Chasing that next BIG thing

Well, Drew Wilson is back in the house… It’s been a while since you’ve been here.

It has.

I want to say – gosh, I didn’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 of 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. ValioCon, man.

And part one and part two, for whatever reason. That was the name of the show. It was Drew Wilson / Valio - Part 1 and Valio - Part two.

Oh, wow. Maybe we’re talking pre-ValioCon, and we’re talking back when I was making stuff under the name Valio, which would have been like 2009 or something.

You know, I don’t know. ValioCon was mentioned… You were at [unintelligible 00:06:15.07]

Oh, dang. So that’s probably like 2011.

That’s 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 too at some point, but I don’t know when.

Yeah, I’ve been on here before, and I think – it was a while ago. It was a couple years after that one, for sure. So 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 has been a while, man.

At least a decade. I would say at least a decade.

I think maybe one or two tweets, or something like that…

Yeah, here and there. Nothing special. You got busy, though.

Yeah, I got busy.

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 fun.

How does that feel?

It was – dude, it was incredible. It’s like one of those – I mean, it’s not to the scale of “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 do the whole investor thing, and then you sell it and you make money. And 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 accomplishments. 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. The things you’re used to in regular people land in terms of success is way smaller than what folks in tech are used to.

I don’t even think you were a dad. When was your kid born? What year?

My first was 2010. I have three kids. So 2010, 2012, and 2013. Yeah.

Okay, so you were a dad, barely. Did you hide it? Was it a secret birth?

No, no, no.

[laughs] It’s a joke, obviously…

Yeah, 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 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. But yeah, it’s always been like a conscious thing to like not post about our family or our kids or anything like that. We’re weirdos.

I see 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 track pad and a little click button, and it fully, fully, fully works.

Wow.

[00:09:52.15] I got that thing on eBay. You can boot it up. It came with a – it’s a 16-pound laptop. So this is a 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…

Yeah. 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 and 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’ve kind of always got to leave it plugged in, running just off battery. Even though it’s fully charged, it will only last like a minute or two. But 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?

Wi-Fi 1.0, I think.

Right. The earliest of Wi-Fi’s…

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’ve got to, 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 computers.

You know, off camera I have an Apple II I think it is, or a Mac classic…

Yeah.

I think it’s an Apple II, if I recall correctly. It’s just a prop. It’s just for - I call it art. It’s just art. It doesn’t work.

Yeah. 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 like the tall [unintelligible 00:12:03.18]

Yeah. Okay, so it’s a Classic, not a two. I’m looking at the front of it and it just says Macintosh Classic on it. It’s got a little floppy drive on there, and whatnot.

Yeah.

You know, all the good stuff. It’s 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 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 - is the Macintosh Classic. On the right is the 2013… What do you think it is?

2013?

The trash can.

Oh, wow. Yeah.

The trash can, right next to it. It’s kind of funny, because you see this – I suppose maybe the undercurrent to this conversation could be iteration. It’s this iteration of monitor, compute, floppy, keyboard or external devices… Same idea pretty much, except for the monitor, with the 2013 Macintosh trash can, which was the Mac Pro… And 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 wild too, like - this laptop is huge, but if you take the little back portion out of consideration… Because that’s where a lot of the larger motherboard and everything is, and the battery mainly… And you just collapse that down and you just take the clamshell piece, it’s essentially the same size as a modern day laptop. It’s a little bit thicker, but it’s not like insanely thicker.

Yeah.

So it’s wild how [unintelligible 00:13:49.08] stay the same.

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… You can look it up on YouTube, you can find the Macintosh Portable commercial, and they’ve got like this guy in 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.

[00:14:26.11] And they didn’t. [laughter] Oh, man…

Because they’re so heavy.

I missed you, man. You know, what you have is this – you have 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.” Like, you have this sort of like uncanny instant intuition of 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.

Crypto… Crypto… Crypto won’t.

You’ve got a pretty good intuition.

[laughs]

What’d you say?

I’m trying to be all hot-takey. I’m saying “Crypto won’t.”

Oh, yes. Crypto won’t. Are you against crypto?

I’m not against crypto, I’m just against the idea that crypto is the savior of the world, 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 it’s just on a different protocol. And 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 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. That’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 less than a fraction of a percent.

Yeah. What are some hard beliefs that you would say you have?

Crypto will be great for collectibles, and hopefully also another spot, like through Bitcoin, 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 industry… In that by doing so, by buying up a bunch of properties, it makes property go up everywhere; property values go up everywhere, and it makes it harder for regular people to buy homes at an affordable price… That’s one, if we’re staying on the crypto train. If we’re not staying on the crypto train, another hard belief - let’s see… 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 start to realize that “Okay, this person does one thing, and they’re probably only ever going to do one thing.” And 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 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.” So that’s the segue into my hard belief. Here comes my hard belief.

[00:18:15.21] Your hard observation.

That was my hard observation, so now my hard belief…

Okay. I’m down. Take me there.

I don’t know how to phrase this, so I’m just going to think of how I could phrase it… It’s something that I’d always thought about, but I’ve never had to put it into a concise set of words. So 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. But 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 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.

Right.

But if you’re not that, you’re not an engineer. You can’t understand how to build something. And you’re not a designer, and you can’t understand how to build something in that aspect… It’s like, what are you doing here? 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 in product. Those people are usually the first to go, 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? Where’s all the documentation of what you guys are doing, or where you’re going, or how this works?” No one ever made it. So what was the purpose of this product manager, besides receiving a paycheck for doing almost nothing?

Wow… Okay, so –

There’s my hard belief. [laughs]

…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. So when I sold my last – not my last startup; one of my last startups to GoDaddy… I was a part of GoDaddy, which is a great organization, 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, and they’re able to convince themselves and an employer that they do. So you look at what these other teams are doing and you’re like “My gosh, you’re just running in circles. You’re never going to [unintelligible 00:21:36.19] I came into GoDaddy as an acquisition, and we moved our tech Plasso, 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 S**t Done Award at GoDaddy. They have an award that they give out, which is really cool.

Hah!

[00:22:08.04] 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. I’m like [unintelligible 00:22:13.08] 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. And 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, you’re going to turn out crap.

Yeah…

I think you see that happen. There are also other companies that I’ve been a part of that suffer from the same things. It’s not just them.

Break: [00:22:52.22]

So 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. You know that, right? This is a podcast. It’s a podcast, man.

Yeah, let’s take a look at these people. [laughs]

Just because - and I never asked anybody to do this, but just because I haven’t talked to 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 TL;DR on Drew Wilson.

Hey… Alright, so I’m pretty early to computers and the web, built my first website when I was 13 in ‘96, taught myself how to design on Photoshop too, and 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 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. I 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. I built these icons called Pictos, which tons of people still use… It’s still the default icon as the shopping icon in Shopify. That went off like hotcakes. And then I built a couple of different e-commerce platforms, one of which was called Plasso. And like I said, I sold that to GoDaddy in 2018.

I also have a conference that I run called ValioCon, valiocon.com. I 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. A conference for designers and engineers.

And then after Plasso, I wanted to take on something that I thought would be a really tough challenge, and it really was, and that was a bank. So 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. I ultimately couldn’t make it work, so I had to shut that thing down.

Then ended up at AngelList for a little bit, and then left there and jumped over to Clerk, clerk.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. What 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 being like “I’m going to figure out this PHP stuff.” And you just figured it out. Next thing you’re building stuff, you’re building iOS stuff… And you’ve always had this – it’s almost as if you’ve got this Drew Wilson style, sort of like stuck in there. And whatever comes out, it just oozes this certain feel, this certain – even when I go to valiocon.com right now, this feels like a Drew Wilson design. This doesn’t feel like – the lettering is cool… Did you do this lettering?

Yeah.

I mean, everything is – how do you just do everything, Drew? How are you a renaissance person?

Well, you just – I don’t know, it’s many, many years. 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, something like that. Before there was layers.

[unintelligible 00:29:28.16]

Before there was layers.

Oh, before there was layers… Oh, my gosh.

Yeah. Can you imagine that? [laughs]

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.

You’re blowing my mind here.

[00:29:48.18] So it’s just like a bunch of years – 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. [laughs] 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–” There’s these accreditation tests, and these different certificates you can get. So 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 like crammed for in like a week. Normally, people spend like 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 testing – the government testing facility was shut down because of COVID. They’re like “We’re not going to open for like months.” I’m like “Oh, crap.” And that’s when I found out I actually don’t have to have this certificate.

But 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? Would you just get lunch with a stranger?” And he’s like “Sure.” [laughs] 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, it’s called Una.co. We were like their first big customer. Built a lot of security stuff ourselves, because they didn’t have any at the time. They modeled it after what we did. And yeah, now I know a ton about banking, in case that’s ever useful. And about finance. So that’s how it happens. You just go on these tangents, here and there, and the other place.

I’m not sure that’s how it happens, Drew. I’m really just not sure that’s how it happens. [laughter] Okay? 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. Can 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 worth owners, folks out there… And I’ve 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 defunct, I’m really curious about this - what did you have to learn about banking to make Letter possible? 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. But it just isn’t. It just absolutely is not. The way that 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. A 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.

[00:34:20.04] Really?

Yeah.

How do you get approval for – 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. To do a new type of lending product - if you’re a federally chartered bank, meaning you can operate in any state in the US, 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 US 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, your average mom and pop bank, which barely exists anymore… I mean, they’re technically considered, financially considered a small business. They’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. And it will never change.

What’s enormous?

Millions and millions of customers. We’re talking like Chase size, Wells Fargo size, or some of the new startups that have gotten there, who can now become profitable. What’s the one with the gold card? Robinhood’s getting into banking… And what’s the other R one? 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. These regulations are just too stiff. And you’ve got to have way more money than what they have.

So banking is a very difficult… I mean, even Silicon Valley Bank failed. Banking is a difficult industry to be in, especially the one I jumped in. I jumped in thinking “Wow, there’s nothing like new and modern for high net worth individuals. Let’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 where their money is. They just want their manager to deal with it. 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. So what happened to me was I had sold my company, Plasso, to GoDaddy. And it was literally a dream scenario. An all cash deal, with the option to jump on as an employee, and get a good paycheck and additional payouts if I stay on. So I stayed on there for 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 Plasso 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. So I took out a bunch of loans on the same day just to keep the company going.

[00:38:24.08] I was making enough for myself, but that’s it. And I needed these other employees to help sell the thing. And so I took on massive debt. 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”, 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.” And acquisitions always happen under the guise of partnerships. I didn’t know that. And then three months later, I had sold my company. A little over three months. But to me it was like 10 years of my life. It was just so exciting, and at the same time – it’s like a rollercoaster 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. And so it was a great experience. It was a great experience. The company acquisition team at GoDaddy 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 –”

“I’ve never had money before…” [laughter]

I was like “There’s got to be a site that says what to do.” I’m looking around… I’m like “Oh, there’s no site.” The closest you’ll get is The Points Guy kind of stuff, but that’s 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. Maybe I should build an app for them, to help them manage their money and have this 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 could make a bank…”

“There’s a bunch of old people making banks… I could do it.”

Is this literally right after the acquisition time frame? The three months are over, the acquisition goes through, all cash, you’re an employee, then Letter? Or is it like a year down the line? Help me understand that compressed timeline bit.

It’s all at the same time.

Really?

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 it’s not till like a week or so out that you know like “Okay, this is when it’s happening.” So this whole time it just could go either way. But I’m like “Yeah, it’s gonna go my way.” And so I’m looking at this house that I live in now, and I’m like… [laughs] 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, 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, I just flat out didn’t have. So I’m like – they wanted, basically, I don’t remember, it was like $20,000 or $40,000. And I’m like “Will you take $1,000?” [laughter] I’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.

[laughs]

[00:42:22.28] And “I promise, I promise it’s there.” I have no idea why they just were like “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’ve got to pay for the house.” And I’m 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 “Okay, fine…” And then that week happens, and literally like a day or two before I needed the money, I got the money myself, and I was able to give it to them. So that’s how optimistic I can be.

I’m trying to remember your original question… But 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 Letter. And I wanted to just chill out and not like work on anything other than this one thing I was doing. And so I got through that initial launch, and 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 talking to another buddy of mine who worked at GoDaddy, that I’d met there, who had sold his company to GoDaddy the year before me… And - yeah, I was just thinking more about finance and 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… And even still, it’s like, this is so manual. Everything’s a phone call. Everything takes forever. It’s like, there’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 Letter ended up – originally, we were going to be 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. 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. Are 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 going to have you talk to another partner. They’re not sure.” Talk to another. This was four times. Four times I had to talk. And finally, they’re like “Okay, okay, we’ll let you in.”

What was the pitch? I don’t want to interrupt you, but 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. I think it was the branded bank, and the pitch was just like “High net worth individuals –” 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 2% 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.

[00:46:06.06] 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 win, because we’re modern, we’ll have an app…” Literally even now, other than Letter, 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 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 had a huge team at GoDaddy, built up the payments team… I think we were at like 16 people was my team at that time… Plus other teams 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, investor meetings… And I think it was like a day or two before demo day my boss was like “Hey, do you have a second?” And I’m like “Yeah, sure.” He’s like “Oh, how’s it going?” He’s like “I’m going to screen share.” He’s like “So I was going through this website”, and he has YC’s website pulled up. And he’s like “And I scrolled down and I saw this person.” And it was a picture of me… [laughter] A picture of me and Letter, the company… And he’s like “So what’s going on?” [laughs] I’m like “Yeah, I’m probably not going to stay here forever…” So my plan was I was going to get in YC, raise money, finish up the last bits of stuff I had to do at GoDaddy, and say “Hey guys, I’m leaving.” But he preempted that. So then at that moment, I had to be like “Yeah, I’m probably not going to stay. I’m sorry.”

Well, that was only a few months after the acquisition, though. Didn’t you say you had to stay as an employee for a bit? Maybe a year in?

Yeah, so this was – so I came up with the idea 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. I started the company, ran the company I think for like a year before we jumped into YC, or something like that. So yeah, there was about a year and a half in between that.

What was the company doing while you were preparing for YC? Like, what was the company, running the company?

So it was building the product… Like I said, 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. There was already a couple of other players in the space. It seemed horrible to do. And it is. And if you’ll talk to those companies, it’s horrible. As a matter of fact, there was another banking as a service provider in YC, in my group, a guy named Darragh Buckley. He was the second hire at Stripe. Super-cool guy. We almost – we were talking about merging our companies at one point. But he was doing that. And so - yeah, we decided not to do that.

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. And then we just decided, “Let’s just build that retail thing. That’ll be way better.” It was not really way better.

What’s the 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?

[00:49:48.07] It ran out of money. It ran out of money. That’s the practical reason. The real reason is, is we approached the market incorrectly, and we didn’t have the cash to correct. 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.

So 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 - 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… He bought up all the American rodeos, he bought up all the cable programming for Western-themed stuff, he 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 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. And 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 your bank.” And so this was me trying to get this deal across the line for like seven or eight months… And it was just like, it was always right there. We had paperwork sent to them, they would revise, send back, and just like… I’m like “It’s so close. Just sign the freaking paper.” But then it never happened, and that was early 2023 when they pulled out. And that is the exact same – the same month they pulled out, it’s the same month as 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. We created our own in-house lending platform, where you get a loan in a few seconds, and it was 100% 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 fun. So that’s why it didn’t work.

[00:53:43.07] 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 is 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 you didn’t really want to; you weren’t interested in it. You gained that. And now here you are, creating a freaking bank. Like, come on, Drew.

People always get hung up on the bank thing, and 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.

Well, it’s just unlike me. I would 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 – well, I think it’s actually strange now that I’m realizing what 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. And in the same person. [laughter] I don’t understand that.

Yeah, I don’t think I ever had bank on my bingo card either. Really the reason I wanted to do it is I’m like “No more making little apps. Done. I’ve done that to the nines. I just want to do something big, that could become a big company.”

A big swing.

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 cashflow. 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. It’s like, it’s what you would think of as wealth. That doesn’t happen when you have a huge amount of cashflow. 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 cashflow, 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, on a small scale, that lets you not have to work somewhere, that lets you get to experiment and do whatever you want… That is the successful life idea. That’s not the successful finance idea, that’s a successful life idea. And 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 cashflow. And so learning all these things that I’ve learned - there’s always so much more to learn. So I’ve got to get myself another cash cow, and then hopefully I’ll consider myself set. But until then, I can’t stop the doing of the things. 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 Plasso, 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, or however you want to frame that. You paid the employees, you paid early folks who had sweat invested into you with their loyalty, and their abilities, and their friendship, and their whatever, however you want to frame that. And then you obviously had your own money, that was from that, you took on, it sounds like, some massive debt just to keep the company going. I assume that cash 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. Did you lose a bunch on Letter, or did you kind of come out even?

[00:58:37.08] 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?

Yes, millions of dollars.

Millions of dollars. And this is your own cash.

Yeah. For me, it was like a – the decisioning was “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.” And 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 was the best investment you ever made, Drew.” But if it doesn’t work out, they’re like “You probably should have cut your losses earlier.” [laughs] How do you know in the moment? You don’t. And so sometimes you win, sometimes you lose. Actually, let me rephrase that… You always lose, and then sometimes you win. [laughs] You’re usually losing, and then sometimes you win. So yeah, it makes the wins all the more sweeter when they happen.

For sure.

But at some point, you know, I’m noticing. I’m 41 now, and 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. I’m so sick of it.” 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. I freaking built a CSS interface to your database with FireRift 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… [laughs]

You like that, or – is that a good thing or a bad thing?

I don’t want to offend anybody, but no, I don’t like it. So I don’t know… It just gets old. It gets really old. All these people are 20, and I see them like “Oh, just raised money through YC”, I’m like “Dang, you look like you’re a baby.” [laughs] And I’m like “Well, it makes sense.” They’re young and hungry. I still feel hungry, but I’m not young.

Just not young anymore.

My big attempts overall turned out well, but they were never like big-big. So I still am after my big-big one. You know, 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. Why 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 what some of these guys are doing when they’re making robots, and stuff. My mind gravitates towards solving problems that are in front of me, not towards problems that plague Earth 100 years from now.

[01:02:03.11] 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. And I think I’ll actually be 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. I’ve always known you as a – I would kind of classify you as an inventor, in a way… Not like a literal like you made something, but you’ve definitely – like, Pictos was not something, and then creating icon libraries became a thing… The way you engineered to deliver that initially… I mean, you invented all these things to make something very simple, that doesn’t have to be that simple. I mean, it could just simply – you could give me some PNGs, or some SVGs now, or whatever. It could just be like “Thank you, Drew.” But no, you went and made it API accessible, or interactable, and like all these different things with Pictos over the years. You’re an inventor. I would classify you as that.

Yeah. And I’ve always been disappointed in myself for not having the ability 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. And I’ve always – practically, it’s broken down to the fact that I don’t have the network to do that. So part of me doing Letter was like “Ooh…” Especially like in YC, or I’m meeting these higher net worth 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. And that’s kind of why that stuff happens. Practically, that’s why it happens. That’s why movies that get made… You’re always seeing the same people making these movies. Well, it’s because they have a network. It’s very hard to break in unless you have that.

Network is required. You’re right. I mean, you can’t just have the skills and the ability and the drive. You have to have the other people [unintelligible 01:04:20.04] Like the CFO with the license, for example, so you don’t have to go and do that yourself.

Exactly.

Cram for a week, [unintelligible 01:04:27.02]

Andrew Carroll, man. He’s a good guy, if you know him. Yeah. One of my big stretches, though, in that 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.

No.

I just launched the new site there. So I’m on the team there as well, doing design… So it’s corticallabs.com.

How do you spell that?

corticallabs.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 CPU. It’s pretty rad. We could take a prick of your blood, or sample of 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, especially 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. And 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. And you can receive signal back from them.

[01:06:05.20] 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. And so you can have a neuron growing in there for up to six months, or a set of neurons. So you can have this mini brain in there, and they 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 the screen.

The idea is that instead of artificial intelligence’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 think like a human… That thing starts at a human, and it’s already there, and it already thinks like a human. So it’s a different approach. What 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…

[laughs]

This was not part of my plan. You cannot ruin an interviewer’s plan.

Brains…!

I’m just kidding with you. This is wild. And so what role do you play for Cortical?

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 Hon, who is the CEO at Cortical, and the founder… And he was up in Hon’s hotel room. Hon was there for like a trade show of sorts… And Robert met up with him, and like filmed what he was working on… I was watching this thing and 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 ahold of this guy.” So I asked Robert, I’m like “Dude, can you get me in touch with this guy? I’m a designer. Do 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 Hon 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 “Alright, 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… And then had a little bit – I was able to change some of the colors on the CL1, but it didn’t have any influence on the way that that thing looks… It will on the next iterations. And then now going to be working on the cloud interface. So when you log in, you can get yourself set up on coding against one of these brains in the cloud.

[01:09:50.18] Brains in the cloud. I love it. Okay. So let me zoom out then… 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? I kind of felt like that person in this moment here. Who was that person again? Was he your manager, or was it –

Yeah, he was my manager.

Your manager. So here you are at Clerk - and I know Clerk, because they’ve sponsored our show before… I met the CEO, great team there… Super-cool, the way they do auth. I mean, very focused on Next, and the frontend kind of things for when it comes to authorization and this whole entire UI kit… So here you are, you’re working at Clerk… I don’t know what you’re doing, honestly. You’ve got a job, you’ve got several jobs… How do you be a designer for Cortical, Clerk…? Like, how are you doing all this?

Yeah. So at clerk, I’m actually on the leadership team there, and 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 prepping for launch in the next week. So yeah, lots of responsibility there. That is like pretty much all that I work on, is Clerk.

The reason I can work on Cortical and Clerk at the same time - Cortical’s designs needs are vastly less than 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. Also, it’s not like a paid job. I mean, I have equity, but it’s not a paid job where I’m making a salary, or anything. And Clerk is also cool with people doing side projects. A lot of people at the company do side projects, and have side businesses. So as long as it’s not interfering with work and you’re not doing it during times that you need to be at work, then you’re good to go. So that’s my situation there. But I just really wanted to be a part of Cortical. I’m not kidding, man… It is literally the first commercially-available biological computer. And I freakin’ designed some of it… I mean, I wasn’t the guy that came up with the idea or anything like that, but I designed the whole site, and helped design a little bit, and it’s cool to be a part of that. There’s a lot of good that can come out of that technology, personalized medicine being one of them. You can take your skin cells - literally, Adam, you can have your skin cell turned 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 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 Adam, your mini Adam, your brain, and see how it responds. How does it affect that? If it dies off, you’re good to go. It didn’t affect you at all.

There’s just so many cool things that can come about. And then as a drug manufacturer, 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, and this, and that, and it takes a freaking decade by the time you get to people. 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, but 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 they’re like a step or two beyond what I was able to get to with my companies.

[01:14:10.00] Clerk is essentially Plasso, 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? The newer style. 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 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. Or 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. Sadness.

No, it’s not sadness.

It’s not sadness.

It’s great.

Yeah, let me rephrase that. It’s sadness that I was wrong. It’s not sadness that that’s true.

Yeah, 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 between 2018 and 2022 or 2023, before the market crashed, I made a lot of money, and I built this huge office, and addition, and movie theater, and all this kind of stuff in my house… So my house is like this premium playground. And then I spent all the other money on the Letter, which wasn’t my intention. So a lot of that extra money that I was counting on to have long-term, I made the decision to 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.”

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 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, taking on this risk.” 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 with them. So even though the transaction didn’t work out for them financially, I think for me it worked out in that they have more respect for me. And so should I raise money for something in the future, I think their wealths will be faster opened to me than maybe previously.

Yeah, exactly. Interesting.

You win some, you lose some, man…

You do win some, you lose some, and I’ve always –

I’m way better off than when I started though, so it’s not like I took any steps backwards. It’s definitely – it was a hundred steps forward and some steps backwards.

Yeah. Well, don’t let this seem like I’m judging your – this is not a report card for drew, okay?

Yeah.

This is not me examining your English, and your social studies, and your gym - because gym is always a class, too. I’m not examining those things and saying “Okay, great. You’ve passed the sixth grade. You can go to junior high”, kind of thing. That’s not what we’re doing here.

Yeah.

[01:17:43.24] But I think we’re peeling back the layers a little bit to just understand the reasons for the move. So it sounds like you’ve got some equity in Cortical. The CL1 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. So I’m not even gonna go there yet. And then you have obviously ValioCon. 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’re bringing back the conference. What can we expect, I suppose, there? What can we expect with Clerk? What kind of other good next moves do you have in you?

Yeah, I would suggest if you’re listening, go check out valiocon.com, sign up, come out, hang out… It’s going to be a good time. I’ve got a lot of cool speakers that’re going to be there. A couple that I’m just waiting on the final – 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’ll all get lunches together… It’s a good time. There’s one track, so everyone’s in the same room at the same time… And you’ll end up making a lot of friends. Folks really love their experience at ValioCon. I’ve done it for, like I said, six years, and then there was a break. So lots of good things that people have said about it. So come out. ValioCon will be a good time. If you’re in design, in engineering, in tech at all, there’s going to be a ton of stuff that you can learn from it.

One of the other focuses of ValioCon is giving people who don’t normally speak at conferences a chance to speak at a conference. And if they’re doing something really cool, I want to feature them. I want them to have a platform to talk about what they’re doing. So that’s also another focus on ValioCon, 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 will go out, Clerk Billing will have launched.

Next week. It ships next week.

Yeah. Clerk.com/billing is where you’ll go for that page… And what’s really cool about Clerk is that it makes authentication super-easy. Kind of like Stripe did 15 years ago, or whenever they started. They made this pitch that “We want to own the credit card data at your company, and you’re no longer going to have ownership 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.

And so Clerk’s doing the same thing with the user table… Which is for a lot of engineers a harder thing, but as we scale engineering into, and as it goes downstream into less and less technical folks, with AI 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… You’re just going to make it where I don’t even have to think about this stuff.”

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 that 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.” And so that’s where this new product billing comes in. So it’s really the second product that Clerk will have ever offered off, and now they have billing.

[01:21:59.11] So 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. 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. And what that means is we can tailor these plans that you create, these subscription plans you’re going to create to SaaS, and we don’t have to account for every other type of business like Stripe has to. So we can get very narrow-focused 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 system, you’ve got to then build out these entitlements in your app internally, and 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 it has this feature, and if that entitlement, do this, that, and the other thing. But if this…” etc. So it gets crazy. And so at Clerk, what we’re doing is we’re merging those all into one thing. 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. Or you can slightly tweak that feature to have this number of credits, versus that one has this number of credits… You could do all that right from the UI inside of Clerk. And then in your codebase, you just use our has function [unintelligible 01:23:45.20] 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. And 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 ends up becoming just a way better experience as an engineer, and you can get to making money so much faster.

Which is the goal, right? I mean, when I recall some of the details behind Clerk, it was really great – I think they were struggling with migration from other auths, but like really great for green. Like, if you build here, it’s amazing, because you don’t have to backport all this cruft that you are used to building. You could essentially just start green, and use the has function and other things that are available to Clerk 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.

Yup. Yup. 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 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. And to start with, to actually do that – you know, all software, if you think about it, all software is just decoration on top of the user record. Every single piece of software is that. And so you’ve 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…

[01:26:02.07] So what’s crazy is if you look at auth, it’s like a 10, 10+ billion dollar industry; tens of billions of dollar industry. But if you look at payments, and you look at commerce, that’s a multi-trillion dollar industry. It’s like a whole other scale. And so the way I see it is that our billing products will become the breadwinner; not overnight, but decently quickly, within a couple of years, at Clerk. And we’ll 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’ve got a few more minutes to chat, about three-ish from my examination of the clock here… What else is left unsaid? What’s the next big idea? Can you tease your next big thing?

Yeah. So I’m working on something - and when I say that, I mean that very loosely… Every week, I get like an hour. It’ll slow down soon for me, after launch and 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, our 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 a way for designers - and engineers too, but mostly designers - to build and maintain components. 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. And since that’s 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 DevMode. And the idea of DevMode 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 DevMode 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 DevMode. They would just be the same.

Figma’s canvas is not a DOM. It is a giant WebGL thing. 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, that and the other thing, just to try to like match the DOM… [laughs] And so what Opacity is is a canvas that is the DOM. And you drag and drop, just like Figma, you build boxes… And the boxes that you build and the inputs that you put in there, everything is all actually just DOM.

[01:30:09.28] 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… But the thing is, everything that you’re doing is actually code. And so the export of Opacity is an 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, 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, when did it break, how did it break. You just destroy everything just by one click. And there’s no rollbacks, nothing. 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. And 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 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 an - an actual checkout is the name of the component, which is really a wrapper around the checkout component, and it has all your business logic in it. And maybe you really just use the actual checkout component throughout your codebase. So you can attach these other props to it. But that’s up to you. That’s however you want to do it. We just care about the look and the feel, and also some of the eventing. There’s events built in, so you can have click events, have hover events, all that stuff, that is just not going to change. Maybe you want a hook for the click event, and we give you a way to do that.

So it’s the idea of like if you were to build actual products visually, this would be the ideal way to do it, and that’s what Opacity is.

Hmm… Eventually a Figma killer, or a Figma acquisition? 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.

Cashflow.

Yeah. A cashflow company. I’m not saying we would never sell. I’m not saying that whatsoever. But I don’t think it would be a Figma killer and 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. That’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?

Mm-hm.

[01:34:02.11] So you see your components visually, and you can see the props, and 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 mess with them. So when you think about it that way, that’s what we’re building. And 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 here it is all visually.” What’s crazy is this product doesn’t exist anywhere. Yet it’s the thing that everyone would want. So it’s cool.

So all you’ve got to do is get more random hours over the next however long to do that.

Yeah.

Well, 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 from the outside looking into your world, that’s how it seems. It’ll happen.

You’ve got to add an extra F in there. It comes to fruition and failure. That’s usually what happens. [laughs]

Ah, yes, yes. Well, I mean, there isn’t a sweet unless you’ve got some bitter, right? The bitter is never as bitter unless you’ve tasted the sweet.

Yup. Yup.

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 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 back in 2012…

Oh my gosh, man…

Yeah. So it’s been a while.

It has been a while, man.

And it’s always fun. It’s always fun.

Jared Erondu, me and you, The Industry…

Yup.

The Random Show…

Yeah.

The days, man. The days. And yet, we’ve never met face to face, I’ve never been to ValioCon, we’ve never shaken hands…

Yup. Dude, the internet’s crazy. You could do stuff like that.

Yeah.

You can 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 had learned or heard the phrase more frequently than I ever have before, called “What the crap.” That’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… I just don’t do it publicly a lot. You know, I stub my toe, I’m gonna say a bad word. I’m not gonna say “What the crap.”

[laughs]

But on a podcast, it’s “what the crap”, kind of thing.

Yup. Yup. Dude, I hear you. I hear you. Yeah, it’s good. My kids now are old and grown… Almost all of them are teenagers now, and you’ve 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 gear is dad or mom gear. Like, wherever they’re going, I’m going that direction.”

Yeah, yeah.

It has been fun, Drew. Thank you so much for sharing your journey again, and getting into some details, and we’ll see about getting you back on, man.

Yeah, dude. It’s been great. Thanks again for having me, and we’ll chat later.

Alright, man.