My goal with this blog

I write about relevant changes in the way that people use the web and how startups are built to provide services and products for this ever changing wonderful thing we still know as "the web." As a former entrepreneur turned early-stage investor, my greatest hope is for this to be useful to other folks that are like me in the hopes that they can avoid some of the mistakes I've made.

I am back

Since 2004, the last two months have been the longest break I've had from blogging. In the olden days of personal publishing this would have been a horrible admission that I took two months off from thinking. But in today's world of fortune cookie blogs, the hiatus felt more like a break from being at a cheap dentist office looking at posters with titles like "Motivation," "Teamwork," and "Ambition."

Fortune cookie blogging?

You know the type: usually a picture of a sunrise, steaming coffee mug, egg, or other suitably vacuous visual metaphor followed by a bullet list of aphorisms thinly disguised with power adjectives (epic, awesome, killer) and a personal confession on the part of the author of some realization that seems obvious to us but is Earth-shattering to him, short only in lifetime impact of the day he discovered that retweeting is easier than thinking and goes a lot further for the page views.

And to boot, because these posts are viral by nature within the veal pens they circulate in, the missives are usually sprinkled with a set of links to a whole host of other equally inane posts, some of which can be about "deep" personal matters like diet, exercise, and a desire to practice a Zen-like minimalism that requires shopping only at the Apple Store, the Moleskine online depot, and the local Prius dealer.

Combine with the fact that I've now been a VC for almost a year and a half which brings with it the guilty feeling that I ought to be writing "VC posts" and it is not surprising that it may take more than a double dose of Milk of Magnesia to cure this particular constipation.

VC posts?

As far as I can tell, these come in three varieties, two of which overwhelm the channel to the detriment of the third. To those that came to this racket from "operating" (working class) origins, they entail writing about experiences you've had with a deity-like certainty that the choices you made along there way were predestined and completely generalizable for eternity in the world of technology where the only constant is constant change. You certainly wouldn't want to write that you were making the shit up as you went along and got lucky to have a few breaks go your way— or that if you were especially lucky, you had some really bright people around you to pull your head out of the manure when you firmly planted it there.

The other variety of VC posts center on the fallacy that an interested party can give you the "inside view" of how to work "the capital raising process." In my view, these skirt the fortune cookie genre the same way vampire novels border on the bodice ripper— they get tantalizingly close to the goods without giving you the good stuff. For instance, they tend to neglect to mention that competitive dynamics in the deal process drive a lot of the speed (and nonlinearity) of the raise. Or they also neglect to mention the ugly underbelly of the VC industry— namely, that almost none of those well-coiffed, smart, charming, entrepreneur friendly, "buddies" of yours from the last three summer cruises have ever returned a dime of profit to their taskmasters (the limited partners)— and trust me, at the end of the day, we're all working for someone here.

As an aside, it'd be great for some VC to write a "down-and-dirty VC blog" where they treat these topics honestly and directly— it would be much more humanizing than the sunshine up your butt drivel out there today and would definitely separate said author from the current sea of sameness in investorland.

The third kind of VC blog is as endangered as the bald eagle but just as pleasant to find: it's sharp, well-researched, and somehow blends personal experience with portfolio learnings in a way that makes entrepreneurs bookmark it for constant reference. I am obviously biased but my partner and former board member David has what I consider to be the best of this variety of blog at For Entrepreneurs.

So if I'm back and I'm not into fortune cookies or VC blogging, what am I left to write about? I used to enjoy writing about technology so I think I'll start there, though that gets harder the further away you get from it. I'll also likely take on some of my favorite Boston entrepeneurs that others don't naturally tweet about (sorry SJ, but you're all washed up anyway), both past and present. And, in case it wasn't clear from this GI-clearing post, maybe even a little bit of irreverence— if only to clear the collective gastrointestinal tract.

Anything else I'm missing?