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

Hi Leonard, we’d love to hear more about how you thought about starting your own business?
I’ve always had a love for photography and for capturing people, but in the beginning, I didn’t know exactly where I wanted to land. I experimented with a bit of everything—weddings, wildlife, family portraits, fitness, beauty—you name it. Eventually, I found my way into fashion and spent about a year shooting runway. It helped me refine my eye, but I realized I wanted more control over the creative process. I didn’t just want to document—I wanted to create images that felt uniquely mine.
What started as an expensive hobby turned into a business where I could offer high-quality photography services to both individuals and businesses. Over time, I developed a real passion for headshot photography—helping people show up confidently, whether for a corporate role or a personal brand. As an Army Veteran and retiree, one of the most meaningful parts of what I do is providing free headshot sessions to transitioning military members. It’s my way of giving back to those who’ve served and helping them step into the next chapter looking sharp and feeling confident.

Alright, so let’s move onto what keeps you busy professionally?
What sets me apart from other photographers?
My work is all about capturing authenticity with intention—whether that’s a polished headshot or a bold editorial fashion portrait. I don’t just take pictures; I collaborate with my clients to create images that feel real, confident, and unique to them. It’s that connection and attention to detail that helps people show up fully in front of the lens.

How did I get to where I am professionally?
It wasn’t a straight path, that’s for sure. I started out experimenting with everything—weddings, wildlife, fitness, family portraits, and runway fashion. Each genre taught me something different, but ultimately it was headshots and editorial fashion that aligned with both my creative vision and the experience I wanted to give my clients. It took trial, error, and a lot of patience to find my lane.

Was it easy? Not at all.
Building this business has meant staying humble, learning constantly, and always putting my clients first. I’ve made it a priority to keep growing by attending photography conferences, learning from mentors, and working hands-on with fashion designers, models, and community organizations. That commitment to learning keeps my work fresh and my creative energy flowing.

What am I most proud of?
It’s the trust my clients put in me and knowing they leave their session feeling seen and confident. I take that seriously. Whether they’re stepping into a new career, launching a brand, or just want to feel good in front of a camera—I want them to love their images 100%. That’s the standard I hold myself to, every single time.

What do I want the world to know about me and my brand?
Leonard Anderson Photography is built on connection, creativity, and service. As a retired Army veteran, one of the most meaningful things I do is offer free headshots to fellow service members transitioning into civilian life. This brand isn’t just about beautiful images—it’s about empowering people, telling real stories, and leaving a positive mark in the community.

What’s the bigger vision?
I’m building more than a business—I’m building a legacy. One that blends creative excellence with purpose and impact. Whether I’m working with individuals or brands, my goal is to keep growing, keep serving, and keep creating work that matters.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
Here’s how I’d spend a week showing someone what Denver (and the surrounding areas) is really about—through my eyes, my camera, and my smoker.

Day 1 – Welcome to Denver
We’d kick things off with brunch at Sam’s No. 3—a Denver classic with a solid menu and fast service. After that, we’d cruise through the RiNo Art District to check out street murals and grab a brew at Ratio or Our Mutual Friend. For happy hour, Perry’s Steakhouse delivers with their signature pork chop, salmon, and lobster bisque. We’d end the night at Ophelia’s Electric Soapbox catching live music in one of the city’s coolest venues.
Photo Tip: RiNo’s bold backdrops make it a great spot for creative street portraits and urban candids.

Day 2 – Red Rocks & Backyard BBQ
We’d explore Red Rocks Amphitheatre, whether there’s a show or just a walk through the park—it never disappoints. After lunch in Morrison, it’s back to the house where I fire up the Yoder smoker. The spread? Ribs, cedar plank salmon, Italian sausages, burgers, and hot dogs. It’s the kind of chill evening where conversation flows, and Smokie waits patiently for a dropped bite.
Behind the Lens: Some of the best photos happen in between bites—sunset light, rising smoke, and relaxed moments shared over good food.

Day 3 – Creativity & City Lights
We’d dive into Denver’s creative side with stops at the Denver Art Museum, Meow Wolf, and a stroll through the Santa Fe Art District. Dinner would be up at El Five, known for its skyline views, Mediterranean tapas, and cocktails worth sipping slow.
Visual Vibe: Art and architecture mix well—great spaces for capturing detail, energy, and personality in portraits.

Day 4 – Boulder, Golden & Unexpected Beauty
We’d take a day trip to Boulder for the Celestial Seasonings factory tour, then stretch our legs at Chautauqua Park. From there, it’s down to Golden to tour the Coors Brewery, people-watch, and soak in that small-town energy. If there’s something good playing, we’d catch a show at the Lone Tree Arts Center.
Shoot Note: Golden offers rustic, story-driven backdrops. Think old brick, soft light, and genuine moments.

Day 5 – Studio to Park Shoots
We’d start with a headshot session in my studio—simple, clean, dialed-in lighting to bring out your best. Later in the day, we’d move into a lifestyle shoot at City Park, Wash Park, or the park near Denver Botanic Gardens for some golden hour magic. For eats: burgers and craft brews at Bad Daddy’s, and a steak dinner at Del Frisco’s to wrap it up—yes, with that legendary butter cake.
Creative Focus: These are my favorite sessions—where I get to show people how powerful a great portrait can be, on their terms, in real spaces.

Day 6 – Garden of the Gods & Roadside BBQ
We’d hit the road to Colorado Springs and take in the epic landscape of Garden of the Gods. It’s one of those spots that makes you stop and just breathe it in. Afterward, we’d swing by Rudy’s BBQ for a casual but solid lunch. It’s a day that leaves your legs a little tired and your camera full.

Day 7 – Vail Wind-Down
For the final day, we’d cruise up to Vail—because no trip to Colorado feels complete without some time in the mountains. First stop: Yeti’s Grind for coffee, then a slow stroll through Vail Village. No agenda. Just soaking in the views, snapping a few last shots, and closing the trip on a high note.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
There’s no way I’d be where I am without the support, mentorship, and collaboration of a whole crew of people. My family has been the backbone of everything, especially my wife and daughter, who’ve both been incredibly supportive (and sometimes my test subjects whether they volunteered or not). My dad’s been my go-to conference wingman, and my “Sistah” Tennisia has played just about every creative role—modeling, HMU, styling, and dreaming up killer concepts that pushed my work in bold directions.

I’ve been lucky to learn from and collaborate with some incredibly talented folks along the way. Fashion designer Troe Williams of Vandalism Designs has been a huge creative force—his designs, including that unforgettable pink parachute dress, brought a whole new level to our shoots. He’s been a constant supporter and collaborator, including on the first-ever fashion show at Prince’s Paisley Park, where I was honored to be one of the few photographers invited.

Photographer Craig Lamere has been another big influence—always willing to share tips and tricks of the trade, and keep things fun at the same time. I also owe a lot to my photography mentors like Don Hales, Brett Seely, Tony Rocco, Sal Cincotta, Christopher Mikals, Peter Hurley, and Gary Hughes. And I can’t forget the communities that shaped me—my Shutterfest and the Headshot Crew family have been instrumental in pushing my skills and building real connections in this industry.

Website: https://leonardandersonphoto.com/

Instagram: https://www.instagram.com/leonardandersonphoto/

Linkedin: https://www.linkedin.com/in/leonard-anderson-366814186/

Facebook: https://www.facebook.com/leonard.anderson.photo

Youtube: https://www.youtube.com/@leonardandersonphoto357

Other: https://headshotcrew.com/u/LeonardAndersonPhoto

Image Credits
All images copyright Leonard Anderson Photography, LLC.

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