Winpaid member Lindsey Roman has come a long way from the days of offering free photoshoots. Her work has been featured on sites like CNN, Yahoo and People, as well as on multiple talk shows. As a destination wedding photographer, Lindsey’s created her dream job, adventuring around the world and capturing couples’ love stories. Here, she shares how she built her portfolio to attract her ideal clients, the double-edged sword of the hustle and the best business investment she’s ever made.
Please tell us a little bit about yourself.
Hi! My name is Lindsey Roman, and I’m a destination adventurous wedding and elopement photographer based in Oahu, Hawaii. I’ve been a photographer for nearly 10 years and full time in this business for two years. I’m a Jesus lover, a black coffee drinker, and a free spirit; I’m obsessed with nature, national parks, and exploring every inch of this beautiful world we live in. Oh and I dance. A lot. On Instagram and elsewhere.
How did you start your business?
I went to school and double majored in Theatre and Film. I always did photography as a hobby on the side because it was an art form I loved. When I started getting to know my camera better, I slowly started my business on the side. At the time, I was waitressing and working at my church. I went full time just by jumping and deciding to make it work. I know that’s not the “professional” or helpful answer, but it’s my truth. I knew wedding and elopement photography was what I had a natural talent for, and it was what I loved. I knew I could do it if I worked hard at it, so I jumped. I hustled like hell that first year. The biggest adjustment with doing it that way was that everything I made went directly to rent, bills, and food. My husband and I lived super minimally on a strict budget at that time, and slowly but surely that hustle and diligence paid off. Now it’s so much more successful than I ever could have imagined.
How did you build your portfolio when you first started out?
I started my photography business back in Kansas where I used to live before we moved to Hawaii. I knew pretty early on that I absolutely LOVED the raw, adventurous, candid style of photography. That style comes to life most beautifully for me when I’m capturing intimate outdoor weddings and adventurous elopements. It was a struggle early on to build a more “adventurous” portfolio in the middle of Kansas.
I intentionally took trips to places I wanted to shoot, and I would do everything I could to set up styled shoots, free shoots, or cheap shoots in those places. To try and find couples, I would post on Instagram, in Photography Facebook groups, and on my personal Facebook, and reach out to friends of friends who lived in the area, literally anything. The value of having portfolio work in the mountains, the desert, or the ocean was worth it to me to offer a session for cheap or for free at the time. Now that I live in Hawaii, finding epic locations isn’t quite as hard as it used to be, but building that base even in Kansas jump-started me in the direction I wanted to go successfully.
What are your career highlights?
A session I shot of Jenna and Drew Kutcher went mega viral—like CNN, Yahoo, People, Perez Hilton, multiple talk shows, etc. That was incredible.
What’s your favorite HoneyBook feature?
Can I say everything? I just love that everything I need for client workflows are all in one place. I can send online invoices, online contracts, set up reminders for follow-up emails, see my calendar, and more all in one spot. It has everything. HoneyBook is easily the best business investment I’ve made in order to work less and live my life more.
Where’s the craziest place you’ve ever had a shoot?
I love this question so much because being an adventurous destination photographer, I’ve shot in a LOT of places. I’ve shot on a glacier, in the ocean, on top of mountains, in slot canyons, on islands, like everywhere. I think my most recent favorite was last month in Scotland. I stayed with my couple at their home in St. Andrews, Scotland, and then the next day we road tripped up to the Scottish Highlands to the Isle of Skye. We ended at the Fairy Pools—Google them, they’re GORGEOUS—and it was foggy and misty and cold in July, and it was just the coolest thing to experience together. I think for every new destination I shoot in, I learn (ironically) that you can have the most incredible location,
but if the connection with your client isn’t there, the photos won’t turn out that good. Connection and relationships rule over everything else. Which is why I make this a HUGE priority to connect and get to know my couples long before I ever lift up the camera to their faces.
What’s something that’s surprised you recently in business?
Recently I’m surprised by the power of the hustle and how it can overwhelm and destroy us at the same time. When you first start as an entrepreneur, your entire mindset is HUSTLE. Your mindset is “MORE MORE MORE” because you’re starting from ground zero. It recently snuck up on me, but I’ve been saying “MORE” for so long and giving out way too many yes’s in my business, that it’s overtaken my personal life. For every “yes” I’m saying to a session in Europe or a wedding in Texas, I’m simultaneously saying “no” to time with my husband, quality chats with friends, time spent actually resting. I was surprised that I was getting burnt out and overwhelmed by work I love. Which just proves that too much of a good thing can actually be a bad thing.
What’s been one of your most successful projects?
I recently started doing photography workshops called The Heart Workshop with my friend and fellow photographer, Evie Rupp. We both have a heart for pouring into other female entrepreneurs, especially in the photography business where it can get so overwhelming to be your own boss in this sea of over-saturation and comparison online. We wanted to create a retreat-like workshop where us and a bunch of female photographers come together, learn new business skills, fellowship with one another, and feel refreshed to get back out there and kill it. We launched the first workshop back in January and it sold out in a couple of hours. That workshop was in April and it went better than our wildest expectations so we launched two more workshops for this winter in Hawaii. Both of those sold out in less than two hours. God has been blessing this dream like CRAZY, and we’re so thankful enough girls out there are interested and are vibing what we’re all about.
What do you do or where do you go to get inspiration?
I find a lot of my inspiration comes from my faith in God, especially when I’m in nature. Standing on a secluded beach looking out into the ocean just overwhelms me in the best way. That the God of the Universe who created the ocean as vast and incredible as it is, also created you and me with a beautiful purpose; the God who thought mountains into existence also loves us with an undying love. That will never stop inspiring me to create art that reflects His love for us, that reflects the beauty of this world He gave us to take care of. Gahhh I could go on all day. 🙂
What’s a photography trend that you’re really enjoy?
I am OBSESSED with underwater photos. Ever since I moved to Hawaii, I’ve loved following and being inspired by underwater photography. It’s SO hard and a completely different beast to tackle than anything above water. I bought underwater housing when we moved here, and I’ve used it for couple sessions playing in the water, but I’m excited to try and get more comfortable shooting fully underwater.
I probably should figure out how to hold my breath for more than 3 seconds first… haha.