The companies Fred Wilson has bankrolled define our daily lives: how we communicate, how we connect, where we go. Mr. Wilson is one of Silicon Alley’s pioneers: he co-founded Flatiron Partners in 1996, through which he ushered in the first wave of web companies, including Kozmo, New York Times Digital and Geocities, which he sold to Yahoo for $3.5 billion in 1999. Mr. Wilson survived the flame-outs of the dot-com bubble and moved on to found Union Square Ventures, New York’s most successful venture capital firm, in 2003. Union Square gets in early, leveraging small investments for potential bonanzas. (The same strategy means it needs the vision to see a company’s potential at its birth, maybe even before its market or industry exists.) Mr. Wilson didn’t create the Web 2.0 social media revolution, but he sure bankrolled it. Before you ever heard of them, he was betting on and incubating Twitter, Tumblr, Foursquare and Zynga. Not content merely to manufacture the Internet experience, Mr. Wilson tirelessly explains the process of how it happens, blogging almost daily on AVC.com.