Insights

Open notebook with handwritten notes and diagrams, a magnifying glass resting on it, a pen nearby, and stationery on a wooden desk with potted plants in the background.

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.

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Less Storytelling. More Truth-Telling

People are getting harder to impress and easier to lose.

Not because marketing stopped working.
Because people can feel the difference between performance and truth.

The future belongs to the brands, leaders, and cultures willing to be real:

  • real values

  • real accountability

  • real connection

  • real humanity

Less storytelling.
More truth-telling.

Because authenticity is no longer soft branding.
It’s market positioning.

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Poppi built a brand on one brutally clear sentence.

Poppi didn’t win because they “did marketing better.”
They won because they built a brand that knew exactly who it was, and let that truth drive every decision.

This isn’t a soda story.
It’s a leadership and culture case study on what happens when alignment creates speed.

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