Meet Libby Dollar | Photographer, Business Owner, Coach

We had the good fortune of connecting with Libby Dollar and we’ve shared our conversation below.

Hi Libby, what led you to pursuing a creative path professionally?
I guess I’m one of the few lucky people who gets to do the creative thing I know I was meant to do from an early age.

The funny thing is,I’m a wedding photographer, but I didn’t actually pick up a camera until after college. The creative thing that’s always been in my heart is actually running a business–which requires me to think creatively and make things everyday.

My grandmother (a businesswoman herself–she turns 90 this year and has a side hustle flipping houses) introduced me to the word “entrepreneur” when I was 9. I had proffered a catalogue for a business idea I’d had about decorating post-it notes with rubber stamps for a fee. She gamely ordered a few sets for her office, and gave me a little advice about supply and demand. She nurtured my enterprising heart from a young age. Without her, I don’t know if I would have had the audacity to work for myself, but it’s been 16 years since I started my photography business and I can’t imagine doing anything else.

I was also a deeply artistic kid. I drew, sang, and performed constantly, and eventually studied acting, dance, and even majored in music in college. I still love all the arts–particularly theatre, which I draw on for my work with weddings. Photography was the last in a long series of creative pursuits and the one that feels the most like second nature to me.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
The growth of my business has been neither straightforward nor rapid. I think many people out there have a similar experience, but the stories we hear make us think if we’re not an overnight success, we’re failing. Learning how to believe in myself and live according to my values, (whether times are high, or we’re in umpteenth economic downturn of my adult life) has been tricky, but worth it.

I became interested in wedding photography after I married my first husband in 2006 when I was only 20 years old. I HATED my wedding photos, and that disappointment eventually turned into trying to make sure other brides didn’t have the same experience. I wanted to feel comfortable in front of the camera. I wanted to recognize my own smile in the photos–instead of a dazed, frozen, drivers-license type smile. I wanted to feel like a unique individual as a bride, and not just the photographer’s third obligation that weekend.

My driving force was empathy for brides–brides I hoped to save from the negative experience I’d had. Because of this, I avoided a lot of the pitfalls that some young business owners fall into. I didn’t dramatically overbook myself and then have to break contracts to keep from drowning. I let SO MANY trends pass me by without jumping on the bandwagon. I certainly missed a few good opportunities too. I have been surprised over the years at how unusual I truly was leading with my values more than ambition or following the pack of what other wedding photographers. I grew very slowly, but I also worked with so many clients I genuinely cared about and learned from them.

I also didn’t realize how much adversity I had to deal with in the early years. I had a 3 year old daughter, and though I was married to a man who was verbally supportive of my career, he routinely discouraged me from taking any steps that would inconvenience him or threaten to outshine him. I still somehow managed to be the only breadwinner and primary parent for more than a decade. I imagine this phase of my career like a runner training with a parachute behind them–harder than it had to be, so now I’m stronger than I might have been.

My first marriage eventually ended, which is an odd feeling when weekend after weekend I still had to document other people’s joyful beginnings. Fortunately the freedom I felt quickly outshined any sense of loss. I’ve changed my business name back to my maiden name (Dollar) , and I’ve added my current husband–a talented photographer, steadfast friend, and the biggest supporter I’ve ever had–to my team.

Since the name change we’ve photographed weddings together in Europe and the Caribbean, as well as many uniquely gorgeous local weddings in Colorado and other states. I can’t wait to see what we’ll do next.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
My favorite place in the world is Telluride, CO, I’d take my guest on a car-camping road trip in the mid-summer or early fall, first stopping in Ouray–because the whole city is so implausibly beautiful. You feel like you’ve been transported to a tiny Swiss village. You can see multiple waterfalls from any vantage point in town. At the Ouray Amphitheater campground, you can get a campsite that at once feels totally private, and also affords you the most stunning view of your life. Sunset on the first day would be the perfect moment for an impromptu photoshoot (before camping makes you too dirty for photos). Within a few steps of the campground we could capture the alpenglow as it hits the ridge on the other side of town.

The next morning, we’d eat breakfast around the campfire (my multigrain pancakes piped out of a ziplock bag with the corner cut off), before packing up and setting off for the hour or so drive to Telluride.

We’d stay in telluride’s “Mountain Village” area (not too busy because it’s not ski season yet), and, after a post-camp shower, take the free gondola into the center of town. The view from the San Sophia Overlook always makes my heart pound a little bit, but that’s kind of the point. The steep but gentle decent through some light fog into the town of Telluride is something everyone should get a chance to experience in their lives.

Once arrived at the bottom we’d head over to “Baked in Telluride” for a slice of pizza and entirely too many doughnuts and cookies. Walking through the pleasantly cool high-mountain air is a treat even in July. After that–dinner at Rustico, where I once dined with my somewhat conservative parents on the day the “Annual Telluride Naked Bike Race.” I will never forget their faces as the nude cyclists sped by our patio table.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
My Husband, Caleb Huber, whose unwavering belief and support has transformed my life and my career.

Website: https://libbydollar.com

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Image Credits
Copyright of all photos owned by Libby Dollar Photography