People love asking entrepreneurs about their “big break” moment—that one decision or opportunity that changed everything. But here’s the truth: my journey from Air Force combat photojournalist to building a digital media company that got acquired wasn’t one moment. It was a series of messy, uncertain steps that only made sense in hindsight.
So let me walk you through the full arc. Not the polished LinkedIn version, but the actual story—complete with the detours, mistakes, and moments where I had no idea what I was doing.
The Foundation: Combat Camera (1990s)
I joined the U.S. Air Force as a combat photojournalist, which is exactly as intense as it sounds. My job was documenting military operations in places where things could go sideways fast. You learn some valuable lessons when you’re shooting in environments where mistakes have consequences.
The military taught me discipline, obviously. But more importantly, it taught me how to operate under pressure, how to tell stories that mattered, and how to strip away everything that doesn’t serve the mission. Those skills became the foundation for everything I built later.
What I didn’t realize at the time was that I was also learning how to build systems. The military runs on processes, workflows, standard operating procedures. You don’t wing it when lives are on the line. That mindset—building reliable systems that work under stress—became core to how I approach business.
The Transition: Finding My Footing (Early 2000s)
Transitioning from military to civilian life is… awkward. Nobody tells you how weird it feels to suddenly not have structure, chain of command, or a clear mission. I went from combat operations to trying to figure out how to make a living as a photographer.
I did what most photographers do—hustled for gigs, shot everything, built a portfolio, tried to network. But I kept hitting the same wall: I knew how to take great photos, but I didn’t know how to build a sustainable business. And more frustrating, nobody was teaching that part.
Photography schools taught technique. Online forums talked about gear. But nobody was having honest conversations about pricing, marketing, client management, scaling, or building something that didn’t require you to shoot constantly just to stay afloat.
That gap bothered me. A lot.
The Pivot: Starting This Week in Photo (2008)
I started This Week in Photo (TWiP) in 2008, back when podcasting was still this weird thing you had to explain to people. “It’s like a radio show, but on the internet, and you download it…” Yeah, it was like that.
TWiP wasn’t supposed to be a business. It started as a way to have the conversations nobody else was having—real talk about the photography industry, technology shifts, business strategies, and where things were heading. Not gear reviews. Not inspirational fluff. Actual useful information.
The response was immediate. Photographers were hungry for this content. They wanted to understand the business side. They wanted to know how to adapt to digital, how to work with brands, how to build sustainable careers. We built a community, not just an audience.
But here’s what’s funny—I still didn’t think of it as a “real business” for years. It was just this thing I was doing because it needed to exist. Classic entrepreneur move: build something valuable, then spend way too long figuring out it’s actually a business.
The Evolution: Building Multiple Revenue Streams (2010s)
As TWiP grew, I started experimenting with different models. Sponsorships. Membership programs. Educational content. Live events. I was testing everything, seeing what worked, iterating constantly.
What I learned during this phase shaped everything that came after:
- Community beats audience – People don’t just want content, they want connection
- Education scales – You can only shoot so many photos, but you can teach infinitely
- Systems > hustle – Working harder isn’t the answer, working smarter is
- Diversify or die – Relying on one revenue stream is terrifying
This is also when I developed what I now call VanOS—my personal operating system. It’s the framework that connects everything I do: analytical thinking + creative execution + entrepreneurial strategy. Military discipline meets creative experimentation meets business pragmatism.
I needed VanOS because I was juggling multiple projects, trying to scale without burning out, and constantly adapting to industry changes. The framework helped me make decisions, prioritize ruthlessly, and build systems that actually worked.
The Validation: SmugMug Acquisition (2022)
In 2022, SmugMug acquired This Week in Photo. That sentence is surreal to write, even now.
The acquisition wasn’t something I was actively pursuing. SmugMug reached out because they saw what we’d built—not just a podcast, but a real community, a brand that mattered in the photography space, and a platform that had proven it could sustain itself.
The negotiation process was educational, intense, and honestly kind of terrifying. You’re essentially putting a price on something you built from nothing, trying to value intangible things like community trust and brand equity. There’s no formula for that.
What I learned from the acquisition:
- Build for value, not exit – We didn’t build TWiP to sell it. We built something that mattered. The acquisition was a byproduct of that focus.
- Community is everything – What SmugMug valued most wasn’t the podcast tech or the content library. It was the community we’d built and the trust we’d earned.
- Timing matters – The deal happened when it made sense for both sides. Forcing it earlier or later wouldn’t have worked.
- Have good advisors – I had lawyers, accountants, and mentors who helped navigate the process. You can’t do this alone.
Selling TWiP wasn’t the end goal. It was more like… clearing the deck. Creating space to build what comes next.
The Expansion: MediaBytes and Beyond (2020s)
After the acquisition, I launched MediaBytes—a modular education platform for creative professionals. It’s everything I learned from TWiP, distilled into practical, implementable systems.
MediaBytes exists because I kept seeing the same problem: creatives drowning in motivational content and surface-level tips, but starving for actual systems that work. How to build workflows that scale. How to use AI without losing your creative voice. How to create content strategies that don’t require being online 24/7.
I’m also consulting with brands and creators, serving on the board of the International Photography Hall of Fame, and building new projects. Multiple revenue streams, multiple impact points, all connected by the VanOS framework.
The Real Lessons (What I’d Tell My Younger Self)
If I could go back and talk to the photographer who was struggling to figure this out in the early 2000s, here’s what I’d say:
1. Build systems, not just skills
Your creative talent is important, but your ability to build reliable systems is what scales. Learn both.
2. Community is your moat
Platforms come and go. Algorithms change. But genuine community relationships? Those last. Invest there.
3. Embrace the messy middle
That period where you’re not a beginner but not yet “successful”? That’s where the real learning happens. Don’t rush through it.
4. Multiple revenue streams = freedom
Never depend on one source of income. Diversify intentionally.
5. Your military training matters
If you’re a veteran, those skills—discipline, systems thinking, operating under pressure—are massive advantages in entrepreneurship. Use them.
6. The gap you see is the opportunity
That thing that bothers you, that missing piece nobody’s addressing? That’s your business idea. Build it.
7. It takes longer than you think
TWiP took 14 years to get acquired. MediaBytes is still growing. Digital empires aren’t built overnight, despite what social media suggests.
What’s Next
I’m not done. Not even close. The acquisition wasn’t a finish line—it was validation that this approach works. Now I’m scaling the framework, helping more creatives build sustainable businesses, and exploring new ways to combine creativity with technology.
I’ve got MediaBytes growing, new education programs launching, consulting work with brands who actually get it, and about seventeen ideas I’m testing. Plus two cats who remind me daily that not everything needs to be optimized.
The journey from combat camera to digital entrepreneur taught me that success isn’t linear. It’s messy, uncertain, and way longer than anyone admits. But if you build real value, serve a real need, and stay adaptable, you can create something that matters.
And maybe, if you’re really lucky, SmugMug calls.
The Bottom Line
This is the full arc: Military photojournalist → struggling photographer → podcast pioneer → acquired media company → multiple businesses. Twenty-plus years of building, failing, learning, and adapting.
Your journey won’t look like mine. That’s good—it shouldn’t. But the principles are the same: build systems, serve your community, stay adaptable, and don’t give up when it feels messy.
Because it’s supposed to feel messy. That’s how you know you’re building something real.
