10 min 31 sec

Designer Makes $1M Giving It The Old College Try

Missing the south after migrating north to Boston, a designer creates a series of sports-themed pennants and t-shirts that put hometown pride on display. Since starting up, he’s had more than $1M in sales and earned a profit of $5,000 each month.
High Profit Manufacturing Product Tribal Identity

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What It's About

A designer gives a side hustle the ol' college try and makes a clean million.

Business Model
Skills Required
Design & Experimentation
Profit Potential

Words of Wisdom

If you've got an idea, figure out what you need to make it real! For Micah, he knew he wouldn't treat The Old Try as legit if he didn't make it legit. So they incorporated and opened a bank account, trademarked their name and logo, and got business cards. Micah spent 70% of their startup dollars just on apparatus that made it seem like a business. He was sitting there looking at $5,000 worth of legitimacy and knew that he needed to justify that by creating something great.

Fun Fact

There are 19,354 "incorporated places" in the US. An incorporated place is a government unit such as a city, town, village or borough. Each of these thousands of places has people that call it home and have a sense of attachment to it. Currently, The Old Try only has designs for 150 of incorporated places in the USA. Which means that gives them plenty of room to grow!

Notes from Chris

Episode 649
Micah Whitson had spent his entire life in the south. He’d never set foot any further north than the Mason-Dixon line—that is, the line separating the southern states from the north and the mid-west. By the time he got married, he felt he needed to experience something new.

He and his wife decided to pack up the car and head north, beginning a new life with his skills as a designer. They ended up in Boston. It was a world away from what he knew, but they settled in well. He landed a job as the creative director with a large health company.

But, although Micah had left The South, The South had never truly left Micah. He knew that it was a part of his spirit, a piece that would be with him forever. But it wasn’t until 2011 that Micah realized just how important that piece was to him.

It was that year where some of the worst tornadoes on record ravaged the region. Particularly, Micah’s home state of Alabama. Watching the devastation unfold from afar made him long for a connection to home.

But where would he find it?

After thinking for a while, Micah was reminded of the types of flags and clothes people wore to their college football games. Those colors, taglines, and symbols could bring a sense of community.

Then the penny dropped. He was a designer, and he had a friend who was a printer! He decided he’d create posters, pennants, and t-shirts that symbolized schools and towns of The South. He’d recapture the magic of the old college football games. In turn, the spirit and the camaraderie of the southern states would be on show in the designs of these products. It would be his first side hustle … and as you’ll hear, he turned this overtime project into a self-made championship.

He decided to call it The Old Try, named from the expression “The Old College Try," which means to give something your best shot, even if the odds are against you. Coincidentally, the same attitude you need when starting a project like this of your own.

In terms of financial success, The Old Try has won the Heisman trophy! Since starting in 2011, Micah has generated over 1.5 million dollars in revenue and, after all expenses, generates around $5,000 in profit every month. This has all been built on a foundation of just $7,000 in investment and all while Micah has continued to work a day job.

Looking forward, he sees a clear road to franchise expansion. The Old Try currently has designs for a small fraction of the total areas of the United States—about one hundred and thirty different incorporated places in the US. There are thousands more, so an obvious growth channel is to expand that range, promoting hometown pride across borders.


  • The Old Try: Learn more about Micah's successful side hustle over on his website!

  • Design*Sponge: The blog that resulted in over 20,000 page views and thousands of dollars when Micah went live with The Old Try


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Faulkner said to write what you know. Old Try started that way. By writing and designing Southern things for folks who lived in and out of the South. Things that connect people to a place they go to in their dreams, or a place they could never convince themselves to leave."
—Micah Whitson #SideHustleSchool

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