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Chris Brakebill’s Mac and iOS setup

Every week we post a new interview with someone about what software they use on their Mac, iPhone, or iPad. We do these interviews because not only are they fun, but a glimpse into what tools someone uses and how they use those tools can spark our imagination and give us an idea or insight into how we can do things better.

New setup interviews are posted every Monday; follow us on RSS or Twitter to stay up to date.


Who are you and what do you do?

My name is Chris Brakebill, and I’m a web and mobile developer currently working on an iOS game called Outshape. I also send out the Three Things Weekly newsletter, and was recently a developer at ESPN in the fantasy games department where I worked on Fantasy Football, Basketball, Baseball, and Hockey. Since March, I’ve decided to take Outshape full-time while looking for other opportunities.

What is your current setup?

Chris Brakebill's desk

I do most of my work on either my 13-inch MacBook Pro Retina or my ESPN 15-inch MacBook Pro Retina. I’m tempted by the Retina iMac since I do about 90% of my work from my desk, but having the ability to work somewhere else is crucial to me (like my table out back — this is Florida after all!). I use a Pioneer A3 Airplay speaker for music and podcasts. It’s battery powered, so I can take it with me wherever I go!

Chris Brakebill's desk

I had a standing desk I purchased on Etsy for a long while, but I just wasn’t digging standing only so I bought my current desk and chair from Ikea and turned that standing desk into a bar.

What software do you use and for what do you use it?

I use Fastmail and Mail.app for email and a combination of Calendar.ap and Fantastical for managing my schedule.

I do almost all of my development in Sublime Text. I usually change themes fairly frequently, but I’ve been using cobalt2 for a while. For writing, I use Sam Soffes’ Whiskey Markdown editor. I try to write at least one post per weekday on my website.

I also spend a lot of time in the Terminal running various git, node, and gulp commands. When I’m doing a poor job of committing frequently, I jump into Tower to make finer git commits.

I’m constantly looking for an application and/or system that fits me for managing my tasks. I’ve been using a combination of Bullet Journal in my Baron Fig and Things, but I’m testing out OmniFocus at the moment. We’ve begun using Agile at ESPN, and I’m trying to adapt an Agile sprint-like flow to my side projects.

I follow all of my RSS feeds in Reeder for Mac. I keep my passwords in 1Password for Mac. And I sync basically everything through Dropbox. I use Evernote as a searchable digital storage for documents, articles, and any other information I want to keep, which helps keep my email inbox empty. All of my computers are backed up to Crashplan.

My wallpapers all come from unsplash.com. Whenever I see one in the RSS feed I like, I downloaded it to a folder and OS X just loops through the pictures in that folder.

How would your ideal setup look and function?

My ideal setup would probably involve adding a Retina iMac and a mythical matching Retina display. I’d put all of that on top of an adjustable desk so I could both stand and sit. I’d love that adjustable desk to be made out of some beautiful reclaimed wood rather than the cheap plastic I have today.


What iPhone do you have?

Chris Brakebill's iPhone 6 Plus

I have a 64 GB Gold iPhone 6 Plus. It’s… pretty big. I’m currently trying to sell it and switch to a 6.

What apps do you use the most, and why?

I probably spend the most time in Mail.app. I used to be a Mailbox guy, but I switched to Fastmail, and until Mailbox supports generic IMAP I’ll be using Mail. Anything important gets saved to Evernote and deleted from my inbox. I use Evernote very frequently when traveling.

I use Simple for banking and I love it. It’s probably the single most important service in my life.

I spend a lot of time browsing Pinterest and Houzz looking for inspiration my wife and I’s future home. I’ve been a Reeder user since day one and no app has come close to getting me away from it. I use David Smith’s PodWrangler for Podcasts, which I get for free as a subscriber to FeedWrangler. Rdio is where I get my music, which is mostly a lot of Jamie Cullum. I throw long reads into Instapaper, but I restrict myself to 10 articles at a time. If I get more than that, then I force myself to go through and archive the least interesting ones.

I also have Things and Trello on my phone for keeping track of tasks and a couple of projects. I keep my Three Things Weekly ideas in Trello, so whenever I see something that catches my eye, I toss it in there for consideration. I haven’t sprung for OmniFocus… yet.

Which app could you not live without?

I’ve mentioned how important Simple is as a service, but 1Password is just as crucial. It helps me keep my passwords unique, secure, and always with me.


There are more Sweet Setup interviews right here.