The time when I fired everyone

It was my exit interview. I was having dinner with the CEO of the company which I had just quit after only working there for only 9 months.

“If you were me Jimar, what would you do?”, I was asked.

“I would fire all of the executives,” I responded.

It wasn’t my most tactful response, but I was honest. I thought the company was being mismanaged. We had a well-engineered product — almost too well-engineered. It had so many features, it was very difficult to rationalize them. We had so few customers, we didn’t have any proof points to tell us where we should invest our time. We had a dysfunctional relationship between Product Development, Sales, and Solution Delivery.

I came into the company as the Director of Product Management. As a product manager, it was my job to get product-market fit. I had to rationalize the product we were building for our target market. I had to figure out how we can take our current successes and parlay them into future wins.

The problem wasn’t that the market wasn’t there, that we didn’t have enough money, that we didn’t have a product, or that we currently didn’t have sales; the problem was that we couldn’t get out of our own way.

Or maybe, I was the problem.

I had just come from an established company with well-defined processes, a well-defined and well-developed sales channel, and several decades of success under its belt. I was coming into a startup with none of that. What should I have expected? Wasn’t that the reason this company brought me in, to help bring in that expertise and build them up?

Maybe I was jaded, thinking about how much money I was going to make on stock options instead of focusing on the job at hand.

In the end, I realized that I was incompatible with that company, regardless of who was “at fault”. It wasn’t that they had a bad culture — I just wasn’t a culture fit. I effectively did what I recommended to the CEO — I fired “everyone” from my working arrangement by firing myself and quitting. I shortly started my own company.

Looking back, I don’t know if I would have made more money staying there versus starting HatchWork Solutions. But I was adamant about betting on myself, regardless of the cost.