Making Vesper, NetNewsWire & OmniOutliner: A Top Dev Interview With Brent Simmons

Welcome to another installment of our Top App Dev Interview series. Each interview in this series focuses on a successful mobile app or developer and the path they took to get where they are today. Today’s special guest is Brent Simmons.

Brent is a prolific technologist, technology writer and speaker. He is best known for being a developer at The Omni Group, the developer of Vesper and creator of NetNewsWire.

When he’s not busy programming, Brent is either writing on his blog or speaking at various conferences around the world, including AltConf & CocoaConf.

Focus

Brent, you’ve worked on a number of popular apps such as NetNewsWire, MarsEdit, Glassboard, Vesper, OmniFocus, and more. Out of all of these apps you’ve worked on, what is the one you are most proud of, and why?

The answer probably depends on my mood — I’d give a different answer every time you ask!

But today — maybe because my old boss and friend Dave Winer recently visited — I’d say Manila. Manila was a very early blogging system that shipped in 1999, when I was working at UserLand Software. After Dave had the idea and did the foundation and design, I took over as lead developer and shipped it.

And it was awesome. It had “Edit this Page“ buttons so that if you were looking at something on your blog, you could edit it. This was new at the time. We had hundreds of thousands of users on our free service — some well-known blogs such as Daily Kos and Robert Scoble got started on Manila.

This was the first big project I ever did and, even though it’s not still around, it did help start the blogging revolution, which was a big part of the open web, which is one of my passions.

You’ll note that almost everything I’ve done — certainly the best things — have to do with reading and writing on the web. That’s been the theme of my career.

That’s a great point. In addition to being well known for development, you also are a prolific blogger, podcaster, and conference speaker. These kinds of things obviously take a lot of time and energy – why do you do it and what benefits have you seen in your life from these pursuits?

Although Manila is the product I’m most proud of, if we expanded this to ask what *thing* I’m most proud of, the answer would be obvious: my blog. I’ve been writing it for 17 years. When I was a kid I wanted to grow up to be a writer, and I *am* a writer. My blog isn’t a side thing: it’s the main achievement of my career.

I wasn’t sure that I’d like speaking at conferences. I’m extremely introverted. I like reading and writing, which are things I can do alone in a room. But, to my surprise, I found there’s a part of me that’s a little bit of a ham. I like performing for a crowd — and I definitely think of speaking as a type of performance. I even like playing music for people as a Conditional Breakpoint.

My uncle is an actor. I never understood the appeal of acting, and I figured he was from outer space — until, sometime in my 40s, I started to become comfortable on stage, and I started to understand and really enjoy the connection you can make with an audience. Now I get it, at least a little bit.

What I try to do when speaking is pretend it’s just you and me sitting in a bar. I shoot for relaxed and conversational and intimate and, hopefully, a little funny. I tell stories. I’m not afraid to be weird. I prepare a bunch (more as time goes by), but with the goal of making it seem like nothing, as if I just got up and started talking to you. (It should be no surprise that my approach to writing is similar.)

Let’s go back to apps. Some of your apps are now managed by other companies – for example, NetNewsWire is run by Black Pixel, and MarsEdit is now run by Red Sweater. Why did you decide to transition these to other companies rather than maintain the apps yourself, and how did you perform the transition in practice?

NetNewsWire by Brent Simmons

NetNewsWire by Brent Simmons

With MarsEdit, I had just started working at NewsGator. NewsGator’s initial focus as a company was RSS, and so NetNewsWire was the priority. I couldn’t do a good job with both NetNewsWire and MarsEdit, so rather than shut down MarsEdit, we found it a great home with Daniel Jalkut.

We sold NetNewsWire to Black Pixel many years later. I’d been working on NetNewsWire for nine years, and it was clear to me that to do syncing well and maintain iPhone, iPad, and Mac versions, it needed a bigger team. At the same time I had an opportunity to start a new company (Sepia Labs) and create a new group messaging app: Glassboard. There was no way I could work on NetNewsWire part time, when what it needed was more people, not half of me. So we looked for a good home.

Part of the transition is coming up with a deal that both sides like. These tend to involve some cash, some revenue-sharing for a period of time, and some incentives for the purchasing company to put resources into the app.

The second part is turning over the code and related resources. I’ve always made myself available for technical assistance after the sale, but there’s been very little of that needed.

Given your success and senior status, you must have a large number of ideas for new apps to work on, or opportunities to collaborate with other people on new projects. How do you decide which opportunities to pursue?

This part has actually gotten easier. I’m 48 years old right now, and I have a day job. This means I can do one or two more serious apps, and that’s it. Probably just one.

It happens that there are just two app ideas I’ve been obsessed with for a couple decades. I picked the one of the two I’m most passionate about, and I’m working on that.

There are other ideas and opportunities that come up that sound really, really fun. But then I remember that time is limited, and there’s this thing I want to make and maintain for the rest of my career, and that’s that. So I stick with that one thing.