“You know what I wish for you?,” Philip Rosedale said from across the table at a trendy Italian restaurant in the Marina. “I want you to wake up naked and penniless on a beach in Brazil because that’s the way you’re going to reach your full potential. You gotta eliminate the safety net.” As the sentence ended, I half expected a bag to be put over my head while Philip leaned over and whispered softly “this is my gift to you” as I was dragged away to a South American cargo plane.

However it turned out he was just providing advice, not a one way ticket. I’d spent three years helping him build the virtual world Second Life and we parted during a downsizing round in late 2003. Afterwards I’d unexpectedly found my way to Google (unexpectedly because I was planning on staying in the startup space) and continued to have dinner with Philip every few months to catch up. He’s an intense guy with a very unique way of looking at the world so his perspectives took some digesting, but this one in particular always stuck with me. It shot back into my frontal lobe when reading Sarah Lacy’s acquihire article along with the the subsequent debate about whether “fear of failure” is a good and necessary requirement for healthy entrepreneurial cultures.

Philip’s visual of severing the safety net would seem to suggest that you have to be afraid of the fall in order to soar, but what he really meant was to avoid getting too comfortable because you lose an edge. Eliminate the safety net less it turn into a hammock.

I don’t believe acquihires are fundamentally good or bad things – it’s just an outcome. However they do tend to leave people in jobs that they wouldn’t have sought out through normal employment channels. If it turns out you love your project in the larger company, then stay. But if you don’t feel as challenged, productive or passionate, then get out. Don’t rest and vest. Don’t give up years of learning for short-term earning, especially if you’re learning skills that are company specific. Let’s be real – much of being an executive at a large company is about understanding relationships, politics and “how to get things done.” These aren’t always the most valuable skills if you imagine getting back out into the startup scene. Stay through a product launch and a few planning cycles and you can understand “the Google way” or “the Facebook way.” Then get out and resume building companies that do it a totally new way.

Oh, and yeah, Philip, as I approach nine (!) years at Google/YouTube, might need you to burlap sack me south of the equator 🙂