Drew Wilson

Yo! Podcast - Published 31 Mar 2023

Drew Wilson (@drewwilson) is is an accomplished designer, developer and entrepreneur with a prolific portfolio of online projects. In 2014 he founded payment startup Plasso which was later acquired by GoDaddy. Drew now works on his new venture Logical to help startups visually build and launch web services. We rap about AI disrupting the film industry, surfing with beefy sharks, why Letter Banking closed down, film vs web, his passion project Ryte and exactly what angel investors are looking for in pitch decks.


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Conversation Topics:

  • 01:17 Surfing or Legoland
  • 02:36 Road trip across 48 United States
  • 03:42 Sharks vs Orcas
  • 05:34 Intermission: Overrated, Underrated
  • 06:53 What is Logical all about?
  • 11:15 Sponsor: Lemon Squeezy
  • 12:04 How important is it to distill your idea down into a one liner for potential investors?
  • 13:14 If you can’t narrow your idea to a tagline, is it fair to say you aren’t focused enough on a niche to launch?
  • 14:18 What is essential to include in a deck for potential investors? (watch clip)
  • 16:47 Logical: will it cater for cached layers?
  • 18:27 Logical: authentication types
  • 19:37 Logical: team members
  • 20:16 Logical: Any investors?
  • 21:00 Intermission: No Context
  • 22:05 Film vs web
  • 23:13 If your Plasso exit was hypothetically 100x – what are you funding next?
  • 26:15 Sonic movie success
  • 27:22 Logan, one of his favourite movies
  • 27:50 Next Guest Cameo: Matthew Smith aka Whale
  • 28:26 Early film projects
  • 29:25 Is there an urge to fix something in film industry or do you want to make great stories?
  • 31:04 Waterbreak: AJKLN
  • 31:20 Will AI disrupt film?
  • 36:00 Letter Banking: What happened?
  • 38:35 Letter Banking:In hindsight do you think there were indicators?
  • 39:40 Letter Banking: Could you not replace the Series A investor?
  • 43:35 Letter Banking: What is the silver lining?
  • 45:15 Is Logical a breath of fresh air after a banking startup?
  • 47:08 Yo! Soundtrack on Spotify
  • 47:37 Do you think startups are missing an opportunity for video to amplify their marketing efforts?
  • 50:27 What is Ryte? Is it danger zone working dual with Logical?
  • 55:00 Next Guest Cameo: Michael Riddering
  • 55:14 Ryte: Are you breaking through some engineering feat that hasn’t been built before?
  • 55:40 Ryte: Do you build this to solve your own problems or to be acquired?
  • 56:15 AI: What advice do you have for listeners scared of upcoming AI landscape?


Bonus Episode Content:

Drew and I were both born in August 1983.

He recorded this interview by talking to me on his home TV.

Behind-the-scenes clip editing in the Jaws soundbites:

YouTube clip asking Drew what investors look for in pitch decks:

Watch the short clip →


Transcription:

Rob:

Yo, Drew. Welcome to the show, my man.

Drew:

Yo, how’s it going, everybody?

Rob:

If I was in your hometown Carlsbad, California, would I find Drew surfing Carlsbad Cliffs, training for the Carlsbad Triathlon, or hanging with his wife and three kids at Legoland?

Drew:

Probably the latter, to be honest. I mean, you asked me some years ago, it would have been in the surf, but you get three kids, they get older, all your time is spent there. So that’s where all my time is spent.

Rob:

Dude, I can’t speak, man. I’m on a 10th of the time when I was a grown dude, that’s all I did surf before school and after school.

Drew:

Yeah, I mean, when I first moved down to California, I didn’t know a soul, and I spent most of my time in the water. I literally would go out multiple times a day; I would eat lunch on the beach. I would just surf. It was great.

Rob:

My mom used to drop me at the beach, and we used to have a coin, it was five rand. I don’t know what the equivalent is to dollars; it’s like 30 cents, but I used to have a five rand in my Surfboard Leash, and that used to buy me a chip roll and an ice cream, and I spent 8 hours at the beach.

Drew:

Dude, what is a chip roll?

Rob:

It’s like French fries, but sloppy.

Drew:

Oh.

Rob:

And then in a roll with tomato sauce on.

Drew:

Okay, so in Canada, they call that Poutine.

Rob:

That’s new to me.

Drew:

That’s what they call it in Canada. We don’t really have it in the US. I mean, Poutine exists here, but it’s not a big thing.

Rob:

So you missioned around all 48 lower states, working remotely out of RV with your family for about a year. You got to sample most of the United States to all roads lead back to Carlsbad?

Drew:

For me, yes, but not for everybody. I think what’s really cool about the US is the diversity among the states is massive, and there’s only a few states that kind of have it all. California is one of those, but for me, yeah, southern California, specifically below LA, is where it’s at. But every place in the US is super cool for its own reason, and I can understand why certain people want to live here versus there or wherever, but yeah, it’s an amazing place, and I had a blast doing that trip and can’t wait to do it again.

Rob:

Amazing. I need to come to the States, and you need to come to Africa.

Drew:

Yeah, dude, I think about all the time, I’m going to go to South Africa. I’m going to hook up with you.

Rob:

We’re going to hang out.

Drew:

The only thing I won’t do is, I don’t know if I’ll go surfing, because of all the great white sharks.

Rob:

Dude, I know this sounds like it’s made up, but the Orcas came in, in their little pack and they took out all our great they cleaned out our great white sharks.

Drew:

What are we talking here? What year?

Rob:

This happened about two years ago. So I’ve been surfing 25 years, and my whole life I’ve been terrified of great white sharks. I mean, I’ve seen them, I don’t hate them, but it’s like they’re turf. And in the last two years, these great white sharks just started washing up on the beach without livers They just perfectly pierce and eat the liver. We describe it as like, eating the last little bit of a Cornetto, and then they throw away the ice cream.

Drew:

Dude, what’s a Cornetto?

Rob:

It’s like an ice cream with a little chocolate delicious end.

Drew:

Oh, okay.

Rob:

It’s like you’re buying an ice cream and then biting off the bottom and then throwing it in the bin. They just eat the liver.

Drew:

Dude, that’s wild, because you look at an Orca, and yes, they’re bigger than great whites. And I think in South Africa, the great whites are big, but they’re not as big as the ones in San Francisco. Those are like the big beefy ones.

Rob:

Pretty big, dude.

Drew:

But still, they’re probably not that much different in size in the Orca. Eating a great white? That’s insane, how do they even do it?

Rob:

Great whites, nothing on Orca. Yeah, so they’re just the apex predator. So it’s been weird for us because here we are, normally super scared and all the surf spots that are dodgy are now free game.

Drew:

I don’t know, man. There’s got to be some great whites that are holding out.

Rob:

Dude, it’s all cycles, they’ll come back. They’ll come back but seriously, every time there’s a breather, like another shock just gets nailed. It’s crazy.

Drew:

That’s crazy. Yeah, around here, we don’t have the Orca support. Our government didn’t do a special deal with the Orca population. Okay, let’s get right into a fun intermission, I like to call it “overrated”, “underrated”. I’m going to give you a topic, a brand, a person, and all you need to do is quick fire it back a reply saying; if you think it’s ‘overrated’, ‘underrated’, or ‘properly rated’, you got it. Sweet.

Rob:

– Marvel comic films.

Drew:

– Oh gosh, dude, you can’t put a rating on it. So good, so we’ll go underrated because there’s a soap.

Rob:

– Rob Machado.

Drew:

– He is in the surfing world, maybe properly rated. His kids go to the same school my kids go to.

Rob:

– The Carlsbad Miniature Engineering Museum.

Drew:

– (*Laughs*) I have never even been there, so I don’t know. We’ll give that a properly rated.

Rob:

– Online privacy

Drew:

– Underrated, I think too many companies don’t put enough emphasis on that.

Rob:

– RDio music streaming service.

Drew:

– That was definitely underrated.

Rob:

– Soundcloud.

Drew:

-Oh, man, I guess I’ll say properly rated.

Rob:

– Blink-182

Drew:

– Underrated.

Rob:

– Photoshop.

Drew:

– Properly rated.

Rob:

– Sketch.

Drew:

– Properly rated.

Rob:

– Figma.

Drew:

– Properly rated.

Rob:

– ChatGPT

Drew:

– Very underrated.

Rob:

– YouTube

Drew:

– Underrated.

Rob:

– And lastly, Silicon Valley.

Drew:

– Overrated.

Rob:

Okay, before we discuss the wind down of Letter Banking, let’s talk about what you’re working on now, Logical, from what I understand, it’s a SaaS to help save development time as you visually build and launch web services from within one UI. Can you tell us a bit more what it’s about?

Drew:

Starting with kind of the why, will help with telling the story and the reason, I started logical is because as I was winding down letter, I was trying to think of, what am I going to do next? I’d never been in the position where I didn’t know, what I was going to be doing? So it was a first for me. And so I spun up some old projects, hopped into the servers was updating, the systems that were in there, and keys, and as I was updating stuff, I was like, this is terrible. I can’t stand it, I don’t like doing it, I don’t ever want to do it again, and yet I know how to do it. I just don’t want to do it. I’m not actually writing the code, that’s going to make a difference in my app. I’m just standing up the infrastructure, and it’s super time consuming and then once you finish it, you have to still maintain it. So I was like, okay, this is probably what I should do, I should probably fix this problem that I have here.

Drew:

And I had started a project years ago, like 15 years ago, kind of in that same vein, but never fully finished it and so I decided, all right, it’s been pretty cool to see these tools like Framer and Sigma, where they’ve got like this, operational component to it. Where you’re actually doing something, and they’ve got this community component to it, where you’re actually sharing stuff, pretty easily all within the same app. And it helps people who aren’t as proficient at the operating side, be proficient because they got all the stuff ready to rock and roll for them and so I was like, that is what the back end world needs. It’s full of fantastic infrastructure engineers, back end engineers, people who enjoy pulling these pieces together, but there are even more folks who have to do it, that don’t want or like to do it. And there are even more folks that need an API or a back end system, but don’t have any idea how to go about it and have to pay someone a bunch of money and have to. Wow, I stick at some designer saying, Oh, this person’s a great engineer. I’m like, you have no way to know if someone’s a good engineer, you just go off of what you feel, there’s no way you could know. And it’s different design, you can know if someone’s good just by what you look at but in engineering you have to know, to be able to know.

Drew:

So there’s a ton of people that could benefit from an easy way to build a back end. Not only that, today in all the enterprises across the world, there are multiple teams working and building back ends. New ones, maintaining old ones, et cetera. In terms of who’s doing what on those systems, it’s very hard to audit, there’s no audit trail. So another big piece of logical, besides solving the problem of being able to easily and visually build and maintain back ends, is going to be this idea of a Git based UI, where normally when you’re in an app and you turn something on, you toggle switch, you hit save it, saves it in a database somewhere. You have no idea, who turned that switch on if you look back a year. But in logical, the entire UI is going to be Git based, so every toggle switch you do thing you type into an input field, it’s all going to be commits behind the scenes and then you’re actually committing to a repo and so the entire UI itself is fully auditable. And from a management perspective; it would be a dream to know, who’s been doing what because ultimately, I believe in this thing that many other people do called infrastructure as code, where your infrastructure is all written as code and then that code has a bunch of code behind it that goes and spins up this thing, spins down that thing, puts these two things together, but you’re writing it as code instead of clicking around the UI. So you’re getting the best of both worlds. You’d be able to click around the UI, but it’s also all get based in using code, so that’s what logical is. That’s kind of the goal is to take this world of back end development and web services and bring it to the Figma, Framer world where you’re just dealing with UI, which will be kind of cool.

Rob:

Amazing. So in your pitch deck to raise capital, which I’ll link to in the show notes, you phrase logical as the framer for back end systems.How important is it to distill your idea down into a one liner for potential investors?

Drew:

I think the time you would use that, is in like a deck I’m sending. The purpose of the deck is to get someone interested enough to talk to you, it’s not to tell them everything about what you’re doing, it’s to pip their interest. So that you can tell them everything about what you’re doing and I think I have that Framer for back ends or something on the very first page. And the reason for that and it’s underneath the better description, the two sentence description of what it is and the reason for that is, so before they even have to flip to another page, there’s something in their mind that kind of triggers, okay, it’s kind of like this and from that, it kind of sets the tone because this one line distillation, if you can’t distill what you’re doing into like one line,(then you should) figure out how you can distill into one line because that’s going to be a really compelling way to like, an informative way to set the scene for your longer talk with that.

Rob:

My next question is, if you can’t narrow your idea down to a tagline, would you say it’s fair that you aren’t focused enough to a niche to launch?

Drew:

I would say that you don’t understand what you’re doing enough. If you can’t distill something down into, like, ideally you distill it down into one or two sentences because then you get a little more description, but anything longer than that, not one to two long sentences, like one to two short sentences. If you can’t get it that short, then you probably don’t understand the problem and your solution enough, and if you can’t get it down into a single little phrase, literally, like visual back-end development or something like that, if you can’t get into a few words, then you probably don’t understand what you’re doing enough and that’s not a bad thing. It just means, hey, take the time to understand what you’re doing. A lot of people, a lot of builders want to boil the ocean. They want to do all the things, and that’s not good.

Rob:

Yeah. If you can’t explain it to an investor who’s one-on-one with you, how are you going to explain it in your landing page to your audience, who’s visiting for the first time, especially with less attention? So in your deck, you have a crystal-clear SWOT analysis diagram that pinpoints where logical sits within the market. You’re on your X axis, you talk about the front end to the back end, and the Y axis is ease of use, from easy to difficult. Okay, It’s brilliant to see the competition mapped out. My question is having a clear SWOT analysis and a strong tagline seems to be vital for pitch decks. What else is essential for investors?

Drew:

So ultimately, the investor is going to want to know, how can they multiply their dollars significantly? Right? They’re not looking for small wins, they’re looking for big wins because the nature of startups is that most of them die. So if an investor is going to try to make money in startups, they have to have the rocket ships, otherwise it’s just charity, right? So for them, they need to know how you’re going to make money and so the important points for them are going to be not totally the idea. Most investors, when they go to raise money themselves from their LPs, they’re promising their LPs, we’re going to invest in this space or that space, they have what’s called their thesis and they have to not always, but usually they have to stick to their thesis. If they’re not sticking to their thesis, then what they sold to that LP isn’t really real, right? We’re going to invest in medical tech. If they invest in a vacuum startup, then that’s not the same thing, right? The idea isn’t as huge of a deal in your deck because you’re only going to be talking to investors that want to invest in your idea anyway, so you’re not going to be talking to these investors that don’t want to invest in what you’re doing. So the idea stuff not a huge, huge deal. What is a huge deal is your team, getting the right team with the right experience because the investor is all about de risking things in the beginning and if you are a first time founder, you’re a high risk. If you’re a founder, has done a number of things but never a successful one, you’re a higher risk. So getting the right team together is a big one. Investors like to say, we follow the founder and so your founding team is big. The other piece is showing the market and how big is and why your solution is going to be a compelling offering in that market. So, I think if you get the team and you are able to describe why what you’re building is needed and that your market is big enough for venture size returns, those are the important pieces.

Rob:

I got a question here from Calvin from interact list. Question – Hey guys, Kelvin here from interact list. The performance can be improved and database requests reduced by introducing a cache layer, something like upstash. Is this something logical caters for?

Drew:

Oh, 100%. Yeah. The idea with logical is really, and this will be a tagline on the marketing website, because the marketing website is for our audience, our customers, which are developers, and the pitch deck is for investors. But on the marketing website, the tagline that I’ll have is best practices as a service. So the idea here is that anything you as a developer could think of that’s going to be the best way to do something, that’s what logical is going to do. The idea is that we build a brand that you trust will be building the best way to do stuff, and we’re not going to invent the best way to do stuff, we’re going to use what is the best way to do. Now there’ll be things that we invent, I’m sure the idea is to use best practices and make that a service. So, yes, we will be having cache layers in the database. The idea is that when you sign up for logical, you set up your data collections, this is really the data model. So in an API, when you request your users, you get back a bunch of fields about a user and the database actually, the setup for the database oftentimes looks pretty similar to what the API returns. So you’ll set up your collections, which will then create an API instantly, and also create a database instantly, and it’ll create a database that’s fully cache backed up, et cetera, et cetera, et cetera. You don’t got to worry about that stuff. It’ll be distributed database across a bunch of regions. That’s the whole point of logic is that this is something that you could start and scale with that will be built on best practices.

Rob:

Good stuff. So we got another question here from James. Question – The logical deck mentions SSO support. Can you shed some light on what types of authentication will be supported?

Drew:

Probably eventually most everything kind of the idea with Logical is that, we want to make everything visual and to start with we’re going to have an VP and so the auth is probably going to be on everybody else to disband it themselves. But we will have a community feature and if someone wants to build like an authentication system and build in logical the collection fields and all the setup that needs to go for it or to build that, they can make that available to the rest of the community. Sort of like you would in Figma, when you make a UI design template available for the community. That’s kind of our plan is to kind of leave it up to the community. That happens right now on GitHub. GitHub you’re getting code, that you would then need to put into your actual code and deploy it, customize it, config it, that kind of stuff. The idea here is it’s already done, no config, just click the button and there it stood up on your system. So taking it like another step further. So eventually I hope to have all the things, but to start with, there will be none.

Rob:

Roadmap. So in the deck you teased a team of eight people. Were those placeholders or you already deep in the team slack?

Drew:

No, those are not placeholders, those are real people. Real people working on it. And what’s crazy is that I think it’s my PR, my personal record. Came up with the idea, did the branding, built the deck, built the app from a design perspective and built the team in like two weeks. And then we’ll be raising money maybe next week, we’ll see. But yeah, fastest for me, I didn’t intend it to be like super quick, it just kind of all came together. All the right people that I wanted to work on it a lot of them from letter.

Rob:

Any investors on board already?

Drew:

Yes, one who is on board? No money sent yet because I’m not quite there yet. I already have a bank account set up yet because that process of creating the legal entity, takes longer than me creating all this stuff.

Rob:

What do you use? Stripe Atlas. Delaware?

Drew:

It’s Delaware. C Corp operating has a foreign corporation in California. Yes, standard, but I use Quiry for everything. Clerky.com

Rob:

They’re used by a lot of YC folks because I think they went through YC, but back in like 2010 or 2012, like super early YC, and I’ve been using them for everything.

Rob:

Okay, let’s break into a second intermission. It’s called no context. Simply shoot back either of the two options I give you, no context given, no explanation needed. You got it…

Rob:

– Myspace or Pure volume?

Drew:

– Oh, pure volume.

Rob:

– Green Day or the Offspring.

Drew:

– Green Day.

Rob:

– NOFX or pennywise.

Drew:

– NOFX.

Rob:

– The Endless Summer, One or two?

Drew:

-One.

Rob:

– Quads or thrusters?

Drew:

– Go quad.

Rob:

– Front side air reverse or backside tube?

Drew:

– Backside tube.

Rob:

– Martin Scorsese or Christopher Nolan?

Drew:

– Man, you got the hard ones. Scorsese

Rob:

– Hans Zimmer or Howard Shore?

Drew:

– Zimmer.

Rob:

– Final Cut Pro or Adobe Premiere Pro.

Drew:

– Final cut.

Rob:

-Ghost or substack?

Drew:

– Ghost.

Rob:

– Lemon Squeezy or Gumroad?

Drew:

– Lemon Squeezy.

Rob:

– Open source or recurring revenue?

Drew:

– Open source.

Rob:

– And lastly IMDb or Rotten Tomatoes.

Drew:

– IMDb.

Rob:

After a deep, deep dig, I discovered you have an IMDb profile, as an art director for a surf film back in 2010.

Drew:

Dude, it was pretty rad.

Rob:

Is there a small part of you that wishes you steered more towards film than web?

Drew:

It’s a tough one because in my mind, I will be doing movies next and the whole point of this tech thing is to make enough money, so I can make movies. And as a matter of fact, when I was in on that year long trip in the RV, I was very, very close. To just throwing in the towel on the tech thing and then just trying to become an actor or get into film in some way. And I decided because I was stuck in RV, it’s not like I could immediately make that change and so after a couple of months, I decided that’s probably really dumb because there’s way more people try to be an actor and I’ve got nothing special whereas in the tech side, I’ve already built up a lot of experience and know-how and skill and I can actually do something. And so that’s when I decided I’m going to stop the bootstrapping and I’m going to try for the first time to raise money. I didn’t know anybody with money, didn’t know any investors, nothing like that but I decided I’ll try that. And that’s when I raised money for Plasso.

Rob:

This is such a good lead to my next one. So I’ve seen you joke online that you want to make films, but I mean, you’ve just told us straight up, and I want to freeze style. September 2018, you sold Plasso to GoDaddy. You raised just under 1.2 million, you sold assuming for more okay, hypothetically, you got 100x, what are you funding next? It’s not letter banking, right?

Drew:

So there is something that I want to make, and I’ve told many people, but I’ve never really said it publicly. There’s a number of films that I want to make. I’ve written outlines and partial scripts and stuff like that, and most of them are Sci-Fi. But there is one that will be hopefully my life’s work. It’s a very risky thing to say that. I mean, I literally want to do it. I’m not like joking around or anything. I literally want to make this and the stage is somewhat being set. It’s a Nintendo franchise, it’s called Zelda. It’s one of my favorite things ever created. Absolutely love Zelda and everything about it. The mythology is huge and could easily sustain a marvel universe sized franchise but to start with a trilogy like a lord of the rings live action film, that is the story of Zelda. And there’s so many stories to pick from. It’s an incredible universe, and I would love for it to be explored in a live action format, but Nintendo has guarded their franchises extremely well because of the failure of Mario. The first one in the 90s, that was horrid.

Rob:

Oh man, I actually totally forgot about that film.

Drew:

Yeah and they had a Mario cartoon. They had a couple different series of Mario cartoons in the early 90s and then they also had a Zelda franchise, a cartoon. And it’s awful. It is so incredibly bad, it’s hard to imagine how bad it is, but you should look it up.

Rob:

Is there a translation lost where they’re based in Japan?

Drew:

Yes. The Nintendo franchises are massive in America, and so they wanted to capitalize on it. And I’m sure some studio went to them and be like, Yo, American kids love cartoons, make a cartoon and they’re like, okay, fine. We’ll make some money, but we want it to be this way, is what Nintendo is saying. And the Americans are like, no, this is what kids like, believe me. And it was just horrible, it was absolutely horrible, horrible, horrible, horrible. There’s no good thing about it at all. You should watch them on YouTube, they’re pretty great. Amazon has all the seasons, so you can watch. But so Nintendo has closely guarded their franchises from getting desecrated again by Hollywood. but with the Mario movie coming out, the CGI Mario movie, it can make sense. Mario would be not a great choice for a live action, it’s a cartoon character in a very cartoony sort of world the interactions that Mario has with other characters are always kind of tongue in cheek and the way that he moves everything’s very cartoony. Whereas Zelda is not that way at all. It’s a way more serious franchise, and the characters interact in a serious manner and the physics everything are way more closely aligned with reality, than they are in Mario. And so it would be a fantastic film, if it were to be made and so I hope one day to somehow be involved in the making of the Zelda trilogy.

Rob:

Dude, incredible. Thank you for sharing that. So who’s our lead currently for Zelda?

Drew:

Because by the time we actually go to make it, all those people will be 75 years old. I don’t know.

Rob:

But I mean, on the positive, that’s a legacy that’s going to outlive us. The brand is still super strong, man. How did the sonic movie do? I know that was a really risky adaption.

Drew:

Yeah, the sonic movie did good. I don’t think it blew away any records or anything like that, but it did good enough to make a second one. And sonic is aimed at, like, a younger audience and when they made the movie, they did the same thing. And Mario is obviously aimed at, like, G rated, PG rated audience. With the Zelda franchise, I would love to do, at minimum, a PG 13 kind of take on it. And so it’d be a very different sort of movie and franchise, it would be very fun and you could do the same sort of things they do in the marvel movies. I mean, one of my favorite films, top two films of all time is Logan, which is the wolverine story, and I love what James Mangold did there. He made it like a 70s film and such a good job, that film is incredible and you could do that same. So you could do spin offs like that with different characters from the Zelda franchise. I mean, Nintendo sitting on some go red there. People love that medieval kind of feel.

Rob:

I think it was GaryVee kept talking about the Nintendo franchise. They’re just snoozing on it. He’s just saying, there’s so much to do. Man, I could go deep on films here. Like, I watched all three lord of the rings, extended versions back to back, dang in the garage with speakers. I was, like, 12 hours or so. I wouldn’t recommend it.

Drew:

Yeah. When I was younger, like you were pointing out, I worked at a surf film company. We made a number of films, including the documentary of Bethany Hamilton, which then got picked up and turned into a feature film, a theatrical release. But the movie that I was the art director on, one of the movies, I was the art director on actually got picked up by Sony. Walking on Water got picked up by Sony and then got picked up, they distributed through Netflix, so it was on early Netflix. Back when you could still get DVDs and they had the online component. It was on Netflix for like, five, six years or something like that. It’s no longer there and then I remember walking into a grocery store by my house to get groceries, and in the US there’s grocery stores often will have DVDs in the store. And there had all the checkout stands was the movie that I made, the cover I designed, all that kind of stuff was right there.

Rob:

That’s pretty cool. What a moment.

Rob:

So when reflecting on your projects, you seem to be frustrated with a certain way things are done, and it’s kind of followed by an urge to build a solution for it. Do you have an urge to fix something in the film industry, or do you simply want to create great stories?

Drew:

Yeah, I think there is a lot of efficiencies to be made in the film industry, but the film industry, even more so than tech is feast or famine. Either you are a big movie and a big franchise, or you are not. And there’s not a lot of middle ground. In tech there’s a lot of middle ground, you could run a successful business, you could even bootstrap a successful business and do well. That’s not really the case in film, and it’s not set up that way. I think the standard deal for Netflix for an Indie film is like 60 grand. They give you 60 grand, they take the rights. So stuff like that just makes it even worse. So, that being said, the folks that are making movies, these movies don’t have very big budgets, and so it would be difficult to build in that space, unless you’re building for the high budget films and there’s very few of those customers, right? Very few of those customers. So I think it’s a very difficult space to build in because of the huge difference between, what a successful film is and what every other film is in terms of revenue and budget. So I don’t have a desire to build anything from a technology perspective in that space. What I really want to do is I want to make a movie, that has the same sort of impact movies have had on me. Movies are a huge deal to me and always have been since I was a kid. And I just want to be a part of that. It’s really all it is.

Rob:

Will AI disrupt film?

Drew:

Oh, yeah, absolutely. I think it already is; it’s going to democratize it even more. And I think there’s an opportunity for a startup, if Unity doesn’t do this themselves. I was just talking to someone in Twitter DMs about this the other day, is that Unity, or Unreal Engine rather, is an incredible piece of software. It gives us these hyper realistic real-time visuals, and they use that in The Mandalorian, they use it in films all the time now to build these virtual sets. It’s just going to get better over time with the release of, I think, Unreal Engine 5.3 or 5.2 that just came out. It’s insane what they can do. To run Unreal, you need a bunch of really well powered computers and servers, right? To render this stuff. And so if someone just kits an AWS account and puts Unreal Engine on these things and then builds a SaaS where you can render things in the cloud with Unreal and then build an API around Unreal’s methods and functions, so you can make an API request to those servers, and it will do something. So really, the only thing you’re building is an API. You can plug that into chat GPT and chat GPT plugin, and then someone could say, Hey, here’s a story I’ve got. They can just do the prompt how they normally would with any video thing, and then it can render it all out in Unreal Engine and save it down as a video file, and there you go. And someone’s going to do that, maybe, hopefully, for unreal’s sake, they do that because that would make them lot of money, but someone will do that when that sort of thing happens. It’ll happen with other stuff, too, but when that sort of thing happens, the idea of this huge budget production to get something, what we now consider theatrical quality, the cost basis is going to drop to the floor. I mean, to the floor, it’ll be pennies, it’ll be so cheap to make this stuff, and it’ll be more about storytelling and creativity that’s always going to be there. But actually, there’s his name’s James, I can’t remember his last name, but subtext this is app, and he has this app for screenwriters. And early on, he was early on the AI stuff, he started adding AI, so that way you could ask AI to, Hey, can you flesh out this character a little more? Because his app is set up so you do screenwriting, they separate out all the characters in separate blocks and so you can go in and fill out the whole backstory of a character, this character, that character. Then you can tell AI here’s these two characters, they’re meeting for the first time, what you think would happen. And it can tell you some scenarios and you can use that and run with it. So he’s using AI already, and he just added in the latest Chat GPT stuff with Chat GPT -4 and the new APIs. And that stuff is going to take storytelling to a whole new level in terms of efficiency and getting stuff done better, and eliminating writer’s block. A lot of the struggles that writers currently have will be helped by AI, thereby reducing the cost of writing even further. So I think films are going to be made on a fraction, of a fraction of the budget that they’re made with now. I mean, you’re still going to have to pay just as much for advertising, right? It’s usually one to one, a film’s budget, they spend that same amount in advertising. So if it costs 100 million to make, they spend 100 million in advertising. Well, so you still have to pay that, but the cost to make the movie is going to go down. You get AI actors or you get stand-in actors that you replace with someone in AI. So Leonardo DiCaprio is like, I’m going to retire from acting, and he’s going to go 3D scan himself. He would never do this, but he would go 3D scan himself, his body, his voice, and he’s like, Yes, you can click this button to license me in your film, and I’ll make just as much money as I would if I acted in your film, but I’m never going to show up, I’m never going to actually act in your film. You pay someone else is a standard whose face will never be seen, and they act for me.

Rob:

And that kind of crap could happen. There’s, like, an AI agency, Leo signs up you get to lease him. Just saying stuff for adverts.

Drew:

Imagine that. Like Leo’s in like, every freaking film, and he makes a ton more money because of that.

Rob:

Wow. That was rad. I also can see you, like, rapping about film more than you do about tech. No, I’m kidding but you were stuck. Circle back to letter banking, okay. You mentioned on Twitter you spent four years nonstop building, coding, designing, complaining, partnering, raising money, and now you’re winding down with a business as you lost a Series A investor. What exactly happened?

Drew:

Knife to the heart, man. Don’t bring it up. The worst part about Letters shutting down is that I have to go back to Chase Bank. Oh, it’s so painful. I’ve never tried so hard to do something and then failed. Previously, I was what would be called a maker or bootstrapper, and you do a lot of things at once, and if one fails, it’s a bummer, but it’s not a huge deal because you got these other things going. Whereas I decided kind of like I did with Plasso, but with Plasso, it was a life-changing success, whereas with Letter, it was not. Yeah, I mean, ultimately, what happened is we had partnered with a capital partner, someone who was providing capital for our lending product, because we launched a lending product, where we built all the underwriting in-house in all automatic. So that way, there was no humans involved, which is very unique and not something that exists today. There are other startups that will make the process of collecting your underwriting data easy, make it easy to upload this, connect to that, but ultimately that gets sent to a bank or a capital partner and a human reviews that. In our case, it was fully automated, so you could get instant lending, which is pretty unique, and we launched that with that capital partner, in a very niche market. And they wanted to invest in us, but they were raising, like, this massive fund, like multibillion-dollar fund. And so that took a little while, that was finished. They’re like, all right, we’re going to do this investment. And meanwhile, I’m sitting here self-funding the company, because it was very difficult to raise for Letter, the entire life of Letter, very difficult. And so I’m all right—well, just give it a little longer—and so we worked out terms, we came to an agreement, and it was going to be a great deal. They would have added a lot because there, a very well-known family office, and anyhow, came down to time to actually execute, move the money, sign, all that kind of stuff, and they pulled out last minute and kind of left us stranded where we were expecting this money at this time and it didn’t happen and I had burned up all the money that I could use on this, so we had to shut down.

Rob:

Okay, two things in hindsight, were there little indicators that this was going to fall through?

Drew:

Yeah. So when you’re raising money—I mean, I raised money from a lot of investors, I’m not kidding. I never stopped raising money for letter in those whole four years. I never had like a proper round where it’s like, okay, let’s raise a million bucks, and then it took us two months to get there, we got a million, we’re done. It was like I just kept raising the whole time. And so you get familiar with and also my experience with plastic, you get familiar with what it’s like when someone’s interested or pretending to be interested. We’re actually going to actually invest, and this person was going to actually invest, and then it got pulled for a really random reason, out of our control, and so the indicators all pointed to stick it out. It’s worth the risk, right? And it’s a risk when I’m starting a startup, it’s not like I’m getting a job somewhere, I’m taking a risk, so I have no ill will whatsoever towards those folks. They’re just doing what they thought was best for them and I took a risk and it didn’t pan out. That’s me, that’s on me. Not a big deal; that’s it.

Rob:

Is there no other series A investor, though. Does someone else not exist?

Drew:

There are plenty of other series A investors that exist, but series A investors are like seed investors, only they give you more money and so they don’t want a lot of risk. They want a proving company, usually with product-market fit, which we did not have at the time. And when they say, Okay, how much money do you have? And I say, well, I’m self-funding the company now. They’re like, all right, VCs are, and they’ll say this too. They’re not leaders, they are followers. The nature of VC is to follow, it is not to lead. They’re not making any industry, they are following founders in hopes of gold at the end of the runway. So the way that they work is if there’s a hot company, meaning other VCs are trying to get this company, I heard from this guy, heard from that guy, then they’ll want in. It is very difficult to find a lead investor, someone with conviction, unless you are literally proven. We’re making a ton of money, we’re growing a ton. That would be way easier, but even still, it’s going to be hard to find a lead investor because the nature of the VC is to follow, it is not to lead. So it’s difficult to lose a Series A and then say, hey, you’re a Series A investor we lost our series, they decided not to invest. Do you want to invest? No.

Rob:

I got you. I wonder how many people furb in the industry. Like a massive game of poker.

Drew:

Yeah, it is. I mean, VC is a gamble, it’s a risk. They learn to halt risk, but it means the same thing, gambling risk same thing. Yeah. The difficult piece with Series A, it gets even harder as you go forward, but with Series A, in a lot of cases, startups are still very new, very green. And a Series A investor is a tough place to be, I think it’s tougher than being a seed investor. Seed investors are easy because you’re dealing with smaller pools of capital. When a seed company wants to raise money, they’re like, I want to raise 1 to $5 million. And so for you to put 100 grand in, that’s a good portion of that $2 million. On the Series A side when you’re trying to raise ten, you know, maybe let’s say seven, sometimes 30, usually 70 to 20. When you’re raising in there, you’re not going to take $100,000 for an investor. Why would you do that? There’s no reason to take $100,000. It’s not going to get you anything. No other investor is going to be impressed by someone, oh, we raised money from this firm. How much did they put in? 100 grand? Oh, who cares? You got to raise larger dollar amount, and money is the same at a seed firm or at a Series A firm. It’s a lot of money. So if you’re going to cut out a $2 million check for half of a round to some founder, that’s a way bigger difference than cutting a $100,000 or $25,000 check. So there are much fewer series A investors, and as a founder, you go about it differently. When you’re raising a seed, you could just start taking angel checks, angel checks, angel checks, 30 angel checks, boom. Whole round done, easy peasy, long as squeezy, but if you’re raising a Series A, that’s not the way you do it. You got to go get a lead who will put in a lot of money, multiple millions of dollars, and then from there, you can go find another person to give you a big check, and another person maybe give you a smaller check. And those rounds are usually made up by a very small number of investors compared to a seed round, which can often be my seed round was just literally all angels. I didn’t have any firms ever.

Rob:

I want to say here, what advice would you give yourself if you’re starting over in this chapter? But what is the silver lining on all of this? You’ve got eight team members ready to go. You got some experience.

Drew:

I think there is a silver lining at everything. For me, it’s a bummer to not have made letters successful, but that’s it. There’s no other bummers. I mean, it sucks that I’ve lost a lot of my money, but I’m not on the streets or anything, and I am confident that I will be able to make an even bigger success in the future. You can’t win them all, right? You can’t win them all. You can’t start something and expect to win them all and so the bummer is not having made a success, but everything else is a silver lining. Like all the experience I got running a bank for four years, that’s insane. Hardly anybody has ever done that and so the deep knowledge I have on finance now when I went into Letter, I had no knowledge of finance that’s what I would tell people, I’m an outsider, I’m going to build something cool here. And then, having gone through it all and the kind of people that I got to pitch to and everything is freaking incredible. Because I was dealing in high net worth banking. So the kind of people that you meet in that world are super smart people that have done a lot and I don’t know, it was a great experience working with the team, building something awesome. It’s a highly regulated space so it’s a very different way to work, you can’t work fast in the sense that you could if you’re building a SaaS company. It just doesn’t work that way. Everything about it was great other than it not working out.

Rob:

Logical is going to be a breath fresh air now with the speed you can move.

Drew:

Yeah, it’s very different. Like at a bank, for example, a bank is regulated for one reason to make sure that they don’t go under, and so the reason for the regulators, like the OCC, regulates nationally chartered banks, banks that can operate across the nation. Then there are state chartered banks, and those states regulate them and they have different rules, the states and the OCC, but they’re largely the same. And the whole purpose for all those regulators to make sure that this bank, all the banks that they oversee do not go under because of bad investments, bad practices. A bank is a business, and it’s run by business people. And if those people, come up with stupid ideas of how to get customers or bad products that are going to be loss leaders, the regular is going to be like, No, you cannot do that because that is too risky. It will destabilize the nation. And so when you, as a startup want to work with an existing bank to build a new, cool product, The banks like, well, no, and we can’t do that. They might say, even though we think it’s a great idea and we want to do that, the OCC won’t let us do that, and we could say, oh, come on, just go talk to the OCC spend a year or two trying to get them to do it. And they’re like, no, it costs so much money for us to talk to the OCC and negotiate, and then if we get the thing done two years from now, then we try it out and see if it even works will it be worth our time? No. And so the way that a regulated system like that is set up is to not discourage innovation but discourage the innovator’s pace of working right where you’re used to working fast, moving fast. It is a hundred percent purposely designed to squash all that hectic, so it makes it very difficult.

Rob:

Second last question. In 2008, you dropped a pretty wild teaser video for the Fire Rift CMS Shout out under oath. Then you rolled out a bunch of pretty sweet promo videos and explained the videos for Plasso. Do you think startups are missing an opportunity for video to amplify their marketing efforts?

Drew:

I think so. People love watching the commercials that are on the Super Bowl, not because it’s going to be somewhat funny or anything like that. It’s because they’re going to be outlandish and they’re going to be crazy and it’s going to be funny to see them. They’re going to be not a normal commercial. If a startup is just going to build a normal commercial, there’s plenty of studios that will do that for you and I think a lot of startups do that and that’s great. I think they should because it looks good, it makes you look more professional, et cetera. But the outlandish idea isn’t tapped into very often by startups because it’s expensive. Especially now with YouTube and creators being so good there’s this idea of hey, it’s just going to get lost in the weeds, even if it is funny or outlandish. But I think it just adds another bit to your brand, if that’s what you want for your brand. Video is a great way to impress on people’s minds who you are, more so than reading text or scrolling down a page and seeing some stuff when you have that absolute focus from that video provides. When people watch a video, they’re not doing anything else, they’re just looking at your video and consuming both audio and visuals concepts. And so I think it’s a very underrated tool. I think people make use of video a lot, but they maybe make use of it in kind of the generic way and not necessarily taking the opportunity to make something sort of outlandish like that. I think the first comment on that fire of video from 24 years ago was, what in the world does this have to do with software? Yeah. And I was like, yeah, doesn’t really have anything to do with it, but that’s kind of the point. It’s fun. You just toss the brand in there, you make something cool looking with Under Oath on the soundtrack. But honestly, the truth is not everybody is creative enough to come up with something that would be compelling. They have an idea, like most content on the Internet, when people do content marketing, they’re like, oh, yeah, we got to make something, like, original and cool and they come out with something and it’s just, like, very generic. And that’s not what they intended. And even when they look at the result, they’re like, this is original and cool. The originality about it is the fact that it’s about their product that’s as original as it gets. Other than that, it’s just plain janed, the same way that everyone else did it. And you can’t use your product as the originality. I mean, that’s built in. You’re advertising your product, you have to have something else that’s original about the video.

Rob:

I was looking at your list of projects on your outdated website. There’s quite a few you haven’t mentioned, and one of them is the one you’re currently working on at Tandem with Logical, and it’s called Right. And you mentioned about creating accessories for Apple products. So, two part question why? And secondly, is that is a danger zone working in dual, or is it for inspiration?

Drew:

Yes. I love the fact that the description is very deceiving, the idea that we’re making cases for Apple devices because when people hear that, I’m sure everybody thinks of iPhones and iPads, but I’m actually thinking of something different. I’m thinking of computers. And what’s really cool about Apple is that they have extraordinarily good taste and design but the bummer also is they have one taste and one design. And it would be so cool to use your Apple Computer but have it look just as amazing, but with a different design flavor and have some variety in what’s sitting on your desk and that you look at every day. And that is the goal of Right is to make Apple Computers fresh, new, with really good design. So the reason I’m starting Right is because I think that should exist. The PC market is huge, but that’s really, like, techie and technotence, like, looking for RGB water coolers, that kind of stuff is not at all what I want to do. But I think that there should be some variety in Apple’s design language, and that will never happen from Apple, so it requires somebody else to come in and do something. And to date, I don’t think anybody else has done it. There are plenty of online renders of folks that have mocked it up, but nobody that’s actually made it and so I’ve been working on this for several months now and it’s new for me. I’ve always wanted to do something in the physical space and so we’re actually building something. And one of the things, the first product that we’re going to come out with is going to be pretty killer. It involves this arm that has to hold up a monitor. And what’s crazy is the forces that are involved in holding up a monitor and so if you have an Apple Cinema Display, what’s it called now? Oh, the XDR. The XDR is £17. But if you’re on an arm, the amount of force required is like 300 and something pounds to hold that up. So you need this intensely powerful arm with these massive springs or some other system to hold this thing up. So if you want to move it, you can move it. And so the challenge for us has been to build that, because to date, it has never been built. There are these, ergotron, arms that move up and around, but they’ve got this elbow on them that’s steel and so it’s a two jointed arm, but if you want to build a single jointed arm that could hold up something that heavy, that’s never been built before, I think Apple has the closest they’ve come is they built one for their iMac G four, which was the little dome with the floating monitor but that monitor is like £2. To build something for that is easy.

Rob:

What is that stand that they built that was so expensive?

Drew:

Yeah, they built expensive stands for their Cinema display, but the little arm thing is like three inches long. It just lives a little bit and so that’s why they made it so small, was because they’re like, we probably can’t figure this out within our budget. Right. Easy enough to do. And so what I set myself to is, figuring out how to make this arm and we finally come on a solution that we think will work that we’re currently prototyping right now. So I’m working on this with a buddy, Jeff Johnson, who’s a super fantastic physical engineer and has been in the space and is a CTO at his robotics company and has been in the space for 20 years doing this stuff. So the two of us are working on this and the stuff we have planned is going to be pretty great. I’m hoping to have, like, a coming soon website rolled out within the next month or two, once we kind of really know for sure that this design is going to be the one. And then I’ll be able to pump out all the because I’ve already built a website and I’ve already built out tons of stuff, but I haven’t been able to show anybody not 100% final yet. So once it is, we’ll be able to show people. So I’m very excited for this.

Rob:

Are you having to break through some sort of engineering feat that that hasn’t been built before?

Drew:

Yes, that is that is what we’re having to do, which is unfortunate.

Rob:

Okay, so you’re inventing…

Drew:

Yeah. This first design that I picked, I didn’t realize it was going to be this difficult. Nor did Jeff when we started. There are a couple other designs that I want to do like Piggyback as soon as we launch this thing, boom. Make these other ones, and those ones will be way simpler.

Rob:

Do you build this to solve your own problems, or do you build this to get acquired from Apple and to fund films?

Drew:

I’m building this for fun. This, for me, is for fun. I don’t think this is ever going to be a VC scale company. I don’t think any of these Apple device brands really are, but they could be big companies that give you a good salary and this is not going to be helping me fund The Legend of Zelda, the trilogy, but it will be certainly fantastic to do. My gosh, dude, like the website with all the renders and all that, because it’s just going to be so good, I can’t wait.

Rob:

Okay, Drew, there’s so much to wrap about. I mean, I haven’t even talked about the pictures icons. Let’s keep it short and sweet. So you’re a prolific maker with many wins, often resulting from organically scratching your own edge, Okay. You’ve also grown a thick skin, building, failing, raising, exiting, starting again and again. To the listeners out there terrified of the upcoming AI landscape, what advice do you have for them? Should they stay calm? Should they get curious? Should they start poking around? What should other designers and makers be doing at this time?

Drew:

A good question. I think if you’re a designer or a maker, like, the number one thing that you should be doing right now is trying to understand what is going to be coming out of this AI revolution. You should understand what’s coming and not avoid it. I’ve seen a lot of tweets from other makers who are like, you know, what’s cooler than AI? Building it yourself and just kind of, like, dogging on it. I mean, come on, they’re big fans of the Internet, that was the new thing that everyone was afraid of. Why are they acting like that? I have no idea. Don’t be afraid of it. Look at it, see what it’s about, approach it with curiosity. And you don’t have to immediately think of how can I make money off of this thing? But maybe think of what are some of the implications of AI in this particular thing that I’m interested in and interested in building or that I’m currently working, what will come out of there? And I think it’s folks like us, the makers and builders of today, that are really going to play a huge role in shaping how AI interacts with the world of the future. And so I think there’s a ton of opportunity for all of us to be on the front lines building that future, but that’s never going to happen if you avoid it or if you don’t look into it. So I would suggest looking into it, whether or not you’re scared of it or you’re welcoming the new AI overlords, I think that’s beside the point of you should understand what is coming and how that will affect you and then let that marinate, let it sit for a while, and then maybe you’ll come on something that, hey, maybe I could build in this space or maybe this company that I’m working at is going to be obsolete in the year because the leadership thinks AI is a toy. Maybe I should go somewhere else, right? So, yeah, I would say first step, just get to understand what this is, how it works, and I think you’ll see pretty quickly where things are going to go.

Rob:

Brilliant. Drew, thanks for chatting with us, man. Where can people follow your journey online?

Drew:

Dude, it has been super fun talking with you. They could follow me on Twitter @drewwilson – If you look at my website, I don’t think I’ve updated for over a decade or something.

Rob:

Okay, rad rad. We’re ending this episode off with regular foot first by the 16 wheelers little surf tongue pop tune to get you in a good mood for the week. Go well. Drew.

Drew:

Thanks, man.