I usually enjoy Kevin O’Leary and when I don’t agree with him, I at least find him entertaining and thought provoking. But he recently waded in on something that I find concerning because of my experience in early stage tech. He decided to start talking about Australia’s recent right for employees to disconnect outside of business hours and made some highly questionable points.

In a recent Fox News interview about Australia’s right to disconnect, O’Leary raged:

“What happens if you have an event in the office and it is closed? Or you have an emergency room somewhere and you have to get of hold of them at 2am in the morning because it affects the job they are on.”

Then he took to X and doubled down, writing:

“If you can’t be reached when the job depends on it, you’re out. Who dreams up these ridiculous ideas? If someone tells me they’re in ‘silent mode,’ they’re fired.”

If someone in my leadership chain had a similar point of view, I would fire them immediately. Because you see, while it’s fun to make political points, my job is to build a really good company that can live for longer for me. Therefore, I cannot have single points of failure and I cannot tolerate a business structure in which I need to call any individual at 2am. If a business has a point of failure so extreme that it could bring down jobs in the middle of the night, it is a sign of shitty leadership. So, fire the entire C-suite but leave the person alone at 2am.

Why?

Because good people have a lot of options and fundamentally, if my business is where someone else builds their career and moves on, that’s a great thing for everyone involved. But there’s also a darker side. We live in an unpredictable world where there are natural disasters, accidents and sudden deaths. Consider what happened in Jasper the summer of 2024. Jasper is a stunningly beautiful place with an incredible sense of community. Or rather, Jasper was a stunningly beautiful place because a lot of it has burned to the ground. Nobody planned to lose their homes and have to flee in the middle of the night. But our businesses still have to function when the worst happens. We have clients to serve and our people still need jobs.

Therefore, if this ‘right to disconnect’ bothers you, maybe you need to take a look at the business structure you created. Why do you depend on that one person and what happens if they get hit by a bus? On the other hand, if your employees having a life and interests outside of your company causes you psychological discomfort, maybe you need to take a look at the kind of human being you are. There’s nothing inherrently capitalist or noble about being unreasonable with your people - it’s most likely that you’re just bad at managing resources.

Every management problem is an opportunity to look deeper into yourself and decide if you’re creating a more toxic environment. If you are, it’s your job to manage to fix that.

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