It’s particularly important for leaders and managers to model the culture that the company tries to foster.

The Grind — Most investors at hedge funds work at a sociopathic pace, especially relative to the west-coast cultures of most VC firms. It is very hard to regularly compete against a team of people who work ~16 hours a day 6-7 days per week.

A great board member, Dan, called me to say, “Ryan, I’ve never in my career seen a CEO as worn out as you. Please, you need to take a sabbatical — at least six weeks”. He, and other board members, tried so hard to do the right thing and convince me to take care of myself. But after a lifetime of gritting things out, I told myself I didn’t need to take a break. I think an element of my reaction is what Jerry Colonna calls “false grit” in Reboot.

Why I chose to step down as CEO of CircleUpOver the past year, when I began telling team members, investors, LPs and other stakeholders about my transition, their first question was, inevitably, “Why?” I typically explained that the average founder/CEO of a startup is in the seat for less than five years; I had been with CircleUp for nine, and I was exhausted. But there was so much more to it than that.I don’t remember the first time I told our board that I was exhausted and needed to step down as CEO. I imagine it was around 2016 or 2017, a period defined by stressful business decisions and physical and mental health issues. I later realized that the board interpreted my complaints as “typical founder/CEO exhaustion”. I blame myself for that lack of clarity. For years I did a poor job of communicating the depth of my stress and exhaustion, a problem only compounded by the fact that, at times, I wasn’t even sure of my own feelings. There were stretches of time where I felt horrible — lonely; terrified; depressed. Depression exacerbates exhaustion. But I tried to put on a brave face to make sure the board felt comfortable.