It's this question that drew the actors to the Showtime's upcoming anthology series Super Pumped, which details the rise and fall of Uber founder Travis Kalanick and explores the ride-share app's impact on society.
Gordon-Levitt—who plays the disgraced CEO—was fascinated by Kalanick's success, despite all his shortcomings. "He made billions of dollars," the actor explained in an interview with E! News. "Why is our system rewarding that? Why doesn't our system reward companies that are looking out for everybody's well-being?"
He acknowledged that Super Pumped specifically pertains to the tech world, but asserted, "This isn't just Silicon Valley, this is how our system works right now. And I'm glad you're asking me about it because it's something we ought to be talking about because we're driving off a cliff unless we can change that."
And while the real-life story of Kalanick, as well as Chandler's character, Bill Gurley who was an Uber board member, played out in the news, it's hard to grasp how influential Uber was on society—at least, until you see Super Pumped.
Chandler described the series as "revelatory," adding, "I had no clue that all this had taken place. And I find that kind of stunning."
Going into the project, both Chandler and Gordon-Levitt decided not to reach out to their respective characters so as not to sway their depiction of these people. Chandler thought this was for the best, explaining to E! News in a separate interview, "Whatever I would have heard, I would have taken very seriously and it would have altered something. It would have became something that I'm not trying to do.
And while it's a "tremendous responsibility" to play someone who's still alive, Chandler didn't feel too beholden to accuracy. "This isn't a documentary, you know?" he shared. "It's a different way of telling this story, but no one's claiming that this is a documentary so I didn't need to go into that realm."
Gordon-Levitt went a different route, choosing to speak to those who knew Kalanick instead of the CEO himself. He felt this was "more informative" than reading articles or even the book the show is based on, saying, "What you see in the press is largely the questionable decisions he makes or has made and the questionable behavior that he's perhaps guilty of."
"What you don't get a sense of is what it actually feels like to have a conversation with him, to be close with him or be friends with him," he continued. "When I talked to people that were close to him, I got a much better sense of like, 'Oh, this is a big part of why he was so successful.' People actually really liked being around him. He's really convincing; he's really winning; like he's actually really inspiring in a lot of ways."
Gordon-Levitt thinks the same can be true of other notorious people, suggesting, "There's a reason why figures throughout history that are doing ethically questionable things get so popular—it comes from a certain energy."
Viewers can get a sense of just how charismatic Kalanick is when Super Pumped premieres on Showtime Sunday, Feb. 27 at 10 p.m.