In the mountains of Colorado Springs, surrounded by trails, pine trees, and sixty of the most influential cybersecurity leaders in the country, I had the opportunity to be part of something rare and impactful: three days of a uniquely refreshing experience and executive headshots that actually look like the person within them.
What Is CISO Ascent?
Twice a year, in the rugged wilderness of America’s most iconic landscapes, a group of chief information security officers and cybersecurity leaders gather for a multi-day retreat. The group has included leaders from organizations like UPS, Zoom, DocuSign, and Kimberly-Clark, as well as city and state government offices.
The mission is simple: put down the weight of one of the most demanding roles in corporate America and build genuine community with people who actually understand what that weight feels like.
That’s CISO Ascent.
CISO Ascent was founded by Bryce Carter, CISO for the City of Arlington, and Tyler White, VP of Strategic Partnerships. When they reached out to me, it wasn’t as a photographer — it was as someone aligned to their mission: A focus on what makes us human. That alignment is what started this partnership, and it’s what has made every trip something I look forward to long before I board the plane for the wilderness.
I’ve been part of CISO Ascent since the beginning and I don’t take that lightly.
Three Days in Colorado Springs
Most recently, the group gathered in Colorado Springs, where we hiked the Seven Bridges Trail and rode the historic Manitou and Pikes Peak Railway through some of the most dramatic scenery in the American West.
Over three days, I watched as sixty professionals shed their titles and just became people. Conversations rang out on the trail that had nothing to do with security frameworks. Laughter echoed on the railway. Quiet moments of reflection reminded everyone why they work as hard as they do.
I served as a documentarian and captured the candid moments, the group energy, and the small details that made a trip like this feel unlike anything else on a corporate calendar.
The Headshots Nobody Planned On
Before the trip, two leaders had the foresight to book sessions with me in advance: Dan Wordell, CISO for the City of Spokane, and Randolph Barr, CISO for Cequence Security. They knew what they wanted and they came prepared.
We set up in a simple hotel conference room that was unassuming and unglamorous (exactly the kind of space you’d walk past without a second thought). I brought a mobile studio backdrop and my lighting kit. Within minutes, it became something else entirely.
Randolph arrived in a suit. The first few frames were clean and professional; exactly what his role sometimes requires. Then he took the jacket off, loosened up, and we kept going. Dan came in his quarter zip and a t-shirt, completely himself from the start. Neither session looked like what most people picture when they hear the word “headshot.” Both sessions produced portraits that felt true to who these men actually are: confident, grounded, and human.
Then something unexpected happened.
When three other attendees saw the results, they didn’t hesitate. Three leaders, on the spot, paid for sessions they hadn’t planned on. Not because they were talked into it, but because seeing Dan and Randolph’s photos made them realize something: you don’t have to look like a different version of yourself to look powerful.
What made it work wasn’t the location. Instead, it was the way we moved through the session, the prompts that drew out genuine expressions, and the willingness to let the portrait reflect personality rather than perform professionalism. A hotel conference room with a mobile studio. Portraits that stopped people in their tracks.
That’s the point. I can work anywhere. What I bring with me is what matters.
After the trip, I received a text, unprompted:
“You should change your title to magician… These are the best pictures I ever had — even better than my wedding pictures. I always doubted my portraits, they never looked like me. Muchas gracias for making me look good.”
That’s the whole mission, right there.
Why This Matters Beyond the Mountains
Based in Dallas–Fort Worth, I work with executives and leaders across the DFW metro every day. But what CISO Ascent reminds me — on every single trip — is that the best portraits don’t come from the right location or the most elaborate setup.
They come from the right relationship. The right moment. A subject who finally feels comfortable enough to stop performing and just exist in front of the camera.
That’s what I bring to every session I shoot in Dallas. The same patience. The same approach. The same commitment to making you look like you — not a polished, corporate approximation of you.
What’s Next
Next on my calendar for CISO Ascent? Yellowstone National Park this fall and I can’t wait.
CIO Ascent also launches this fall — bringing the same mission and community to chief information officers — and I’m excited that I’ll be part of that journey as well.
Three days. Sixty leaders. One experience that changes how you see yourself.
If you’re ready for headshots that actually look like you, let’s talk.