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'Ignore Your Schedule': The Bad Advice that Ozy Media's Carlos Watson Gave to Entrepreneur

As Ozy's workplace culture is being publicly scrutinized, an old quote of his sounds very different.


"Ignore your schedule and win the moment."

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That's something Ozy Media co-founder Carlos Watson said to me in 2019, when I interviewed him for a short piece in Entrepreneur. The magazine had been asking entrepreneurs for traditional "rules" that they've broken, and when Watson proposed this one, it sounded like sharp advice from a creative leader. Now, as a raft of reporting has revealed Ozy's troubling work environment and business tactics, that line sounds very different.

It sounds like a leader who's unaware of how his actions impacted those below him.

Since its founding in 2013, Ozy has portrayed itself as an innovative and rapidly growing media company with a popular website, festival series, and multiple TV shows. Watson has been the face of the brand — hosting the shows, speaking on stage, and appearing in the many ads and billboards the company has purchased.

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But as New York Times columnist Ben Smith reported, much of the company's growth and success appears to have been fabricated. Among the alleged deceptions, the company's other co-founder, Samir Rao, impersonated a YouTube executive while on a fundraising call with Goldman Sachs. Ozy has since hired a law firm to "conduct a review of the company's business activities," according to The Wall Street Journal, and other media outlets are interviewing former Ozy staffers who describe an abusive work environment.

CNN reporter Kerry Flynn wrote about Watson's unpredictable schedule and habit of constantly rescheduling meetings, and the effect that had on his staff:

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.

As I read this, I of course flashed back to the conversation I had with Watson in 2019.

"As the founder of a young company, I know how hard and special it is to get the right people in the room," he told me then. "When that happens, you can't be so tied to your schedule that you're afraid to go deep."

The way Watson portrayed it, people are often so busy that they don't have deep and engaging conversations. So when he's in the middle of one, and he feels like it's productive, he'll keep it going — and sometimes even order in food — to treat it like an intellectual hackathon. "That's not always easy, and that's not always pretty, but it's the only way to get something to a full place of development," he said.

True to form, he even rescheduled the interview I did with him about rescheduling.

Many reports about Watson describe him as charismatic, and I can attest to that. I'd met him a few times before the interview, and always found him to be warm and engaging. He seemed animated by ideas and eager to build relationships, and he had a good memory for wherever our conversation last left off.

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I don't know him well enough to speculate about where he went wrong in business, but I think this much is clear: Whatever his ambitions were, his means of achieving them did not properly take other people — including his staff, partners, and investors — into account.

That is the downside of, as he said, ignoring your schedule to win the moment — and in retrospect, I wish I'd considered that before putting it in the magazine. Today, as the business community is speaking more about the importance of building strong and healthy workplace cultures, that downside is even more apparent.

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.

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