Bugsy Sailor

Hometown Invasion Tour

Upon finishing his undergraduate degrees from MSU in 2006, he aimed to incorporate his two degrees—advertising and sociology—and his interests in web design, photography and journal writing into a single job.

On September 8, 2006, Sailor embarked on the Hometown Invasion Tour sponsored by Jeep. The Hometown Invasion Tour was a road trip across the United States where Sailor lived with a different family in each state as he documented hometown life through photography, interviews, and journaling. The aim of the trip, Sailor stated in interviews, was to prove the American spirit was still alive. In 375 days he succeeded in visiting all 50 states, staying in over 100 households, using 1,251 gallons of gas and traveling a total of 29,403 miles. After the trip, he declared that he was the Upper Peninsula of Michigan's "Official Unofficial" Ambassador.

Sailor has spoken about the Hometown Invasion Tour on many occasions such as TedxLansing, Upper Peninsula Young Professionals Conference, and a professional lecture series at Michigan State University.

Yooper Steez

Upon completing the Hometown Invasion Tour, Sailor sought to better connect Michigan's Upper Peninsula as a community and increase general knowledge of the region.

In 2008, Sailor created Yooper Steez, an online store and blog that celebrates the Yooper lifestyle and community. Inspired by a T-shirt collection that resulted from the Hometown Invasion Tour, the UP silhouette shirt is the primary shirt design. Followers submit images of their adventures while wearing the Steez and write ups about crossing paths with fellow Yoopers in the shirts.

Sailor writes about events, locations, and people local to the Upper Peninsula for Yooper Steez as well as conducting online giveaways like Steez Drops and contests like Bracket of Steez. Since 2008, the company has grown to include many other components, like Plaidurday and 906 Day.

Developer

Aside from developing Yooper Steez and its many descendent project, Sailor works as the Director of Digital at Elegant Seagulls. He began developing websites as a teenager and manages all his own web projects. Shortly after beginning Yooper Steez, Sailor returned to Lansing, Michigan where he worked in agencies like Traction, until relocating to Marquette, Michigan in 2014 when he began at Elegant Seagulls.

Stormy Kromer

In August 2015, Sailor became a brand ambassador for Stormy Kromer; they created a completely custom Kromer flannel cape for Plaidurday 2014.

Plaidurday

On October 7, 2011, Sailor facilitated the first ever Plaidurday—a Worldwide celebration of plaid. Plaidurday takes place every year on the first Friday of October. Celebrate by wearing your plaid and posting a group photo. Since the first Plaidurday, events have grown all over the midwest.

On Plaidurday 2014, over 200 citizens of Marquette, Michigan spelled "MQT" in Ellwood Mattson Lower Harbor Park. The Mayor of Gladstone, Michigan renamed the town to Plaidstone for the day in celebration.

On Plaidurday 2015, following a challenge from Sailor himself, AIGA Minnesota Design Camp succeeded in beating their previous record for attendees in plaid and invited Sailor to speak at the conference.

906 Day

Sailor formalized September 6 as the holiday for 906 Day, a celebration of the Upper Peninsula's area code. 906 is the only area code in America that is so unique in its borders and has a demonym specific to that area code: Yoopers.

September 6, 2012, Yooper Steez offered a discount for $9.06 off every order placed that day, including a 906 sticker with each shirt purchased. It has expanded since to become a local business day.

Beer with Branson

Beer With Branson was launched in January 2010 as Sailor's New Year's resolution. It began as a social experiment inspired by Six Degrees of Kevin Bacon, with the hypothesis that people are connected to each other by much fewer than six degrees. Sailor built a website and marketing campaign to reach out to Richard Branson taking the hypothetical question "If I could have a beer with anyone, who would it be?" to a new level with the Branson spirit of "Screw it, let's do it."

On May 27, 2014 Sailor completed his resolution. His website was shared on social media, and eventually the website was shared by creative marketer Rob Bliss. WZZM 13's Steve Zaagman then saw it and contacted Lorna Schultz of the Economic Club of Grand Rapids, which had invited Branson to Grand Rapids, Michigan. The group then contacted Richard Branson's staff.

Branson was in Michigan raising money for Virgin Unite, the not-for-profit foundation, at an event with the Economic Club of Grand Rapids when Sailor poured a beer for Branson. He asked "So if you could have a beer with anyone who would it be?" To which Branson responded "Well, young entrepreneurs like yourself."

April Fools

On April 1, 2013 Sailor wrote a blog post about a shark that was photographed in Lake Superior. The April Fools joke spread rapidly through social media and the Lake Superior Sharks have become a featured design in the Yooper Steez shop.

On April 1, 2014, Sailor debuted Yoopersingles.com, the "world's first Yooper exclusive dating Website". The dating website promised its dedication to helping Yoopers of all ages, interests and locations find the right partner in life. Social media and regional news took the bait and spread this April Fools prank across the region causing nearly 1,000 users to register that day.

On April 1, 2015, an online petition started by Sailor went regionally viral aiming to change the name of Lake Michigan to Lake Wisconsin. Featured in the local news as well as the Detroit Free Press, the petition instigated quite a debate between the two states and gathered 600 signatures that day.

On April 1, 2016, the creation and construction of the Embassy of the Upper Peninsula was announced with plans to break ground in Lansing, MI. The Embassy was to act as a refuge to Upper Peninsula legislatures, create Upper Peninsula programming, and be a shining symbol to the people, culture, and history of the Upper Peninsula.

Personal life

Sailor lives and operates all of his business in Marquette, Michigan. His parents, Nancy and Byron Sailor still reside in Baraga, Michigan while his brother lives with his family in Madison, Wisconsin.

He spends a large amount of time in training as a professional stone skipper and educator. In 2014, he won the amateur division in the Mackinac Island stone-skipping tournament with 22 skips becoming a professional in 2015. Once the lake is frozen over Sailor can be found playing pick-up hockey.