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This Instagram Photographer Snaps Gorgeous Photos of Cozy Ca…

Kyle Finn Dempsey’s feed is a love letter to the northeast, brimming with homey log cabins, aerial shots of changing leaves and classic vehicles driving along snow-lined roads.


8 min read


In this series, Instagram Icon, Entrepreneur speaks with the individuals behind popular Instagram accounts to find out the secrets of their success.

On a weekday afternoon in May 2016, Kyle Finn Dempsey hopped into his black Land Rover, turned on acoustic radio and readied himself for a typical day exploring and photographing western Massachusetts.

Dempsey ended up at a camp not far from his home, where he discovered an abandoned A-frame cabin that sparked his imagination. Upon closer inspection, he saw that wood rot plagued most of the interior, but one second-story section — a small, cozy corner — had remained pristine. Dempsey knew he could transform the corner into its own magical world, and he dreamed up a scene full of string lights, vinyl records, comfortable blankets and more. He immediately headed home to pick up the items that would make the world in his mind a reality.

Dempsey returned soon after with a guitar under his arm, a coffee pot, flannel shirts and a host of other items that could present the forgotten corner as an intimate escape. The entire scene took him over an hour to set up, but he was determined to get every detail of his mental image right — even if the payoff was just one snap of a camera shutter.

At the time, Dempsey’s Instagram account, @KyleFinnDempsey, had more than 10,000 followers thanks to travel snapshots and other photography projects, but after the A-frame snapshot posted, it blew up. A few months later, he quit his job at a pasta sauce company to focus on Instagram full-time. Today, he has more than 442,000 followers and is known for whimsical shots featuring rustic cabins, cozy nooks, old vehicles, fall foliage and campfires.

Dempsey spoke with Entrepreneur about his inspiration, monetization strategy and advice for budding Instagrammers. 

This interview has been edited for length and clarity.

What’s your chief inspiration?

I have a lot of concepts in my head — visions of ideal scenes and things like that. I grew up along the river in western Massachusetts, and my whole childhood I would build forts, fires and these little camps. I’d build my own little world. I wanted to replicate that feeling — that adventurous, kind of Huck Finn-esque feeling — in images that reflected my actual life, whether it be fishing on the side of a river, canoeing, building campfires or just staying in magical places. Through my feed, I wanted to curate an escape for people. Once I realized I could really hone in on this idea, it was like a portal to a different world.

How do you find places to transform?

After I posted that first A-frame photo, I went out every day that summer, picked a scene from my mind and tried to replicate it as best I could. It didn’t take off every time I posted one — it was a long process of trying a bunch of different things — but I saw what stuck and pushed those ideas forward. I started near where I lived with a few abandoned places I’d found, and when I learned that some of my friends’ parents had some cabins nearby, I stayed there. Then I went on a few trips that fall and stayed in unique, cool Airbnb listings — treehouses, log cabins, A-frames and more. Since then, I’ve stayed at hundreds of places, and through that, I’ve built my dream home in my head, taking little bits and pieces of each place I’ve stayed. I don’t have any partnerships with Airbnb or anything like that, so I just search for places like anyone else would. For example, I’m leaving for Vermont on Wednesday for a Vermont Tourism shoot, and I found a cool Airbnb in the area. You can even just Google “log cabin in New England” and find lists.

To what extent do you monetize the account?

Things are changing, but I usually go by $1,000 per hundred thousand followers. On Instagram itself, I do about one ad a month, and now I charge $5,000 for a spot on my feed — that would be a full-scale one-minute Instagram video and a story post, essentially a mini-campaign. You just don’t want to over-promote on your feed — you don’t want your followers to get sick of it, and you also want to be strategic with who you choose to work with because people can see right through something if you’re just doing it for money. I want to actually use and stand behind all the products I’m promoting, which also helps me create better ads.

How busy does this keep you?

In a typical month, I’m definitely on the move very often — if I get a week in my house, I’m lucky. But I don’t travel very far. I spend most of my time in the northeast. Every week, I’m usually gone a few days at a time doing something for a client. For example, I’ve had a partnership with one client for six months — a blanket brand — and I provide them with a photo package and one sponsored post on my feed per month, so I’d do two one- or two-day themed photoshoots with them per month. I’ve also worked with Land Rover, Samsung, Adobe, Cape Cod potato chips, General Mills, Nature Valley, Highland Park whisky, Samuel Adams beer and others.

What made you decide to start prioritizing video on Instagram rather than only still photography?

I went to school for advertising, and I see a lot of ads that aren’t done well strategically. That’s why what I’m trying to do moving forward is to stick to video — it’s the best way to tell a story, express something and naturally incorporate a product. I’ve done one-minute Instagram videos for probably my five most recent ads, and people have responded much more to that. You can charge more for that because it’s a lot more work and a lot more valuable. In the past, it would cost so much money to get a one-minute commercial in front of 500,000 people. Influencer marketing is really changing the whole scope of modern advertising.

What advice would you give others who want to build a brand on the platform?

You’ve got to find your niche. You’ve got to be everything to someone, not something for everyone, and you’ve got to stick with it and consistently produce. I would say consistency is the biggest thing, and that goes for almost anything you try in life: Keep going, and you’re not going to fail if you’re that determined. Once you prove you’re the top in a category, that’s when people notice. Also, you want to be as relatable as possible — be transparent, be true and communicate with your followers. Build a community and an outlet for people. Be someone they can go to — if you’re there just for the followers, people can feel that, and they’ll notice.

See below for five of Dempsey’s favorite posts.

“Here’s a recent stay at a treehouse in Maine.”

“This is a dual-level perspective of a small cabin with a clear roof in Maine.”

“This is a first-person view of driving my 1964 Ford through the back roads during the fall.”

“Here’s the original A-frame I set up that exploded on Instagram.”

“Here’s an example of a recent video ad.”


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