American entrepreneur and philanthropist Steve Case, 51, made headlines during the dot-com gold rush of the late 1990s as the cofounder and chairman of AOL. Since leaving the company in 2003, the Hawaii-born executive has kept busy, dedicating time to his eponymous foundation and investing in a spate of companies ranging from agricultural holdings to resorts to health care. A longtime wine lover, Case has recently turned the tables, going from wine collector to industry professional. When Vinfolio, an online wine store and platform for person-to-person sales, stumbled financially earlier this year, Case became a significant investor under the umbrella of Revolution, a company he founded in 2005 to invest in tech-friendly businesses. He spoke with associate editor Jennifer Fiedler to discuss why he jumped at that opportunity, what type of wines he has been collecting, and how his tastes have changed.