, she looks at me and she said, dad, I feel like I can finally be myself here.

Yeah.

Like as a dad, it just crushed me. But also I immediately understood something about California and this place that I don't think I fully appreciated until I was here.

Yeah. And I. That sentiment resonates so deeply for me. A big reason why I was compelled to come back is that there's no other place where I felt like I really belonged. I felt like home turf. Right. And that sounds possessive, but I think it's also just a response to, you know, having the incredible privilege of seeing the world, seeing other cultures, and in doing so, recognizing what is uniquely special about the Bay Area and Silicon Valley. That it has this active stance of like, you must come up with what's next. That's like why you're here.

That's right.

It's self selecting in that fashion.

Right.

There are people from much humbler origins who have moved themselves across the planet to be here. And I didn't appreciate until I was living abroad how much people look to the west and specifically to Silicon Valley for that inspiration for that forward movement. Like what is the next doodad, the next gadget, the next way in which I can reflect upon the world because it's not happening in Europe or it's not happening in other parts of the world. And I think a lot of it just comes down to the absence of history, deep history that so many people hear are transplants.

So you're saying it's a feature, not a bug?

Yeah, yeah, yeah, yeah, yeah, absolutely.

Did you feel the weight of the history when you were in London? Like, how, how was that experience for you?

I thought it was awesome. I mean, you sort of see, I don't know, there is something about it being the center of the world, of an empire, and seeing maps that span decades, generations, centuries, where like the contours, the structure of the city remains intact and the degree to which we stand on the shoulders of, of Western civilization, which really achieved global sprawl by way of the British Empire. The scientific revolution. Right. It's incredible to sort of walk around there and be like, yeah, those guys walked into that building. Literally that building had same sort of conversations that I feel like I eavesdrop on over at Phil's Coffee and pushed the state of the art forward. I appreciate being in that environment because it gives you a sense of their fluency for institutions because that's like what they were raised in. That's the environment that they exist in. Everything's kind of fortified around institutions.

But interestingly, institutions there are revered.

Yes.

Here they're the Death Star. They're villainized. They're, you know, like.

But I wonder if it's a lack of fluency. I wonder if, like, that is our responsibility as maybe generation one technologists is like, well, what is the California institution? The closest thing that I can think of might be the University of California system. Yeah, right. That is an institution.

Right.

That stands for something that was an ambitious program. But what more can we do? That's almost like a hundred, like 100 years old at least. More so. What more can we do as a state of California, as the state Silicon Valley, to put forward future institutions, things that folks will look back on and revere much the way that we revere the Constitution. Right. And I think that's a big question that we ought to be asking because it now reframes the work that's done today along a longer arc. Right. You're not just responsible for you and your kids, but really for civilization at large.

Yeah. What did you miss in London about the Valley?

The enthusiasm for ideas?

I don't know. I'm just watching it from afar. But it feels like there's a cultural battle waging almost right now between Silicon Valley and Europe, Silicon Valley and England in particular. Silicon Valley is looking at them and judging them and saying, see, you don't know how to build big companies.

Right.

All of your companies are these legacy monsters. Your countries are great to visit. They're phenomenal tourist traps.

Very civilized.

Very civilized, Very civilized. But they're not innovators.

Yeah.

Does that square with your experience there?

A little bit.

Oh, interesting.

I think what I missed while I was there. The United Kingdom would talk about a desire for innovation and disruption, but their culture is very resistant to that. They fancy the idea of the software engineer intern becoming the multi billion dollar CEO. But there's no homegrown examples and there's no real dedication to creating those homegrown examples. I hope that might change. But that to me is like the thing that I kind of look back on is that there's social currency there doesn't come from generating new wealth through A new business. It took you three years.

Yeah.

Not a whole lot of currency there, really. Currency there is status, your station in life, your proximity to the king. It's very classist culture. You talk to people and tell them, I work with startups and their eyes will glaze over. Right. But if I tell them, if I tell them. I was at Facebook, I was one of the first designers. Oh, tell me about that. And to me, that's like, I sound dusty and old. Just saying that I spent hours in front of IE6. I can get that browser to do things you couldn't even imagine. People in India and Bangladesh thought that our website was from the future.

That's right. Oh, my gosh. What's that startup scene like, though? Because that's like outsiders. How do those entrepreneurs. I think.

I think it's ascendant.

I don't know if you spent much time in those circles.

I definitely did. I mean, I got to partner with a variety of startups there. I think there are really compelling teams that are going to succeed in that environment, in spite of that environment. But because it's an ascendant ecosystem, they are increasingly seeing the support from American investors, from employees that are coming out of the bowels of Google and Meta and are feeling that sort of itch. And frankly, we now live in a world where so much content is readily available. I mean, I think when I look back on, you know, I became close friends with Harry Sibbings while I was there, and what struck me is how he pioneered this whole space of, like, podcasting venture content right, as a kid and navigated it right through that lens.

Of, like, just, there's no 20 VC episode of you yet. Why is that? I looked. You were not in the obvious places. Yeah, but I went to Lenny. You weren't there. I went to 20 VC. You're not there.

I keep a fairly low profile.

Not after this.

When he was getting started with 20 VC, a big reason why he was doing the podcast is that information was readily available. The kind of basic 101 questions that founders, European founders would have, nobody had the answer for. A lot of this knowledge was locked up in people's heads. And the saving grace of podcasts, to be frank, is that unlike services like, say, Quora or Wikipedia or even Facebook, podcasts have enabled a medium to which people can just share their knowledge in real time in a format that's easy to consume and where the knowledge is really tactical and extraordinarily valuable to people who don't have that lived experience. Right. It is an unveiling of common wisdom out here. And so I think that that is meaningfully reshaping the startup ecosystems abroad. Because now rather than having to know Lenny to even get any sense of.

Just pull up your Lenny bot.

Yeah, you can just pull up your lennybot. Right? Yeah. Or listen to all the incredible people that he's curated and had conversations with.

Right.

And that's an immense good. And so I think that that's going to embolden tomorrow's founders overseas to start businesses in their hometowns. And I hope that I was able to partner with some of the people that will contribute towards London becoming a tech town. The first wave of real tech titans.

Could you feel it changing over those four years?

Yeah, I mean, when Sequoia sets up shop, you know, they're not doing that as a, you know, as a vacation spot.

Yeah.

They want to make a lot of money. That's the game plan. Game plan. Make a lot of money here. And so when American BC starts to show up in London, that was a clear indicator that there's a long term investment in that space. And it's consistent with the critical mass of talent at these later stage firms. And it's certainly consistent with the ambitions that I see from entrepreneurs coming out of these firms and saying like, okay, I had my first rodeo, I feel ready to now try this myself. But then you have to kind of push them.

Do the branch offices of Google opening their Facebook, opening their Instagram.

That's meaningful.

Okay, it is meaningful.

Yeah. You don't have a Mike Hudak working on Sling unless he's the CTO of Monzo and leading the creation of the London office for Facebook. Right. And so I think there's like, talent gets transplanted and these ecosystems kind of grow.

Yeah.

Like a grove. Right. It takes time. So I'm optimistic about the space out there. I think that the key difference between the two ecosystems is just life cycles here. There's just denser networks. And I love that I can spin up and call friends and colleagues who I've worked with across multiple contexts. And it has almost like a Hollywood quality to it where it's like, hey guys, I need you to take this introduction because this team is going to be cooking in 12 months. Right. And not have to go and do the whole dog and pony show because you just have kind of built up over time that community in one particular region, one particular place. And it is self selecting. And that place is Silicon Valley, the infomercial.

This is going to be amazing. We're going to have Gavin Newsom retweeting this.

Oh, speaking of Gavin Newsom. So one of the things that pains me about California, now that I've experienced the wonders of the old empire.

Yes.

Is that there's no power corridor between Sacramento and Silicon Valley. California is the fifth largest economy on the planet. Right. If there's ever a petri dish for showing how technology can create new forms of governance that work for the people, I cannot name a better one than California. Why is it that startups think that selling into government is, you know, a death knell? It should be the opposite.

Why do you think that ends?

I think partially it's culture, partially it's the political.

And you touched a bit on, like, part of it is convention. Like historically, people have said, oh, you don't want to sell the government, that takes too long, you can't.

VCs are like, don't do that, you're gonna die. But then I think there's also a certain degree of political homogeneity. Like, there's people don't.

It seems like from the outside looking in, there's this randomly active resistance against technology. The technology culture of California, by the vast majority of people in California.

There could be a little bit of that. But I wonder if a lot of it's just, is that in Sacramento? Can you name three people in Sacramento who are not Gavin Newsom?

No, of course not.

I bet you if you and I spun up 50 of our colleagues based here and asked them the same question, we might be lucky if we got five names.

Yeah, that's probably right. I'd buy that.

And I think that's very problematic. I think in much the way that New York and D.C. benefited one another, that power corridor should exist in California. We've got the people, we've got the resources. I mean, all the things that you can possibly want in a petri dish to show people what highly effective governance looks like exists here in California. And that only dawned on me when I was living in the UK because I appreciated that the UK could be very top down. Their websites work are useful. Right. And yet it's almost useful in spite of the way that the politicians just don't even understand how to use a smartphone. Right, that's so. And they're deeply skeptical and cynical about emerging technologies. And so you'll have these politicians and MPs show up and say, like, well, AI is going to mess up the world and we have to be very, very careful. It's like, no, the whole conceit is that it Increases productivity.

But they hear. But for some reason they interpret that as like it loses jobs.

And at the same time.

Which is wild.

And at the same time they're also saying that all of our agencies are overwhelmed.

Right.

So which is it? Right? You can put an AI tutor in every child's pocket in the uk. That is doable. They can negotiate those deals today. Right. Why don't they. Why doesn't California do this? Right. We have the means. I look back on how Steve Jobs would evangelize the Macintosh by way of the Department of Education, by way of schools. We owe it to kids to give them the state of the art now. And we owe it to, I think, the population to escape this 20th century mindset that school is just for children. Continuing education program. Right. We now have the economic and technological means to do this. I don't think I could do that in the uk. I think I might have a slightly better chance at working on this.

You heard it here first. Saleo, governor, 2026 campaign. I'm going to be the campaign manager. We've got the media. Let's go. We're spinning up the media right now.

I have to brush up my Spanish a little bit. Yeah, I got you.

It is my first Spanish.

It's my first language.

Because you're, you're, you're. That's what I thought. Because you're online. You're a. You're a. You're a one name man. But then as I dug in, I'm like, Cuervo or what? How do you pronounce the last name?

Cuervo. Cuervo. Yeah.

Okay.

My parents are Colombian immigrants. Yeah.

First generation, first gen. Yeah. How old were you around? Such a good campaign story. It's gonna be incredible. You're gonna have a lot to explain to your wife at the end of the day. Oh my gosh, sweetheart.

I'm a politician now.

Just so you. Good news.

I'll just, I'm done investing.

I'll just leave the keys on the counter. You tell me when I can come home.

What's your midlife crisis?

I always tell people, like governor of California. I. I always love. Yeah, exactly.

That's a great movie pitch. That sounds like a terrific rom com. Like I would, I would watch that sight unseen.

So I did listen to something you did. And you said in another life you would do. You would make movies.

Yeah.

What would that be? Because I think one thing I see with your stuff, I think it's. We did one of these with a guy named Charles Bukoski. He has a personal campaign and mission to get artists to start startups.

Okay.

And he's like, I appreciate that. It's impossible, it's hard. He goes to art schools, he pitches all the time for these people, these creative.

Can I give you a theory on why?

Yeah.

I discovered over time that contrary to what I think our intuition would say, designers are very risk averse and that's why it's so hard to bring them into startups. As a class of worker in tech.

Where does that show up? Risk averse? What do you mean by that?

I'm not sure if I want to join a startup. It's hard for me to imagine how it can grow into a thing.

Oh, interesting.

Who am I going to be working with? They need to see the desk. They need to know who they're working with. They need all. Everything that can be de risked must be de risked to bring somebody into a startup pre product market fit or before their parents have heard about it. There's just, I think, a baseline risk aversion that seems contrary to a creative mindset.

Right, right, totally. You're blowing my mind with this.

So my theory, my theory is that this extends to artists and creatives that fundamentally as an archetype there is an insecurity and a risk, a profound risk aversion that keeps them from feeling the agency to go and start and run a business, which is an extreme act of agency and courage. Right. And I think entrepreneurship to them is just a long word for self harm. It's really, really difficult to even fathom being responsible for payroll and other people's well being. And so I think the creative class may retreat from that. Which is why I admired the few that break through are exceptional. They sort of, they have like a spirit that is contrary to the archetype.

So it's interesting. Would you say then there's value in that bar being set so higher, that filter being so narrow that it takes that kind of like herculean belief in yourself. Herculean effort?

I think so, yeah. And I think that's why I gravitate to folks of that ilk because they are truly the ones that are courageous enough to make the future so they have the aptitude to do so. But also just like they're almost like the absence of fucks to give right to go. And like I learned how to use a computer, now I'm doing things with the computer and I'm shipping it. Right. The Ben Barry's of the world, the Rasmus Anderson's of the world, who were able to be the best in large part because they were amongst the first. And so the art school kids need the institutions, they need the curriculum, they need all of that journey to be de risked in many respects.

Is there an element of it where they don't see people that look like them being CEOs?

I think there might be a bit of that, Yep.

There's another dimension of it where it's business in air quotes. Big B. Business feels like a black box. No, it feels like there's. It feels scary and complicated.

Like scary is the word.

Okay.

I think it's fear. I think it's standing on a precipice and staring down and be like, nah, I'm not going that.

Because any job they've had, revenue has never necessarily been clearly tied to that job that they've had. Business metrics. A lot of them potentially don't fully understand the economic impact of any of the design work they're doing or this creative work as an artist is doing. Do you think there's anything to that?

It can range from disinterest, maybe, to, again, like, just a sheer magnitude of responsibility.

Yeah. You know, I just want to push pixels, man.

Hey, there's a reason why we like being a trim little boat.

Right?

Yeah.

Right. They're also not commercially minded.

Yes.

Like, they're creative and so they want to. They want a patron, they don't want an investor, they want support. They don't want employees.

Yeah. They want admiration, they don't want customers. Yes.

How have you seen them get over it? You mentioned two by name, Ben and Rasmussen.

In both of their cases, I think there was just a certain amount of experimental curiosity, like, what can I get the computer to do? What funny things can the computer do for me? That combined with just the artistry that I think is innate to both of them. They want to make it resonate to them. They want to make it beautiful. Rasmus got into font creation as a teenager, kind of went through the ropes of designing little pixel fonts, which I think, like everybody in the late 90s did, and parlayed that into designing Inter, probably the most used open source font on the planet. I gave him shit all the time because he didn't name the font after himself. And I'm like, rasmus, this will be on a spacecraft on Mars one day.

100%.

Like, you've immortalized yourself, man.

Right.

You should have called it Rasmus. But. But being the humble gentleman that he is, he's like, no, no, I think Inter is a nicer name.

Right.

And I think it does come from a place of curiosity, aptitude, but the courage to put things in the world and not be precious about that, not be precious about monetizing it per se.

Do you find that there's a multiplying effect for every one that does? Yeah, someone can point to them. Because I remember talking to Kari Alinear and he said something along the lines of like, yes, we're doing all this stuff differently and yes, we're trying these things, but none of it matters unless we win. It's really just a question of, like, for every rat does it spawn 1 more, 2 more, 3 more for people to say, like, oh, look, someone like me was brave enough to go do this thing. Because they look at Zuck and they say, yeah, that's not me. Like, I don't know, I don't see myself in that at all. Or I don't see myself in Jeff Bezos or all these people that we hold up as like icons, especially to a certain creator class, they look and say, I actually don't like those people, like Elon. Like, I'm not inspired by that. That guy seems like a jerk.

Yeah. I think success and archetypes do beget success and further archetypes. The folks that are creative and put work out in the world that resonates in a profound way, in a big way. They are not typically hole in one artists or creatives. This is like one of a thousand things that they've done and everything else is in the dustbin of history, but it's out there for every Little Red Book. Ben Barry has a lot of like, crazy side projects and stuff that he's shipped, he's put out there that nobody's heard about or seen or care about. And he's content with that. He's okay with that. He understands that's part of the practice. You know, you're taking these shots and it's just that alone. Being prolific is an art onto itself.

That's such a great point. And there's a part of me that feels like it's becoming a lost art.

Yeah, it's.

Yeah, maybe there's a sense that, like, it's not worth tinkering or starting on something that isn't obviously a venture scale business anymore.

Yes, I agree with that. And that, I think is the most hostile attitude to the foundational story of think of Silicon Valley, which is homebrew computing, completely. None of these guys were like thinking about how to make a buck, right? There was just a sheer curiosity and Desire to connect with other people who are just doing it because it's fun.

That's right.

Because it's interesting. And because you and I can exchange, like, emerging wisdom that we just learned.

I figured out how to do this. Did you figure this out?

Like, did you see this prompt? I did this weird prompt, and now it's generating this. This is crazy. It's just sort of sitting there. And that means that there's probably a thousand other things like this just lurking, waiting for us to find it.

How do you foster that, either as a manager or as an investor, to give people permission to explore things that might not even feel commercial? What I love about the red book is it literally says Facebook was not started as a company.

Correct. Yeah.

That's the very first thing it leads with. Why was that important to the culture? And how do we get more people to embrace that as an underlying idea?

I think because in some ways, it runs a little counter to the American story.

Totally does. Like, we've. We reshape.

It's like a different form of manifest destiny. Yes, right.

I think that's right.

And in some ways, it's like making the buck can be the central impetus of a new venture. But the reason why Facebook is an interesting archetype, and Zuck has said this multiple times in interviews, where it's like he trusts inside projects because it imbues a project with a genuine desire for it to exist beyond any sort of commercial viability. It's just more just like a sheer form of self justification. Right.

Just because I wanted to listen that acquired podcast that came out a couple weeks ago, I was like, this is. This is a lost art. You know, the fact that when they started talking to investors, they weren't pitching Facebook at all.

Yeah.

Like, it actually. It didn't even seem like it was the thing. It didn't seem like the business, but it was among this portfolio. Portfolio gives it too much weight. It's just this, like, grab bag of stuff.

Stuff of, like, my projects.

Totally.

Yeah, totally. A bunch of kids.

Yep.

Yeah. And I think the. That's why I really. I embrace and love when successful entrepreneurs have these side projects that they announce or go on to work on other initiatives beyond the company because it shows that creative impulse. And I think in so many respects, founders have to lead by example there, too. Not merely for their employees, before the work, for their customers, for people who look up to them and say, like, I want to be that guy.

Right.

So, well, that guy also, like, produces goofy albums on the weekends. And that's okay. That's fine. He just stand up.

That's okay. But that's probably why these other dimensions are working as well as they are too.

Yeah. Oh, absolutely. Because it gives you a broader sprawl of dots to connect, right? Yes, absolutely.

That's so good.

Yeah.

I want to go back to the Happy Meal, though.

Oh, the Happy Meal.

Like what worked and what didn't. And then there's another part of it was like, how did it feel to invest other people's money?

I felt a duty to that capital.

I'm sure you did.

And I think it changed the nature of investing for me in a fundamental way. You have a. In our case, it was a $20 million portfolio or $20 million vehicle. So we have to return capital. And so everything kind of flows from the logic of portfolio construction, of course. Right, right. And what you pitched LPs to do. Right.

Part of what you pitched LPs was like outsized ownership through advisory shares and.

Exactly. And so I think right out of the gate, if I were to go back in time, I would say like, start with a smaller version of that.

What would the smaller version be?

A much smaller vehicle. Right.

Not 20 million. So there was the dollar amount.

Yes, the dollar amount. But also just try to unbundle the Happy Meal a little bit. Right. I think we were trying to, to do. To innovate on the model and innovate on the offering and hybridize. Two very different operators.

I cannot relate to this at all.

Yeah.

And also trying to do too much.

And become fund managers simultaneously. Right. Which I think in and of itself, once you manage outside capital, you realize, oh, VCs get a bad rap. Really great VCs, man. That is. It's like people who are really amazing at JavaScript, like there's talent will get you so far, but then you've really got to put in your paces. Right. That is an art. That is something that you build brick by brick, man. Right. And so like you, you don't get that just by showing up. The concept didn't get stress test before. We had kind of committed to the model and the fun size and what we promised LPs. And so in many respects it kind of created these really tight guardrails within which to operate. And I think especially as a first.

Time manager, you're like, wait, we told people we were gonna do this? You are presented with or confronted with something that doesn't fit squarely into that box.

Right.

And you're like, what do we do?

Yeah. And then I think that, you know, the other piece is that you learn, again, everything's obvious in hindsight. You learn in practice that when you are a service provider and an investor, a major investor to a founder, you can find yourself in conversations where it's like, are you my dad or are you my doctor?

Okay, say more about that. Because I feel like we don't talk enough about. Because I actually think a bunch of people have tried to duplicate what you started, but that seems like such a fundamentally human thing that if you were just looking at the model from the outside, you'd be like, what's the problem?

We were rendering services in kind in exchange for equity, in addition to our substantial stake by way of investment. So we were both investors and service providers. Right? If you're in a conversation about software that has a material impact on the, on the strategy of the company, right. What we end up doing as a venture and there's disagreement between the founders and the service provider, and we think, wait, we disagree with you. You should do XYZ to the founder's ears. Who's speaking to them, the service provider or the investor? Right. And again, it's like, as much as.

You would like to believe that you're getting the same weighted advice to a.

First time founder, that ambiguity can kind of create tumult. Am I getting advice? It's like, if your dad's your doctor, like, are you saying this is my father? Are you saying this is my doctor? Right. Like, how should I be listening to this? Right? Because the way in which I listen to it will materially impact how I respond to it, right? It's like, no, I'm the CEO. I hear what you're saying, but we're gonna chart the course forward. But that's a very different thing to say to a service provider than a major investor who led your seed round.

How far into it before you started to feel that friction? Because like you said, you weren't able to stress test it before.

It's not so much friction. I think again, it was just the a byproduct of the Happy Meal effect and realizing that some founders want the fries, some founders want the burger, some founders want the toys. And each one of those attributes of what we're offering involve different processes operationally. And then two, they involve like different sales cycles, Right? Like, investing is not the same as being a service provider in the way that a classic design studio would work, totally personnel wise, just, just even mapping out like what's happening this quarter. Right. It's just not the same operation. And So I will always look back on that experience and reflect on, like, I remember three conversations during fundraising where again, these really smart VCs correctly predicted what happened. They're almost clinical in their approach to it. It's like, they must be really good at predicting how startups fail. That must be part of the job.

How do they articulate it?

Well, they're going to be, they're like, whoa. You're going to realize that it's hard to operate a design studio and its operations internally, but also its sales motion relative to a venture firm and its internal operations, pipeline management and kind of just LP management, like stuff, that these two things are not exactly the same. And then over time you realize that it would be much easier to operate the design studio if you're servicing non portfolio companies. But once you open up that Pandora's box, then you might as well give it the profit motives that it deserves.

That's right.

Right. And now you're no longer hybridizing anything. Right. You're creating two parallel companies that are not getting the benefit.

That's one, raise your growth fund.

Yeah. And then. And then, of course. Yeah, exactly. Yeah. And then of course, on top of that, you know, if you talk to founders, they were accepting checks from us, not because of the design studio, because they wanted to work with me and Adam.

That's it. Yeah.

And. And at the end of the day, like, that was a really hard realization. Once you've raised this capital, you've set this thing in motion, you're like, oh my gosh, we have to figure out a way to make this work. And if we don't, I have to make a big life decision around, do we have a competitive strategy here? Is this really what founders want? Maybe it's an education problem. Maybe we just have to be better at marketing the Happy Meal. The ambiguity for me and the lack of ball control, being a micro fund and not being like a lead seed investor, I just didn't have the conviction to really want to pursue a line of work that would commit like 5, 10 more years to it. Right. And that frankly wasn't an extension of what I had done with Dropbox and Figma, which was investing capital and being like an advisor. Plus plus for shares. Right. This is a whole different ball of wax. Right.

Yep.

When Covid landed, it was like, okay, and now I don't know if we can even work in the model that we had kind of wanted to pioneer.

Yeah, you just built out this beautiful space.

So now it's like a really hard decision around, like when are we going to get a vaccine? When can we even occupy that space safely? In 2 months, 12 months, 3 years? We can't pay rent for that long and wait to find out. And so that was. That was a really difficult time period because it's. You're in market with. With a product that people don't want. And that's maybe the closest that I can come to relating to entrepreneurs that bend in the wind of irrelevance and see a product they've put all of their soul and energy into not get the response that they wanted. And now they have to kind of confront that and iterate their way out of it.

What's the version of iterating in that scenario?

For me, Yeah. I think it was realizing that I could not raise a second fund without the conviction of a competitive strategy. And again, a friend reminding me, like you said it best, simple beats clever. Go simple.

Mm.

What's simple? No outside capital. One lp. My wife.

Was there a moment where. Did you attach to a fund after that or. No. For some reason I thought you joined another fund. Okay, okay.

And I realized that, you know, it's better economics, a more authentic voice with founders. They knew that I had 100% skin in the game.

There's no question.

And I also felt the purity of, like. Well, I'm gonna say what I think now, because I'm not trying to triangulate.

Did you feel constrained by the outside capital?

Well, you're representing a firm.

Yeah.

You're representing a current and future partners. You're representing a design studio. You're also triangulating to LPs. Very different than me being able to say, this is what I believe. And you can take it or leave it. It's your company right. At the end of the day. But I want to be the most valuable angel on your cap table. And I want you to say that to me and believe it and say that to everybody. You know?

Yeah.

And I felt like that was a simpler competitive strategy.

Did you over complicate your investing process and decision making in the constraints of a. Did you feel like you were a bit of an investor?

No. No. Running a fund? Yeah, definitely not, I think, because, you know, the. The constraints around ownership allocation and bogeys. Right. The commitment to figuring out, like, okay, with every investment, we want to see, is this a new iteration of the design studio? And then how do we kind of, you know, fold that into the narrative, into the sales pitch and especially in competitive deals that are fly by night and where you may not necessarily have ball control. And I think I'll go back to the portfolio construction math. You have to be able to reason with it and say that like this very large investment will return capital, like will get us into carry. And if I can't make that math work then like, why are we even continuing to talk to these folks? That was really hard.

Did you find you wanted to invest in things personally that you couldn't do through a fund because of those constraints? Oh, interesting.

Or we didn't have the band aid to invest in, say like Robinhood Series B because we had raised a seed fund.

Sure.

And it's like, oh man, inconvenient timing, you know, next time. But realizing that maybe our offering, maybe our Happy Meal was better suited to later stage teams and we just picked the wrong stage.

But you didn't feel like you had permission to acknowledge that and be like, oh, let's play around with the model and try the Series B and that engagement mode.

We had to at the end of the day, kind of find a path to returning capital.

Yeah.

You know, and we can take these like small bets along the way, but like they were not going to be the ones to meaningfully return capital.

Yeah.

I felt like there was a complexity bias rooted in that business. That was not true to me. That's not who I am.

I love that so much. I think people undervalue how important it is to put yourself in the truest position you can for who you are and what you value and what you want to bring to the table. I think so many people make compromises knowingly and unknowingly and have a deeper respect.

Respect for people who choose venture as a profession, it's like a whole new toolkit. I'm very grateful for that experience.

Yeah.

You see how the work is done and what motivates it. The whole ecosystem makes way more sense to me now.

Really?

Yeah.

Okay.

Yeah.

What wasn't as clear, I mean, to.

An operator or to an angel, it's not self evident that you want to be constructing vehicles to increase your revenue stream, to be able to build your empire and be able to frankly like magnify the outcome of your best investments. Right. So yeah, that definitely increases your leverage, increases your power over startups. If you are power hungry, that's a great way to achieve power. And there's nothing wrong with that.

Your power satiated.

I don't know if that's what I would.

What would you say? How do you think? Governor of California? Well, I mean, clearly, Clearly I realized.

That venture was not the shortest path. But you realize that there is so much of the bad behavior or the artifacts of venture just. Yeah. They stem from how the system is constructed to benefit LPs and the firms deploying the capital.

Do you feel like you advise founders differently on your own than you would have as a fund in terms of how to navigate the fund?

Because I'm more risk forward now. I'm okay with giving bad advice. We're like at least being a little bit more opinionated.

You were. You held back.

Yeah. Again, because there is a little bit of a.

You're still selling.

Yeah. But as a fiduciary duty that comes alongside it. And again, I keep going back to having 100% skin in the game. I don't want to see founders lose. And I want to say what I believe and I can stand next to because it's just wrapped up in my head. It's not triangulating with other parties either inside the firm or outside the Firm or my LPs or what have you. And then you can be involved with teams that you admire irrespective of stage. That's one thing I did appreciate about multi stage firms. Yeah. You can meet founders, what they are. That's great. I love that. That's simple.

Now that you aren't running a fund, how does it change your ambition for the investing you do? You seem like a very ambitious guy.

I think I wanted to be in service of, you know, this personal mantra of advancing the state of design and tech. I feel like that is a unique way in which I can contribute across different generations of companies and across individuals. One of my happiest days here since we moved back was, you know, back to back meetings with people I've known for years and being able to reflect on not just my arc, but their arcs and where they were and how far they've come. And that was so unique from all my prior experiences in London, where a lot of those days, those work days were meeting new people, that they also made me realize that the privilege one enjoys from being in a tech sector or in any sector for long enough to be able to help shepherd people into breakout roles. And seeing them thrive and exceed all your expectations and being like a small Jiminy Cricket along the way, I find that extremely gratifying because within that set there's some folks that like my parents, immigrated here and they're having American babies. Right. And who knows, maybe those kids will go on and have progeny for generations to come. I can't think of a better way to Pay forward. I just can't. Maybe writing science fiction or making movies is another way. Maybe being governor of California is another way. But for the time being, it's, it's, it's a way that I know I feel confident I can contribute. And I like helping design leaders peer on corners and feel like they've got a wild card.

Is the basket of those design leaders ready to step into entrepreneurship increasing?

Yeah. That's like this funny nexus of people who don't want to become career managers. They either want to join new startups or start new startups. And so as an investor, that's a great place to be. Guys, Colin Dunn, right. I hired this guy away from Facebook to Dropbox because he was the only new grad working on a mission critical project over at Facebook and that was a bright red flag. We don't put new grads on key initiatives at Facebook. That's not a thing. He joined Dropbox, did incredible work there, did a bunch of startup tours of duty. I convinced him to join as head of design at Universe, a New York portfolio company. And then when he was ready to go start a business, I'm like, Colin, dude, I was. I don't know if I'm your first check, but dude, I'm in. I've been investing in this relationship for so long and this is like the culmination of your whole career and you've always had that attitude of like you can't do it. You know, I love that stance. You have that self confidence that is so essential, so vital. We'll see how he does. But I'm incredibly optimistic and that to me is like the purest form of venture. Right?

Totally.

Like nobody snuck in on that. Right. That this is years in the making. And so if you sort of look at all these relationships as culminations, I think that that's a, that's a unique way to live.

I feel like venture is so rooted in patterns. I'm curious if a successful design founder matches against a different set of patterns than say like an engineering or a technical founder.

They obviously would tend to have a higher penchant for tape and quality. Certainly for novelty.

Novelty.

Yeah.

That's interesting.

Something that's visceral. Viscerally different.

Yeah.

They like their products to be more put together. They have this, this bias towards thinking very holistically, which I don't know if you're free within with like, like sort of looking at founders as a set of people.

Yeah.

I think designers tend to try to create a frame that is holistic.

Okay.

Like, really good designers have this natural bias of, like, how does this decision sit within the frame? It's like a good architect is considering the whole structure and how you move through it day in and day out to decide where to place the door. It's like, it's not a decision in isolation. And so I think that's how they approach company building.

Are the best design founders solo founders, or do they have co founders? This is another one of those, like, biases in Silicon Valley that seems very, very real and dogmatic, like selling into government or other things.

Yeah. I don't understand the, like, forced marriages that we have kind of created a culture around. Like, I think YC really encourages people to have co founders. I understand the rationale, but I think it's such a.

What is the ratio? What does the rationale miss?

It misses solo founders that have the verve to do it themselves. Again, I also have strong confirmation bias here. Right. Like, Facebook had co founders, but there was one chief executive, there was one master and commander. Right. And so to me, those startups are great because they're so orderly.

Yep.

It's like, oh, yeah, you know how things are done.

Yeah.

Right. At the end of the day, it's sort of built into the structure of the business. So I have a. I'm really comfortable with solo founders or at least preeminent founders and side co founders with designer founders. I'm not sure if having a. I've got, you know, I have more data to share in a couple years on that front, but I don't think there's anything intrinsic to whether or not you need a co founder to be successful. And I think the dirty secret of Silicon Valley is that a lot of startups fail or succeed in spite of founder dysfunction. Founder dysfunction is like merito dysfunction. It's structural. It's really hard to troubleshoot in good times and bad times. And I think that when an ecosystem kind of insists that you should find your co founder by default, it encourages people to waltz into very important relationships with very little data to support the success of those relationships and very little infrastructure to support how two people coexist and co grow. And what is an extremely challenging time period, you're sort of setting people up for failure.

Like, one of the most challenging times. I mean, just an absolute crucible.

It's like get married and go on Oregon trail.

Right, right, right.

Why would you expect that to work?

How's that going? Right.

Like, do you think everybody's gonna be like sunshine and rainbows?

Right.

Like, maximum productivity or is there gonna be like a lot of yelling, a lot of, of stonewalling, a lot of resentment, a lot of anger, you know? Yeah. So I'm much more comfortable with the solo founder configuration, personally.

I get that. Well, what about an age we're entering now where your co founder is probably just going to be an agent?

That's a great question. That's an excellent question. I think that one of the things that's fascinating to me about this world that we're sailing into is that people are spending more and more time talking to intelligent machines and their own friends and colleagues. And so in that world where the machines have infinite patience and wisdom, they're funnier than any of your friends are. Right. And they're increasingly knowing more about you than you even know about yourself.

Right.

How do humans compete for attention and time and energy?

What do you think?

I don't know. I just know that people who are earlier in their life will dedicate energy towards voices and minds that are infinitely patient and accommodating and funny and wise. Right. And that take them seriously. But I don't know if that will set people up to deal with the adversity that I think will be inherent in life.

I feel like you're wrestling with some of the knock on effects of what's happening right now in public framings like this, but also framings around what happens when we automate away or remove meat from, you know, the blend of things that are going on right now. Where's your head on that? I think you're also, I mean, at the same time you're wrestling with it, you're funding.

Yeah, yeah, yeah.

This wave that, you know, that is either the answer to or the source of.

I think that anybody who is advancing the state of the art and is asking themselves these questions has an obligation to ask these questions in public so that people understand what these downstream consequences might look like. And they are very political in nature because I think it suggests over time that we don't have an economic theory for an economy that has non human action that does not exist. Right. And so we're kind of creating a new economy where previously all economic wealth can be traced to human desires. Pierce through the corporate veil, you will find the trustee, the beneficiary, the corporate overlords, the stockholder sitting there with their respective desires. But now we're introducing economic actors who have very different desires than humans do that are sleepless. And I worry that we are going to create the ingredients for political revolution if we don't have a clear vision for how human society continues to participate in this new economy where our economic competence is suddenly much smaller, where we start to feel like the colonized island to the British Empire, where there's economic like forces happening upstream of me and I'm sitting downstream of it. And I can participate in it in these specific ways, but I can't ever begin to fool myself thinking that I can sit at the center of it. Right. And that's how I think a lot of people intuitively feel already. I think that's right, but I think that's going to magnify with time. And so we need to be able to paint a picture. And this is where I feel like sci fi is quite compelling. A place that occupy paint the picture of. Well, what does that even look like in practice? How can it be desirable and fruitful and aspirational and weird. Weird enough to motivate a future generation of technologists and contributors towards this world.

So how far along are you in the script?

Far enough to pitch it?

I don't know. Let's go. Is it in the briefcase?

Amongst other things, yeah.

What's it. So what's the. What's the script?

It's a little indirect.

You can cut it out if you want.

That's the pitch.

Dude. Don't you want to see this?

Our new media?

No, this is. Yeah. Wow. How does it end?

Oh, I can't tell you that. First check in. Is this an indie vc?

Yeah, Indie productions. No, but I mean, it actually does introduce what I feel like is a real failing of this new technology and the technology movement of AI, which is like the storytelling around it is terrible.

Yeah, 100%.

It's completely devoid of any personality, any vision, any. It's kind of, you know, it's like we unlock the possible and then we explain it in real time versus painting the broader picture of what this is all building towards. And so this, I mean, this is the part of the storytelling that I wrestle with on the indie stuff. It's like, I think people think about it as fundraising. It's not about fundraising at all. It's about like you as soleo. Everyone would say you need to start a fund, you need to hire a team, you need to do this, you need to do. Look, you've ticked the boxes. You have great angel investments, you have the pedigree of these companies. This is your next natural step. You. You say that made me miserable, like I wilted in that environment. I didn't thrive. Where I really work is going to be something that makes you all completely uncomfortable because you can't control me. I'm off here. I have my own resources. I'm doing this all on my own. And I. That's the part of the indie story that I want to get out. That's the part of it where I'm saying it actually has nothing to do with your. It has very little to do with your cap table. It has very little to do how much of how much fundraising them. It's about how do you create vehicles for you doing your absolute best, most unique and informed and wild work. Because everything about the way we've structured the startup world right now wants to wring that out of you.

Yeah. And I think what's interesting to me about this thesis is that we're now at an inflection point where before, you know, a year or two ago, the entrepreneur was heavily reliant on people to self actualize, to get anything done, you would need the investors, you need the employees, you would need a lot of people in your life to self actualize the big movie set. That's right. But the movie set of tomorrow sits inside of here. That's right. And here. And what I say to the machine, no cameras.

That's right.

No set. And so what's interesting to me about what you're working on is how do you champion the person who wants to just go solo in almost a purest way, almost in an extremist way. We're like, how far can I get before I have to actually start to wrangle with people and employees? Right.

I think that's been one of the funniest things I wrestled with. You know, part of this video was the video stuff happened because I couldn't write, write any more about indie. I was like, I've. I feel like I've said everything a thousand times and every time I write it, someone interprets it through their own lens. They project onto it their own thing.

Yeah, yeah, yeah.

And so I put off writing our website forever, which is what took us down this video rabbit hole. But when I finally wrote the website, we have, we have two sections. It's. We have facts about us and then vibes, which is ridiculous. It's self admittedly ridiculous.

So Gen Z of you. Oh my gosh.

But the facts page, what I found interesting is there's only two things people take from all of this. Like I anguished over this freaking page forever.

Yeah. What's memorable?

Two things. We're more a 24 than a 16Z. So we have that line, I Like.

That, That's a good one.

And then we have, there's a, there's a paragraph in there where I say 100 million in revenue with less than 10 employees is this generation's 4 million 4 minute mile. And once someone figures it out, it's gonna do just like what the 4 minute mile did. Now you've got people running sub 2 hour marathons. It just really like similar to the corks it uncorks. So similar to the design founder who has a wild success. And now people can point to that and say, oh look, somebody who actually is just like me.

Yeah, yeah.

Can do this.

Yeah, yeah.

I feel like that's where what we're on the cusp of, and that's pretty core to what we're thinking about and working towards too, is like, how do we, how do we push that idea?

Yeah. Sometimes you have to show people bad examples too, or like, like borderline contemptible examples. One of my favorite books, I've read it twice, not to my kids, is Watership Down. And it was a neoreligious experience for me to go to Hampshire, England and see Watership down is a real place. It's like an ash place. It was a religious experience for me. It was a book that was written by a man, first time author, and he conjured up the story on long road trips with his daughters. And he loved the story. It was about two rabbits, one of whom had a vision that something bad was going to happen to the warren. So what do these guys do? They flee the war and start a new warren. And that is the whole genesis of their journey. Right. It's an incredible book. Right. It's hard to even describe. Don't watch any of the movie adaptations. They don't do it justice. Read the book, read it aloud. The reason why the book got written was because these daughters just kept badgering this guy to write this book. And he was like, I'm not an author. That's not me. And then one day he found himself reading a book to his daughters and he was like, this is trash. I can do better than that. I can't believe this got published. And all of a sudden it was like, it went from like, I can't do this to like, this person's contemptible. Yes, I can be better than this. If that person could do it, I could definitely do this. Right. And sometimes, sometimes, you know, the world moves forward because of spite.

There's the ending quote right there. Oh my God. I show him. Yeah, I showed him the notes on the. I had, like, 50 things I wanted to go through, but. And I derailed them all. No, not at all. This is. This is like, we covered two or three of them.

That's fun.

So this is great.

Hopefully this.

What a weird, funny way to start a relationship here. Like, this is better than a coffee meeting.

Well done, by the way, on this venue. I think it provided, like, a timeline for me.

Yes.

Just the movement of the.

So isn't that fun? It's one of those kind of unintentionally.