Drew Wilson is one of the most prolific entrepreneurs building today. I was lucky enough to be able to sit down with him in beautiful Carlsbad, CA where he resides. We talked about his early days advertising in the yellow pages and what drives him to promote fellow entrepreneurs through his projects the Industry and ValioCon. We also discussed his process for building quick prototypes and managing a multitude of ongoing projects.
Tell me about how you got started.
I built my first site in 1996 when I was 13. Nobody I knew was in the industry whatsoever and my parents weren’t super tech savvy. My process was “hey I want to freelance, let me put my name in the Yellow Pages.” I went out and spent $2,000 on the biggest ad I could afford. It was a lot of money for me at the time. For the entire year I didn’t get a single call.
The sale guy calls a year later “hey, do you want to renew?” I’m like “actually I’m taking it out. I haven’t gotten a single call.” Then the most ridiculous thing ever happened. He comes to my house and he’s like, “What? You think you’re too good for the Yellow Pages?” I was like "no, but I haven't gotten a single lead!" and then he bitterly responded, "well maybe you're just not good enough for the Yellow Pages."
Are you familiar with the concept of small business referral networks? I tried that next. I was the secretary treasurer. Everybody there was a small business advisor who completely didn’t get the web. They were like “oh my god, $1,000 for a website! You’re crazy Drew.”
So I said “let’s make a website for this chapter. I’ll try to get us on Google and get some search results going. I’ll do it for free, If you want to be listed just give me 50 bucks.” One of the guys wrote the chapter president the next day, “Drew Wilson is a crook. I can’t believe he’s trying to take $50 from each person. There’s no way this would cost that much. I think he should resign.”
When did you start building an audience around your work?
It was a little bit before Pictos came out, in the early days of Twitter.
Tell me about your motivation behind the Industry.
When I had an opportunity to showcase people, I wanted to do that because I know how it is, struggling to get noticed. That was the whole drive behind the Industry. I’m so sick of people just following the money. What about the dudes who are doing stuff that’s good but just don’t want to give up all their company or don’t want to play the game? That’s why I made the Industry.
I don’t write and I don’t want to. I didn’t want to maintain Industry from the get go. I built up a team. I was like “Okay guys, I’m stepping back now, run with it.” It stagnated for a little while, but now with the new design and focus from the team, it’s back up.
Are you still behind the new re-launch?
I resigned everything because we were going to ramp stuff up significantly, but once I pulled back nothing got ramped up. That design didn’t really work with how they were going to go forward anymore. Now they’re just doing I think two or maybe three posts a day to keep it small and grow. The new design that I had done was for way more content and we were going to network with other blogs and all this other jazz.
Let’s talk a bit about the new ValioCon site, it got an amazing reaction from the community.
It’s super encouraging, I didn’t realize that people would like it so much. One of the things I was going to blog about was the images. People are like “oh, the images look so good.” I’m like “well, if you would have seen them beforehand.” Every photo on the site was colored including the speakers heads. I hadn’t done that with the last two. I was like “this needs to fit better with the design.”
Since it’s a design conference I wanted to be up with what’s going on in the design world and how to look current. My motivation behind it was to make a super killer site that will look really good and then try to get a cool crowd together for the event.
Are you in Photoshop laying out everything, or are you designing in the browser?
Yeah. Typically everything I do is in Photoshop, at least for the initial cut. If it’s a homepage, the homepage is in Photoshop. If it’s an app, I’ll do the internal screen the main dashboard or something and the homepage. Then usually I’ll do the rest in code these days. It just depends on the project. If it’s going to be something really design heavy I’ll do it all in Photoshop. Every single one of my projects except Namebox started in Photoshop.
One of the things you’re known for is just the volume of products that you’re putting out. Do you have a base framework that you start from?
Nice. You’re collaborating with a lot of people which is giving you a unique network of individuals who are also building. Take me through how a project like Roon comes together.
With Roon I wanted to have a blog. I was like if I’m going to build a blog for myself I might as well build it for everybody else too. My goal was to write natively. I don’t want to write on the web, I hate writing on the web. Soffes had tweeted something like “hey, check out this text editor I’m going to start building.” I DMed him “Hey, let’s combine your mac app with my blogging idea and make something rad.”
So we started building what became Roon. The whole idea was to make the Mac app, it’s one of the first things but it still hasn’t been done. It’s partially done, so it won’t be too much longer. Hopefully we’ll have time in the next couple weeks to sit down and do it in two days or something and pump it out. It has an iOS app, so iPad and iPhone and then it’s got the web app version. A super cool frontend and it’s great. People took to it, tons of people use it.
I’d like to hear about your ideas behind LUMO
Instagram is great, I have nothing against that. I’ve just never downloaded and used it because of the fact that I don’t want to be limited by the square format. I understand that’s the whole purpose behind it.
I just wanted something where I could create more of a website for my photos. LUMO has taken a while to do everything just because it’s always been more “when I get time for it.”
With LUMO you just take a photo, you add a filter and upload it through LUMO and then it’s on your site. That’s something I wanted. I just wanted to be able to take some cool photos of my kids or if it’s something I’ve seen, post it up on a site.
How are you prioritizing all of your projects?
Just what I’m inspired to do mostly. I’ll get super bored in one thing and like “I want to do this other thing again” so I’ll do that. That is the main factor and the other factor is necessity. If something is broken somewhere then obviously it takes my priority or a ton of people requesting some feature, I’ll get on that. If it needs to be updated, if there’s anything updated for a long time I’ll get on that. People say “why don’t you just focus on one? You’d be so much better if you focus on one.” Which I totally disagree with because maybe that product could be better based on your current skill set. That doesn’t mean the product could be ultimate.
In order for the product to be ultimate you would have to be ultimate. It can only be as good as you are and if you’re not very good it can’t get very good. I look at it like that. If I can do a bunch of different things, get a bunch of experience doing other things, pushing myself on how something should be designed because it’s for this demographic or that demographic and pushing myself on development, I can get good quickly. I feel I’m now at a point where I do want to concentrate on one thing, because I feel I’ve now got enough experience to make one thing really great.
You can focus on one thing right out of the gate if you want, or you can try a bunch of stuff and then focus on one thing.
What’s been your biggest surprise in terms of a product taking off?
The Pictos site. I had no idea it would do anything like that. The best icons in time were Helveticons which were $249 for 210 icons or something like that. There was nothing else. There was glyphish icons which were free. There wasn’t really any other ones for sale and so I didn’t know how to price that. I’m like “I’m just going to go way low.” I set them at 29 bucks and then it just took off and that’s what’s funded me up until recently, now nobody buys anymore because they’re so old. I don’t really want to make icons.
Are you Spotify or Rdio?
Rdio; I was on Spotify for a while but just because Rdio is a design focused company I just wanted to give them my money. I really don’t think they’re doing a very good job; (laughs) in my personal view.
What do you want your legacy to be?
I don’t know, I’m too young. I do piddly stuff right now and I’m hoping that this piddly stuff will make me a good amount of money so I could do bigger dream stuff. I would like my legacy to be one of those things that I do in the future.
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