February 2026 - Monthly Update

February 2026 - Monthly Update

TECH & TRAVEL TIP: RFID Protection

 

BEHIND THE SEAMS: 25 Years In, Back To Where It All Started




MY TRAVELS WITH STRANGE MEN - Part III: The Azores, Dirk Dunlap, and Why This One Was Different

If you’ve read Episodes 1 and 2, my trip with Scott Eddy (born out of a Virgin cruise and the kind of conversations you don’t schedule) and then Glenn Shapiro (Africa + Seychelles, where the scenery was epic but the real story was the time together), welcome to Episode 3.

This is the one where the “Strange Men” concept stopped being a quirky travel experiment and started feeling… slightly dangerous.

Not dangerous in the “we’re doing illegal things” way.

Dangerous in the much more adult way: the risk of traveling with someone who mattered to my business.

The Pandemic Prologue

This trip began with an extra layer of tension that is almost impossible to explain now unless you lived through that era.

It was June 2022. The pandemic was still very much “a thing.” And, if memory serves me correctly, I had tested positive for COVID just a week or two before the trip.

Which created a problem: even if I was no longer contagious, tests could stay positive. The rules were strict, if I tested positive, I would not be allowed to go. I felt great, but I was nervous. The kind of nervous where you’re calm on the outside and just hoping for the best.

I ended up testing at the airport. Negative, I passed. I got on the plane. The trip was on.



And the weird thing is: that initial stress almost helped. Because once you’ve had the “am I even allowed to leave the country?” moment, everything after that feels like a gift.

Who Dirk Was (And Why He Was Chosen)

Dirk Dunlap wasn’t a stranger.

But he also wasn’t a friend I’d spent real time with in a pressure cooker.

He runs MB Sport, one of our key vendors, and at the time he was relatively new-ish to SCOTTeVEST as a production partner. We’d done business together for several years. He did great work. He was dependable. He had always seemed to have our best interests in mind.

We’d had the normal relationship you have with a good vendor: calls, planning, meetings, maybe dinner once or twice when he visited.

But “vendor you respect” and “guy you can travel with for eight days” are not the same category.

And here’s what made this Episode 3 different from Episodes 1 and 2:

With the first two trips, the escape cord was simple. If the vibe was off, you could split. No meaningful consequences beyond awkwardness.

With Dirk, that wasn’t true.

If we didn’t get along, if this turned into one of those trips where you start fantasizing about separate rental cars and separate lives, the fallout wouldn’t just be personal. It could affect SCOTTeVEST. It could affect our products. It could affect a vendor relationship that mattered.

So yes, I was excited.

And yes, I was also slightly nervous.

Because “Strange Men” is fun when it’s low stakes.

It’s a different game when it’s high stakes.


Why the Azores

Dirk suggested the Azores.

I’m going to admit something: I didn’t even know they existed.

The Azores are part of Portugal, an archipelago in the Atlantic that feels like a fantasy version of Earth. Lush, hilly, volcanic, dramatic coastlines, small roads, and the kind of scenery that makes you say, “How is this not more famous?”

We went in June, which is apparently known for rain.

We packed like SCOTTeVEST people pack: thoughtfully, obsessively, and with the quiet belief that we can solve any problem if we have the right gear.

We weren’t sharing a hotel room on this trip, which helped. But we were sharing everything else: rental car, logistics, daily plans, meals, and a whole lot of time together.

And I committed to documenting the trip on Facebook, photos, videos, little recaps, because part of this entire Strange Men series is letting the story unfold in public.

(And yes, it still annoys me that Facebook deleted so many live videos. I have them downloaded elsewhere, unfortunately without the same neat date organization, but if I ever turn Strange Men into a Netflix-style series, those clips will matter.)

The Goal We Didn’t Expect

On Day One, I asked a question I like asking on these trips:

“Do you have any goals for this week? Anything you want to work on?”

And the hilarious part is that we didn’t even need to say it out loud.

We both looked at each other, two middle-aged men with desk bodies, extra chins, and the quiet recognition that hiking is a great idea until you actually do it.

We both said, almost simultaneously:

“I want to lose 20 pounds.”

So we made a pact.



We would eat well, but we would hike. A lot. And not “cute little walk” hiking. Real hiking.

We turned it into a bet, a public bet that mattered. Not just because of pride. Because accountability between two men who don’t fully know each other yet is a fascinating thing. You don’t want to disappoint yourself… but you really don’t want to lose to the other guy.

What the Azores Felt Like

The Azores are green in a way that feels almost unfair. The hills roll like someone designed them. The air has that ocean freshness that makes you feel healthier even if you’re currently sweating through your shirt and regretting every croissant you’ve ever loved.

The people were great. The food, often amazing. The history interesting. The vibe: small, European, quaint, and strangely modern at the same time.

Also: we had better cell service than we deserved.

That fact becomes important later.

The Hiking Wasn’t Hiking

When I say we hiked, I mean we were doing something like 8–15 miles a day, nearly every day. Up hills, down ravines, along rocky edges, through landscapes where the “trail” is more of a suggestion than a fact.

There were many notable hikes, so many that the trip becomes a blur of cliffs, lush valleys, coastline, and sweat.

But two experiences stand out as “Strange Men canon.”


The Ravine / Ocean / “We Might Die” Hike

There was one hike where we got off the beaten path, either by accident, overconfidence, or the usual dangerous combo of both.

We ended up down in a ravine and somehow along the ocean in terrain that felt increasingly wrong.

We hadn’t worn enough sunscreen. We hadn’t brought water. And the longer we went, the more obvious it became that we were committed to the bad decision. 

At some point the vibe shifted from “adventure” to “math.”

As in: “If this goes sideways, what’s the plan?”

And here’s where it gets real: I was texting Laura while this was happening.

Not dramatic texts. Not “call the authorities.”

More like the modern version of leaving breadcrumbs: “Here’s where we are. Here’s what’s happening. If I stop responding, assume I’m stuck between two sharp rocks having a philosophical conversation with a seagull.”

Watch this video I recorded in the moment if you don't believe me.

We genuinely talked about whether we might have to call for help. Helicopter-level help.

And yes, I know that sounds hyperbolic. But that’s what it felt like in the moment. When you’re exhausted and dehydrated and climbing rugged, sharp rock, your brain stops being poetic and starts being practical.

Somehow, we found our way out.

It turned into a four- or five-hour excursion that we did not plan for. When we finally got back, I was proud… and also quietly amazed we hadn’t turned ourselves into a cautionary tale.

The Tunnel That Should Have Been 75 Feet (But Wasn’t)

Then there was the “tunnel hike.”

Someone told us: “Go down this path, you’ll find a little tunnel, walk through it, and you’ll come out to a beautiful lake.”

You hear that and you picture a cute little tunnel. Maybe 25 yards. A quick novelty. An Instagram moment.

What we got instead was a long, dark tunnel with several inches of water, stretching out into what felt like forever, where you can’t see much and your brain starts doing what brains do in the dark:

“Snakes.”

I don’t care if there were snakes. I’m telling you what my brain was doing.

We debated turning back multiple times. We kept going. The tunnel kept going. Here is a video from the middle of the tunnel, not sure if we should keep going or turn back.

We committed. And when we finally came out the other side, there it was: a beautiful lake, like a reward for not panicking.

It was dramatic in the exact way Strange Men trips are dramatic: you choose discomfort, you commit, you question your choices, and then you’re grateful you didn’t quit.

The Relationship Part (The Real Point)

One of the most interesting parts of traveling with Dirk is how different we are.

He has four children. I have none.

I’ve had multiple poodles; he has a full family life with a different set of responsibilities and rhythms.

He’s a fairly religious man. I’m more agnostic.

We talked about morals, values, work, life, choices, kids, marriage, and what matters. The kind of conversations men often don’t have when they’re standing at a trade show booth or emailing about production timelines.



And in between those conversations, we were doing something else: We were living together in a confined structure, not a shared room, but a shared reality. Shared plans. Shared decision-making. Shared fatigue. Shared wins.

And that’s where you learn someone.

Not from what they say they value.

From what they do when you’re tired, wrong, lost, or hungry.

The Water, The Cliffs, and the Moment I Didn’t Jump

There were also moments that weren’t about hiking. One hotel had these natural hot springs. Brown water, the kind of brown that makes you pause until you remember: nature is weird and doesn’t care about your aesthetics.

It was fantastic.

There was also a spot with cliffs and strong currents, one of those places where people jump and it looks amazing, and you realize that if you jump in the wrong place, the ocean will happily teach you consequences.


Dirk jumped in.

I did not.

I’m not ashamed of that. I’m also not proud. It was one of those moments that tells you something about both people. Dirk has a bravery - or a tolerance for risk - that I don’t always share. And I’m okay with that.

The Unexpected Part: SCOTTeVEST Ideas

Somewhere in the middle of all this, between hikes, meals, and near-disasters, we talked a lot about the future of SCOTTeVEST.

Not in a boardroom way.

In a “you have too many hours together, so you end up talking about what you actually care about” way.

We exchanged tons of ideas about clothing, features, improvements, style, and what customers actually want. And many of those ideas have been implemented since then.

That’s a strange side-benefit of Strange Men trips: when you remove the formal setting, creativity loosens up. You stop pitching and start building.

How It Ended

We started this trip as vendor and client. Friendly, respectful, but living mostly in business context.

We ended it as something else.

Not identical humans. Not best friends in a Hallmark sense. But bonded. Tested. Proven. The kind of friendship that comes from shared experience instead of shared convenience.

And here’s the kicker: the relationship didn’t end when we got on planes.

Since then, Dirk has visited me and Laura regularly, Sun Valley, Palm Springs, birthdays, events. We’ve continued doing a tremendous amount of business together, and that portion has grown. At this point, he is a true partner in every definition of the word.



People say, “Never do business with friends.”

I get the logic.

But here’s what I’ve learned: if you can do it right, if you share values, communicate, and respect each other, there’s no better way to do business. The trust is real. The incentives align. And the relationship becomes deeper than a transaction.

This trip proved something for me.

The Strange Men experiment works best when the stakes are real and the outcome matters.

Episode 3 was epic.

And yes, Dirk is ten years younger than me. So I’m retiring “two old fat men.” But I’m keeping the lesson.

Middle-aged. Slightly out of shape. Overconfident. Occasionally lost.

Accidental friends.