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Meet Matt Druin of Matthew Druin + Co. Photography in Woodstock

Today we’d like to introduce you to Matt Druin.

Matt, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
Growing up, I was always super creative through painting, drawing, building things, and shooting / editing video through skateboarding. Photography for me was a total accident. I was actually in college majoring in finance when I traded a tool box for a camera with the intent to resell the camera for more. Being a tech nerd, I fell in love with all the buttons and started taking photos of my dogs, squirrels, and other random things. A few weeks later a friend of a friend offered me $20 to take some portraits. I took that and returned home to tell my wife Jessica that I felt photography was my calling. Naively, I planned to drop out of school and quit my job, so I could pursue photography full time. She was really supportive, but felt since I just got the camera that I should probably wait a year or so to get better and build the business. About three months after owning that camera, another friend of a friend asked me to photograph their wedding. At that point I decided to quit school and my job, and pursued photography full time.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
I feel nothing in life worth having is easy or a smooth road and there’s definitely no shortage of struggles in business. I started the business in 2011 when things in the economy were still shaky. I had a number of people that suggested I should take a safer route of staying in school and getting a “secure” type job. Years before, I was working as a manager at Circuit City and watched that whole ship go down, so I knew nothing was truly safe. Being an entrepreneur has always been a passion of mine, and photography was my third business I owned, and it’s a space I’m comfortable in.

Unlike many creatives, I actually enjoy the business and creative side of what I do, so in that aspect, things were a little easier starting out. In the beginning, one of the hardest things for me was some type of time structure and work / life balance. Like any business starting out, tons of hours of work are generally required. I was working 50-80 hours weekly for the first year or two. Eventually I started feeling burnt out and it was taking a toll on me and my relationships. Nowadays I’ve gotten the business organized and to the point where I outsource things I don’t want to do or are not strong at, have great workflows, set working hours, and things are a lot more manageable. My professional and personal life is way more enjoyable now, but I can often get so excited about work, that I lose track of time. I think the idea of work/ life is hard for most entrepreneurs due to the passion that goes into it. We never shut off totally and are always thinking of some new idea.

Alright – so let’s talk business. Tell us about Matthew Druin + Co. Photography – what should we know?
Our goal is to create a rad experience, creating amazing photographs, and deliver incredible products clients will enjoy for generations. We want people to feel empowered, a boost in self-esteem, and consistently fall in love all over again with the story of who they are and their family every day. We specialize in destination weddings, but also photograph local weddings, as well as, headshots for business, portraits, and Day in The Life family documentaries. Basically, we help people tell the story of who they are, who their families are, and document some of the most important times in their lives. We are most proud of how we are able to impact our client’s lives and how they feel. It’s such an incredible feeling to see people’s reactions to how powerful the photographs they hold truly are.

Is there a characteristic or quality that you feel is essential to success?
It’s hard to pin it down to just a few things, but I feel that my high attention to detail, integrity, work ethic, and drive are some of the most important characteristics to my success. I never like to settle and always want to be learning, growing, and improving the business and the experience my clients receive.


  • Weddings currently start at just $2399 with no travel fees in the continental US
  • Portraits and headshots currently start at just $199
  • Day In The Life Family Documentaries currently start at just $799
  • Products like albums, wall art, and prints currently start at just $25

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