When I was 30, I sold a business and was thinking about my next gig. I was focused on buying a company. My brother had worked for this PE backed business in town that was totally dysfunctional, but had great bones. So I approached the firm about buying the business. Obviously PE firms usually sell through an investment banking process so chances were slim. But this firm had offered me a job, so I knew them fairly well. Thought it couldn’t hurt to ask. I reached out and they were willing to talk. I soon realized what they really wanted was to understand why I thought I could be a better owner. What they didn’t realize was that the CEO was an absolute narcissist. Anyway, I told them I wanted to buy it and run it the rest of my life, so my time horizon was better suited to this particular asset. That’s meeting one. Meeting two - I should’ve known - would be different. They sent a VP. This was literally the guy who got the position I had turned down a few years earlier. Not sure if he knew that, but we had lunch at a bbq place. He was UVA MBA which he let me know pretty quickly. We talked, I told him why I was excited about the business and that I was a serious buyer who could close. After a few minutes, the 28 yo told me “I just don’t see you as a CEO.” I actually laughed out loud. At the time I had been CFO for a business that just sold for nearly a billion. I mean, maybe he was right but just the brazen insult to my face made me chuckle. I told him thanks for the feedback. Maybe he was right, but if I could buy the business, that would be my problem. Anyway, as you would expect, it didn’t work out for me. For them, it did. They fired the CEO a couple months later and the business started to take off. I had fun kicking the tires and I got the added benefit of some young nerd adding to the chip on my shoulder.