How do I keep wine club members from cancelling?

Wine clubs and retention

Most members warn you before they leave: they skip a shipment, stop opening email, or let a declined card sit. Watch for those signs, talk to members when there's no box to sell, and give new members extra attention in their first year.

The wine club stopped being a growth engine. Net club growth fell to about 2%, so new signups are barely covering the cancellations.

That makes the club a retention game. A member is worth around $2,400 over about 34 months, and both numbers slide the moment you stop paying attention to people.

The plays that work have one thing in common: they find the member who's drifting before the cancellation email arrives. Skipped shipments, ignored invitations, a card that failed, a tasting room signup who never came back. The five warning signs play walks through each one.

Start with your own data. Pull the members who left in the last year, look at what they did in the months before, and build a short at-risk list from it. Then reach out to that list this week, with no shipment attached.

Plays

Every play

Sales and RetentionSpot the five warning signs before a club member cancelsMost members warn you weeks or months before they leave. Track the signals, find your steepest drop-off, and step in before the cancellation, because keeping a member pays better than chasing a new one.From the Jun 3, 2026 issue Sales and RetentionTalk to club members when there's no box to sellThe clearest club fix in Silicon Valley Bank's 2026 report: high performers engage members outside the shipment cycle. If members only hear from you when their card is billed, that's your attrition problem.From the Jun 9, 2026 issue

Numbers

Every number

2%Net wine club growth fell from 13% in 2021 to about 2%Silicon Valley Bank, Jun 9, 2026 $2,400A wine club member is worth about $2,400 over 34 monthsSilicon Valley Bank, Jun 9, 2026

Prompts

Every prompt

Operations promptThe staff training and vibe guideA one-page cheat sheet for new tasting room hires, written in your brand's voice.

Tools

Every tool

Free to startClaudeAn AI writing and strategy partner for copy, analysis, and thinking through business problems.Paid plan neededClaude CoworkClaude working with the files on your own computer, producing finished documents, spreadsheets, and decks.Free to startHeyGenAI avatar videos: type a script and a digital presenter speaks it.

Apps

Every app

Free app, October 12, 2026Club Cancellation Risk ScorerDrop in your club export and see which members are about to cancel, why, and what to offer them this week.

Issues

Every issue

Work with Jeremy

Reading the plays is the easy part.

Changing what your team does on Monday morning is harder. Book a 30-minute strategy session with me, and we'll work out what to change first and how we could work together.

Book your session

30 minutes on Google Meet