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…

By a happy accident of history — mostly because Bill Gates and Paul Allen were born here and Jeff Bezos moved here to start a company — Seattle is now one of a small handful of global hubs for technology innovation.For both selfish and not-so-selfish reasons, I’d like it to stay that way, so I continue…

In the beginning was the banner ad. And the banner ad sucked. On the second day Amazon invented affiliate marketing, Google created AdWords and a brave new world of performance-based digital marketing was born. Stretching this allusion to the breaking point, it’s now roughly mid-week, and performance marketing has exploded into dozens of niches (many of them continue…

Every founder has one. That little clock inside your head telling you how much time you have before you run out of runway. If you’re still bootstrapping, maybe the metric is cash in the bank divided by your monthly living expenses. If you’ve raised outside money — especially if it has preference or automatic conversion continue…

The rumor mill is heating up on Amazon’s plans to enter the smartphone business — a fiercely competitive market currently dominated by Apple’s iPhone franchise and Google’s Android platform. Despite massive investments, Microsoft has so far failed to make inroads as a third platform, so Amazon will have to pull off some very impressive work continue…

As an investor, I love marketplace businesses — from craigslist and eBay to Etsy and Kickstarter, digital platforms that empower individual seller / entrepreneurs are one of the opportunities I love most. But last week’s Padmapper brouhaha — and Amanda Peyton’s dead-on analysis — were an important reminder of just how hard functional marketplaces are continue…

I’ve hugely enjoyed Blake Masters‘ transcripts of Peter Thiel’s Stanford CS183 lecture series (if you haven’t read them I can’t recommend them highly enough). Two of Theil’s most powerful ideas — secrets and monopoly-seeking — came together for me this morning in a conversation with a local entrepreneur. This post is a quick recap of continue…

As part of my ongoing research into the making of high-performance entrepreneurial ecosystems, I’ve begun spending more time with folks at the intersection of the private + public sectors: city and state economic development professionals, university commercialization offices, public finance experts and the like. My first lesson from these conversations is the how critical public-private continue…