Fred Wilson barely needs an introduction for his role and impact in the startup community both as blogger and co-founder of Union Square Ventures. Fred’s also a big reason why I’m here giving this intro: his blog ultimately led me to meeting and now working with Jerry; and his family podcast, Positively 10th Street, was one of the first podcasts I ever listened to. Feels like things have come full circle. So I’m thrilled to have Fred join Jerry for this episode. In 19 years of friendship and partnership in the startup world, these two have seen just about everything. In this conversation they share some stories from the Flatiron Partnership days, what makes a perfect board, the importance of trust in investing, and what makes a good leader. They even discuss the sheer terror they felt on their own entrepreneurial journey. There’s a lot of great material referenced in this discussion, so we’ve gone ahead and compiled a bunch of links from this show on our podcast page at reboot.io/podcast. In what we hope will be a series of several, enjoy this first Reboot conversation with Fred Wilson and Jerry Colonna.