ImagiNation with Garrett Massey


Garrett Massey

President + Owner + Founder, Eyesore, Inc.

Occupation: President / Owner / Founder / Big Cheese @ Eyesore, Inc.

Favorite Productivity Tool: Really excited about Accelo – we transitioned to Accelo as our Service Operations platform a few months ago and it has had a huge impact on our business.

Most Recommended App: LastPass.

Last Thing You Read: Recently finished the Chronicles of Barsetshire by Anthony Trollope.


Twitter or Instagram handle: I, admittedly, use neither.

Tell us about your journey? Professionally - I started working when I was 15 in a bank vault. While in college I worked construction and as a server in a restaurant. I graduated from Georgia Southern (the REAL GSU) in 2006 with a BS in Computer Science. I started taking Masters courses while working for the school full time in a development lab, and decided to forego sleep and pick up freelancing development jobs. I founded Eyesore, Inc. in 2007 and relocated back to my hometown on Griffin (about an hour south of ATL) shortly thereafter. Since then, we’ve developed projects for Coke, The Home Depot, United Healthcare, the military, the DNC, a few local governments, and a slew of SMBs & NPOs. My role presently is mostly biz dev and partner relations.

Personally – I have an amazing wife, Alycia, and two kids – Alex (14) and Emmalyn (6). Alycia and I enjoy traveling as often as we can (thanks to some really awesome grandparents who love to babysit) and eating literally anything we can get our hands on (checkout my Facebook – 97% food porn... and smart ass memes).

What's your favorite part of your day? Easily the early AM. That sacred hour or so before kids wake up and emails start coming in is the most productive part of my day.

When do you feel most successful? My team calls it “Friday afternoon Garrett”. Its not always Friday afternoon, and not every Friday afternoon qualifies, but those weeks when you’ve solved some problems, closed some deals, met some new folks, launch some projects, and had fun – that’s when I feel successful.

What do you do to recharge when you’re feeling drained? Create something. I like to cook and recently began brewing beer. It is refreshing to me to be able to create something concrete (we build software, so… not often tangible) and see a finished product.

What do you know today that you wish you would have known when you first got started as an entrepreneur? Ya know – I have often wondered if, knowing what I know now, I would have started my own business. Not because it's not worth the time and effort, but because “ignorance is bliss”. There are certainly tactical things I wish I had know – manage AR better, develop a recurring revenue model, etc. but, overall, its probably a good thing I didn’t know then what I know now!

How do you optimize your day? By understanding a little about timing, and my own makeup. I try to allocate early morning for my critical thinking tasks – when I am the freshest and have the easiest time concentrating, and afternoon for social and creative tasks – when I am more relaxed and less likely to hyper-focus.

Who is the person/people who allowed you to imagine more? Definitely my wife, Alycia. She not only supports me but pushes me to accomplish greater things. My business is important to us, but my goal has been to use my business as a tool to be able to enjoy my family and my life as much as possible. I don’t always hit the mark, but I’m trying!!

What does imagining more mean to you and your story? It means continual improvement. Always trying to do better. Not doing stuff the old way if there is a better way. Being open to ideas. Encouraging discussion.

If you could do more of one thing every day what would it be? Recently heard Kat Cole present, and she called it “finding your water”. What is the one most important thing you can do that will have an exponential effect on your life/business/relationships/etc. Whereas I think it can change, currently I think my “water” is being intentional. Communicating, interacting, and engaging with my wife, kids, coworkers, clients, and partners more intentionally.