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EP 03 May 5, 2026 Pinehurst, North Carolina

Pinehurst — The Trip We Almost Didn't Take

Booked nine months out, almost cancelled twice, ultimately the trip everyone in the group still talks about. No. 2 lived up to it. The cradle did not.

Guest
Sam P.
Destination
Pinehurst, North Carolina
Budget
$2,200–$2,500 / person
Run-It-Back
One-and-Done (Worth It)
Guest44/50FOMO8/10Value8/10One-and-Done (Worth It)

Listen

The Setup

Four guys. Two of them friends since high school, two of them friends only because the first two are. By Day 3 you wouldn’t be able to tell which was which. That’s the trick of a good golf trip.

The Format

Match play. Old-school. Two singles, two foursomes, totaled across the three big rounds. No money on the line — just a dinner buy at the Carolina Hotel for the losing team. (For reference: that dinner is not cheap.)

What’s Worth It

  • No. 2 in person is somehow more demanding than every video makes it look. The crowned greens are not a meme. They are real.
  • The Cradle at sunset, two beers in, is the most fun nine-hole anything any of these guys have ever played.
  • Pinehurst No. 4 doesn’t get enough love. Get a tee time on it.

The Off-Course

Carolina Hotel rocking chairs. Pizzeria on the village square. Caddies who have absolutely seen worse golfers than you and will tell you so politely.

Why “One-and-Done”

This isn’t a knock — Pinehurst is a pilgrimage. You go once, you cross it off, and the next “big” trip needs to be somewhere else (Streamsong? Sand Valley? Cabot?). The MOD captures the worth-it-ness without forcing it into the annual calendar.