I’m rereading Ben Horowitz’s . If you haven’t read it, it’s well worth reading.

The book is an attempt to be brutally honest about how hard is to build a company, as well as give some advice on how to survive the hard times.

I learned a lot from reading about Ben’s experience.

So in case it’s of use to you, here’s some summaries / lessons from my very hard times in my own professional career.

Leading School Development Work Without Instructional Knowledge

NSNO had two experienced educators leading our new school creation work. It was very hard to find two top notch instructional people and we’d done a lot of recruiting to get these awesome folks and I thought we were in good shape staffing wise. I was wrong. They both had children at roughly the same time and I ended up leading our school support work while they were out.

Even writing this now, I feel some sense of embarrassment and guilt as I was 100% not ready for the job. I remember being very anxious and feeling dread going into the schools we working with. They were all start-up schools that needed excellent support and I knew that I personally could not give them the support that they needed.

There is really nothing more to say other than I showed up and did what I could and kept the work moving until our team was reassembled.  The only thing I think I did well was stay calm and focused. I never freaked out publicly and I kept our support visible. We kept on showing up to schools. I’m not sure there is anything I could have done different. It was an external shock and sometimes when external shocks happen you just have to survive.

Failing in Raising a Major Fundraising Round

NSNO was trying to raise somewhere around $15 million for the city and we arranged a final pitch day for our biggest funders. They flew in from all over the country and for the day we put them in front of high status speakers and panels full of our best educators. Then, at the end of the day, they said they needed some time to debrief. So our leadership team, including our board chair, left the room for about an hour. Then we came back in. The funders proceeded to tell us that they weren’t ready to make another major investment; that they still had too many questions.

I was shocked. I thought we had everything lined up. I thought we put on an awesome day. And I felt passionately that the work had to continue; that we were on the cusp of something very very important and that they were going to abandon us. With as much calm as I could muster, I told them this; that they needed to invest. I was very young at the time and if my voice wasn’t shaking audibly my mind surely was shaking. They said they understood where we were coming from but that they weren’t ready to invest. The meeting ended. I went up home to my girlfriend and cursed loudly about how the funders were abandoning us. Then I drank a few bourbons and went to bed.

Shortly after, we told the staff that were unsuccessful in getting the commitments we needed. I forget what we said or how we said it. Mostly what I remember is creating a plan to go back to each of the funders individually and figure out what their concerns were and make sure we fixed it. This is what we did. Eventually we raised more than we had initially set out to raise.

The reason the day was a failure was all our fault. Instead of understanding our funders’ concerns and having deep discussions about these issues, we put on a dog and pony show for them. They were rightful frustrated, and, I think, felt like they had wasted much of the day. Putting on this dog and pony show both kept them from getting the information they needed and made us look like we did not have our shit together. The reason we were able to get through it is that we were very dogged; we did not hold grudges; and, ultimately, we put forth a realistic and compelling vision of what we could accomplish as a city.

Failing to Lead the NSNO Management Team

When I first became CEO everyone on our management team was much more experienced than I was. And while I was confident in my ability to develop our organizational strategy and communicate this vision to internal and external stakeholders, I was not confident in my ability to manage senior staff who had more content knowledge than I did. So instead of building a management team I simply met weekly with our senior staff to make sure the work was moving. I did not set high expectations for the work; I did not build trust amongst the team; I did not provide thoughtful feedback; I did not create an atmosphere of debate.

During our first 360 performance review, I received brutal feedback. The management team made it very clear that I was failing to lead them. It was extremely, extremely difficult to hear. I was emotionally hurt and for about a day couldn’t even really deal with it. Then I got my act together and met with each of them to figure out how I could get better. I built a plan to become a true leader of the management team and mentally committed myself to deliberately managing the team. Soon after, we did an off site retreat and got much more vulnerable with each other; we began to push each other; and I began to internalize the fact that perhaps the most important role I had was leading the management team. Overtime, the management team became, in my opinion, very high-performing and all members stayed with me through my tenure.

Not leading the management team was 100% my fault. I was unprepared to be an effective CEO and if I had prepared more fully I could have avoided some early mistakes. The only reason I survived is that I think every member of the team knew two things: (1) I was passionate about NSNO and (2) I was an extremely committed constant learner.

If people believe you care and they know you want to get better and they trust that you can get better they will forgive you when you fuck up.

Anyways, those were some hard things. I’m sure I got some of the details wrong. But, at the very least, that’s how they felt.