Problem solving with Ben Sinclair

Ben Sinclair is passionate about software. Whether it’s monetizing one of his many web properties or designing the technology behind his current endeavor FliteBrite, Sinclair loves bringing a project to life. And he’s got a lot of them.

No matter the technical challenges, Sinclair relishes working through a good problem. Recently he shared a bit about the many things he’s building, how he works through technical challenges and where he finds inspiration.

This interview has been edited for conciseness.

Clay & Milk: What are you working on right now?

Ben Sinclair: I’ve been working with a friend of mine for years and years now, building crazy websites and monetizing them through advertising. I’m currently working on one related to history. It’s the remains of a larger set of sites we had on weird topics like cats and quilting and dogs and stuff, which we sold most of a few years ago. We had a cat Facebook page with more than three million likes, and when you do that, you can drive traffic pretty much anywhere you want to things you’re monetizing through advertising. 

Aside from that, I do a little bit of consulting here and there. I help build prototype hardware and software projects. I actually can’t even say which kind of hardware projects I’ve been working on recently because I think there are [non-disclosure agreements] involved.

I’m also working on FliteBrite, which is really exciting right now. We’re just delivering our first products.

My family has also been in the automotive parts business for a long long time. We got rid of all that in the ‘90s but we have one store left that we purchased back. It doesn’t require much time from me or anybody else involved, but it’s there. Sometimes I lead with that if I don’t want to explain all the technical web stuff that I do. I just say “Oh, I sell auto parts” and then you can continue the conversation.

C&M: How did you get involved with this?

BS: I need to ask my friend I work with how we got together working on the web property stuff because I honestly don’t remember. We worked on a startup a while back called It was a weird online resume builder that we ended up selling to a company called, which does online reputation management. When we first started working together, we actually had never met. I didn’t actually meet him [in person] until we went to California to their office and handed it off to them. Since then, he and I have worked on a lot of different projects together over the years, just continuously building whatever we feel like.

FliteBrite came about just because Ben [McDougal] and Ethan [Davidson] started thinking about it. They needed someone on the team with the technical expertise to actually build the product. We started talking one day at 1 Million Cups and got together after that. It’s been about three years now.

C&M: What keeps you motivated to pursue this type of work?

BS: At the core, I’m just interested in building stuff. I’m certainly more on the technical side of any of the businesses I’m involved in. I just like the technology. I like taking random, crazy ideas we have, like FliteBrite, and actually building the physical thing. That’s actually one of the great things about FliteBrite. I’ve been doing software stuff for so long, but you can’t pick up software and hold it. It’s really cool to have a physical product in front of me. I just get a kick out of bringing stuff to life.

C&M: What was an unexpected challenge you faced building FliteBrite?

BS: The challenges in all the other things are kind of the same challenges anybody faces. When you get into FliteBrite, you get into the hardware challenges. I’ve dabbled in hardware from a hobby standpoint for a long time, but this is the first commercial thing I’ve helped build. There’s a different way of thinking about it.

We ran into problems with simple things like availability of components. We went down a long path of using a certain kind of screen, and when we went to price out 1,000 of them—which you should do first, by the way—they told us they couldn’t get us 1,000 of them because they’re also highly in demand for smartwatches. We were at the bottom of the list after Samsung. We’d designed this whole product around this specific screen and then we couldn’t get them. It’s that which caused us to go in the direction of the bigger touchscreen we’re using now.

We’ve also had some manufacturing issues. You get all these 3D prints, and sometimes they work and sometimes they don’t. The first run [of FliteBrite paddles] wasn’t quite right because apparently the choice of plastic makes a big difference in how they come out. We just ran a second set this week with new plastic and they came out beautifully.

C&M: How did your previous experience help you with what you’re building at FliteBrite?

BS: All the software stuff is just a building on experience, but when it specifically came to FliteBrite, I think one of the biggest things is the team we have. We’re all really good at certain aspects of what we do. I don’t think another team that had this idea but didn’t have the in-house expertise could have gotten to where we’re at with it in the amount of time and money we’re into it. It’s been a great way to combine all the different areas of expertise I have.


C&M: How do you get new ideas or fill your non-work well?

BS: I do a lot of projects for myself just solving problems I have. Some of them are related to the workflow I have during the day so I’ll write stuff to improve that. I’ve got a lot of hobbies too so I’m always writing things to help me with those.

If I’m stuck on a technical problem, I usually just take a break. Sleeping on something makes a huge difference because you stop thinking about it and suddenly the solution pops into your head. That usually happens right when you’re about to go to sleep so you have to get up and find a piece of paper. Otherwise, I have lots of friends I bounce ideas off of. The community here is pretty great. You can go down to Gravitate and talk to lots of people about ideas. I talk with Cameron Webb about technical problems I have a lot of the time.

C&M: What did you think you would be when you grew up?

BS: When I was a little little kid I wanted to be a farmer because we lived out in the country and that’s what I saw. Also, tractors are cool. I still maybe would be a farmer, especially now that it’s all high tech. But once my mom brought home an Apple II, that just blew my mind. It was a Christmas present for the family one year, probably ’84 or ’85, and that changed everything. At that point, I immediately knew that’s what I wanted to work with.

About Ben Sinclair
Age: 38
Location: Waukee, Iowa
Twitter handle: @realbensinc

Megan Bannister is a freelance writer based in Des Moines and a regular contributor to Clay & Milk.