The Five Whys: Jessie Gentry

California native grew up working on cars but turned to bikes after years of strife with an old Mustang

Jessie Gentry is a Los Angeles-based photographer and writer who I had the pleasure of working with at RideApart. One of the founders of The Velvets MC – an all-female motorcycle club – she is very much the sort of person the motorcycling needs more of. You can check her out at and on Instagram: @JessieGentry

When did you start riding?

I started riding about seven years ago, after spending at least five years saving up and planning to buy a motorcycle.

At the time I had a ’66 Mustang as my daily driver and I was doing all the repairs on it myself with my YouTube mechanic’s license. It was just a money pit and whenever I would get close to saving up enough money I would have to fork over a ton for an engine rebuild or a new rear end.

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I knew that I wanted a Honda CB because I could do the work on it myself. So, I spent most of my free time perusing Craigslist and eBay looking for The Bike. The day that I found it, a co-worker called me with a really sweet offer for my Mustang. I sold them the car and they actually drove me down to Long Beach and helped me look at the ’75 CB350 I had found.

The previous owners towed it to my house for me and, after a long battle with a shitty charging system, I was on the road. I knew I needed to ride no matter what and I spent a long time really doing my research. I’m really happy I started with that shitty little CB because it taught me troubleshooting and kept me slow enough that I didn’t hurt myself.

What bikes do you own?

I have a small stable of motorcycles. I still have and will hopefully always keep my ’75 CB360. I also still have the ’72 CB750 I rode for a few years right after the 360, but I plan to let that one go soon to a friend. I have a 2011 Harley-Davidson Sportser 1200 flat track bike and a little 1991 Honda XR80 pit bike that has an adorable Mexican-blanket seat.

RELATED: 2013 Harley-Davidson Sportster 1200 Custom – First Ride

My everyday bike is 2011 Ducati Multistrada 1200S that I splurged on about a year ago. I bought it after totaling an ’84 Honda VFR750 that I had barely gotten to ride (I really loved that bike) before getting in an accident. I broke my shoulder, so I wanted a comfortable riding position that would allow long distances without too much wear and tear on my body. I ended up falling in love with the bike – her name is Diana Prince (aka Wonder Woman).


I’ll admit it is a very heavy ride to manipulate for my small frame and 130 pounds. Everything is peachy keen and couch-like until I hit the canyons, then I have to use all my might to push her around.


What bike do you dream of owning?

I have a few bikes that I dream of owning but the first one I might buy myself would be the Yamaha XSR900 or even XSR700. I have gotten the chance to borrow both as press bikes; for a bike to ride around the city on, they’re just so much fun. The engine character and riding position of the 900 really make it easy for me to whip around. And despite what I’ve heard some other people say, I think the bike looks pretty dang cool.

2018 Yamaha XSR900

If I am operating in a realistic budget realm, I would say I want a 1990s Honda CBR next. I plan to café it (Man, I really want to see that –CC). I have a few girlfriends who have caféd these bikes and they are really a cool look and a fun ride.

What’s the best motorcycling adventure you’ve had so far?

I would say every day of riding motorcycles is my favorite adventure. Motorcycling grounds me, an otherwise scramble-brained, working-on-10-things-at-once person. When I am riding, especially in my hairy Los Angeles commute, my mind is calmer than at any other time in my life. I am purely focused on the traffic and anticipating the movements of the vehicles around and in front of me. I am never more Zen than when splitting lanes on a motorcycle through LA traffic… until someone does something really stupid and I snap out of it to curse inside my helmet.

Where do you dream of riding?

I would love to go see other parts of the world. Honestly, I haven’t seen anything; I’ve basically stayed in California my entire life.


I want to rent a bike and ride around Hawaii, just because that’s my favorite place to go that I’ve been so far. I want to go tour in Bali, Vietnam, Indonesia. I would probably cry some ancestral tears if I ever got to even SEE the Isle of Man let alone ride it.

Despite its flaws, there is something really cool about social-media in that I know so many motorcycle friends all around the world. I could probably plan a trip around finding friends who have an extra bike in their garage.

(All images belong to Jessie, obviously – save the stock photo of a Yamaha XSR900)