What Start-Ups Can Learn From a Crime Boss

Kyle KestersonDonald DeSantis

What lurks in the hearts of mild-mannered software developers? Donald DeSantis’s answer may surprise you. The 29-year-old Seattle techie recently penned a tale of unlikely inspiration called “Everything I need to know about start-ups, I learned from a crime boss.”

The short manifesto, published at GigaOm, probed the underbelly of leadership and set readers aflame, provoking thousands of Twitter comments and direct responses. Some comments were positive and others told Mr. DeSantis he should be ashamed for loosening “the moral fiber of young entrepreneurs.”

The piece begins: “The door opened and into the room walked the most dangerous person I’ve ever met. He reached toward his belt and slowly pulled out his .45 caliber handgun, raised it and paused to evaluate my expression. ‘No disrespect, but it’s been pressing into my hip all day.’”

Introducing the organized crime figure and mentor he identifies only as “Kobayashi” — “I’m a Usual Suspects fan,” he explains — Mr. DeSantis goes on to attribute to his teacher such lessons as “Don’t Sell Rocks when You Can Sell Mountains.” Kobayashi, according to Mr. DeSantis, also stressed the importance of networking and acting decisively: ” ‘Closed mouths don’t get fed,’ he would say. ‘If you want something, you have to either ask for it or walk up and take it.’ We can’t expect good fortune to fall into our lap. It’s our responsibility to create the circumstances for it and then capture that good fortune. The meek may inherit the earth, but they’ll be getting it from Kobayashi.”

Mr. DeSantis works at a four-person social-video start-up, Giant Thinkwell, which closed a $600,000 round of seed funding in April. He’s also an organizer and speaker for Startup Weekend events around the globe.

“I don’t think that he’s read it,” Mr. DeSantis said of Kobayashi during a phone interview. “I haven’t spoken to him in years, but obviously the impression he made is lasting. I’d hope he would feel somewhat flattered.”

Mr. DeSantis declined to disclose details of Kobayashi’s, err, revenue streams. If there’s a theme to Kobayashi’s teachings, Mr. DeSantis said, it’s to be a charismatic and self-disciplined leader. “It’s not like ‘Be a bad person,’” he said. “I’ve had an opportunity to work for some really amazing people, where the world just gets out of their way and reorganizes itself behind them.”

Whether we’re seeking wisdom from Kobayashi or Mother Teresa or the Shackleton Expedition, business-oriented humans seem to react strongly to lessons from unconventional characters and incongruous contexts.

Have you learned from people and experiences outside your professional sphere? If so, what are your most unexpected sources of influence?