Thinking Entrepreneur: Ten Years Later, An E-Mail From The Employee I Wanted to Forget

Thinking Entrepreneur

An owner’s dispatches from the front lines.

On paper, business is about marketing, management and finance. In reality, it is also about relationships: the good, the bad and the ugly.

If your business is growing, you are always adding employees. Some work out great, some work out O.K., some don’t work out at all. And some end in disaster. Those are the ones who can stick with you for a very long time. Among the hundreds of employees I’ve had over the years, there is only one that I have consistently avoided thinking about or talking about. And it’s not the one that you might suspect. It’s not the thief, the embezzler, the liar or the sexual harasser. It’s not the one that was laziest, most careless or most irresponsible.

In those categories, I have become numb. Or just experienced. I have learned that if you hire enough people, on your way to hiring a great staff, you are eventually going to go through all of those types. And I have learned not to take things personally (usually). If people steal, it’s because they wanted money. They were not necessarily out to get you. And even if they were out to get you, it comes with the territory. You are the boss. There’s something different about being the boss. To some people, it’s almost as if you aren’t really human. Anything goes.

But as I said, one person has stuck with me all of these years. About 10 years to be exact. I almost never talk about him; I can barely stand to think about him. It is not that he was the worst employee I ever had. He wasn’t. It wasn’t that he caused me the most grief. He didn’t. It isn’t that I am mad at him. I’m not. Actually, I have been mad at myself — or embarrassed with myself — for getting into a situation that ended badly. He probably only worked for me for six months. Like me, his father owned a picture-frame shop, and we both thought we could use the Internet to revolutionize the way custom frame shops advertise nationally. Like FTD. I hired him to start a new business. He seemed passionate and committed. To some extent, he reminded me of me.

Starting a new business can be intoxicating, and he became the entrepreneurial version of a drinking buddy. I treated him like my own. Of course, as I’ve written before, passion does not conquer all. The fact is, the guy was in his mid-20s, and I should not have expected him to spearhead this venture. I gave him enough rope to hang himself — not the only time I’ve made this mistake — and that’s exactly what he did. He was a kid, perhaps even a confused kid.

Things started happening. He was careless. He didn’t treat people well. We went to a national trade show, and he acted like a 14-year-old. I realized that he had to go. From what I remember, there was no ugly screaming (maybe a little). It was more like a sad divorce where the parties just go their separate ways. The business failed, through no fault of his. What seemed like a good idea wasn’t. If you look at my bio, you will see that I own five businesses. I have started 10. Failure is my friend. I have learned more from failure than I have from success.

So why am I thinking about this now? It’s not because I’ve been torturing myself. I’ve gotten better about that. I’ve made enough mistakes that indulging regret could be a full-time job. The reason I’m thinking about this is an e-mail — an e-mail I just got from this kid I hadn’t heard from in 10 years. He told me he was doing well, had gotten married and had a good job. He made clear that he expected nothing in return, not even a reply. He has been reading this blog, and he decided that he needed to send me an apology and an explanation. He wrote, in part: “I’m sure that you are less interested in how I’m doing than as to why I would feel compelled to write you all these years later. The answer is simple: I owe you. I owe you a more mature, more sincere apology. … I treated your employees and family disrespectfully. I was not ready for the gifts you gave me, the company credit card or the business that I proposed we create together. I was overwhelmed by the sudden acceptance and trust you gave to me and rather than build upon it, I acted to destroy it.”

At first, I thought that he must be in one of the 12-step recovery programs that send people back to apologize to everyone they have wronged. But I don’t think that is the case. And this wasn’t just any e-mail. It was a well written, eloquent, gut-wrenching e-mail. Clearly, this had been bothering him. Two of the sentences really hit a nerve: “You were not a fool. I was an …” — he used another word for jerk. “I’m sorry, Jay. I’m so, so sorry to this very day.” It’s not so much that I needed him to tell me that I wasn’t a fool — I was a fool. But his acknowledging that he had been a jerk and that he felt bad about it made a difference to me. It made me feel better.

As a matter of fact, I feel a lot better. I now realize that just because you try and fail with someone doesn’t mean you are a fool. It means you are a boss. There doesn’t have to be guilt, regret or any of the other things that human beings have to suffer. You can just move on and try to do better. In the last 10 years, I have also recognized that I’m an entrepreneuraholic. Now, I’m a recovering entrepreneuraholic. I no longer have to start every business I think of (I write for this blog instead).

So, to answer your question, I did reply to his e-mail. I thanked him, and I gave him a full pardon. He has grown up. And so have I. The fact is, he redeemed both of us.

Am I the only one who has had this kind of unfinished business?

Jay Goltz owns five small businesses in Chicago.

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