Soleio - The rise of designers who ship

You want to be a designer who ships. If you're not shipping, you're probably not going to succeed in a startup environment. Startups are so hard, the vast majority of them fail. So right out of the gate, your odds are stacked against you. At a successful startup, you're going to be shipping and experimenting and throwing away a lot of work. That's a muscle you just need to exercise now. It's like making sandcastles. It's going to get washed away pretty fast, even the really great ones. That's just the nature of the work and you have to openly embrace that, not be sentimental about any one particular day.

Welcome to Dive Club. My name is Rid, and this is where designers never stop learning. Now, as soon as I finished our original interview, I knew that I had to have Soleo on as the first repeat guest. If you missed that episode or you're not familiar, Soleo was one of the very first designers at Facebook and then went on to lead early design efforts at Dropbox after that. Nowadays he's a full time investor where he's backed some really amazing companies like Figma, Vercel, Framer, and a bunch of other startups that you've definitely heard of. So a big part of this conversation is tapping into Soleo's perspective as an investor, what he's seeing in the landscape today, and even getting a little bit of the backstory for what it's like to invest in a company like Perplexity. But we're also going to talk about some of the traits that make for a successful founding designer and look at some really interesting potential future scenarios. But before we get into all of that, I asked Soleo to go deep into what it looks like to be a designer who ships.

I think that coding was always a little bit of a red herring. And I like this newer framework of designers who can ship because at the end of the day, you can segment designers into these two buckets. There are people who have experienced getting work out there in the world and bending in the wind of reality and being accountable for said work and feeling the reward of shipping of getting something out there. And then there's everyone else. Everyone else who sort of sits in the safety of producing a blueprint, producing a facsimile of a thing, making concept cars rather than shipping product. Why it feels relevant to the here now is that today's tooling no longer requires you to be a coder. In the past, it used to be a holy war over whether or not designers should spend time and energy learning how to Code. And thanks to tools like cursor, like ChatGPT and Claude, that requirement is now long gone. Designers who are not shipping are running out of excuses. And I think as an industry, we need to fully embrace the responsibility that I think designers have to getting their work out there and getting their work in front of people and learning through an applied practice rather than through ideation and generating concept cars and blueprints and things that will later go into production and not being kind of accountable for reaching an end user and talking to an end user and seeing how that end user actually responds to the work that we produce. I think that the here and now is going to be owned by designers who ship, by people who are willing to put their work out there early and often and iterating effectively in public, because I think that they're the ones who are going to ultimately learn faster than everyone else and arrive at the insights that drive breakout businesses. There's that old saying from Facebook, the quick shall inherit the earth. I firmly believe that there's nobody faster than the designer who's shipping product and and getting their ideas in front of users in the most tangible and realistic way possible. Today's tooling is exciting because now it takes away the requirement of having a technical co founder or an engineering partner to getting an actual thing out in production.

All right, there's a new product that I absolutely love. It's like Midjourney meets Figma and it's called Visual Electric. It's a new image generation tool that's built specifically for designers. It's the most photorealistic one out there. Even more than Midjourney, they also have a bunch of beautiful, beautiful, predefined styles. And it's so incredibly easy to iterate because the entire experience happens on an infinite canvas, so you'll feel right at home. Honestly, the whole product is the epitome of taste. So the next time that you need imagery for a project, I cannot recommend Visual Electric enough. Head to Dive Club Electric to check it out today. And if you like it as much as I know that you will, you can use the code Dive Club to get your free first month for free. I'm noticing a trend. The designers standing out on social media today are the ones that are using video to showcase their work. That little extra bit of motion is the easiest way to make your designs feel premium. And that's why I'm such a big fan of Jitter. It's like Figma, but for motion design, so you don't have to wrestle after effects to make a killer highlight reel anymore. Jitter makes it way easier. You can import your designs with their Figma plugin and they have beautiful templates to help you get started. If you want to give it a try. Head to Dive Club slash Jitter. That's J I T T E R. Okay, now on to the episode, even as you're talking. A couple of days ago, I was chatting with Meng2, who has put together this incredible video editing product. He did it in three months and it's like 50,000 lines of code. And he made the thing with cloud artifacts and cursor, and he just made it. He solved his own problem. It was 100% his own problem. He had this software stack that he's using five different tools and it's not quite working. He's like, you know what? What if I just freaking made the thing? And now it's out in the world and it's like a cool little prototype of what it could look like to be a designer who is empowered to just make the thing.

Exactly. And I think what it ends up doing for designers who have that bias for shipping is that it gives them the ability to bring forward a vision not in the safe format of marketing collateral or visuals on tilted devices, but something that people can actually use and respond to and formulate a practical view on and even pay money for. I think that that changes the hiring dynamic for how this designer finds colleagues to work with. I think it changes the power dynamic in terms of them feeling responsible for serving customers rather than serving an idea. And I think that what we've seen thus far is going to end up being the tip of the iceberg. We're going to find that there are people in the here now who have sort of classically been designers that produce amazing products with the help of engineers, are probably going to be able to produce amazing products without having to spin up an engineering colleague just to at least get that initial V1 intact and in place and in front of actual users and customers. I think that that power dynamic is really significant. And it's only going to be available to people who are willing to actually get their ideas out there, who are willing to ship. I worry about the designer who instead focuses on craft that sits on their computer, because that's going to be lost to. To folks who are willing to actually, like, cultivate ideas and get them in front of users. For every Brian Levin and Meng to that exists today, we're going to see dozens more in the coming year or two. And I just can't wait to see the kinds of projects that get out there.

Okay, so then, if this is the tip of the iceberg, how does this new shift impact the way that you're approaching the space as an investor?

Yeah, that's a great question. I think the theme for me, even in the run up to the election is there's a pervasive sense of a jump ball. The future is wildly uncertain and it's available to whoever has that slight edge over the market, over competitors. It's up for grabs. And from an investment standpoint, the thing that I'm most intrigued by are looking at things that we've sort of treated as just load bearing aspects of productivity and day to day work. Things like email, the web browser, the laptop, all these things are up for grabs right now. We may not be using web browsers to do work in the near future. We may not be using smartphones to gather information about the world around us in real time or to communicate. And so this lends itself to an environment where I think that the value creation is largely going to reside in who defines the end user experience in the form factors and ergonomics there, and how everything else kind of then has to sort of sit within that solution space. And that solution space may be defined by the metas, Googles and apples of the world, or they may very well be defined by startups, people no larger than teams of 12. I love that there is such an open ended dynamic to that. It does cause a lot of consternation for me though, because you then have to formulate a view on, well, I may not know which teams will win this opportunity space, but I have to start to take active stances on things where I don't believe value will accrue over time, but instead will have to sort of justify its own existence in a new future paradigm. And what are the parts that used to feel really permanent and durable that may suddenly overnight no longer have the same degree of durability? That is not an easy job. But I am looking at the emerging space of tooling and the emerging space of form factors, devices and end user experiences that could be highly disruptive to today's workflows of checking email, responding to things mainly moving information back and forth, and having a lot of productivity gated on my participation, my direct participation in it versus a different world where I interact primarily with a core set of agents that are extraordinarily good and at doing what I used to do, but potentially at scale and while I sleep.

Okay, so this is reminding me of a dm that you sent me a few days ago that I'm just going to read so everyone has the context. Pretty interesting.

Make sure you share the screenshots.

You said usually a startup is dead if it can't move faster than the world changes. But today the world is changing faster than almost any group of people can grapple with. So how does that velocity impact the way that you look for opportunities as an investor? Especially when a lot of these world changing realizations might happen on like the other side of an order of magnitude jump in the underlying technology?

Yeah, that's a great question. I think part of it from an evaluation standpoint is applying a bit more diligence on rate of iteration and speed. One of the things that I felt really confident about partnering with companies like Perplexity early on is their ship rate was so fast. And it's one of those things that now feels like the reason why they're doing such tremendous job in market today is that they feel like they're shipping at a rate that's much, much faster than companies 10, 100 times bigger than they are. And that's a cultural bias that you cannot fake or manufacture. It's a day by day thing. But I think the other piece is there has to be a set of beliefs about where the world will end up that introduces a tremendous amount of strategic risk. But if there is no kind of acknowledgment of that future or no viewpoint, it seems to be solving for the here and now. I worry that companies will end up in the right spot because they'll be serving a market that could potentially just evaporate before their eyes. That's where I think that I've often put a lot of focus on competitive strategy and on thinking through where you want to end up over the long term, even in the earliest conversations when talking to entrepreneurs. Because if you're just guessing at it, if you're focused on the here and now, I don't know if that's going to give you real deep insight into the future or give you the right framework for making long term technological investments that could pay dividends down the road. And so that to me is like a prerequisite for founding and it's a prerequisite for at least my eager participation in working with the company. There has to be a viewpoint on where there might be a defensible territory down the road in a very amorphous landscape.

You use the word defensibility, which is actually a very specific thing that I wanted to talk a little bit about. Because I think if you kind of throw things on this high level traditional economics chart, it's pretty easy to see the cost of software approaching zero in the long run. So how does that impact the way that you think about the defensibility of a startup and where potential moats might even exist, you know, three plus years from now?

That's a great question. I think that one of the things that has shown tremendous durability is the power of brands. If you sort of step away from software for a minute, brands, you know, can, can pervade all kinds of endpoints. It can, you know, it's easy for you, for example, to picture what a Starbucks looks like inside of a Safeway or inside of an airport or on your phone. That's a power brand. If I were to suggest to you that Starbucks was working on a hotel like a, like entry level hotel for business travelers, the picture that just appeared in your mind is a byproduct of their brand. And it's probably a very vivid picture.

Totally.

And I think to people listening to this conversation, they'll probably also have a very vivid picture. That's the power of brand. It's a set of expectations, visuals, just the like the way in which people interact with an entity over time and across all these different surfaces. I believe that in the future the power of brand will be all the more important, especially if there's continuity and especially if you are using next generation tools to manage the kernel that is the brand and how the brand presents itself across all these different mediums. Because if the brand imbues trust and if the brand imbues a set of expectations around how one can interact with the brand and the world at large, I think that that can become a very deep moat for the form factors that are trivial to copy. Anybody can make coffee, right? It's not hard to make coffee. But the reason why Starbucks is Starbucks is in large part because of their distribution, because of their reach and their progressive stance towards technology, and because of a very singular brand that they have been building token by token, brick by brick. So what does this mean for software startups? I think that if you were just to boil down the decision to use product A versus product balance based on ergonomics alone, then yeah, maybe that's going to become a place that becomes quickly commoditized, that if company A releases a new feature and company B can just copy it one quarter, one month, one week later, then there's not much of a moat that emerges there. But what does emerge is how people interact with other people, other people who relate to said brand. And also how people essentially assign expectations to a brand when said new feature comes out. Do they expect the feature to work in a certain way? Right. Do they expect a level of quality or relevance that they may not expect from other brands? And so I think that that's, that's an important part of how technologists need to think about not merely the feature set that they need to be rolling out to end customers and users, but I think over time we're going to see that the competitive advantages that emerge that are really durable are the expectations that are aligned to a company's brand and this more visceral quality that extends from that creative kernel that I described earlier.

Okay. I want to keep pushing on this evaluation process and how you're looking at different opportunities. So something that you were talking about is like where maybe a little bit more in the past you're able to look at traction and extrapolating how someone is performing in the current world, whereas today that traction might exist in an old world paradigm and can be completely meaningless in the long run. And it's maybe more about finding founders and companies where there's like a match on this belief about where the world is heading. First off is you think that's a pretty accurate representation of how you're looking at things a little bit.

I mean, it's a mix of criteria at the end of the day, but I have some that are pretty strict criteria for underwriting risk. That's an important concept when it comes to investing. Right. That a lot of it is pricing and underwriting risk.

Okay, so then what are some of the beliefs that you have about where the world is heading that you have so much conviction about that it actually would maybe trump some of these other factors where if there's not an alignment on that belief, you're probably going to pass.

I don't believe that we are going to be using smartphones in the way that we do now, five years from now. I just.

Five small number.

I don't believe it. I don't believe it. I could be wrong timing wise. I could be way too early. But I am convinced that in five years time, the form factor of glasses will be dramatically disruptive to smartphones just because of the simple convenience of layering information over your eyes and having it understand the world around you. It can range from something as simple as like knowing what time it is at all times without having to look at my watch, but also just the utility of being able to layer information on everything. That you're seeing and doing as it's being done and yet still being present, still being able to have a conversation, look a person in the eye and traverse the world. And so anybody who sort of doesn't think that we're going to have to be answering to an unbounded three dimensional environment as part of like how people relate to computers, I think is not setting themselves up for success. They may be able to navigate that and adapt to it. But we saw how many companies really struggled with the adaptation to mobile, some of them to their own peril. I don't think that the transition to spatial or AR will be any easier or seamless. I also just don't believe that companies that are kind of theorizing and working towards one particular vision at the onset are likely to succeed. And so if there is a bias towards just like staying in an ivory tower and kind of honing and perfecting something, I think it just, it concentrates a lot of undue risk. And that is typically an environment or a founder where I don't think there's going to be great collaborative fit. And I probably wouldn't be a great partner to them because my general bias is to push founders to pull shipping forward and to identifying where is the customer and their pain points. In this grand vision of yours, what are you unblocking so that people can do whatever it is that they're trying to do more effectively when you're talking to them, what other tools are they using adjacent to yours that may present even more novel opportunities for you? It's really hard to support companies that believe they have the solution and the answer up front. That's often like a red flag for me. It's like we already know what we're doing, we're going to do xyz, it's going to look like this. And it's like, okay, well I'm happy to accept that. Is your current mindset, however you arrive at that, if you spoke with hundreds of customers or you've been serving customers in this fashion already, if this is how you arrived at that insight, that's great. But if it's much more theoretical, I don't think I'm a great person to underwrite that risk.

Can we look at some of the investments that you have made then? Are there investments that maybe you could even just point to and talk a little bit about that you think serve as a good example for how you approach venture at a high level?

So granola could be one. I met their co founder, CEO Chris shortly after I moved to London through a mutual friend and Chris had exited another startup, Socratic, to Google. And he was winding down his time there and thinking about what he was exploring next. And what I immediately gravitated towards was his desire to want to workshop early formative ideas, his desire to generate formative ideas before raising any money. I mean, I think I met him well over a year before he ended up raising capital, if I recall correctly. And over that year and a half timespan, before I think ChatGPT had even launched, he was insisting that AI was going to become this transformative technology that would change how people essentially like, capture the structure and the core units of utility that arise from conversation.

Okay, quick note. Granola is a new type of AI note taking tool. I use it for every single one of my meetings. Honestly, I kind of hated all the AI note taking tools before Granola, but I freaking love this one. So not an ad. I just wanted you to be able to have the context and picture it while Soleil is talking. So let's jump back into the episode.

And what I loved about my interactions with Chris is that he would often have just like these simple apps that he had built on his nights and weekends. One was a voice recording app that I used extensively and where he was at least demonstrating, at least playing with how could maybe a voice recorder help people capture a lot of their problems, thoughts, challenges, et cetera. And these are prototypes that weren't like, you know, prototypey wireframe, like, let me show you, let me tap through a couple screens on my phone. These are things that I could actually use and that I did use on my own device. You know, no craft at all applies to it because that sort of defeated the point. It was more just to kind of explore the opportunity space. And so it felt like we were able to get lots of reps in collaboratively, build trust around a common vision and just sort of support them along the way. So that when it came time for him to raise his financing rounds, I felt like I could be a pound of table advocate for him. With any investors I provided introductions to, I had enough reps to get a sense of how he would approach navigating the idea maze with the team. And the timing was great. We were seeing this inflection point post GPT of like, wow, those same transcripts, the same tool, that prototype that you built earlier can be magically much more useful now in tandem with large language models. There's something here to this, and my view on it with Granola is if you look at how Business is conducted today. Most business is conducted by humans talking to each other and problem solving and not merely just like exchanging information. They're kind of co designing together, they're kind of working together on generating a solution through conversation. And in a lot of cases, people are taking meeting notes. There's a practice there. And what I loved about granola as a concept, as an area is, well, if you're the best tool for capturing the kernel of that conversation, the structure of that conversation, that's a really useful artifact not only for everybody who participated in that conversation to understand what was exchanged, but then for everybody one degree away from that conversation, people who are downstream of that conversation to then be able to essentially be able to latch onto it and participate in it and understand what are the action items that affect them. Take that one step further. Now, in an agentic world, a lot of those action items can be acted upon by virtual collaborators as much as human collaborators. Does this start to take the shape of a next generation dashboard for work to be done? When you look at projects or collaborations or a service provider and a client, that initial conversation is like the seed of a relationship, right? And those conversations create the structure of what that relationship will entail. Right. Not as like a matter of record, but as a matter of like, what are we doing next? Right. To create mutual value. And I think that's a really powerful place to own and explore the front end. And there's just great product makers, they understand the fit and finish required to bring a V1 to market that can at least capture the possibility space there. And I'm really excited to see how they evolve beyond that. And so that was an easy investment to underwrite because of the combination of craftsmanship, good taste, but more importantly that bias for prototyping and actively exploring an opportunity space and not presuming that V1, V2, V4 internally was going to be the right form factor. That to me is a pretty good case study for the way I like to practice venture.

It's cool because I actually was talking with Sam, the other co founder, a little bit before this, and I was kind of asking for his perspective on why do you think this worked with Soleo. And he specifically talked about how especially early founders or first time founders, you have this fear of I don't want to put this in front of someone like Soleo until it's ready. And he was like, no. I think actually the thing that worked is that we started early and what sold him was the speed of iteration and figuring it out. So it's cool to actually hear you validate that from the other side of the table.

Yeah, and it's true. It's one of those things where all these breakout startups will attribute their success to a degree of fearlessness of being willing to put stuff out there. And as I like to say, I've spent enough time in the kitchen to know when something's half baked and when it's still batter. I've eaten enough batter. That's probably bad for me. When you are looking for investors, you want investors that love recipes and batter and that can tell the difference. They're not going to judge you for not having even put an idea into the oven yet.

Is there another example of an investment that you could point to and we could go a little bit deeper on that maybe got you to the point where you were excited to partner with them not necessarily because of the like speed of shipping, but maybe even just about the initial high level concept or belief about where the future was going or you know, some kind of a. More of like a pitch that was compelling about some kind of like an insight that they figured out about the world.

Perplexity comes to mind, right? Because on paper you wouldn't look at a startup that was gunning for Google and think, oh, this is going to go great.

Genius.

As far as incumbents are concerned, as formidable as they come. But what struck me about perplexity, and it was reminiscent of early figma, is that the rationale, the back of the envelope diagram of why this could work was like, yeah, if I just assume these things to be true, this could be hyper competitive. And so they kind of boil down to the following. The first is the timing of LLMs. Right? LLMs are a new foundational technology. They are expensive and slow today, they will be cheaper and faster tomorrow and there will be multiple providers, all kind of driving down the cost of the Model 2. They don't reflect the here and now. What happened today, five minutes ago, a second ago. The incumbents today are now very mature. We've been living with the 10 blue links for a long time. In practice, we've become really acclimated to having to click through to find the answer. And so that hidden extra step has been just staring us in the face for a long time. It's like an extra door in the hallway that we just sort of forgot is there because we've gotten so used to it. Remove the door and all of a sudden you're like, oh yeah, why wasn't it always like this? And the fundamental reason is because it's at odds with the entire business model. That's the crux of why this is such a lucrative business. And so if you attack an incumbent along a vector that's really uncomfortable, it sort of challenges the core business model or assumption set or philosophy of the business. And you're right, it's really hard for the incumbent to fight back because they're not just fighting you, they're fighting themselves. They're eating their own leg. And I remember this as a Facebook designer, when Snap launched. The starkest contrast between Snap and Facebook at that time was that in the same year that Facebook was rolling out Timeline, which is this page that showed your entire life, everything that's happened in your life, all on one endlessly scrolling page, all the things that you did socially, Snap was attacking us along a different vector and saying, no, that's not what people want. People want things to disappear. They don't want a permanent record of who they were. They want to engage with their friends in a manner that doesn't lead such a heavy footprint. They don't want the Internet to be written in ink. And that is a really hard thing to fight back against because it works against the inertia of the company and the philosophy and how they sort of view what people want. And you see Snaps early numbers, you're like, oh my gosh, these guys are going to be a vicious competitor. This is a tough one. This is very much like apples versus oranges. And so what Perplexity purported to do was, okay, we're going to have a system that aggregates real time knowledge stuff in reality with the foundations of a large language model to generate answers. Because we as humans are curious beings. It's why we use search, why Google was such a massive business, why it was so useful. And there's more that people can know about the world. Much more succinctly if we remove this extra step of having to click through a link, it takes full advantage of all the things that LLMs are able to offer. And we'll give people citations. It'll almost be like a just in time Wikipedia. And again, they were pivoting away from a data analytics product into this consumer first product. But it was such a simple, coherent strategy. It's like, okay, there's a bunch of execution risk, a bunch of ways in which this can go wrong, but if we hold these things to be true, they can be an extremely competitive. This is the most interesting, apart from ChatGPT, the most interesting consumer first product that I've come across I get on the, on the, on the horn with their CEO Arvind, and that conversation was not great. It was one of the most combative conversations I've ever been. I'm like, we haven't even met and we're like arguing. And there was a part of me that was like, I'm probably not going to be a great fit for this company. I don't even know if that's, this guy even likes me. But what I appreciate about it is like, I had to stand my ground and I had to be able to express my opinions about how design might work within this organization, how I can potentially support their founding designer, Henry Modisette, what it would take to win. And I found that that ended up being productive for me as an investor because I think it, I hopefully believe it increased Arvind's respect for me as an investor that I was willing to say, like, I don't think you're right about this and here's why and you can do with it what you want. But I think his argumentative approach showed a willingness to kind of engage reality and ideas. And again, I didn't feel as though I was making a mistake. I was concerned about whether or not we would be a good fit from a partnership standpoint. But I appreciated his willingness to want, to just push back, to understand, be skeptical, to challenge. And I think that that sort of bullishness is a quality that you'll see in a lot of really successful entrepreneurs. And so it's no surprise to me that that bullishness kind of cascades out into the product's pace and their innovation and their willingness to take calculated risks and be extremely bold as they roll out feature after feature and touch and influence more and more businesses and parts of the sector.

Are there other qualities that you find yourself kind of hunting for in founders, especially first time founders, where you can't put as much weight on a past success? What are some of the ways that you're kind of hunting for someone who you think has like a lot of potential and really could succeed? Especially when we live in an era where it's almost impossible to just chart the path for success and follow it.

I think that there's equal parts ambition and bullishness and stubbornness, kind of like a restless, impatient nature. And not where they stew, but they act right in combination with a high degree of adaptability of being able to listen and learn in real time and to grow and evolve with the company and with the landscape. I think that those are things that people will Exhibit in different forms before that founding moment. And I think those are basic ingredients for being a successful entrepreneur over the long term. There are different qualities and can kind of get you by in the first few years, but I think that that has consistently been my perspective on founders is there's a certain degree of like, bending the world to them, right? Reframing everything to them and what they think should be true, but adapting to new information, whether it's customer feedback, a change in the landscape, recognizing that a strategy is not playing out the way that it should, or maybe that it's the wrong strategy and a willingness to not just die on the hill, but just change hills. There is like a never say die quality to great founders that's really consistent because ironically, the more success for the company, the harder and deeper the psychological hits. You're not just shouldering your own success and expectations the world have on you. You're shouldering the success and the financial health of dozens, hundreds, thousands of people. Heavy is the crown. And I think that a lot of people don't recognize how hard it is to rise to that challenge when you may not. The evidence in front of you may say that it's not going to work out and yet you still have to do it. You still have to kind of find the mustard to push through it. I admire entrepreneurs and I look for entrepreneurs that show that degree of grit and almost like a fight to them.

What about that first designer role you mentioned, Henry? We had him on the show a few episodes ago. It was awesome to hear him talk about his experience. I think in many ways that's one of the most exciting roles in all of tech, and you're often helping portfolio companies find that first design hire. So can you talk a little bit about like, yeah, maybe what you're looking for, but also like, what does it look like to really succeed in that role? And how can designers position themselves as like an excellent partner for that founder who is wearing the heavy crown?

This is a very, very loose and fast framework, but you can sort of take the life phase of a startup. There's all the work that goes into pre product market fit and then everything that follows market fit, Right. How do you create something that a lot of people want now, and how do you then scale that offering, stave off the competitors and build an enduring business? The founding designer needs to know where they are on that continuum when they join. And anybody who aspires to be a founding designer needs to recognize that the skill sets of achieving product market fit is very different from Scaling and defending, right. What entrepreneurs ought to look for are designers who are prolific that just are very generative, that don't fall in love with their work because they're producing so much of it. They can't pick a favorite child because they have so many. And I think that bias towards being prolific lends itself to being highly experimental, having a lot more fodder to kind of plagiarize from. You'll kind of make a thing work on something and it's like, this doesn't quite work here, but now it exists, it's on the shelf of my mind and I might be able to plagiarize it later. But then there has to be a willingness in that pre product market fit era to just be throwing away ideas, to stand something up, spend a lot of time working on it, and then walk away from it because it's just a dead end. And I think that is maybe the hardest thing to tune in for because I think a lot of folks who buy the startup dream and want to work at startups want to get that first song to be a hit. And they sometimes will just marry themselves to that first song, that first script, that first crystallized product idea. Not recognizing that it may be a blind alley, it may be a short hill, it may work really well in the first few months. Maybe I have to just abandon it entirely. And there is a set of people who just don't deal well with that ambiguity. The good news is that if you're really experimental, if you listen to the right customers and listen to their pain points and you produce things that can kind of address those pain points and actually ship those things, then you are far more likely to strike a vein or arrive at an insight that can result in a breakout product. When you hit product market fit, it's never really a question. It is like hitting a vein. There's a terrific book by Mike Maples Jr. Called pattern breakers that if I can airdrop it into the desks of every aspiring entrepreneur or designer who fancies starting company one day, it would be that book. Because unlike a lot of other startup books that I've read, it's probably the one that provides what I think will be a very durable framework for understanding what it takes to achieve product market fit and the mindset required. And that so much of arriving at an insight is having that mental flexibility to recognize. Oh, I came into this selling Happy Meals, but when I started listening really closely, people just really wanted the toy. And it turns out toys are a much bigger business than burgers. And I had to kind of be able to walk away from the kitchen and become a toy maker. Even though that's not what I set out to do. I think that there's a certain degree of mental openness to not just focusing on the solution that you're bringing to the forefront, but to the broader problem space that's sort of sitting right on the periphery. And Mike Maples Jr. Provides a ton of great anecdotes there, where it's through a mix of paying attention and luck and also fortitude that people realize this is the thing that we need to do. And now we have to kind of bulldoze our way into this opportunity space. And the way that he describes it is that there's always an element of surprise that you bring a solution to a customer or to a user and the response isn't like, oh, this is cool. It's like surprise. Like, oh my gosh, this is like a magic trick. It's amazing, right? Granola had that quality when they shipped and when a lot of people use it for the first time, where it's like, oh, wow, this is surprisingly great. ChatGPT certainly had that effect and I love that framing because I think that that's the bar for relevance and that's where product market fit lies. Not with the, like, more generic solutions that I think startups can sometimes fall prey to. Where it's like it's. You end up making something. Yeah, it's like, I made you some pretzels. You ate them. They were fine. They. They filled your tummy, but it wasn't like it didn't sort of punch through the noise and introduce something fundamentally new to the world. The thing that a designer who wants to found or wants to join a startup has to be thinking about is what can I do to get stuff out into the world as the status quo rather than like the nights and weekends? How can I be shipping and moving business that I work with today, now as quickly as possible, or can I work with startups part time so that I can start to get work out there in the world today, now? Because those reps are the most valuable reps that can possibly exist in one's career path. And I think the other bit is finding your creative collaborators. I think that it's always fun to bet on founders, teams that have great chemistry, I guess the word. Because you can build up a lot of trust that can endure the hard parts when you're making things well together. That's why I want to. Creative breakups happen. They're Very like, destructive is because it was a mountain of trust that was built before the whole thing collapsed. A lot was lost. And, you know, I think what I didn't appreciate as a younger designer that I appreciate now is having worked with a wide range of people and knowing off the back of my hand, like, people who I worked extremely well with and what qualities they shared and what were sort of the dynamics there that could make for a great co founder or a great collaborator. So that when it comes time to run through the idea maze, I'm not trying to figure out how to work with someone in parallel. I already sort of have some foundation of trust at my disposal.

Yeah, it's definitely a trend that I've noticed in conversations with startups is this recognition of, like, we don't know what this is going to be yet. We are just committing to, like, pushing ahead into the future and figuring out what all this new technology means and trying to find the right lane forward. And it even kind of ties to, you know, you use the word periphery, which I thought was really interesting. And like, the McDonald's Happy Meal is still kind of like bouncing around in my brain a little bit because it's like what exists in the periphery might not even exist in this slice of time. It might be the ability to zoom out, identify the opportunity the real user need that might just be on like the other end of that next jump in the technology. And I feel like I just keep going back to that variable that feels more present than almost at any other time where, like, we all are kind of aligned on like, where this is headed, but in many ways we're not quite there yet. And so how do you do that Dance as a founder? It's kind of fun.

Yeah, I think you have to. It starts with a little bit of a viewpoint on what the future will portend. I'm going to steal it flat out from again. Pattern breakers. Mike Makbowles Jr. Talks about founders living in the future. They may or may not be right, but in many respects they're trying to pull the universe, the whole world towards that future. In the future, people will get into the cars with strangers and they'll pay those strangers to transport them from point A to point B. And so they're trying to figure out how do we, like, instantiate this and have early customers and believers on both sides of the market recognize that this is safe and viable as a form of work. I personally think we're entering a future where most of our collaboration today is with people. I wonder if it'll be a very isolating feature where most of our collaboration is disintermediated by agents, right? Going out and doing the work that we want to do. And that begs the question twofold, like, what does it mean to be more isolated in this future world? Does this mean that I can be a principal designer across multiple startups rather than one? Does it mean that I need to find community outside work even though I live in a city? And does it mean that there are fewer, narrower economic opportunities in technology or knowledge work than previously? These are important questions to be asking and to at least have a viewpoint on, because that's the future that you need to be building towards and in some respects pulling the world towards and identifying early customers who can support that worldview. So that to me is one of the things that I think is easy to overlook, is that we do have a degree of agency right through technology to put forward products that pull people towards a different way of operating in the world and in having an explanation for the second order knockoff effects. So if you're a designer that can service numerous startups at once, if you can be the de facto principal designer across like say 5, 10 startups, how does that change the nature of equity? How does that change the kinds of hiring opportunities that exist at early stage startups? Right? Am I competing with one well regarded designer who can service 10 startups at once? I mean, that seems like a bizarre way to think about it, but it's not outside the realm of possibility that tight little design agencies can unbundle a lot of these early startup roles.

We talked about tooling and it feels clear that designers who can ship not only will have a bigger impact, but like maybe will be operating at a level of scale that's almost unthinkable right now. If you play that out even more. Like, how do you think it changes the way that software teams are structured? Maybe also like how they operate and just like generally like what it looks like to create software in a commercial environment in the future. Like what are some of the ideas that you're kind of wrestling with on that topic right now?

I'm really intrigued with how systems self improve and how products self improve and what are the regimes that kind of support a training advantage or data advantage in doing so. It feels to me like we're entering a world where we're introducing like spellcheck to software and you know, software is going to be able to just say like, this is bad, here's how to fix it. And you go, yeah, that's bad fix it, fix it right, and then you'll flip a switch and maybe it'll just automatically start to fix it. But that's more like optimizing what exists. I keep wondering about, well, what do we hire software teams to do? It's usually to execute on a strategy. And so how do we formulate a strategy and then execute it? Those are two separate questions. They're related. It's not like they're compartmentalized. But I fancy the idea of if software could start to self correct, maybe it could start to suggest where to advance next. Where might there be larger opportunities to drive business metrics forward or to completely rehash onboarding engagement product architecture? And this has classically been the purview of a full time software designer or an engineer or a team of software makers. But if the way in which that team would kind of go to execs or to management and say here's what we think we should do next, we're going to have a product review and discuss it. If a computer can just do that in real time, drop an email into that executive's inbox or management's inbox and then start to build that and experiment with it and release it to production and provide evidence to support said strategy. That's a very different model for how software is made. It takes a lot of the guesswork out. It may make things really homogenous, but maybe that's fine. Maybe it'll end up streamlining how much time it takes to ship new products and new business arms. That makes every player today that much more competitive, right? It creates a much more hyper competitive environment and ideally one where like the cost of things gets further and further driven down. I think that humans will always be there to rubber stamp strategy, right? Or act as like the de facto copy editor or you know, chief editor of the work that humans and machines will produce. But we've largely relied on the judgment of people absent the kind of wisdom or evidence that can be absorbed by systems that can push software out to production in limited types, tightly scoped manners to gain insights and to build evidence for larger sweeping changes. And I find that really interesting. I think that changes how startups can compete with incumbents that have established distribution. But it also changes how we think about the composition of an early team. And will founders be managing people at the onset or are they going to be managing a suite of machines and a much tighter payroll of personnel? Will founders ever need to hire employees in five to six years time? And will the unbundling of startups just result in a lot more startups that are much smaller but that can create massive amounts of enterprise value without having to generate teams of dozens. And I think what we've seen generation over generation is that this is in fact the case that companies, technology companies become more atomized and the composition of each molecule has different components. You might be able to hybridize roles that were sort of ironclad, pre GPT marketing, design, engineering, product. Right. I think those things might get blurred altogether and you might be able to wear all four hats in one employee.

That idea of like self optimization is very interesting. It makes sense though. I mean it feels like in that world I think I'm pretty grateful to have the core skill of design, but.

You also have the core skill of asking great questions, building a brand, marketing a product that you've made. I think these things all work in one's favor. And maybe the future is one where we start to build software more and more for the solo entrepreneur where it's like, here's you can get really, really far without hiring your first person because we've essentially created verticalized software across every single function that you'd historically hire for. That's a weird and bizarre world.

But it's weird and bizarre.

We're vastly, you know, I mean today like we think that the Internet software is static graphics and drop down menus and transitions. Maybe it's all video in the future, maybe it's just conversations with people, much like this conversation here. Now, that world is not far away. These real time avatar systems are uncanny in terms of how accurately they look and in some respects, if it's a form factor of how humans relate to one another. If I can talk to somebody who looks and behaves like a human and who's building software in parallel, maybe it can then give me the opportunity to focus on what I'm uniquely good at. And I do wonder what that world looks like from a brand standpoint. Like will brands really start to concentrate around individuals and people who are recognizable? Where will people assign value and trust to? What are the entities? What are their form? Will they be in fact the Starbucks, the Nikes, the Apples of the world? Will they be the personalities, the people, whether real or manufactured? I'm not sure. But I do think that a lot of the hidden costs of making software, making decisions are being radically exposed right now and realizing that, yeah, there's much shorter paths to water.

Hey, it's Rid. I'm constantly asked about my favorite products, so I'm gonna take just one minute and give you a quick rundown of my stack. Desen is how I ship design changes without having to code. Framer is how I build my websites. Genway is how I do research. Jitter is how I animate my designs and Play is how I design and prototype mobile apps. Visual Electric is how I generate all of my imagery and Raycast is my shortcut every step of the way. Now I've hand selected these companies to partner with me so that I can do these images episodes full time. So the best way by far to support the show is to check them out. You can find the full list at Dive Club slash partners. Okay, now on to the rest of the episode. Before I let you go, I want to kind of wrap this in a little practical, you know, fortune cookie for those that made it to the end, you know, because I think we can keep going and imagining and dreaming about what this future world can look like for a very long time. I want to speak to someone like very specific specific who's listening. It's this person who maybe they actually are already at a startup, but they believe in some of these core ideas that you're talking about. We're like, hey, the world's going to change. AI is real, it's a big deal. The way we think about enterprise opportunities is about to change and I don't know what it is yet, but I know that I want to start something, I know I want to put something out into the world and I believe in my long term career as, you know, one who is a founder and starts new projects. So what is an investment that that person can make into their future founder journey today?

That person should work closely with the startup at its infancy. They should work with a founder who respects what they're great at, who has a view on what they might be able to grow into and that is aligned with what they want to grow into. Reading about startups, hanging out with startups, those things are not the same as working at a startup and working with the founder and formulating a view directly. You and I could not hang out at a skate park long enough to just suddenly get on a board and learn how to skate. At some point you got to get on it, right? And the longer you delay that, the more you're pushing that knowledge out into the future. That said, you want to be prepared for that, that transition. The way to prepare is to understand that startups live and die according to how quickly they can iterate and ship products. You want to be a designer who ships. If you're not shipping, you're probably not going to succeed in a startup environment. It'll be a really hard transition to make and it'll be really hard to find a role where you'll be set up for any measure of success. Startups are so hard, the vast majority of them fail. So right out of the gate, your odds are stacked against you. You're not servicing yourself by joining a startup that fails and that doesn't have you work in the way that you would work at a successful startup. At a successful startup, you're going to be shipping and experimenting and throwing away a lot of work. A lot of work. And that's a muscle you just need to exercise. Now that you're in the business of software, it's like making sandcastles. It's going to get washed away pretty fast, even the really great ones. That's fine. That's just the nature of the work and you have to openly embrace that, not be sentimental about any one particular day. And then lastly, I've always believed this is a personal philosophy. It's easy to be the best at something if you're amongst the first look to what's emerging where there are few players. What's amazing about joining a movement early on or having a view on what's new, is that it's easy to meet everybody who is good in that new space. In the next year, there's going to be a set of founders who try on the Orion headsets over at Meta and they'll think, yep, this is the way the world's going to go. No question about it. I don't know how many years it's going to take, but this is the way it's going to go. That's a finite number of people. And some of those people are going to dedicate years of their lives to exploring that opportunity space. And I think sometimes tremendous success can arise from joining these things that are new. Because nobody has a head start. No one. That's the thing I always love about software design. For me, one of the most formative experiences of my life was working at a communications office in high school, and I had one boss. We were a team of two. He was a poet turned desktop publisher, and he taught me how to use QuarkXPress, how to use it properly. The pivotal moment for me personally was when he pointed out that the team at Time magazine, a magazine I subscribed to, uses the same tool that I was using. And they had probably been using it for just a couple years too. And that really landed in A profound way. He was like, nobody has a head start on this. No one. They might have a lot of, like, prior knowledge that they're going to shoehorn into this new medium, but they don't really have a head start on you. The tools have largely, like, solved a lot of these things for them, and I've carried that insight with me my entire career. So look for what's new and emerging because nobody will have a head start and you can be amongst the few that write the playbook.

I think that's just about as inspiring of an ending note that I could possibly concoct. So that was awesome. Thank you, Celia, for taking the time.

You are also. You're one of the first. You may not realize the degree to which you can meaningfully move the state of design forward by talking to folks like Henry who are at the bleeding edge, giving them voice and making the work that they do that much more tangible. Because I don't know about you, but growing up, you'd see amazing stuff exists and they were made by people God knows where, and you don't know how they even got their first step. I remember finding a book on how video games are made at the library, and I think I read that book 50 times because it was like, oh, my gosh, so this is where they live and these are their names, that these are people that exist in the world today. And I wish there's a way to reach out to them and hear what they think and how do they get to do what they do. I want to make video games. And hopefully for folks that grew up using software, they'll be able to at least assign a face to the work and then more importantly, assign what does the job actually entail so that at least I'd know I'm at least in the right zip code when it comes to how I spend my time. Yeah, it probably won't be spending time in figma. It'll probably be time spent dabbling with these new emerging tools that can generate FIGMA files and then finding higher leverage ways to hone those artifacts and work with AI more effectively than any of the classical designers.

Man, I feel like we could start a whole episode from this point because it's like, I totally agree. And it just feels like there's never been a better time to have a podcast because it's so easy to be curious because everything's new and everyone's figuring these things out for the very first time and you have whole new industries that are just like, sparking up. I think I'M going to save that for the third episode. We'll just commit now to like, you know, we'll bring you back on for the third episode. And by the time we talk again, I'm sure that the whole world is going to change yet again.

Speaking to this reality on, like, what changes in the near term? Because it.

Yeah, it'll be pretty fun.

Thank you for, as always, the opportunity. Man, I really enjoyed chatting on hey, it's Rid.

Don't forget if you want to go even deeper. Each week I send an email out to over 10,000 designers with bonus resources and key takeaways from these conversations. So head to Dive Club email to sign up. Okay, I'll see you next week.