For two months now, Uber has been tainted by a string of controversies, ranging from charges of sexism to potential privacy violations to alleged intellectual property theft. Casual observers who haven’t followed the company closely in the past might be wondering: How, exactly, did Uber get here?

“This company is modeled in the image of this man, who for the past 40 or so years has been driven at most everything he does, whether that’s doing startups or competing against friends and family at video games,” New York Times tech reporter Mike Isaac said on the latest episode of Too Embarrassed to Ask. “Or, in the case of Uber, breaking or flouting regulations and laws, and Apple’s App Store regulations.”

Isaac penned a recent 4,000-word profile of Uber CEO Travis Kalanick, the “man” in question, for the NYT. He said Kalanick’s pugnacious personality served him well in life and business, but might not so easily work for one of the highest-profile business leaders in the world.

“When he was being videotaped and got in a fight with a driver, they got in a yelling match, said some people have to ‘take responsibility for their own shit’ and got out of the car,” Isaac said. “There’s a world in which you can defuse that situation by being empathetic with the driver and saying, ‘I know, I hear your concerns, man. I’ll give you this number, you can talk to someone.’ He just doesn’t seem to have that.”

“Imagine a CEO who can listen to other folks and meet them in the middle,” he added. “Or even if they disagree, you don’t have to just go to the mattresses right away and start fighting with someone. I think he thinks it’s a perception issue and if people would just understand Uber in the correct light, and weren’t so slanted against him, everything would be fine.”

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Uber’s board is still investigating the slew of of sexual harassment and discrimination allegations sparked by former employee Susan Fowler, and Isaac predicted that the top of the org chart will look different by the time it’s done.

“My read is that they have to have a head on a pike at the end of this,” Isaac said. “You have to fire at least one or two people to show that you are taking this seriously, and if they don’t, I will be shocked. Not just some offenders at the bottom — who at the top has been responsible for this?”

However, he predicted that Kalanick’s job is safe because he sits on that board alongside several people who have historically been his friends and defenders.

“If you say he’s accountable to the board, and he controls the board, he’s accountable to no one but himself,” Isaac said. “Outside of some serious accusations against Travis — and I have not found anything damning in my reporting — I don’t see them voting him out.”

“It would have to be something really severe — criminal, probably,” he added. “And even for Uber, ‘criminal’ means a certain level of severity, because they’ve arguably done some other things that have been against the law or up to the brink of the law.”

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