8 min 16 sec

Extreme Makeover: Tinder Photo Edition

This fashion photographer was used to seeing bad Tinder photos, but they never stopped shocking her. “Do they know what they’re communicating with this image?” she thought. No, they didn’t.
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What It's About

A photography side hustle worth swiping right on!

Business Model
Skills Required
Photography & Communication
Profit Potential

Words of Wisdom

Here are a couple of Side Hustle School tips for sprucing up your dating profile (listen to today's episode to hear the rest)!

Use good photos even if you don’t hire Charlie. No one else in the photo, don’t hide your face, don’t look overly posed. And say what you’re not into—disqualify potential suitors (this will also help you attract the right ones).

Fun Fact

Charlie's approach was finally confirmed scientifically earlier this year when she had a client that was a huge data geek. He had pictures taken by four different photographers and ran the photos through an algorithm that told him which of the photographers got the best ratings. Charlie’s did—by a significant margin!

Notes from Chris

Episode 728
Photography was Charlie Grosso’s passion and career in her early twenties. A Chinese American woman with an Italian male name, she worked with high-end fashion and luxury brands for years, photographing models and products. She became a master of how photos communicate messages, but the magic of her work started to wear off.

At 30, Charlie went through a divorce and fell upon even more difficult times when work slowed down. But it also didn’t actually seem like the worst thing in the world. Charlie was ready for something new, a challenge, an adventure. She began traveling more, and she started online dating.

She met lots of interesting people and made a few great friends. But something bugged her every single time she logged onto Tinder: most profile pictures were really bad.

The “mirror selfie” was the worst offender. Another common horror was the photo taken by the guy sitting in the passenger’s seat.

“What do you want me to know from this picture?” Charlie likes to say. “That you have a driver’s license? That you own a car? That you work for Uber?”

With a background in fashion photography, Charlie could immediately tell when people were communicating something in their pictures that they didn’t intend—and when the more important messages were being left out.

A friend suggested she help the photographically-challenged take better pictures for Tinder. At first she wasn’t sure—she had never loved doing headshots—but the friend persisted for months, and finally, Charlie gave in.

She bought Tinder Photography, put up a very basic Wordpress site that advertised her services in New York City, and just let the page sit while she continued to work on her other writing and consulting projects.

And then, out of the blue in February of 2015, she got an email.

Someone had found her website and wanted to hire her. Charlie doesn’t know exactly how they found her site, but from the modest traffic she was getting, it seemed people were just finding it on Google when they were searching for “tinder photography.” It was weird, happening so randomly, but she took the gig. Her humble domain startup cost was made back with that one client.

Charlie soon found herself with more clients. She was more open about telling her friends and network about the side gig, and the more she talked, the more clients came, each paying as much as $650 per session.

In May of 2015, Charlie got featured in a TIME article about photographers for Tinder. She was featured in a few other articles for other websites as a result, and things started to really take off. She was starting to have several clients each month—and the random hustle idea was starting to seem like something she was going to stick with. By the end of 2015, Charlie had made over $10,000.

Hopefully, her next steps will enable her to focus more on Hello Future. Whatever happens, Charlie’s still living the dream of infusing her skills with a passion for helping people live better lives.


  • Tinder Photography: Interested in taking your Tinder profile to the next level? Head on over to Charlie's website!
  • Hello Future: Learn more about Charlie's new project over on her website
  • WordPress: Charlie used WordPress to setup Tinder Photography, and here you can learn how to install your own WordPress site in 5 minutes


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"The time I spend walking and talking with clients is just as important as those when I point my camera at them. The goal is to make images look less staged and more like snapshots, and getting a feel for their personality is important to achieving that."
—Charlie Grosso #SideHustleSchool

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Chris Guillebeau