Side Hustle School Ep. 3361 - STORY: Designer Earns $1 Million Giving It The Old College Try
Mar 15, 2026
A designer missing his Southern roots builds a nostalgic line of pennants and tees celebrating hometown pride. A viral blog feature and social buzz send waves of orders and fuel rapid growth. He scales with low upfront cost, packing parties, and customer-driven designs while keeping his day job.
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Designer Moved North Then Built Southern Memorabilia
- Micah Whitson moved from the Deep South to Boston and missed his home community, which inspired him to design Southern-themed pennants and shirts.
- He partnered with a friend who ran a print shop in Somerville and launched The Old Try as a side hustle in 2011.
Design Blog Feature Turned A Small Launch Into Thousands
- The Old Try launch got a big boost when Design Sponge featured the site, driving over 20,000 page views and thousands of orders.
- Micah and his wife held a packing party with friends to fulfill the first 100 orders, turning the spike into momentum.
Visual Products Plus Social Platforms Amplified Growth
- Photo-friendly merchandise and rising visual platforms like Pinterest and Instagram amplified The Old Try's reach through organic shares.
- Customer suggestions shaped new designs, leveraging passionate hometown pride as free product research.