With less than $1,000 and a deep knowledge of Cleveland history, Stephen DiMatteo saw an opportunity in 2021. His love for Cleveland, combined with 15 years of digital marketing experience, sparked an idea – while the city had plenty of modern sports merchandise, no one was telling the story of Cleveland’s past through clothing.
Using personal savings and drawing from his marketing background, he launched Cleveland Vintage Shirts – now a full-time operation celebrating the heritage of both Cleveland and the broader Midwest region through apparel featuring defunct sports teams, old businesses, and nostalgic elements of local culture.
“I wanted to tap into that in a way not typically seen from other brands in the area,” DiMatteo explains. “In my digital marketing experience, I’ve seen the behind-the-scenes metrics for dozens of e-commerce apparel brands, and I’ve worked with other Cleveland retailers in the past, so I knew what kind of demand there ultimately was.”
The launch exceeded his expectations. “I was lucky to get my first sale pretty quickly, as I reached out to local news and radio stations as I launched to do some initial PR,” he shares. “Fortunately for me, I was able to get on the local news and interviewed on a morning radio show, so I was off and running pretty quickly after that initial time investment.”
Still, questions lingered. “Would this actually work? Would I ever make any money? Would people even like my designs?” Rather than letting these concerns stop him, DiMatteo embraced them. “To be honest, nothing truly held me back – I knew it would be a long game to build the brand, and there would be a lot of trial and error.”
To keep operations efficient, DiMatteo uses print-on-demand services for his products. “I usually decide on pricing through researching my competitors and looking at my own costs/overhead,” he explains. “I often use print-on-demand services, so the per-shirt cost is a little higher, but inventory management is much easier/streamlined. That also means I don’t have to worry about storing my products anywhere and dealing with that cost – I’ve been able to scale essentially at whatever pace I want. My POD supplier even takes care of the shipping once the product is ordered.”
Instead of spending money on advertising campaigns, DiMatteo chose to build his brand through organic search traffic – meaning customers find his products while searching online for regional history and memorabilia. He and his father write all the website content together, a partnership that emerged naturally. “My collaboration with my dad started not only because he’s a great writer and Cleveland expert himself, but because he’s nearing retirement himself and is able to devote as much time as he wants to this new project,” DiMatteo shares. “It’s been a tremendous bonding experience getting to work alongside him.”
Startup Stories
This father-son collaboration extends to their YouTube channel (@clevelandvintage), where they share more stories about the area’s past. Both the channel and website content help people discover Cleveland Vintage Shirts naturally, without paid advertising.
“It’s a grind,” DiMatteo admits. “When you start out, you have to envision what the brand will look like five years down the road, and just know that each and every day you are working towards that goal.” Looking back, his only wish is that he had put even more effort into building organic search traffic from the beginning.
For those interested in starting a similar business, DiMatteo recommends specific tools that have helped him succeed. “In terms of essential tools and software, I’d recommend the likes of Shopify, Printful, and most certainly TaxJar to help me stay on top of my sales tax obligations.”
Cleveland Vintage Shirts continues to release new products throughout the year. DiMatteo’s story shows how combining professional knowledge with local passion can create something meaningful, even with minimal startup funds.
His journey offers several insights for others starting a business:
- Use your existing professional knowledge to identify opportunities
- Find ways to grow without expensive advertising
- Build strong partnerships, even within your family
- Connect with your community’s interests
- Start small and stay consistent
DiMatteo’s path demonstrates that starting a business doesn’t require massive funding or revolutionary ideas. What matters is understanding your market, working consistently, and connecting with your community. Whether you have industry experience like DiMatteo or simply a passion for serving your community, success begins with taking that first step toward your vision.
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