Jeffrey Smallwood wears a lot of hats. The Tempe-based entrepreneur, tennis coach, wedding photographer, avid traveler and father is constantly coming up with his next project. One might say he’s restless. So, it makes sense that his latest endeavor, a clothing company, is called Restless Brand.
His 3-year-old daughter was the one that initially inspired the name, however. “She has energy for days,” he says. “You think you would run her into the ground with a whole bunch of activities and she’ll pop up ready to go.”
The apparel company’s name also stems from Smallwood’s late-night brainstorming sessions, when he studies how to become a better coach and photographer. He only took two classes for his wedding photography career. “Everything else was basically YouTube University,” he laughs.
Smallwood’s T-shirts are designed to inspire people, spread happiness and start conversations. “The way I see it, [life] is just like playing tennis. In tennis, there’s no timeouts, there’s no breaks, you’re all by yourself and nobody’s going to help you out but you,” he explains. “Whatever happens in your life, you need to think about it, put a smile on your face and figure out a way to turn that frown upside down.”
Smallwood’s T-shirts feature smiley faces with Xs for eyes and bold lettering in a variety of colors and patterns. He says his biggest obstacle will be marketing but believes he will garner organic sales from those who resonate with his story, the logo and the name.
He adds that balancing fatherhood and his various business ventures can be difficult, especially after experiencing a series of setbacks when he was younger, including the death of his mother and deteriorating health of his father. He started side hustles at a young age, selling cookies, candy and CDs to his classmates to make ends meet.
“I didn’t have money for clothes, so I started making my own,” he says. “I would buy cheap pants, rip them up and sew different patches on them.”
Though he admits he performed poorly in his classes, he was a star tennis player and had dreams of going to Los Angeles to play tennis and design clothes. He spent several years sleeping in his car and on friends’ couches. “Everything I ever had in my life is my duffel bag and my tennis rackets,” he says.
After eventually making it to LA, Smallwood caught the travel bug and moved to China for a year to teach tennis. He ultimately settled in Arizona to raise his daughter. When she’s older, he says he hopes to involve her in his T-shirt business. Although she is still young, Smallwood strives to teach her financial literacy though games like Monopoly and Robert Kiyosaki’s CashFlow.
What else does he hope to pass on to her? “Treat others the way you want to be treated. Always look on the bright side of things. It’s not always as bad as you think. And if it is, try to keep smiling,” he says.
Currently, Smallwood sells a slew of short-sleeve T-shirts in different colorways on the Restless website. Soon, he will roll out a winter collection that will include cotton joggers, hoodies, long-sleeve shirts and socks.
His next project will include sunglasses made from plastic waste collected from oceans across the globe, with proceeds benefitting various nonprofits.
For more information, follow Restless Brand on Instagram and YouTube.
