Under The Hood: Jennifer From Shoott

Let’s start at the beginning — what was the moment that planted the seed for Shoott?

My lightbulb moment: I was acting in a show and took the train home with the lead actor — an incredibly talented artist who also waited tables. That night, all he wanted was to buy a six-pack to celebrate his girlfriend’s birthday. But he didn’t have enough in his bank account. And I knew he wasn’t irresponsible. He was hustling, but still struggling.

That moment stuck with me. Yes, I loved acting; but part of me also wanted to build something that could be part of the solution for fellow artists.

On a whim, I reconnected with my former boss and mentor, Dan, a serial entrepreneur. He then became my first co-founder and compass in this wild journey to create a unique business model that could help freelance photographers survive the gig economy; it wasn't in my exact wheelhouse, but we decided to give it a try.

Once you had the idea — how quickly did things start to take shape?

A month haha! We did an MVP and had a site up very quickly and launched it to our personal network of friends — and it took off immediately! We were so excited there was this immense demand for easily bookable outdoor mini photo sessions.

Our earliest surprise was that we had assumed (since it was 2018) that influencers and young millennials would be our biggest client base given the rise of Instagram. That or tourists looking for photos while they were traveling. However, we decided to advertise and test hosting sessions in an area filled with young families, and it booked out so quickly that we realized our target demographic is actually families with young kids. It was a major win that helped us scale quickly.

With such strong early traction, how did you think about distribution — and what made DTC the right launchpad?

We started in DTC and since we're a service, that's where we're staying! No retail for us, though we do love partnering with highly compatible downstream retail products like framed prints and photobooks.

Behind the scenes, what’s been one of the biggest factors in Shoott’s growth?

It's our ability to prioritize and make decisions quickly. We maintain a culture that's big on getting things done, so we're light on meetings, we encourage our team to problem-solve and provide suggestions for issues, and when we have new initiatives, we test quickly and go where the progress is.

Fun fact: making 1% of incremental improvements every day for a year results in a 37-fold improvement!

And on the flip side — what’s something about building a DTC business that caught you off guard?

Since it's my first time building a DTC brand, I had to get used to the fact that everything can turn on a dime — first it was COVID, then the big one for us was iOS 14.5 privacy changes leading to our CPA increasing anywhere from 2x to 10x. And now, I'm seeing so many other DTC brands stressed about the possibility of looming tariffs destroying their business.

In terms of lessons I wished I knew earlier: I wish that I had gotten a top-notch accountant earlier in our journey.

Your offer is so unique — what kind of feedback do you typically get from customers?

That we seem like a scam at first because of our offer/hook of a free photo shoot where you only have to pay for the photos you love! Everyone says it sounds like it's "too good to be true," and people are skeptical — which we totally get.

We use the opportunities to educate potential clients via ads, emails, direct client conversations on social media, and content marketing. We also redirect them to external reviews.

You’ve already scaled impressively — what’s next for Shoott?

We're constantly looking for more ways to improve our client and photographer experience. On the client side, we're looking to introduce more post-photoshoot options (paint-by-numbers, AI headshots, etc.). On the photographer side, we're trying to provide more resources to help photographers continue to work on their craft.

And finally — what’s the best advice you’ve ever received?

“Feelings are not facts” — just because something feels like it's true doesn't mean it necessarily is.

Bonus round: what tools power your day-to-day?

Monday, ChatGPT, Read.AI, and it runs behind the scenes but Black Crow AI as well.

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