Chairman of the Bard
An entrepreneur stages Shakespeare for the masses.
By Coeli Carr

(FORTUNE Small Business) – This summer thousands of theatergoers will gravitate to an open tent at the Boscobel Restoration, about 50 miles north of New York City, for a few hours of greed, envy, jealousy, and power struggles. It's all presented--with the Hudson River as backdrop--by the Hudson Valley Shakespeare Festival, co-founded by Terry O'Brien, now the festival's artistic director. This month O'Brien's company will begin performances of The Tempest, followed by The Two Gentlemen of Verona in July.

O'Brien, 52, has run the festival for the past 18 years while also overseeing the software company he owns, Ovid Ink (named after the Roman poet), which designs custom programs for small businesses and takes in more than $300,000 a year in sales. During the summer theater season, which runs through August, he spends anywhere from 30 to 80 hours a week on the festival; the rest of the year it's about 25 hours. "Any society that wishes to sustain or maintain itself absolutely must have and promote culture," he says.

The type of culture he promotes has drawn positive reactions from critics. "What's most impressive is the plays' accessibility to a very wide audience," says Ben Brantley, drama critic for the New York Times. "The productions are bare-boned and make wonderful use of the incredible natural backdrop."

O'Brien studied acting after college and soon began directing theater productions in San Francisco, where he developed his signature approach to Shakespeare: "Very minimal setting and costuming," he says. "We've always eschewed scenery and lots of props, so your attention doesn't drift away from what's going on among the people onstage."

He moved to New York in 1984 and three years later helped stage a production of A Midsummer Night's Dream at a site near the Boscobel Restoration. The community loved it and asked for more the following summer. By the start of the second season O'Brien had formed a nonprofit, assembled a board of directors, and scheduled As You Like It. Each summer some 25,000 people attend HVSF productions. The nonprofit draws its $1.1 million budget from private donors and pays a modest annual stipend to O'Brien, who is married with two children. (He declined to specify the amount, though on a per-hour basis it would probably violate labor laws.)

Of course, he doesn't do it for the money. "Watching actors bring a script to life and seeing how the audience responds to it is unparalleled," he says. "I feel very lucky."