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All three of Union Square's investments have been guided by these bullet points. There's Instant Information, a startup that's applying the open-source model of collaboration to Wall Street research. There's Tacoda, an online advertising outfit that's working on a system for behavioral ad targeting. And there's Del.icio.us, a startup that describes itself as a "social bookmark manager."

What all these investments reflect, as well, is Wilson's enduring passion for media, marketing, and finance -- three industries he thinks will be turned on their heads by the proliferation of Web services. "The Web is going to capture an increasing share of people's attention, and billions of dollars are going to flow in," Wilson says. "What Web 2.0 is about is harnessing those dollars in highly leverageable ways." Pointing to Google (GOOG) and Yahoo (YHOO) as examples, he says, "The potential profitability here is simply amazing."

Wilson may be right about that, but he shouldn't get carried away. If what he's saying is true, the capacity of any firm to defend its position is likely to be vanishingly small. An explosion of Web services, cheaply and quickly produced and released, may prove a massive boon to consumers. But that doesn't mean that it will cough up a plethora of highly profitable companies -- or a slew of big scores for VCs. Moreover, none of Union Square's investments at this point exactly has "the next Google" written all over it.

[Business 2.0]
More tidbits:
Instant Information - founded by Multex.com founder and Multex.com CTO. Flatiron also invested in the fourth and mezzanine round of financing of Multex way back in 7/97 and 12/98.

Tacoda - Founded by David Morgan, a founder of 24/7 Media. Tacoda is backed by Masthead and Union Square. If anyone from the firm is reading this, your "About" page is broken