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- [00:00]
Ron Golden
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, I don't know why I'm so excited right now. Like, I think designers are literally have this superpower.
- [00:35]
Rid
Welcome to Dive Club. My name is Rid. 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
- [00:53]
Interviewer
in this new AI world. So we're going to do a deep
- [00:56]
Rid
dive into his journey as a builder, including how he built a new product called Matchmaker from scratch. But before, before we get into all of that, I asked Ron to share a story of what it was like
- [01:09]
Interviewer
as an early designer working on Uber Eats.
- [01:12]
Ron Golden
I remember, like, my first week on the job living in New York City. Had never done a delivery before in my life. Wanted to play the product, and so I 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, basically can check out a bike and, you know, you get it for 45 minutes or whatever. And so I remember taking 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 awful. I finally ended up getting the driver app to work. I push a button that says go online and I'm just like sitting there and like, nothing is happening. And 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 the first few months of my Uber Eats tenure, like, was really like, more almost like of a research role than a design role. Because Uber at the time, like, really had this strategy of, like, even though it was like a pretty large company, like Uber Rides was in hundreds of cities, it still acted very much like A startup. So like, you know, the driver app, they literally just like 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 deliveries, first in New York City, 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 whole lot, which is 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, in Tokyo, in Bangkok. And these are places we actually traveled to and of course found 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 actual apartment is like a 15 minute journey through like multiple gates of security. Like there's no landmarks. And so like, you know, we would literally ride around these cities with translators trying to figure out, you know, which way to go, like dodging traffic, almost dying, like all of that stuff. One of the things I really wanted to do is figure out ways to sort of bring that feeling of like, the fear, the anxiety, the pain of like 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, but.
- [03:47]
Interviewer
Oh, wow.
- [03:47]
Ron Golden
Yeah, yeah, yeah. So I had recorded all of these trips using a very early generation of the Insta360 camera. I would mount it to the bike and I'd literally record these trips to like literally capture what it's like to be everything from dodging traffic to figuring out like which way to go. And Maps is telling me the wrong directions to like even having security guards tell me like, no, you can't come in without certain credentials to like deliver food. So I was just capturing all of this stuff and so I, 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 like Uber Eats, Uber Rush, a bunch of other products. This is Jason Drohovi. You watch. He like literally watched the videos of, you know, me 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 sent to him because our assumption up until this point was like, service the big restaurants, right? Like, they're getting all the traffic, right? And so I was trying to like, replicate that. And like, this guy literally was suffering in his car, he hadn't eaten. He like had to go to the restroom and like, couldn't, couldn't do anything but wait. So that was the beginning of pretty heavy product and design investigation into, like, why is this happening? And what we realized, which now is kind of common sense, is like, if all of the couriers are being told to go to the hot restaurants, then there's too many couriers 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 Maps or Yelp or whatever to find popular restaurants. And like, they would 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, hoping, right? So it was the beginning of like a long project that ended up with a, like a really robust way to kind of visualize what we called hotspots. So places that like, aren't like the tried and true places that you might imagine have a lot of demand. Demand, but like places that might even be like a small mom and pop Chinese restaurant but that like all of a sudden happens to have a little pop of demand, right? And so a was a way for people to like, start to sort of spread out their efforts across the city. The other one, which is really interesting was like a lifestyle thing, which is like what people used to do, which is crazy, is this guy in LA used to drive one and a half hours to get to that sandwich shop that had no business because he figured in his own neighborhood in like Ventura, California, there wasn't enough demand. Well, guess what? There was. We just didn't have the tools to say it. So now he could stay, like in his neighborhood, 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.
- [06:44]
Interviewer
Real quick message and then we can jump back into it.
- [06:46]
Rid
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. Even so, this is going to make it a breeze to keep everything in sync and it's available today. Just head to Dive Club Slash Jitter to get started. I have anticipated Desen'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 preloaded inside of Destin as starting points, so you can easily make changes, explore ideas, and then when you're ready, you can share your prototype
- [07:38]
Interviewer
in a single click.
- [07:40]
Rid
Destin is the only design tool that allows you to design on existing pages and flows pulled directly from Prod, which
- [07:47]
Interviewer
is a pretty big deal for teams.
- [07:49]
Rid
And you can get started today. Just head to Dive Club. Desen. That's D E S sn.
- [07:57]
Interviewer
Now on to the episode. You can tell that you're a researcher at heart, just how quickly you're just like, I'm just gonna do the whole flow end to end. But there's definitely a version of this story where you put things into 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 to three quarters later, you know? And so the part that I think is so interesting is how you. You captured all of the video. Like, you're like, I'm going to think very intentionally about how to transfer this empathy. And ultimately, it seems like that played a big role in motivating people to actually take action.
- [08:31]
Ron Golden
Jason Droege and my manager at the time, Andy Zabolsky, he supported me to actually get that video in front of the entire Uber Everything organization. Like, Jason was like, people need to see this. Like, our PMs, our engineers, our ops. People need to really understand, like, firsthand, like, what that pain is. And so what we did is we cut, like, a version of that video down from obviously two and a half hours to, like, three minutes. But even that three minutes, we showed it in all hands and we just, like, left a minute. We left a minute in that presentation of just like the feeling of sitting in a car waiting for nothing to happen, right? And, like, you know, you've probably been in an all hands of a company, or maybe you, maybe you haven't, I'm not sure. But you know, they tend to be packed with content. And so like the power of having like hundreds of people in a meeting where we're all just like sitting there awkwardly waiting, looking at the app, nothing going on. 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 scaled and capturing the insights and all that stuff. So like the appetite, I think for 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, 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, right, to just go out and do it right yourself and know that you're going to fail and that's okay.
- [10:21]
Interviewer
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 you know, 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 spanned so many different companies, so many high impact roles. Is there another example that we could talk about just to give people an idea of what this moment looks like in practice and then how you show up as a designer?
- [10:52]
Ron Golden
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 Shopify.com checkout or something like that. They have this marketing page and in big bolt, you know, 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 and is already great. Okay, so that's Challenge number one. And then imagine that the CEO of Shopify, Toby Luca, is telling your entire team, we need to redesign checkout, 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. That is his DNA. Like he's always looking to like, you know, tear things down and build them up again, like question things, make things better. I would say, like, that was a surprise to me when I joined the company. I joined at maybe Vaccine the Perfect. In the time I was there, we launched the partnership with OpenAI. So we were like one of the first companies in the world to basically have that agentic e commerce experience within the chat interface. We launched Cryptocurrency with Coinbase. So the first time Shopify had crypto globally. And the stick I redesigned and this was like my first six months at the company. I don't think I've ever shipped that much in such a short time during a ramp up period of unemployment in my, in my world. And honestly, I loved it. Again, I kind of brought that same energy that I had in those beach days of like a company that like, yeah, technically is public, technically it's on the stock market, but it really operated like a scrappy startup. You know, this is where I would say I had worked in like kind of AI adjacent, you know, before we all talked about OpenAI, ML based product work, all that. But I think that Shopify was really my first foray into like cursor and you know, like that sort of vibe coding world, like at the time. And again, just to frame this is like a year and a half ago. Like this is 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 at the time and a bunch of people, like we had the 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 like clunky and just like not very like, yeah, there's all these things you have to know and like you could just ask Claude because it didn't have the answers to this stuff yet. So we're just like figuring it out. And it was just really fun to be part of this like little crew 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 what 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, little NFC stickers and just like if you want a ticker, 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 thing that can talk to an NFC sticker. And in, I'm going to say eight hours tops, we went from 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 you sell. And then a customer can take the shop app and just hover. They don't have to unlock their phones. Hover near that sticker and you have like a little notification that's like product detected or whatever tap on that basically says, oh, this is like a blah blah sweater, you know, made of, you know, 90% wool, like and price and reviews and 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, 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 barred an Engineer for like 30 minutes to say like, hey, can you help us with that thing that we were stuck on? Because again, probably today cloud code would do this like heartbeat. But we didn't help that.
- [15:42]
Interviewer
You kind of had to earn it back Then, yeah, I say back then, it's only a year and a half ago, which is. Is insane because you have this really storied 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.
- [16:11]
Ron Golden
Yeah.
- [16:11]
Interviewer
Where do the biggest deltas exist?
- [16:13]
Ron Golden
I think you're definitely seeing a lot of different ways people have framed it, but essentially like a flattening of a lot of orgs, right? Like less layers of management. That in of itself means, you know, if you are a manager at a company, that can mean a few things. Like one, you probably have a lot more reports maybe than you're used to. Like, 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 am 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 of that on the side as well. I'm seeing more employers, especially like pre IPO companies that are looking for this like player coach type, which is, you know, I mean, there's probably a lot of ways you define it, but for me it. It does often look like maybe managing a smaller team. Like in my mind, that is like a Shopify size thing of like 2, 3, 5, 6 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 just doing performance reviews and alignment meetings while the ICs are doing the things that 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 where I find I'm either asked to or spend my own time. One which you talked about is like zero to one stuff. Like if I'm on a product team and everyone's thinking really incrementally. 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 buy code, something that people can react to and see. Because in 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 or like your emotion is literally I want that, you know, like I want to ship that to our customers. Like that's the area I spend a lot of time. And so any minutes right now that I have, I am like 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 like an idea for like a new digital wallet or something like that just to kind of show teams like 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 people can pick them up actually means that it no longer, you know, for a manager to like make something on the side, is no longer setting aside a couple of days to like build out your components in Figma and create something in auto layout and then put string up a prototype. Like you can do that in like 100th of the speed. And so I think for 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 like manage people. Like there's absolutely a place for that in the world and it's super important. But like I love problem solving, I love being close to the problems and like seeing the users and talking to them. And so that's, that's been really exciting for me to like know that that's actually becoming more of a viable career path again for people that are like kind of on that fence between those two worlds.
- [19:44]
Interviewer
I hadn't thought about it that way. It's very obvious in retrospect but like you hear the whole prototypes of the new PRDs or some version of that statement. But you're right, it's not just that we have the ability to communicate more effectively, but the opportunity cost of 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.
- [20:10]
Ron Golden
I've done prototypes in like Figma make or quad code in like 10 minutes between meetings while grabbing a cup of coffee. There's an example actually, and it's on my website too, of like a moment that I had at 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, you know, which is like, we're trying to make a more expressive version of online checkout, right? And there are certain assumptions for what that would look like. Those assumptions were that merchants would actually have to like, do something to like make their checkout more beautiful, more branded. Like they might have to upload some high fidelity SVGs of some logo or something, or, you know, customize some colors. And like, one thing we knew from research at Shopify is that merchants, especially SMBs, small, smaller merchants, small medium business merchants, either don't have the time or are super tech savvy and they just might not go through the motions of doing that stuff on their own. And so in 2025, 26, 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 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, you know, again, pre2025, what would a designer do? They would ask an engineer, like, can this be done?
- [21:55]
Interviewer
Totally.
- [21:56]
Ron Golden
Which, which by the way, I did, I did. And engineers are like, not sure, don't have time to answer your question.
- [22:00]
Interviewer
Which I could have told you that was their answer.
- [22:02]
Ron Golden
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 Said I went into Cursor at the time and like Vibe coded an internal tool to try to do what I just described, which was literally, it's the ugliest thing ever. But it was literally just like a form where you can type in outdoorvoices.com right? A brand. And it would basically just like suck all of the possible colors variants from the site that could potentially be the brand colors, including, like, it's intelligent enough so it'll be like, oh, like this was used for all the buttons. This is probably a primary 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, you know, look in the header, look where forever you can like, 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 prayed. I'm like, maybe this is the thing. And so it's like, great. Found an API that does that, that's open source and it just sort of built the whole thing in. And then while 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, 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 again, that world of like, I don't know why I'm so excited right now. Like, I think designers are literally have this superpower, like unknown superpowers, right? Like, I just didn't even know that Claude would be able or Cursor 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. Like, I'm literally just like throwing stuff into, you know, the AI black box. And I'll tell you, like, having been Vibe coding now for two years, like 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. Like, that's such a fun and weird thing about this moment is, like, you can't even claim to be an expert on any of this stuff because literally, like, next month, it's going to be totally different. 20% smarter to be able to do things you couldn't do today.
- [24:28]
Interviewer
So there's a soleo quote that 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.
- [24:44]
Ron Golden
Yeah.
- [24:44]
Interviewer
And all of a sudden, designers have the ability to bring the aura of credibility 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 it.
- [24:55]
Ron Golden
Yeah. I'll add one thing, too, that I'm remembering this part of kind of my experience was that, again, at this time, like, I was one of the early and curious in the AI space. Most of my design team that reported to me had not dabbled in, like, five coding at all. We had 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 an online checkout with me, and she's just like, holy expletive. Like, I cannot believe that, you know, you, designer, slash, you manager, like, were 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 and then being like, actually, yes, like, it's possible. Right. So I think, like, again, maybe going back to the role of a manager thing, it's like that courage of, like, being able to. To sort of push on these tools, A and B, dog footing tools, instead of just, like, sending them over to your team and hoping that they work.
- [25:51]
Interviewer
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, 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.
- [26:08]
Ron Golden
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 for leadership that I've applied to and you know, I've been a director for a number of roles. These are very senior positions. I can't think of a single one where they weren't expecting you to be hands on, period, full stop. What, 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 with an engineer in Eastern Europe and like watched me use Figma to make sure that I knew how to use auto layout.
- [26:47]
Interviewer
No way.
- [26:48]
Ron Golden
Yeah, yeah, yeah. Like literally they gave me a design exercise and 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 I passed that. But like, yeah, that career first, you know, likewise. I don't think the AI 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 a tinkerer of AI, but literally can do end to end product development wearing the PM hat, the engineering hat, the design hat and then also the like entrepreneur had of like, you know this perfectly well, like all the other stuff like incorporating the business and 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. But I do think that I'm seeing more people that are finding what previously might have been called quote unquote personal projects as valuable. Right. Like I call this a personal project because nobody hired me to build Matchmaker, but 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, 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 built outside of work not as extra credit but as possibly reasons to get jobs in addition to or even over traditional work experience.
- [28:40]
Interviewer
You know, it's funny, like I have a lot of design leaders in emails and Twitter DMS of people who are asking to come on the show. You know, 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 like, talk about hands in the clay. There's just, there's no level of depth that you can get beyond building a totally new product and company. Going 0 to 1 on the whole thing, right? Like that says so much about who you are. So I'm wondering if we can maybe even just get a little bit of behind the scenes. 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?
- [29:24]
Ron Golden
I think many of us probably have a lot of personal project ideas in our head of like problems that, that we have in our own lives that we want to solve. This was different. This was. My wife, Melanie is a, she's in marketing. She's been marketing for her whole career. And then she got the entrepreneurship bug and started a, an agency, specifically in what's called brand partnerships. You know, I am a, an outdoor goods brand. I'm a luxury brand, right. 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. Right. Partnerships is like, okay, well look, let's find other like minded organizations or brands or creators, right? And like find ways to work together 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, the outdoors or whatever, right? So there's constantly these little mini Slack based RFPs that are just falling into the Ethereum. And so Matchmaker was really an attempt to solve that problem in software. Now in terms of the process, I had my in house sort of pm, researcher, founder, which is my wife. She was my source of wisdom on who the users are, you know, how they might behave, things they're looking for. But to be honest, I think we are now in our third build of the product and just to kind of like paint the picture like we Started thinking about this again probably about a year and a half ago when I feel like the AI tools were, they were okay, they were fine. I didn't know I had to necessarily build a whole custom thing using Cursor or cloud code. There were a bunch of off the shelf products. The one was called Softr at the time with no either. It's almost like Framer with like a little bit more built in functionality. I was like, oh, like this could work for an mvp. Like let's try it. And then one. It was ugly as hell by the end. And I was just like, as a designer, like I can't, like I can't. After a few months of that, like we already saw that the capabilities of Cursor Lovable started becoming a thing. And Lovable actually really caught my eye. And I'll say two things, like 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 all geek in on, like, let me just code this by script from scratch. But I knew that there was a good chance that I was going to go back to a full time job. And I had this like 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 in Lovable without me actually 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, I very much replicated my own process as a designer. And 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? Like literally writing a strategy document, writing a prd. We have artifacts for all this stuff. Using that to basically generate a series of prompts which we then fed into. I then fed into Lovable to create the first version. The first version, as you can imagine, absolutely terrible and very purple. But just to kind of start to build the foundations, right? And so I almost thought about that first iteration, if you will, of Matchmaker as like what I almost call kind of like a build wireframe. It's like it allows you to do the core functionality. And engineers have been doing this for a long time by the way, right? 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, right? It's going to have maybe a navigation that has a notification area if you have like a chat from another brand, right? Like this. We had all the elements. It was ugly, it was non intuitive. Half of it didn't work, but like it was there. And that's I guess where the word vibe comes from. And vibe coding. Like I. I slowly started to build a design system in figma at the time. I know some folks aren't using FIGMA anymore, but like I found it very useful to build, let's call it 5 to 8 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 of components of like, you know, button, button, hover state, right. Like my type, scale, color palette, few other things, right. And I literally just had 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 old school design process that we didn't necessarily know what the flow should be, we were almost like prototyping it to sort of feel what it looks like in that kind of low fidelity wireframe stage. We tore some stuff down, we had a few iterations in that kind of like ugly stage to just make sure that it felt right in terms of the architecture. And then we kind of went into like, okay, now let's make this look awesome. Now that it looks awesome. I mean we are living in the world of high fidelity from now on, right? Like we have a design system, we have a type scale. My wife is like launching features without me all the time. She literally can create entire new pages. And it looks on brand, it uses all of the right things. And even today like lovable is so much better than a year ago. That also makes it really good design decisions. Yeah, it's good, you know, so I've been just really impressed even seeing how it's evolved over the past. But I'll just say we kind of got to a certain point in terms of where we are where it is now fully functional, 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 the early stages. And what I mean by that is, and people are talking about this, I think a lot on social now because anyone can build something from scratch, vodka, 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.
- [35:39]
Rid
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. And, and it's working. 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
- [36:03]
Interviewer
out there and maybe you want to
- [36:04]
Rid
get on my list, or maybe you're even looking for your next design hire, head to Dive Club Talent to join today.
- [36:12]
Interviewer
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 the little one off low fidelity prototypes internally, but like literally going 0 to 1 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 curious if you're able to see clear ways that your own process as a builder has evolved or maybe just different ways that you approach the tools or anything that all that people, again, who maybe have been kind of on the sidelines a little bit could learn from.
- [36:57]
Ron Golden
Yeah, I think a lot to unpack there. I think one, you know, I, I did, as you mentioned, like I have built a bunch of stuff since then. Everything from another like SaaS tool that I'm working on that may or may not launch something I'm experimenting on that's like almost like helping people looking for jobs and coaches in the design industry. So just for comparison, like the first version of Lovable probably took me a few months. Getting to a decent version of this took me probably a day.
- [37:21]
Interviewer
Whoa.
- [37:22]
Ron Golden
Right? Like some of it has to do with the power of these tools, but some of it, to your point, is about like just being a little smarter now that I know how the AI thinks and works. I've also like launched a bunch of like experimental art stuff. Again, like, I think there's a few things I'd call out. I think one is, you know, thinking about how you plan for, you know, a project. And I think this is a skill set that, that 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 of really clearly defining what is the Goal of this product? Who is it for? What are the critical user journeys that this product is supposed to handle? Even walking through. And this is all in words, right? 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 like taking that like initial, like this 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 blah, blah, blah, right? I'll literally dump that 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 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 like how Lovable builds stuff. And so they will, Claude will literally spit out like an entire plan. It will ask you questions about your plan and identify gaps in your thinking, which is amazing. Like you've probably seen this as well. But like the Claude interface has really evolved to like literally have inline interactions of like, hey, I noticed you wanted a notion of a brand. Like what, what constitutes a brand? You know, like you literally. Or, or do you want me to make this brand public or private or both. And like it's like, so there's, there's just like, it's a lot smarter and it can almost like help you a ton 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 I've generally found that we try to build everything at once 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 walk me through a plan on how to basically create a roadmap or stagger this, this build out.
- [40:05]
Interviewer
Right?
- [40:05]
Ron Golden
And so you know, as an example, you know, with Matchmaker, like maybe we'll 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. We're right, so we're like literally building out things in faces like you would a sprint. Each sprint might be 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 kind of doing this in pieces and as you're doing that, you and the agent are building a mutual understand 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 that 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 lovable and you can save context. And so like that is something I also have done is like make sure there's a place that's sort of like the project memory, 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 matchmaking service for brands, not whatever some email platform. Right. Like it's kind of like 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 like 12 points on like how to save tokens but like asking it to be less wordy, more concise. Right? Like asking it to sort of like check its work visuals. I mean this is where I feel like there's a big divide in design right now. I mean you'll have to pry Figma from my cold blood hands. It might happen eventually, but I just love working visually. I'm a show versus tell person and that's even the way I lead teams. I'll sketch out an idea I have instead of just using words. And so when something is just off in Claude, I could back and forth with it in words for like 10 minutes or I could go to Figma and sketch it out in five minutes and it's probably going to be closer to the pixel perfect version I have in my head. And so I will very often kind of like dual task between AI building and Figma tools at the same time. You know, like it'll build something and I'll be like ooh, like that spacing is like a little bit off and I might guess move it up six pixels. Or I might like if it's something bigger than that, I might literally just design that little component or a part of a component and be like no this is how I want the avatar to look next to the name of the brand and the 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 such a helpful kind of stop gap, 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 purpleness of AI, but I do think that you have a lot of non designers right now. They're 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, look very similar, and that's because they're literally all being trained on the same 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 and what it's for, I feel like that is a conversation and some definition you should have as early as possible to start to infuse some of that soul and some of that, like, kind of, like brand and point of view into the product.
- [43:23]
Interviewer
That's been my experience too, where if you have the nugget of what you want, the visual language nailed down in the beginning, Cloud's really good at extrapolating it and like, yeah, maybe sometimes it'll go a little too far and you're like, okay, no, no, no, I don't want that, but. 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 it over here, you know, and it almost helps me scale my own thinking. And. And I was kind of chuckling with you talking about the canvas tools too, because same thing 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, and now I'm definitely settling into the middle ground where I feel like a lot of the strategy and skill around being a designer today is knowing when 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 left field hypotheticals that I want to toss your way just to make sure that we've covered everything. And the first goes back to more like team building stuff. And I kind of want you to imagine that you are maybe it's even in your current role. Like you get to build a new 0to1design.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, think about team building, role definition or maybe even like the types of skills or traits that you want to prioritize on that new org?
- [44:57]
Ron Golden
I really do believe that now because every function has access to the same tools, everyone could build something that looks like a product. I think still the things that we can do better than AI for now is one our bread and butter as 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 look, what is the experience that 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 know, you can't just be execution, you can't just be caretakers. Not that I think designers ever should be but like that is no longer valuable because a product manager can, doesn't need you anymore to do that. One, two, which we talked about as well a little bit. 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, every firm I've ever worked for, every company I've ever worked for has always been under source and 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 usertesting.com or whatever it and know what that looks like, know when it's useful and like just do it. Like I think that's, that's huge. The second one, you know, we talked about this a little bit is like that point of view, right? Like some people call it taste. I find that a little pretentious, but I will, I will call it brand voice, right? Brand positioning. Like how do you differentiate a sea of tools that are already coming out, they look exactly identical because they're all being generated by the same agents basically. Or could like how do you differentiate? Especially kind of 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 and to some extent visual design as well I think is very important. So there's moments of delight. This is something I really tried to do with Matchmaker. You built products. I know you can feel the sympathy when you're building products. I have found myself much more forgiving of visual design because I'm like, it just has to work. It's been so hard to just get to work. Well, I'm not going to worry about every little pixel. Right, right. But actually like once I get it to work, I really do find well, you know what like there what's stopping a competitor from like literally VOD coding the same exact thing tomorrow.
- [47:25]
Interviewer
Yeah.
- [47:25]
Ron Golden
It'll take them a day or two. Right. It's not that. So like finding the customers number one, like real growth stuff and then two, like having a really differentiating product. Right. That feels more premium, has an emotional connection with its users. Like those are things that fall squarely in the design world. So I think those are two skills, 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 are not afraid to look at a terminal and be like what in God is this? You know and like be and I even say like read. Reading the output of quad code 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 compute. Computer science.
- [48:16]
Interviewer
Yeah.
- [48:16]
Ron Golden
Or people that people have been designers that have coded a little bit or have been design engineers. I, I think that those skills, even though technically, yeah, AI does it all for us. I think those skills are really helpful because I have certainly found myself where I'm like, okay, lovable. I know what you're doing. Like you're stuck in like a for loop or something. Like 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 as like a minor in CS back in the day that like I can't explain how my brain has somehow like applied it to this world, but it still does. And so you know, I would say like my dream design team right now is. And again I think this is why hiring is so hard. It's like we are asking a lot of people, but it's like that T shaped generalist that maybe has a few of those areas now as a leader I've always believed T shaped means that is your responsibility as a leader at a company 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 checking off every box on my hiring list, right. Depending on the role I might have a certain non negotiable like consumer mobile if that's like a big part of my world, right. Like if you've just done like, like Enterprise SaaS, your whole career may be a little trickier depending but you know, if someone's never done research before, I will train you or I'll connect you with a researcher and like pair you up and like get you moments to safely start to feel comfortable in those moments, right. If you're not, you know, as much of a product thinker, visual designer, like this gets a little harder. Like you know, this I think just kind of comes through. Visual design to some extent I think is maybe education or self education and then product thinking honestly I just think is experience to a lot of extent.
- [50:06]
Interviewer
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 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 like technical, they want you to adopt the builder mindset but be the person that can really push what the visual identity of this product is forward. And I think my, my understanding is that it is coming from this need to elevate beyond the baseline because everybody's getting to the baseline really, really, really quickly right now.
- [50:46]
Ron Golden
And I think specifically all that. 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 you know, in a world where a lot of product design is very similar and flat for practical reasons like how many times can you design a long feed with A carousel, cards. Right. Like, there's 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 as we all know, it can be so bad when it's bad and
- [51:22]
Interviewer
so good when it's good.
- [51:24]
Ron Golden
Right. Like, I mean, you know, one of my. I have a very close colleague that is, you know, real, like, legit motion designer, and he's just like, less is more, obviously. Like, he's like, be very subtle, you know, like nothing worse than like a dancing hot dog type of moment on your. On your ui. So I think that is. 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 like that
- [51:45]
Interviewer
is just not do today.
- [51:46]
Ron Golden
And so, like, again, being able to creative direct art, direct create artifacts in, you know, After Effects rive, whatever it is, to sort of like, show and tell or to create those, like, Lottie animations. Like, that skill set, I think is part of the visual set is something that I find very hard to find. And so if you are that person and have everything else we described, just know you are in the top 1% right now.
- [52:08]
Interviewer
I've totally seen that too. Like, the portfolios that resonate the most have a little bit of motion. Like, if you really want to separate, if you can make your stuff move or just bring in one really seamless transition or even just the way that you think about the compositions of your work, if those move, like, even that is a big plus One AI is obviously pushing a lot of this forward, but some of it too is just new tools or lowering the floor, like, so much. Right. Like, I. I was always so intimidated by Lottie. I used to mess around with it with After Effects. That's a hard pipeline, man, to create something in After Effects and then get it to work with Lottie. That sucked.
- [52:41]
Ron Golden
Yeah.
- [52:42]
Interviewer
All of a sudden now I've been using jitter. It's like, oh, this is really easy. I can do this in 10 minutes and it's quite awesome.
- [52:48]
Rid
Or another thing that is kind of
- [52:50]
Interviewer
been blowing my mind recently is given
- [52:52]
Rid
an SVG quad's pretty freaking good at
- [52:54]
Interviewer
just animating the SVG beyond what I thought was possible. Like the ceiling for how SVG animations is higher than I thought it was, and I just didn't have the skills in order to do it. And all of a sudden I'm like, totally Kind of back to your black box analogy from the prototyping, the just checkout experience from like, I have no concept of this, if this is possible. I'm like, is this possible? Can you even do something like this? I'm like, can you just try it and then it tries it. I'm like, oh my God. Okay, cool. What if we did xyz, you know?
- [53:21]
Ron Golden
Totally. And, and the flip side, by the way, on the motion side, is that every single place I've ever worked, the engineering skill set tends to be weaker on the motion stuff. First of all, we're all very lucky to find a firm den engineer that loves design and can do pixel level work. But even those engineers at top fang level companies I've worked at, many of them are just like, I don't know how to work with motion and have it be performant. So again, maybe an opportunity for a design engineer type to fill that gap potentially and really master motion and code together.
- [53:55]
Interviewer
Well, it's a fun time to be a designer and everything about this conversation, I think, just points to that. It's been a real joy to hear about your journey and then all the little experiments and things that you're building now and just how you're thinking about the different roles and landscape, wealth of knowledge and experience. I really appreciate you coming on and sharing with us today, Ron.
- [54:14]
Ron Golden
Oh, such a joy and such a, such a great hang to spend time with you for sure, man.