Reeves Wiedeman is a reporter at New York Magazine and the author of the new book Billion Dollar Loser.

“You get inside these companies and … you assume everything is running based on models and numbers and then you get inside and it’s just people. And sometimes they have MBAs and sometimes they don’t. … At the end of the day, whether you’re running a media company or an office space company, it’s all people making these decisions and they often do very strange, contradictory, and ultimately unsuccessful things.”

Thanks to Mailchimp for sponsoring this week's episode.