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**Adam Stacoviak:** Yeah. What are some hard beliefs that you would say you have? |
**Drew Wilson:** 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 buy... |
**Adam Stacoviak:** \[18:15\] Your hard observation. |
**Drew Wilson:** That was my hard observation, so now my hard belief... |
**Adam Stacoviak:** Okay. I'm down. Take me there. |
**Drew Wilson:** 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 ... |
**Adam Stacoviak:** Right. |
**Drew Wilson:** 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 th... |
**Adam Stacoviak:** Wow... Okay, so -- |
**Drew Wilson:** There's my hard belief. \[laughs\] |
**Adam Stacoviak:** ...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? |
**Drew Wilson:** 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 organizat... |
**Adam Stacoviak:** Hah! |
**Drew Wilson:** \[22:08\] 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 ... |
**Adam Stacoviak:** Yeah... |
**Drew Wilson:** 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**: \[22:52\] |
**Adam Stacoviak:** 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. |
**Drew Wilson:** Yeah, let's take a look at these people. \[laughs\] |
**Adam Stacoviak:** 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. |
**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 myse... |
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 ... |
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. |
**Adam Stacoviak:** 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 th... |
**Drew Wilson:** Yeah. |
**Adam Stacoviak:** I mean, everything is -- how do you just do everything, Drew? How are you a renaissance person? |
**Drew Wilson:** 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. |
**Adam Stacoviak:** \[unintelligible 00:29:28.16\] |
**Drew Wilson:** Before there was layers. |
**Adam Stacoviak:** Oh, before there was layers... Oh, my gosh. |
**Drew Wilson:** Yeah. Can you imagine that? \[laughs\] |
**Adam Stacoviak:** 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. |
**Drew Wilson:** Yeah. |
**Adam Stacoviak:** You're blowing my mind here. |
**Drew Wilson:** \[29:48\] 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 st... |
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?... |
**Adam Stacoviak:** 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 i... |
**Drew Wilson:** 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. ... |
**Adam Stacoviak:** \[34:20\] Really? |
**Drew Wilson:** Yeah. |
**Adam Stacoviak:** 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...? |
**Drew Wilson:** 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 ... |
**Adam Stacoviak:** What's enormous? |
**Drew Wilson:** 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 r... |
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 s... |
**Adam Stacoviak:** 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. |
**Drew Wilson:** 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 sal... |
\[38:24\] 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... |
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. |
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