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Q&A with Jason Zook

Guy who didn’t want to live an average life anymore

My name is Jason Zook, but people may also know me as Jason Sadler, Jason Headsetsdotcom, or Jason SurfrApp. I’m just a regular guy who didn’t want to live an average life anymore. In 2007 I left the corporate world to co-found a web design company and in 2008 I came up with the idea for IWearYourShirt. Over the years I’ve used my creativity to build unique sponsor-driven businesses. What I do these days is create products and content that helps people take action with their lives and businesses.

How did you get started?

I moved around a lot as a kid. I lived in Arizona, California, Virginia, New Jersey, and Florida. All that change growing up helped me become thick-skinned and unapologetically me. When my Mom bought a Gateway Desktop computer (the one that came in the cow print box) in 1996, I was introduced to the Internet. Instead of pursuing entrepreneurship and freelance web design/coding, I went to college to get a degree in Graphic Design. It was probably the biggest waste of 5 years of my life. I wouldn’t change the past, but I didn’t learn anything in college and it pushed me toward corporate America (where I was not a fit). I had a few graphic design jobs after college, but finally quit after reading Seth Godin’s book The Purple Cow. I realized I didn’t want to be a cog in the corporate wheel at any company.

What hardware and software do you use for your work?

I’m a pretty simple guy. I use all Apple products. Macbook Pro, iPhone 6, Mac Mail, etc. I write 500 - 1,000 words daily and recently started doing that in the Letterspace app. I used to use fancy tools, but now I’m a fairly native app guy (Instagram, Twitter, etc). I probably have 20 apps on my iPhone that I actually use. I only have 8 on the home screen. Some products I use and love for business: Mailchimp, GoSquared, Basecamp, Dropbox, and lots of notebooks/journals.

What are you working on now?

Great question. Too much. Hah. I co-founded an online learning platform called It came about after I wanted to try building my own online course in 2014. I didn’t like any of the existing platforms so I built my own. The pricing structure I created for IWearYourShirt in 2009 (1onday1,1 on day 1, 2 on day 2, $3 on day 3) is being turned into a product at I have two podcasts, Invisible Office Hours and Sleeping With The Boss. I write weekly articles that go out to The Action Army,, TheNextWeb, and other places. I have a few other fun projects in the works and will probably write another book this year.

What is your ideal work environment?

Wherever I can be the most productive. Sometimes that means sitting at my clutter-free desk on a yoga ball with a second monitor. Sometimes that means standing in my kitchen using the bar top as a desk. Sometimes that means a quirky coffee shop. I love working in natural light and without a lot of distractions (we have enough of those online). I tend to move around a lot, getting bored of working in one area for too long.

Where are your favorite places for sharing experiences?

Instagram is my favorite social network at the moment. It’s free of crap right now. I can curate exactly what I want with nearly zero interruptions (ads, political rants, etc). Twitter is good for communication. I’m kind of over Facebook at the moment. But my favorite place to share is my weekly email newsletter. I feel like I have the most connection and interaction there. It may not seem like a social channel, but I try to use it that way.

Who are the creatives you admire most?

Seth Godin, Bill Watterson, John Lasseter, Steve Jobs, Paul Jarvis, Jason Fried, Brock Davis, Austin Kleon, my girlfriend Caroline Winegeart. The list is ever-changing and ever-growing. It depends on the mode I’m in. But those are a few off the top of my head.