A couple of weeks ago I was on a particularly beatiful ride around the Oakland/Berkeley hills when, reaching the top of a climb, I noticed someone taking pictures of a friend as he was reaching the summit. Then I had a flashback to events like the Death Ride and similar events where they contract a photographer to take snaps of all participants, with the option to sell some prints shortly after. So I had a small side-business idea for amateur or freelance photographers, now that so many weddings have been postponed or scaled down, and I bet many are hurting.

Cyclists riding a mountain by the sea

Okay, tell me already!⌗

The setup is simple. You find a nice spot with lots of cyclists (if you’re not sure where this could be, ask anyone wearing spandex on a Saturday morning). Scope the area for good angles, preferably looking down as cyclists climb up so you have more time to snap a good one. Then get a comfortable chair, turn on some music, and click away. At the end of the day, put samples of those photographs on Twitter or Instagram, and sell physical prints to anyone asking, hopefully the subject of each snap. Easy!

Now, there are some logistical problems to solve. Let’s go one by one.

What if people don’t want their photograph taken⌗

Some people are not comfortable with their picture taken by a random stranger (that would be you). Luckly, as long as you don’t enter private property you are on solid legal ground regarding your ability to photograph anything and anyone in a public setting, at least here in California. Do you reading, because I am not your lawyer. That said, it’s probably not good business, and perhaps even dangerous, to take pictures of people who don’t want them taken. In order to solve that problem, you could place a number of cardboard signs leading up to your spot, where you briefly explain what you’re doing, and asking riders to yell “no pictures!” if they want to remain anonymous.

Another benefit of these signs is that it lets people think about how they want to look in the picture, maybe pose or smile if the climb is not too streneous, and increase the chances that they’ll like your pictures.

Letting people know how to find you⌗

It’s the end of the day. Assuming you chose your spot well, you have taken a few hundred pictures, some of them might even good. But the world doesn’t know about them. What I suggest is that you use the signs you made to let people know how to stop you from taking pictures to also announce your Twitter/Instagram feed. It should be something short and memorable, because let’s be honest, when you’re grasping for air on top of your bike, you don’t have the mental fortitude to commit @RandomPh0tographer90210 to memory.

Or you could go old school and put a small stack of business cards at the top of the hill, shortly after your spot. That’s also a good way to gage how many people are at least marginally interested on your photographs.

Actually selling prints⌗

If you are a freelance photographer, you probably have your own setup for how to sell your pictures. If you’re a complete amateur and just wnat to make some side money while spending a nice morning outdoor, you can use a combination of PayPal for payments, Kinko’s for printing and just mailing the prints by hand.

So that’s it! If you try this, please let me know. Maybe I’ll ride by you.