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I sat down with Molly Bossardt, a boutique wine marketing strategist who traded New York tech startups for Italian wine country, and we got into everything the wine industry doesn’t want to admit out loud. Molly runs her agency from Torino, Italy now, helping family-owned wineries modernize their marketing and actually connect with the humans buying their bottles – not just the collectors hoarding them.

We talked about why wine has always been tangled up in class and performance, how her own mom got shamed for putting ice in her Merlot, and why that kind of gatekeeping is quietly killing the industry’s future. I shared my own moment of discovering that bubbles are genuinely amazing after decades of being a red wine loyalist, and Molly broke down what she’d actually pour someone who’s never really explored wine before, starting with a proper sparkling, no Prosecco allowed. We also got into the real tension at the heart of every winery: are you making art for yourself, or a product for your customer? Because you can’t quite do both without deciding first.

If someone handed you a glass of wine you’d never tried before, would you rather they tell you everything about it first – the region, the vintage, the tasting notes, or would you prefer to just taste it blind and form your own opinion?

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