We were lucky to catch up with Jack DeMaio recently and have shared our conversation below.
Alright, Jack thanks for taking the time to share your stories and insights with us today. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?
I never really planned to make a living from photography. After college, around 2017, I picked up a camera just because it felt exciting. Growing up, I was that quiet kid who spent hours writing songs in his room and dreaming about making a living through music. But as I got older, I realized how brutally hard that path would be. Around that same time, I started falling in love with photography. It started small — I’d drive the backroads of Pennsylvania and Delaware with my camera, just chasing cool landscapes. Angela, who was my girlfriend at the time, and I would take road trips and go hiking in national parks around the country. I’d photograph landscapes, wildlife, and portraits of her and friends.
Photography pulled me out of my shell. Music was something I did alone. But photography got me out in the world — meeting people, exploring, going on adventures, and actually capturing moments I could look back on. It gave me a sense of freedom I hadn’t felt before.
At some point I thought, “What if I could actually do this for real?” My first step into the professional world was working at a local marketing agency doing real estate and commercial photo/video. At first it was exciting, but it didn’t take long to realize how different it felt from the personal, creative work I loved. It was structured, transactional, the same thing every day. I wanted more than that.
That’s when weddings started to make sense to me. Weddings are emotional, meaningful, and full of creative opportunities. Plus, you’re not just a service provider — you’re hired for your vision. That clicked with me. I grew up around entrepreneurs — my dad and brother both ran their own businesses — and I’d always felt drawn to that path. So in 2021, Angela and I officially started J&A Wedding Photography. She’s the “A” in J&A.
We started out on wedding directories like The Knot and WeddingWire, and slowly began to book weddings. I built our first website myself, and that sparked another obsession: marketing. I dove headfirst into Google Ads and learned how to bring couples directly to us. Once I switched our main advertising from directories to Google Ads, things really took off.
Over time, I expanded what we offered. We added video, and by pure luck, I met two Ukrainian videographers who had just come to the U.S. during the war. We became friends, and they introduced me to an entire community of other photographers and videographers. That changed everything. I went from shooting weddings solo to building an actual team — people I trust, people I care about, and people who share the same love for this work.
Today, J&A is photographing and filming around 130 weddings a year. We’ve built something that doesn’t just function like a business — it feels like family. Our couples get a fun, lighthearted, personal experience, and we get to do what we love for a living.
It definitely wasn’t instant. It took years of learning, refining, building systems, and reinvesting every dollar. If I could go back, I’d probably focus on marketing and team-building a lot earlier, because that’s what really changed everything for us. But every step — from those backroad drives with a camera to running a full creative business — shaped the path to where we are now.
Jack, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I’m the owner and founder of J&A Wedding Photography, a photo and video studio built around authentic storytelling. What started as a personal passion for photography slowly grew into a full-time career — and eventually, a team that now captures around 130 weddings a year throughout the Northeast.
What really sets us apart is our documentary approach. We’re not just focused on perfect poses or Pinterest moments — we’re there to tell the real story of the day. We lean into candid moments, natural interactions, and the energy of the people around our couples. One of our favorite ways to do this is through guest confessionals and interviews. These unscripted moments — whether funny, heartfelt, or totally unexpected — add a layer of depth to the story that couples get to keep forever.
Weddings are about more than portraits. They’re about how it felt to be there. My team and I approach each wedding like storytellers, not directors. We let the day unfold naturally and focus on preserving those in-between moments that couples often don’t even realize are happening.
I’m incredibly proud of the team we’ve built — talented photographers and videographers who genuinely love what they do. Our goal isn’t just to deliver a gallery or a film. It’s to create a time capsule of real, raw memories that couples can relive for the rest of their lives.
We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
One of the biggest lessons I’ve had to unlearn is the fear of simply being myself. I grew up struggling with social anxiety and was always that quiet, shy, reserved kid who felt uncomfortable speaking up. For a long time, I believed that being quiet or unsure made me “less than” in some way. Any time I tried to open up, I’d overthink it, feel embarrassed, or tell myself I said something stupid. It created this feedback loop that just made me close off more.
Photography — and my now wife Angela — changed everything for me. When I first picked up a camera, it gave me a reason to step outside my comfort zone. I started photographing people, spending time in more personal, intimate settings, and connecting with complete strangers through my lens. In those moments, I slowly stopped worrying about being “too quiet” or not saying the perfect thing. I was just present.
Angela played a huge role in that journey too. She helped me learn to let my guard down and embrace who I am. Over time, I realized that my quiet, observant nature wasn’t a weakness — it’s part of what makes me a good storyteller. Photography gave me direction, helped me understand my values, and most importantly, taught me that I didn’t need to perform for anyone. I just needed to be myself.
Is there something you think non-creatives will struggle to understand about your journey as a creative?
I think one of the biggest things everyone can relate to, especially creatives, is how heavy the idea of perfection can weigh on you. As creatives, we often chase this imaginary finish line — the perfect project, the perfect piece of work, that moment where it all finally clicks and you feel “ready.” But the truth is, that moment doesn’t really exist. Perfection is a moving target. You can get stuck in this endless feedback loop of waiting for the right time, the right place, the right people, or for it to finally feel just right — and meanwhile, nothing actually gets finished.
I’ve learned that imperfect action will always be better than perfect inaction. You can chase an ideal forever and never get anywhere. The work you’re creating right now won’t even compare to the work you’ll be capable of two, three, or five years from now — but you’ll never reach that point if you don’t just start and finish.
It’s almost never the perfect time. It’s messy, uncomfortable, and way less serious than we make it in our heads. But that’s what’s liberating about it. Once you let go of trying to make it perfect, you open the door to actually growing. Every project — even the imperfect ones — becomes a stepping stone to something better.
Contact Info:
- Website: https://www.j-a.wedding/
- Instagram: https://www.instagram.com/jaweddingphoto/
- Youtube: https://www.youtube.com/@jaweddingphoto
Image Credits
All credits to myself and J&A