If there is one investment that has more to do with the heart than the head, it’s vineyards. It is also one that lends itself to jokes whose punch lines are always about losing money.

But that risk has never deterred wealthy people. Nor has the current economic malaise damped their spirits. These are people who made fortunes in profitable industries like shower doors and title insurance but define success in the winemaking business as breaking even. And most seem to accept the prospect of losing a manageable amount of money over many years.

Don Ross, founder and chairman of Cardinal Shower Enclosures, offers a particularly telling example. He bought 2.5 acres in the Napa Valley in 2003. It came with rows of cabernet sauvignon vines. A lifelong wine lover — he has 7,000 bottles in his cellar — he started making wine under the label Shibumi Knoll . Then, he bought some chardonnay grapes from another vineyard and made that, too.

The business was going along modestly until 2005, when Mr. Ross gave a bottle of the chardonnay to his golf pro who passed it on to his next client, an influential wine critic. That critic later rated the wine a 97 out of 100 in a blind tasting, and Mr. Ross’s phone started to ring.

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