Here’s an interview we did with Tom O’Connell back in May of last year, re-posted here(!)

Tom O’Connell is a freelance writer extraordinaire currently residing in Albuquerque, NM.
His writing has been published in Details, The New York Press, Entertainment Weekly, GQ, Esquire, and Penthouse. We had a conversation about his writing, the politics & business behind getting yourself published, and the challenges facing freelance writers today. Here’s our conversation…

JNOW: Give us a little background on your early life in Indiana. Where did you get your start in freelance writing & journalism in general?

I grew up in Ft. Wayne. I moved to Manhattan in 1996 after graduating from Indiana University with a B.A. in Anthropology. I wrote fiction in college and wasn’t interested in journalism until I landed my first editorial job at New York Press, in 1998. I started there as a classified ad exec. One day I happened to be using a urinal next to Russ Smith, the publisher, and I pitched him an article about being attacked in a grocery store by the nephew of the Dalai Lama. He told me to write it, and that became my first published article. A few months later, after several more bylines, John Strausbaugh brought me over as an editorial assistant. It was a neat time of my life.

JNOW: As a writer, how do you feel about the rapid transition of print content moving online?

It’s unfortunate in a way. The romance of being a print reporter—at least what I’d gotten from movies and other accounts growing up—is all but dead. I came into publishing in 1997, fairly soon after the transition from hot-type to computers and around the beginning of digitization and the Internet, so I’ve no idea what it was like being a grizzled old hack in a smoky newsroom spending endless hours tracking down information that now takes half a minute to find, but I imagine some of the mystique was true. [At the same time] I can’t imagine having to fact-check a feature story without Nexis and Google. It’s cool that your work can appear and be accessed all over the world instantly. But it’s sad that the daily paper is quickly becoming a relic. It’s obvious that print magazines and papers won’t die out completely—nothing can replace the experience of reading the paper with your morning coffee—they’ll just become monopolized and homogenized as competition dies out. Imagine your only newspaper option being USA Today. Scary but possible.

JNOW: You recently covered real estate & business at the New Mexico Business Weekly. Did you face any challenges on this beat and if so, what were they?

Switching from a national to a local format was strange. The Biz Weekly hired me after I’d written a couple of profiles and features for them. A fellow ex-New Yorker, a PR guy, got me in the door there. It’s hard to make in-roads here if your people haven’t been here for at least a couple generations, so it was kind of amazing that I landed that job. I’d never written business articles before, but luckily real estate is the “sexiest” beat at a business pub, and I had fun going to events and interviewing millionaire real estate people and politicians and touring historic properties, like an old mental hospital on our main drag downtown that the new owner wants to turn into a boutique hotel. There are really talented businesspeople here with vision, and it was an honor to be able to pick their brains.

It was a high-pressure job because commercial real estate is the most visible and high-stakes business in any municipality, and every business leader, politician and real estate professional in the state was looking at my stories each week. I’d been used to writing mostly entertainment features and profiles for national magazines, and now I’m writing about square footage and creative financing and the art of the deal. I was a real estate agent in Manhattan for a year when I first moved there in 1996, but that was a long time ago. I had to learn a lot and hit the ground running. I loved to do continuing stories that were juicy and of more general interest, like the Scientologists’ purchase of a building downtown for their new church. That was interesting. I did a police ride-along for a series on the city’s crime-free housing initiatives.

JNOW: You’ve been published in the New York Press, Details, GQ, Esquire, and I recall a few years back you had a brief writing gig at Penthouse. Do you have any amusing stories from your time at Penthouse?

Penthouse was a blast. Sometimes I miss it. Sometimes I don’t include it on my resume, but I learned a lot about publishing during my time there. I also learned a lot about dysfunctional personalities. It was a dead-end job, but it came with a lot of colorful experiences, tons of freebies and invites to unusual parties and events. One of my favorite events was a press party for Sam Adams. I’m talking to Jim Koch about my home-brewing attempts using a kit called Mr. Beer. Funny. I had some great writing assignments. They sent me to L.A. to interview the cast and creators of Reno 911. And then there was the time I profiled high-rise window washers, and I put on the safety belt and went out onto the ledge of an old cast-iron building in SoHo to see what it was like. There’s a picture of me in the article hanging off the side of the building, holding a squeegee.

JNOW: You’ve covered Scientology protesters recently in Albuquerque, and in the past you’ve interviewed people like Evan Seinfeld (of Oz/Biohazard) here in New York. What’s the best writing assignment you’ve ever had?

Comedy Central always took good care of me and gave me great access to talent. I enjoyed rapping with Lewis Black backstage at The Daily Show for a profile I wrote of him. I also got to visit the set of Upright Citizens Brigade and interview Amy Poehler et al. for a profile. I love interviewing comedians.

JNOW: What’s on your plate now? Are you going to expand on your motorcycle-blog?

I’d like to learn how to make money on the Internet. I’ve been traveling on my motorcycle a lot–including a two-month trip through the Deep South last fall during Hurricane Ike, the upcoming election and the economic collapse–and would like to capitalize somehow on my traveling experiences. It’s been hard for me to land national magazine assignments the past two years, partially because freelance budgets are so tight and assigning editors are tougher to crack than ever.

JNOW: What kind of advice would you give young people graduating from school who are looking to become freelance journalists & writers?

Are you feeling lucky, punk? Well, are you? Seriously, if you’re lucky enough to land a writing gig, never turn down advice on your writing or reporting skills. There’s always room for improvement. Don’t get full of yourself. Treat every assignment as if it will be your last if you don’t turn out stellar copy.

JNOW: Thanks Tom for answering our questions!