[18][19] After graduating from college in 1992, Oldman and friend Samer Hamadeh conceived of and co-authored America's Top 100 Internships, published by the Princeton Review imprint of Random House.

The book profiled the internship opportunities at such companies as Intel, Boeing, the Wall Street Journal, Walt Disney Studios, Rolling Stone, and MTV.

[23] Along with Hamadeh, Oldman won Crain's "Top Entrepreneur's" award[24] and was included on the Silicon Alley 100 list of influential tech executives.

[25] Oldman was lead judge in the PBS television series The Winemakers, filmed in Paso Robles wine country in California and in the Rhone Valley in France.

It includes interviews with Hilary Swank, Francis Ford Coppola, Matthew McConaughey, Jodie Foster, Ludacris, Geddy Lee, John Lithgow, and other high-profile wine lovers.

[39] In 2016, he published How to Drink Like a Billionaire (Regan Arts/Simon & Schuster), which details insider methods to obtain the best value bottles and master wine in restaurants, shops, and at home.

The majority of Bevinars focus on an educational wine subject, while others feature Oldman interviewing a top winemaker such as Marcus Notaro of Chappellet Vineyards or Jeff Mangahas of Williams Selyem.

The Bevinars style was largely honed during Oldman's many appearances at major food and wine festivals, and has been recognized by The New Yorker,[53] the Washington Post,[54] and Business Insider.

[55] Oldman is a noted art collector, with interests in Walton Ford, William Eggleston, Wayne Thiebaud, Harland Miller, and Vija Celmins.