Of course, youthful wrongdoing is hardly destiny when it comes to adult rule-breaking, as Professor Levine, the economist, pointed out. While he was at Harvard, the Facebook founder Mark Zuckerberg was summoned before an administrative board over allegations that he had hacked into university websites. But he appears to have matured over time, even retiring the "move fast and break things" motto in 2014.
These days, many venture capitalists spend as much time assessing what kind of troublemaker an entrepreneur may be as they do assessing a business's revolutionary potential.
"We do want them to be rule-breakers," said David Golden, who helps run the venture capital arm of Revolution, the investment firm of the AOL co-founder Steve Case. "We don't want them to be felons."
Mr. Golden admitted, however, that such judgments can be flawed. He cited a software company that Revolution agreed to finance in 2014, only to discover that the founder had misrepresented certain companies as customers. (The firm did not go through with the investment, he said.)
To eliminate subjectivity, some people have tried to quantify an optimal willingness to break rules. Before he started his venture capital fund, Switch Ventures, Paul Arnold collected data on roughly 12,000 start-ups with the goal of identifying the profiles of entrepreneurs that were most strongly associated with success.
Mr. Arnold's most striking finding involved start-ups where at least one founder had worked at the consulting firm McKinsey & Company.
He studied nearly 1,000 such companies and discovered that start-up founders who left McKinsey after about three to four years tended to be extremely successful, but that those who stayed a lot longer were close to average. He concluded that the first group had the platonically ideal capacity for rule-breaking: They were sufficiently fluent in rule-following to hold a job at McKinsey but "didn't like the strictures and kind of resisted it."
But even Mr. Arnold, whose intuition on these questions was honed not just by statistics but by life experience — he was a two-time high-school dropout who was often in trouble for things like smoking marijuana before eventually finding his way to law school — admitted that he might have missed the warning signs with Mr. Kalanick.
While he was chief executive of Uber, the company developed a tool to evade regulators, had dozens of employees allege sexual harassment or discrimination, and was accused by a rival of stealing intellectual property.
"The Uber story is that the initial rule-breaking was innovation," Mr. Arnold said. "But it was a slippery slope. They broke the next one and the next one, and were doing less and less ethical things."
"I don't know," he confessed. "It's a tricky topic."
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This story originally appeared on The New York Times.