Interview: Dave Caolo, Blogger at TUAW & 52 Tiger

Website: http://52tiger.net
Twitter: @panache
Bio: Dave’s been blogging for many years. Originally from Scranton, Pennsylvania, Dave graduated from Marywood University in 1994 with a BS in Psychology. He’s been a New Englander — and a Red Sox fan — ever since. When not writing, Dave can be found kayaking, cheering at Pop Warner football games or playing with his kids, Grace and William.

Tell us a bit about yourself. We know you love writing, Apple, and the Boston Red Sox. Care to share a bit more about your personal side?

Sure. I was raised in Scranton, PA, where fun goes to die. I think that’s the official slogan of the Chamber of Commerce. Seriously, Scranton is home to honest, hard-working, blue color people whom I miss every day.

What was your first job?

At 12 I became a paper boy. Every day around 3:30 I stood on the corner of Dartmouth St. and Main in West Scranton and waited for my “bundles” to arrive. My job was to put them into a bag and deliver them to 4 blocks worth of customers.

The Wednesday editions were always too heavy to fold, and bound with a heavy strap of plastic and shrink wrap, which had to be cut off. I usually carried a Swiss Army Knife for the job. On the days I left it at home, I’d search for a sharp rock (a lot of fun in the snow) or gnaw like a badger until I had broken through.

The job featured everything you’d expect from an urban paper route: a demonic dog with a taste for newsprint (specifically, a basset hound named Daisy who, despite the stubby legs, could move like a gazelle); the weird guy who never spoke or shaved; the kind old woman who offered me popsicles on hot days and a third-story walk up with an open back porch. That stop begged me to hurl the wrapped paper has hard as I could into the air, over the railing and onto the porch. I often made it on the 4th or 5th try.

How long have you been writing?

I started as a college student by submitting bits of prose to my student magazine. It was the kind of forgettable dribble that college freshmen were so fond of, when taking oneself too seriously is elevated to an art. Fortunately, I had a demanding psychology professor called Sr. Gail Cabral. She wasn’t a member of the English Department, but she required flawless writing. Today I credit her with starting me on the path of professional writing.

Were you always writing about Apple, or did you begin with a different niche?

My first paid writing gig was for The Parenting Post, the official blog of Parenting Magazine. That started in 2003. I spent two years writing weekly posts about my experiences as a new father that will one day humiliate my children.

How long have you been a Mac user, and at what point did you decide to switch from using Windows (if you previously were)?

I’ve always used Macs. My high school didn’t have a computer lab, and it wasn’t until I got to Berklee College of Music in Boston that I got my hands on one. Of course, all of the studios and labs were full of Macs. After two years at Berklee, I transfered to Marywood which was another Mac-friendly school. Finally, my first job out of college was teaching at a residential school that used Macs exclusively (SE/30′s). The first computer I ever bought was a 333MHz G3 iMac, which I still have.

How’d you land the gig at TUAW?

Years ago I started reading TUAW. Eventually they put out a call for writers. I applied and was hired a couple of weeks later. This was back when TUAW was still a part of Weblogs, Inc. and under Jason Calacanis’s direction. It was fun to have been a part of TUAW and Weblogs back then, and I still keep in touch with my former co-workers from back in the day.

How has your writing changed in direction alongside Apple’s seemingly-never-ending product evolvement?

My writing has changed immensely since my days with The Parenting Post. When I read some of my old posts, I shudder at how wordy they were. Some of the stories that I was proud of desperately need the Red Pen.

As for writing about Apple, a few things stand out. As you mentioned, their product line is changing all the time. When I started, the iPhone, iPad and iPods didn’t exist. I can remember watching Steve Jobs introduce the iPod and thinking, “An Mp3 player? All of that hubbub for an Mp3 player?” That shows you what I knew.

As Apple’s product line changes, I’ve got to remember that its customers, and my readers, have varying interests. Some aren’t the least bit interested in the iPhone, iPods or iPads, while some are only interested in those things. Some enjoy keeping vintage machines alive and still others are heavily invested in pro aps like Final Cut. When writing, I have to consider what my audience wants to read about, and that doesn’t always line up with my personal interests. At TUAW, my responsibility is to that wide audience, and the whole team of TUAW writers strives to publish something for everyone daily.

What’s the hardest part about being a freelance writer?

Time allocation, hands down. In the space of 24 hours, I must be a father, a husband, a writer, a member of a community and a neighbor who gets dressed and takes a shower. It’s a luxury to work from home but it’s not easy. The one piece of advice I offer is this: create a daily schedule and be prepared to abandon it at a moment’s notice. A sick child, a malfunctioning cable modem, a power outage or any of a million other things can foul up a work day. When that happens, you must be able to respond with a calm mind and rational thought. No, I can’t work today. No, it’s not the end of the world. Tomorrow I can have at it again.

Are there any parts of your job that you find tedious and boring?

The daily RSS feed scavenger hunt gets tiresome. One of the first things I do in the morning is comb through all of my feeds for news and other tidbits that will be of interest to our readers. I shouldn’t complain, as there are significantly worse jobs in the world, but I’m not always enthused to begin.

How are things with 52 Tiger going so far?

Things have gone tremendously well. At the end of October, 52 Tiger will be four months old and it’s about to hit 2,000 subscribers. I’ve gotten links from the very people who inspire me, like John Gruber, Patrick Rhone and Shawn Blanc. Frankly, each one of those writers has set a standard that I strive for. I promised to bust my backside when it launched and I’ve kept that promise.

The idea is to create a place for people who like to sit in a quiet chair and read long-form articles about Apple and other nerdy things. Occasionally I’ll share a carefully curated link if it’s something I really enjoyed. I figure that the people who read 52 Tiger — my “ideal readers” — share my interests. Therefore, when I find something that blew me away with its functionality, purpose or design, I share it.

But the overall goal is to consistenlty write articles that are worthy of your time, attention and Instapaper queue. I won’t be the first to deliver breaking news, but the time and thought that go into my posts should make the wait worthwhile. I’ve gotten some flattering email from readers, which I appreciate.

Any other social media avenues you recommend besides Twitter for building web traffic?

Honestly, I only use Twitter and Facebook, and I don’t do any marketing with Facebook. Instead, I use it to communicate with friends from high school, college and my earlier adult life. Frankly, if I could get those people to email me consistently, I’d abandon Facebook entirely.

When you’re not writing, what are you reading?

Novels. I’ve been on a Haruki Murakami kick for the past year, and am making my way through his work. I’m several books in and am currently working on Sputnik Sweetheart. I’ve also got The City & The City by China Miéville on my nightstand, waiting for me to finish Sputnik. Call me old-fashioned, but I still like paper books that I can hold, bookmark and set on a shelf. The iPad, Kindle and Nook are all nice devices, but I prefer a physical library. This might become my “old man sticking point.”

Ever consider writing anything fictional?

I did for about as long as it took me to realize that I’ve got no business writing fiction. I’ll leave that to those who know what they’re doing.

What’s your hardware/software setup look like?

My rig was recently featured by Shawn Blanc. Basically, it consists of a beaten MacBook Pro (come to Macworld Expo next year and I’ll let you take a look), a 17″ Viewsonic display and an old Apple Extended Keyboard II which I connect to USB with a Griffin iMate. I also use an Apple Mighty Mouse.

When writing for TUAW, I type directly into our CMS. Articles that will appear on 52 Tiger begin as an outline in a paper notebook. I sketch out ideas and research notes in the notebook until I’ve got a good idea of where I’m going to go. Then I move it into Simplenote for fleshing out. It will sit there for a couple of days, depending on length and the amount of research/fiddling I’ve got to do.

When I’m feeling good about it, I’ll move it into WordPress. It usually sits overnight so I can give it a final once-over with fresh eyes before hitting the publish button. Unlike TUAW, I don’t have the luxury of an editor at 52 Tiger, and I’m quite good at making typos.

If Apple were to fall off the face of the Earth and you had to pick another tech. company to write about, which would it be?

Google. They’ve got so much going on, I don’t think I’d ever get bored.

And lastly, if you could ask Steve Jobs one question (in person), what would it be, and why?

Why “Apple?” In all the years that I’ve read Apple history and lore, I’ve never learned where the name came from. Wouldn’t it be fun to hear it from the horse’s mouth?