Jerry Colonna was a high-flying venture capitalist in New York City at the height of the dot-com boom. He looked like the picture of success—but as time wore on, he felt more and more like a fraud. And when the boom went bust, it all began to unravel for him. Alex talks to Jerry about that struggle, and about how it led him to his current life as one of the most in-demand executive coaches—who just happens to be Alex’s own executive coach. This episode discusses suicide and mental illness. If you’re feeling depressed or you just need to talk to someone, you can call the National Suicide Prevention Lifeline. The number is 1-800-273-8255. The StartUp episode referenced in this conversation — the episode that includes one of Alex and Jerry’s sessions — is called “Shadowed Qualities.”