Collectively their rationale:
- Marketplace Opportunity - The perception that investment dollars continue to flow freely and it's a good time to start a company.
- Credibility of my CV - Bloom of Google and media interest in Second Life means that I've created a resume which appears to be especially attractive to suitors.
But recognizing (and exploiting) the combined glow of Google + Second Life is giving me pause because I do feel that we're likely at a local maxima with regards to their perception. Google is, well, "GOOGLE" and the hype around Second Life is bound to turn into backlash at some point -- it's just the PR cycle. To paraphrase, "How do you get rich on Wall Street? By selling too early."
That said, it just feels like a bad guiding principle to try and assume that my chip stack is higher now than it will be in the future, especially since i generally have confidence in both companies. And I've never made decisions by trying to actively optimize this aspect of my life - i just follow my nose towards people and ideas that excite me. So altering that now to try and capitalize on my aura feels like a will o' the wisp, pulling me astray.
So when do you hold them, when do you fold them? Coincidentally I'm seeing a bunch of friends in the coming weeks who might have opinions (serial entrepreneurs, VCs, VP-level ex-Y!/etc peeps) and I'm going to ask them about this question. Will update responses here.
Advice from the Front:
ex-VP Y!, current VP major internet co: "You only leave the big name company once" so make it a worthwhile stepping stone.
ex-VP Y!, current consultant/angel investor: Your learning curve can only be one of three directions - up, plateau, down. The minute you hit a plateau find a way to angle back up in your current company or go find something else to do.
ex-eBay exec passing along wisdom from a b-school prof: Don't spend four years getting two years of learning.
serial entrepreneur: a variety of advice incl asking me to consider that while even if i'm approaching a local maxima, I'm likely better served by waiting slightly past the peak than changing too early.