It’s Okay to Start Over

That journey as a CEO hasn’t always been smooth. It never is for everybody. Can you share with us what happened at one of your companies, Pay Cycle? And what advice would you give to others who are grappling with a scenario where certain team members are no longer the right fit for the next phase of the company’s growth?

Yeah, I think the learning there at Pay Cycle, I had started with a co-founder, and we had a board member that we brought on as our COO. So, we had three people, really, running the company. But ultimately, what I would conclude is that when you have three people making decisions, you only make decisions on the things you agree on. That’s the easy path, right? You don’t make the decisions on the hard path. So, as long as everything’s easy, it’s great, because there are lots of easy decisions to make. But when you get to a fork in the road, it’s like, you know what, it’s time to make a hard decision. And oftentimes, we would just not make a decision, we would just kind of say, “Okay, well, that was too hard for us to figure out.” So, we move on to the easy decisions.

And so, the learning there is, really being accountable, making sure there’s accountability for running the company and the decisions that get made. And it ended up being a discussion where we decided that the best thing was for me to step down as the CEO, to recruit a new CEO. And then after about a year, I thought, I had this idea for Bill for a couple of years and I wanted to go start over and take the learnings about being a leader and apply that in a different setting. And so, that is what happened and it’s something that I take with me – that accountability is just so important, you can’t not feel it.