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Apologize Before You Have To: My (Small) Role in the Ozy Media Collapse

I published some bad advice in 2019. It became unforgivable in 2021. Here’s what I learned when I apologized.

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We all make mistakes.

Our first impulse is to hide them, because we want other people to see us as trustworthy and capable. But last week, when I admitted a mistake that I made, I discovered that the opposite is true: Proactively admitting our errors actually builds trust.

Why? Because we’re all human. Everyone is going to mess up, which means everyone is going to expect everyone else to mess up. To be at ease with the people around us, we want to know how they deal with the inevitable missteps.

Here’s the story of my recent mistake and what I learned by admitting it.

Did you hear the one about Ozy Media?

In 2019, I talked to Carlos Watson, the founder of Ozy Media, for a package in Entrepreneur magazine about how leaders break rules to succeed. Watson’s rule-breaking insight was to “ignore your schedule.” When he found himself in important or fruitful conversations, he said, he would extend them as long as felt right, even at the expense of whatever other meetings he had.

At the time, this struck me as a handy little nugget from a successful guy. Ozy was reported to have massive traffic numbers, plus a bunch of popular TV shows and podcasts. Why not learn from the guy at the top? We put his tip in print.

Two years went by. Then all at once, Ozy’s “success” looked very different.

Last week, Ben Smith, the media columnist at the New York Times, revealed that Ozy’s success was a sham. After Ozy had a co-founder pose as a YouTube executive on a fundraising call with Goldman Sachs (eek), it came to light that their traffic numbers didn’t correspond at all to the amount of engagement they were getting (has anyone ever said to you, “I just read this Ozy article”?). Meanwhile, Watson, a super charismatic talker, was apparently using those fake numbers to secure vanity TV and online video projects.

Here’s where I recognize my (small) role

In the wake of the Ben Smith piece, Kerry Flynn from CNN reported what a challenging workplace Ozy had been for the staff under Watson — precisely because of his “ignore your schedule” philosophy.

Weekends were not typically for rest at Ozy. Sunday meetings were a regular occurrence. Prior to the pandemic, these meetings were in-person at the office in Mountain View or sometimes required staffers to go to Watson's home.The time of the meetings was described by former staffers as a moving target. One former staffer recalled a typical kind of thing that would happen would be, for example, that just five minutes before a meeting was supposed to begin, Watson would push it back two hours — and then still end up being 20 minutes late.What was an hour of your Sunday then turns into like four hours of your Sunday because you have to be around and be available that whole time," the former staffer said.

That sounds terrible! Looking back, I can’t imagine what these people must have thought as they ground it out at this company with an insane schedule, and then they flipped over to Entrepreneur and saw us praising their boss for making their lives miserable. Truth be told, I didn’t think about the staff’s perspective when I published the piece. I should have.

I think part of why I didn’t is that, frankly, Carlos was so nice (not a good excuse, but if we're being honest...). I’d met him a few times, and I liked talking to him, and that comfort released me — and, it seems, a lot of other decision-makers — from interrogating why we’d never really come across Ozy outside of the times its publicists got in touch.

Last week, when I realized that I had contributed to boosting and legitimizing Ozy’s profile, I started to feel uncomfortable.

So what did I do?

The magazine spot we published was tiny, maybe 150 words. Everyone has probably forgotten it by now. But I think we all must be aware of the role that we play in perpetuating false stories, no matter how small.

So although I was tempted to let it fade, I decided to acknowledge my part in enabling a destructive work environment — and, you know, a big corporate façade. I wrote a mea culpa on Entrepreneur.com, to the tune of: “Yes, we all must build flexibility into our days. But great leaders, and great builders, make decisions while being alert to the impact they have on others. They understand that other people’s time is as valuable as their own — and they earn those people’s time, rather than constantly expecting it.”

The response has been great, and actually really instructive. Here’s the comment that really made me think:

Apologize Before You Have To: My (Small) Role in the Ozy Media Collapse

The takeaway

We do our best to not make mistakes, but they will happen anyway. And when they do, we naturally worry about admitting them, however small. But what Rileena’s comment shows is that by and large, when we admit error without being forced to, we build trust.

Of course, we all need to apologize when we’re asked to. But when you proactively admit your errors, you reveal to your audience, clients, and whoever, that they are in good, human hands with you. Human hands that will make mistakes. Human hands that won’t always be as nimble as they could be. But if you admit that you were wrong, then people know that you hold yourself accountable — which means that the burden won’t fall as much to them.

Not to mention, it felt good for me to get this off my chest — certainly better than feeling silently uncomfortable and hoping no one would bring it up. Maybe that in itself is enough.


Are Simple Things Ever Simple? Nah.

The history of knitting is long and controversial — and includes many of today’s most hotly debated topics. (Sexism! Conspiracy theories! Fears of automation!) In the latest episode of my podcast, I explore knitting’s surprising past, and what happens when one knitter tries to make change today. Take a listen!

Apologize Before You Have To: My (Small) Role in the Ozy Media Collapse