Celebrity CEOs are amazing. Until they backfire. | Anna Butrico

CEOs are certainly important for the organization that they lead. We all have heard the stories of the larger-than-life CEO whose own name and brand transcends the company that he or she is representing. This is exciting because you see their names on headlines. You see them with a big following. People are interested in leaning in, wanting to know what this big personality is going to say next, and what their organization is going to do next.

But there's a big question here of the role that that CEO plays within our culture, in establishing how that product, that service that they represent, will service the nation, will service other nations, and the world at large. I think about larger-than-life CEOs like Steve Jobs, like Jack Dorsey, like Elon Musk. They have a platform, and I would argue then a responsibility to stand upon it and look at how their products, how their personalities, how their contributions are affecting the world and the discourse about the future of tech, the future of work, and the future of how we interact at large.

Steve Jobs in particular fascinates me. He could be direct, he could be mean, but he could be very focused and specific about what he wanted and the excellence that he demanded of his people, and in doing so, he created something that was unlike anything anybody had ever experienced. He really thought that the beauty was in the simplicity. The iPhone is just a simple little black rectangle that has changed how we communicate, how we talk.

STEVE JOBS: Our goal, and we think what serves the customer best, is to constantly be working on making things better.

ANNA BUTRICO: Though a complicated character, he elevated these questions of how the form of the things that we consume influences how we live and work with them. A CEO has great opportunity to elevate the brand of a company, to really put it in the public eye and make people really trust in the brand that they're buying.

But they also have the opportunity to do the exact opposite. The risk you run is when that personality, that brand of the person, is bigger than the brand of what the organization as a whole aims to achieve. Leadership is important; don't get me wrong. But when leadership steps on the company, when leadership contradicts what the company wants to do, then you have a bigger problem.

I'll start with Patrick Byrne, who was the CEO of Overstock.com. He was a very impressive leader. He had three degrees. He had a long history at Overstock.com. He had helped them go online. It was really in the most exciting part of the business that it had ever been historically.

He ended up having a private blog where he would talk about the earnings, where he would foreshadow new developments within the company, but he would also start to talk about some conspiracy theories that he had about himself, about his role as Overstock.com CEO and how that interacted with the government. He believed that he was tied up into a political scandal that would be a hundred times bigger than Watergate, as he said. He said that a Russian spy was intimately involved in his life.

The stock of Overstock.com crashed because people said, "Who in the world is the CEO and what is he saying? And what does that say about the Overstock brand?" The other one we think about is Elizabeth Holmes from Theranos. They created this new blood testing technology that was really fascinating.

What we found though is that Elizabeth Holmes was a bit deceptive in the science, that Theranos technology didn't work. They had a very easy, accessible result of a test that they would use with investors, that they would use publicly to say, "Look, our technology works," when behind the scenes, it didn't. She very intentionally took her board of directors and made sure that none of them were scientists. Some of them were former MDs. A lot of them were policy officials. None of them really knew much about the specific blood testing technology that she aimed to create.

So she went completely unhinged in how she was advocating for the technology; she'd fire anybody who stood up to protest it. When selecting ...