Ron Goldin - Building your ideas as a design leader

[00:00] This is literally like right after this meeting where I was told by like VP pluses on the design side, this can't be done. I was like, Hey, check it out. Like I'm a non-engineer, but I just built the ability to create an SVG that can be colored to any color you want to, can be transparent, can have all these brand colors. And a merchant never will have to lift a finger. And we can have a new online checkout. That's like, you just present to the merchant and be like, do you like this?

If not, here's some other colors you can tweak. So like, that's again, that world of like, [00:30] designers are literally have this superpower. Welcome to Dive Club. My name is Ryd and this is where designers never stop learning. This week's episode is with Ron Golden, who's led design at Google, Shopify, Uber Eats. And in my opinion, he's one of the perfect examples of what it looks like to thrive as a design leader in this new AI world. So we're going to do a deep dive [01:00] built a new product called Matchmaker from scratch.

But before we get into all of that, I asked Ron to share a story of what it was like as an early designer working on Uber Eats. I remember like my first week on the job living in New York City. I had never done a delivery before in my life. I wanted to dock the product and so I [01:20] downloaded the Uber driver app, and just went through the process myself. In New York City, you've got these city bikes everywhere. So you just like... [01:28] basically can check out a bike and, you know, you get 45 minutes or whatever.

And so I remember taking, uh, [01:35] a ride for myself. And I mean, first of all, you know, we're both designers. Like the empathy building was extreme. The onboarding was... [01:42] Awful. I finally ended up [01:46] getting the driver out to work. I pushed a button that says go online, and I'm just sitting there, and nothing is happening. I could not get a job for the life of me, because Uber Eats was still pretty small. And so I basically just quit. And that's kind of the beginning of, I think, [02:01] the first few months of my Uber Eats, [02:03] tenure was really more almost of a research role than a design role because Uber at the time really had this strategy of even though it was a pretty large company, Uber Rides was in hundreds of cities, it still acted very much like a startup.

So the driver app, they literally just added a couple of buttons so you can pick up a delivery, but there was nothing bespoke about it that really catered to the couriers. And so I found that to be true. And so I started doing more of these [02:32] Then I started bringing some of my colleagues along with me to do the deliveries. We ended up getting actual gigs and dropping them off to people and didn't get paid a lot, which was part of a whole other thread of conversation I had with my PMs.

But it actually turned into an international research endeavor as well. A big part of our challenge was trying to scale to non-US cities. And one way to do it, obviously, is just flip a switch. But the other one is actually see what it's like to deliver in Mexico City. [02:59] in Tokyo, in Bangkok. And these are places we actually travel to. And of course, down, like, oh my God, this is like a whole different sport when you're doing a delivery in the sort of skyscraper neighborhood of Tokyo, where there's literally like your front door to the person's...

[03:16] actual apartment is like a 15 minute journey through multiple gates of security, there's no landmarks. And so we would literally ride around these cities with translators trying to figure out which way to go, dodging traffic, almost dying, all of that stuff. One of the things I really wanted to do was figure out ways to bring that shielding of like, [03:37] the fear, the anxiety, the pain of being on these bikes and literally almost dying, to home base, so to speak. And I don't know if you remember Google Cardboard at the time.

Oh, wow, yeah. Yeah, yeah. So I had recorded all of these trips using very early technology, [03:54] generation of the Insta360 camera. I'd mount it to the bike and I'd literally record these trips to literally capture what it's like to be everything from dodging traffic to figuring out which way to go when maps is telling me the wrong directions. Even having security guards tell me, no, you can't come in. [04:12] without certain credentials to deliver food. So I was just capturing all of this stuff. And so I sent this Google Cardboard, along with these Insta360 videos that I uploaded to YouTube, to our head of Uber Everything, it was called.

So this is Uber Eats, Uber Rush, a bunch of other products. This is Jason Droege. He watched them. He literally watched the videos of me... [04:32] sitting in a car in Los Angeles outside the biggest sandwich restaurant in all of LA for three hours in a car with a driver and not getting a single gig. And this is actually, I mean, this is a perfect example of this. Like that was the one I said to him because our assumption up until this point was like service to big restaurants, right? Like they're getting all the traffic, right?

[04:51] And so I was trying to replicate that, and this guy literally was suffering in his car. He hadn't eaten. He had to go to the restroom and couldn't do anything but wait. So that was the beginning of pretty heavy product and design investigation to why is this happening? And what we realized, which now is kind of common sense, is if all of the couriers are being told to go to the hot restaurants, [05:15] then there's too many couriers. [05:16] and not enough meals, right? And in fact, we didn't really have a really good sort of like visualization at the time on the Courier app to even tell people where the opportunities were.

And so people weren't even like using the app to like understand demand. They were just literally going to Google. [05:33] maps or Yelp or whatever to find popular restaurants and they just park there. And you might even see this near in your town, like down the street from me, people like park outside of Shake Shack, just like waiting. [05:44] hoping, right? So it was the beginning of a long project that ended up with, A, a really robust way to visualize what we called hotspots. So places that aren't the tried and true places that you might imagine have a lot of demand, but places that might even be a small mom and pop Chinese restaurant [06:04] but they're like all of a sudden happens to have a little pop of demand.

Right. And so a, it was a way for people to like, start to sort of spread out their efforts across the city. The other one was just really interesting. It was like a lifestyle thing, which is like, [06:17] What people used to do, which is crazy, is this guy in A. used to drive. [06:21] one and a half hours, [06:22] to get to that sandwich shop. [06:24] that had no business because he figured in his own neighborhood in like Ventura, California, there wasn't enough demand. Well, guess what? [06:31] there was, we just didn't have the tools to say it.

So now he could stay like in his neighborhood and, [06:36] save on like an hour and a half of gas each way and actually support local businesses and like have less of a commute so to speak to get home real quick message and then we can jump back into it jitter just released animated components so you can design once reuse across your file and update every instance with a single edit i'm personally very excited about this because i use jitter for everything from animating the in-flight logo to animating the buttons in the dive newsletter [07:06] in sync and it's available today just head to

club slash jitter to get started i've anticipated dessin's recent release for a full year it's called surfaces and it enables you to design and prototype directly on top of an existing production interface all of the pages and flows that you need are pre-loaded inside of dessin as starting points so you can easily make changes [07:36] you can share your prototype in a single click. Dessin is the only design tool that allows you to design on existing pages and flows pulled directly from prod, which is a pretty big deal for teams.

And you can get started today. Just head to club slash Dessin. That's D-E-S-S-N. Now onto the episode. You can tell that you're a researcher at heart, just how quickly you're just like, I'm just going to do the whole flow end to end. But there's definitely a version of [08:06] a nice memo and you sent it off to leadership and they read it and they kind of nod along and then it gets tossed into a spreadsheet somewhere and maybe you think about it again like two, three quarters later, you know? And so the part that I think is so interesting is how [08:20] you captured all of the video.

You're like, I'm going to think very intentionally about how to transfer this empathy. And ultimately, it seems like that [08:28] played a big role in motivating people to actually take action. Jason Droege and my manager at the time, Andy Zabalski, he supported me to actually get that video in front of the entire Uber Everything organization. Jason was like, "People need to see this. Our PMs, our engineers, our ops people need to really understand firsthand what that pain is." And so what we did is we cut a version of that video down from obviously you.

[08:53] two and a half hours, till like three minutes, [08:56] But even at three minutes, we showed it in all hands. And we just left a minute. We left a minute in that presentation of just the feeling of sitting in a car. [09:05] waiting and nothing to happen. You've probably been in all hands of the company, or maybe you have it, I'm not sure, but they tend to be packed with content. The power of having hundreds of [09:16] where we're all just like sitting there, awkwardly waiting, looking at the app, [09:20] Nothing going on.

[09:21] Like it was such a powerful moment and it actually spearheaded what became, I think the kind of Uber dog fooding program. So like now at the time, like I said, it was like pretty scrappy. Like I was sort of doing this with a bunch of people. I got more engineers to do it with me and so on, but it actually became a program across all of Uber Eats where people were encouraged to basically do it. We had researchers, real researchers actually planning the operations of all of this. So it's scaled and capturing insights and all that stuff.

So like the appetite, [09:51] I think for... [09:53] especially like a human service, like Uber Eats, where there's like real human beings, like going through the motions of doing something. There's a real appetite, I think, for anyone building products to like actually put themselves in the shoes of people. And like, you know, it's so hard to do. I feel like if you don't at least have that taste of like what research feels, at least a little bit of the skill set and maybe some of the skill set, the courage [10:16] To just go out and do it yourself and know that you're going to fail and that's okay.

Listening to these stories, there's a line on your website that I saved that makes a little bit more sense now where you talk about how you like to join companies at inflection points. And there's this need to do things differently or to take a bold bet or to change the way that you operate. And so I'm curious, you've given your background, you've spent so many different companies, so many high impact roles. [10:46] people an idea of what this moment looks like in practice and then how you show up as a designer?

Sure. Yeah. Yeah. I mean, maybe I'll talk about Shopify. I was responsible for leading online checkout. And if you go to, I forget, it's like com slash checkout or something like that. They have this marketing page and big, bold, large text. It's like the highest conversion checkout in the industry. And so imagine taking a job where your job is to basically improve what is supposed to be the industry standard is already great. Okay. So that's challenge number one. And [11:16] Imagine that the CEO of Shopify, Toby Luca, is telling your entire team, [11:21] "We need to redesign Checkout and make it better."

- No pressure. - No pressure and also no direction. Like it just has to be better. Because that is like his, and I love this about him by the way. [11:31] That is his DNA. He's always looking to... [11:34] tear things down and build them up again, question things, make things better. I would say that was a surprise to me when I joined the company. I joined at, maybe by accident, the perfect center [11:45] In the time I was there, we launched [11:47] the partnership with OpenAI. So we were like one of the first companies in the world to basically like have that authentic e-commerce experience within the chat interface.

We launched cryptocurrency with Coinbase. So the first time Shopify had crypto globally and the check I redesigned. And this was like my first six months of the company. I don't think it ever shipped that much. [12:07] in such a short time. [12:09] during a wrap-up period of unemployment in my world. And honestly, I loved it. Again, I kind of brought that same energy that I had in those these days of a company that, yeah, technically is public, technically it's on the stock market, but it really operated like a scrappy startup.

This is where I would say I had worked in AI adjacent before we all talked about opening AI, ML-based product work, all that. But I think that Shopify was really my first foray [12:39] coding world. Like at the time, and again, this is like a year and a half ago, like it's not ancient history. Almost nobody at Shopify was using AI, period. Like nobody. Like I was part of a small cohort of designers that were like early testers of like Figma MCP connecting to cursor. And it was like magic for all of us.

And it was also insanely painful. Like I remember like it took me [13:01] at the time, and a bunch of people, we had Slack going, like, it would take people hours, days, to get MCP to connect, because that's where the tech was a year and a half ago. It was just clunky, and just not very, like, yeah, there's all these things you have to know, and you could just ask Claude, because it didn't have the answers to the stuff yet. So we were just figuring it out. And it was just really fun to be part of this little crew.

[13:23] of folks who are just like, before the Kool-Aid, like, what is this thing? And is it useful? Or is this just a fad? And can we use this? And is it going to be interesting? And then, you know, maybe I'll just share... [13:32] my light bulb moment with this, which was, so Shopify has this big meetup once a year. I forget technically what it's called, but essentially like a big part of it, like maybe 80% of the time is like a massive company-wide hackathon. Everybody, not just design, not just engineering, like everybody, whatever your role is.

I was in the online space. I love physical stuff. They had this like really cool, like little garage, like literally garage with like point of sale hardware, [14:02] stickers. And just like, if you want to take her, go for it. And I grabbed, you know, one of the designers that reported to me, said, hey, you want to work on this project? I have this idea for a POS [14:14] thing that could talk to an NFC sticker and in, I'm going to say eight hours, tops. [14:20] We went from [14:22] an idea to like a fully working thing.

And the thing just to kind of give you a picture is like, imagine like a sticker that has NFC chip on it and you're a merchant. And instead of having price tags, like static ones or like little signs, you basically just have these NFC stickers that you can put all over your sweaters and pants or whatever it is you sell. [14:44] And then a customer can take the shop app [14:47] and just hover, they don't even have to unlock their phones, hover near that sticker. [14:51] And you have like a little notification that's like product detected or whatever.

Tap on that. It basically says, oh, this is like a blah, blah sweater, you know, made of 90% wool, like and price and reviews, all that stuff. And you can just tap to buy. It sends the purchase over to the POS in store so that the person basically automatically paid for it, checked out, don't have to get in line. [15:15] don't have to talk to anybody. The cash register person knows you didn't steal because it's in the POS and you could just walk out the store. And so like literally we basically just built this prototype, right?

Which is like the experience I just showed, right? And the NFC connection, you know, was again, we had an, we bought an engineer for like 30 minutes to say like, can you help us with that thing that we were stuck on? Because again, probably today, [15:40] We didn't help. You got to have to earn it back then. Yeah. I say back then, it's only a year and a half ago, which is insane. You have this really storied... [15:49] career arc and yet so much has changed in such a tiny window here toward the tail end.

So maybe we could even use that as an opportunity to reflect a little bit. Like when you think about your own early philosophies around design leadership and how these Uber Eats and like even Google experiences were shaping it and then what you like think and how you operate today, I'm kind of curious, where do the biggest deltas exist? I think you're definitely seeing a lot of [16:19] Thank you. [16:20] like less layers of management. That in of itself means if you are [16:26] a manager at a company [16:28] that can mean a few things.

Like one, you probably have a lot more reports maybe than you're used to. So like we call that wingspan, right? An increased wingspan for each manager, senior manager, director, right? The other thing I think that has changed is kind of along with that, right? Like if you are, I'm seeing more of a player coach need, folks that reached out to me, folks that I coach personally who are looking for their next jobs at times. I've done a little bit [16:58] especially like pre IPO companies that are looking for this like player coach type.

[17:02] which is, you know, I mean, there's probably a lot of ways to define it, but for me, it does often look like maybe managing a smaller team. But, like, in my mind, that is like a Shopify-sized thing of, like, [17:14] two, three, five, six, something in that range. You're managing the team, but you're also with the team. Like you're building things together. You know, you're kind of not in this ivory tower, you know, [17:23] just doing performance reviews and alignment meetings while the ICs are doing the things the ICs do, like you are all, you are all part of the same team and you kind of do have this dual responsibility of like making sure the team is happy and healthy and like doing their best work.

And like for particular things that maybe are, you know, most suited to your strength, you're also like diving in. Like for me as an example, like there's a few things that I'm passionate about. And these days and like, [17:47] where I find I'm either asked to or spend my own time. One, which I talked about as like zero to one stuff. Like if I'm on a product team and everyone's thinking really incrementally, [17:56] Like, especially these days, I'm not going to, like, write a Slack or an email and say, hey, guys, I have an idea.

I'm going to go to Cloud Code. I'm going to spend 20 minutes. I'm going to bad code something that people can react to and see because every company I've ever worked, like, prototypes win arguments, right? Prototypes get people psyched. Like, you know, moving away from slide decks, moving away from PRDs, moving into, like, something that people can actually feel and react to where, like, your emotion is literally... [18:19] I want that. I want to ship that to our customers. That's the area I spend a lot of time. And so, [18:27] at my full-time job, I am trying to find ways to push on my own AI skills, finding ways to apply them to the work at hand.

For payments, for example, like I will Vibe code an idea for a new digital wallet or something like that, just to kind of show teams ways of thinking about things differently. And I think the access to these tools and the power of these tools and the speed at which [18:51] actually means that [18:53] It no longer, you know, for a manager to like make something on the side is no longer setting aside a couple of days, uh, [19:00] to like build out your components in Figma and create something in auto layout and then bring up a prototype.

Like you can do that in like one hundredth of the speed. [19:08] And so I think for [19:10] managers who are curious and crafty, they can do a lot more with their day, with the 40 hours that they have. And so I think that's also helped maybe for those managers like myself who also just don't want to sit in nine hours of meetings and just manage people. There's absolutely a place for that in the world and it's super important. But I love problem solving. I love being close to the problems and seeing the users and talking to them.

And so that's been really exciting for me to know [19:38] becoming more of a viable career path again for people that are like kind of on that fence between those two worlds i hadn't thought about it that way it's very obvious in retrospect but like [19:48] you hear the whole prototypes of the new PRDs or some version of that statement. But you're right. It's not just that. [19:54] We have the ability to [19:56] communicate more effectively, but the opportunity cost of... [20:01] expressing your idea in a greater fidelity is driven down so significantly, where maybe as a leader, you don't feel like you're being pulled from the larger needles that you're responsible for moving.

I've done prototypes in like Figma make or quad code in like 10 minutes between meetings while I'm grabbing a cup of coffee. There's an example actually, and it's on my [20:21] Shopify where, again, we were exploring this online checkout redesign. The actual design is still confidential because it's still a work in progress, but there's kind of like a tease to sort of the technology behind it. [20:32] which is like, we're trying to make a more expressive version of online checkout. And there are certain assumptions for what that would look like.

There's assumptions where that merchants would actually have to do something, [20:41] to make their checkout. [20:42] more beautiful, more branded. They might have to upload some high-fidelity SVGs of some logo or something, or customize some colors. One thing we knew from research at Shopify is that merchants, especially SMBs, smaller merchants, small-medium business merchants, either don't have the time or are not super tech-savvy. They just might not go through the motions of doing that stuff on their own. And so in 2025, '26, [21:08] the AI light bulb has to go on in those moments of like, wait, there's something that people aren't willing to do because they don't have time or know how to like, could AI do this?

And so that was kind of my pitch was like, Hey, you know, could AI basically look at an online store for, you know, [21:25] brand X and basically like pull even like a low res JPEG of a company's logo and turn it into a vector so that we can like swap out background colors. Like, could we like look at their website, CSS and pick out possible primary and secondary accent colors to use in their checkout? And my design leader at the time was like, it doesn't seem like merchants are going to do that.

I don't know if we can do that technically. And I asked, [21:50] Again, pre-2025, what would a designer do? They would ask an engineer, like, can this be done? Totally. Which, by the way, I did. I did. And engineers are like, not sure or flash don't have time to answer your question. Which I could have told you that was their answer even. So I'm like, okay, this is crazy. This is probably going to be like fruitless, but like, what the heck, right? Like, I went into Cursor at the time. [22:09] and like vibe coded and internal, uh, [22:13] tool, [22:15] to try to do what I just described, which was literally the ugliest thing ever, but it was literally just like a form where you can type in

com, right? [22:25] a brand, and it would basically just suck all of the possible colors, variants, from the site that could potentially be the brand colors, including, like, it's [22:35] intelligent enough. So it'll be like, oh, like this was used for all the buttons. This is probably a primary [22:40] color candidate. This was used in, you know, some of the other stuff. Maybe it's like a spot or secondary color. And then the logo thing, and we love this about AI, right? It's like, I don't have to look for an API.

I'm just like, here's what I want to do. I want to find the logo, um, [22:54] look in the header, look wherever we can, try to find a logo that maybe has the brand name or something, download the logo and turn it into SVG, and then it's a parade. I'm like, "Maybe this is the thing." And so I was like, "Great." Found an API that does that, that's open source, and it just sort of built the whole thing in. And then, voila. This is literally right after this meeting where I was told by VP+ on the design side, "This can't be done."

[23:16] I was like, hey, check it out. I'm a non-engineer, but I just built the ability to create – [23:21] an SVG that can be colored to any color you want to, can be transparent, can have all these brand colors. And a merchant never will have to lift a finger. And we can have a new online checkout that's like, [23:32] We could just present to the merchant and be like, do you like this? If not, here's some other colors you can tweak. So like, that's, [23:38] Again, that world of like, I don't know why I'm so excited right now.

I think designers literally have this... [23:45] super power, like unknown super powers, right? I just didn't even know that Claude would be able, or Kershaw would be able to help me there. And it did. I remember sharing this example to another design leader. And he's like, how did you know it was going to work? I'm like, I actually didn't. [24:00] I'm literally just throwing stuff into the AI... [24:03] black box. And I'll tell you, having been vibe coding now for two years, the stuff that I'm doing now was so much harder than it was a year or two ago, slash felt impossible.

And that's the other thing, too. That's such a... [24:16] fun and weird thing about this moment is like, [24:18] You can't even claim to be an expert on any of this stuff because literally like next month it's going to be – [24:24] 20% smarter. He's going to be able to do things he couldn't do today. There's a Saleo quote that [24:30] I keep coming back to where he talked about the aura of inevitability at early Facebook and how when things are real and already kind of close to having the technology there, it's so much harder to say, no, we shouldn't do that.

Yeah. And all of a sudden, designers have the ability to bring the aura of inevitability to the table. And so when you gave that, it's like, all right, shoot, we can't ignore this anymore. You know, it works like he made. Yeah. [25:00] And at this time, I was one of the early and curious in the AI space. Most of my design team that reports me... [25:07] had not dappled in like vibe coding at all. But one designer that was using MidJourney, like that was the extent of kind of AI practice on my team.

I remember showing that example, that story to like the designer that I see that was working on Online Checkout with me. And she's just like, holy expletive. Like I cannot believe that, you know, you designer slash you manager, like we're able to like make that, let alone in like 15 minutes. And also, by the way, having the audacity to like having a VP say no [25:37] Yes, it's possible. So I think, again, maybe going back to the role of a manager thing, it's that courage of being able to push on these tools, A, and B, dock fooding tools instead of just sending them over to your team and hoping that they work.

I want to look at the state of the world today from a slightly different angle because you recently navigated the job market as a leader. [25:58] And I'm wondering if there was anything that felt clearly different this time around or just other signals that you're seeing that kind of point to some of these ways that the landscape is shifting. [26:07] Totally. I mean, we talked a little bit about this sort of player coach being maybe a more en vogue right now. I can't think of a single role. [26:16] for leadership that I've applied to.

And I've been a director for a number of roles. These are various senior positions. I can't think of a single one. [26:25] where they weren't expecting you to be hands-on. [26:27] Period. Full stop. What that actually means is not clear in job descriptions. It sort of varies case by case. But I'll give you an example. When I was talking to an earlier stage startup, they literally put me on a call. [26:40] with an engineer in Eastern Europe, and watched me use Figma to make sure that I knew how to use AutoLayout.

No way. [26:47] Yeah, yeah, yeah. Like, literally, they gave me a design exercise, but literally, it was a test to see if I know how to use Figma. Which, by the way, I did. Yay. Like, I got, you know, like, a path that's up. But, like, yeah, that... [26:58] Career first. Likewise, I don't think the AI... [27:02] tools thing is necessarily something that people are putting on job descriptions, but I think like people have definitely noticed my passion for building. They've noticed that I, between jobs, was not only job searching, but also built an entire company from scratch called Matchmaker with my wife.

I think seeing that somebody is not only kind of like, [27:22] a tinkerer of AI, but literally can do end-to-end product development, wearing the PM hat, the engineering hat, the design hat, [27:31] And then also they're like... [27:32] entrepreneur had of like, you know this perfectly well, like all the other stuff, like incorporating the business in Delaware and like paying the fees and like figuring out your contract with your partners, like all of that stuff. And I think that is something I've been saying for a minute, but like, I do think some of the best design leaders are people that have spent some amount of time being entrepreneurs or working in early stage companies again, because of that ownership thing.

Um, but I do think that I'm seeing more people that are finding, um, [28:01] what previously might have been called quote-unquote personal projects. [28:05] as valuable, right? Like, [28:07] I call this a personal project because nobody hired me to build Matchmaker. [28:11] But, [28:12] It was something that, you know, me and two co-founders created from scratch. It shows the kind of initiative and the resiliency of iterating through it. It shows product thinking. [28:24] It shows technical savviness. It's just all of this stuff. And so I'm definitely seeing more companies that are looking at things that you build outside of work, not as extra credit.

[28:33] but as possibly reasons to get jobs. [28:35] in addition to or even over [28:38] traditional work experience. [28:39] It's funny, I have a lot of design leaders in emails and Twitter DMs of people who are asking to come on the show. It's a different lens, but what I thought was so interesting about you was Matchmaker, too, for the exact same reason, where it's like, oh, man, not only do you have the pedigree, but talk about hands in the clay. There's no level of depth that you can get beyond building a totally new product and company going zero to one on the whole thing.

That says so much about who you are. [29:09] I'm curious what that process looked like. Maybe just were there specific, I don't know, lessons learned or hurdles that you had to overcome that you think people listening who are inspired to do a similar journey or to just start building more would benefit from seeing? I think many of us probably have a lot of personal project ideas in our head of problems that we have in our own lives that we want to solve. This was different. This was my wife, Melanie. She's in marketing.

She's been marketing for her whole career. [29:39] an agency specifically in what's called brand partnerships. I am an outdoor goods brand. I'm a luxury brand. I want to get more people to notice me and to build up a certain brand equity and to get people to buy my products. Partnerships is like, okay, well, let's find other like-minded organizations or brands or creators and find ways to work together. [30:00] so that we can have a win-win situation, leverage each other's audiences, so on and so forth. And so what Melanie and her partner noticed was that they were in all these Slack communities throughout the world, you know, that are all about marketing, and people were like, hey, we're doing the Venice Biennale, you know, in a couple of months.

We're looking for whatever, like influencers that are, you know, interested in, you know, marketing. [30:21] the outdoors or whatever, right? So like there's constantly these like little mini Slack-based RFPs that are just falling into the ether. And so Matchmaker was really an attempt to solve that problem in software. Now, in terms of the process, you know, I... [30:38] I had my in-house PM/researcher/founder, which is my wife. She was my source of wisdom on who the users are. [30:48] how they might behave, things they're looking for, [30:51] To be honest, I think we are now in our third build of the product.

Wow. And just to kind of paint the picture, we started thinking about this, again, probably about a year and a half ago, when I feel like the AI tools were okay, they were fine. I didn't know I had to necessarily build a whole custom thing using Coursera Cloud Code. There were a bunch of off-the-shelf products. The one was called Softer at the time, with no E. It's almost like Framer with a little bit more built-in functionality. [31:18] I was like, oh, this could work for an MVP. Let's try it. And then one...

[31:23] It was ugly as hell by the end. And I was just like, as a designer, I can't. I can't. After a few months of that, we already saw that the capabilities of Cursor, Lovable, started becoming a thing. And Lovable actually really caught my eye. [31:36] And I'll say two things. One, as somebody who studied computer science and has learned six different programming languages at some point in my life, I was tempted to be like... [31:45] all geek in on like, let me just code this by script from scratch. But I knew...

[31:51] that there was a good chance that I was going to go back to a full-time job. And I had this dream that I could build a product and hand it to my wife and her partner, who are not necessarily technical, and they could run the business. [32:04] in lovable without me actually [32:07] being involved. That was the dream. And so I was like, I'm going to choose lovable, even though it doesn't scratch that geek kind of part of me to see. The first time I built something, zero to one,

[32:19] I very much replicated my own process as a designer. What I mean by that is literally conversations, like lots of discussions with my co-founders around like, who is our user? What are the problems we're trying to solve? Literally writing a strategy document, writing a PRD, like we have artifacts for all this stuff, using that to basically generate information. [32:39] a series of prompts, [32:41] which I then fed into Lovable to create the first version. [32:45] The first version, as you can imagine, absolutely terrible and very purple. But just to kind of start to build [32:52] the foundations, right?

And so I almost thought about that first iteration, if you will, of Matchmaker. [32:58] as what I almost call a build wireframe. It allows you to do the core functionality, and engineers have been doing this for a long time, by the way, this is not new, but you're basically building the skeleton of the flow. You have a homepage, the homepage is going to have recent listings on it. It's going to have maybe a navigation that has a notification area, if you have a chat from another brand. We had all the elements, [33:23] It was ugly, it was an intuitive, half of it didn't work, but it was there.

And that's, I guess, where the word vibe comes from, in vibe coding. I slowly started to build a design system. [33:35] in Figma at the time. I know some folks aren't using Figma anymore, but I found it very useful to build, let's call it five to eight, [33:42] high-fidelity mocks of what I wanted the experience to look like. I created a very, very humble—design system is probably an exaggeration—a sticker sheet [33:52] of components of like, you know, button, button hover state, right? Like my type, scale, color palette, a few other things, right?

And... [34:02] I literally just had... [34:03] lovable, ingest that, ingest the screens, and say, update across the site everything to these new high-fidelity visual designs that I made. And by the way, the reason I did it this way, again, going back to my [34:15] you know, old school design process that we didn't necessarily know what the flow should be. [34:19] We were almost prototyping it to feel what it looks like in that low-fidelity wireframe stage. We tore some stuff down. We had a few iterations in that ugly stage to just make sure that it felt right in terms of the architecture.

Then we went into, "Okay, now let's make it look awesome." Now that it looks awesome, we are living in the world of high-fidelity from now on. We have a design system. We have a type scale. My wife is launching features without me all the time. [34:48] She literally can create entire new pages and it looks on brand. It uses all the right things. And even today, Lovable is so much better than a year ago that also makes really good design decisions. Yeah, that's good. [35:10] not to mention an incorporated business.

It takes payments. We have real users. We have real listings. But we're still very much in like, [35:19] the early stages. And what I mean by that is [35:22] People are talking about this, I think, a lot on social now. Because anyone can build something from scratch, if I build something from scratch, we are all finding that building software isn't as hard as it used to be, but growing an audience is as hard as it always has been. There's one question that I can't stop asking myself. What if companies applied to talk to you rather than the other way around?

And that question is the foundation for the all-new Dive Talent Network. [35:52] Like right now I'm helping many of the most exciting startups that I know to hire the designers and builders who listen to this show. So if you're curious what might be out there and maybe you want to get on my list or maybe you're even looking for your next design hire, head to club/talent to join today. I think I want to tap into your experience now having quite a few reps under your belt in terms of actually vibe coding, building software with AI.

Not only [36:22] the little one-off low-fidelity prototypes internally, but like literally going zero to one on a product and building that through different phases and rebuilding it. And I would imagine that you've picked up some lessons and experiences along the way that have kind of shaped the way that you think about interfacing with AI and getting the most out of this technology. I'm [36:44] clear ways that your own process as a builder has evolved, or maybe just different ways that you approach the tools or anything at all that people, again, who maybe have been kind of on the sidelines a little bit could learn from.

Yeah. I think a lot to unpack there. I think one, you know, I, I did, as you mentioned, like I had built a bunch of stuff since then, everything from another like SAS tool that I'm working on that may or may not launch. It's something I'm experimenting on. It's like almost like helping people look for jobs and coaches in [37:14] you [37:15] Just for comparison, like the first version of Love of War probably took me a few months. Getting to a decent version of this took me probably a day. [37:21] Whoa.

Right? Some of it has to do with the power of these tools, but some of it, to your point, is about just being a little smarter now that I know how the AI thinks and works. I've also launched a bunch of experimental art stuff. Again, I think there's a few things I'd call out. I think one is thinking about how you plan for a project. And I think this is a skill set that... [37:44] designers and PMs should already have to some extent, especially if you're on the more senior side, which is like all the usual exercises still help.

[37:52] Thank you. [37:53] of really clearly defining what is the goal of this product, [37:57] Who is it for? What are the critical user journeys that this product is supposed to handle? Like even walking through, you know, and this is all in words, right? Like, [38:06] writing this stuff down in a doc. I've even seen some people dictate using a microphone, if that works for you, but just getting it down in raw, ugly ways. And what I've actually been doing is taking that initial, we'll call it a strategy slash PRD kind of hybrid thing that I've written.

I will drop that into Claude and basically say, hey, Claude, I am building something that's... [38:28] blah, blah, blah, right? I literally dumped that [38:31] ugly, typo-ridden sort of PRD into it and say, like, make me a series of prompts and a plan for how to most effectively build this in, and then I'll save the platform. [38:42] in Lovable, in Cloud Code, in whatever. Because, I mean, these tools now are so self-aware of themselves and of these platforms that they can actually understand how Lovable builds stuff. And so they will, Cloud will literally spit out an entire plan.

It will ask you questions about your plan and identify gaps in your thinking, which is amazing. You've probably seen this as well, but the Cloud interface has really evolved to [39:09] literally have in-line interactions of like, hey, I noticed you wanted a notion of a brand. Like, what constitutes a brand? You know, like you literally, or do you want me to make this brand public or private or both? And like, it's like, so there's just like, it's a lot smarter and it can almost like help you a ton of... [39:27] with the pre-planning.

So I think that's one area that's been helpful for me to kind of get that first build out the door. The second thing that so far has proven true to me, I'm curious if you have a different opinion on this, is that... [39:41] I've generally found that we try to build everything at once. [39:44] with any platform, it's kind of a disaster in a way. I prefer to kind of build things in pieces. And so sometimes Claude will recommend that. Sometimes I will ask Claude about that. Like, let's actually thank you, Claude, for your plan.

Now, [39:58] Walk me through a plan on how to basically create a roadmap or stagger this build out. [40:04] And so, as an example, with Matchmaker, they will start with a few of the key screens. We're not going to mess with settings yet. We're not going to mess with chat yet. So we're literally building out things in phases like you would a sprint. Each sprint might be... [40:18] 10 minutes instead of two weeks, but you're still doing things in sessions, right? Where you're kind of building a thing, checking it, making sure you're not burning through a thousand credits doing it.

And like, you're really like, you're like kind of doing this in pieces. And as you're doing that, you and the agent are building a mutual understanding of the product and of each other, which is really interesting. It starts to understand you. By the way, something I forgot to mention, like all the initial context, that PRD and all that stuff, I think some platforms like Claude are much better at like long-term context. Lovable hasn't been, but there are places within [40:48] save context. And so like, that is something I also have done.

It's like, make sure there's a place that sort of like, [40:53] the project memory, right? Like kind of your stored context for like what this thing is, that it can keep referencing to understand like, oh wait, I'm building a mastermaking service for brands, not... [41:04] whatever, some email platform. That context seems to really help these platforms quite a bit. I actually think I have a Substack post on this. I don't even remember. I think I wrote 12 points on how to save tokens, but asking it to be less wordy, more concise, asking it to check its work.

Visuals, I mean, this is where I feel like there's a big divide in design right now. You'll have to pry Figma from my cold-wired hands. It might happen eventually, but like, [41:32] I just love working visually. I'm a show versus tell person, and that's even the way I lead teams. [41:38] I'll sketch out an idea I have instead of just using words. And so when something is just off in Claude, [41:44] I could back and forth with it in words for like 10 minutes, or I can go to Figma and sketch it out in five minutes.

And it's probably going to be closer to like the pixel perfect version I have in my head. And so I will very often kind of like, [41:58] dual task between AI building and Figma tools at the same time. It'll build something and I'll be like, "Ooh, that spacing is a little bit off." And I might guess move it up six pixels. Or if it's something bigger than that, I might literally just design that little component or a part of the component and be like, "No, this is how I want." [42:17] the avatar to look next to the name of the brand and the, [42:21] favorite button, right?

And so I think that's just something that everyone's kind of got their own workflows, but like for me, the design tools have still been, you know, [42:29] such a helpful kind of stopgap because AI does seem to do a lot of stuff on its own, inspired by, you know, like the millions of other designers it's being trained off of. And so I guess that's the last part of this too, is that like, you know, I think we joke about the purple-ness of AI, but I do think that you have a lot of non-designers right now that are looking at the outputs of AI tools and they're like, oh, that's pretty good.

But like a lot of them, as we both know, [42:52] look very similar, and that's because they're literally all being trained on the same [42:56] world of stuff. And so I think the last thing I just really try to encourage people is like, don't wait till like the very end to think about branding and differentiation, like really try to like, I mean, in general, like I think once you know what the product is, what it's for, I feel like that is a conversation that's, [43:14] and some definition you should have as early as possible to start to infuse some of that soul, and some of that brand and point of view into the product.

That's been my experience too, where [43:25] If you have the nugget of what you want the visual language nailed down in the beginning, Claude's really good at... [43:31] extrapolating it [43:33] And yeah, maybe sometimes it'll go a little too far. And you're like, okay, no, no, no, I don't want that. [43:37] And maybe in that sense, I will design it in the canvas. But every once in a while, it'll do something based off of my initial brand language where I'm like, oh, actually, I kind of like that. Maybe I would do that over here, you know, and it almost helps me scale my own thinking.

And I was kind of chuckling with you talking about the canvas tools, too, because same thing. It was like, I'm only in a canvas. And then all of a sudden, I'm like, oh, my gosh, I can code now. And then the pendulum swung all the way. [44:07] and to reach for different types of tools. And I'm having a lot of fun being creative in that process even. Before I let you go, I have two total out in the left field hypotheticals that I want to toss your way, just to make sure that we've covered everything.

[44:23] The first goes back to more like team building stuff. And... [44:29] I kind of want you to imagine that you are... [44:32] Maybe it's even in your current role. You get to build a new zero-to-one design org within the broader team. And you get to do it from scratch, new headcount, everything. How has AI impacted the way that you think about AI? [44:49] team building, role definition, or maybe even like the types of skills or traits that you want to prioritize on that new work. I really do believe that now because every function has access to the same tools, everyone can build something that looks like a product.

[45:05] I think still the things that we – [45:08] can do better than AI for now is one, [45:13] are bread and butter designers, which is like, how do you think about what problem am I trying to solve? Right? Like what user problem am I trying to solve? What business am I trying to solve? And what is the experience that [45:25] best suits that problem. Some people would call that more generally product thinking, but I think that has always been a very strong criteria for me for senior and above designers.

I think that is something that would be a non-negotiable for designers in 2026. You can't just be execution. You can't just be order takers. Not that I think designers ever should be, but that is no longer valuable because [45:50] a product manager doesn't need you. [45:52] anymore to do that one to which we talked about as well a little bit so so i think that's one kind of skill set and i think like scrappy research is definitely something that i think is still a valuable trait for that like every does every firm i've ever worked for every company i've worked for has always been under source of research so i still think that designers that like have the boldness and the courage to like find ways to like do scrappy cafe testing or like

com or whatever it is and know what that looks like no one is useful and like just do [46:22] second one [46:23] We talked about this a little bit, it's like that point of view. Some people call it taste, I find that a little pretentious, but I will call it brand voice, brand positioning. How do you differentiate and see of tools that are already coming out and they look exactly identical, [46:37] because they're all being generated by the same... [46:39] agents, basically, or could. How do you differentiate, especially in the entrepreneurial world of startups?

Or zero ones, it's most relevant. But that ability to swing between product design and a bit of branding, [46:55] and to some extent visual design as well as I think is very important. You know, so there's moments of delight. This is something I really tried to do with Matchmaker. You know, like... [47:04] you build products. I know you can feel the sympathy. Like when you're building products, I have found myself much more forgiving a visual design because I'm like, it's just lots of work. It's been so hard to just get to work.

Like, well, I'm not going to worry about every little pixel. Right. But, [47:16] Actually, I... [47:18] like once I get it to work, I really do find, well, you know what, like, [47:21] What's stopping a competitor from literally vibe coding the same exact thing tomorrow? Yeah. [47:25] it'll take them a day or two, right? It's not that. So like finding the customers, [47:29] Number one, like real growth stuff. And then two, like having a really differentiating product. [47:35] that feels more premium, has an emotional connection with its users. Those are things that fall squarely in the design world.

So I think those are two sort of non-obvious skill sets, maybe three there, product thinking, research, and sort of branding that I think are extremely powerful. The last one I'll say is people that have a somewhat technical background, [47:56] are not afraid to look at a terminal and be like, what in God is this? You know, and like be, and I didn't say like read, reading the output of quad code, [48:05] and what it's doing and understanding it actually makes you a more successful builder. And so I think that's another sort of like persona that I'm looking for a little bit, are people that maybe studied a little bit of computer science.

Yeah. Or people that people have been designers that have coded a little bit or have been design engineers. I think that those skills, even though technically, yeah, AI does it all for us. I think the skills are really helpful because I have certainly found myself where I'm like, [48:30] "Okay, Lovable, I know what you're doing." Like you're stuck in like a four loop or something, right? You're stuck in sort of this world where it's just like recursing over some weird thing, and I know how to help it debug itself. And I really do think that is like a muscle I've built [48:43] as like a minor in CS back in the day, [48:46] that I can't explain how my brain has somehow applied it to this world, but it still does.

[48:53] I would say my dream design team right now is, and again, I think that's why hiring is so hard. We are asking a lot of people, but it's that T-shaped generalist that maybe has a few of those areas. Now, as a leader, I've always believed T-shaped means that it is your responsibility as a leader at a company. [49:11] to understand what people's strengths are, what their passions are, and to like know how to grow people in the areas to make them well-rounded. So like, I certainly am not that person that will only hire people that are, [49:25] checking off every box on my hiring list, right?

Depending on the role, I might have a certain non-negotiable, like consumer mobile, it sounds like a big part of my world, right? Like, [49:35] if you've just done like [49:37] enterprise SaaS your whole career, maybe a little trickier, depending. But if someone's never done research before, [49:43] I will train you or I'll connect you with a researcher and pair you up and look at you. Moments to safely start to feel comfortable in those moments, right? If you're not as much of a product thinker, visual designer, this gets a little harder.

This, I think, just kind of comes through... [49:57] Visual design, to some extent, I think is maybe education or self-education. And then probably thinking, honestly, I just think is... [50:04] experienced to a lot of extent. A lot of what you're saying, even I'm kind of noticing in playing this role, connecting, I guess my own sort of matchmaker, you know, kind of think a lot of brands and designers and it's super life-giving for me. But something that I'm noticing is [50:18] there's a real big uptick in demand for more visual brand designers.

A lot of people are using the phrase brand engineers because they want you to be more [50:28] They want you to adopt the builder mindset, but be the person that can really push what the visual identity of this product is for it. And I think my understanding is that it is coming from this... [50:40] need to... [50:42] elevate beyond the baseline because everybody's getting to the baseline really, really, really quickly right now. And I think specifically, all led, yes, and I think motion design is one of those things that is so huge.

I mean, I have said this for a long time before AI. I think... [50:56] In a world where a lot of product design is very similar and flat for practical reasons, how many times can you design... [51:04] a lung feed with a carousel of cards, right? Like there's, [51:07] a bunch of ways you can style that and do that. But like, I really think a lot of brand expression today can come with motion design. That is, and I think it's a very underutilized skill by product designers and, and, [51:18] as we all know, it can be so bad when it's bad.

It's so good when it's good, right? I mean, I have a very close colleague that is a real legit motion designer, and he's just like, less is more, obviously. He's like, be very subtle, nothing worse than a dancing hot dog type of moment on your UI. So I think that is one of those areas that, again, the AI tools right now are not going to surprise you with motion, with an amazing motion thing. That is just not going to do today.