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Podcast Episode Summary: The Changelog - Chasing that next BIG thing (Interview with Drew Wilson)
Episode Details
- Podcast Title: The Changelog
- Episode Title: Chasing that next BIG thing (Interview)
- Hosts: Adam Stachowiak
- Guest: Drew Wilson
- Main Topics: Drew Wilson's journey in software development, design, entrepreneurship, and his current work at Clerk and Cortical Labs.
Overview In this episode, Adam Stachowiak interviews Drew Wilson, a multifaceted designer and entrepreneur, who reflects on his extensive career in software development and design. The conversation covers Drew’s journey from creating Plasso to becoming the Head of Design at Clerk, his venture in starting a bank called Letter, and his current role in building a groundbreaking biological computer at Cortical Labs.
Key Conversations
Background and Career Journey
- Drew has been in the tech industry for over 20 years, starting with web development and design in the mid-90s.
- He built Plasso, an e-commerce platform, which was acquired by GoDaddy, marking a significant milestone in his career.
- Drew shares insights into his unsuccessful venture with Letter, a bank he founded, discussing the difficulties of the heavily regulated banking industry.
Reflections on Entrepreneurship
- Drew emphasizes the challenges of entrepreneurship, including the risks and the emotional rollercoaster of running a startup.
- He discusses how he invested his profits from Plasso into Letter, which ultimately did not succeed, leading to significant personal financial loss.
- The importance of having a cash flow in business is highlighted, contrasting it with the allure of large windfalls from successful exits.
Current Projects
- Clerk: Drew is currently the Head of Design and leading the upcoming billing product at Clerk. He describes Clerk's mission to simplify authentication and billing processes for SaaS companies.
- Cortical Labs: Drew is involved in designing and developing the first commercially available biological computer, which aims to revolutionize how products are developed and tested in healthcare.
Upcoming Ventures
- Drew teases a new project called Opacity, a platform designed to help designers and developers build and maintain UI components seamlessly, combining the best parts of Figma and coding environments.
- The emphasis is on creating a visual design environment that directly translates to functioning code, with version control and easy exports.
Key Takeaways
- Resilience in Entrepreneurship: Drew’s story illustrates the highs and lows of starting and running a business, underscoring the importance of resilience and adaptability in the tech industry.
- Innovation in Software Development: The discussion on Clerk and Opacity highlights a trend toward simplifying complex processes in software development and making tools more accessible for designers and engineers.
- Future of Technology: Drew’s involvement with Cortical Labs points to a significant evolution in computing technology, particularly the potential of biological computers.
Final Thoughts Drew Wilson’s journey is marked by a blend of creativity, perseverance, and a commitment to innovation. His insights provide valuable lessons for current and aspiring entrepreneurs about navigating the challenges of the tech landscape and the ever-evolving nature of software development.
Sponsors
- Clerk: Simplifying user authentication and billing for SaaS applications.
- Cortical Labs: Pioneers of biological computing technology.
- Fly.io: A cloud service provider for developers.
- Depot: A tool for faster builds and CI/CD processes.
Conclusion This engaging conversation not only reminisces about Drew's past achievements but also looks forward to exciting innovations in the tech industry, making it a must-listen for anyone interested in software development and entrepreneurship.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:05What's up friends, welcome back. This is your favorite podcast, The Change Log Log. We feature the hackers, the leaders, and those innovating in the world of software. I'm Adam Stachowiak, Editor-in-Chief here at ChangeLog. And today, I'm talking to my good friend, Drew Wilson. Drew is a designer, an engineer, and really so much more. Drew is a true modern renaissance man. Drew and I have been friends for a very long time, but it's been a while since we talked. And today, you get the peek behind the scenes of this fun conversation. A while back, Drew started a company called Plaso. that got acquired by GoDaddy.
0:40He started a bank called Letter that ultimately did not work out. He shared that story and so much more. A massive thank you to our friends and our partners over at Fly.io. Yes, the public cloud bill for developers who ship that you. That's me. That's us. You can learn more at Fly.io. Okay, let's talk to Drew Wilson.
1:11Well, friends, I'm here with Terrence Lee talking about what's coming for the next generation of Heroku. They're calling this next gen FUR. Terrence, one of the biggest moves for FUR in this next generation of Heroku, it's being built on open standards and cloud native. What can you share about this journey? If you look at the last half a decade or so, like there's been a lot that's changed in the industry. A lot of the 12 factorisms that have been popularized and are well accepted even outside the Ruby community are things that are, I think, table stakes for building modern applications, right?
1:43And so being able to take all those things from kind of 10, 14 years ago, being able to revisit and be like, okay, we helped popularize a lot of these things. We now don't need to be our own island of this stuff. And it's just better to be part of the broader ecosystem. Like you said, since Heroku's existence, there's been people who've been trying to rebuild Heroku. I feel like there's a good Kelsey quote, where are we going to stop trying to rebuild Heroku? It's like people keep trying to build their own version of Heroku internally at their own company, let alone the public offerings out there.
2:12I feel like Heroku has been the gold standard. Yeah, I mean, I think it's the gold standard because there's a thing that Heroku's hit this piece of magic around developer experience, but giving you enough flexibility and power to do what you need to do. Okay, so part of Fur and this next generation of Heroku is adding support for.NET. What can you share about that? Why.NET and why now? I think if you look at.NET over the last decade, it's changed a lot. .NET is known for being this Windows-only platform. You have WinForms, use it to build Windows stuff, double IS. And it's moved well beyond that over the last decade.
2:51You can build.NET on Linux, on Mac. There's this whole cross-platform open source ecosystem, and it's become this juggernaut of an ecosystem around it. And we've gotten this asked to support.NET for a long time. It isn't a new ask. And regardless of our support of it, like people have been running.NET on Heroku in production today. There's been a mono build pack since the early days when you couldn't run.NET on Linux. And now with.NET Core, the fact that it's cross-platform, this.NET Core build pack that people are using to run their apps on Heroku. The kind of shift now is to take it from that to a first class citizen.
3:25And so what that means for Heroku is we have this languages team. We're now staffing someone to basically live, breathe and eat being a.NET person, right? someone from the community that we've plucked to be this person to provide that day zero support for the language and runtimes that you expect and like we have for all of our languages right to answer your support and and deal with all those things when you open support tickets on heroku and kind of all the documentation that you expect for having quality language support in the platform in addition to that one of the things that it means to be first class is that when we are building out new features and things is now one of the languages is part of this ecosystem that we're going to test and make sure runs smoothly, right?
4:06So you can get this kind of N10 experience. You can go to DevCenter. There's a.NET icon to find all the.NET documentation. Take your app, create a new Heroku app, run Git Push Heroku Main, and you're off to the races. So with the coming release of Fur and this next generation of Heroku, .NET is officially a first-class language on the platform, dedicated support, dedicated documentation, all the things. If you haven't yet, go to heroku.com slash changelogpodcast and get excited about what's to come for Heroku. Once again, heroku.com slash changelogpodcast.
5:13well drew wilson is back in the house has it's been a while since you've been here it has i want to say gosh i don't even do my math here let me go search quickly drew wilson I think maybe 15 years, 12 years. I don't know. Something like that. Okay. So we had you on Founders Talk a couple times. Founders Talk was a show that I did solo where I talked to founders, makers, builders, things like that. And it was Valio. Remember this name? Valio? Yeah. Valio Con, man. Part one and part two. For whatever reason. And it was, that was the name of the show was Drew Wilson slash value part one and value part two.
5:59Oh, wow. Maybe, maybe we're not, maybe we're talking pre-Value Con and we're talking back when I was making, making stuff under the name value, which would have been like 2009 or something. You know, I don't know. Value Con was mentioned. Okay. Your ad network yogurt. Oh, dang. So that's probably like 2011. 2011, man. Yeah, that's right. Exactly. 2011 pegged it. September 2011. Wow. Okay. So that was that show. That was Founders Talk. I think we had you on this show to some point. Yeah, I've been on here before. But I don't know when. It was a while ago. It was a couple of years after that one for sure.
6:39So maybe 2014 or 2013, something like that. Well, listen, I should have did my better research on when Drew was last on this podcast. It was ages ago. It was basically the beginning. it was basically the earliest of days and it's been a lifetime i think i literally haven't talked to you in a decade it's been a while man at least a decade i would say i think maybe one or two tweets or something like that yeah here and there you know nothing nothing special you got busy though yeah you've always been the busiest person i know of but you got really busy yeah yeah like you built a company and sold it busy yeah yeah that was feel it was dude it was incredible um it's like one of those i mean it's not to the scale of you know you're a billionaire now you never have to work again but it was one of those like you come up with an idea you build it yourself you're able to build a little company around it you raise some money you know you do the whole investor thing and then you sell it and you make money.
7:47And that's kind of like the dream, right? It's not necessarily like noteworthy scale size dream, but it has the blueprint. Noteworthy scale size. Well, I think you may say that because you've always been a big dreamer and it's easy to some degree when you're in that position to downplay your accomplishment. Would you agree with that? I think so. Yeah. I think the way I see success is different than the way maybe my extended family sees success. And that's kind of like how I can gauge regular people versus people in tech. You know, the things you're used to in regular people land in terms of success is, you know, way smaller than what folks in tech are used to.
8:39I don't even think you were a dad. when was your kid born what year my first was 2010 so i my i have three kids so 2010 2012 and 2013 yeah okay so you were a dad barely yeah you were barely did you hide it i had i had was it a secret birth no no no uh we've just never joke honestly yeah we've just never wanted to like put our kids on social media. So up until recently, I think I had some tweets like earlier this year or no, I guess later last year about like, hey, I want to like start recording videos for fun of my personal life and doing stuff. And so I did some, but then I just got too busy to keep doing it.
9:29But yeah, it's always been like a conscious thing to like not post about our family or our kids or anything like that. So we're weirdos. So you have a famous or an infamous Apple computer behind you. What is that computer? Yes. So this is the Macintosh portable. It's got a trackpad and a little click button, and it fully, fully, fully works. Wow. I got that thing on eBay. You can boot it up. It came with a – it's a 16-pound laptop, okay? So this is the first ever laptop, and look at that. They look almost identical to the way they do today. So they got it right on their first try. Look at that.
10:08Yeah. It's 16 pounds, okay? And it had a lead acid battery in it, a car battery, for reals. And so that sort of tech doesn't even last to today. No matter what you do, that sort of tech will break down. And so you can't actually have a working battery in one of these. It's impossible. And so this one, the modification that was made on it was putting in a lithium ion battery in a 3D printing case to make it the same size. So that's what this has, and that's why it can work. And even then, the little pieces of metal that conduct electricity, and I'm forgetting the name, they don't work so well. So you kind of always got to leave it plugged in, running just off battery, even though it's fully charged, will only last like a minute or two.
10:57But you don't want to be carrying that thing around. It's way too heavy. Does that run Figma or the web or what does it run? Anything? It does. It does. It actually even has Wi-Fi. What? That was like one of the first computers with Wi-Fi. Oh, my gosh. What spec? Yeah. Wi-Fi 1.0, I think. Right. The earliest of Wi-Fis? Yeah. It's wild. It doesn't – I don't know if it can connect to my Wi-Fi. Did I try it? I can't remember if I tried it. But I got it at some point. I have this one. I have like an old Apple II and I have like the old, like the square tall Macintosh. Yeah, it's fun. I like collecting older.
11:41Yeah. Off camera, I have an Apple II, I think it is, or what, a Mac Classic. Yeah. I think it's an Apple II, if I recall correctly. It's just a prop. It's just for, you know, I call it art. You know, it's just art. Yeah. It doesn't work. Apple II is the flat piece with no monitor. and then you had to get an individual monitor the classic is the one that's in like the tall yeah okay so it's a classic not not a two i'm looking at the front of it just says macintosh classic on it yeah but there's a little floppy drive on there and whatnot yeah stuff i got a keyboard and a mouse but i don't even keep those things it's just there over there just being art basically just just looking like trash basically as a matter of fact not that we should go on this rant much further on the left and i'm pointing over here off camera on the left is the macintosh classic on the right is the 2013 what do you think it is the trash can oh wow the trash can right next to it yeah it's kind of funny because you see the this i suppose maybe the the under current to this conversation could be iteration right is this iteration of monitor compute cute floppy keyboard or external devices same idea pretty much except for the monitor with the 2013 macintosh trash can which was the mac pro it's like the same size basically it's basically the same size yeah yeah and just a very different form factor very different yeah it's it's wild too like the um this laptop is huge but if you take the little back portion out of consideration because that's where a lot of the larger um motherboard and everything is and the battery mainly um and you just collapse that down and you just take the clamshell piece it's essentially the same size as a modern day laptop um it's a little bit thicker but it's not like insanely thicker.
13:48Yeah. So it's wild how. I heard recently that it was Steve Jobs that actually coined the term laptop. Do you know about that? I don't know, but I do know that that term came after this because this is called a portable Macintosh portable. They even have a commercial. If you can look it up on YouTube, you can find the Macintosh portable commercial and they've got like this guy I had a business suit, 1980s looking, and he's got this massive case, which I have the case that came with it, carrying it around. I'm like, yeah, right. No one's ever going to do that. And they didn't. That's why these things didn't sell well.
14:26And they didn't. Oh, man. I missed you, Drew. I missed you, man. You know what you have is this unusual take, I suppose, on technology, like you just said there and no one's ever going to do that and they never did you know like you have this sort of like uncanny instant intuition of like what will and what will not persevere through the tech space and maybe i'm pushing that boundary a little too far but that's my perception you got a pretty pretty good intuition what'd you say i'm trying to be all hot takey i'm saying crypto won't oh yes crypto won't you don't are you against crypto i'm not against crypto i'm just against the idea that crypto is the savior of the world uh which i think is now falling out of mainstream think which is cool because i mean the technology existed before it's called smtp it's called email distributed servers serving up the same set of data and now you know it's just on a different protocol.
15:35And it was never used for any, SMTP was never used for anything beyond email and crypto will never be used for anything beyond collectibles and scams. That's where, that's where it fits. And this idea, I always thought it was weird, this idea of like a distributed database being such a big deal. I'm like, why is it such a big deal? Like every company you look at that has done anything great owns the technology and it's all centralized. No one wants to go to a distributed bank. I'm sorry, but they don't. No one wants to go to a distributed almost anything. They want the centralized version. They want the company that's there who's incentivized to make money and who will build up a scale of employees to service you, the customer.
16:18That's what they want. They don't want a distributed do-it-yourself sort of thing. I mean, there are people that do, but it's like less than a fraction of a percent. What are some hard beliefs that you would say you have? crypto will will be great for collectibles and hopefully also another spot like through bitcoin you know the name brand crypto will be another spot for super wealthy people to move money and so that way they don't have to move it into real estate and harm the real estate uh industry in that in that by doing so by buying up a bunch of properties it makes property go up everywhere property values go up everywhere it makes it harder for regular people to buy homes at an an affordable price.
17:04That's one. If we're staying on the crypto train, if we're not staying on the crypto train, another hard belief. Let's say maybe a hard observation. How about that? I still think it's interesting that design and engineering are now a regular job. I was always the young guy in tech. And so that will never kind of go away from me. But this idea of getting into tech and it being a job and not like a hobby and something that you want to do is still so strange to me, especially when you get into running companies and having employees or having teams. And, you know, you start to realize that, okay, this person does one thing and they're probably only ever going to do one thing.
17:54And maybe they have aspirations of being really good at this one thing, but they don't really want to spread out and like think of tech as this, think of tech as one thing. And there's many aspects to it. They think of I'm a designer or I'm an engineer or I'm a product manager. And so that's the segue into my hard belief. Here comes my hard belief. That was all getting my mind ready. But here's the, here's the, that was my hard observation to now my hard belief. Okay. I'm down. Take me there. I don't know how to phrase this. So I'm I'm just going to think of how I could phrase it. It's something that I've always thought about, but I've never had to put it into a concise set of words.
18:32So I think product managers who are not really good at sales or really good at engineering or really good at design are useless in tech. It is so disheartening to be on a team where there's a product manager. And that has nothing to do with them personally. It's just it brings the capabilities of the team so far down. When you have a product manager who's never been an engineer, never been a designer, never been good at sales, what the crap are you good at? Why are you at a tech company? What are you doing here running this? What are you doing running this department? You have nothing to contribute except ideas.
19:15But guess what? Everyone here has got ideas, and they're vastly more informed than your ideas. So what the crap are you doing here? and why are CEOs allowing this to take place? Oh my gosh. Like if you're going to be with someone in product, you should know product. And that doesn't mean I have a good idea and a good intuition on what users want. If you do have a good intuition on what users want, you should be super good at sales and you should have some experience there. And you can bring that to the table because for the most part, we're all building something that at some point has to be sold.
19:48But if you're not that, you're not an engineer, you can't like understand how to build something and you're not a designer and you can't understand how to build something in that aspect like what are you doing here so there's a lot of i mean i would say most product managers fit that mold of not being able to do any of those three and i think that's why you see these large layoffs and product people are usually the first to go is because they don't really have any skills to contribute other than organization and if you're not even that good at organization, which a lot of them aren't. That's why some people come over, they take over a team, they're like, what the crap?
20:24Where's all the documentation on what you guys are doing or where you're going or how this works or that? Well, no one ever made it. So what was the purpose as this product manager besides receiving a paycheck for doing almost nothing? Okay. There's my hard belief. The way you're describing this makes me feel as if you've been, you know, bitten twice. let's just say. Have you been bitten twice by this product manager who has no skills bug? I haven't really been bitten in that I haven't been on a team where I had to be beholden to somebody like that. It's just that I've been in companies that have that.
21:04So when I sold my last, not my last startup, one of my last startups to GoDaddy, I was a part of which is a great organization um great people but they are a 10 000 plus person company they're a public company they have a lot of these product managers that they don't have any skills beyond just thinking they have skills that's their skill is they think they have skills um and they're able to convince themselves and an employer that they do uh and so you look at what these other teams are doing you're like my gosh you're just running in circles You're never going to launch it. The blah, blah, blah.
21:40I came into GoDaddy as an acquisition. And we moved our tech, Plaso, which was a payments platform into GoDaddy. And it became their payments platform. It became the way that folks transact using GoDaddy's websites. And when I did that, we integrated in six months. And I won the Getting Shit Done Award at GoDaddy. They have an award that they give out, which is really cool. And it was because I did it in six months and we've never had an acquisition happen in less than three years or something. And I'm like, good night. And then I found out why. Product leads that company. Every product person there is essentially the mini CEO of whatever they're working on.
22:25And that is the standard tech model. And that is how most tech companies work. and the problem with that is if you have product people that really don't have any idea how to build a product uh you're gonna turn turn out crap yeah i think you see that happen so you say also other other companies that i've been a part of that suffer from the same things it's not just them
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23:41and then you're left to your own devices to essentially configure that VM and configure your build pipeline, effectively pushing down to you, the developer, the responsibility of optimizing and making those builds fast, making them fast, making them secure, making them cost effective, like all pushed down to you. The problem with modern day CI providers is there's still a set of features, a set of capabilities that a CI provider could give a developer that makes their builds more performant out of the box, makes their builds more cost effective out of the box and more secure out of the box. I think a lot of folks adopt GitHub Actions for its ease of implementation and being close to where their source code already lives inside of GitHub.
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25:10so we we have some history and i'm happy to keep talking as if it's just you and i and that's cool with me but it is not just you and i here drew there are people listening do you know that right oh this is a podcast yeah that's a podcast man okay uh just because and i never asked anybody to do this, but just because I haven't taught you in 10 years, you haven't been on the podcast in a decade. We have some history. I know who you are, but just give a slight primer, like maybe a two minute TLDR on Drew Wilson. Hey, all right. So I'm pretty early to computers in the web, built my first website when I was 13 and 96, taught myself how to design on Photoshop too.
26:01And then never wanted to, but didn't know any engineers. So needed to learn how to code in order to build the things I was designing. So I taught myself how to do PHP in 2000 and built my first like backend code and database back then. And then loved it. And so I've always been a designer and engineer working on the web. I was early on the iOS and Mac app stores, built apps for Apple natively, not at Apple, just as an individual. Had like a number one best selling Mac app. It was called Screeny and it did screen recording before you could do that on an Apple device using QuickTime. Built these icons called Pictos, which tons of people still use.
26:44It's still the default icon as the shopping icon in Shopify. That went off like hotcakes and then built a couple different e-commerce platforms, one of which was called Plaso. And like I said, sold that to GoDaddy in 2018. Also have a conference that are run called ValueCon, valuecon.com. Ran that for six years, bringing it back again this year, later in September. It's been seven years since we've done one, but that was always fun. Conference for designers and engineers. And then after Plaso, I wanted to take on something that I thought would be a really tough challenge and it really was. And that was a bank.
27:27So, I started a bank and ran a bank for four years called Letter, Letter.co. Got into YC with that one, raised money, did the whole thing, partnered with a billionaire, lent out millions of dollars to folks. It was great. It was fun, learned a lot. Ultimately, couldn't make it work. So, I had to shut that thing down. and then ended up at AngelList for a little bit and then left there and jumped over to Clerc, Clerc.com, which is where I'm at now, running the upcoming commerce and billing product that we'll be launching and then also working on some stuff on the side too. A lot to cover in there.
28:10What I've always appreciated about your history was that you were driven, of course, but self-driven and self-taught, learning to design, designing things, and then getting frustrated not having people around to, or not wanting to have people around to build the things that you're designing. And then be like, I'm going to, I'm going to figure out this PHP stuff. You just figure it out. Next thing you know, you're building stuff, you're building iOS stuff. And you've always had this, it was, It's almost as if you've got this Drew Wilson style sort of stuck in there. And whatever comes out, it just oozes this certain feel.
28:51Even when I go to valuecon.com right now, this feels like a Drew Wilson design. This doesn't feel like the lettering is cool. Did you do this lettering? Mm-hmm. Yeah. That's your lettering. I mean, everything is like, how do you just do everything, Drew? How are you a renaissance person? Well, you know, you just, I don't know. It's many, many years, you know. It's like the overnight success. Well, it was actually like 7 ,000 years in the making. That's my case, right? I've been literally working in Photoshop since 1994. I don't know, somehow that, right? Before there was layers. Before there was layers.
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29:33Oh, before there was layers? Oh, my gosh. Can you imagine that? No, I cannot imagine that because I don't think I've ever worked in Photoshop before layers. So I've only ever known layers, Drew. Yeah. So it's just like a bunch of years. Like, for example, I wanted to start a bank. And I didn't know anything about banking. I didn't know anything about finance. At that point, I think I had just started investing in stocks. I didn't really – can you imagine that? In 2018, I was barely aware of stocks. So I started a bank and I was like, well, I guess I'm going to be a banker. And I was like, I guess I need to go for these – like there's these accreditation tests and these different certificates you can get.
30:23So I started studying for that, thinking I needed this. But it turns out, oh, just one person on my team needs to have that. My CFO already had that. So I was like, okay, I don't have to go take this test. My co-founder and I were all set to go down and take this test that we just crammed for in a week. Normally, people spend months on this thing. We just went through it crazy. We're going to go take the test. But when was this? This was right around COVID. And so the government testing facility was shut down because of COVID. We're not going to open for months. I'm like, oh, crap. And that's when I found out I actually don't have to have this certificate.
31:03But anyways, so then I learned a ton about banking in general. I just went on LinkedIn when I knew I wanted to start this company. And I hit up all the banking CEOs in the San Diego area. And one of them got back to me about like, hey, can we get lunch? You don't know who I am, but why don't you just get lunch with a stranger? And he's like, sure. So we went and had lunch for like two hours and chatted about all things. And I learned a ton about banking through him. And then we just went around to different banks around the country and tried to find a partner. We ended up finding one through a banking platform, went through like three different banking platforms, helped a new banking platform.
31:43It's called unit.co. We were like their first big customer, built a lot of security stuff ourself because they didn't have any at the time. They modeled after what we did. And yeah, like now I know a ton about banking in case that's ever useful and about finance. And so that's how it happens. You know, you just go on these tangents here, there, and the other. I'm not sure that's how it happens, Drew. I'm really just not sure that. I'm not sure that's how it happens. Okay. Let me give, let me clue you into something that's a truth that I believe is a truth. I think these things happen to you. I don't think these things happen to other people generally.
32:23Can they? Yes. Is it possible? Yes. I'm not denying that. But I think only someone like you, and what I know of you at least, is to say, you know what? I've got an idea for wealth management, for high net net worth owners, you know, folks out there. And I got this idea for a bank for them. And I'm just going to start designing screens and flows and whatever it is. That only happens to you, Drew. And only to you do you have to learn banking, having never even touched or knew much about stocks in 2018, to then create letter. Even if it defunct, I'm really curious about this. What did you learn? Have to what did you have to learn about banking to make letter possible?
33:06Like, where did you begin? It blows, dude. It sucks. Banking sucks big time. FinTech sucks big time. FinTech seems like this place that would be an absolute gold mine. Right. But it just isn't. It just absolutely is not. The way the banking is set up is that in the US and in most places, it's a government regulated business type. And the reason they regulate it and banking super heavily is because they cannot afford to have banks go under. You can't just fail. Like a startup can just fail and no one gives a crap. Maybe some investor who overextended themselves on your round will care, but nobody else will care.
33:52A bank can't fail and it costs a lot of money to a lot of different entities if a bank fails. And so they highly regulate what you can do, what products you can offer, what prices you can offer them at, what sorts of verticals you can go into so that you will not fail. As a bank, you can't just be like, oh, wouldn't it be cool if we could offer this sort of loan and just offer it? No, you have to get approval for that kind of stuff. Really? Yeah. How do you get approval for like, give me an idea for a loan. You may have had this idea for a loan. Did you have this idea? Was this your thing or? Yeah, a new type of lending product, which would originate loans, right?
34:33Right. To do a new type of lending product, if you're a federally chartered bank, meaning you can operate in any state in the U.S., the OCC is going to be your regulator and you have to go through them. Now, this is if you're a bank. To get to be a bank is a huge deal. The U.S. stopped issuing bank licenses from the year 2007 to the year 2017 because of the banking crisis. And a bunch of the little banks got bought up by larger banks. Just to give you an idea, like your average mom and pop bank, which barely exists anymore. I mean, they're technically considered, financially considered a small business.
35:11They're making like a million dollars a year. It's nothing big. Yet you would think, oh, it's a bank. They're making tons of money. No, they're not. If they're one of the big ones, they absolutely are. because with banking, you can't make big revenues because you're regulated against this idea of loan sharking or charging too much money. You literally cannot make a lot of money in banking unless you have an enormous amount of customers. That's just how it works. What's enormous? And it will never change. Millions and millions of customers. We're talking like Chase size, Wells Fargo size, or some of the new startups that have gotten there.
35:54who can now become profitable. So like, what's the one with the gold card? Like Robin Hood's getting into banking. And what's the other R1? Revolut. Even Monzo, who was doing really well in the UK because they hand out banking licenses called these e-bank licenses really easily, was doing really good over there. Couldn't make it in the US. The regulations are just too stiff. And you got to have way more money than what they have. So banking is a very difficult – I mean, even Silicon Valley Bank failed, right? Banking is a difficult industry to be in, especially the one I jumped in. I jumped in thinking like, wow, there's nothing new and modern for high net worth individuals.
36:40Let's do something there. Well, it turns out if you want to get into that space, you have to go through money managers, wealth managers. because the wealthy people don't give a crap about who's managing or about where their money is. They just want their manager to deal with it. They're like, yeah, you deal with it. You deal with it. You figure out what's best. I don't really care. And so it's very difficult to do a B2C play in that arena. Yeah, definitely challenging. So what made you – where were you at, I suppose, in your life to make letter even an idea? Not even possible, but an idea. Yeah.
37:20So what happened to me was I had sold my company, Plazo, to GoDaddy. And it was like literally a dream scenario, like an all-cash deal with the option to jump on as an employee and get like a good paycheck and additional payouts if I stay on, right? So I stayed on there for like two years. But with that initial cash sale, I paid back my investors plus some because they made money on the transaction. And then paid some of my employees that had equity. I made sure everyone who worked with me had equity. So folks made money. And then I had money. And I had never had money before. As a matter of fact, in order to get PLASO to where it was, I had to take out a bunch of loans on the same day so they would not know about each other and they wouldn't show up on the FICO score thing, the credit report.
38:20So I took out a bunch of loans the same day just to keep the company going. I was making it up for myself, but that's it. And I needed these other employees to help sell the thing. And so I took on massive debt, like the amount of debt that would take me my entire lifetime to get out of if things didn't work out. And so, yeah, I took on that debt. But then just as I had to fire my last employee being like, sorry, I don't have any money. That literally that was on a Friday that was their last day. I came into the office on a Monday and there's an email in my inbox from GoDaddy saying, hey, we'd love to talk about partnering.
38:58and you know acquisitions always happen under the guise of partnerships i didn't know that um and then three months later i had sold my company a little over three months but it was like it to me it was like 10 years of my life it was just like so exciting and at the same time so like it's like a roller coaster of emotions because things are going your way not going your way is it going to happen it's not going to happen it's going to happen oh man and i didn't have anybody else it was just me i was the only person doing negotiations there was no advice giver on my end. No lawyers, nothing. It was just me doing it all.
39:34And so it was a great experience. It was a great experience. The company acquisition team at Good Eddie is super nice. So it was cool. Got through it all, made some money. Then I was like, well, I've never had money before. What the crap do I do with money? And I'm like, there's got to be a site somewhere before. I was like, there's got to be a site that says like what to do. I'm like, look around. I'm like, oh, there's no site. The closest you'll get is like the points guy kind of stuff. But that's like a totally different scale. And so I'm like, what the heck do I do? I have no idea. I'm like, I'm sure other people are in this situation.
40:09Maybe I should build an app for them, like to help them manage their money and have this like, you know, advisor here with you all the time that you don't have to interact with personally because no one wants to pick up the phone and call someone. So that was kind of the idea behind Letter. And that's how I arrived at that idea. And I was like, I should make a bank. No one's making banks. I could make a bank. I can make a bank. There's just a bunch of old people making banks. Is this literally right after the acquisition timeframe? Like the three months are over, the acquisition goes through, all cash, you're an employee, then letter?
40:46Or is it like a year down the line? Like, I don't understand that compressed time. It's all at the same time. So I could be very optimistic. As an example, when I was going through the transaction, this was not a done deal. But in my mind, I'm like, I could see this totally being a done deal. And we're still like a month and a half out of what would be the end date. The thing is, you don't start a process, like an acquisition process, knowing when the end date is going to be. And you don't really, it's not till you're like a week or so out that you know, like, okay, this is when it's happening.
41:22So this whole time, it's just like, could go either way. But I'm like, yeah, it's going to go my way. And so I'm looking at this house that I live in now. And I'm like, I have no money, right? I have no money. And my wife and I are going around, we're looking at homes like, yeah, let's take this one. This one's like a very expensive house. And they're like, okay, cool. If you want this house, you know, put in the application or whatever. So I put it in and they're like, we need a good faith deposit. It's typical in America to put down a little bit of money. And the deposit they wanted, like I just flat out didn't have.
41:59So I'm like, so I'm like, they wanted like, basically like, I don't remember. It was like 20 or$40 ,000. And I'm like, will you take a thousand?
42:12i'm like i promise i have the money to buy this house and i have to show them financial statements and it shows no money and i'm like i promise i promise it's there i have no idea why they just like we're like okay sure okay sure but they took the thousand bucks and they took that and i was able to get the house and it came down to the point where okay now you got to pay for the house and like, I just need like another week. And they're like, okay. And that week's coming. And I emailed them like, I know I said another week, but I'm going to need like one more week. And they're like, and they're like, okay, fine.
42:52And then that week happens. And literally like a day or two before I needed the money, I got the money myself and was able to give it to them. But so that's how optimistic I can be. So when I'm trying to remember your original question, but when the, I think it was around, yeah, letter when I started. So that kind of shows you my mindset. So I got the house. I'm an employee of the company now. I'm working at GoDaddy. I think it was probably six months or so before I came up with the idea for the letter. And I wanted to just chill out and not like work on anything other than this one thing I was doing.
43:32And so I got through that initial launch. It took me like six months to get the product out the door at GoDaddy. We got that out. And I think it was right around then when I was like talking to another buddy of mine who worked at GoDaddy that I had met there who had sold his company to GoDaddy the year before me. And yeah, I was just thinking more about finance about what I should do with the money. And there was really nowhere to turn. And I didn't want some 20-year-old kid working at Wells Fargo deciding what to do with my money who's never had money himself. No. So, I had a financial advisor who was my CFO, who ended up being my CFO at the bank.
44:11And even still, it's like, this is so manual. Everything's a phone call. Everything takes forever. It's like, it's got to be a faster way. So, that's how I came up with the idea for Letter. And what's funny is I started the company and let it end up – originally, we were going to be a bank – banking as a platform. So, like purely a code thing. And then we turned into this more like branded bank sort of thing. And I applied to YC. It took me four tries to get in. And that YC calls me and is like, hey, we think we want you in, but we're not sure. So, we're going to have another partner talk to you.
44:47Are you available in the next two minutes? Yes. they call me i pitch them and they're like okay okay okay i'm not sure and then like 10 minutes later we're gonna have you talk to another partner they're not sure talk to another there's four times four times i had to talk and finally they're like okay okay we'll let you in uh what was the pitch i don't want to i do want to hear this pitch if you can like maybe even earmark that i want to hear whatever the pitch was to these four people or some version of it to be honest i have no idea. It's been so long. I don't remember if I pitched them the banking as a platform or if it was at that point, the branded bank.
45:28I think it was the branded bank and the pitch was just like high net worth individual. Okay. So high net worth individuals are 2 % of the population. They make up 98%, 97 % of the dollars in the US. And all of these other startup banks are going after two or 3 % of the money. Whereas I'm saying, I'm going to go after this pot of like 90 plus percent of the money. Maybe it was 70%, 80%, 90%. I can't remember the numbers. It's been so long, but it's an enormous amount, vastly outnumbering everybody else on the planet. And I was like, there's a huge market here. No one's going after this. We're going to go after this and we're going to, you know, we're going to win because we're modern.
46:14We'll have an app. Literally, even now, other than later, that doesn't exist. There's a reason why is because like I said, that demographic just doesn't care. But yeah, so that was the, that was the pitch they bought into it and they're like, sweet, let's do this thing. So I got into YC. What's funny is I was in YC for three months while working at GoDaddy and I had a huge team at GoDaddy. It built up the payments team. I think we were at 16 people was my team at that time. And then plus other teams, you know, assisting us. And then I'm doing YC at the same time. And then demo day is going to come up and I've got to like schedule my GoDaddy meetings to have these gaps where I can do demo day and investor meetings.
46:59And like, I think it was like a day or two before demo day. My boss is like, hey, do you got a second? And I'm like, yeah, sure. He's like, oh, how's it going? He's like, I'm in a screen share. He's like, so I was going through this website and he has YC's website pulled up. I'm like, oh. And he's like, and I scrolled down and I saw this person. And it was a picture of me. It's a picture of me and the company. I saw this guy. And he's like, so what's going on? I'm like, yeah, I'm probably not going to stay for here forever. And so my plan was I was going to get NYC, raise money, finish up the last bits of stuff.
47:37I had to do a good adding. That's right. But he preempted that. And so then at that moment, I had to be like, yeah, I'm probably not going to stay. Sorry. Well, that was only a few months after the acquisition. Didn't you say you had a stand as an employee for a bit? No, yeah. So this was so I came up with the idea maybe six. Yeah, maybe six months or so after. and then there was a whole bunch of rigmarole about figuring out how to set up the bank what to do started the company ran the company i think for like a year before we jumped into yc um or something like that so yeah there there was about a year and a half in between in between that and then what was the company doing for like you know while you were preparing for yc like what was the company running the company so it was building the product um Um, like I said, at first we thought we were going to be a banking as a service kind of provider, but then ultimately decided we didn't want to do that.
48:36There's already a couple of the players in the space. It seemed horrible to do, and it is, and you'll talk to those companies. It's horrible. Um, and, uh, as a matter of fact, there was another banking as a service provider in YC, in my group, a guy named Dara Buckley. He was the second hire at Stripe. Um, super cool guy. We almost we're talking about merging our companies uh at one point um but uh he was doing that and um so yeah we decided not not to do that uh yeah so we were in the middle of building out this idea of a banking as a service provider and then we switched and we're like okay we're going to be the retail bank because what we were going to do is build banking as a service provider and then have our own pretend sort of active, sort of not retail bank to give people an idea of what you could build on our platform.
49:30And then we decided, let's just build that retail thing. That'll be way better. It's not really way better. Well, so hindsight on that, I mean, so letter didn't succeed long-term. I'm assuming, I don't know why it didn't succeed. Why did it not succeed? Why did it work? Ran out of money. Ran out of money. That's the practical reason. The We approached the market incorrectly and we didn't have the cash to correct, right? By the time we learned how to correct, and anyone who's in that industry, they know this stuff just takes forever. These feedback cycles take forever. So if we had landed our series A, we would have been good.
50:17So we raised a pre-seed and then I raised a seed round. And then I ended up spending all my money, way too much money on this bridge round, essentially. It wasn't really a bridge round. It was more just an open access to Drew's bank account to pay for the company to try to get to this A. So what we did is we had this investor who, a super cool guy, became a billionaire a couple of years before we started to the tune of like$4 billion. bucks and had a bunch of money, started buying up all this Western-themed stuff. And by Western, I mean like horses and cowboy stuff. So, he bought up Country Magazine, all the country stuff.
51:02He bought up all the American rodeos. He bought up all the cable programming for Western-themed stuff, was building a Western-themed movie studio because he's a former movie studio exec. and so somehow I got to be on a zoom with him and pitched him what we were doing and he was into it and wanted to invest mostly because he wanted to create a western themed bank under the brand name that he's buying all this other stuff under so we're like yes we'll do that we'll white label letter and we'll have this you know other thing for you too so that was the deal he was running it all himself. And then he brought in a team to run that brand that he had made because he didn't want to run it anymore.
51:52And the team he brought in was headed up by the former CEO of Hulu, the guy who sold Hulu to Disney. And so, then I was interfacing with him and his team. and their idea was to create an Apple TV Plus or a Disney Plus, but for Western-themed content. Well, it turns out they couldn't secure anything, literally anything. They couldn't secure anything. So he's like, hey, Drew, we don't know what we're going to do here at this brand, but we do know that it's not going to involve a bank if we can't figure out how to make money. so sorry we're no longer going to fund uh your bank and so this was me like trying to get this deal across the line for like seven or eight months uh and it was just like it was always right there just like we had paperwork sent to them they would revise send back and just like i'm like that's so close just sign the freaking paper but then then it never happened and that was early 2023 when they pulled out.
52:59That is the exact same. The same month they pulled out, it's the same month that Silicon Valley failed and everybody started pulling money out of there. And we felt that at our startup bank too. Folks weren't super comfortable with the startup bank anymore and moved their money around. So yeah, we got kind of hosed there. But we did get to use that guy's money to lend to people. And we create our own in-house lending platform where you get a loan in a few seconds. And it was a hundred percent programmatic, meaning there was no humans in the loop at all, which is crazy. And I don't know of any other thing or program that's done that, but we did that, which was fine.
53:40So that's why it didn't work. What in the world is involved in building this? I mean, I just look at you. So I don't want to downplay you. I don't want to say drew his just but just for the sake of just this conversation you're the person who taught yourself how to design in photoshop before there was layers and it's not saying that you can't learn but you're somebody who came from literally a zero in terms of like knowledge you didn't have the design skill you gained the design skill you didn't have the engineering skill because because you didn't really want it. You weren't interested in it.
54:16You gained that. And now here you are creating a freaking bank. Like, come on, Drew. People always get hung up on the bank thing. They think it's so impressive, but I don't know. It's just another business. It's just another business, huh? It's regulated. It's more regulated. It's just highly regulated. It's just unlike that. Let's say that's the reason why it's so remarkable is that it's so unlike, like, I don't know anybody who's created a bank besides you. You're the only person I know. And you're the only person I know that – what I think is actually strange now that I'm realizing my words that I'm putting out there is that you're the only person I know that created a bank and you're the person I thought would never create a bank.
55:01And then the same person. I don't understand that. Yeah, I don't think I ever had bank on my bingo card either. Yeah. Well, really the reason I wanted to do it is I'm like, no more making little apps. I'm done. I've done that to the nines. Right. Yeah. I just want to do something like big that could become a big company. Yeah. And so that was my big swing. Since then, I've come to realize that, you know, having a big win is such a – financially, it's so different than having a large cash flow. Having a big win means you can go out and buy a big house and do a bunch of cool stuff and get all this kind of crazy stuff going on and invest in these properties and do that.
55:47It's like it's what you would think of as wealth. That doesn't happen when you have a huge amount of cash flow. If you make$2 million a year, you literally can't do what I just said because you don't make enough money, even though you're making$2 million a year. It's just so different. But if you don't have cash flow, you can't do anything. You can't control your own destiny. You can't work for yourself. So having like a cash cow, like an app that's like just killing it, you know, on a small scale that lets you not have to work somewhere, that lets you get to experiment and do whatever you want.
56:26That is like the idea that is the successful life idea, right? That's not the successful finance idea. That's a successful life idea. And to be like the ultimate goal for a lot of people who are very ambitious is to have both of those. You have this windfall so you can do a bunch of cool stuff, but then you also have this cashflow. I gave away my cashflow when I sold my company. I was too inexperienced to know all this at the time. But I did get the windfall, which was great. But now I need the cash flow. And so, learning all these things that I've learned, there's always so much more to learn.
57:10And so, I got to get myself another cash cow and then I'll hopefully be, hopefully I'll consider myself set. But until then, I can't stop the doing of the things. um yeah i don't know where i'm going with that but there i said words you said words well i think okay so from plaso you had a windfall right you said it was an all cash deal you were able to take care of your investors plus so they were able to make their money back plus a percentage or an x well how do you want to frame that you paid the employees you paid early folks who had you know sweat invested into you with their loyalty and their abilities and their friendship and their whatever however you want to frame that then you obviously had your own money that was from that you took on it sound like some massive debt just to keep the company going i assume that cash you know took care of that debt no problem boom shabam but then you said in that story and tell me if this is the treacherous moment or if you're still okay, is you said that for a bit there to fund letter, it was an open, the bridge loan scenario, that letter had open access to, in your own words, Drew's bank account to make things go.
58:30Did you lose a bunch on letter or did you just, did you kind of come out even? Pure loss, pure loss. No, no, no. We made money in that there were people paying us money and money went to our bank account, but we were not profitable. So I lost a lot of money. More than. Like millions, thousands, hundreds of thousands. Millions of dollars. Millions of dollars. And this is your own cash. Yeah. For me, it was like the decisioning was like, well, if I stop Letter now, it's going to take me four years to get to the point with any other company where I'm at right now with Letter. So I may as well just keep funneling my cash into this thing and try to make it work since we've already gotten so far.
59:23And that was kind of the reasoning behind it. Had Letter worked out, everyone would have said that would have been the greatest decision you ever made. That's the best investment you ever made, Drew. But if it doesn't work out, you probably should have cut your losses earlier. You know? That's right. Yeah. How do you know in the moment? You don't, right? You don't, yeah. And so, sometimes you win, sometimes you lose. Actually, let me rephrase that. You always lose and then sometimes you win. Yeah. You're usually losing and then sometimes you win. And so, yeah, it makes the wins all the more sweeter when they happen.
1:00:00For sure. But at some point, you know, I'm noticing I'm 41 now and, you know, you just get sick of it. You just get sick of writing code. You just get so sick of having to design another freaking page. It's like, gosh, dang it. It's just, I'm so sick of it. Like I've designed every kind of page so many times. I've written every kind of code so many times. all the languages all the sdks all the from scratches all the things like i freaking built a a css interface to your database with fire rift back in 2009 oh my gosh like tailwind is the only thing close to that now just doing absolutely insane stuff with the class name stuff don't get me started there uh but you like that or is it a bad thing i don't want to offend anybody but no i don't like it.
1:00:54So, I don't know. Like, he just, you know, it just gets old. It gets really old. Like, all these people are 20 and I see them like, oh, just raise money through YC. I'm like, dang, you look like you're a baby. And I'm like, well, you know, it makes sense. You know, they're young and hungry. I still feel hungry, but I'm not young. And, you know, my big attempts, you know, overall turned out well, but they were never like big, big. So, I still am after my big, big one. You know, like I have these ideas. I'm like, gosh, dang it. There's someone out there making supersonic jets. Gosh, dang it. There's someone out there making robots.
1:01:36Why can't I freaking do that? I want to. but I feel in my mind that there's just this massive gap between what my ideas are and what I gravitate towards versus like what some of these guys are doing when they're making robots and stuff like my mind gravitates towards solving problems that are in front of me not towards you know problems that plague earth 100 years from now right and so I've come to the grips with the fact that it's probably how it's always going to be for me. And so my next thing I want to do is I want to build something that has an enormous cash flow, but is like we never take VC and it's just me and somebody else.
1:02:24And I think... I think I'll actually be like satisfied with that which will be cool because I've always wanted to be the person that builds the big company but I just never could figure out how to get there. yeah so i've always known you as a i would kind of classify as an inventor in a way not like a literal like you made something but you've definitely like picked us was not something and then you know creating uh icon libraries became a thing the way you engineered to deliver that initially i mean like you invented all these things to make something very simple that didn't have to be that simple i mean it could just simply you could give me some pngs or some svgs now or whatever like it could just be like thank you drew but no you went and made it you know api accessible or interactable and like all these different things we picked us over the years you're an inventor i would classify as that yeah and and i've always been disappointed in myself for not having the ability to to i could think larger i could think of things that i want to do that would be big, but I just don't have the ability to do it.
1:03:32And I've always, practically, it's broken down to the fact that I don't have the network to do that, right? And so part of me doing letter was like, ooh, especially like in YC or meeting these like IronNet with people, hopefully that will change things for me. And in some ways it has, but I just need to go even deeper there. Like that piece, those people that are creating those large companies are usually super well connected right um and that's kind of why that stuff happens practically that's why it happens that's why i like movies that get made you know you're always seeing the same people making these movies well it's because they have a network because like it's very hard to break in unless you unless you have that um so network is required you're right i mean you can't just have the the skills and the ability and the drive you have to have the other people yeah to offset like the cfo with the license for example you know so you don't have to go and do that yourself cram for a week you're your co-founder and go do that yeah if you know um the yeah one of my big stretches though in that uh i want to be a part of something very large is this thing called cortical labs i don't know if you've seen that but i just i just launched the new site there so i'm on the team there as well um doing design so it's cortical labs.com how do you spell that And C-O-R-T-I-C-A-L, cortical.
1:05:00Labs.com. And so what we've built is the very first commercially available biological computer. An actual human brain inside of a computer, and that is the CPU. That is the only, you know, CPU. So it's pretty rad. We could take a prick of your blood or sample your skin, regress that down to a stem cell, put it into the proper environment to then grow it into a neuron, put it on a chip. It'll expand and grow into multiple neurons. That chip that we have is specially designed by us. And on the bottom of it are a bunch of electrodes. So essentially, the neuron is growing on a floor that is made of electrodes.
1:05:48And then we have a bunch of connectors to that electrode. and you can program, you can write code and you can have the neurons do things for you, right? And you can receive signal back from them. And the thing that we've built is the thing that translates your code into electrical impulses to the neurons. Also, the computer, the CL1, has a bunch of hoses in it to feed the brain essentially electrolytes because brains make their own electricity through a chemical process where they break down electrolytes and sodium to convert that into electricity. So you can have this computer that virtually takes zero power, just the LCD screen that we have on there is the only power, and the pump, the little teeny pump that pumps the fluid in and out and cleans it.
1:06:42And so you can have a neuron growing in there for up to six months, or a set of neurons. So you can We have in the past, in 2021, they gave it the rules around Pong and the neurons taught themselves how to play Pong. So you could watch them playing Pong on a screen. The idea is that instead of artificial intelligence, it's actual intelligence. And where artificial intelligence is trying to get to, they're trying to get to AGI. So then you can prompt it and it can like think like a human. That thing starts at a human. It's already there and it already thinks like a human. And so it's a different approach.
1:07:22what we're building now is like an AWS server farm, you could think of it like. But instead of a bunch of computers and hard disks, it's a bunch of these CL1s stacked on top of each other. So you can access a brain computer through the cloud instead of having to have one. So you can either buy one and develop on it locally or you can develop through the cloud. Well, now I'm angry with you because you just dropped this massive conversation here in front of us. It was not part of my plan, Drew. This was not part of my plan. Cannot ruin an interviewer's plan. Brains. I'm just kidding with you. This is wild.
1:08:03And so what role do you play for Quarter Call? So I'm the designer there. And I saw a video on Twitter by Robert Scoble a year and a half or more ago. where he interviewed Han, who is the CEO at Cortical and the founder. And he was up in Han's hotel room. Han was there for like a trade show of sorts. And Robert met up with him and like filmed what he's working on. I was watching this thing. I'm like, this is freaking crazy. And it's all the stuff that I've been thinking about in my mind about how things are going to go in the future and where they're going to end up. And I was like, I have to get a hold of this guy.
1:08:46So I asked Robert, I'm like, dude, I'm like, can you get me in touch with this guy? I'm a designer. They need design help. And he's like, I think it's too early for that. And so he wouldn't put me in contact. So I was like hitting up Han on LinkedIn, on Twitter, on all the ways I could find. Eventually he responds to me and we meet up. Conversation goes well. They're not totally sure they need a designer or anything like that. And I ended up talking to him for like a year. And finally he's like, all right, cool. We need a designer. Jump in. And so I got to join the team in like December and then quickly built out this website in January and launched it in early February.
1:09:25And then had a little bit, I was able to change some of the colors on the CL1, but didn't have any influence on the way that that thing looks. I will on the next iterations. And then now working on, going to be working on the cloud interface. So when you log in, you can, you know, get yourself set up on coding against one of these brains in the cloud. Brains in the cloud. I love it. Okay. So let me zoom out then like this. Who was this person again at GoDaddy that pulled you aside and was like, I was on the YC website. Who is this person here? Like, I kind of feel like that person in this moment here.
1:10:05Was that person again? Was he your manager or was it? Yeah, he was my manager. Your manager. so here you are clerk and i know clerk because they've sponsored our show before uh met ceo great team there super cool where they do auth i mean very focused on next and the front end kind of things for when it comes to authorization and this whole entire ui kit so here you are you're working at clerk you are you i i don't know what you're doing honestly you got a job you got several jobs? How do you be a designer for Cortical, Clerk? How are you doing all this? Yeah. So at Clerk, I'm actually on the leadership team there.
1:10:51And I am the head of design. So I've got a team of like, I think there's 12 of us now designers. And then I'm also the head of commerce and billing, which is our new product, which has a very large team right now as we're getting prepping for launch in the next week. So yeah, lots of responsibility there. That is, that is like pretty much all that I work on is, is clerk. The reason I can work on cortical and clerk at the same time, cortical's designs needs are, you know, vastly less than, you know, what clerk needs. And there's not a team essentially that I have there. It's just me. so it's way easier to manage um also uh it's not like a paid job i mean i have equity but it's not a paid job or making a salary or anything and clerk is also cool with people doing side projects like a lot of people to come in and do side projects um and have side businesses so as long as it's you know not interfering with work and you're not doing it during you know times that you need to be at work then you're good to go and uh so that's that's my situation there but i just really wanted to be a part of cortical like to say that this is i'm not kidding man it is literally the first commercially available biological computer and i freaking designed some of it i mean i wasn't the guy who came up with the idea or anything like that but i designed the whole site and helped design a little bit uh and it's cool to be to be a part of that and um it there's a lot of good that can come out of that technology.
1:12:30Personalized medicine being one of them, you can take your skin cells, literally Adam, you can have your skin cell turn into a neuron, put into a CL1 and instead of testing, let's say you have some brain disorder or some chronic disorder that you're trying to get rid of, epilepsy, cerebral palsy, there's a bunch of stuff. Let's say you you want help, but here's these drugs that were developed and they could be fatal. Like there could be all these risks. You take that thing, that's your one shot, right? Well, let's say you could just put that thing, drop it into your other atom, your mini atom, your brain, and see how it responds, right?
1:13:13How does it affect that? If it dies off, you're good to go. It didn't affect you at all, right? There's just so many cool things that can come about. And then as a drug manufacturer, where you're like, how do I test this in people? Well, you can't. You have to get all these approvals. You have to first do mice, then monkeys, then this, then that. And it takes a freaking decade by the time you get to people. And then so with this, you can just start testing it right away. There's just so many cool things that can come out of that technology. It's very nascent. So folks don't know exactly how it's going to be used, what it's going to be used for.
1:13:47But there's just so many potential use cases. and then clerk separately is a freaking awesome company the thing i like about clerk is that if i were to run a company it would be very similar to how clerk runs so i feel very at home at that company which is really cool and you know there are a couple they're like a step or two beyond what i what i was able to get to with my companies clerk is essentially plaso what i my My old company 2.0. It's the exact same thing. Embeddable auth, embeddable billing. That's exactly what Plasso did back in 2014. And Clerk is the same thing, just the React way, right?
1:14:24The newer style. And so it's cool in some ways. I have a lot of experience with that stuff. So it ends up working out. What made you, this might show some of your cards a little bit, but like hearing your story, I suppose, in this conversation, and then being aware of what you've been doing for the last decade, let's just say. To me, I wouldn't think that you would need a job. That you would just have enough wealth and you could just do whatever you want. What makes you take on this job? You would be wrong, Adam. Am I way wrong? You would be wrong, Adam. Oh my gosh. Yeah, yeah. Sadness. No, it's not sadness.
1:15:06It's not sadness. It's great. Yeah, let me rephrase that. It's sadness that that was wrong, not sadness that that's true. Yeah. I invested a lot of money smartly. And I used a lot of that money for letter. So I made like in the span of between 2018 and 2022 or three before the market crashed, I made a lot of money. And I like built this huge office and addition and movie theater and all this kind of stuff in my house. So like my house is like this premium playground. And then I spent all the other money on the letter, which wasn't my intention.
1:15:52And so a lot of that extra money that I was counting on to have long term, I made the decision to like spend it. And I was like, well, if it doesn't work out, I'll just get a job. I'll still be able to maintain the lifestyle I have if I can just get a job. And I should be able to get a job fine. So, obviously, ideally, I didn't want to have to get a job. But the play with letter didn't work out. And so, I did have to. And so, that's where I'm at. But what's cool is like the investors who invested in letter were all like, we've never seen anybody do this. So this is really cool that you're doing this, you know, taking on this risk.
1:16:34And, you know, most of them said you shouldn't put your own money into your own company. That's what investors are for. But they all appreciated that I was right there along, you know, with them. so that even though the transaction didn't work out for them financially i think for me it worked out and that they have more respect for me and so should i raise money for something in the future i think they'll you know their walls will be faster opened to me than maybe previously so yeah yeah exactly exactly you win some you lose some man you do win some you lose some you know I'm way better off than when I started, though.
1:17:13So it's not like I took any steps backwards. It's definitely, it was like, you know, 100 steps forward and some steps backwards. Well, don't let this seem like I'm judging your, this is not a report card for Drew, okay? Yeah. It's not me examining your English and your social studies and your gym, because gym is always a class, too. You know, I'm not examining those things and saying, okay, great. You've, you've passed the sixth grade. You can go to junior high kind of thing. That's not what we're doing here. Yeah. But I think we're peeling back the layers a little bit to just understand like the reasons for the move.
1:17:46So it sounds like it's something you got some equity in quarter call. The CL one sounds super dope. I mean, I'm not even talking about it. Not because I'm not interested because I just know it'll take over the whole thing. And so like, I'm not even going to go there yet. and then you have obviously value con so you brought this back after what you said it hasn't happened for seven years it's been a big deal for a lot of folks you know you're bringing back the conference um what can we expect i suppose there what can we expect with clerk what kind of uh other good next moves do you have in you yeah i would i would suggest if you're listening go check out valuecon.com sign up come out hang out it's going to be a good time i've got a lot of cool speakers.
1:18:33They're going to be there. A couple that I'm just waiting on the final, like not actual signature, but final go ahead. And then they'll be up on the site too. But it's going to be a good time. It's like a vacation. So if you want to like get away, bring your family. If you don't have family, just bring yourself. Come hang out, hang out with old friends, meet new people. It's right on the beach. We do s'mores on the sand. We all get lunches together. It's a good time. There's one track. so everyone's in the same room at the same time um and you end up making a lot of friends folks really love their experience at value con have done it for like i said six years and then there's a break so um lots of good things that people have said about it um so come out value con would be a good time if you're in design in engineering and tech at all like uh there's going to be a ton of stuff that you can learn from it one of the other focuses of value con is giving people who don't normally speak at conferences, a chance to speak at a conference.
1:19:35And, you know, if they're doing something really cool, I want to feature them. I want them to, you know, have a platform to talk about what they're doing. So, that's also another focus on value con is getting folks who've never spoken to come talk about what they're doing. So, yeah, definitely come out for that. What's new in Clerk is we are right on the cusp. I mean, maybe when this thing, I'm not sure when this episode will go out, but maybe when this episode go out, Clerk Billing will have launched. Should have it next week. Yeah. Clerk.com slash billing is where you'll go for that page. And what's really cool about Clerk is that it makes authentication super easy.
1:20:14Kind of like Stripe did 15 years ago or whenever they started, they made this pitch that, you know, we want to own the credit card data at your company and you're no longer going to have ownership of it. We're going to own it, but we're going to build some really cool software around it to make it really easy to use and build in a bunch of fraud and safety and monitoring protections for you. And they actually won that argument. People stopped using whatever they were using to reconcile credit cards on their own. And they gave all that data to Stripe. And Stripe built some really cool APIs and stuff around it to make it really easy and actually easier to access than if you'd done it on your own.
1:20:56And so Clerks doing the same thing with the user table, which is for a lot of engineers a harder thing. But as we scale engineering and as it goes downstream into less and less technical folks with AI is now happening, they don't really care. they are happy to give up their user table to clerk to say you handle the user record because you're going to build this amazing software around it these cool apis these cool uis they're just going to make it where i don't even have to think about this stuff right so clerk's done a really good job to date on that argument and winning folks over and showing how much better it can be to build your app on clerk than not build your app on clerk the next major step to that user from a company perspective is like, I want to make money off this user.
1:21:47And so that's where this new product billing comes in. So it's really the second product that Clerk will have ever offered. They have off and now they have billing. And so we're going to, everything that we're building at Clerk in terms of billing is all native to Clerk. So we're not actually using Stripe's billing product. We're just using Stripe for payments and eventually PayPal for payments. And you'll be able to pick between them. And for right now, though, all of the recurring billing logic, all of the invoices, the payment attempts, the emails, all that stuff is native and built into Clerk.
1:22:24And what that means is we can tailor these plans that you create, these subscription plans you're going to create to SaaS, right? And we don't have to account for every other type of business like Stripe has to. So we can get very narrow focus to make the UI and the UX way better. Then separately, there's this idea of entitlements. Okay, someone signed up for a bronze plan, and this is a person who signed up for a gold plan. Well, what do they have access to? Well, usually if you're using Stripe or some other program or system, you've got to then build out these entitlements in your app internally.
1:23:00And you have to somehow reconcile them and keep them in sync with the plans that they're signing up with. And you have all these if statements all over your code saying, if bronze plan and if has this feature and if that entitlement do this, that, and the other thing, but if this, blah, blah, blah, blah. So it gets crazy. And so at Clerk, what we're doing is we're merging those all into one thing. And so when someone signs up or when you're creating your plan, you can assign features to it and entitlements and you can set the parameters on those. And you can have them be the same on gold and on platinum by just adding the features to both of them.
1:23:32or you can slightly tweak that feature to have this number of credits versus that one has this number of credits. You can do all that right from the UI inside of Clerk. And then in your code base, you just use our has function, auth.has, the name of the feature. And then it will automatically check to see who are they logged in as. And if you're in an organization situation, because Clerk also supports orgs where you have roles, this has function will automatically look at the role this user is logged in as. Are they logged in as an admin or a member? And maybe admins have the thousand credits and members only have the 50.
1:24:13And it will just automatically figure that out for you. So then the entitlement scenario on actually building out your app becomes way easier than it ever would anywhere else. And I mean that sincerely because that is the truth. so it's just it ends up becoming just a way better experience as an engineer and you can get to like making money so much faster just yeah so this is the goal right yeah i mean uh when i recall some of the details behind clerk was like it was really great uh i think they were struggling with migration from other auths but like really great for green if you build here It's amazing because you don't have to backpour all this cruft that you are used to building.
1:25:00You could essentially just start green and use the has function and other things that are available to Clark to make it more of a clean flow into what you're building versus migrating from something else like Auth0 or whatever that might be out there. Yep. Yep. I think that's accurate. We are working right now on migration tooling and improving that stuff. That's like a separate team working on that stuff right now. So it'll all get better in the future. And what's cool is like the reason Clerk is called Clerk is because we want to take on the boring administrative duties that you don't want to deal with.
1:25:39And to start with, to actually do that, you know, all software, if you think about it, all software is just decoration on top of a user record. Every single piece of software is that. And so you got to start at the user record and then you can build out these other products like Auth and like a number of other things that we're going to launch in addition to Auth. And we're going to move into other business verticals, which is going to be great. So what's crazy is if you look at Auth, it's like a 10 plus billion dollar industry. I don't know, tens of billions of dollar industry. But if you look at payments and you look at commerce, that's a multi-trillion dollar industry.
1:26:14It's like a whole nother scale. And so the way I see it is that our billing product will become the breadwinner, not overnight, but decently quickly within a couple of years at Clerk and will outpace in terms of revenue all the businesses that we launch by a factor of many, which is great. We help people make money. So it'll be good. It'll be good. What else? What is left? We got a few more minutes to chat, about three-ish from my examination of the clock here. What else is left unsaid? What else is left? What's the next big idea? Can you tease your next big thing? So I'm working on something.
1:27:04And when I say that, I mean that very loosely. Every week, I get like an hour. It'll slow down soon for me after launching everything. But I'm barely working on a thing called Opacity. And this comes from my experience working with teams. And I've teased Opacity on my Twitter account, but I don't really have a website or anything for it yet, though I do have an entire product designed in Figma. And we're working on the engineering side of it now. So this is something I'm working on with Michael Jackson. So in our spare time, he created React Router and Remix. And he and I, we live very close to each other.
1:27:48Our daughters are friends and we see each other all the time. So we've always wanted to build something together. And so we're working on this now together. And so Opacity is, it's a way for designers and engineers too, but mostly designers, to build and maintain components, right? So the idea of building a web interface, not a marketing site, but like a web app, components are the way forward. And people have known that for a while. You don't really build things willy nilly anymore. You build via components, whether you're choosing React or web components or whatever the crap. You have this idea of this isolated set of functionality based on UI, right?
1:28:36And since that is what everyone's doing, and that's the way forward, there hasn't really been a tool yet to make that happen in an easy way. If you look at Figma, you can build a component, you can drag things out and create instances. But then when you actually want to turn that into code, they have this thing called dev mode. And the idea of dev mode is a mission that says we will never be able to make these things, the idea of a design and the coded version, be the same. The fact that there is a dev mode toggle means we have resigned to the fact that they will never be the same. If they could be the same, there would be no need for a dev mode.
1:29:16They would just be the same. Figma's canvas is not a DOM. it is a giant WebGL thing, right? So they can never match the same. As a matter of fact, if you look at the way they do blurs, if you look at the way they do drop shadows, they're never one-to-one with what you see in code. They're bordering. All that stuff works totally differently because it's not the way the DOM works. Not that one's better than the other, it's just it's not how the DOM works. So you can never visually get one-to-one. and they always have to build all these features like auto layout and this and the other thing just to try to like match the dom and so what opacity is is a canvas that is the dom and you drag and drop just like figma you build boxes uh and and the boxes that you build and the inputs that you put in there everything is all actually just dom and so you can style and design it and you can create a component and then you can go to the pages tab and like build out a whole page where you're creating instances of those components, dragging them, dropping them.
1:30:22But the thing is, everything that you're doing is actually code. And so the export of opacity is a NPM package. It's a package that you can include into any of your projects that is essentially all of your components coded out. You don't have to care what we use to style it in CSS. you don't have to care about any of that stuff. All you have to do is like, okay, export this thing. And by the way, there's full, like, it looks like GitHub. It's like full version controlled and everything. Because that's the other major piece I want is like, there has to be, like in Figma, if you change something, you don't know who changed it.
1:30:57When did it break? How did it break? You just destroy everything just by one click. And there's no rollbacks, nothing. Like opacity has all that. Opacity is like GitHub and Figma combined. But the export is an NPM package. and then you have all these props that you set up in opacity. So you could say, okay, the title color can be this, the text size can be that. You can set up any props you want and then you can expose those. Let me rephrase. You can set up any variables you want and then you expose those variables as props. You can choose which variables you want to expose and which you don't.
1:31:33And then those props are now available in code. So when you're including my cool new checkout component, all these props that you said you have, you can include them in code. And as you know, with any prop, like any component-based system, you can actually extend props. So if you have your business logic that you want to add to these components, then you can. You can create a, you know, an actual checkout is the name of the component, which is really a wrapper around the checkout component, right? And it has all your business logic in it. And maybe you really just use the actual checkout component throughout your code base.
1:32:12So you can attach these other props to it, but that's, you know, that's up to you. That's how, that's however you want to do it. We're, we just care about the look and the feel and also the, some of the eventing there's events built in. So you can like have click events, have hover events, all that stuff that is just like not going to change. Maybe you want a hook for the click event and we, we, we give you a way to do that. So it's the idea of like, if you were to build actual products visually, like this would be the ideal way to do it. And that's what opacity is. Eventually a Figma killer or a Figma acquisition.
1:32:50Could this be your, could this be your whale? Maybe. We don't want to take any investment. We just want to build it ourselves and build a company. Yeah. Cashflow company. It's not saying we would never sell. I'm not saying that whatsoever. But I don't think it would be a Figma killer in that people would use this in place of Figma. Because if you're designing a website that's not an app, you're going to probably want to use Figma. It's built for that sort of thing. But if you're going to build a UI, I would think that hopefully most people will be moving off of Figma and onto Opacity for that.
1:33:31That's kind of the goal. As a matter of fact, one of the things you get whenever you create a new project in Opacity, you ultimately create a set of components in that project. And you can share that. And you can spread that out on the web to anybody you want. And when they click to go to view that page, they don't have to have an Opacity account login or anything. They're viewing essentially a storybook. Are you familiar with React Storybook? so you see your components visually and you can like see the props and like change them and edit we're not using storybook we're using our own thing but it's essentially storybook and you can see all the components and like mess with them and um so when you think about it that way that's that's what we're building and that's like that's what you would want to see if you're like here's our design system oh just use this link it's already built for you this is exactly how everything works and and here it is all visually um what's crazy is this product doesn't exist anywhere.
1:34:33Yet it's like the thing that everyone would want. So it's cool. So all you got to do is get more random hours over the next, however long to do that. Yeah. Well, I'm sure that I'm sure this next big idea will come to fruition because you're Drew Wilson. That's how it works. At least in my experience with you, maybe your own version of your own path is a little different. But my, for me, outside looking into your world, that's how it seems. It'll happen. You got to add an extra F in there. It comes to fruition and failure. That's usually what happens. Ah, yes, yes. Well, I mean, there is no sweet unless you've got some bitter, right?
1:35:18The bitter is never as bitter unless you've tasted the sweet. Yep. Yep. Yeah. Cool. Well, I'm sure we could talk for longer. It's been awesome having you back on the pod. It's been way too long. If this didn't, you know, cover everything you wanted to, I'm happy to have you back on and dig even deeper. I mean, we barely scratched the surface of things I think we could talk about, but it has been. Dude, I'm totally down. It's fun chatting with you. I've missed this. It's been great. I mean, if folks don't know, we used to run a podcast together called The Industry. Oh, my gosh, man. Back in 2012.
1:35:55Yeah. So it's been a while. It has been a while, man. It's always fun. Jared Arondu, me and you, the industry. Yep. The random show. Yeah. The days, man. The days. And yet, we've never met face-to-face. I've never been to ValueCon. We've never shaken hands. Yep. Dude, the internet's crazy. You could do stuff like that. Yeah. You could be a founder, co-founder situation with a buddy. and never really meet them. It's wild. And I realized in this conversation, in the first few minutes of it, was that you were the person I think I'd learned or heard the phrase more frequently than I ever have before called, what the crap.
1:36:42That's one of your phrases you like to say, because I'm sure you like to cuss a lot. So I'm sure you say what the crap instead of something else. Yeah. And I think I began to say what the crap, because I'm also like that. I like to just cuss less. I'm just not much into profanity. Although I do do it. Just don't do it publicly a lot. You know, stub my toe. I'm going to say a bad word. I'm not going to say what the crap. Yeah. But on a podcast, it's what the crap, you know, kind of thing. Yep. Dude, I hear you. I hear you. Yeah, it's good. Like my kids now are old and grown. Almost all of them are teenagers now.
1:37:24and you gotta watch yourself they like to do what you do they do and they emulate you even if you don't want them to if you're like don't do what I do they're like listen my default my default gear is dad or mom gear like wherever they're going I'm going that direction so it has been fun Drew thank you so much for sharing your journey again and getting into some details and we'll see if I can get you back on man yeah dude it's been great thanks again for having me and uh we'll chat later all right man
1:38:01well friends i hope you enjoyed this episode it was very much to me like a behind the scenes look in a way you know drew and i are friends and i i felt like this was very much a conversation between he and i and we just happen to share it with the world you know drew's one of my favorite people out there he's always been on the cusp of what's next he's always had a good opinion a good take on what's worthy of your attention what's worthy of your time and where the industry is going and on that note we produced the podcast the industry radio show it's not on the internet anywhere whatsoever to see it was a fun time and i hope you enjoyed it of course a big thank you to our sponsors of this episode heroku love the next generation of heroku coming out retool big fan of retool as you know and recently became a big fan of depot what would you do if your bill was 10 times faster that's the question depot.dev and of course break master cylinder those beats are banging got a new album out there after party check it out changelaw.com slash beats see all our albums okay that's it the show's done we'll see you on friday
1:39:17Thank you.
From the publisher
Drew Wilson is back! It's been more than a decade since Adam and Drew have spoken and wow, Drew has been busy. He built Plasso and got acquired by GoDaddy. He built a bank called Letter which didn't work out...and now he's Head of Design at Clerk and back to chasing that next big thing.
