I thought long and hard about this next step, and in the end chose to do it over what I've known to be a very fulfilling and exciting career as an entrepreneur for two reasons.
First, throughout my entire entrepreneurial career, things have been much more concrete: I saw things that I wanted to work on and just dove right in, come hell or high water. These last few months though, I've been primarily thinking about the entire Internet venture ecosystem, and specifically, what seems to be a worrisome trend here in Boston (thanks Bill Warner) , with fewer and fewer startups turning into big companies that can bolster tech entrepreneurship in the region. I want to see this ecosystem thrive for very selfish reasons: it makes living here, a much more interesting experience.
So I had two choices: take another swing at making another big company, or try my best to find as many possible nascent ones as possible and help them as much as I can through investment, strategy, recruiting, and general ecosystem reinforcement. I've chosen the latter for a variety of reasons, but the most important one is that I am ready to make a sector bet on this next phase of the Internet's evolution in a way that I never would have before.
What?
I am fairly confident about the following statement: the Internet will continue its rapacious pace of absorbing just about every facet of business, and more significantly, regular life. Advertising, media, entertainment, commerce, communications— even staid industries like manufacturing are all being transformed by open protocols, ubiquitous connectivity, and more efficient information exchange— in short, all that has made the Internet the best platform ever.
At the same time, everything else is up for grabs: UIs for access (Android, iPhone, iPad, TV?), models for computation (the client, the cloud, a hybrid?), business models, and even basic patterns for work and play. More than any other time in my career, has the map been so confusing towards such a clear long view.
And rather than be tied to one 7-10 year bet on how to make a big contribution to our ecosystem, I've decided to zoom out and bet more widely on the entire space. I am sure that we'll get some monster hits out of this primordial soup— and I hope I get a chance to help with a few of them.
The second reason why it was a hard decision to make was because I hate being a freshman, plain and simple. And when it comes to investing in tech companies, I've clearly got a lot to learn.
One of the possibilities that I considered was in the emergent models for seed/A funds built by former operating entrepreneurs. There are a few of these funds run by folks I've gotten to know and respect, and there might be just be an opportunity for them to carve out a permanent niche in the supporting environment that sustains startups.
In my case though, I wanted a chance to learn the business from folks who have been at it for a few decades and who have shown repeated success across industry changes in helping entrepreneurs get big. And there is little doubt that Matrix is the place to do that (as the freshman in the class, it's a little daunting).
For sure there is an element to be learned around identifying the right bets to make but I was more concerned with understanding how the best investors seem to be able to provide help all along the way, nurturing and guiding entrepreneurs until their small companies grow to fit their big visions.
I presume this stuff is not going to be easy but I'm looking forward to the challenge.