Build for Yourself: A Top App Dev Interview with Drew Wilson

Check out our interview with Drew Wilson, prolific indie software developer. Learn how he works, how he got started, and his best piece of advice! By Cesare Rocchi.

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Welcome to another article of the Top App Dev Interview series, where we interview developers and designers who are running successful software businesses.

Building a successful business isn’t easy, and it doesn’t happen overnight–it takes passion, hard work and a few million cups of coffee :]

For this interview, we have none other than Drew Wilson, the impressively prolific author of many web, iOS and Mac apps. He started building software almost twenty years ago, and apparently nobody can stop him (not that we’d want to).

Read on to discover how Drew works, how he got started, and his best piece of advice.

Meet Drew

The Plasso Market

For sure. I’m Drew Wilson and I make software.

I got started early on, and made my first website in 1996. These days I focus on designing and developing my own software. Mostly web software, but I also have built a number of iOS apps and a couple Mac apps.

Currently I’m working on my payments platform Plasso and I am about to launch a new photo editing platform for Mac and iOS called Filtron.

Hi Drew, and welcome! For our readers who don’t know you yet, can you give us an overview of who you are and what you do?

Awesome, it sounds like you have a lot going on. How did you get started as an indie software developer?

I started doing traditional art as a kid. I was lucky enough to have access to Photoshop when it was at version 2!

A few years later, I started experimenting with designing websites. I had seen way back in ’95 or ’96 and was blown away at how they had a sidebar and header that came together with a curved line. I was so curious as to how they made a curved line and a website that felt cohesive, rather than just a bunch of text/images on a page.

That curiosity led me to learn HTML/CSS. But I never wanted to code, which seemed so boring to me at the time. It wasn’t until 2002 that I finally decided to learn a server side language (PHP).

Learning to code totally changed my life; being able to fully realize my designs all by myself was amazing. I immediately started building my own ideas. It wasn’t until 2008 that I released my first piece of paid software.

Build And Build And Build

What’s your process for building a product? Do you start by scratching an itch, or do you conduct market research?

I build what I want. So if I wish there was a tool to do X or to do X better, I’ll build it.

It’s great because even if the tool doesn’t do well commercially, I still benefit because now I have a tool that works the way I want it to. I never need to do market research because I like to build things where I am the target market.

You work mostly solo, but when you team up with other developers or designers, where do you find people to work with, and how do you handle payments or royalties?

I reach out to people I like and know are smart. I like to build for fun, so I mostly partner up with people I can have fun building with. Typically these are people I’ve met before through some event or just from twitter convos.

Long ago I built a website to connect designers and developers called (which is about to re-launch with new owners). I once used that to find a developer and he ended up being a good friend–we still make stuff together all these years later!

When it comes to split, it’s always even. If there are two of us, then it’s 50/50. The only time that has changed is if I already have an existing product with traction and/or revenue. If that’s the case then the split is not 50/50, but something fair for sure.

Good dev puppies split profits equitably!

Dev puppies

You develop Mac apps, iOS apps and web products. Which of these have you found to be the most lucrative?

Web. The most profitable thing I’ve built to date is my payments platform Plasso.

Second most profitable would be my icons, Pictos.

I also built and launched a screen-capturing app for Mac years ago called Screeny and it did really well; it was the tenth top paid app in the Mac App Store. At its best, it made around $3-4k one month. But significant sales didn’t last more than a few months.

My most downloaded and used iOS app is one I built in 24 hours – LOL! It’s a free app called OffOf and it has a 5 star rating!

A screenshot of OffOf

A screenshot of OffOf

I’m hoping to change all that and finally be featured by Apple (hopefully) with Filtron. I’m releasing a Mac and iOS app at the same time, as well as a web component. Hoping people love it as much as I do. I’ve been working on it for two years. Yes, two years.

Mac development is hard (especially since this is really my first Mac app where I’m doing more than just UI development). It’s been a very painful road and I’m super excited to get it out.

Blood, Sweat and Tears

What’s the product that required the biggest effort? How long did it take to build?

Up until Filtron, it was my first piece of software, Firelift, which took two years to make and involved multiple all-nighters per week.

I’m not doing all-nighters with Filtron, but it’s the largest task I’ve undertaken to date. It started out as a different app altogether, and evolved into what I’m building now. Counting the time I spent building what Filtron used to be, I’ve been working on it since 2012. Insane, I know.


What challenges did you stumble upon during its development?

The biggest challenge was finding people to work on Filtron. UI development is one thing, but Filtron has its own filtering engine based on GPUImage. Not many people know how or want to work on something that complex. Finding people to work on Filtron with me has literally been the single hardest thing I have ever done. Literally.

I eventually realized I needed to get good at Mac and iOS development very quickly. In that regard, it has been great. I’m super confident these days in my ability to make Mac and iOS apps. Literally one year ago I hardly knew anything about Mac and iOS beyond UI development.

Let’s talk about Swift. Have you used it? What was your experience?

I use Swift in the Filtron Mac app. The iOS app was built before Swift came out, so rather than spend any time converting it, I’m finishing the Mac app.

Swift is great, but the bummer with someone learning it this early, for a pretty complex app, is lack of documentation. I always tell my wife, “If Filtron were a web app, I literally would have built it in a month”. It’s very true. Many web developers don’t have a clue how good they have it!

UIKit and iOS is pretty close to the web, with tons of resources, documentation, OSS, etc. But it’s a completely different universe when you go to the Mac.

I often feel like I’m the only human building Mac apps. Most articles written about Mac dev or code samples on the web are years old. It’s terrible. Unless you are building a super simple app, you have to figure most everything out yourself. Which is great, but ultra time consuming.