My Travels With Strange Men

My Travels With Strange Men

Start Here: A Quick Guide to the Strange Men Series

What started as one impulsive trip with a near-stranger became a series of adventures about friendship, risk, discomfort, self-awareness, and the strange magic that happens when men travel together outside their normal roles.

  • Chapter One: Scott Eddy
    A last-minute Virgin Voyages cruise with a man I barely knew turned into the first “Strange Man” trip. It proved that travel can accelerate friendship, honesty, and unexpected personal growth.
  • Part II: Africa with Glenn
    A safari and Seychelles trip became less about scenery and more about friction, contrast, and learning to pay attention. Glenn’s intensity forced me to see my own patterns more clearly.
  • Part III: The Azores with Dirk Dunlap
    This was the first high-stakes Strange Man trip because Dirk was also an important SCOTTeVEST vendor. Hiking, risk, and real conversations turned a business relationship into a true partnership.
  • Part IV: Andrew Peterson / Thomas Hawk
    Andrew wasn’t a stranger, but he was strange in the best way: calm, disciplined, brilliant, and grounding. A neon-chasing road trip revealed how deeply he had already helped preserve both my memories and my balance.
  • Part V: Cabo with Joe Schultz
    A trip with my massage therapist became a surprisingly meaningful study in freedom, status, happiness, and self-consciousness. Joe’s unconventional life and ridiculous rave-floor confidence made this one unforgettable.
  • Part VI: California with Laird Erman
    What began as a Ferrari pickup trip became a roaming California adventure with Laird. His ease, humor, and ability to appreciate both luxury and simplicity offered a very different definition of success.

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.

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 - Part III: The Azores, Dirk Dunlap, and Why This One Was Different

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

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

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

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

The Pandemic Prologue

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

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

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

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



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

Who Dirk Was (And Why He Was Chosen)

Dirk Dunlap wasn’t a stranger.

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

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

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

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

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

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

With Dirk, that wasn’t true.

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

So yes, I was excited.

And yes, I was also slightly nervous.

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

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


Why the Azores

Dirk suggested the Azores.

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

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

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

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

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

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

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

The Goal We Didn’t Expect

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

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

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

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

We both said, almost simultaneously:

“I want to lose 20 pounds.”

So we made a pact.



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

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

What the Azores Felt Like

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

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

Also: we had better cell service than we deserved.

That fact becomes important later.

The Hiking Wasn’t Hiking

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

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

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


The Ravine / Ocean / “We Might Die” Hike

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

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

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

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

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

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

Not dramatic texts. Not “call the authorities.”

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

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

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

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

Somehow, we found our way out.

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

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

Then there was the “tunnel hike.”

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

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

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

“Snakes.”

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

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

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

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

The Relationship Part (The Real Point)

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

He has four children. I have none.

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

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

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



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

And that’s where you learn someone.

Not from what they say they value.

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

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

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

It was fantastic.

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


Dirk jumped in.

I did not.

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

The Unexpected Part: SCOTTeVEST Ideas

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

Not in a boardroom way.

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

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

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

How It Ended

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

We ended it as something else.

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

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

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



People say, “Never do business with friends.”

I get the logic.

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

This trip proved something for me.

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

Episode 3 was epic.

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

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

Accidental friends.


MY TRAVELS WITH STRANGE MEN - Part IV: 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 - Part V: 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 - Part VI: 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.


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