I started this blog almost five years ago, on November 6, 2007. This is my 365th post and — as of today — this strangely personal collection of ideas, impressions and hypotheses has been viewed more than 200,000 times. I know that’s a drop in the ocean given the 2+ billion connected humans in the continue…

One of our portfolio CEO’s made me laugh — and think — this week by describing a new investment opportunity I’m pursing as “very postmodern”. As an undergrad American Studies / Lit geek I spent many happy hours puzzling over the ambiguous and perspective-shifting fiction of writers like Don DeLillo and Donald Barthelme, but before this continue…

I had yet another conversation with a talented entrepreneur today in which I tried to explain why early-stage venture investors (as distinct from angel investors) can’t afford to bet on “small” opportunities — where “small” is defined as exit values in the single- or low-double-digit millions of dollars. I remember being puzzled and annoyed by continue…

I first heard this phrase from one of my favorite co-investors. We we chatting during a break in a board meeting in which the CEO was predicting a quick, favorable outcome on a very large enterprise deal. The investor’s summary — which turned out to be correct — was that the CEO had “happy ears”: continue…