In 2010, Oldman is releasing Oldman’s Brave New World of Wine, published by W.W. Norton. Filled with unique stories and graphics, the book focuses on helping readers make the most of the unprecedented diversity of wines now available. It details several dozen insider wine types of moderate cost and maximum appeal, and also includes the exclusive wine picks of oenophiles such as Jodie Foster, Hilary Swank, Antonio Banderas, John Lithgow, and Guy Fieri . It will be released on September 9, 2010.. Mediabistro.com wrote of Oldman's "exceptional voice" in an article which describes his book deal with Norton.

In 2005, Oldman wrote Oldman’s Guide to Outsmarting Wine, published by Penguin Books and winner of the Georges Duboeuf Best Wine Book Award. A contributor to Publishers Weekly commented that "robust, hearty, and full bodied describe not just a Beaulieu Vineyard Cabernet Sauvignon but also this comprehensive wine guide for the novice oenophile." The book is published in Japan by Sony and in France in four volumes by Editions Solar, which also publishes the French volumes of American wine critic Robert Parker.

Oldman is lead judge in the PBS TV series The Winemakers, filmed in Paso Robles wine country in California. Season two of the PBS series has finished casting and has commenced filming.

Oldman writes and lectures widely on wine. He delivered the keynote address at the Boston Wine Expo and appears at the South Beach Wine and Food Festival, the Food Network New York City Wine and Food Festival, and the Aspen Food and Wine Classic, among other top festivals. He also contributes to several lifestyle magazines, and has written a wine column and chooses the wine picks for the magazine Every Day with Rachael Ray. He is a regular on Martha Stewart Radio's "Living Today" program on Sirius Satellite Radio.

In 1997, Oldman co-founded Vault.com, a popular media company focusing on career information. He served as president of Vault.com until its successful sale in 2007 to a major private equity firm. With his co-founders H.S. Hamadeh and Samer Hamadeh, Oldman won Crain’s Top Entrepreneur's Award, the Harvard Business School Club’s Entrepreneur of the Year, Silicon Alley Reporter’s “100 Most Important Internet Executives,” and Deloitte & Touche’s 50 Fastest Growing Companies.

Oldman received his B.A. and M.A. in English from Stanford University, where he graduated Phi Beta Kappa. He also received a J.D. from Stanford Law School, where he won the Hilmer Oehlmann Jr. Prize for excellence in writing. Oldman has served on four major boards of Stanford, including its board of trustees, for which he was chairman of its Special Committee on Investment Responsibility.