Well over a decade ago, before journalists striking out on their own was à la mode, Jessica Lessin left The Wall Street Journal to found The Information, a Silicon Valley–obsessed news site that she has since built into a still small but formidable and profitable business. In the process, she helped ignite an important trend in media. Now, she is trying her hand as an investor, sprinkling her money around a few of the more recent media startups—Semafor, The Ankler, Dynamo, etcetera—that are hoping to achieve similar success. In a wide-ranging discussion on The Grill Room, my twice-weekly podcast, Jessica shares her investment thesis and the lessons she’s learned over a decade, and also addresses why she has yet to eye an exit.