MY TRAVELS WITH STRANGE MEN - Chapter One
In November of 2021, I was cooked. Pandemic fatigue. Idaho winter. A year and a half of feeling like the world had shrunk to the size of Sun Valley.
I needed out. Badly.
I didn’t want a big complicated trip. I didn’t want to plan ten moving parts. I wanted something simple that guaranteed movement. So I booked a cruise on Virgin Voyages’ Scarlet Lady. One of their early Caribbean sailings. Adults only. No kids. A suite that didn’t require me to pretend I enjoy bunk beds.
I planned to go alone. I’ve done plenty of solo trips and I’m fine with them. But because the cabin cost basically didn’t change if you brought a second person, I figured: why not invite a friend?
So I did. Short notice. Maybe a week or ten days. I reached out to the usual suspects. Every single one of them had a reason they couldn’t go. Kids, work, life, commitments, or just the deeply rational instinct to not jump on a pandemic cruise with five days’ warning.
At that point I had two choices. Go alone, which I was totally prepared to do, or do something mildly insane that made the trip more interesting.
I chose mildly insane.
I messaged Scott Eddy.
We knew each other from Facebook. I followed his travel life. He’d followed mine. We’d commented here and there. But we’d never met. Never had a meal together. Never broken bread. Nothing. Just internet familiarity.
I wrote something along the lines of: “Hey Scott. I’ve got a suite on the Scarlet Lady. One room, two beds. You’d be sharing a cabin with me. Want to come?”
He looked at his schedule, said he wanted to get out too, and replied, “I’m in.”
That first dinner was surreal. Two grown men, basically strangers, sitting across from each other swapping life stories the way people do on a first date — except with no romance, no awkward expectations, and a lot more honesty. We talked about childhoods, careers, relationships, regrets, dreams, fears. The weird intimacy of being forced to share space turns conversation into something deeper fast. You’re each on good behavior, but you’re also curious. It’s a fascinating dynamic.
The trip itself was a mix of maiden-voyage hiccups and pure fun. Virgin was still ironing out the kinks. They wanted to run everything through an app that barely worked. The ship was full of travel agents learning the product. Great people, but different energy than a ship full of normal vacationers.
We explored islands. I snorkeled. I scuba-dived. I hung out on beaches. I bumped into my buddy Laird on one port and had a mini-adventure.
Then came the dolphin excursion — the one that produced a mutiny.
We spent an entire afternoon scanning the water. Saw nothing. Later the captain casually admitted they had told the cruise line there were no dolphins anywhere near the island, but the cruise sent us anyway because they didn’t want to refund the money.
That did not go over well with me.
Ten of us marched back to guest services and demanded refunds. I have the video. I was laughing and furious at the same time. To their credit, we got our money back, but I’m still not sure if I was leading a protest or starring in a travel sitcom.
The most meaningful moment was meeting Linda (picture of us below!) and Scott Vinton on a beach excursion. She was a flight attendant, he a senior airline pilot, and both longtime SCOTTeVEST customers. We hit it off instantly. It was one of those perfectly random collisions that makes travel feel like fate. She loved the SCOTTeVEST connection, we swapped stories, and it felt like the brand had quietly followed me out into the world and bumped me on the shoulder.
By the end of that week, Scott Eddy and I weren’t “internet friends.” We were real friends. He later visited me in Sun Valley. We made SCOTTeVEST content together. We stayed in touch. And I realized something important.
Traveling with someone you barely know is a kind of accelerant. You learn who they are quickly. You learn who you are quickly. You get out of your comfort zone, and you grow whether you meant to or not. There’s risk in it, sure, but there’s also a special kind of reward.
That trip accidentally launched a series.
Since the Scarlet Lady, I’ve done more than ten Strange Man trips. Some were epic. Some were awkward. A couple were catastrophes that deserve their own chapter just for the therapy value. But every one of them has been a story, and every one taught me something.
If you want the next chapter, keep reading. I’m just getting started. And if you're interested in more photos, check out the summary facebook post here.
MY TRAVELS WITH STRANGE MEN - Part II: Africa, Friction, and the Discipline of Paying Attention
I had just come off a trip that reminded me why I travel at all.
A few months earlier, I’d taken an impulsive journey with Scott Eddy, aka a strange man I barely knew, and it turned out to be unexpectedly meaningful. I came home lighter, not because of what I carried, but because of what I shed along the way. The trip with Scott Eddy, my first strange man trip, inspired me to go on another trip with another strange man.
We were at a dinner party, Glenn and his wife, Vicki, at our house, talking about the world reopening after COVID. He explained that he had a fishing trip planned and several unfilled days beforehand. Safari came up. Africa came up. That sense of now or never hung in the air.
We were at a dinner party, Glenn and his wife, Vicki, at our house, talking about the world reopening after COVID. He explained that he had a fishing trip planned and several unfilled days beforehand. Safari came up. Africa came up. That sense of now or never hung in the air.
So when Glenn mentioned Africa and the Seychelles, I didn’t hesitate.
“That sounds like fun,” I said.
And I meant it.
“That sounds like fun,” I said.
And I meant it.
Why Africa Was Different
Africa had always been unfinished business for me.
Years earlier, I had planned to go with my father. I believed, and still do, that certain places are so humbling, so overwhelming, that they make old arguments feel small. That trip never happened. My father and I never fully reconciled.
Africa felt like a chance to sit with that reality rather than fix it.
Flying into Johannesburg felt like crossing a threshold. Within a day, I was on a small plane headed toward safari, the kind of travel where every pound matters. Strict baggage limits. No excess. No “just in case.”
This is where I’ll say something practical: traveling in Africa teaches discipline. And having clothing that lets you carry function instead of bulk matters. Pockets replace bags. Weight disappears. Movement becomes easier. That freedom, especially on small aircraft, changes how you experience the trip.
Less stuff. More presence.
Safari: Awe Without Illusion
There are moments on safari that permanently reset your internal scale.
One afternoon, we sat in an open Land Rover, no doors, no barriers, watching a pride of lions feed on the remains of a fresh elephant kill. We were close enough to hear bone crack. Close enough to feel exposed.
No glass. No soundtrack. No illusion of control.
You don’t move suddenly. You don’t speak loudly. You don’t pretend you’re dominant.
You just watch. And you understand your place.
That moment alone would have justified the entire journey.
Traveling With Glenn
Traveling with another man, especially one different from you, accelerates self-awareness.
Glenn is smart, confident, assertive, and unfiltered. Being around him continuously forced me to notice my own reactions. What irritated me. What I tolerated. What I quietly absorbed.
I found myself accommodating more than usual. Yielding space. Letting things slide. At times, I recognized patterns I’d seen growing up, roles I hadn’t realized I still slipped into.
That wasn’t comfortable. But it was instructive.
The differences between us weren’t the story. What those differences revealed about me was.
Seychelles: Beauty and the Discipline of Watching
The Seychelles could not have been more visually perfect.
Turquoise water. Granite boulders. Small boats hopping between islands, including Curieuse Island: raw, undeveloped, and breathtaking. Days stretched long. Conversations stretched thin.
One habit of Glenn’s stayed with me.
No matter what else was happening, he insisted on seeing the sunrise and the sunset. Properly. Not casually. Intentionally. Crossing the island if necessary. Timing the day around those fleeting moments.
At first, I thought it was ridiculous. The sun rises and sets every day.
Then I started watching. Really watching.
That brief pause, when strangers fall silent together as the sun touches the water, was something I’d been missing. Presence, practiced deliberately.
That ritual followed me home.
Alone Again: Integration
After the Seychelles, we went our separate ways. I returned to South Africa, then on to Cape Town.
In Johannesburg, I stayed at The Residence, where dinner felt like stepping into another century. A live pianist. Impeccable service. A multi-course meal with wine that was extraordinary in quality and shockingly accessible in price.
It wasn’t indulgent. It was civilizing.
In Cape Town, I walked for hours. I took the cable car up Table Mountain and stood there looking out over the city, the ocean, and the edge of a continent.
I discovered something else that trip, something I’ve carried forward ever since.
I started offering to take photos for strangers. Couples struggling with selfies. Families trying to capture a moment. I’d take the shot on my phone, send it to them, and move on.
It cost me nothing. It gave them something.
And it reminded me that travel isn’t just about what you see — it’s about how you show up for others while you’re seeing it.
What Changed When I Came Home
This trip changed me. Explicitly.
Traveling with Glenn forced me to see how certain behaviors land when magnified. It made me more aware of when I interrupt. When I correct. When I assert unnecessarily.
I listened more. I softened my edges. I paid attention to how my presence affects the person across from me, especially my wife.
I came home a better husband.
Not because Glenn intended to teach me anything, but because contrast is a powerful instructor.
Why I’ll Keep Saying Yes
Travel isn’t always easy. It shouldn’t be.
It challenges you. It exposes blind spots. It demands attention. And sometimes, it asks you to sit with discomfort long enough to learn from it.
Despite the risks, and maybe because of them, I’m already looking forward to the next one. Check out all the photos from this trip in this Facebook post.
Another place. Another companion. Another lesson I didn’t know I needed. Here is the last photo I took from the trip. It is safe to say sunsets mean a bit more to me now.
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.
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)
Why the Azores
The Goal We Didn’t Expect
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.
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.
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.
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.)
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.
“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 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.”
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.”
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.
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.
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.
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.
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.
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.