I was invited to speak at a startup panel about fundraising, and, by some strange coincidence, I found myself sitting next to the first venture capitalist I ever tried to raise capital from. I couldn’t help but chuckle at the situation. There I was, in front of a room filled with hundreds of entrepreneurs, and I was going to explain how to raise money while sitting next to the first guy who rejected me.

To be fair, even though I recognized the VC, he surely wouldn’t have remembered me because our one and only conversation had taken place nearly 20 years prior. Heck, the only reason we even talked all those years ago was thanks to a mutual connection. But entrepreneurs never forget the first venture capitalist they pitch, so the sting of my rejection from this particular VC still felt as fresh as if it had only just happened a few days earlier. READ MORE