Yes, every time after I was a CEO. And that was my fault.
The first time was after being acquired. It’s tough. Going from CEO to a VP is a challenge. I didn’t mind having a boss. But, I was deeply passionate about growing the business. I needed my sales team. They wanted to send them to Utah. I needed my customer success team. They wanted to fire them and move the function to Idaho. Etc. etc. I was a threat to Business as Usual. But I only knew how to grow 100%+ annually one way. I knew I had no chance without my team doing things my way.
I should have just chilled and done things their way. The growth rate ended up slowing down after I left, but maybe it wouldn’t have mattered if that had happened a bit earlier. The business has still grown to $100m+ ARR.
A bit more on that here: If You Get Acquired, You’ll Need to Learn to Move from Persuasion to Alignment | SaaStr
The second time was tough, too. It was tough being a professional investor and not being in charge, even though my investments then were pretty good ones (Pipedrive, Talkdesk, Aloglia, Salesloft, etc.) and are in the top 5% of venture returns.
I wasn’t very good at going to meetings I didn’t want to go to, or supporting investments I didn’t believe in, or really going back in time to in essence being a VP and not really being part of governance.
Probably not fair, but I am wary now of hiring ex-CEOs. I need to make sure they want the role for the right reasons. And that they are at least 90% OK reporting to someone else, and doing things their way.
Because I’m not. Not anymore.