Noted Interviews: Dave Caolo

The tech space is full of creative people, exciting projects and interesting products. With Noted Interviews, we tap into the brilliant minds of the individuals behind such works, letting you know why and how they do what they do as well as giving you a better insight into who they are as people.

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Who are you and what do you do?

My name is Dave Caolo and I’m the co-founder and Editor-in-Chief at Apple World Today, a website about, by and for the people who love Apple’s products and services. I also co-host a podcast about working from home called Home Work for the 5by5 Network, along with designer Aaron Mahnke

How did you get into writing? What were your inspirations and what came before?

I fell into it, honestly. Many years ago I was working as the IT director for a Mac-friendly residential school out here on Cape Cod, Massachusetts. That job required me to stay current on hardware and software that was pertinent to my job. Not only did I maintain our file server and backup server, I served as “help desk” for forty some-odd Macs and their users. 

I was always reading, and The Unofficial Apple WeblogTUAW — was one of my main sources. One day they put out a call for bloggers, I applied and got the gig. As you could imagine, I was elated. About a year later I went full-time as managing editor. Interestingly, that was not my first paid writing gig. I had been contributing weekly articles to The Parenting Post, the now-defunct official blog of Parenting Magazine.

Your previous employer AOL recently decided to shutter The Unofficial Apple Weblog — a site you were at for almost 5 years — as part of a broader reshuffling. Did this come as a surprise to you and other TUAW staffers?

"Business is business...That's how it goes sometimes."

It was a surprise and disappointing. The people I worked with at TUAW over the years were top-notch. Super smart and motivated folks. They all showed up and did a great job every day. But business is business and the bottom line is the bottom line. That’s how it goes sometimes.

Following TUAW’s closure, yourself, Steve Sande and Kelly Hodgkins have started a new Apple-focused blog in Apple World Today (the future of which I’m incredibly excited for). Is the site a continuation of TUAW in some respects or do you plan on doing things a little differently?

I guess it’s natural to think of Apple World Today as “TUAW II,” but that’s not our intention. We want to keep doing what we’ve been doing, so we’re making that happen. Some aspects of AWT’s daily functioning will be similar, as we’re covering the same general topics: Apple-related news, reviews, tips, how-tos, opinion pieces and so on. But now that we're not beholden to a parent company, we’re free to try new ideas and implement them right away. For example, we mean to do video reviews and set up a forum. It’s going to be fun.

Having moved from operating under a large corporate boss to being wholly independent, how will the writing, production and publishing process differ for AWT?

The process will remain the same, but the implementation will change out of necessity. At TUAW, we had a fantastic system for making assignments and getting them written, reviewed and published in a timely manner. Review procurement and management — hardware and software — also worked like a well-oiled machine at TUAW. Fortunately, I’ve got Steve Sande, our old hardware review editor, and Kelly Hodgkins, our former apps review editor, on the team. We’re used to working with other so there won’t be a transition as far as expectations, style or performance goes. 

However, the tools have changed. We formerly used IRC as our virtual “office,” with several automated bots in place that handled various aspects of the workday. They’re gone now, and we miss them. Also, we’re using a new CMS. AOL’s proprietary blogging system was nice and I do miss it. We’re working out those changes as we go, so it’s challenging. 

Outside of writing, you also host podcasts. Podcasting seems to be experiencing something of a renaissance at the moment — what do you make of the mainstream dialog surrounding the medium?

It’s amazing to me that it’s been embraced so fully. Not by the consumers specifically, but by high-profile content producers. I first noticed this when the re-worked Battlestar Galactica was airing on the Syfy network. Every week, a new episode of the show’s official podcast would come out with writer Ronald D. Moore and various guests who provided what essentially was a commentary track for the week’s show. I thought, “These folks don’t have to do this for promotion, the show’s a hit. It must be for the love of doing it.” Today, the promotional podcast is often an aspect of a marketing plan, but I see more and more stand-alone shows that are little business ventures on their own. It’s an exciting time.

Tell me a bit about your current setup. What tools do you rely on to get your various jobs done?

Sure. Every article I write begins as a mind in MindNode Pro. Mind mapping is my favorite way to brainstorm and record the results. Nothing’s off limits when I’m making a mind map. The goal is to get everything down. Once that’s done, I write an outline in a notebook. In that process I’ll eliminate some of what’s on the map, and maybe fiddle with other bits. Whatever I think will work for the article stays. The next step is the first draft which I always write in Byword. I also use Markdown when writing. I let first drafts sit for a day or so, then I give them a re-write until I’m happy. From there, it’s got a date with the CMS and the “Publish” button. 

As for Home Work, Aaron and I share a Google doc where we share topic ideas. Once we agree on one, we collaborate on an outline and research and it’s time to record. We talk over Skype and both use Quicktime to record our audio locally. I use a Rode Podcaster mic on a boom stand, and I think Aaron uses a Blue Yeti. Once we’re done, I marry the two files in Garageband, export to AIFF and then run the result through Levelator. Next it goes into SoundStudio for some final fiddling, and then I share the episode with Aaron via Dropbox, and he adds it to the 5by5 CMS. 

My current computer is a 2010 MacBook Air that is starting to feel its age. I love it, but it might be time to buy a replacement.

With Home Work and Unclutterer, you talk often about scheduling, planning and organization — how do you keep everything in check? How do apps and technology fit into that process?

Apps and technology rule this process! My project/task manager is Todoist. It’s nearly ubiquitous, effective and yes, pretty. I’ve tried many project managers, and for some reason Todoist just seems to fit. I also almost always have a notebook and pen in my pocket, as it’s so easy to jot something down. I can move it into Todoist at the end of the day when I’m “processing ‘in’.” That is to say, looking at all of the “stuff” that arrived in the last 24 hours and deciding 1.) What it is 2.) What I need to do (if anything) and 3.) Where it needs go be. It’s pure David Allen and so very effective.

What tech are you most excited for over the next twelve months?

If you had asked me six months ago, I would not give the answer I’ll share today: Apple Watch. At first I thought it was going to be a marginally useful plaything, but as I'm starting to see what developers are going to do with this thing, I'm getting more excited. I suspect it will change things in a real way.

What does 2015 hold for Dave Caolo, Apple World Today, Home Work and all of your other projects?

Prosperity, hopefully! Aaron and I have been at Home Work for four years now, and I think losing my job is going to be great for the show. It’s always been Aaron the self-employed freelancer and me the telecommuter. Now, I'm in a position that so many of our listeners experience: starting over. I’m the newbie home worker who is literally days into building what I hope to be a life-sustaining business from nothing. I’m not holding back, either. Listeners will get an earful of the successes, failures and “I have no idea what I’m doing” moments. It’s nerve-wracking for me, but great radio!

"At AWT, we’re going to work like dogs to make something fantastic."

At Apple World Today, we’re going to work like dogs to make something fantastic. I want people to think of us when something new happens or big news breaks. “Wow! I can’t wait to see what Steve, Kelly and Dave have to say about this.”

Where can people find out more about you and your work? 

I tweet a lot at @davidcaolo, so that’s a good place to reach me. And of course, Apple World TodayUnclutterer and Home Work