One of the biggest red flags for me when I am pitched is when the entrepreneur talks about how he (or we) are going to make money. Or they talk about exits. Or they talk about how a competitor is worth $1 billion. None of that matters. A startup is a mission. A great entrepreneur is a missionary. Not a mercenary. A great irony of entrepreneurship: The entrepreneurs who come in and say they're going to make everybody money, don't. People who say that they're going to paint a picture of the world that's never been seen before often are the ones who make a fortune. When entrepreneurs leave their cushy Facebook or Google jobs, some of them can't stop looking back. That is a bad sign to me. If the entrepreneur ever says, I could be making $XYZ at Google, I am concerned that they've got one foot in and one foot out and won't make it as a founder. The same can be said for founders who are building a company for the resume versus the mission. There's been an influx of Ivy League MBAs who believe that starting a venture-backed company is the next logical career move. I'd much rather invest in someone who has found a problem and believes with every fiber of their being, and knows deep in their bones, that they're the one who is destined to find the solution.