Chips, and when to cash them in

When should you be opportunistic? Over the last six months an increasing number of people have been urging me to seek new professional opportunities. Basically dangling VP level positions at various media/internet/tech co’s or offering resources to help me start a new venture. This advice is coming from people who are self-interested (e.g. recruiters) but also people who have less of a direct motivation to try and loosen me from my Google socket.

Collectively their rationale:

  1. Marketplace Opportunity – The perception that investment dollars continue to flow freely and it’s a good time to start a company.
  2. 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.

For a number of reasons I’m uninterested in leaving Google any time soon. Furthermore, perhaps too confidently I dismiss the ‘marketplace opportunity’ argument. Linden Lab was angel funded in the freeze of 2001 and survived through several years before traditional investors came on board. There’s a glut of venture and private equity capital that will continue to chase good people and attractive ideas.

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.