A record of what happens when twelve guys decide the wine moms have had this idea long enough.
The same organizer has run it since day one. This is what the email trail says actually happened, chapter by chapter, since the first invite went out.
The founding email is, verbatim, a pitch, a wink, and a legal disclaimer all at once.
Tyler's opening line did the whole sales job in one breath: a Wine Advent Calendar, but for the twelve guys who'd never admit to wanting one — a daily countdown treat for grown-ups, minus the chocolate. He titled the email "PSA: This Is Not A Pyramid Scheme" and got ahead of the obvious comparison before anyone could make it: no recruiting required, nothing owed, and no hard feelings for anyone who sat it out.
The original ask was steeper than it is today: 12 guys, each contributing two bottles (one local/favorite around $45–60, one high-end "hard-to-get") plus $25 to cover reusable sample bottles — framed as "~$135/pp aka ~$5.50/drink (the price of a shitty Vodka Soda at the bar) for 24 unique, interesting, & hard-to-find whiskey/liquor samples/cocktails." Each sample shipped with a description card: tasting notes, a cocktail recipe if applicable, who submitted it and why, and "any other personalized Christmas wish the submitter wants to share." The best two-bottle haul won a 2021 Wild Turkey Rare Breed Rye, Barrel Proof — straight out of the founder's own stash. By 2025, the retelling had a name for the moment: "what began as 12 young'ins dipping their toes in the world of whiskey during COVID lockdowns."
Same 24-day format, six different years of logistics chaos.
No repeats among the 24 submitted bottles. Introduced Mixed-Drink Monday and the tasting-sheet tradition. Several "sorry for slacking" catch-up emails bundled multiple days together near the end — a pattern that would repeat every year after.
"Hope y'all enjoyed the first sample (or first 7 samples if you are Connor or Caleb)."Dec 2, 2021
576 samples poured and shipped, arriving as "76 pounds" of bottles with zero breakage. Launched a password-protected tasting site to keep spoilers off group chat, plus the first community ranking sheet. Brian W.'s Four Roses Single Barrel won the bottle-of-the-year prize.
A Kentucky distillery trip supplied kickoff trivia ("over 200,000 legal distilleries in US history"). QR codes debuted on sample bottles, linking to tasting notes — and promptly proved "touchy" on curved glass. Rankings simplified to one score per day, hidden in white-on-white font until reveal.
"Well, I think I finally understand how Santa feels after the craziness leading up to Christmas…kicking back the next morning with a glass of whiskey by the fireplace and finally relaxing."Nov 24, 2023
The usual organizer stepped back that November for a wedding — brutal timing to also be running a 24-person whiskey operation. The tradition didn't skip a beat: a bonus 25th sample was added for Christmas morning, and new Google-poll rating categories (nose, palate, finish) debuted. The year's running joke: Jeff P. in Milwaukee finally received his 2022 and 2023 samples, almost simultaneously.
The first year with a formal waiting list. Selection quietly shifted from first-come to committee discretion. Brian W. made a second generous donation. Minnesota deliveries ran through a genuine relay — one driver to Lakeville, another to Woodbury, a third redistributing five more boxes on the west side.
"PSYCHED with the heavy hitters we have so far…we are averaging 114 proof and $107 MSRP for all bottles currently received!"Oct 27, 2025
Closed to new participants for the first time — the 24 seats went to returners chosen as "first round draft picks." Kickoff email published the full five-year data table. Tasting begins December 1st.
"The waiting list for this snowballs each year, so unfortunately (and fortunately!), at this time we aren't opening 2026 up to new participants."Sept 23, 2026
Des Moines is home base; Minneapolis and Kansas City are the two satellite hubs, with bottles routinely "muled" by whoever happens to be driving up for an ISU game, Thanksgiving, or (once) a wedding.
The house term for an unusually good bottle, used in kickoff teasers and Day 1 reveals alike, almost every single year since 2023.
Born in 2021: certain Mondays get a themed cocktail recipe instead of a straight pour — ginger beer and lime, or brown sugar and orange, mailed out with the day's sample.
Every year charges a small per-person fee to cover sample bottles and packaging — $25, then $20, $22, $20, $22, drifting with whoever's running it that year.
2021 was "first 11 friends to reply." By 2026, returning is earned: years participated, bottle generosity, and how easy your city is to ship to all factor into the committee's picks.
The default valediction since the very first email in 2021, occasionally swapped for "Cheers" or, once, "Feliz Navidad & salud."
"As a man of my word and an example, Jeff P. in Milwaukee was just delivered his 2022 AND 2023 sample bottles roughly one month ago…better late than never, right Jeff?!"
Kickoff email — Nov 12, 2024"The waiting list for this snowballs each year, so unfortunately (and fortunately!), at this time we aren't opening 2026 up to new participants. That said, YOU have been selected as a first round draft pick…"
Season kickoff — Sept 23, 2026"Full disclosure up front: I get married in less than two weeks and thought there was no way to be able to coordinate the Fourth Annual Whiskey Advent Calendar amongst the craziness of planning…"
Kickoff email — Nov 12, 2024