Extreme Makeover: Tinder Photo Edition

This transcript was generated from the episode audio and may contain minor errors.

[Music]

What's up my friends, Side Hustle School community listeners, awesome people out there. My name is Chris Guillebeau. As we approach the end of season two, let's talk today about extreme makeover, Tinder photo edition. So it turns out that a lot of dating profiles suck. There's no better way to say it.

They're just really bad. And the photographer I'm gonna tell you about today 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. Apparently they did not. So she sets out to help them, earning up to $650 per photo shoot.

Along the way, she gets featured in Time Magazine and has her process validated by an algorithm, which is a whole crazy side note of its own. I'm gonna tell you about it in this story. And as a special bonus, at the end of the episode, I'll give you the Side Hustle School top tips for dating profiles. That's right, leveling up at the end of the year, here's a shout out to our sponsor, stay tuned. [Music]

Photography was Charlie Grosso's passion and career in her early 20s.

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 age 30, Charlie went through a divorce, fell upon some other hard times when her work slowed down, but it also didn't seem like the worst thing in the world. She was ready for something new, a challenge, an adventure. She began traveling the world more and she started online dating.

She met lots of interesting people, made a few good friends, but something bugged her every single time she logged onto Tinder. Most profile photos were really, really bad. The mirror selfie was the worst offender. Another common horror was the photo taken by the guy sitting in the passenger 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.

None of these messages are persuasive. With a background in fashion photography, Charlie could immediately tell when people were communicating something in their pictures that they didn't intend, and also 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 tinderphotography.com, 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 projects. Then one day out of the blue, she got an email. Someone had found her website and wanted to hire her. It seemed that people were just finding her site on Google when searching for tinder photography. It was weird happening so randomly, but she took the gig.

Her humble startup costs were made back with that one client. And she soon found herself with more. 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. She adapted her previous model photography strategy to tinder photography. She doesn't hop into taking pictures as soon as she meets her client.

She talks with them, walks them around parts of the city, and gets to know them. This introductory hour really helps her clients find some ease, which is essential for great images, because she doesn't want to just provide stuffy headshots. In May of 2015, Charlie was featured in a Time magazine article. At this point, things started to take off. She was beginning 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 that year, she had made over $10,000 from it. She also discovered something after a few dozen photo shoots that she did not expect. 90% of her clients are men. She found that despite the fact that when it comes to online dating, men tend to be a bit more forward, or sometimes even aggressive and overly interested. A lot of those men also tended to express a deeper sense of insecurity.

They hated the idea of being judged by a picture. They were uncomfortable having their picture taken in the first place, and they didn't want their friends to find out they had hired her. Some of them said they had even been made fun of for taking their Tinder profile so seriously. All of that only reinforced Charlie's approach. Take the time to get to know them first.

When people feel valued and understood, not rushed or judged, that's when the best pictures are taken. Her approach was confirmed scientifically earlier this year when Charlie had a client who 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. You could call this Tinder hacking. We should do a story on him at some point.

Charlie's photos came out ahead by a significant margin. Lately, she has been making a shift. In 2016, she founded an organization called Hello Future that educates and trains refugees to help them adapt to new homes and countries. She loves the organization and now spends half of her time running it overseas. But as a nonprofit, it's not making money.

She needs the income from Tinder photography, which now has several clients per week when she stateside to keep Hello Future going. Some friends have suggested franchising so the business can still run while she tends to the organization, but she's concerned about quality assurance. So instead, she's thinking of writing a book filled with her insights about online dating, self-confidence, and putting your best foot forward in life even when the struggle is real. Whatever happens, Charlie's still living the dream of infusing her skills with a passion for helping people live better lives. All right, as part of the brand new agricultural school complementary dating service, this is one of the things we're working on for 2019, here are a few top tips for your dating profile.

Now, most important of all, use good photos even if you don't hire Charlie. I mean, if you're in New York City, of course you should hire Charlie. Thank you so much, Charlie, for allowing us to share your story. But however you get them, quality photos are paramount. There shouldn't be anybody else in the photo, by the way.

This is another common mistake. Don't hide your face. Don't wear sunglasses. Don't look overly posed. And when it comes to writing your profile, a few simple things you can do.

First, be specific and be a little bit different. Okay, don't say you like evenings by the fireplace or moonlit walks. I mean, mix it up a little bit. Be creative, as I said. You should also say what you're not into.

Disqualify potential suitors. Don't be generic. Don't be bland. This is actually gonna help you attract the right people. Next, don't overshare.

It's good to be a little bit transparent. It's good to be honest, but no need to present all your negatives up front. And last but not least, ask your friends to help. Ask your friends to look at your profile and objectively give you some feedback. Objectively say, first of all, what they think about what is written and presented there and also what might be missing because they know you best.

They know your attractive qualities and you might be selling yourself short. So get some feedback. I hope those tips are helpful for somebody out there. And I hope everybody else enjoyed the story. All kinds of different ways that you can make money.

This is a new economy, so many opportunities. And I think we're gonna hear about a lot more in 2019. So I look forward to sharing that with you. Tomorrow is the final recap of the year. The show notes for today are at sidehustleschool.com/728.

We'll include links to Charlie's work, anything else I mentioned in the episode, and I'll be back with you tomorrow. Thanks again. This is Chris Guillebeau for Sidussle School. [Music]