Motorcycling first entered my mind as a child when I became aware that my grandfather had 9 fingers instead of 10

I met Amanda Gentry during the summer of 1999. I didn’t see her as a biker back then, just a really talented designer. A few years later, she rode over to the office on a yellow Triumph Tiger with black stripes, seemingly too big for anyone to ride. Since those early days, Amanda has kept herself busy teaching Motorcycle Safety classes, starting several product companies including Buddhabag, manufacturing meditation sacks for enlightened pets (you have to see it to understand it) and in 2006, co-designed Mr. Obama’s 2008 Presidential Campaign logo with fellow designer, Andy Keene and strategist, Sol Sender. I met Amanda recently at her garage in her Pilsen neighborhood and took a ride up Lakeshore Drive on a beautiful afternoon ending at the Coffee Bar on Chicago Avenue for coffee and a great conversation about biking.

WHEN DID MOTORCYCLING FIRST ENTER YOUR MIND?

Gentry: Motorcycling first entered my mind as a child when I became aware that my grandfather had nine fingers instead of ten. This was a result of him learning how to ride a motorcycle but not fully having learned. He went out to the main strip of his town, where upon seeing his mom and sister, decided to gun it and went out of control. He went flying through the plate glass window of a service station and his middle finger on his left hand was severed. At the time, they weren’t able to sew it back on. He was on a Harley when this happened in the 30s or 40s when he was just 18.  From that day on, my grandfather was a nine-fingered man. When I was in kindergarten, I brought my grandfather as the Show and Tell object. I took him up to the front of the class and told everyone, “This is my grandfather and he’s got nine fingers,” and left him there to explain how he ended up with nine fingers.  So motorcycles were essentially taboo in our home as it was equated to losing digits.

WHAT WAS YOUR FIRST DAY ON A BIKE LIKE? 

Gentry: I went on the back of a friend’s motorcycle when I was 27 years-old. The only way I could respond to this new experience was pure laughter. I was on the back of the bike laughing uncontrollably, holding on for dear life. It felt like I was flying through the city. “Oh my god, I’m a superhero.” He dropped me off that night and I immediately started researching motorcycles. Within two months of riding on the back of his 1981 Honda cb750 Supersport, I got my first motorcycle, a 1977 Honda cb550 and named it Harry. It wasn’t even running at the time. I bought it at the border of Wisconsin and Illinois and had it delivered to Bob’s BMW where they got it running. In the meantime, I took a motorcycle riding class. And that was that!

My first day on the bike… was terrifying. It was a two-day Motorcycle Safety Foundation course and on my first day, I felt like a complete idiot. I felt like I didn’t know my left from my right, I didn’t know what my hand should be doing. The motorcycle instructor could tell I was frustrated and told me, “Don’t worry. Tomorrow, when you come to class, it’s going to feel like old hat, because it’s all about muscle memory.” And, that’s exactly what happened. I came the second day and it was like my body had figured it out overnight while I was sleeping.

WHAT DO YOU RIDE?

Gentry: As much as I love my Honda cb550 (and now it’s in full running condition) it would leave me stranded on street corners. I would get to know strangers ­– people I’d never met before or I would just walk up to someone on a street corner and ask them to help me push start my motorcycle for me. It really left me frustrated and I would have to get it towed sometimes. I bought a second bike because a vintage bike in my opinion is not the best first motorcycle to have.

This happened as I started talking about a cross-country motorcycle trip with a friend of mine, who actually was my original motorcycle instructor, who incidentally wound up hiring me the next summer to help teach riding classes for a couple seasons. In planning the month long trip, we knew the Honda would not make it. So I ended up finding a used ’99 Triumph Tiger, whom I named Tony. He was yellow with back stripes, a very big bike for me. It was 900 ccs. The seat was taller than my inseam, so I was not flat footed on the bike. Everyone and anyone told me that the bike was too big for me, that I should be able to stand flat footed on the bike and so on. I said “Bullshit. I like this bike!” I wound up getting the Tiger and I loved it. It was a dual purpose bike and not only was it perfect for the road trip since it had heated grips and we were starting in November, it also had a huge tank so I could go far distances. I actually felt really safe on this bike because of the height. It was so tall, when I was riding in the city, I was eye-to-eye with city bus drivers! I was able to look over traffic and people were more aware of me on this taller motorcycle. I loved this bike. I was fearless on this bike. I rode this motorcycle for two great seasons and I don’t know what happened, but on the third season, after winter, I came out and looked at the bike in the garage and I went, “My god, that’s a big bike!” As I sat on the bike I felt nervous. And all of a sudden, I was riding tentatively where as before, I was throwing the bike around like a rag doll. That’s when I realized that it was not wise for me to continue riding this bike – especially with the trepidation I was feeling. So I started thinking about another bike that would be better for me in the city that was still flickable like the Tiger.

Flipping through magazines, I ran across a photo of a concept bike, which is now the Yamaha MT03. I saw that bike and fell in love with it. I think a year later, my friend Sarah, who I had taken the motorcycle trip to California, said to me, “Hey Amanda, that MT03 is in production. It’s not in the States but it’s in production.” That was all I needed to hear. I’m not really good at taking “No” for an answer when I really want something, so I reached out to multiple dealerships in England. I thought it would be good to stick with a country that spoke the same language as I did. There were a lot of dealers who didn’t want to deal with the trouble of shipping a bike to the U.S., but I found someone in Wigan, England who was willing to sell it and ship it to me. I ordered that bike in the beginning of June of ’06. It got to Chicago on the third week October and the day after that bike hit our shores, it snowed! So I had my dream bike sitting in my garage all winter waiting for the next riding season to arrive. I’ve been enjoying that bike since. It’s nimble and a great City bike. And since it’s not in production in the U.S., it catches a lot of eyes, especially motorcyclists. Whenever I park it, people come up to me and ask questions about the bike and they’re always surprised that it’s a Yamaha.

TELL ME ABOUT YOUR CROSS-COUNTRY ADVENTURE.

Gentry: That ride was a lot of fun. We left Chicago at the end of October. Our plan was to ride for one month and return by Thanksgiving. It was a cold time to ride. We just rode due West. Right before we reached San Francisco, we experienced a little drama. We were just outside Bakersfield and it was really hot. The two of us were both wearing chaps and padded jackets, which made it even hotter. My friend, Sarah was riding the BMW 650 Dakar. Because I was riding the bigger Triumph Tiger, a three-cylinder 900cc motorcycle, there were moments when I would pull ahead and Sarah would drop off and turn into a small dot on my rear view mirror. I would then slow down so that she could catch up again. As we were riding through the middle of the desert, at one point, I looked back and realized that Sarah was completely missing from my rear view mirror. I slowed down and still, no Sarah. I decided to ride to the next exit and ride back on the opposite side to find her. As I head back I see her on the side of the road. She had a flat on her front tire, which is extremely dangerous at high speeds. Had she not been experienced as she was, it could have been a tragic accident. So I had to keep riding to the next exit and turn around to reach her on the other side of the road. Once I reached her, we decided that I should ride to the next exit again and find a couple of cans of Fix-a-Flat and then we could ride to a mechanic to fix the tire. Once we fill the tire, she starts riding and the tire just starts oozing out all of the Fix-a-Flat we had just injected into her tire. It was not a puncture but a gash. And now there was a slug trail behind her motorcycle and we’re stuck in the desert. And it was hot.

After assessing our situation, we concluded that we were two relatively good looking women, wearing chaps, and we would wave someone down to help us (laughter). That’s what we were going to do. We were going to somehow, summon someone with a flatbed trailer and they would automatically put Sarah’s bike on the flatbed and take us to the next service station. We were out there about three hours and lo and behold Sarah sees coming down the road a man driving a white F350 with a flatbed trailer – with nothing on it! What happens next, I wish I had a video of. Sarah stands straight up, facing the driver, totally locks eyes with the him and points at him and then points to the side of the road where her bike is and directs him, like “YOU–Over here!” And he’s like “Ok,” and pulls over and gets out. He’s name is Greg and seems like a really nice guy. And…he’s a motorcyclist! He’s a Motorcyclist! I know I don’t have to say this to you Sam, or anyone out there in the motorcycle world. I actually get choked up when I talk about this. When you become a motorcyclist, you become part of a large family. And, this man saw that we were in trouble and knew exactly what to do. He wheeled up Sarah’s BMW onto his flatbed and tied it down with tie downs. We were probably 200 miles outside of San Francisco, which was our final destination. He was headed to Oakland and he said, “Why don’t I just take you all the way to San Francisco.” And so, we took him up on that. Sarah rode with him in the cab and I followed on my Tiger. And he took us all the way to San Francisco, dropped us at the parking lot of the BMW dealer. It was amazing. It could not have worked out better.

WHAT DOES IT MEAN TO BE A WOMEN IN THE WORLD OF MOTORCYCLES?

Gentry: There’s a part of me that feels a little romanticism about the whole thing because it’s a man’s world and women ride “Bitch” and for me, it feels great to “Man” my own ship.

It also feels really American to me. I don’t know where I get that nostalgia because it’s not like we have that in our history of women riding motorcycles but the song, “American Girl” by Tom Petty is one that runs through my head whenever I ride. That song and the Beastie Boys, “You Gotta Fight for Your Right to Party,” and the “Little Drummer Boy.” I don’t know why (laughing). I think it’s probably the beat of the song because that’s the beat that my engine makes when I'm riding.

WHAT GOES THROUGH YOUR MIND WHEN YOU'RE RIDING?

Gentry: I just think about songs. "Little Drummer Boy."

WHAT IS THE COOLEST THING YOU'VE DONE ON A MOTORCYCLE?

Gentry: When I was riding Tony the Tiger on long trips, I would do this move called the “Superman” to stretch my legs. I would lean forward and take my feet off the foot rests and stretch them back like I was Superman. If there was an open stretch, that’s what I would do to stretch my legs. Just like Superman.

WHAT IS YOUR FAVORITE GEAR?
Gentry: My Chicago Flag helmet. Technically, they say we should replace our helmets every few years, but dammit, it’s cool!

WHY DO WE RIDE?

Gentry: Superhero. It makes me feel super-human.

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Amanda Gentry is a graphic designer living in the Pilsen neighborhood in Chicago. For the past 15 years, she has worked as a design consultant for companies such as Comcast, Converse, GE, Goldman Sachs, Harley-Davidson, IBM, Motorola, Toyota and Western Union. More recently, Amanda worked exclusively with the Chicago 2016 bid committee in their efforts to host the 2016 Summer Olympic Games. Amanda graduated, cum laude, from Boston University in 1995, where she received her B.F.A. in Graphic Design. Her design work has been featured in H.O.W. Magazine and Print Magazine and has won several Type Director’s Club and AR 100 awards.