My Travels With Strange Men

My Travels With Strange Men

Start Here: What Are the Strange Man Trips?

The Strange Man Trips began almost by accident in November 2021, when I invited a man I knew mostly from the internet to share a cabin with me on a cruise. That could have been awkward, stupid, or both. Instead, it became one of the most unexpectedly meaningful travel experiences of my life.

The idea is simple: say yes to traveling with men outside my normal orbit, or at least outside my normal comfort zone, and see what happens when two people are dropped into the pressure cooker of shared meals, shared logistics, long walks, wrong turns, weird conversations, and too much time together. Some of these men were near-strangers. Some were friends, vendors, neighbors, or people I knew in one context but had never really tested in another. The common thread is that travel reveals people quickly, including me.

These stories are not really travel guides, although there is plenty of travel in them. They are stories about friendship, risk, discomfort, status, freedom, business, marriage, aging, self-awareness, and the strange magic that can happen when men spend real time together without the usual scripts. Sometimes the destination is the point. Usually, the person sitting across from me turns out to be the point.

I will keep adding new Strange Man stories as they are written. To get notified when the next installment is published, sign up for the SCOTTeVEST / Pocket Points newsletter at the bottom of this page.

Read the Series

  • Episode 1: Scott Eddy — Virgin Voyages, Caribbean, November 2021
    The trip that accidentally started everything. I invited Scott Eddy, a travel personality I knew mainly through Facebook, to share a cabin on an early Virgin Voyages cruise. What could have been a bizarre mistake became a surprisingly honest friendship accelerant, complete with pandemic-era cruise weirdness, a dolphin-excursion mutiny, and the realization that traveling with a near-stranger can reveal a lot about both people very quickly.
  • Episode 2: Glenn Shapiro — Africa and the Seychelles, Early 2022
    A safari, the Seychelles, and unfinished emotional business with Africa turned into a deeper lesson in contrast. Glenn’s intensity, confidence, and insistence on sunrise and sunset rituals forced me to slow down, pay attention, and notice some of my own patterns more clearly. The scenery was spectacular, but the real story was what the friction taught me.
  • Episode 3: Dirk Dunlap — The Azores, June 2022
    This was the first high-stakes Strange Man trip because Dirk was not just a companion; he was an important SCOTTeVEST vendor. In the Azores, we hiked ourselves into questionable situations, made a public weight-loss bet, talked about values, family, faith, business, and life, and turned a vendor relationship into a genuine partnership. This is where the experiment started to feel real.
  • Episode 4: Andrew Peterson / Thomas Hawk — Arizona to Palm Springs, November 2022
    Andrew was not a stranger, but he was strange in the best and most important way. Calm where I am fast, disciplined where I am impulsive, and brilliant behind a camera, he had already become one of the people who helps keep my life in balance. Our neon-chasing road trip became a story about photography, friendship, money, trust, and the rare person who can document your life while also helping you make better decisions.
  • Episode 5: Joe Schultz — Cabo San Lucas, November 16–20, 2023
    A trip with my massage therapist sounds like the setup to a joke, which is partly why it worked. Cabo became a study in status, freedom, happiness, and self-consciousness, wrapped in beach walks, scuba disappointment, rooftop four-hand massages, and Joe’s unforgettable rave-floor confidence. Joe had chosen meaning over the obvious version of success, and for a few days in Cabo, I got to see how powerful that choice can be.
  • Episode 6: Laird Erman — California, Mid-December 2023
    What started as a practical Ferrari pickup trip turned into a roaming California adventure with Laird: Santa Monica, Beverly Hills, canyon roads, Santa Barbara, boat life, Cars and Coffee, and a very Laird-style booze cruise. The contrast was the lesson. I was traveling through California in a dream Ferrari; Laird was living with a fraction of the structure and resources, yet somehow seemed rich in ease, stories, friendships, and the ability to enjoy almost anything.
  • Episode 7: Andrew Wood — Patagonia, Argentina & Chile, February 2024
    What happens when the “strange man” gets to tell his side first? Scott joined Andrew Wood, a British golf publisher and world traveler he had never met in person, for a two-week Patagonia expedition involving shared hotel rooms, endless dirt-road drives, glacier hikes, competitive nonsense, family conversations, and enough close quarters to test whether the Strange Men concept still worked at the edge of the world. This time, Andrew tells the story — and Scott reluctantly lets him.

MY TRAVELS WITH STRANGE MEN - Episode 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 - Episode Two: 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.

So when Glenn mentioned Africa and the Seychelles, I didn’t hesitate.

“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 - Episode Three: 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.


MY TRAVELS WITH STRANGE MEN - Episode Four: The Strange Man Who Already Knew Me

The early Strange Man trips were simple. Entertaining, but simple. Read about them all here.

I picked men I barely knew (sometimes didn’t know at all) and hit the road. The magic was in the unfamiliarity. The risk. The awkward question of whether we’d still like each other by the end.

That was the formula.

Then came Andrew.

It was November 2022, and the goal was to chase neon signs from Arizona into Palm Springs. By this time Andrew Peterson, known publicly as the photographer Thomas Hawk, was not a stranger.

He already knew me.

He knew how I think.

How I overthink.

How I accelerate.

How I chase.

And yet he remains one of the strangest men in my life.

Not strange because he’s unfamiliar. Strange because he’s wired so differently.

Steady. Disciplined. Calm. Highly intelligent. No drama.

Where I bring rocket fuel, Andrew brings gravity.

If Laura is the anchor in my personal life, Andrew is the anchor in my financial life. Laura trusted him before I did. And if Laura trusts you, that’s about as serious an endorsement as exists in my world.

Andrew manages our investments. I don’t micromanage him. I don’t second-guess him. His approach is conservative and methodical, which is fortunate, because when I pitch something risky, he refuses. Calmly.

He has talked me off more than one ledge. Not by telling me to slow down, but by presenting logic so clearly that I can’t argue with it.

That kind of friend is rare.

This particular trip was entirely his idea. Andrew is on a mission to photograph America. Every state, every major city, every fading neon sign before it disappears. His Flickr archive is staggering: hundreds of thousands of edited images, tens of thousands already published, thousands more queued. He preserves what the rest of us drive past. 

You can see thousands of the photos he’s taken of me here:
I contributed one thing to our trip: a Mustang convertible.



So we drove, top down, desert wind in our faces, chasing GPS pins like we were on a preservation mission.

Pull up.

Reposition the car.

He runs across the street.

“Stay there.” Click.

“Now get out.” Click.

Move the car. 

Drone up. Drone down.

Next stop.

It felt like a race against time.

And I never feel ridiculous in those moments. I feel iconic.



When we arrived in Palm Springs, it was just one more destination on his carefully researched route. We stayed in an Art Deco hotel. Photographed Sinatra’s grave. Elvis’s honeymoon house. Ate well. Debated politics. He leans libertarian, I lean heavily Democratic, and somehow we maintained mutual respect.

As we enjoyed the desert, not once did I think, “I could live here.”

But I did think it had a certain energy.

A vibe.

A design language.

A desert confidence.

I didn’t know it then, but that stop would become a quiet bookmark in my life. A place I would return to, this time not for neon, but for permanence.

Andrew has been behind many of my biggest decisions, including the Ferrari and, later, the Palm Desert house. He never pushes. He lays out the math, the risk, the options. And occasionally he says something simple:

“You can afford it. It will make you happy.”

That sentence carries more weight than it should.

I’ve built a company. Taken risks. Made bold decisions. And yet hearing someone I deeply respect calmly say, “You deserve this,” matters.

He’s one of the very few people who reminds me to pause and appreciate what Laura and I have built. To enjoy instead of chase.

Somewhere between that first random photo he took of me years ago and this neon safari, the photographer became something much more.



Andrew has photographed more of my life than anyone outside my own phone. Cars. Homes. Trips. Laura. Random Tuesdays. Thousands already public. Thousands more coming.

If I disappear tomorrow, there will be a visual archive of who I was.

Andrew created that.

On this trip, I finally convinced him to embrace drone photography, something I had been nudging him toward for years. He resisted. Then he flew it. Then he loved it. Today aerial perspective is part of his creative language. Take a look at him fly the drone once he got the hang of it here.



It made me oddly happy to open that door for him, just as he has opened doors for me.

The early Strange Men tested chemistry with strangers.

This one was different.

This was about choosing to travel with someone who already knows your flaws, your excesses, your ambition, and still shows up.

Andrew may not be a stranger.

But he is rare.

A friendship that holds both balance sheet and brotherhood.

Americana and asset allocation. Mustang convertibles and measured restraint.

He preserves America. He preserves balance sheets. And he has preserved a great deal of my life.

And like Laura, he keeps me grounded without ever trying to hold me down.

 


MY TRAVELS WITH STRANGE MEN - Episode Five: Cabo With Joe Schultz

Continuing the Strange Men series, I barely had time to come up for air after saying goodbye to Thomas Hawk in Los Angeles before I did something that, even by my standards, qualified as a slightly questionable idea.

I spent one night in Los Angeles, then flew straight to Cabo San Lucas on November 16, 2023, with my massage therapist, Joe Schultz.

Yes, really.

Joe had heard all about these trips because every time I got a massage, I would tell him the stories. Somewhere along the way, while I was planning Cabo, I asked if he wanted to come. He said yes. And just like that, the next Strange Men trip was born.

This one bent my original rule a bit.

The whole Strange Men concept started with the idea of traveling with men I barely knew well, often men with whom I had not even really broken bread before. It was never a rigid legal code, but more a loose framework with one important understanding: if things went sideways, either of us could bail out and move on separately after making a good-faith effort to see whether the chemistry worked. 

With Joe, there was a little more trust and a little more risk. We may have had lunch before, but not much more than that. And unlike some of the other trips, we were sharing a hotel room. My room, no less. Fortunately, I had a pretty strong hunch it would be fine.

It was more than fine. It was fantastic.

Joe was, in his own way, one of the strangest men of all, which is exactly what made him interesting. He came from a background that was oddly familiar to mine in some ways: Jewish, educated, once on a more conventional path, originally in finance. But then he did something few people have the courage to do. He walked away from that world and decided to dedicate himself to becoming the best massage therapist he could possibly be. He had spent months living in India, told stories that hinted at a much more thoughtful and unconventional life than most people ever bother building, and carried himself like someone who had chosen meaning over status and actually meant it.

That intrigued me.

I was not lonely. I travel alone all the time and genuinely enjoy it. But after the success of the earlier Strange Men adventures, I figured: why not keep going? Why not continue the experiment? Joe was available, curious, easy to talk to, and seemed like someone from whom I might actually learn something.

So off we went to Cabo. Check out our first meetup on night one here.

We stayed at ME Cabo, a spectacular, not-so-inexpensive hotel in Cabo San Lucas, right on Medano Beach. Great vibe, great weather, great food, great music, beautiful sunsets, and exactly the sort of place that makes you feel like your life choices, at least for a few days, have been unusually solid. At some point I also had to deal with some bizarre room-charge dispute where someone had billed a bunch of things to our room that were not ours, but even that somehow failed to ruin the mood.

The trip ran through November 20, the day before my birthday, and for a relatively short trip, it packed in a lot.


We did all the touristy nonsense you are supposed to do in Cabo, and some you probably are not. We had our feet cleaned by minnows. We went into one of those pressurized floating air-tank experiences that felt vaguely like something between wellness culture and a science experiment. We ate extremely well. We spent a lot of time in the hot tub. We took photographs, reviewed them, talked endlessly, and walked the beach for hours.

Those walks were probably the real heart of the trip.

Joe and I had the kind of conversations that happen when two men from very different paths discover they are asking similar questions. We talked about relationships, especially my relationship with Laura and why it has worked so well. We talked about success, and more specifically the uncomfortable fact that I was raised in a world where money and status carried enormous weight, while Joe had quite consciously stepped off that track. He had chosen a life that was not nearly as financially rewarding, but was deeply aligned with what actually made him happy. He wanted to help people feel better. He wanted to get really good at something human and intimate and useful. He built a life around that.

And somewhere in those conversations, I found myself admitting something I probably already knew: that while financial success had driven me for much of my life, it had also been overrated in ways I had not fully appreciated until I met men like Joe. People who were not trying to win the obvious game. People who had, in their own way, already won a better one.

That was a meaningful part of the trip.

There was also a less meaningful part involving scuba diving.

Technically, yes, we went scuba diving together. In reality, it involved a two-and-a-half-hour ride each way for what turned out to be a fairly average scuba experience in the middle. Joe was the one pushing for it. We made the best of it. We had fun. But if I’m being honest, it was mostly a wasted day and not the crown jewel of the adventure. Cabo itself, the walks, the conversations, the sillier tourist experiences, and the downtime together were much more memorable.

One especially surreal detail of the trip deserves its own mention. Right next to ME Cabo was an outdoor massage place on the roof, right on the beach, with what felt like about fifty massage beds lined up side by side in the open air. That may be a slight exaggeration, but only slight. Check out my fist impressions here. You could lie there listening to the ocean while two women gave you a four-hand massage simultaneously, all for a sum of money so reasonable it felt almost absurd given how good it was.

Joe and I turned it into something of a ritual, going almost daily and sometimes twice in a single day. I got a real kick out of the fact that Joe, an actual massage therapist and someone who had devoted a meaningful part of his life to mastering that craft, seemed to enjoy receiving massages every bit as much as giving them. And honestly, I couldn’t blame him. A cheap four-hand massage on a rooftop over the beach in Cabo is about as close to euphoric as a person has any right to expect.

And then there was the rave.

This may have been the highlight.

We ended up at a very hip, youth-oriented rave-style party, the kind of place where everyone is curated, deliberate, and extremely aware of how they appear. Before the party even properly got going, before there was really even much of a crowd, Joe went out onto the dance floor alone and started breakdancing.

Or at least what can most generously be described as breakdancing.

Imagine a Saturday Night Live skit. Imagine Jim Belushi trying to impress a room full of attractive, far younger people. Imagine someone moving with complete commitment and absolutely no concern for whether he looked cool, current, or sane. That was Joe. He looked ridiculous. It was glorious.

The bouncer, perhaps sensing that this was not exactly the aesthetic the venue was hoping to cultivate, came over and asked him to stop.

I was delighted.

At first I may have felt a flicker of secondhand embarrassment for him, but that evaporated the moment I realized he had none for himself. And once you see that someone is truly free of self-consciousness, it becomes almost impossible not to admire them. Joe was not performing coolness. He was not trying to fit in. He was not calibrating. He was simply having fun, fully, absurdly, unapologetically.

That stayed with me.

It also captured something essential about the Strange Men series as a whole. These trips were never really about the destination. They were about proximity to people outside my usual orbit. Men with different histories, different philosophies, different ways of moving through the world. Men who, for one reason or another, seemed worth saying yes to.

Joe was absolutely one of those men.


As for SCOTTeVEST, yes, we both wore it, though this was not exactly a trip where the clothing was the star. Beach destinations tend to require fewer pockets than urban adventures. Still, useful summer travel clothing proved useful summer travel clothing. Joe wore SCOTTeVEST pieces including the cabana shirt, performance tee, jogger pants, and shorts. I wore my usual quarter-zip with a SCOTTeVEST logo, and even in a place like Cabo, the utility mattered. Sunscreen, a credit card, a hotel key card, and a phone are the little things that always need a home when you are trying not to carry a bag around all day.

But this was not a SCOTTeVEST commercial.

It was a friendship story. Or at least the story of how an unlikely friendship briefly took shape in a beautiful place, under ridiculous circumstances, with surprisingly meaningful results.

Joe and I did become real friends afterward, and while life eventually complicated that as life tends to do, that is not really the point of this story. The point is that for four days in Cabo, two men from very different backgrounds, with very different definitions of success, managed to meet in the middle and enjoy the hell out of each other’s company.

That is not nothing.

If anything, it is the whole point.

Some men chase status. Some men chase meaning. Some get lucky enough to realize, eventually, that meaning was the better game all along.

And sometimes, if you are open to it, you can learn that from your massage therapist while watching him get politely shut down for breakdancing at a rave in Cabo.

Honestly, that feels like money well spent.



MY TRAVELS WITH STRANGE MEN - Episode Six: California with Laird Erman

After my trip with Joseph Schultz, I went to Palm Springs with Laura and the poodles for a couple of weeks, then came home to Sun Valley in mid-December with a gap in my schedule, lousy skiing, and a problem I was more than happy to solve: my Ferrari was waiting for me in Los Angeles.

The Ferrari

That car deserves a brief explanation.

The Ferrari did not fall into my lap, and it sure as hell did not show up because I woke up one day and decided I should be the kind of person who drives one. That car is the byproduct of more than twenty years of building a business, taking risks, getting things wrong, getting a few things very right, and surviving enough ups and downs to make the eventual reward feel both wildly indulgent and completely earned. For most of my life, a Ferrari was not a realistic goal. It was a poster-on-the-wall kind of fantasy, the sort of thing you dream about when you are younger and assume belongs to some other category of human. So yes, I love the thing in a way that may not be entirely rational. But to me it is not just an expensive car. It is a rolling reminder that a lot of grinding, hustling, stressing, risking, and occasionally getting my teeth kicked in somehow led somewhere.


That is part of why this trip mattered. On one hand, I had this absurdly beautiful machine that represented one version of success, mine. On the other hand, I was about to spend time with Laird Erman, who represented a completely different version of a successful life. A life where success was less tied to money, had far less structure, and in some ways, a lot more freedom. That contrast was not obvious to me when I got on the plane, but by the end of the trip it became the whole point.

My Ferrari GTC4Lusso is not just a car to me. It is, in many ways, the physical manifestation of every adolescent fantasy I ever had about making it in life. It is beautiful, excessive, impractical, ridiculously capable, and still manages to make me smile like an idiot every time I see it. I know how that sounds, and I’m fine with it. Some people buy watches, some buy boats, some buy therapy. Apparently, I bought a V12 Ferrari.

I had left it in Los Angeles after some work in Palm Springs, and I needed to go deal with it. The original plan was simple enough: fly to L.A., pick up the Ferrari, enjoy a few drives, drop it at the Ferrari dealer for warranty work, spend six nights in California, and come home. I had one hotel reservation and a rough plan to play some pickleball, stay somewhere nice, and see where the week took me. That was all.

Gallivanting

As it turned out, that was plenty.

One of the great pleasures in my life is gallivanting, and I use that word deliberately. I like motion. I like new surroundings. I like hotels, roads, restaurants, strangers, scenery, and the little improvisations that happen when you stop overplanning your life and let a trip unfold one day at a time. This was that kind of trip from the very beginning. I landed in California with my passport, no meaningful agenda, and exactly the right amount of structure: enough to get started, not enough to get trapped.


The first few days were a blur of movement and indulgence. I drove the Ferrari on canyon roads around Los Angeles and Malibu, the kind of roads the car seems to have been built for. I walked along the coast at Point Dume. I played pickleball in Calabasas. I packed light, knowing I could rely on a few SCOTTeVEST items in any of these situations. The pockets proved useful whether I was on the road, staying active, or roaming around town.

I checked the weather back in Sun Valley, realized I was in no hurry to return, and started to think that maybe this “short” trip might become something else. It already had that feeling.

Enter Laird

And then I called Laird Erman.

Laird lived across the street from me in Ketchum. I had known him for years, but knowing a man across the street and traveling with him are two entirely different things. We had spent enough time together over the years for me to know he was unusual in the best possible way, but not enough for me to know what he’d be like as a real companion on the road.

What I knew was this: he had style without trying too hard, manners without stiffness, and an ease about him that made him fit in almost anywhere. You could put Laird on a fancy patio in Montecito, on a boat in Santa Barbara Harbor, in a dive bar, or on a street corner holding a paper cup, and somehow none of it would look out of place. He is weathered, sunburned, amused by life, and has the sort of face that suggests he has either lived very well or very recklessly, possibly both. He is not conventionally handsome, but he is magnetic. He looks a bit like the world’s most interesting man after budget cuts and better stories.


I invited him to join me at Shutters on the Beach in Santa Monica, where I had booked a fancy room for the night because sometimes subtlety is overrated. He came down, and within about ten minutes I realized the trip had just changed for the better.

There was no warming up period. No awkwardness. No “let’s see how this goes.” It simply went.

We laughed in the hot tub, took ridiculous pictures, and slipped almost immediately into the kind of rhythm that usually takes years to build with someone. That is rarer than people admit. Most people are enjoyable in doses. Travel tests them. It reveals pettiness, rigidity, weird habits, passive aggression, boredom thresholds, control issues, and a hundred other things that are easy to hide in normal life. Travel with Laird did the opposite. The more time we spent together, the easier he became.

The Ferrari Tour

That night we had dinner at Michael Mina’s Orla, which was probably the best meal of the trip, though to be fair the laughter may have improved the seasoning. From there we got into the Ferrari and did what can best be described as a middle-aged, highly polished, entirely unserious Christmas tour of Beverly Hills.

It was glorious.

We drove from grand hotel to grand hotel, valeting the Ferrari, admiring the decorations, making friends, and generally behaving like two men who had temporarily decided to stop pretending to be sensible adults. We pulled into the Beverly Hills Hotel and the Polo Lounge as though we belonged there, and thanks to Laird, somehow we did. That was one of his gifts. He could walk into beautiful places without shrinking, straining, or posturing. He didn’t look impressed in the needy way that some people do around luxury. He just enjoyed it. Then he enjoyed the next thing too.

What Laird Appreciates

That became one of the defining lessons of the trip.

Some people only know how to appreciate expensive experiences. Laird appreciated everything. A gorgeous hotel lobby dressed for Christmas. A fast car on a canyon road. A hike. A harbor. A cheap bite. A strange dog. A sunset. A conversation with someone he had just met thirty seconds earlier. He had none of that brittle quality some people have, where enjoyment depends on whether the setting is fancy enough to validate them. He genuinely liked life. Not just the deluxe version. The whole menu.


Santa Barbara

The next phase of the trip moved north to Santa Barbara, where Laird lived on a boat.

That too deserves a brief explanation.

Years earlier, after getting hit hard during the real estate collapse, Laird took a turn in life that most people would consider either insane or inspiring. Instead of clinging to a more conventional version of success, he bought a boat on a credit card, lived on it in Santa Barbara, and built a life around mobility, skiing, friendship, and a kind of cheerful improvisation. On paper, there are probably many reasons his life should not have looked appealing. In person, it looked pretty damn good.

His boat was not some gaudy billionaire toy. It was simply his place. His base. His chosen world. And it suited him perfectly.

The time in Santa Barbara was some of the most enjoyable of the whole trip. We wandered the harbor. We drove. We hiked. We went to Cars and Coffee. We spent time in Montecito. We had one of those easy, low-friction runs of days where everything seems to click and no one has to work too hard to make it happen. I do not remember one dramatic conversation or one particular turning point where I suddenly decided to trust him. The truth is simpler than that. He was just easy to trust. Easy to travel with. Easy to be around.

The Booze Cruise

Then he threw what he called a booze cruise.

This was classic Laird. Out of thin air, he assembled an eclectic group of people on the boat in Santa Barbara Harbor for an evening cruise that somehow felt both casual and magical. There were drinks, stories, laughter, sunset photos, and the sort of social ease that cannot be faked. I remember standing there thinking that this was exactly the kind of thing I would have loved at twenty, at forty, and now. It had no business being that effortless, and yet it was.


That evening captured something important about Laird. He knows how to create life without making a production out of it. He does not need a giant plan, a huge budget, or a branded experience. He just needs a decent idea, some willingness, and the next few hours. He makes people feel welcome. He makes things happen. He has fun. It sounds simple because it is simple. Most people are just too guarded, tired, or image-conscious to do it.

The Contrast

That was the deeper contrast between us, and the deeper gift of the trip.

I was rolling through California in my dream Ferrari, staying in beautiful hotels, eating very well, and generally sampling the high-end version of freedom. Laird was living on a boat, watching his expenses, and operating with a fraction of my resources. And yet, being around him, I could not escape the feeling that he had access to a kind of wealth that many richer people never reach.

He was, and is, an extraordinarily wealthy man with no money.

I mean that exactly the way it sounds.

He is wealthy in adaptability. Wealthy in ease. Wealthy in humor. Wealthy in confidence. Wealthy in stories, friendships, experiences, and lack of pretense. He has figured out how to enjoy a day from almost any starting point, and that is not a small talent. In some ways it may be the whole game.

Why It Worked

I have now traveled with Laird many times since then, and I can say without hesitation that he is one of my favorite companions in the world. He is appreciative, flexible, socially graceful, and game for nearly anything. Hiking, hotels, long drives, good dinners, odd detours, random people, beautiful scenery, stupid jokes, whatever. He enjoys what he is doing while he is doing it, which sounds obvious until you realize how many people do not.

That California trip began because I had to go deal with the Ferrari. It became one of the highlights of my Strange Man travels because it reminded me that while money can buy access to wonderful things, it cannot guarantee the ability to enjoy them. Laird has that ability in abundance.

I went to California because of a car. I came back with something much better: a clearer understanding of friendship, freedom, and the fact that a rich life and a rich man are not always the same thing.


Scott and Andrew in Patagonia

MY TRAVELS WITH STRANGE MEN - Episode Seven: The Other Strange Man Tells His Side

Scott's Introduction

Before I write my own version of Patagonia with Andrew Wood, I thought it would be more interesting — and probably more dangerous — to let Andrew go first. This is his version of the trip: two men who barely knew each other, heading to the end of the world, sharing rooms, driving endless roads, hiking, arguing over music, dodging llama-like creatures, and talking about everything you are supposedly not supposed to discuss with a near-stranger. I have resisted the urge to correct every exaggeration, insult, and alleged fact. I have made only light edits for clarity, flow, and public readability, while preserving Andrew’s voice and the spirit of his piece. My version of the same trip, through my eyes, will follow next month.

Andrew Wood's Version

I first met Scott Jordan through his company SCOTTeVEST when I saw an ad on Facebook and bought a vest for my wife’s birthday. I was immediately impressed by the product's quality and versatility and bought my own SCOTTeVEST vest. It really is the perfect piece of kit for a frequent traveler like me.

Sometime later, after seeing more ads for the products, I decided to contact Scott and tell him that I thought his product would be ideal for the golf business, where I have a large reach. We got into an email conversation, and he sent me some product. I wrote some blog posts about my travels in Europe last year, and we started a dialogue. I read his book Pocket Man, which spurred me to write an article about him as a unique entrepreneur for my blog, www.LifeWellLived.expert.

Strange Man Trip

Finally, after going back and forth by email several times sharing ideas, Scott said, “You know, we ought to go on a trip together.”

I said, “Well, I’m going on a trip to Patagonia two weeks from now if you want to come.”

At first, I don’t think he took me seriously, but I assured him I was serious. I was going and had already put together a solid itinerary with a travel company in case he wanted to tag along. Scott had never heard of Patagonia, which, for the record, is a region located at the southern end of South America. It is split between Argentina and Chile and is one of the most remote and unexplored areas in the world.

Scott called the trip “The Strange Man Trip.” I was sure he must be referring to himself. Apparently, this was not the first trip he had been on under these circumstances, and so it became “Strange Man Trip,” version four.

Most people would probably think that two 60-year-old heterosexual guys, who had never met, from opposite ends of the country and very different backgrounds, deciding to go together on a $10,000, two-week trip to the end of the earth and share a room might indeed be quite strange. The fact that neither of us found this situation strange at all should tell you something.

First Meeting in Buenos Aires

And so, after a flurry of emails, texts, and Zoom calls because Scott is a serious over-planner, we met for the first time in Buenos Aires. Buenos Aires was not without some incidents, but I’ll let him fill in the details on that.

Scott was about my height, although it was later proven that I was actually a full inch taller. He was about my weight, although he had just lost a significant amount, beating me by a few pounds on that score. Scott wore a straw hat, which looked good on him; I prefer golf visors. We were both, of course, dressed head to toe in SCOTTeVEST clothing, and I really loved the cargo pants, which I was wearing for the first time. Comfortable, stylish, and, most of all, wonderfully practical for travel.

Amazingly, I found Scott was even more outgoing than I am, which none of my friends believe. Scott says “Hello” to everyone he passes, which works quite well on a lonely hiking trail and not nearly so well on a crowded sidewalk in a city where no one speaks English. During our trip, he stalked at least two tourists wearing SCOTTeVEST clothing. One of them, a New Yorker recognizing him from Shark Tank, was eager to get a picture with him and chat for ages — obviously the first B-grade celebrity he had ever met in person. The other man talked to Scott in nervous chatter, continuing to walk briskly while anxiously looking around for a policeman. “Who is this guy?”

After a hot day in Buenos Aires, marching around town at my usual fast pace, we saw pretty much everything there was to see in a day. At night, we had a wonderful steak meal in the upscale Palermo district and got up early the next morning to fly down to El Calafate, where our real trip to Patagonia would kick off.

Scott and Andrew meeting in Buenos Aires Buenos Aires street scene in La Boca

Off to Patagonia

When we got to El Calafate, we rented a car and headed off into the desolate yet beautiful landscape toward the town of El Chaltén. The road up there was filled with beautiful lakes, snowcapped mountains, rugged terrain, and llamas — or something that looked like llamas — everywhere. The wind was howling, but I stopped several times to take photographs of the stunning terrain, much to Scott’s chagrin.

Patagonia road and landscape

Arrive Alive

As I said, Scott is a meticulous planner. He downloads Google Maps, then Apple Maps, takes a paper map from the rental counter, gets hand-drawn directions from the front desk at each hotel, and searches out the concierge to ask for additional options. I prefer to wing it, go with the flow, and head in the general direction of our next stop. After all, there was only one frigging road. Head out of town and take the first left turn. It wasn’t exactly rocket science, just a 200-mile journey straight down Hwy 40 with not a single option presented left or right to go wrong.

I did almost all the driving. This was the call I made early in the trip when, two or three times, I slammed the brakes on from high speed as Scott yelled, “What the fuck?” I pointed several times to a herd of llamas in the middle of the road a hundred yards ahead. The fact that Scott couldn’t see them even after I pointed them out was an early indicator of who should be driving. While I did most of the trip at double the speed limit, Scott was always eager for me to go faster. However, with giant potholes every few yards and llamas crossing the road from every angle, I felt that was fast enough. Half the roads were paved, half were not, and when we dropped off the car, the rental guy was surprised to learn we hadn’t had a single blowout or puncture, thank goodness.

Scott hogged the radio with a bunch of Laura’s playlists, which didn’t seem to make it out of the 70s. Now, to be fair, there’s a lot of good music from the 60s and 70s, but there was a lot of good music from the 80s and 90s, too — not that we ever heard any of it.

First Night Together

Our first night passed without incident despite my snoring and despite what Laura says — or, to put it correctly, what Scott says Laura says.

Laura Dear:

Scott waxed lyrical about what an amazing person you are the entire trip: how the business is built around you, how you keep yourself in great shape, how you are Mensa smart, and much more. All this seems irrefutable. However, Scott also tells me that you tell him he doesn’t snore.

This tells me one of four things:

A: Either you guys don’t sleep in the same building together.

B: Your love for him is so great you’re willing to lie to his face about his snoring problem, which after all is common in just about every middle-aged man.

C: You’re overdue for an appointment with your ear specialist. Since we haven’t met, I obviously don’t want to be rude, but trust me: he SNORES!

D: He is lying about you saying he doesn’t snore?

Anyway, I leave it with you. Just know I have iPhone footage of him THUNDERING out the ZZZ’s which, unlike his footage of me (which he posted), I thought inappropriate to post on Facebook without his permission.

Best,
AW

First Magical Hike

Our first hike was a great success. We did the Laguna Torre hike, a fourteen-mile hike — seven miles out, seven miles back — with absolutely stunning scenery. It was a relatively benign hike to a glacier lake with some of the best pictures I’ve ever taken in my life. When we got back to town, I was ready to do more, but instead Scott took me for a beer, never a hard sell for an Englishman, then went in search of a massage. Meanwhile, I did another smaller hike to get my step count a little higher. In short, I wore him out.

Laguna Torre hike in Patagonia

Bragging Rights

The next day, we embarked on a much more strenuous hike, and halfway up the final peak I called it a day and went back to the car for a nap, thus giving Scott bragging rights for the rest of the trip for making it to the top. This even though on every other hike we made, he lagged 300 to 400 yards behind me. Scott, who for the last two decades or more has lived in Sun Valley, Idaho, was like a mountain goat going uphill. Me, having lived in Florida for more than 20 years, was not so good at going uphill. However, on the flat, I took off like the hare while Scott more resembled a wounded snail than a tortoise. I was consistently several hundred yards ahead; however, many people have told me I have a good-looking backside. This is a view Scott got to enjoy for most of the trip. Just saying!

Patagonia mountain hike

The hotel was a decent four-star but nothing special, but both nights we had excellent meals: one night in a little log cabin reminiscent of a Swiss chalet, another in a fine dining establishment you would not expect to find in a mountain village as small as this was. We ate and drank like Vikings the entire trip and, despite multiple 30,000-step days, did not lose an ounce.

Dinner during the Patagonia trip

Spot the Gas Station

The next day, the priority was to find a gas station since they are few and far between in Patagonia. We were told there was a gas station on the way out of town just over the bridge, and so we drove out of town, over the bridge, about three or four miles before we decided we must have missed it. We turned around and drove back into town, missing it again. We came out of town over the bridge again and there on the left was something that loosely resembled an abandoned boxcar. Sure enough, cut out from the middle of the boxcar was a single petrol pump, and we filled up.

Remote Patagonia gas station

El Calafate

El Calafate was a vibrant town with plenty of shops and restaurants located on a large bay. Our hotel had a fine view, and we took it easy that night and dined in the hotel after taking a walk along the seafront to get our step count up. The next day, we got up early and embarked on a boat trip to see the glaciers. The water was a sparkling blue in some places and a milky blue in others, but very different from anywhere else I’d ever seen. The glaciers were extremely impressive, and again we got a lot of brilliant photographs.

Glacier and blue water in Patagonia

Chile

The next day, we gassed up and set out on another long journey, this time crossing into Chile. Once again, the scenery was rugged, desolate, and breathtaking all at once. Getting into Chile was a pain in the ass. They had a small wooden hut where you had to line up and show your passport, then go to a different window to show you had permission to take the car out of Argentina, then go to a third window to show your bags. It was a complete joke and wasted an hour of everybody’s time.

Long Drive Conversation

What did Scott and I talk about on these long, desolate journeys? We talked about politics, movies, cars, music, business, marketing, Israel, Laura, poodles, watches, technology, the war in Ukraine, and, inevitably, family. We talked generally about cable news, national politics, and Scott’s complicated relationship with his father and sisters. I have my own family complications, so it was not exactly unfamiliar territory. As I told Scott, you can choose your friends, but you can’t choose your family.

Torres del Paine

The next hotel was a rustic beauty at the foot of a giant mountain in the Glacier National Park. It was our base point for two magnificent days of hiking and a very memorable drive to Grey Lake. The scenery just seemed to keep getting better, and we really lucked out with the weather. For several days, the forecast was for 50 to 80% rain. We literally never saw anything more than one ten-minute shower on the way back from our first hike here. This was a pleasant surprise.

On the first day, we attempted to scale the most difficult trail, but after hiking for only about thirty minutes, the fog rolled in, the wind started blowing, and it briefly snowed. Fortunately, Scott threw in the white flag before I did, so I could blame him for that one. Instead, we went to lower ground and had a beautiful hike along a pristine lake that shimmered a milky blue. That night at dinner, we saw a puma walk past our window — pretty magnificent. The next day, Scott was determined to do the hard hike. I’d already decided I was going to push further down the lake trail. I have no problem walking, but you have to remember I live in Florida. Anything above 100 feet is higher than any point in Florida. Walking straight uphill is not for me. I prefer the mountain passes in Switzerland, where they go every bit as high and higher, but they zigzag up the mountain. Here, they just kind of went straight up. So I had a good time getting in a 14-mile hike around the lake. Scott went up the mountain again for bragging rights, and we met for dinner.

Puma seen during the trip

That afternoon, we took the car on a 120-kilometer odyssey on dirt roads to Grey Lake, picking up another entire book of amazing photographs of lakes, mountains, and rugged terrain. The food at the hotel was good, and it was served ranch-style, with only three options each night, which at least kept it simple.

Grey Lake landscape

Punta Arenas

Punta Arenas is a city near the tip of Chile’s southernmost region, Patagonia, and was only an overnight stop. Located on the Strait of Magellan, which connects the Atlantic and Pacific oceans, we crossed on a car ferry, which at 58 was a first for Scott. He really must get out more.

Punta Arenas and Strait of Magellan

Another Long Drive

We were up early for another long drive, this one five hours or so to Rio Grande. When we got there, it was a rather nondescript town. It was also Sunday, the wind was howling, and almost nothing was open. Our hotel was a casino hotel, deader than dead. We walked into the huge restaurant; none of the tables were set, and nobody was in there, but it was open. Scott and I sat down to fish and chips before he announced he didn’t want to stay there, and we should just go to the next town. This was another 200 miles, but it was hard to argue with his logic. There seemed little we would do there except hang out in the hotel room. So off we went, although this time I let Scott do a little bit of driving since I’d already driven for five or six hours. He did fine, just so long as I pointed out the llamas.

Competitive Nonsense and Long-Drive Philosophy

I think we both share the same sense of adventure — the same sense that we should be moving and active and doing things most of the time. I think we shared the same philosophy about entrepreneurism and business. In politics, I like to wind people up whether they’re left or right, because even though I’ve lived in America for 40 years as a resident alien, I’m not eligible to vote, and besides, it only encourages them. Still, despite Scott’s protests to the contrary, I do not feel that he really was a libertarian. We also managed to disagree about age, politics, leadership, and just about anything else two opinionated men can debate while crossing Patagonia. I don’t see why politics even comes into it, but of course it did.

Scott makes way more money than I do, but I’ve had way nicer cars than he’s ever owned. He’s an expert skier. I’m an expert in golf, martial arts, and a decent tennis player, which he tells me he is too. It would be nice to go on a racetrack with him, but I think I’ve got him there. Are we competitive? Hell yes. His watch is worth more, but mine is rarer. Does any of this really matter? No, of course not, but then again, there were a lot of five-hour drives on dirt roads at 120 kilometers an hour.

Did I mention Scott has father issues? Of course, by this point in the trip, I knew enough about him to understand that family, identity, and old wounds were not throwaway subjects. They were part of the long drive conversation, along with everything else. Scott can over-plan, overthink, and occasionally overreact — which, naturally, gave me plenty of material — but I suspect he would say the same about me in his own way.

The End of the World

Ushuaia was a vibrant town of 56,000 people set on the Beagle Channel, surrounded by snowcapped mountains. It was pretty windy and cold, but there were plenty of bars, restaurants, and coffee shops. After wandering around for an hour or so, we picked a place for dinner. I, of course, would have looked at four or five places and picked one. Scott instead asked everyone we met what their favorite restaurant in town was, whether they were local or off the cruise ship from Seattle. We settled on a restaurant the concierge had recommended, and I guarantee you she had never bothered to spend her weekly salary to eat there. Still, in this case, both dinner recommendations he came up with proved to be excellent, if pricey.

Ushuaia at the end of the world

This hotel was a proper five-star hotel perched halfway up a mountain overlooking the town with an amazing view and beautiful spa facilities.

Hotel hot tub overlooking the mountains

Enchanting Final Hike

We took one of the most popular hiking trails in the park, the Coastal Trail. It follows the shoreline of the Beagle Channel and offers stunning views of the sea and the snowcapped mountains of Chile as you walk 5 km through an enchanted forest. It was so beautiful it was almost like a movie set, and I half expected a Hobbit to step out from behind a tree at any moment and offer me a cup of tea.

Final hike along the Coastal Trail

Most exciting of all, Scott pointed out a golf course on the way back that turned out to be the southernmost golf course in the world. Since I own a golf magazine, World’s Best Golf Destinations, they were happy to host me for free the following day, which was the perfect end to the trip for me.

Southernmost golf course in the world

Was the Strange Man Trip a Success?

Two guys from completely different continents, with totally different backgrounds, who had never met, spent two weeks together in the same hotel room. What could possibly go wrong? The truth is almost nothing. I would rate it as one of my top five trips of my life, and you’re talking to a guy who’s been on a lot of trips in 75 countries and who knows how many millions of miles. Thanks, Scott, for an amazing time, some great products, and a friendship that I am sure will grow.

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