8 min 19 sec

Lifelong Freelancer Adds Real Estate Photography to Portfolio

When a lifelong freelancer becomes interested in real estate photography after selling his home, he learns the trade and develops a new hustle in a flash.
Photography Real Estate Service

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What It's About

A lifelong freelancer snaps at the opportunity to start real estate media company.

Business Model
Skills Required
Photography & Marketing
Profit Potential

Words of Wisdom

Randy shares some advice regarding finding a hustle idea: “Assess your strengths and talents. Find something that you would love to do. Then hold on to it like a dog with a bone.”

Fun Fact

Last year over 5 million homes were sold in the USA alone. With that many properties changing hands, there are plenty of opportunities to offer services or products to those both buying and selling property.

Notes from Chris

Episode 1310

Randy Hill isn’t your typical side hustler. At sixty-four-years old you’d be forgiven for thinking he was retiring instead of starting a business on the side. But, Randy has spent his whole life doing things the unconventional way, especially when it comes to work.

Last year, he added another notch in his side hustle belt. He and his wife were selling their home, and the realtor sent out a photographer to take pictures. Having professional photos taken is a great way to improve a listing and garner maximum attention.

It was good timing in more ways than one. Randy had been taking photographs for decades as a hobby, and now he followed the photographer around his house, absorbing the process. After the photographer left, Randy started to think, I could do this. Naturally, he decided to try.

The first thing he needed was a proper camera. In a flash, he purchased a second-hand Nikon for five hundred dollars and an accompanying zoom lens for three hundred dollars. He had a friend who was getting rid of a tripod, so he got that for free. At the very least, if his idea for becoming a real estate photographer didn’t fully develop, he’d have a new camera setup to re-ignite his love for photography.

The next step was to get some training. Randy didn’t want to spend too much money, or any if he could help it, so he came up with a clever strategy. He contacted a realtor friend from his local area. Randy asked if he could accompany the realtor and their photographer for a day to watch them work in even more detail.

Randy then moved on to the second step in his education. He turned to the tried and true place to learn anything… Graduate school? No! YouTube, of course.

But online learning can only take you so far. It was time to start putting some of the lessons into practice. To do that, Randy needed to snap up a client!

He tried postcard drops at businesses, calling realtors directly as well as messaging them on Instagram. He found Instagram to be the most effective method. He’d follow realtors accounts, then direct message the ones that followed him back—which many accounts do automatically. He’d invite them to look through his profile—which now had several examples of his work—and, if they liked what they saw, he’d propose working together. As an extra incentive, he’d offer a free or heavily discounted shoot on the first property.

This technique worked really well and within just a few short months Randy was making up to five hundred dollars per month from his side hustle. A good result for a photographer with only free, informal training.

While coronavirus has slowed things down a bit, property is still selling and Randy is still working hard to introduce himself to new realtors and build up his network of clients. As you might expect from a sixty-something side hustler, he’s been around the block a few times, seen a few worldwide catastrophes and believes this will all be over at some point. He wants to be ready for when it is.



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
"Assess your strengths and talents. Find something that you would love to do. Then hold on to it like a dog with a bone."
—Randy Hill #SideHustleSchool

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Chris Guillebeau