Designing the Facebook Like Button

The like button is funny because it feels like being known for designing or drawing the Mickey Mouse ears somehow became extraordinarily iconic in a very specific cultural way. And little did I know how much of an impact that would have on essentially the structural engagement of Facebook, reorienting it around newsfeed specifically. But then long term, the cultural resonance that gesture would have. And we had experimented. We had a thumbs up icon, we had a heart icon, a start icon. But because of poke and because of the universality of the hand as a visual symbol, it just felt very Facebooky to use a hand. And so we went with that. And. And I get way too much credit for being the designer that oversaw, like, the final version that actually saw the light of day. But I'm happy that my name is on all the commits. And yeah, it's. It's one of a thousand things I worked on at the company.

Folks, thank you for tuning in for another amazing episode today. I've got an amazing guest, Soleo. He's someone I've looked up for a long time. He's. To me, he's a legendary designer turned investor who's invested in a lot of amazing companies, the biggest one being Figma. And what I want to do in this interview with him is figure out behind the scenes how he became a VC from being a designer on his own terms and then what makes him unique in the way he operates and stuff. So we're going to take a deep dive into that. Welcome to the show.

Thank you so much for having me. I really appreciate it.

You were so gracious with your time. Like you spent like more than an hour with me at Figma Config, where we finally met in person. And the time that you spent with me, that one hour that could have been spent with somebody else. So you were missing out on something by talking to me. So how do you deal with that phone? Yeah, I'm talking with Jay. But then I'm missing out on some potential other founder who creates something big.

For one, I, I always appreciate when people are eager to talk shop and ask great questions. And at least for me, I don't experience the opportunity costs when somebody has prior context and more importantly, they bring some interesting questions to light. Because in that process, I think I learned something too. And one of the things that I have always appreciated as a lesson in life was from a next door neighbor of mine who had written some 24 odd books on the mind. He had studied the mind in Los Altos, California for 40 some years and written a bunch of books. And one of the things that he tipped me onto was this idea that you find folks who can ask great questions that can help you navigate the forest of your own thinking and your own life experience. And I've always thought that was a beautiful metaphor because you become deeply familiar with the ins and outs of your time on this planet and you can sometimes overlook the parts that are not self evident or not obvious to people who haven't shared that experience. And in some respects, even hearing the paths that other people I've looked up to have taken were inspirational to me and informative to me to understanding like what one can potentially do with their time on this planet. And so I appreciated your gumption for just coming over and saying hi. I think sometimes people are too shy to a fault and secondly asking terrific questions.

Thank you. And the reason I'm asking this question is I'm trying to figure out if you have like a framework where maybe there's some hoops people have to jump to FaceTime with you. Maybe there's a framework where you evaluate spending time with this person the best course of action. So out of 10 people reaching out to you, how do you prioritize? Like you said, you have limited time. You can't multiply yourself and give time to everybody.

It's a good question. So I work as an investor in London and the majority of inbound that I get is typically through either warm introductions or warm requests and just old fashioned email and dms. And for me what I typically do is I take advantage of clever automation to help triage and organize cold inbound into pipeline talent and other kind of non work related inquiries and then figure out how much I can field asynchronously. I feel like there's a school of thought that I think Eric Schmidt, the former Google CEO, pioneered, which is you can respond to an email now, do so, don't wait to have to deal with it further down the road. And so there's a little bit of whack a mole there, but I find that just quick written responses are a great way to give people the timely attention that they deserve, but also to reduce the likelihood of having to fill up the calendar with random coffee dates. And in the case of attending config, I actually found that it was a an opportune time in which to meet with a whole host of folks who I hadn't seen for years, many of whom I hadn't seen since before the COVID pandemic all in one place. And so I leaned into the possibility of Being able to just replace dozens of one on one zoom calls or coffee dates with just an impromptu walk through Moscone center and in the process getting to meet people who I hadn't met before, like yourself, and fully embrace the idea of that venue and that, that opportunity to have impromptu gatherings and reunions. And it was really heartwarming to get to see so many people. If I sat down and made a list of all the folks who I saw, who I've known since before COVID that I got to actually like, interface with on just one day of attending the conference, that number would easily be over a hundred. And it was, it was, it had a really incredible high school reunion vibe to it. Many of whom like colleagues that I spent hours, like days, months, weeks, years of my life working alongside. And so it was, it was terrific to be able to, not only just to catch up with the broader Figma family, but to see a lot of former colleagues from past tours of duty. And so the framework for me is just where possible, organize all inbound, structure it so that you're prioritizing the things you have to. I do them. Responding to portfolio companies much more rapidly than cold inbound and set clear expectations with folks that why spend 40 minutes on a call when we can potentially save ourselves the majority of that time and actually have much more to show for it just by going back and forth over email? And that's true with not just designers, but with entrepreneurs with other investors. I find that encouraging people to seek out asynchronous communication just expedites a lot of that chit chat and lets you drive straight to the heart of the matter.

I'm trying to imagine like a Thursday where you're just flooded with requests and portfolio companies. You've got all these cold inbound coming in, there's some fires you're trying to put out, you've got a family, so maybe there's some stuff going on with the family they got to deal with. I'm trying to put myself in your shoes and it feels extremely overwhelming because it's suddenly the sheer quantity of so many requests, replies, emails, intros, decisions you have to make.

Hey, you're stressing me out, man.

I'm getting stressed out. So I'm trying to figure out how do you not get overwhelmed? What do you do in that situation when everything is just running on all, like fifth gear, all of those things.

Yeah, a lot of stuff. Concept has resolve itself on its own. I found that was one of the lessons I learned as an operator that sometimes if an email doesn't need to get responded to in 24 hours and you don't necessarily have to. And in many cases it sometimes self resolves. People find their own answer or they were able to figure it out. I think the other piece is just again knowing like what is critical. There's a simple heuristic question of will this matter in a year that I learned at Facebook actually of all places, where there was just a similar kind of dynamic where there's internal discussions to track and a pull request that I have to review and somebody's doing something goofy on the website that I should probably chime in on. And I stumbled into this simple heuristic of asking the question, would this particular decision or this matter have any consequence a year from now? And if the answer is no, then that's often like a pretty good sign that it can be lower priority than other matters that are consequential, that they do have some sort of strategic or structural import, like a hiring decision, right? Or launching the name of a product that will be really difficult to unwind or change further down the road. And so those are the things I try to look out for with whenever there's overwhelming inbound. I think the other piece is just getting really comfortable with setting expectations and especially when the expectations are like, I don't have time for this or the best person to answer this right now for you, a simple no, I am not interested in doing this right now. But that's tricky. I think part of it's maintaining some crisp set of expectations with the people that you service and ideally honoring those as best you can so that people can think of you as a reliable agent out there in the world, somebody they can count on. I sound very serene and Zen about it, but I don't think I get it right 80% of the time. And part of it's also that is adjusting as needed. And there is firefighting and that's part of the job as well. In some respects, living in London has helped quite a bit. The expectations from like when I need to respond. And so that kind of gives me a little bit more agency on the prioritization of the day versus being located on the west coast. By default.

You have a way of just gently doing things. Even if you were to say no, my guess is you would do it in a way where it's not harsh. I'll give you an example. In over communication when I was interviewing for the podcast, you could have easily just being like, here's my calendar link. Book something on it but the phrasing that you used were, let's find a time that works for both of us. Which means is to me, you treated me at the same level as maybe a general partner at Benchmark, like some of the top VC firm, like you held me and some other successful person at the same level. There's no differentiation based on someone's qualification.

Right.

And to me, that's mind blowing because not everyone does that. The way people behave changes on the person's title and stuff too.

Yeah, I don't know, I. I actually don't mind receiving the calendar links because it gives me a lot of agency and so I'm always happy to be downstream of the calendar, like, rather than having to. To service it or give it to other people, which feels a bit more binding in some respects. I think in my mind it's just, there's a simple golden rule, like, treat other people how you wish to be treated and don't take people's time for granted where possible. I don't like when people waste my time, so I try to project that onto other folks and assume that they don't like it anymore or less than I do. In a world where we spend a lot of time online, I think there is a declining art of diplomacy and I think people do appreciate that approach.

And speaking of Facebook, man, you are the person who designed the like button. You hold a patent for it, and that design has impacted billions of people in the world. Like, I've used the like button. Like, the first time I remember using it, it was insane. So can you just walk us through what was that moment like, where you came up with the idea, okay, we should do something like a like button. And what was that feeling like you for as a designer?

The like button is funny because it feels like being known for designing or drawing the Mickey Mouse ears somehow became extraordinarily iconic and in a very specific cultural way. The honest answer is that the like feature was not conceived by me. That's the honest to God answer. Any more than I think that any one person conceived of the iPhone. Even though success has many fathers, the like button was really just in the zeitgeist of the Internet social services and at. At Facebook. It was a clever stuff of it. An idea of, oh, yeah, we should have a simple button that people can push so they can stress that they like something. They find something that's awesome on the site and that would be helpful to them, helpful to us. And so a, A team, I think it was in 2007, came together at a hackathon. And they worked on this, this project, they like built it, they shipped it internally and it just got stuck there in product purgatory. And I think one of the things that most people forget is a lot of features, a lot of product development at Facebook fell along this track where like we would build stuff internally for internal use. And sometimes it just didn't really resonate within the company or with leadership and it stayed there and got sunset or just never really saw the light of day. I think it was Microsoft who coined this. They call it dog fooding. Sometimes the dog food didn't taste great. The awesome button, which was the code name for this project, was a bizarrely cursed project because it always just found reasons to not go out the door to the general population. Either the design was a little bit too goofy and it didn't clear zuckreview, or there wasn't like anybody kind of driving it to completion, or there was a lot of like over intellectualizing. A lot of the company leaders would sit down and argue about whether or not a like button cannibalize conversation on the platform. And so we had a fits and starts of people trying to ship the like button and it getting stuck in product purgatory at Facebook. I think it was at the end of 2008 we staffed a project that we called the UFI, the Universal Feedback interface. And it was broader regime to bring about a set of changes to Facebook. The first was that we had years of commenting code across all the different products and features that we had built that needed to be standardized. We needed to have one component for how it appeared to the end user. One point of integration into privacy, into newsfeed, into all the algorithms and ideally like an interface that could be hot swappable across different contexts. A universal feedback interface. And so as part of that initiative of overhauling the commenting system on Facebook, we thought it would be also a good opportunity for us to introduce it into Newsfeed itself. Because up through that point, Newsfeed was like a read only interface. It was just a daily newspaper or daily like news site of all of these stories that are happening in your social circle that you could just click into and it would take you to another part of the site. You really couldn't do anything on newsfeed itself. And so the idea was that UFI would be able to allow us to introduce feedback directly into Newsfeed itself. And the UI that I came up with was this essentially like little pool of blue that would appear as a visual cue for Feedback from the network for any given post. So you're scrolling through newsfeeding, you see this little pool of blue appear whenever comments or feedback would appear in that context. And as part of the ufi, we thought, okay, it's probably a good opportunity for us to finally ship this damn like button or at the very least run the experience. We need to dampen the all the debate club that was happening at the company about whether or not it was good for Facebook or good for users, good for engagement, good for conversation. It's let's just like ship this and gather some data at the very least. And so we rolled out the like button as part of the UFI and the broader NewsFeed redesigned in Q1 of 2009. We chose two pairs of networks where there was high friend density, meaning that for any given member of that network, the majority, vast majority of their social sphere or their social graph were other members of that network. And at the time I was living with a good friend of mine, Jeffrey Wieland, who is Icelandic and I'm Colombian. So we thought, okay, Colombia and Iceland have high network density. We're going to ship to those two networks and the controls are going to be, I think it was Venezuela and Norway if I recall correctly. And so we rolled that out for a couple weeks, compared the data against the two networks, and found that contrary to all of our product intuition, the like button actually increased the likelihood of people commenting on a given post, that it almost acted as like a social lubricant. It gave people permission to leave a comment because they would see this little blue pool appear beneath posts that gathered feedback from the network and that clearly were resonant. And people were far more likely to leave a comment if some of their friends had already liked that photo or that post. And once we saw that firsthand, we realized, okay, we should go ahead and we should ship this worldwide. And little did I know how much of an impact that would have on essentially the structural engagement of Facebook, reorienting it around newsfeed specifically. But then long term, the, the cultural resonance that gesture would have. And we had experimented. We had a thumbs up icon, we had a heart icon, a start icon. But because of poke and because of the universality of the hand as a visual symbol, it just felt very Facebooky to use a hand. And so we went with that. And, and I get way too much credit for being the designer that oversaw, like, the final version that actually saw the light of day. But I'm happy that my name is on all the commits and yeah, it's. It's one of a thousand things I worked on at the company. I never imagined that would be the thing that much like Mickey Mouse ears, that would be the thing I'd be known for. I'm much prouder of other things that I worked on there, but I'm happy to have helped break the curse of the awesome button.

Oh my God. And for someone looking from outside, it seems like your career is so linear. Like you had everything figured out. Like from Facebook, you went to Dropbox, became a design leader, then raised your own VC fund. Combine. Everything is so linear, like step by step, you just are gradually going in that direction.

I think maybe I presented as such, but it was very much not linear. Most folks don't know this, but I left Facebook in November 2011 and I didn't join Dropbox until December 2012. So 13 months later, there's a little bit of a gap in that cv. And when I left Facebook, I, I realized that the world was broad and sprawling and there's a lot of stuff happening way outside the company's purview. But I had a lot of friends that had moved on from Facebook to work on their own startups or to finance new startups. And many of them reached out to me that first month with the same question. They're like Soleil, you guys did such an amazing job with hiring for design at Facebook. How did you do it? I'm trying to hire somebody to do design in my company before I run out of seed financing. And this is like the principal bottleneck in my startup. I don't know how to source, I don't know how to evaluate. Can you help coach us on what we need to do? And I had really strong opinions on the matter because towards the back half of my time at Facebook, I did a full 180 on recruiting and realized that that was the most leveraged thing that I can do at the company to help identify and attract exceptional software designers and convince them to stop what they're doing and join us in Palo Alto and made some pretty epic recruits along the way. And, and I had strong opinions on the matter, what to look for, what made an exceptional software designer. And so was happy to share those opinions with my friends who are financing or running their own startups. And in the process, those conversations led to both, like how I met the Dropbox team, how I became an investor in a company, and ultimately how my role as an advisor and investor to Dropbox spiraled into a full time job where I think Drew Houston Convinced me to join because he was like, dude, you're basically sending us emails seven days a week. You might as well take a paycheck. And I'd help complete some of the hires that we had made up through that point. And I realized he's right. This is a great opportunity for me to run a team that I'm helping to build in real time. And he's also right. Yeah, this company is eating up a lot of my head space. I might as well go all in on it and support my investment in that way. And so that's how I ended up joining this head of design at the end of that year. But those were two very separate decisions. It wasn't one of those things where I went from one to the other. And in between those two decisions, one of the best things that I did was listen to a mentor of mine. He had suggested that I structure my week according to different initiatives that I was really excited about exploring. Just basically Monday be X Tuesday be Yellow Wednesday bz and see where that takes you for a couple months. And so that's roughly what I did. And in that process, I realized that working with startups and helping them build design at their core through a mix of design recruiting and mentorship and feedback on product strategy and diving into design reviews, those are the things that energized me and where I felt like I can have the most impact in the next stage of my career. And so that's essentially how I became an investor. How I learned that was a role in the world, that people advised startups and that I can be a company advisor to great breakout businesses like Dropbox and later Figma.

So you mentioned Drew Houston. This is so funny because I live in Dallas, Texas and it's isolated from the tech hub of someone who lives in the Bay Area.

Yeah.

So I remember there was this invite only designer Fund event and obviously I'm not there, so obviously I was not invited. But I'm like, how do you break out of this? So literally I flew to San Francisco next day. I'm like, I'm just gonna go for the event. So like the where Designer Fund is basically, it's gated. Like you can't enter it if you don't know someone, but they have a window on the ground floor. So I just threw a rock there. And then Enrique Allen just twisted around and he. Who is this guy? And he came out and I had my suitcase and I was like, hey, I flew in from Dallas, let's just say hi. And then he was very Nice. Invited us in and then the event was happening at Dropbox and that's where Drew Houston came out. And I think he was trying to meet somebody and I just started chatting with him and he was super nice and stuff. So like, it was like a fun moment. Just like this friend, a video stuff. Just because you mentioned it.

Yeah, Drew's great. I actually, I always appreciated. One thing I liked about Drew is he, he was clearly energized by recruiting and so he never backed off from helping out with closing candidates or talking to folks and getting excited about Dropbox. He's very hands on in that regard. And for anybody who's into talent spotting and recruiting in general, it's very affirming when the CEO is willing to roll up their sleeves and get into like empire building mode and helping out with closing candidates. Because I think to the end candidate they appreciate that it's like for the CEO to come and talk with them. It's meaningful. You're not distracted away from that individual, especially if they're going to be the beneficiaries of the lion's share of your work. But then I think too, they want to hear directly from the keeper of the vision and the strategy, why does this company matter? Where's it going? And Drew was really adept at taking his ideas for Dropbox and rolling it into a recruiting narrative that was really well targeted. And so I always enjoyed working with him in that regard.

After Dropbox, you started combine. Raise your own VC fund.

Yeah.

Why raise your own VC fund? Why not just join an existing big VC firm like I know Andreessen Horowitz or Sequoia or Benchmark as a design partner, Go your own route.

I'm not much of a joiner, to be honest. I've realized about myself, I think it was a combination of things. One, we had wanted to explore a very different model for venture and doing so in the auspices of an existing venture firm. It's just tricky, right? It's like joining ETA to be a venture partner in that context. Right. So I, I didn't think it would give us the latitude to experiment with what we wanted to do. But I think too, we thought that if this model could be really successful, it would be wonderful to be the principals and the owners of this model to be able to extend it further. And I think the other piece is there's some benefit from a branding standpoint to have a highly differentiated offering sit under a highly differentiated brand, at least relative to all of the other existing VC legacy funds that were out there. We thought that there was potentially room for a new one. And so that was the thinking behind it. And very much early on it was a hybridized so combine, the whole Concedo combine was how might we combine a early stage design studio or venture studio with an early stage venture fund? And how might these two operating models potentially attract really compelling investment opportunities that would be very different from a similarly sized microfund? And so both in terms of the operating model, but also the business model were radically different. And we learned a lot in the process. And I also, I think it was very beneficial to me from a learning standpoint because it taught me what it actually takes to be a fund manager and a VC and how VC actually works in practice rather than from the vantage of a spectator or a constituent in the ecosystem. And I think that perspective definitely helped me understand the reasons why that might not be a long term fit for what I want to do my time on this planet. And so it was very much a learning by doing exercise. And we had just tremendous support from really enthusiastic LPs who were super helpful in giving us the latitude to experiment with a variety of different ways in which we can work with startups in that context.

Before COVID what I like about you is that you like to play the game on your own terms. Like after the success of Combine, you could have followed existing narratives out there, oh, let's raise a bigger fond, like a behemoth fund or something. But my understanding is now you just invest your own money, you're the only LP in your own fund.

I like to joke that my wife is my only lp.

How did you overcome the powerful narratives like you're doing something that's not normal? Maybe it's, but it's not the conventional route.

Yeah, it's a good question. I think partially it just comes from the scar tissue of raising and managing a fund and appreciating the work that's required. But then the other piece is I was really fortunate in getting to partner with some great teams early on in my investment career, that I might be able to recycle into a more permanent capital base and that the economics were that much more favorable and aligned with founders for me to have 100% skin in the game with the investment activity that I was pursuing. And in many respects it fit the psychology of some of my earliest investments where I didn't have to rationalize it through the lens of an LP memo. I can just make conviction bets based on intuition and conviction. And I think I reached a point in my career Where I was just done apologizing for my own intuition. Because in many respects, if you're an early stage investor, whether or not you have LPs, that is like a big part of the decision making process. It's why LPs give you money, is to use your judgment and to use your intuition on how to size up a founder with a very limited amount of reps and inputs on whether or not they have the verve and the vision to build transformational companies. Deciding to go the solo GP or like the angel investor route made more sense for me from a economic standpoint, but I think also from a differentiation standpoint. I think founders appreciate that I'm not scouting. They appreciate that what I say is coming from the perspective of this is my capital and I care about it 100%. And then I think secondarily they appreciate that the role that I can play in a broader ecosystem as someone who can back channel and route opportunities to lead investors and whose warm intro I think matters in that regard. Right. If I say that I made it a commitment to invest in a particular round that carries a different sort of signal, especially if it's a substantial check or if it's a high conviction bet. And that's given me also the latitude to pursue other endeavors as well, to support my wife and her career as a theater producer out here in London, to live in London, and also just to be able to ratchet up and ratchet down as I see fit.

I promise you, the next time I'm in London, we will try to make it happen where we go and visit the Arsenal Stadium or just see a game or something.

I actually went to my first Arsenal game a couple months ago with a decent friend of mine, this guy, Akil Wably. He and I were in the trenches of Facebook and we worked in a variety of projects together. We even had our fair share of fights. Not like blows or cage matches, but we were on opposite ends of a decision. It almost feels like a band of brothers vibe with him. But I hadn't seen him in almost a decade and he moved to New Delhi years and years ago. And he reached out to me a few months ago saying, hey, I'm in London on a dime and I want to go to an Arsenal game. Cause I haven't been to an Arsenal game and team's actually good. And I also realized it might be nice for me to hang out with you. You want to go to the game with me? I'm like, yeah, dude, I'd love to see you. The game sounds Great too, but be great. Be awesome to hang out. And so I got to go see my first Arsenal game and they clobbered leads and so it was a great win. It's fun to watch him watch his team triumphant again. It was really good.

Oh my God. I'm a big Arsenal fan. You invested in the seed round in Figma. Would it be fair to say that is your most successful investment to date?

It's up there. We'll see. I've got other investments that we'll see where the terminal value lies, but yeah, so far it's probably the highest performing. And to be clear, I invested before the Series A and got involved between their 2012 financing when index backed them and then working with Dylan and team to convince John Lilly to lead their Series A. And I got involved in 2014. But yeah, that ended up being a very fruitful partnership.

How does that happen? Did you already know Dylan in advance? You just emailed him, like, how did that really happen?

No, all credit should really go to Ryan Kaplan, who was a college classmate of his. Ryan was working at Dropbox as a software engineer on a major Photos initiative. And Dropbox at the time was in a very acquisitive stance. We were acquiring product teams to help build out our ranks, but also to staff major initiatives like Photos. And so web based photo editor was really top of mind for us as a potential M and A opportunity. And Ryan Caplan's I have a college roommate who's working on a web based photo editor called Figma. And a warm intro later, Dylan Field appears at Dropbox's hq. We go to lunch and I remember Dylan's walking around with a laptop, open laptop. And I think he was like 19 at the time. He was pretty young and he was very energetic. I remember he has, he was just like a ball of energy. And he starts showing me these WebGL demos that I think are now famous. They're like in company lore, like the sphere bouncing around in water and light refractions and all this other very photoshoppy stuff. And I'm like, huh? Why is he showing me this? And I'm like, let's. So why are we meeting Dylan? And he said we were working on a Photos editor, but we realized that's terrible business, at least in, in 2014, 2013 is when we met, I think. And so we're pivoting the company and I'm like, okay. And I'm thinking maybe I should start gearing up the M and A conversation with him right now. And he's And I want to talk to you about it because we're. It's a collaborative design tool. And I was like, huh? Say more. And he starts explaining how this web stack that they had invested their first few years building was not just well suited for real time collaborative photo editing on the web, perhaps even more fundamentally, it was really well suited for editing vector graphics. And he had studied the pioneering work that Sketch had done and felt that a lot of the functionality that Sketch had effectively invented for software designers and digital designers was super well suited for a web based environment. And I remember there was like a click in my head because at that time I was leading a team of 14 or so designers at Dropbox. Half of them use Photoshop, half of them use Sketch. We were dog fooding Dropbox as an environment for collaboration and the whole setup was trash. It was hot garbage. We didn't know what was the latest files. We had redundant assets. Giving and receiving feedback was like not great. And this was allegedly the state of the art for collaboration. And we were working on a collaboration platform. The click in my head was realizing that, yeah, if a lot of stuff lived behind the link, like in the web, that would streamline a lot of stuff. Not just the prompting, soliciting and giving feedback, but the actual authoring of the work could be transformational. It could be like what Google Docs did for knowledge work in some respects. And if you take that thought exercise one step further, I realized that Photoshop and Sketch were both single player tools. They did not reflect how design was done in practice. In practice, what I observed was that we designed as a team. And it wasn't just people who had design in their title. Design was done at Dropbox by a whole range of functions. People design the products, not just designers. And so I thought, you know what, if these guys could convince designers to do their work inside of a browser based environment, this could be an amazing business. This could be transformative. And I was like, Dylan Field, I want to work more closely with you. How do we do that? And so we started spending time together in Palo Alto, which is where the original office was located, mentoring their first designer SPs. And it was a really small team. Half of them were out of Adobe. Incredible graphics folks. Evan Wallace's co founder was like a hundred X engineer. This guy could just make software do what he wanted it to do. He's like the John Carmack of his generation. And I was really bullish about it being the most leveraged way in which to impact design education. Because what I saw as a structural issue with tech. Not just Dropbox, but tech we didn't have enough talent to hire from. And it was because everybody who worked as a designer tech came from some random background. The vast majority were self taught. There were no structural inroads and frankly there wasn't a whole lot of content out there. The tools were not designed to help people reach a level playing field. You had to own a Macintosh just to be able to use Sketch, right? Not a lot of people can afford Macintosh. And I thought that the best way in which to potentially, over the long term, if successful, to revolutionize design education is to give people broader access to other designers to design assets and more importantly to a set of tools that could give them the inroads that they needed to pursue that line of work professionally. And it was meaningful to me because as a teenager I was super fortunate to get hired by a Guy named Dave G.W. scott to work at a communications office in Middletown, Delaware. And he was a one man army. Dave Scott was. Dave Scott was a self taught designer doing desktop publishing. He wrote and designed and printed the school alumni magazine. And he needed an intern and he saw some work that I had done out of a computer lab, working on like a newsletter for soccer league that I managed. And he's, hey, what did you use to make this? This is not like a Microsoft Word document. I was like, I use QuarkXPress, it's on the computers. He goes, you know how to use QuarkXPress? Show me. So I'm like, okay, show him my QuarkXPress files. He's what are you doing this summer? And I was like, probably working at McDonald's again. He goes, nah, I think you should work for me. And I basically was his design intern for a summer editing Photoshop files. He taught me Photoshop how to use it in the traditional desktop publishing sense. Using QuarkXPress in a professional context. It's personal to me because what dawned on me that summer, and I'll never forget this moment, he told me, he was like, you realize that this is what Time magazine uses to make magazines, right? This is what the Hyde of industry uses. And I had not appreciated that. It just reframed everything that I was doing to know that I was on the same level playing field as the people who were producing things that I consume. And for me, Figma offered the promise and I think delivered on the promise of giving people around the world that same feeling. This is the tool that people use to make the software that lives on this right to use the services that I love every single day. This is the same tool that the people I admire use. There's nothing else. Right. And maybe it's because I grew up watching Nike commercials in the 90s, but I appreciated the egalitarianism of that approach and that philosophy. And I felt like the Figma could potentially expand the axis to design to a much larger set of people.

Your first couple of words that you just mentioned, Dylan, where hey, I want to work closely with you. How might we do that? Instead of phrasing it that way, why did you not just directly say, hey, Dylan, I like the idea, when can I write a check? Why did you not just jump to it?

I think partially because, and this is part of the. My overall investment approach is I wanted to get some more time with him and the team before making investment decision. I wanted to formalize the relationship and have some real skin in the game as an advisor. And I think because the check at that point in time was not as interesting to me as working more regularly with him and the team on Figma, I also wasn't sure if it could succeed much. Like many other smart people, I was skeptical that they can create a graphics editor that was performant enough to convince folks to switch from a Mac native app to Chrome and wanted to see first what kind of progress could be made there. And the big bet that the company made early on was on multiplayer as a proof of concept for why the web was ultimately the right environment for a design tool because it forgave a lot of the performance issues and it made subtract that notion into something tangible. And I remember Evan Wallace like demoing multiplayer, the earliest prototypes of multiplayer. Again, this guy was like 100x engineer, one man army. And it was surreal. Oh my gosh, this is the way it will be done. I call these, these Jurassic park moments. I've had several in my career. But it's where it's like that scene in Jurassic park when the baby raptor is hatched. It's like they stopped the tour. And John Hammond's I always want to be here when they're born. That's like why I built this whole fricking park is so I could stand here and watch these dinosaurs come into the world so I can be there. And I find that so relatable. It's like why I love working with startups. When you get to see the first version of a thing that is gooey and harmless and is going to need a lot of work and a lot of growth, but man, it's a predator and this is when it grows up, it's going to eat things. And I love that moment. Right? Because it's as clear as day. And seeing multiplayer for the first time is like, okay, there's something here. This is. If it's not Figma that does this, somebody's going to do this. This is the way of the future right there. And I love that. I live for that.

You know how designers have like portfolio case studies. Like what I love doing with you is all day I would want to do just with you, like investor case studies. Like literally. Tilayo, what is another investment that comes to mind that is up there with Figma and how did you like get on the cap table? It's so fascinating to hear your whole thinking process. Have you met the team? What was that aha moment where you're like, okay, this is it.

Yeah, yeah. It's all so different. Like in Dylan's case, it was a warm introduction. I was one of the first backers of Framer and this is a team that Facebook had acquired through sofa. And Framer was a project that they were already incubating. They're developing at Facebook and decided, you know what, this might be commercially viable. Facebook's giving us only so much lead to develop this in house. If we want to commercialize it, we should probably peel off and go do that. And I remember investing alongside Designer Fund in their seed round. In this case, it was like a jockey bet. These are two great product makers. Exceptional taste. I love their drive. These guys had verve. And more importantly, the mission resonated with me. Their whole idea was like, designers should code, designers should ship. They should feel what it's like to take an idea and bring it to production. They should make their ideas tangible. They're designing for an interactive medium. Why are they generating non interactive artifacts facsimiles of interactive software? And I'm like, this is straight. Yes, I'm in. I don't know if you guys are going to run a great business, but I'm in.

Did you already know the team?

Yeah, I met them through like I think Kuhn was one of the designers to take over a big chunk of messaging, which is an area that I owned at Facebook. I remember driving around in my like old Beamer in Palo Alto, like talking him through the ins and outs of messaging since he was taking over a chunk of that work. Yeah, I knew the team and they were just like two terrific founders. I felt confident in their partnership, which is a big part of an investment decision. You have Conviction not just on the product vision and the business, but on the health of this relationship. It's probably the dirtiest secret of Silicon Valley is how many shotgun weddings are constructed around getting people to co found businesses that may or may not succeed. Because at the root of the business is some partner misalignment or dysfunction that is really hard to troubleshoot, especially when things are hard or even when things are massively successful and you have to make difficult decisions or where people diverge on. In this case, Kun and Yorn, they were like brothers from another mother. Like these guys just, they, their energy was like great songwriting energy. They were a duo and they had worked together across multiple contexts and they had a common vision for quality and excellence and relevance. And just great marketing chops too. I mean, just are really good at getting you hyped and that carries through all the way to the present. And so I was really, I'm really proud of that team in particular because they hit a glass ceiling with the prototyping tool a few years ago in terms of the addressable market. Had to make really hard decisions around personnel and payroll. That is not easy to do as a founder. Right. Parting ways with team members that you spent months of years supporting and bringing into your organization and then having to have that come to Jesus moment of do we sell this company? Do we wind it down? Do we give people back their money? Are we, what are we doing? Do we go again? Do we have the fuel in our gut to go and start again? And so I'm really proud of them for their pivot and how successful it's been because they weren't starting from like a, a clean slate. They were starting from what I would call like a really psychologically challenging space. And they just, they face the headwinds and they made it happen. And I'm just enormously proud of them. And I think I could trace that back to the health of their partnership and their drive for excellence for making something great in the world. Yeah, that came through. And my interactions with them before I.

Invested, I was so grateful they invited me to your, I want to call it like party before config. And there I met Jordan Singer.

Yep, the post meetup.

So funny. Like, I'm asking Jordan Singer, what do you think about like Figma doing something in this space? And then he's giving me an answer and both of you are laughing. And then next day Figma announced that they're acquiring Diagram. And I'm like, oh my God. And you're an investor in that. How did that come about.

Yeah. Jordan and I were like Twitter buddies. Once you're a design recruiter, always a design recruiter. And so, like people, there's a whole quip that trope of you should professionalize the thing that you love to do that nobody pays you to do. Some people like to play wordle. I like to just, like, lurk on the Internet and find incredible portfolios or people just doing awesome work and just, like, organizing them to my CRM and just tracking them. I'm just a talent spotter. That's just, like, what I do. It's. It's sport. And Jordan was one of those folks that he was on my radar years and years ago because his ability to whip up a frenzy around, like, videos that he would tweet out, and it's just like, the visceral quality of his ideas and his willingness to, like, write code and ship and just get things out the door, I love all these properties. I was like, you know what, Jordan? I don't care if you started a soap business. I'll put money into it. Because you just have that drive to ship that's not teachable. And long before I think Diagram got started, I was like, hey, man, if you ever throw your hat in the entrepreneur ring, like, I am happy to support you on that endeavor. Because the world needs more designer founders. I'm glad that Brian Chesky reaffirmed that for everyone at Big. I was echoing that sentiment when it was less fashionable alongside a designer fund way back when. And it's true. I think more designers should really wake up in the morning, look at themselves in the mirrors, and ask, can I find it in me to apply myself as a founder, and can I find the right business and partners to help me in that endeavor? Because designers do bring a particular event towards product development and company creation that's different than folks from other backgrounds. And in Jordan's case, I just loved how much of the early work that he did with Diagram was already out there in the ether. And more importantly, that he was already dabbling in. He's already playing in that space. And so it wasn't like he was just manufacturing his curiosity. Instead, he was just commercializing it, he was incorporating it. And I was honored to support him in that endeavor. And I was thrilled that Figma kept him close and that they were able to chart a path forward for his team to join Figma. And they're going to ship some amazing stuff for the next year or two. It's going to blow people away. I'm absolutely delighted I'm going to quickly.

Turn this into a career therapy session because you mentioned, hey, whatever you like to do, monetize it. And then you said for you it was like you're a talent spotter. Like from early Dropbox days to now, just spotting talent early on, looking at this portfolio saying like, okay, this could be interesting. Like I can relate to that because what I am at a deep down level, what I like doing, I don't care if I make money on it, Solio, but I just love connecting people. If someone is snorting cocaine, they get a high. I get a similar high from just connecting people or helping out in some ways. If you're like, hey, I'm trying to do this or this is what I'm working on and I'm like, oh, I met somebody else who can help you and I just love doing it. I don't care necessarily about monetization about it. And that's the reason, like the whole premise of the podcast, like yeah, like the name and stuff, the SEO has played in my favor and yeah, it's getting the downloads. But what drives me every day is damn, like I got to meet with Soleil and there's some conversation that mental model could be changed. We built a relationship. I don't know where it's going to go, but I rather build that relationship now rather than years later where I might need some advice from you. And yeah, I'm a designer right now. I've got some couple of other side hustles. I teach design as well and I don't know where it's going to go, but I don't even know what I'm trying to ask you. I guess maybe I'm trying to find solace in the fact that you stuck to what you like doing and eventually found a way to commercialize it or monetize it. Spotting talent in a way by becoming an investor. I don't know what that route is for me, but I'm done with the rant. Any thoughts or comments on that?

One thing is keep an open mind to how the people you work closest with perceive you. What do they say they appreciate most about you? What do they value in their day to day interactions and where they feel like you're well suited to Excel because I think that sometimes it's easy to allow our own narratives to reinforce a view or self concept that could be a little bit divergent or incomplete from what other people say about you. One of the things that I have learned the hard way that Combine taught me is there's something about software that scales so beautifully and because it scales so beautifully, it can impact so many people. People way outside of like your mental sphere while you're asleep. I think that to create something really useful and desirable in the world often has that property of scalability and reaching the most folks and creating opportunity far outside of anything you can see. Right. And so whether it's content like this or other podcasts that you do, whether it's finding ways to productize the connections of folks or enabling a thousand Js to take that dopamine hit of making connections, I always try to urge folks to look at it through the lens of not just what you can do with your time on this planet, but what software can do to magnify that feeling for other people. The closest thing that I have seen of late that really encapsulates this, ironically, it's a Roblox. They created this environment in which people can inhabit it, but then create environments that they in turn can popularize to other people. It's like they didn't just create a world, they created a mechanism for world creation. And there's something just gorgeously scalable about that. That is the lesson of our age. That should be the thing we celebrate, not Minecraft, because that open ended making things for other people, that will be the skill set that is most evergreen and the strange new world that we're going to wake up in five to ten years from now. And, and I think that in combination with like a fervor for helping folks will go a long way.

That's very assuring to hear because when I look at what makes me knowledgeable. Right. There's some things like when I look at your career path, you built all these amazing relationships by being in the right place at the right time, helping out people. And to me that's what makes Soleil non fungible. Even if somebody were to copy your model, do the same thing you're doing, you've put in the time over the years building all those relationships, the track record, I feel like to me this is play, this is fun. Connecting with people, helping them out is fun for me. So I know that is what makes me non fungible. Yeah. There could be other things as well I might figure out along the way.

Well, my hope is that if I can inspire a hundred people to do this line of work better than I did, the world's a much brighter, more prosperous place. And I don't. Yeah, I'd rather wake up to that world than opportunities being concentrated around individuals, more open Some than anything else because it's. That'll be the world that my kids grew up in and that I'll age into. What's. What has you excited right now? When you look across the landscape of everything that's going on in AI and design coming out of the Figma conference and what are you right now like excited about in July 2023 that you can look back on in two years.

To be like just the trends that I see or something that I am.

Working with someone on it be honest, not clever.

What gets me excited is like what Figma has done for design. I'm trying to figure out like what is that for research? Because when you think about user research, there's. You have legacy tools that are doing it a certain way and working in a large organization. What I've seen is you have the researchers that take care of and designers and I'm talking about maybe not as forward design thinking companies like Facebook, but I'm thinking about a lot of other like fortune finder companies where the researchers are doing their thing is very siloed and the designers don't necessarily know the tool. It's not intuitive to use. So I'm like, who can then merge that thing and then become that tool that's like as easy to navigate in team multiplayer like Figma. And the team that I'm most stoked about in this space that I'm working behind the scenes to helping them out in any way I can is Ballpark. Ironically, the founder Murat Mutlu started Marvel App, also based in London. I'm not trained as you in thinking about the total addressable market and all these things, but I think my interaction with him about how he thinks about the future, about getting the reps in for example, because Marvel they already had to build a lot of infrastructure which gives them a head start now that they're in the research space with Ballpark because they can leverage a lot of that and then speaking to the team and knowing get to know them. I also observed a lot of things like wow, they are resilient people. Like they are really talking to customers. So one of the big career mistakes was that I tried really hard to break into Envision. I don't know, like got maybe like 8 to 10 reviews, came close, but no cigar. Yeah, like, like really I pulled that all. Like I had even the execs there try to recommend me. And what I learned from that whole thing was Envision was really good at marketing and stuff. When I look at Figma, they were very product development focused. They were obsessed, less about hype, but they were more about let's ship things consistently and quickly what our users want. And so with this Ballpark team, I'm like, oh, my God, I'm seeing a pattern there. So not sure what's going to happen. But that is the thing that it's got me really, really excited about.

Yeah. If you're the best product in a category, you can go much further. Everything else can follow suit. It's like just. Yeah, it's. I think ChatGPT is a funny case study in this regard where. Who would have thought a year ago that ChatGPT would be the biggest consumer brand on the Internet?

Right.

Just sheer utility and being the best product can go a really long way. You'll have to introduce me to this team. I'm really curious to learn more about what they're working on.

Yeah. Thank you so much for coming on the show and sharing your wisdom.

Thank you for having me, man.