May 2026 - Monthly Update

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.

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.

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.

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.

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.

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.

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.

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.

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.