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Kyle Scott/Handout

“I was always pretty sure I wouldn’t run Top Hat forever. Some people really have an ego about being a CEO. I don’t. For me, it’s just more responsibility and a lot of stress. As a business starts growing—if you’re fortunate enough to have some growth—the demands on the CEO rise exponentially, and it comes down to your ability to keep pace. At every stage, the stakes go up. At the very beginning, the question is, can you survive for a year and raise money and build the first version of the product and get your first customer? At the scale we’re at now, the question is, can you add another $30 million or $40 million to your revenue this year? Your reward for successfully navigating each level is to have an even gnarlier problem to tackle.

I was also never interested in running a public company, which means spending more time doing things I don’t really enjoy, like investor relations and being very external-facing, and less doing the things I enjoy, which is focusing on the product and operating the business. And your successes and failures are very public. You’re not just considering what the right thing to do is; you’re also considering what’s going to be the right thing optically.

So stepping down was just a question of timing. The pandemic probably delayed my decision by a year. Things were really crazy, and I couldn’t imagine trying to do a change of leadership, too. But six months in, things got a bit more stable. And in February, we raised another US$130 million with Georgian Partners. We also made a bunch of organizational changes to make the business more robust. I just sort of felt like, okay, if I do hand over the reins, Top Hat will continue to grow.

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My successor, Joe Rohrlich, had led a software-as-a-service business that saw tremendous growth. It also grew through acquisition, which is really valuable experience for Top Hat, since that’s a big part of our growth strategy. Joe started in March, and I’m planning to stick around in the near term to support him and make sure the transition is smooth, and to do anything I can to make sure he’s successful. I mean, I’m staying on the board, and I’m still a big shareholder—I wanna make sure my shares continue to accrue value.

It will be hard to see a problem I would solve in a certain way, and not be able to jump in and make that final decision. But anything that’s sufficiently good or bad will end up on Joe’s desk. He’ll be the one in the hot seat.

This is a really personal decision. You’re balancing what’s good for the business and shareholders, and the personal interest of the founder. It’s rarely a clear-cut decision. Sometimes things are going amazingly, and the entrepreneur can see themselves running the company for the next 20 years. In other cases, it’s a dumpster fire, and the board has to step in. But most cases are in between. If things are going well generally and you want to stay on as CEO, you should. That’s one of the privileges of being an entrepreneur. Maybe there’s someone who’s slightly more perfect for the business, but the fact that you founded it gives you priority to take the opportunity to learn and develop, rather than being swapped out as soon as there’s someone 10% better.”

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