In the startup world we’re used to hearing about billion dollar outcomes and massive exits. We’re all living the dream that our startup might be the one that turns into gangster retirement wealth. And, chances are, so are the people we’ve eagerly handed stock options to. We’re all hoping for that massive Powerballesque exit.

Yet, what if I were to suggest that a massive exit isn’t the only life changing outcome? What if I were to suggest that a $250,000 lump sum check might have more life changing impact than anything? Not because it’s more valuable than, say a $10 million check, but because it will likely have more near term impact and more importantly — you might actually get it.

Base Hits versus Home Runs

We’re all sort of used to a...