When Alyssa Rapp came to Stanford as a graduate student in 2003, she learned that business and pleasure do, indeed, make a good pairing. "I didn’t expect to end up doing wine," says the 28-year-old entrepreneur, who, as a diversion from her business studies, co-presided over Stanford’s Graduate School of Business wine club. "We were 400 members strong, with students from all over the globe whose families were involved with wine, or worked in the business. But what I learned is that there are still so many bright, well-educated people who are still intimidated by wine." Since graduating, Rapp and her business partner, Kim Donaldson—who, as a member of the wine industry, previously hosted wine tastings for the student club—have created Bottlenotes, a network of established collectors and budding oenophiles, with education, experimentation, and entertainment in mind.

The top tier of the club, Limited Addictions, features small-production wines (such as Arietta, Diamond Creek, Spring Mountain, Bacio Divino, Abadia Retuerta, Barrua, Storybook Mountain, and Dry River) from around the world, and access to a virtual cellar that keeps track of all your wines, not just the ones received through the club. The online management system allows you to rate your wines and share your tasting notes with other members. But what makes the club unique is that it will customize wine shipments to your personal taste preferences, based on the answers you provide in a series of online questions, such as how you take your coffee and whether you salt your food. You continue to build your profile each time you rate a new wine. But the experience is not all virtual; the club will host several private winemaker dinners and tasting events next year in San Francisco, Los Angeles, Chicago, and New York, where like-minded members can meet and compare tasting notes. Membership is capped at 500 and is by invitation only, which has been extended to the readers of Robb Report (invitation code: LTDADDX). Fees range from $1,080 to $10,000 a year, depending on bottles ordered and frequency of shipments.

Bottlenotes, www.bottlenotes.com