More Ideas Than Time: An Interview with Greg Pierce


Greg Pierce is the guy behind Agile Tortoise, the development studio behind one of my favorite iOS apps, Drafts, along with a number of other awesome things like x-callback-url. We chatted about the origin story behind Agile Tortoise and the reasons why Greg decided to make the leap into an independent software development career.

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Tell me a little about yourself. Who are you, where are you from, and what would you say you are most known for?

Well, I answer to the name Greg Pierce. I grew up in Maryland, in the DC suburbs, spent some time in New York (at NYU) and ended up in Texas, where I've lived in the greater Dallas-Fort Worth area for close to 20 years.

In real life, I'm the happily married proud father of three boys (11, 11 & 6). During the day I run Agile Tortoise, an indie software development company I founded in 2006. I'm probably best known for my iOS apps, particularly Drafts, and for spearheading the x-callback-url iOS inter-application communication spec.

I also play guitar. :-)

Dallas, huh? Well I hope Matt Alexander's not getting you involved with his madness or anything. So, how exactly did you get started with software development? What initially sparked that interest?

That's difficult to say. I've said it was accidental in the past, but I don't think that's accurate. Perhaps "unintentional" describes it better.

“I don't really self-identify as a "software developer" — I just like to solve problems and build things. Software is how I do that.”

I grew up with computers. My dad is an IBM mainframe programmer, so I had exposure early on with an Apple II, then the first PCs, etc., and I enjoyed fiddling with them and experimenting with programming. I never pursued that interest, however. My bachelor's degree was in music and I was actively pursuing a career in music and arts. My graduate degree is in Ethnomusicology and Folk studies.

All that time, however, I liked to make things. I co-founded a music- and arts-focused magazine in the early 90s (UNo MAS Magazine), and taught myself desktop publishing to support that project. Then I taught myself HTML to bring it to the web. Then I taught myself web development to automate the growing requirements.

After I finished school and entered the workforce, I ended up at a company that was struggling to enter the computer age (this was in 1995), and they gave me free reign to help — so I started building tools for them to manage their business and taught myself database/business programming along the way…so it all just sort of snowballed from there.

I don't really self-identify as a "software developer" — I just like to solve problems and build things. Software is how I do that.

That's pretty interesting, especially given how well-known you've become in the iOS app development world. What about the music thing, then? Do you consider yourself just as much a musician as you do a developer, or is that more of a side hobby?

Music is definitely a hobby at this point. I love music, and the consensus among those who have heard me play seems to be that I am a reasonably good guitar player, but I was more interested in working around music than being a professional performer. One of those things where the pressure of making it work would take too much of the fun out of it.

While my degree is in music, I was actually in a unique Music Business program at NYU that was focused on working in the industry. I got a lot of cool opportunities through that program and got to spend time working at CBGBs, MTV, Rough Trade Records and some other cool places back in the day.

Okay, I've gotta ask: what'd you do at MTV?

Adam Curry's personal hairdresser.

Seriously, nothing glamorous. I worked a couple of days a week doing mostly clerical work in the programming department. It was fun though. I got to sit in programming meetings, and meet a lot of artists that came in to promote new releases. This was in 1988.

Probably the coolest responsibility I had was preparing the daily Dial MTV Top 10 on the days I was there. If you remember that show, it was a top 10 request show compiled from viewer votes (to a 900 number, of course). I'd get the top 50 most requested songs list from the company that ran the phone lines in the morning, run it through a series of rules to determine the top 10 then take care of typing up the list (on Wang word processors!) and getting it to production.

The mechanics of it all were pretty interesting. The "rules" were around keeping the list from getting dull – i.e. the same video could not hold the #1 spot more than 3 days in a row, video were retired from eligibility after a certain period of time and had to on the current MTV rotation list.

Man, for a second I really had my hopes up about the Adam Curry thing...

So, we've got the MTV job in 1988, and then the programming job in 1995. What happened in the intervening time between that time period and the founding of Agile Tortoise in 2006?

During the '88-'95 period I bounced around a number jobs, until I headed off to grad school in 1992 at the University of North Texas. I completed a Masters from UNT, and went to Western Kentucky University for a year to continue my studies.

Turns out I was far less interested in continuing my studies than I was in getting married to my girlfriend Katie, who I had met while at UNT. So I moved back to Texas and we got married in October of '95.

“Having the kids was one of the main driving forces behind me going independent.”

Right around that time was when I started the job I mentioned early where I really taught myself programming. I was with that company for 10 years as IT manager. I also did consulting and side projects along the way. I put out a Mac shareware game in the late 90s (Turtle Dice), and did a lot of development and consulting in Userland Frontier — Dave Winer's scripting platform.

Most of my focus in the 2000s was on family though. We had twin boys in 2001, and another in 2007. Having the kids was one of the main driving forces behind me going independent. Some struggle with the discipline to work at home with kids, but I love being around.

It seems like going independent is becoming more and more common these days, which I think is awesome. I'm hoping I can somehow cobble together an independent career myself someday, and I love hearing the stories about how others have done it.

What was it like, starting your own business and leaving the corporate world behind? Did it terrify you?

I was lucky enough to able to ease my way into it over several years, but there were times when it was scary. As the primary breadwinner for a growing family, I couldn't afford too many lean times along the way.

When I first started a Agile Tortoise, I was doing client consulting and my previous employer was my anchor client. I went to them and explained that I would love to keep doing development work for them, but that I was not interested in continuing the IT administration end of my position. They had grown enough for it to make sense for them to hire a full time system admin. I helped them find a new person, and they outsourced the development to me on a consulting basis.

The development work I was doing at the time was mostly in Microsoft Dynamics AX and .NET. There was a lot of demand for that skill set, so even if being independent didn't work out I felt confident I'd be able to fall into something else. Luckily it did work out.

As it turns out, I still have one big anchor client. I spend about half my time building STEMscopes – a very cool K-12 education site – and about half on my own apps.

So, long story short, I never put myself in a place where I had zero income — and in the modern job market I would find it much more terrifying to be in a place were all my income relied on a single employer.

How long after Agile Tortoise was founded did you begin working on Drafts? What prompted you to develop the app in the first place?

Drafts shipped in April, 2012. I had probably been working on the app for about 4-6 weeks prior to shipping. Mind you the original 1.0 version was much simpler than the 3.0+ version currently in the App Store.

Drafts actually has a pretty clear-cut origin story. I was tapping away at a short email to my wife one day and realized I should text her the message because I needed a quick response. Sounds straightforward enough, but actually making that context switch on the iPhone was pretty painful. Select the text, copy, quit mail, open messages, address the message, paste. A first-world problem for sure, but still a pain.

I thought about it and realized how many other similar moments I had on my iPhone where I wanted to type something and I wasn't sure where it should go yet...maybe to Twitter, or Facebook, or both. Maybe to email or messages. Maybe it would become a calendar event, or maybe it would be better as a todo.

Drafts' primary goal was to remove those barriers by letting you just open it and type. The natural growth path for the app was just to give you more and better ways to act on that text once you typed it, so that's what I've tried to do as the app has grown.

I would say that that's my primary use for Drafts: a quick scratchpad for all those little ideas I think could turn into something cool later. But in the last year or so, Drafts has definitely evolved into something much more than a simple scratchpad.

Back in January, Federico Viticci wrote an article detailing the ways in which Drafts had suddenly become a sort of 'workflow automation hub' for anything text-related (mainly due to the x-callback-url specification you also developed). What inspired you to take Drafts to the next level like that?

It just seemed like the logical evolution of the app. I had already been working on app integration – x-callback-url was developed working on integration between my dictionary app, Terminology, and Instapaper in early 2011 – so it was already an area I was very much excited about.

I had done the work to integrate with a lot of different services, so why not unlock that and make it something you could utilize easily from other apps?

That's a good point. Are there any major plans beyond the upcoming iOS 7 updates for your apps that you've got in the works? Any particular industries you're thinking about getting into?

It's hard to be specific about the future. I have more ideas than time, and I while I love to discuss those ideas, I've learned it's best not to put too much out there since those ideas often get misinterpreted as promises — sometimes they don't pan out quite the way you hoped, and you disappoint people.

So I guess I'm more prone to keep quiet until I've got something close to ready-to-ship before I say too much.

“I have more ideas than time.”

Short-term though, I've been re-writing Terminology. It's been a popular dictionary-thesaurus app but was getting long in the tooth, and iOS 7 provided a good opportunity to refresh that app and add to it some of the things I've learned working on Drafts.

That's understandable, sometimes it's nice not to know exactly what the future holds. Let's switch gears for a second and talk about your setup and workflow. Where do you do most of your work, and what tools do you use to get it done?

I work at home in a bedroom that we use as an office. My setup is pretty austere. A slightly modified Office Depot desk and an exercise ball chair for furniture. I have a retina MacBook Pro hooked up to a Thunderbolt Display – and a great set of studio monitor speakers. I've tried a few other input devices, but keep coming back to the standard Apple Wireless Keyboard and Magic Mouse.

There are dozens and dozens of apps I rely on for things big and small. I was sitting at my kids’ iMac the other day and was faced with the reality of just how many apps I rely on so deeply on the Mac that I take them for granted. Some of them I’ve used for more than a decade.

I start to think of Launchbar, Default Folder, TextExpander, 1Password and the like as features of the OS sometimes. They are so ingrained in my daily flow that I hit hot keys for them on a Mac that doesn’t have them installed and I think the keyboard is broken for a split second when nothing happens.

More recently, I’m finding Napkin to be a great tool to help with app support and documentation, and I’ve pretty much moved all my vector graphics work to Sketch.

iOS is less stable for me. I have some core apps that stick, but as that is my development platform I’m always looking at new things.

What does a typical day look like for you?

My days start early. I’m the morning person, so I get the kids up, get them fed and off to school most days. I’m generally back home around 8:30 and get straight to work.

I try to divide my days up by projects to some extent, though it doesn’t always work out that way. I will typically spend 30-35 minutes on communication first thing. This includes getting caught up on support email, and getting aware of any critical issues I might need to move up on the priority list.

Then I will spend the rest of the morning on one thing. That might be one of my apps, or a client project.

“It’s a nice perk of working at home to have these mini-dates.”

Most days I eat lunch with my wife. We often eat out. It’s a nice perk of working at home to have these mini-dates.

I often shift gears to a different project in the afternoon, and depending on current priorities try to give myself at least one afternoon a week where I work on experimental projects. This might mean exploring a new technology, testing out some new UI ideas, etc., that may or may not eventually make it into a project.

I will sometimes keep up with support issues and such off hours, but I’m mostly a 9-5 type and don’t work in the evenings or on the weekend.

One final question, and I'll make it a fun one: do you currently have any favorite books/podcasts/albums/whatever that you think others should check out?

That’s a tough one. My music tastes are all over the map. Been digging into John Hartford’s catalog on Rdio lately – probably too superficially bluegrass-y for many, but he’s a really great songwriter with a unique blend of optimism and keen observation of people. Closer in spirit to Randy Newman or John Prine than first listen reveals.

NPR’s Planet Money is currently my favorite podcast, both for its interesting take on every day economics topics and for its shorter format, which fits well with my typical listening opportunities.

Excellent! Thank you for stopping by to chat with me, Greg.

You can find Greg on Twitter at @agiletortoise and on ADN at the same handle.