Some surprises just creep up on you.

As a 48-year-old seasoned business guy, you'd think I'd have seen it all. I've been through three startups. One was a home run and two solid triples. Now, I'm the CEO of another tech early-stager in Colorado.

We have about 20 employees and we're all housed in one big room in a nondescript office in the neverland between Boulder and Denver. We're not quite serious enough for the big city and not quite hip enough for the college town.

We do most of our development in-house. We outsource a few specific projects, but for the most part our platform is a dish of home cooking. These five or six developers camp themselves in the rear of our space which they've creatively dubbed "The Back of the House." Their headphones give them all a Princess Leia-like look, especially with the lights dimmed to some winter shade of dusk. They plow through lines of code indecipherable to me. They conduct standups, complete sprints, run tests, and Slack the person sitting feet away.

I intentionally invade their little world from time to time.

I'm the bridge between our tech group and customer facing group. I want to communicate all the cool stuff that's about to happen in non-tech language. I also want to push our tech guys to understand what value they're birthing. I like to push them to be able to articulate our company's role in changing the video landscape.

Our youngest developer is a kid named Dan. Originally from Maine, Dan fits the stereotype. Twenty-something, flannels, a stocking cap, a fuzzy face, and low-hanging jeans are his uniform of choice.

Dan has always been a little awkward in our let's-talk-about-marketing-stuff sessions. A little unsure of himself. But, he's also the kind of character I sometimes oddly relate to. I take my CEO role as mentor to the next generation seriously. As I've spent more time with Dan, I've been able to pry away some of the layers. And part of me started wondering if he was playing this part because being underestimated was his preferred state.

I was recently invited to an executive lunch in Denver. For some of these events, I like to drag someone from the team along. I think it's good to push our less seasoned folks outside the comfort zone. This is usually an easy exercise for sales and marketing folks. But, tech people? Not so much.

Dan and I just barely arrived on time. I could see right away that it was choked with C-level types. A bit higher-end than normal. I panicked a bit inside. What had I gotten us into? What had I gotten Dan into? As we made our way over to our table, I was distracted by a friend. Just some simple pleasantries, but it was enough for Dan to get ahead of me. As I approached our otherwise full table, I could see the networking-happy fellow to Dan's right engage him.

"And, what do YOU do? Who are you here with?" he asked with just the slightest tinge of condescension.

The room seemed to quiet. My panic attack nearly turned to a cardiac event as, almost in slow motion, I watched Dan turn to respond. Our coveted first impression was about to be delivered by an awkward developer wearing jeans and a stocking hat.

And then, something amazing happened. Dan proceeded to deliver the best explanation about our little startup I've ever heard. It was certainly better than any I've done. It was simple and direct. He was understandable and engaging. I sat back and witnessed a conversation between a group of high-on-themselves executives and a lone wolf. In the end, they all would have signed up for our thing on the spot. Dan, as it turns out, was also a closer.

When we returned to the car, I had to say something.

"Dan, that was awesome," I told him. "Don't take this the wrong way, but that really surprised me. You really handled yourself well in there. The way you explained Intelivideo and what we're about. I was just... impressed."

I struggled for the right words. I didn't want to gush, nor did I want to underplay it. It was an experience I was having trouble capturing in a quip. Dan simply said thanks. He was seemingly unimpressed with how impressed I was.

It seems whenever I think I have it all figured it, a Dan shows up.

That's what the entrepreneurial journey is all about: becoming comfortable with being surprised. And learning new things. The sometimes-painful sessions where I force tech folks out of their comfort zone? They're worth it.

And, don't underestimate Dan.

Published on: May 2, 2017