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Last year I got a last-minute invite to a partner event in San Francisco. The kind you don't turn down - cocktail reception on a private yacht touring the harbor.
Booked everything last minute (classic)…. flight, hotel, rental car. Four thousand five hundred dollars on the personal card, to be expensed later.
Before the event, I grabbed beers with a former colleague near the waterfront. The event started at seven and my plan was to show up 5-10 minutes after. One Kona Big Wave turned into two, then three.
We got to the harbor at 7:02. By the time we found the dock, the boat was forty feet from shore and moving with the casual confidence of something that was absolutely not waiting for us.
I watched my $4,500 expense report sink to the bottom of the harbor.
Thank god, we weren't the only ones left on the dock. A woman arrived at almost the exact same moment. We started talking. Turned out she was an active prospect my team had been chasing for two months. Invited her to dinner. Great conversation. Justified the expense report.
My (former) company still doesn't know I literally missed the boat.
Moral of the story: do as I say, not as I do.
The customer dinner guide is below.
The Briefing
Stories you should know
The Masters patron gnome retails for $50. The 2026 version — a ceramic caddy with a working umbrella — was already listed for $2,500 before the tournament ended. The 2016 original just sold at auction for $28,800. Augusta is now reportedly considering discontinuing it entirely, which will only make this worse.
My take: put the Masters logo on anything and I'm interested. That gnome can sit in my attic or office. I promise you it’s not touching my front yard.
Meta is building a photorealistic, AI-powered version of Mark Zuckerberg trained on his mannerisms, tone, and company strategy — so employees can interact with him at scale. He's personally involved in training it.
My take: companies spent four years trying to rebuild culture after COVID sent everyone home. Now the solution is apparently a photoreal robot of the founder. Call me crazy but I don't think that closes the gap.
The Unwritten Rules of Customer Dinners
Dress like you have somewhere else to be. A sport coat over a collared shirt handles most situations. If that's not your style, wear something you can actually talk about — a golf polo from a course you've played, a sweater with a subtle logo that means something to you. You'd be surprised how often someone asks. Conversation starters that don't feel like conversation starters are worth more than you think.
Take control of the table. If you’re the organizer. Own it. Order two appetizers without asking if anyone wants appetizers — they do, they just won't say it. Before anyone starts doing the mental math on what's appropriate to order, just say it: "I'm buying — get whatever you want." Ten words. Completely disarms the table. Nobody's staring at the right side of the menu anymore, and you've already told them something about how you operate.
If you're the guest, be decisive. Someone went out of their way to invite you to dinner. The least you can do is have an opinion. When they ask about appetizers, say what you want. "I don't care" sounds polite. It's not, it just creates more work for the person trying to host you. Anything but the most expensive thing is fair game.
Before anyone opens a menu. "Do you guys want a drink?" Yes means one follow-up: "Wine or cocktails tonight?" Sets the tone in ten seconds. If it's wine, be honest with yourself about what you're looking at. No shame in saying: "I'm not going to pretend to be a sommelier — if anyone knows what they want, take it." If nobody does, ask the server what's popular. For cocktails, the classics exist for a reason. Whiskey sour, tequila neat, vodka soda. Avoid anything that arrives with a garnish requiring an explanation.
When to talk business. If your contact brought their boss, they're performing a little - get to the purpose of the meeting earlier, save the personal for later. If it's peers, go personal from the jump. Either way, watch how they order. Decisive or indecisive. How they treat the server. Whether they're asking questions or already know what they want. You'll learn more in the first twenty minutes than three months of discovery calls.
Follow up the next morning, not Monday. Skip the templated "great connecting" email. One short text, something specific from the night. In Austin last year I sat across from a guy who mentioned his kids were learning golf and heading to Atlanta for spring break. Next morning: "If you're bringing clubs, let me know — I'd love to get you out." No pitch. No agenda. Just proof you were listening.
The Best Thing I Heard this Week
Rick Rubin was asked how he produces records when he doesn't know how to play music. The interviewer pushed: "Then why do people come to you?"
"For my taste."
For me, people ask me how I've grown on Twitter or come up with content ideas.
Honest answer: the most traction I've ever gotten came from talking about things I actually like. Stories that stuck with me. Topics that interest me. Shit that makes me laugh.
That's taste. Trust yours.
Until next Thursday,
TG
P.S. I reply to all emails
