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Designer Earns $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 earned more than $1 million.

09:04

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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.

The first thing Micah needed was a series of designs that captured the heart and emotion of people from the south. To find those designs he drew on his own experience. He'd lived in four of the southern states and felt he could represent them well. He took common phrases and images from the areas and began to design posters and pennants including them.

Before long he had a handful of designs that were all his own. Everything was printed and made at his friend's shop in Somerville, just outside of Boston. To showcase them, he built a website. With the site up, and the designs ready to go it was time to throw a Hail Mary pass and work on some promotion.

Micah wasn't expecting much when he launched the site. He sent out a few emails to prominent bloggers to inform them of the site and what he was trying to achieve. As luck would have it, a small blog called Design Sponge picked up the story. This was no small thing, the blog receives over 700,000 daily readers so things were about to get real for Micha and The Old Try website.

That one feature resulted in over 20,000 page views, thousands of dollars in orders and most importantly was the kickstart he needed to fully dive in. Micah and his wife celebrated by inviting some friends over for a packing party to get the first 100 orders out.

Now, you could put that launch down to luck, but Micah felt it was the concept that resonated with people. Again, a shared sense of community.

Remember, this project started in 2011. The side hustle was coming of age at the same time as Pinterest and Instagram. Plus, the types of products Micah creates are extremely photo friendly and likely to be shared. Over the months and years, some of Micah's posts have gone viral and have even been shared by celebrities such as Russell Simmons and Reese Witherspoon. This has helped to drive further growth and increase sales.

In addition, further growth has been fueled by new designs and suggestions from customers. People from the south are passionate about where they come from and more than willing to email Micah ideas for new products. The feedback he receives influences the types of products that get released on The Old Try website.

In terms of financial success, The Old Try has won the Heisman trophy! At the time of our story, Micah had generated over 1.5 million dollars in revenue, and the business was profitable. 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 to go, so an obvious growth channel is to expand that range, promoting hometown pride across borders.

Listen to today's episode to learn more...

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Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

[Music]

Designer earns $1 million, giving it the old college try. Welcome friends, welcome to Side Hustle School. Let's talk about hometown pride. Well, we're gonna talk about that in the context of a side hustle, of course. A guy who was missing the South after migrating North to Boston, he goes out and creates a series of sports themed pennants and t-shirts that put hometown pride on display.

And since starting up, he's earned more than a million dollars. We're gonna talk about how he made it happen, what you might learn along the way, how this might inspire your own extra income project, perhaps your next small business idea even, who knows. And as I was working on this story, like I'm not a big football fan myself, but I'm well aware of like the fanatical tribalism it can attract, which of course lends itself to merchandise of all kinds. I used to live in Alabama for a few years as a kid and teenager. And there was this big football team rivalry between Alabama and Auburn.

And there was a store in the mall where I used to go as a kid. Well, I went to the mall, I didn't really go to the store too much, but the store was called the Alabama Auburn store. And it was like 50% Alabama merchandise and 50% Auburn merchandise. And now that I have some experience in entrepreneurship, I'm like, what a great idea. Like those guys are the real winners.

Who cares which team you like, I'll sell you a jersey either way. I'm not sure what happened to that particular store, but perhaps this guy today is kind of following in those footsteps and taking it his own direction, of course. Let's hear the story of Michael Whitson. I'm excited to bring you this one. It's coming right up.

[Music]

Michael Whitson had spent his entire life in the South. In fact, he had never set foot any further North than the Mason-Dixon line, that is the line separating the Southern States from the North and the Midwest. By the time he got married, he felt like he needed to experience something new. So 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, a world away from what he knew, but they settled in well.

He landed a job as the creative director with a large healthcare company. But although Micah had left the South, the South had never truly left Micah. He knew that it was part of his spirit, a place that would be with him forever. And then one day, Micah realized just how important that piece was to him. This was way back in 2011, actually, when 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 he was reminded of the types of flags and clothes people wore to their college football games. The colors, taglines, and symbols could bring a sense of community. And then the penny dropped because he was a designer and he had a friend who was a printer.

He decided to create posters, penance, and T-shirts that symbolized schools and towns of the South. He'd recapture the magic of those old college football games. And in turn, the spirit and 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're gonna hear, he turned this overtime project into a self-made championship.

He decided to call the business The Old Tri, named from the expression The Old College Tri, which means to give something your best shot, even if the odds are against you. Coincidentally, that's the same attitude you need when starting a project like this of your own. The first thing Micah did was a series of designs that captured the heart and emotion of people from the South. And to find those designs, he drew on his own experience. He had lived in four of the Southern States.

He felt like he could represent them well. So he took some common phrases and images and began to design posters and penance, including them. Before long, he had a handful of designs that were all his own. Everything was printed and made at his friend's shop in Somerville, just outside Boston. And to showcase them, he built a website.

Micah wasn't expecting much when he launched that site. He sent out a few emails to some bloggers. This is going back a ways when bloggers were more influential than TikTok. TikTok didn't actually exist. He sent out those emails to inform them of the site.

And his luck would have it, a blog called Design Sponge picked up the story. That was no small accomplishment. The blog received 700,000 daily readers. So things were about to get real for Micah and the old Try website. That one feature resulted in over 20,000 page views, thousands of orders, and most importantly, was the inspiration or the push he needed to fully dive in.

Micah and his wife celebrated by inviting some friends over for a packing party to get the first 100 orders out. Now you could put that launch down to luck, but Micah felt it was the concept that resonated with people. Again, a shared sense of community. The site also was coming of age at the same time as Pinterest and Instagram. Also the types of products he was making were extremely photo-friendly and likely to be shared.

Over the months and years since, some of Micah's posts have been shared by celebrities such as Russell Simmons and Reese Witherspoon. This has helped to further drive growth and increase sales. Also, he has added new designs based on suggestions from customers. People from the South are passionate about where they come from. They're more than willing to email Micah ideas for new products.

And that feedback he receives influences what gets released on the Old Try website. Now, in terms of financial success, I already mentioned this in the introduction, but the Old Try has won the Heisman Trophy. That just means it's doing pretty well. At the time of our story, which was a number of years ago, Micah had generated over $1.5 million in revenue. The business was profitable and it all been built on a foundation of just $7,000 in investment and all while Micah continued to work a day job.

That's pretty cool, right? And also at the time of our story, the Old Try only had a small fraction of total areas of the United States designed. So he had about 130 different incorporated places. There are thousands more to go. So an obvious growth path is to expand that range, promoting hometown pride across borders.

[Music]

Well, as I said, Micah got a little bit lucky, perhaps with that big mention from DesignSpunge, a popular blog, but he took the luck and improved upon it. He went from those first 100 orders to thousands of orders. He continued to add designs, improve the process, reach out to other folks. So sometimes luck is a little bit of a catalyst and then it's like, what are you gonna do with it, right? If you get lucky, consider what you're gonna do with your luck.

And I think this is just such a wonderful business. It's still up and running, of course. I don't know how many designs he has now, but he is still going strong. So I hope this is a point of inspiration to you listeners. And as always, inspiration is good, but inspiration with action is so much better.

So I hope you'll not only be inspired, but go and do something for yourself and consider what can you make. How can you build something that will create financial freedom for you, allow you to do more of what is important to you, and maybe even bring some joy to others along the way. That's what it's all about. At least that's our mission. Detailed archives of 3,200 plus episodes, completely free, available for download or streaming at sidehustleschool.com.

Thank you for listening today. My name is Chris Guillebeau. This is "Side Hustle School." [Music]

- From the Onward Project.

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