Insights
How I ended up joining a $1,400 wine club I definitely didn't plan on joining.
The tasting fee was nearly double any other winery we'd visited.
Fair warning sign number one, which we noted and ignored.
By the end of the afternoon we had been wowed by the setting, the sommelier, the panoramic patio, the spotless crystal glasses, and approximately six generous pours of exceptional wine.
We signed up for the wine club.
It was not six bottles as advertised. The club required a twelve-bottle annual commitment.
My brief moment of hesitation was quickly buried under the combined weight of the experience, the wine still warming my chest, and a complete unwillingness to look cheap in front of a very elegant Italian sommelier.
This week I'm writing about what Checkmate Winery did brilliantly — and what every brand can learn from the way they turned a tasting into a $1,400 commitment I never saw coming.
The Best Loyalty Program Costs Nothing
I spent years building and running a loyalty program.
Points structures. Redemption catalogues. Breakage calculations. Vendor relationships. System integrations. It was complex, creative, and genuinely one of my favourite stretches of my career.
But the whole time, there was a question I couldn't quite get away from: are loyalty programs solving the right problem? Or are they a workaround for something more fundamental?
Then I found an honest mechanic. And he answered it for me.
This week's post is about the loyalty program that costs nothing, and generates more word-of-mouth than any structured program I've ever seen.