The Rise: From Homelessness to Entrepreneurship

POSTED ON February 21, 2023 BY Justine Smith

Behind the welcoming demeanour and warm personality of Matthew Romeo, is a man who overcame hardships to become the owner of a business nestled in The Tower Building, at 110 Spadina Avenue, unit 105. We sat down with the multi-talented entrepreneur and owner of My Dope Tee, to discuss his custom apparel business, which turned out to be a fascinating journey through his life experience. From living on the streets, to mentoring youth at the Toronto Kiwanis Boys and Girls Club, to spinning records for big names like Michael Jordan, to now building a successful business, Matthew shared lessons and inspiration that took him through these chapters of life.  

My Dope Tee was born out of a need Matthew discovered when looking for a custom apparel company that provided great customer service, high-quality product, and fast turnaround time. Matthew sought out to fill this gap in the custom apparel industry and created a solution of his own. “My Dope Tee is a solution for creative entrepreneurs who want to monetize or bring their creative ideas to life,” said Romeo. Through the company’s website, customers can access the easy-to-use online designer to customize more than 3,000 items such as t-shirts, hoodies, hats, tote bags and backpacks. Designers and creators can take advantage of the e-commerce platform and enlist My Dope Tee to co-manage their online custom apparel businesses. This allows entrepreneurs to focus on sales and promotions while My Dope Tee handles production and fulfillment.

“Most recently we’ve added a photo studio, offering amazing product shots and headshots. I like to be resourceful and help our clients with things they may not be able to typically find at a print shop. What print shop has a photo studio? We want you to look like a star after you get your merch!”

The company also plans to launch a fundraising platform to help charities, non-profits and independents raise money through selling their custom apparel. 

Prior to his apparel business, Matthew faced challenging times struggling with homelessness at a young age when he moved to Toronto with a pocket of change and two bags of clothes. Despite this, he persevered, remained hopeful and maintained a strong sense of self-worth. He now uses his personal experience to connect with others and recently spoke at a workshop for individuals incarcerated. 

When I think about it and look at the impact that my life has had on others, it’s a blessing in disguise – having the intention of sharing positive messaging with people and then life hits you with the experience. I can actually talk about being homeless and understand these kinds of mindsets.

Matthew credits his mom for inspiring his level of drive, sharing that, 

She came to this country with nothing, from the islands, and made a pretty great life for herself. My mom was always very kind and wanted to support people. As I go through life, I’m thankful I have a mindset that allows me to keep going. I think mindset is very important in anything you do – having self-belief and self-worth, even though sometimes things can be hard and discouraging. One thing I learned a long time ago is that the world might be against you, but you can’t be against yourself. Once you’re against yourself, you’ve ultimately lost.

His advice to the local business community was to help generate support for community members struggling with homelessness. 

It’s not just the business community alone, it’s also government, resources, funding, housing. About a block from my business is transitional housing called Eva’s Phoenix. I lived at Eva’s Phoenix for a year and that helped me get to my next step in life, to be able to get into a place of my own and do what I’m doing today. I think if there was something I could say to a business owner, I’d say, you may not have the answers right now, but do your best to be open minded to learn something new. Continue to push your community leaders or even leverage your business itself, to see if you can get more funding, or bring more awareness to the resources that are literally around the corner. Homelessness and drug use aren’t good for our communities or businesses. But if we could help create and facilitate more solutions to help reduce this, it’s going to help everyone overall.

Matthew’s story is one of never losing faith and ultimately triumphing against all odds. He attributes his business success to the support and loyalty of his customers. “All of my clients are important to me, even those who don’t order anything. We want people walking away with a great experience, a great product and a big smile on their face. That’s our main goal.