Leo J – An old fashioned troubadour in a modern world

Once in a blue moon I get the pleasure of coming across a comet. A person who is in my life for just a flicker, but leaves a lasting memory–not unlike the lingering light from the comet’s tail. I must laugh for a moment at my reference to a “blue moon” since last week, we were actually graced with this magnificent phenomena, but I digress. This special person I had the pleasure of meeting recently, was the musician Leo J, otherwise known by his given name, Joel Shupack (Leo J is Joel spelled backwards). Now, most of you who read my blog, know I’m a lover of music. Music and cycling just seem to go hand in hand. Leo J, however, has taken this to the next level. He is currently touring across the country by bicycle, taking over a year to do so, playing at various venues. He is completely self supported and by the looks of his panniers and trailer, is carrying about 100 pounds of gear.

Almost three months ago, Leo J set off from his home in Portland, Oregon and has been pedaling ever since. His drive is not music alone, he is also working on a project called Common Place, interviewing people along his way to make a collective journal, if you will, of our nation and what binds us together. This project was made possible through Kickstarter, and will be able to continue by you, dear reader, attending his concerts and throwing a few bucks his way to help cover his necessities as well as a few ice cream sandwiches–something every cyclist needs.

I was lucky enough to be invited to his concert, here in Madison, by Tom Klein, Dane County director of the Wisconsin Bicycle Federation. Since Tom’s background is music promotion, he continues to put concerts on for Redamte (where I saw Leo J) and for the Majestic. Tom’s passion is putting together bike friendly music events and Leo J most certainly fit the bill.

Leo J came into Redamte quietly. He sat at a table while the Well Fed Sparrows finished their set, and then took stage with his guitar. I had listened to some of his music online prior to the show and was looking forward to hearing his stories set to music. With new artists, you never know how they will sound live. I, along with the rest of the crowd, was very impressed. His voice is beautiful, his songs are thoughtful and full of life and his guitar skills are quite fabulous. He’s witty (listen to his Woody Allen impersonation on the Kickstarter link), and his music style ranges from folk to doo wop. He even throws a bit of jazz into the mix as well just to keep you on your toes (take a listen to his song “Deliver Me”–my favorite of the evening).

After the show, we chatted briefly and I offered to ride with him part way to his next stop,  Milwaukee. I’m never one to be shy, and am always open to finding out more about people following their passion. Talking to people like this tends to keep me honest and inspires me to become a better person. It is these encounters that can also sometimes spark my own passion for life to its fullest if it’s dwindling. Nine times out of ten, when I purposely open one of these doors, magical things happen–so turning my back on them is just something I wouldn’t consider.

“When we were able to relax and ride two abreast, the conversation flowed like we were old friends.”

While on the road, Leo J usually stays with the gracious hosts of Warm Showers or camps out. I met him bright and early, at the place he was staying, on the North side of Madison. After he packed up–I’m sure he was amused when my eyes bulged out from the amount of gear he was carrying–we spun our way through rush hour traffic and finally found our way to the Glacial Drumlin trail–the trail that would take him almost all the way to Milwaukee. Until this time, we weren’t able to talk much due to noise pollution as well as having to dodge cars, trucks and debris in the road. When we were able to relax and ride two abreast, the conversation flowed like we were old friends.

As I stated at the beginning of this post, it is rare to meet someone you have an instant connection with. Although I barely know Joel, and probably won’t see him again for some time, I feel confident we could pick up right where we left off–discussing bikes, music (like me, he is also a fan of Leonard Cohen), books, small towns we’ve enjoyed in the driftless zone, tall bikes (he rode one for the first time in Minneapolis) and the Middle East.

In the short ride we had together, I was able to find out quite a bit about this talented musician. Joel grew up near San Diego but called Bend, Oregon his home through high school. Not long after high school, he moved to Queens, New York–where he first got into cycling and where his dreams of touring were born. In Queens, he played in a punk band, the So So Glos, for awhile and got his feet wet by working at a bike shop. Most recently, he called Portland, Oregon home. Joel’s abilities, other than music, run wide. He’s done some farming, cooking, and has lived in Israel. His family is deeply important to him, and although he seems like a free bird at the moment, he has dreams of “going home” and possibly starting a bike lodge someplace on the coast of Oregon. By talking with him, I could tell he’s having a blast exploring our country and sharing his music, however, I could also tell he looks forward to a time when he can settle in somewhere and have a family of his own.

“We parted ways near Lake Mills, a place he was able to find breakfast–something he looks forward to while bike touring.”

We parted ways near Lake Mills, a place he was able to find breakfast–something he looks forward to while bike touring. Out on the hot dusty trail our goodbye was short. Engulfed by about twenty leaping frogs, I turned my bike due West, and just to prove all meetings have their purpose, on my way back I encountered salamanders on the trail–a creature I cherished as a child and still do. Thank you Joel for holding this door open. Until our paths cross again, may the wind be at your back and may there always be a “little free library”, stocked with Tom Robbins’ novels, at your disposal.

I shot Leo J a few fun questions to which he’ll reply when he gets a moment to rest and catch up. I will post them soon. In the meantime, check out his tour schedule. If you live close to a place he’s playing, I urge you to see him live. You won’t regret it!

Kiersten Kloeckner is an avid cyclist, Bike Fed board member, and author of cycling blog, Two Wheels from Home.

About Kierstin Kloeckner, Bike Fed Board Member

Kierstin is a personal trainer who lives and bikes in Madison and a board member for the Bike Fed. She writes guest posts for us here, but you can read more of her thoughts on how cycling fits into her life at her personal blog Two Wheels From Home

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