The Guilt of Selling

After being a bootstrapped company for more than ten years, it came as somewhat of a shock to find ourselves discussing the possibility of being acquired. It wasn’t so much the tiny boardroom in the middle of Utah where this conversation took place that was the foreign part, it was the situation all together. You see, we weren’t actively looking to sell the company. In fact, we were growing year over year and we loved coming in to the office each day. However, when the acquisition call comes in, you have to answer it. And that’s exactly how Scott Skinger, founder of TrainSignal and myself, president of TrainSignal, found ourselves in a one-on-one with Pluralsight executives and board members last April.

In the meeting, we spent the day talking about our respective companies, our achievements to date, recent projects, and future direction. We started discussing details revolving around our revenue, expenses, and individual departments. After a few hours, we realized that we had a lot in common and we were trying to achieve a shared goal; to provide affordable, valuable, and educational content to IT professionals and developers worldwide. In hindsight, having this common platform was the key to a smooth transition.

After leaving Utah and heading back to Chicago, I could sense that the deal was going to happen. I started mentally preparing to accept the fact that something I helped build was no longer mine to control. My stamp on things at TrainSignal would no longer be a part of my day-to-day. As if that wasn’t enough to process, I started wondering how our employees would take the news. I started speculating on who Pluralsight would keep, and who they would let go. It was a roller coaster of excitement and anxiety, ups and downs.

In May, we agreed on the initial terms of the deal and due diligence began by accountants and attorneys. While I knew this would not be an overnight process, it was wrecking on me to go into the office each day knowing that we were in the process of selling, but nobody else knew. I would sit there in meetings and be present for kick-offs knowing it would all mean nothing in a few months. The guilt mounted when I found out who was going to lose their jobs as a result of closing the deal. At that point, I just shut down. I started avoiding the office and declining meeting invitations. The lying, deception; I just wanted it all to be over.

A few years ago, I always thought about how great it would be to build a company that eventually got acquired. Isn’t that every small businessman’s dream? I pictured all the employees celebrating with champagne and party hats. But such was not the case for me. All feelings of excitement were overwhelmed by guilt; a brick that I can still feel in my stomach to this day. Ultimately, I keep repeating that mantra “It’s just business” and I try to remind myself that this was the best decision. But rest assured, none of that changes how I feel about being acquired.

Nothing could prepare me for the day we told the news to the company. In addition to delivering the news of the sale, we also had to let go of about 25% of our team. While we gave substantial bonuses to everyone (even those whose last day it was) and full severance, none of the consolations compared to the guilt of selling. Even though I won’t soon forget this difficult day in my professional history, I look to the future – and to new experiences – for the closure I so badly covet.

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