Investments that Will Bring You Joy

Putting money into things you love can fill your soul and your wallet. Here’s how to make your dreams pay off

Jean Chatzky
Photograph: Illustrated by Yuko Shimizu

ALMOST TWO years ago, my husband and I decided to invest in a Broadway show. We found a group that allows small investors to buy shares in a production for a minimum of $10,000 and got on the mailing list. For a few months, we received information on various shows: A Little Night Music with Catherine Zeta-Jones and Angela Lansbury; Leap of Faith (based on the Steve Martin movie) with Brooke Shields; and a ballroom-dance spectacular called Burn the Floor. We said no to the first two (Night Music because, although we love Sondheim, not everyone does, and Leap of Faith because I didn’t like the movie) but put $10,000 into the third. Why? It had two of the dancers from Dancing with the Stars, a huge hit. We thought that would be enough to make it thrive.

We pretty much figured wrong all around. Night Music made money for its investors. Leap of Faith tried out in L.A. and is currently being reworked for Broadway. And Burn the Floor? It opened but never caught fire. We haven’t seen a dime—and the last communiqué to investors doesn’t make it sound as if we will. “I think you’ll probably lose it all,” says Steven Baruch, a producer affiliated with Richard Frankel Productions (, the group we invested with.

Even though we lost our money, it was a thrill to be thatclose to the theater. There are certain investments—in wine, restaurants, art—that I lump into the category of “play money.” If you’re already funding your retirement and your kids’ college, if you’ve avoided massive debt and are willing to take a flier on up to 10 percent of your portfolio, why not follow your bliss? Especially if you invest in a way that maximizes your chances of making the money back—and then some.

If it’s grapes that get you going, there are two primary ways to buy in: by becoming involved with a winery and by acquiring bottles, storing them and hoping they appreciate. Though some investors choose option one, that’s a bad idea, says Joe Bastianich, owner of four wineries. The price of admission is higher than that of most “passion” investments (high five figures to low six at a minimum), and holding on to that money is extremely difficult. “If you want to make a small amount of money in the winemaking business,” he says, “the best thing to do is to start with a large amount.” In other words, he advises that you steer clear entirely.

The second way—buying investment-grade wines when they’re first put on sale (but aren’t ready to drink) and holding them—“is how you can make money,” Bastianich says. That’s not to say it’s easy. Choosing a wine to drink is about taste; choosing one to invest in is about finding a wine that will quickly appreciate in value. Websites like and Wine-searcher .com keep data on how much money wines have sold for recently, and has listings of wines for sale. You’ll see that returns on some fine wines have been in the range of 12 to 14 percent annually.

How do you identify those “hot” wines? Start with Bordeaux, says Ann Feely, vice president of wine sourcing and sales for Vinfolio. “It’s the one category that’s traded like a stock and has proven to appreciate reliably,” even through the recession. “In terms of the wine-investment world, Bordeaux is the safest.”

First Published August 23, 2011

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