Already delighted to discover that Trader Joe's was founded by a GSB alum named Joe Coulombe, '54, it was fun to find out that the namesake of two buck Chuck, Charles Shaw, is also one ('71). But as it turns out, he sold the rights to his winery, which bares his name, at at time of personal financial turmoils for $27,000. Trader Joe's got the brand for a steal, and Shaw sees none of the profits.
Some of his issues stemmed from how leveraged the Charles Shaw winery was - they needed strong growth to keep cash flow positive, but this was at a time when the interest rates he was facing were about 20%, and his marriage was failing. His wife, who he described as a person who "didn’t drink wine and didn’t even like to talk about wine" ended up with the winery, and lost the distribution deal in place, which included selling throughout the US and in 20 countries. Bankruptcy soon followed.
Shaw's regrets include the poor relationship he had with his business partner/wife (no kidding) and the fact that he was too rigid in the wine space he wanted to play in. He wanted to be the "light red" guy, so he focused gamay varietal from the Beaujolais region of France, but feels like he should have instead produced "a chardonnay, a merlot, a sauvignon blanc, for example," then gone to the market and observed the demand. Even in the wine world, iteration and market observation is key.
Source: https://www.gsb.stanford.edu/experience/news-history/charles-shaw-mba-71-risk-rigidity
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