Invest In Your Own Startup?

What if you were given the opportunity to invest your own cash - out of your salary, or another source - in the startup company where you work? Would you do it? Would you take money from family members and quietly invest it under your name?

Clearly, there are many good reasons why not - you are, probably, not capable of deploying enough capital to spread your bets around to a basket of high risk/reward startups. You already have stock options, so you stand to make some money if your company takes off. T-Bills offer higher returns than those 'lower quartile'(half?) venture funds. You name it.

But what if you were early at Google? Then would you invest additional cash? What if your company wasn't quite that kind of rocketship, so your decision to invest cash made a material difference to your wealth? What if you were given the opportunity to invest cash before it became clear that Google was Google?

This is one useful lens to view your startup job through. There are countless benefits to startup jobs - great people, tons to learn, excitement, relaxed rules - but face it, you're not saving the world in your day job, the point is to get rich.

So, would you invest?