There Is Winning and There Is Learning
in 2020, I stumbled upon a company that I loved and got to work with people I loved, even more, doing work that I felt hopeful about. The company had some problems to solve, as all companies do. Some of the problems were big. I thought if nobody does anything, the company will fail and so when I was offered the position of CEO, I jumped on it without hesitation. I thought I could fix it, and I wanted to fix it because it was the most fun I have ever had working. I liked the problems and I was thrilled to solve them.
Almost every day that I was in this job, I watched myself grow. I have more pride in what I accomplished in the 2 years I spent as the leader of this company than in any other moment of my career. The thing is though, no matter how much I did right, I couldn’t save it. It didn’t work out and the company ended on my watch. All though that was a heartbreaking loss, it was also a learning.
I learned a lot about how to end a company, which was an awful but valuable experience. In learning that, I learned a ton about what kinds of things to tend to during the course of business that make ending (or selling) a business less complicated. I learned that even the best decisions, the decisions that minimize damage are often not the best decisions for everyone. I learned how to be all in. I was like 100% in all the way with my time, my mind, my heart, and my money. I learned how to lose and have a meaningful postmortem. I learned how to face a previously inconceivable amount of heartbreak and disappointment. I learned that just because I am hardwired to feel shame, doesn’t mean I should be ashamed.
While I am playing whack-a-mole with feelings of shame, for failing and letting people down, I am balancing my attention by looking at the undeniably badass accomplishments this experience afforded me. Here are my top 5 learnings:
If you don’t have enough money to weather a storm, you don’t have enough money. The fact is that I walked into an undercapitalized company. I restructured it, I rebranded it, I developed new products, I found ways to measure and track profitability, I cleaned up the books, I completely changed our relationship to our clients and massively changed our retention rates and none of it mattered. At the end of the day, we couldn’t get through market uncertainty because we didn’t have the cashflow to hold.
It’s important to care for the wellbeing of the team, but it is just as important to care for myself as a member of the team. Nobody was getting paid enough, and I as the CEO was not even close to the highest paid person in the company. I skipped paychecks and didn’t give myself raises in order to make ends meet. As a leader, I set an example and in this case my example was overcommitment and sacrafice. Business doesn’t deserve that kind of devotion. People work to make money and make a difference. If a business can’t afford it’s people (including it’s leaders and owners), it’s time to let go and let the natural selection of the market occur.
Don’t do it yourself. My blessing and curse is that I am a generalist that loves learning new things and I happen to be good at a lot of things. I had to learn to delegate more than I was comfortable with. I made massive progress in developing the sill of delegation andI suspect I have much more learning left. A coach once asked me what was more painful, watching people struggle with something that is easy for me or becoming the bottleneck by overcommitting to work. I know that there actually is a right answer here. There is a clear better path, but I can’t always choose it. This is probably going to be my life’s work.
There are many narratives that occur in a business, but the one with the numbers in it is the most important. There are so many great story’s to tell about my old company. There is the story about the mission and vision, the story about the impact we hoped to make, the story about the amazing people who worked there and the story about the hundreds of things we accomplished. Sadly the story that took too long to surface was the story about our money. It took a long time to get through the numbers to get that story in order. There was not a history of budgeting and cost tracking when I got there. By the time we were able to write that story, our fate was sealed in it. What a company does matters but it doesn’t matter more than how much resource it takes to do it.
Hire for the skills that are needed, don’t teach them. Like I said before, I am a generalist. I have done virtually every job in an agency. I am awesome at account management. I know how to run a creative team and how develop good creative. I can write a strategic brief. I am great on a sales call. All of that is true but it took me many years to learn it. There was no way I could teach people to be as good at those things as I am in a short amount of time. It would have been much better to hire people that were way better than me at those things.