1. An experiment in radical openness.
I started blogging in 2002/2003 as a way to post bug fixes that I’d discovered up onto the Web in a way that I and others could quickly find them. For example, if I got an “Parse Error #123 in dorklib.so,” and I found out how to fix it, I’d post up both the error message and the fix so that anyone searching on the error message would find the fix right away.
That worked really well for that limited purpose. I didn’t get a lot of traffic, but I did get a decent amount, and folks tended to leave positive comments. I wasn’t influencing crowds, but I was improving a few people’s lives each week at no marginal cost to me. Karma bonus. Bloghisattva.
Then, right after coming to work for Voyager Capital in late 2005, Web 2.0 and the social web were really taking off. I got the news, and decided I needed to really dive into the culture of “radical openness.” Sort of getting on board with the MySpace generation (I’m a few months away from actually being a member — rather, I’m the youngest possible “Gen Xer”).
The idea is pretty simple: dive into the conversation, push your ideas and your self and your self-image out there. Privacy is old school, promiscuity is the new fad. I covered this in “Your Old-Ass Values Are Broken.” It seems to work well for some people. Fred Wilson, a well known VC, has lots of readers for his cartoons of gay jokes, tales of how much he plays video games, and posts saying things like “fuck Apple”. Decorum, farewell! You have been relegated to the recycle bin of history!
When Real Grownups, like Fred Wilson, do the high-personality, low-filter thing, you end up with something like an unvarnished truth: lots of input, fairly low signal to noise ratio, and occasional obscenity or flagrancy — but in exchange, you get a measure of honesty, a personal “voice” that engages the reader, and an (imagined) human connection with the writer.
So, as I stated in “Plan Less, Write More”, I decided to do less — a lot less — planning, filtering, and proofreading, and just let it hang out. Hey Fred, wait up, I’m hoppin’ on board too!
But, there are a couple of problems with that idea.
2. I rant too much when I’m radically open.
The main problem is pretty reducible to an abstract model. Fred writes pretty much every day. So do most of the 20 or so bloggers I regularly read — generally, at least a couple entries a week. At that rate, most of the entries end up being pretty tame and moderately well thought-out, even though they have this “unvarnished” quality.
But I’ve been blogging once or twice a month on average. Why do I blog so much less than a real “blogger?” Well, because it hasn’t been a priority for me. So, my entries tend to happen when I get particularly worked up about sharing something with the world — in chemistry terms, I have a high “activation energy” for putting out a blog post, and so I only post when I’m agitated.
The effect of this, of course, is that I seem to rant a lot. If I’ve come up with a novel observation on the VC industry, or a new tech trend I think is interesting, but I’m not worked up over it, I probably won’t write about it. But if I’m having a shitty day, and some software bug or ill-considered policy really tweaks me off, then bang, I settle up the bill with an excoriating blog rant faster than you can say “Fred’s your uncle.” (Sometimes, happily, I think better of it before pushing the post out to the Web, but often not.)
So, I end up with a strong bias toward rants. Probably not the best.
3. Domain blogging would be good.
What could fix this? Well, “domain blogging” is one possibility, where I create a single blog based on one topic and really hammer on it. (I’ve tried vainly to separate things into categories here but they end up pretty spread out with no critical mass in any one.)
The problem with domain blogging in my main domain of activity — venture capital finance of early stage tech companies — is that the best and meatiest observation and analysis of the industry is the worst possible thing you can put into a public blog.
My job is all about relationship, resource, and information asymmetry. We make it our job, eight days a week, to cultivate relationships with the right people, to raise funds for our discretionary deployment, and to form proprietary opinions on market and technology trends. Then, we go around trading and arbitraging these things, like for like, and for equity in a startup, and eventually for dollars returned to our investors.
So, the meatiest things I could post here would be about those relationships, or resources, or that information. Which, of course, is like laying out a dish of dollars for all your competitors to see.
Within the world of VC, my situation is generalizable, but not universal. Back to our exemplar par excellence (sorry, Fred), there actually are some circumstances in which radical openness within the domain is a successful strategy. If you can, leveraging the Web, get a dominant mindshare among the wired crowd by means of your openness, you might cast a much larger shadow than you really have, and actually attract to yourself valuable relationships, resources, and info. But it’s a fat-tail game even within the fat-tail industry of VC, and it’s risky: it’s like shooting the moon in Hearts. Or like chopping blocks of ice with your hand. If you break through, you’re golden! But if you don’t, you’ve only managed to harm yourself in the process.
It’s probably OK for me to keep posting observations on the quirks of the industry, or purely functional / mechanical advice for newcomers, like my “VC Jargon” post.
4. Don’t shit where you eat.
There’s another issue with domain blogging, too. The more senior, and more independent, the VC blogger, the more he can get away with. Junior executives of any stripe remain, in certain ways, beholden to the norms of their seniors. (I touched on this in “VCs and the Naughty Bits.”) Even a completely independent entrepreneur, unless he wants forever to bootstrap or self-fund, can’t stray too far from the comfort zone of his investors while in the public eye. (Nobody’s smacked me down for this yet, but at this rate it’s only a matter of time until I piss off the wrong person.)
I used to think that, amongst the giants of this industry, I was like a court jester — free to say whatever I thought, or whatever might seem funny or entertaining, even if it involved the king. How could the king get upset at a mere jester? A few events I’ve been to recently have changed my mind. Do you really want to be introduced over cocktails to someone whom you’ve accused (even indirectly) of having the skill set of a “retarded chimpanzee?” Yeah, me neither. Seattle’s a small town, but guess what? Silicon Valley’s a small valley (sic), NYC’s a small metropolis — in fact, it turns out it is a small damn world, after all. The chances of me sitting next to any given F50 CEO, Senator, Rails core developer, or hedge fund manager are individually pretty small, but OR’ed together and over a few years, end up approaching p=1. Might not want to badmouth too much (even if it is sort of in good humor and mostly about the issues, not the people).
(Note that it does not escape me that this is one of the self-reinforcing traits of capitalism: every step up the ladder of wea
lth and influence that one takes is simultaneously a greater investment in the same system and a deeper barb into one’s flesh. One is less and less able to speak truth to power the higher one gets; gotta keep one’s reputation for playing a good clean game. Want to silence those upstart rabble-rousers? No need for a hit man; just give ’em promotions and fat raises.)
5. The problem with Steely Dan.
Blogs are ostensibly written for the outside world to read. The author is dying to be a star, and make them laugh, right? But we all know that really, blogs are written for the writer to write. The further out the long tail the blog is, the truer this is, until N(readers) approaches 1, the author himself.
At the peak, I had just over a thousand uniques monthly to the blog (most were RSS readers). Yay! Even I can’t go visit my own blog from a thousand different cybercafes each month, so there must have been some actual readers. But let’s make no mistake: I was getting no material (in either sense) benefit from my readership, so we can pretty much assume I was writing just for moi.
And so, predictably, I indulged myself with things like addressing the “gentle reader” and making gratuitous references to Steely Dan or Beatles lyrics. This alone isn’t a huge problem, but it doesn’t exactly help mitigate the other issues. (“Hey, this VC associate just said my developers must have ordered extra lead paint chips on their breakfast cereal before coding the UI for my product, but then he threw in a line from ‘Pretzel Logic’ in the same post. Maybe he’s not so bad after all!”) Jackass allusions are fun easter eggs when a co-conspirator spots them, but they just confuse everyone else and make them think you’re off-kilter.
6. Technical commentary is still appropriate.
Technical commentary, including bug fixes and product reviews, are still very much appropriate. I think that using adult language is still probably OK, too, although after reading the now-infamous Zed’s commentary on Rails I am rethinking just how cool it actually is to use the potty-mouth when talking about software.
7. Conclusion and next steps.
Sadly, this means I will be stripping most of the humanity and voice from the blog. Which is OK since, frankly, the “radically open ranting voice” wasn’t the best version of my voice anyhow. It also means I’m going to back and strike all the “big red words” from this little blog, or at least the most rant-a-licious parts. Sure, they’ll still be cached somewhere, so an amateur historian of the inconsequential could still see just how indiscreet I once was. But this isn’t about revoking or burying what once I said, but merely taking it off display, thus failing to renew implicitly my imprimatur.
And so now, gentle reader, this author as you have known him must say adieu. Not radically closed, quite, but back to the paleo-openness of Web 1.0 goes this blog.