There’s a difference between taking pretty pictures and capturing someone’s essence.

That’s what this week’s Business Origin Stories guest, Jenny Losee, does. She’s a luxury wedding and brand photographer with the eye of an artist, the soul of a storyteller, and a confidence that’s shaped a beautifully intentional business.

I’ve admired Jenny’s work for years. She’s shot everything from dreamy weddings across continents to brand shoots that stop you mid-scroll. But beyond the Vogue and People Magazine features, the celebrity weddings (hello, Robin Thicke!), and her recent dreamy shoot in Africa, Jenny is an artist in every sense of the word.

We sat down for a conversation about what it actually looks like to go all in on artistry, mindset, and mission. And let me tell you: if you’re in business, you need a photographer like Jenny in your corner.

From Side Hustle to Signature Style

Jenny’s story started like so many of ours do: balancing a 9–5 with her creative work, staying “safe,” and waiting for the perfect moment to leap. But after a second layoff and a dwindling savings account, she realized it was time to bet on herself.

She began saying yes to every opportunity—shooting weddings on weekends, reaching out to planners and vendors she admired, and creating her own styled shoots when client work was slow. Over time, that persistence paid off. She carved out a style that was unmistakably her own: timeless, editorial, and deeply human.

Today, Jenny’s one of the top 30 wedding photographers in the country, known for images that feel as honest as they are beautiful—and a way of working that puts story at the center of everything she does.

Why Brand Photos Matter

We talked about the difference between “just getting some shots” and building imagery that makes your business feel like you.

Jenny’s not the kind of photographer who breezes in for a quick 30-minute shoot. She takes her time, asks thoughtful questions, and pays close attention to how you want to be seen so the light, the styling, and the overall feel of the shoot actually match the voice of your brand.

She’s the first to admit she’s not the photographer for quick headshots in front of a white wall. Her work is timeless, layered, and editorial. Some of it’s shot on digital, some on film (which, by the way, is chef’s kiss), but all of it is designed to make you feel something.

I know this personally as she shot my branding photos, and they’re still the ones I come back to again and again. They haven’t aged or gone out of style, and I still feel like myself in every frame.

If You’re Thinking About Making a Leap…

Whether it’s going full-time in your creative business or stepping into more visibility, Jenny shared this gem:

“Even if you don’t have work, make work – because with work comes work.”

Jenny didn’t wait until she was “ready.” She created when no one was watching, reached out when the stakes felt high, and said yes when fear screamed no. During this conversation, she reminded me that the real magic is in aligned action.

If you’re in the middle of building something that matters, Jenny’s story is your reminder: stay in motion, trust your gut, and don’t be afraid to make your own work when no one’s watching.

🎧 You can listen to our full conversation over on Apple Podcasts or Spotify. I think you’re really going to love it.