Hello, Mr. Ambassador: Bugsy Sailor promotes the Yooper lifestyle like it's his job

Meet Bugsy Sailor. He loves the Upper Peninsula. So much so, he's taken it upon himself to let the world know what a great place it is to live and play. 
When the word "Yooper" is brought up and folks do their best to conjure up an image, it probably isn't so far-fetched that they would think of a lumberjack of old, dressed in red and black flannel, sporting a full beard and wearing a trusty ol' Stormy Kromer atop their head.

Hold that image in your mind, add in a fun personality, a drive to promote the Upper Peninsula as a true ambassador of the region and someone who is always in a Superior State of mind and you'll have a solid base for describing Bugsy Sailor to someone who has never met him.

Sailor is the 32-year-old founder of a slew of properties, but most notably Yooper Steez, Plaidurday and some inventive April Fool's jokes like Yooper Singles and even Lake Superior shark sightings.

"It has all been a lot of work," Sailor laughs as he tips back a pint of Blackrocks Brewery suds. "It's fun, but it's a lot of work."
That labor is definitely grounded in love. Sailor, who grew up in Baraga and graduated from the high school there before departing for Michigan State University, is a firm believer in promoting the Upper Peninsula and all that it offers. It all started when he went on a 50-state tour following his graduation from MSU.

"I found the farther away from the Midwest as I traveled, the more and more I had to explain where the Upper Peninsula was and what it was like," he says.

Although he had spent plenty of time explaining to fellow Spartans that Yoopers weren't the stereotypical, backwards, backwoods people that everyone thought they were, the tour across the U.S. was Sailors' first real experience as an ambassador of the U.P.

That trip also became the spark that set fire under Sailor to create Yooper Steez, arguably the first apparel company to push Yooper-themed shirts to the world at large and not just tourists stopping for a roadside break. Since he first started the company in 2008, Sailor has shipped shirts to every state in the Union, to a large portion of the countries across our wonderful world and he has been sent photos of fellow Yooper representatives sporting the threads on every continent on the planet -- even Antarctica. From the familiar outline of the U.P. emblazoned on a shirt to the 906 stickers that seem to be on everyone's cars these days, Sailors ideas caught fire with the Yooper faithful.

"It's been pretty amazing," Sailor says. "In 2007 when I first came up with this idea, I never really thought about how big it might get."

And it just keeps growing. From its roots of being the purveyor of Yooper-themed apparel that was meant to instill pride in the Upper Peninsula, Yooper Steez has grown into more of a dual role. The selling aspect of the site is ongoing, and doing well, but the social aspect has brought in its own congregation of loyal supporters.

"I'm proud of the role the blog plays," Sailor says. "It's a voice here in the Upper Peninsula."

Sailors' ideas getting bigger than expected is starting to become a bit of a theme. His Plaidurday concept has really taken off and this past year's event had Marquette looking like a classic lumberjack convention was in town. But it was his Yooper Singles -- an April Fool's joke website he created in 2014 -- that really caught fire across various media outlets. On the first day, more than 1,000 people had signed up for the relationship site.

"That was just -- I definitely didn't expect that," he says.

And his ideas don't stop there. Have you seen the hashtag #906Life on Twitter? Yeah, that's him. That fake push to rename Lake Michigan as Lake Wisconsin? Yup. The designation as Sept. 6 as 906 Day? MmmmHmmmm.

Sailor, who's "real job" is the director of digital at Marquette's world-class creative agency Elegant Seagulls, has a whole slew of ideas bursting to get out and into the world. What are they?

Sailor smiles. "I drive my friends and coworkers crazy with the secrets I keep. I tend to hold things pretty close to my chest."
Secrets may abound when it comes to his future plans for Yooper domination, but Sailor is quite open when it comes to his choice to walk the walk of the Yooper lifestyle. He spends most of his available free time outside, from snowboarding to hiking to carrying a camera with him and snapping up moments of life -- though not hunting or fishing. Heck, Sailor can even be found perfecting his rock-skipping capabilities for his next appearance at the sport's world championships, held on Mackinac Island annually.

"I've always loved skipping rocks," Sailor says. "It was actually the blog that got me connected (with the world championships). I had posted a video of the world record for skipping and the guy who holds the record saw it and contacted me."

It was then that Sailor found out about the opportunity to throw for the world championship title, and that it was here in the Upper Peninsula. Last year, with 22 skips off his throw, Sailor took home the amateur title. While he hasn't captured the professional world championship trophy quite yet, Sailor says he is far from discouraged.

"Oh, I love it," he says. "It's so much fun."

And fun is what Sailor seemingly does best. His Facebook feed has random contests to win items like a free Stormy Kromer cap, and Yooper Steez will occasionally announce a drop of their product for some lucky passerby to find and own.

Sailor is a true emissary for the Upper Peninsula, and one that many other business owners and social media sites could learn lessons from. The first? Don't worry, it's nice and easy.

"I just want people to see the Upper Peninsula the way I see it," Sailor says. "It's beautiful up here. The people, the places -- they're all great. And I'm discovering new things every day. Even with all of my adventures, I've not seen most of what the U.P. has to offer. I can't wait to see more.

"This is a great place to live. It's a great place to visit. It's full of great people. What's not to love about the Upper Peninsula?"

Well said, Mr. Ambassador. 

Sam Eggleston is the managing editor of U.P. Second Wave. He was born and raised in Michigan's Upper Peninsula and has been known to rep the Yooper lifestyle at comic cons, various sporting events and anywhere a White Castle can be found. He can be reached via email
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