We were lucky to catch up with Leo Sideras recently and have shared our conversation below.

Leo, thanks for joining us, excited to have you contributing your stories and insights. The first dollar you earn is always exciting – it’s like the start of a new chapter and so we’d love to hear about the first time you sold or generated revenue from your creative work?

The year is 2019 and I’m planning a trip from Denver, CO to South Lake Tahoe, CA with my sister to link up with some friends for a week of skiing. At this point, I’ve been talking outdoor & travel photos for the better part of 5 years (albeit as an amateur and for my own personal enjoyment.)

My good friend who worked for a pickle company (The Real Dill) based in Denver, CO knew of my trip and reached out with a proposition – she asked if I would be interested in getting paid to shoot some pickles & bloody mary mix along the way. I said absolutely! She then asked what would I charge? I froze for a second and thought to myself ‘wait, am I actually getting paid to make some photos?’ I simply couldn’t believe it. For the first time I was experiencing what it was like to be a free-lance travel photographer. How freaking awesome was this!

I went on the 2-week road trip with my sister and made photos of pickles and bloody mary mix at epic locations including the Bonneville Salt Flats, South Lake Tahoe, and Zion National Park. My friend & The Real Dill were stoked on the photos (to this day I still am myself!) I ended up delivering somewhere around 27-30 photos from three incredible locations. This was all it took to get me hooked on product/travel/outdoor photography.

Leo, 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 arrived at photography/videography in a sort-of roundabout way. Growing up in Ohio, I studied music pretty much my entire life – really from the age of five through my early twenties. I’ve always had a creative itch and simply needed some form of creativity in my life to be happy. I began making photos while studying music production at Ohio University – during my time at OU I was heading to Malaysia for a month to run audio on a film through a study-abroad program and wanted a camera to take with my. My aunt was the only photographer I knew so I hit her up for some advice – to my surprise she sent me her Canon 35mm film camera! This was really the beginning of my experience with photography. It wasn’t until the fall of 2021 where I decided to switch professions and pursue photography/videography full-time!

My photography/videography focus is in outdoors and travel. This focus is rooted in my upbringing and personal love for the outdoors. Some of my earliest memories are of camping & hiking with my family – I absolutely love spending time in the outdoors and capturing its moments! In addition to visual content creation, I pride myself on knowledge of the outdoors and business acumen – my ability to bring both of these skillsets to creative work has proved in valuable. What I enjoy most when working with companies is creating visuals for a campaign or new product launch. I do best when I’m able to dive deep into a project, and I really thrive as projects become more involved.

Is there mission driving your creative journey?

My route to photography is a bit roundabout but my mission in pursuit of creative professions has always been the same.

One of my guiding internal missions is to combine what I love from a creative standpoint with business. I’m really not a person that can fake anything – if I don’t love it I’m not going to put my entire self into it. And if I don’t put my entire self into it, the work doesn’t end up satisfying me. The level of synchronization between art, my passions, and business that I’m seeking is pretty high. I do my best work and am happiest when I’m at this intersection. And yes, I do enjoy the business end just as much as clicking the shutter on my camera!

I love the outdoors, travel, meeting & making friends with incredible people and creating together. So outdoor/travel/lifestyle photography seem to be the best vehicle for me to channel all of this! In my short career I’ve been fortunate to self-produce and film a documentary about coffee in Rwanda and work with a handful of incredible outdoor brands. This fall I’m heading to Colombia for a couple of months to create for a long-time friend’s coffee company. I’m stoked!

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I’m only about 1-year into pursuing photography on a professional level. I’m constantly reminding myself that although I’ve been taking photos for years I’m starting literally from the bottom. No one really knows who I am, I’m still defining my style, and business can be quite irregular. I am constantly learning that I am a beginner, and reminding myself that it’s totally ok. I’m going to make mistakes, my proposals will not always be accepted, and I need to gain the trust and build my reputation. To be honest, I don’t this this mindset will every end for me.

I learned this lesson when I began roasting coffee (I directed a coffee program for 5 years before I switched to photography.) I worked as a barista at a high-end company in Denver, and then moved to roasting for a small start-up. For about a year and a half I had no clue what I was doing. My colleagues gave me honest and candid feedback on my work, which was rarely, if ever, outstanding. I’m so glad I had people in my life that were candid with me – it truly helped me grow. Fast-forward 3 years from when I started roasting and I placed 17th at the US roaster’s championship. Everything is always rough as a beginner, and I’m reminding myself of this as I step into photography/videography.

Contact Info:

• Website: www.leosideras.com
• Instagram: @leo.sideras
• Linkedin: https://www.linkedin.com/in/leo-sideras/
• Twitter: @leosiderasphoto

Image Credits
All images made by Leo Sideras.