I love learning from other CEOs, but it’s difficult. Most conversations with CEOs are disingenuous because they are always posturing, and contrary to what I used to think, honesty doesn’t always help them open up. Especially not in the distributed corporate that is Silicon Valley. Whenever I do get some authentic interactions, my favourite type of CEOs are those who founded and run companies that used to be hot, but aren’t anymore.

Note, not failed companies. Most of them run companies that are bigger and/or have higher top line than TrueAccord or ones that were acquired. They used to be hot because they operated in a hot segment and VCs were throwing money at them and their competitors. They raised a bunch because you eat when you’re fed. Some of them are running 300-500 person organizations with deputies with incredible pedigrees and well oiled sales machines. By all accounts they should be on the top of the world.

Like everything else, though, it’s not always the case. Interests aren’t as aligned once you’re not hot. Reasonable acquisitions are rejected, sometimes undermined, because investors think they can get a bigger number to put on Twitter. Founder comp doesn’t get updated as fast as their needs. The push for growth creates unprofitable behemoths that have to continue to raise from an ever shrinking pool of organizations (each managing more money than ever, for sure) and getting profitable seems like an ever elusive dream. Struggles for control are common and if founders are not, say, geographically removed or otherwise protected they face imminent risks to their role. Most of all, they are tired. The 5 year mark is a real thing, and yet these founders don’t feel like they can rest; sometimes they don’t even feel like they can hire a second in command because they fear a VC implant that will undermine them.

I learn a lot from these founders because they are grizzled veterans by now. They’ve seen a lot. Most of them will continue to succeed and the majority of their days and weeks are on a high note. It just serves as a constant reminder for me that there is life after being hot and the strings you agreed to when you thought this wave will never break create a pretty mean entanglement. It’s one of the most crucial issues we don’t spend time thinking about early on that comes back to haunt us later.