The T-Shirt Designer Inside Me

Recently I was invited to sit in on a business startup meeting at a local Starbucks. While brainstorming with the founder, the seasoned t-shirt industry guru turned to me and said, “You must have a little t-shirt designer inside you.”

In high school and college I used to make t-shirts by writing on white t-shirts with red markers. I’d write inside jokes  like “Forks, Knives, and Spoons” or movie references like “She’s All That” with a giant arrow pointing to my left.

In 2007 I briefly considered starting a t-shirt business before going into web design with Telablue. “The problem I never addressed with you was the fierce pushback I got from my wife as soon as I discussed our plans for her business. That is why I didn’t follow up with the T-shirt idea and switched to Telablue,” I emailed my friend, Jason on 10/19/2007.


Jason was one of my friends in high school and throughout our adult lives we’ve maintained our friendship thus far. I’ll get to the ‘t-shirt designer inside him’ later on in this post, but for now let’s keep going with the ‘t-shirt designer inside me’.

While sitting at my job at work or driving my daily commute I’d come up with t-shirt ideas and email them to my friends. On 9/28/2010 I had an idea for a “Picture of flux capacitor with ‘Capacity for Change’ written underneath.” Not good.

I started designing t-shirts almost as soon as I started learning about computers. This t-shirt blank is from 12/15/1996. I used it to design t-shirts for my local high school church youth group, which we called “SOTE” (Salt of the Earth).


Not long after, Jason and I formed the band, Shog, and so ideas for making Shog t-shirts soon followed after. This “Make a Joyful Noise Unto the Lord” Shog t-shirt idea is from 4/7/1997. It was designed by Jason, but never got printed.


Jason and I weren’t the only one of our friends to get into the t-shirt design business. My friend Derek, came out with the “Jerk Club” in 12/27/2008. It only had 2 members, who are featured here in this self-deprecating picture below.


In 2010 I had the t-shirt design bug again and designed two shirts. This “Wheat Action” one is Settler’s of Catan inspired and is from 12/12/2010. I actually had this t-shirt printed, but gave it as a present to a friend who played Catan with us.

This “Wisconsin Venn” t-shirt idea is from 12/29/2010 and features the state of Wisconsin at the center of a Venn diagram featuring cheese, meat, and beer. I finally ended up traveling to Wisconsin a couple of years ago with Jason. Fun times.

Before I get into Jason’s t-shirt design business, here’s one more t-shirt design from 7/21/2013 titled, “Sandwich Lover”, which was never printed. I do love sandwiches and have often played with the idea of starting a sandwich blog, but have not. 1/2/2016 UPDATE: This “Sandwich Lovers Sandwich” t-shirt is now available on Amazon.


High Five!

This is a history of High5, a t-shirt project Jason started in December of 2012. Here’s a gallery of the initial t-shirt ideas:

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And here is the final shirt:

Yellow Logo - Front

We’d meet up at local Broad Ripple restaurants and walk along the Monon to discuss t-shirt and business ideas. High5 was more than just a t-shirt company, it was a belief about:

  • Activity – Set goals and meet them. Make things better. Smile. Explore. Take time to enjoy life.
  • Community – Organizing. Lending support. Knowing your neighbors. Believing in each other.
  • Truth – Serve people. Be true. Hope. Refreshment.
  • Be Positive – Peace. Expect the best. Be cheerful. Glass half full – of awesome stuff.
  • Beauty – Stars. Sky. Sunrise Sunset. Smile. Kids’ laughing. The trail.

In a lot of ways, High5 was a reflection of Jason’s values. He likes to set goals and smile. He knows his neighbors. He serves other people. He loves his family, takes them to watch the stars at night, and walks with them on the trail through life.

Although the website is no longer up, the Twitter account @wehigh5 still exists. It says, “We want to be there when you reach the top, cross the finish, & meet the goal. We believe in positive change, saying hi to strangers, and making things better.”

What Did Jason Learn from High5?

It was a learning experience for Jason who said, “I was naive in thinking there could be limited inventory. With different sizes, different color shirts, and men and women sizes (and maybe children) the sku’s expand dramatically.”

Despite getting accepted into Cotton Bureau, he couldn’t garner the necessary votes to get them to go to print, but he did end up printing them locally in Indianapolis and sold them on his own Shopify ecommerce store.

“The amount of effort to get true good quality from a printing partner is remarkable – as I’ve been able to re-confirm with Sycamore,” which is Jason’s latest business on bible print art for the modern home.

High5 was more than just a t-shirt business. It was about saying ‘hi’ to strangers, digging deep with each other, and encouraging each other. “There’s a real sense of pride that swells within me when one of my friends wears a high 5 shirt.”


Update as of 9/2/2019: I now make custom t-shirts as a service for others in addition to the funny t-shirts I make for myself.