🔹 CALL TO ACTION! Today we are launching a new series - “Tales From the Road” and we want to hear from you! The assignment is simple - read today’s story and allow it to remind you of a time you were on a golf trip with the guys (or gals - we didn’t forget about our fabulous “Ladies of the CCC”) and send us your story HERE. If it makes the cut, you might see it in your inbox on a Thursday morning one of these days!

🔹 Comment Contest Winner announced below. Remember to vote in the poll and leave a comment for a chance at a prize from CCC mailed to your doorstep!

Every golf trip has a mark. Most trips, nobody knows who it is until the third night. On this trip, they knew before the wheels were up, because the mark was the guy who booked the jet. He was generous. He was fun. He was, after a certain number of drinks, dangerously agreeable. And he was traveling with friends who were more conniving than he realized.

This is the story of one such man, and the three-day golf trip that began with him believing he had invested two million dollars in an ice sculpting business.

The trip began the way these trips always begin. Four guys from prestigious Los Angeles clubs, a destination resort of the Pinehurst-Pebble-Bandon variety, a hotel bar with a wine list that functions more as a credit check than a menu. The golf wasn’t secondary, but the next-day hangovers sometimes made it feel that way. The opening itinerary was what it has always been, which is to say dinner, cocktails, more cocktails, and whatever stupidity the evening produced.

If you have spent any meaningful time in the bars of these resorts, you know they can run the gamut. At one table you have a group of college buddies that saved up for ten years to play a once in a lifetime course. Right next to them, a table of young investment bankers on their fourth trip this year. 

At this resort, the private jet crowd comes in around six. The sharks come in around seven. You can watch it happen in real time, a guy in a quarter-zip approaching a foursome and asking what they do, and within four minutes the word "Cayman" has entered the conversation and nobody knows how it got there. These are not malicious people, necessarily. They are just people who understand that a man who has flown private to hit a little ball around is a man with liquidity and an elevated willingness to hear a pitch.

Our protagonist had a well-documented party trick. He would drink past the point of any reasonable human being, slump forward in his chair like a man receiving terrible news, appear to be clinically unconscious for several minutes, and then bolt upright with the sudden clarity of a stock trader hearing the opening bell and announce that it was time for shots. This had happened on every trip anyone could remember. It was a feature, not a bug.

On the first night, the group fell into loose conversation with another table of guys at the bar. Some chatter about deals. Some chatter about businesses. Nothing serious, nothing binding, the kind of ambient networking that happens when men of a certain tax bracket encounter other men of a certain tax bracket in the wild. Our hero participated enthusiastically, as he participated enthusiastically in all things, and then he hit the wall. The slump arrived. The eyes closed. The group moved on.

This is where it gets good.

One of the guys on the trip was a commercial real estate broker who had done legitimate deals with the sleeping man. He had, on his phone, a perfectly valid DocuSign signature page from a prior transaction. He looked at it. He looked at his unconscious friend. He looked back at his phone. And somewhere in that sequence, an idea was born that would sustain a three-day golf trip in ways no course architect ever could.

By morning, with the help of an assistant back in Los Angeles who was either extremely loyal or extremely well-compensated and possibly both, the documents existed. A two million dollar capital commitment. A signed investor agreement. A pending wire transfer request. The business in question, chosen with the kind of cruelty that can only come from genuine friendship, was an ice sculpting company.

Not ice. Not cold storage. Not a logistics play with industrial refrigeration upside. Ice sculpting. Swans at weddings. Pixar characters at bar mitzvahs. The kind of business that does not exist at scale because it cannot exist at scale.

Our man woke up hungover in the specific way that only a man who tried to out-drink his own liver can wake up hungover. The documents were presented. His signature was right there, unmistakable, because it was actually his signature. He squinted at the paperwork. He tried to do math. He could not do math. He asked, tentatively, what exactly he had agreed to.

The answers came from every direction at once.

"Dude, you were so into it."

"You kept saying the margins were incredible."

"The guy was a great salesman, I'll give him that, but two million is two million."

"I don't know, man, ice sculpting? Really?"

"Hey, at least this investment is guaranteed to have a liquidity event. Just not the kind you want."

"I mean, I try to avoid frozen assets, but that’s just me."

And so began three days of golf during which our protagonist played some of the worst golf of his life while quietly trying to reverse-engineer the worst business decision of his life. 

He asked, at various points, whether drunkenness might constitute grounds to void the agreement. He was informed, gravely, that he had appeared quite lucid at signing. 

He asked whether anyone had the sculptor's phone number. He was told it was being handled. 

He asked, on the eighteenth hole of the final round, whether two million was really that much in the scheme of things. Maybe ice sculpting really was an overlooked asset class? Reader, he was trying to talk himself into it.

They let him off the hook on the tarmac. Because that is what friends do, eventually, and because you cannot reasonably keep a prank running at thirty-five thousand feet with nowhere for the victim to go. The relief on his face was reportedly visible from the control tower. He did not get angry. He did not threaten violence. He laughed, the way a man laughs when he has just watched his own funeral and realized it was someone else's.

Then he looked around the cabin at the three men who had spent seventy-two hours convincing him he had wired two million dollars to a swan carver, smiled, and said, "Well, it looks like for our next trip, you guys are flying commercial. I'll meet you there."

And so, dear reader, we close with this. Back in high school and college, the worst thing that could happen when you blacked out was to wake up with a phallus drawn on your forehead in Sharpie and a mild sense of betrayal. The stakes were low. The tools were crude. The recovery was a shower.

When you get older, and richer, and your friends get older and richer and more conniving and have assistants who know how to use DocuSign, the pranks grow up with you. The canvas is no longer your forehead. The canvas is your bank account. The Sharpie is a wire transfer request.

So be careful out there. The road is a dangerous place if you are not prepared. The sharks at the hotel bar are the least of your problems. The real danger is the man sitting across from you who has known you for fifteen years, just watched you fall asleep in your soup, and happens to have your signature saved on his phone.

Drink accordingly.

If you were the caddie, do you take the job?

🟩🟩🟩🟩🟩🟩 $200 extra on a loop? I’m walking 36! (62)
⬜️⬜️⬜️⬜️⬜️⬜️ I’d do it once… then get cold feet (5)
🟨🟨🟨🟨⬜️⬜️ No chance - not getting in the middle of that (45)
🟨⬜️⬜️⬜️⬜️⬜️ Only if I never have to meet the wife (20)

Looks like about half of you would take the money and not look back, but there are some strong high-moral readers within the CCC membership that wouldn’t take the cash. Kudos to them. Their wealth isn’t measured in dollars, it’s weighed in peace-of-mind… but they have a lot less cash in their wallet!

Congrats to comment contest winner D.B. for this gem: “I'm not helping to fuel the warranted suspicion women already have over golf outings and trips with the boys.”

He wins a Short Par4 golf towel and all he had to do was vote and make a salient point - you could do that! Give it a shot!

And finally, don’t forget to catch up on past stories at ccconfidential.vip - and while you’re at it, tell a friend!

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