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York barber’s troubled past shapes life as entrepreneur

York barber’s troubled past shapes life as entrepreneur

  • Didi & Smiling John’s co-owner John Shilling embraces the unconventional path that’s led him to where he is today.
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Five years before starting Didi & Smiling John’s Barber and Beauty Shop with his wife, Devon, John Shilling was property of the state of Texas.

As a 17-year-old convicted of federal charges he’d rather not mention, he’d spend the next decade behind bars. It’s where he mastered “jailhouse style” fades, he says, nurturing an early entrepreneurial side by giving straight-razor fades to inmates and guards.

Today in his shop in the Royal Square neighborhood in York, he demonstrates the technique, which involved a contraband razor blade and comb. It’s a part of his life he doesn’t regret. “Honestly, I’m where I’m at now because of the stuff that I did,” he says. “Not everything you do is great and spectacular, but it all teaches you something.”

After prison

When John got out of prison, he came to the York area because of family, met Devon, and took work where he could get it: flooring, construction, restaurants. “All the things that are accessible as a convicted felon,” he says.

He dabbed around cutting friends’ hair as a teenager and eventually learned to use clippers in the prison’s barbershop, so he enrolled in World A Cuts Barber Institute in York to earn his barber license and work for himself.

He bounced around several shops in the region before meeting a guy who owned a barbershop in Schwenksville, a town about an hour north of Philadelphia. He was short on barbers and told John he only hired felons.

“They’re more trustworthy,” the man told him. “They know what they have to lose.”

He convinced John to make the two-hour drive from York and work a shift. He did two cuts all day. The owner told John it was a fluke and gave him $100 to come back tomorrow. John did and made about $600 by the end of the night. He took the job.

“Up until that point, I knew how to cut hair,” he says. “At that shop: I learned how to be a barber.”

‘A better way to do it’

A year and a half later he jumped on an opportunity to sublet a space in North York. He called it Smiling John’s Barbershop — an homage to the nickname he picked up in the Schwenksville shop, where the owner called him “Smiling John” to make him more approachable to customers who found his tattoos and posture intimidating.

In 2011, he and Devon got a space together on South George and officially started their barbershop and salon. They built up a solid book of business and moved their shop in 2014 to the Royal Square location they’re at today.

Things went well until John got into trouble again, landing DUI and possession charges in 2015. A motorcycle crash that left him seriously injured probably spared him a prison sentence. The fear of losing the shop’s reputation scared him more than going back to prison anyway.

Today, he doesn’t drive under the influence, he says. Didi & Smiling John’s is 10 years old, and their business has offered a number of other barbers and beauticians a place to get their start. He’s spoken to kids about his past; the trouble’s not worth it, he tells them.

“I wish I’d known then what I know now,” he says. “There’s different ‘hustles’ out there. There’s a better way to do it.”

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