Weinberg said that he's realized he does his best work when he goes to sleep, dreading just how busy he'll be the next day. "The weeks that I do the best work or feel like I did the best work is every single night before I go to bed, I'm like, 'Ah, shit,'" Weinberg told investor Harry Stebbings during a recent episode of Stebbings' "20VC" podcast. Harvey is one of the hottest names in the closely-watched legal AI startup space.
"Here we go again, I thought", as I listened to the board member tell me how frustrated he was with the founder of one of their venture firm's most promising investments. Sadly, I knew the call was likely too late to prevent an inevitable cascade of emotional and financial consequences. Working as an executive coach in Silicon Valley with venture capital firms and the companies where they have placed their investments means being at the confluence of high-stakes financial and career risk.
Six years ago, I asked Sam Altman at a StrictlyVC event in San Francisco how OpenAI, with its complicated corporate structure, would make money. He said that someday, he'd ask the AI. When everyone snickered, he added, "You can laugh. It's all right. But it really is what I actually believe."