If you just missed becoming a millionaire or even a billionaire, do you regret it?

Answer by Yee Lee:

Of course I regret it, how could you not?! 

I was at PayPal pre-IPO and had a chance to work with Steve Chen and Chad Hurley.  Back then, PayPal's product development process was very Product-driven and as a young PM.  I loved that about the place; it was an exhilarating job/experience.

When I was getting ready to leave PayPal in late 2005, I remember having a conversation with Steve about product management positions at YouTube.  He said, "Y'know, we didn't really like the way product managers and engineers interacted at PayPal.  So here at YouTube, we want engineers to lead product decisions.  So we kinda just want PM's to take notes on what the engineers decide and make sure that stuff gets done."

I mulled that over, thought that sounded terrible, shook my head, and told Steve that maybe we should chat again when he was ready to bring on-board a *real* product manager.  I WAS (maybe still am) SUCH AN IDIOT!  I had an opportunity to talk with the founders of YouTube about being one of the first (if not the first) PM and I didn't even engage in the conversation because I had held precisely one (1) product management role before in my life and therefore assumed I had it all figured out…  Sigh.

In hindsight, I think careers in Silicon Valley are so dependent on luck, timing, and who-you-happen-to-know that a lot of us probably have gone through these kinds of near-misses.  In fact, I think that's one of the things that makes the Valley special — the business ecosystem is connected enough here that just about everyone knows someone or has a friend-of-a-friend that experienced major personal career success.  That proximity to success creates a lot of readily available role models and exemplars that drive the aspirations of the whole Valley.  It's not just the top universities, the long tradition of technical innovation, and presence of venture capital or other legal/support functions…   Other countries have tried bringing all those factors together into "innovation hubs" and not been able to replicate Silicon Valley.  It may be because they're missing the social-connectedness and success role models that we have!

I think the regret of a few missed-opportunities is a small price to pay for working in the greatest innovation center on the planet!

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