What Entrepreneurs Should Learn from John Lackey


Success in business is out of reach to those who aren’t already blessed with plentiful advantage, so goes the conventional wisdom. A similar stereotype in sports is that you either have talent or you don’t. But the story of a once-maligned pitcher’s World Series victory upends both of these stereotypes, and has great lessons for entrepreneurs.

A year ago, the Boston Red Sox would have gladly traded John “Popeye’s Chicken and Beer” Lackey for a bucket of dirty baseballs. Certainly, the fans would have. The pitcher delivered a horrific 6.41 earned run average in 2011, missed the entire 2012 season due to injury, and his clubhouse antics suggested a lack of discipline and focus that would hamper him even when he was healthy.

Fast forward to last month, where Lackey’s performance in the final, decisive World Series game led the team to victory. As Lackey walked off the field for the last time, the fans at Fenway Park rose in an enthusiastic standing ovation, and he finally tipped his cap to them.

How did he pull off this incredibly improbable redemption? Surprisingly, it’s the same reason that people’s economic background often fuels their success: hunger. But in this case, the hunger does not have to be economic, it can be hunger to prove others wrong and one’s self worth.

Red Sox pitcher John Lackey (Image: Barry Chin/The Boston Globe via Getty Images)
(Red Sox pitcher John Lackey tips his hat to fans after pitching a brilliant game that ultimately won the World Series for the Boston team this year. His relationship with the fans underwent a complete reversal in a period of 12 months. Photo courtesy of Barry Chin/The Boston Globe via Getty Images.)

“Desirable difficulties” is the term used by Malcolm Gladwell, in his new book David and Goliath: Underdogs, Misfits, and the Art of Battling Giants, to describe why a background, condition, or an event that would seem to decrease a person’s odds of success can actually increase their odds of success.

In Lackey’s case, that would have been his 2011 and 2012 seasons, compounded by Red Sox organizational woes during that time. For an entrepreneur, as Vivek Wadhwa showed when he interviewed 549 founders for the Kauffman Foundation, it is coming from humble beginnings—as opposed to having a lot of money in the bank—that pushes them to be great entrepreneurs. Why? Because entrepreneurship requires focusing on a singular goal while avoiding distractions, which requires intense self-motivation. Focus is absolutely crucial to a startup because you have very few resources—working capital, manpower, and time are all at a premium. Locking down on a single target market and product is the only way to effectively leverage your limited resources. And to succeed, you need self-motivation to keep you going through the challenging moments, since entrepreneurs do not have bosses or authority figures forcing them to do their homework.

And self-discipline is even more difficult when you are comfortable—whether it’s a large bank account or an adoring fan base celebrating your successes. “It is hard to be an entrepreneur on a full belly,” as my MIT colleague, Professor Bengt Holmstrom, puts it. That metaphorical full belly can be economic or feelings of self worth. It doesn’t hurt to have a few demons around sometimes.

After all, why choose the challenging career path of entrepreneurship if you already have a well-paying job at a large corporation, or have a lot of money saved up and you feel great? In Lackey’s case, the motivation could be higher to focus on pitching fundamentals when you are doing well enough and it feels like the fans and the city are against you. Some people can harness this crisis to create extra energy to fight back. In doing so, they instinctively understand that they need to pursue a path of immense self-discipline and focus.

But it’s not just about having a chip on your shoulder. I believe John Lackey had a constructive chip on his shoulder, in that he was willing to buckle down and focus on what he needed to in order to be successful. Compare that to his former teammate Josh Beckett, also of chicken-and-beer infamy, who I believe has yet to constructively funnel his energy, and has seen his career stall as a result.

Denzel Washington’s character from Remember the Titans perfectly nails this dichotomy when trying to motivate the football team he coaches: “You got anger, that’s good, you’re gonna need it; you got aggression, that’s even better, you’re gonna need that, too. But any little two-year-old child can throw a fit! Football is about controlling that anger, harnessing that aggression into a team effort to achieve perfection!”

Such is the playbook for entrepreneurs—balance. Take your adversities and use them to create greater drive and focus, but do not lose control. And when in doubt, ask John Lackey, or just take a look at that photo of him tipping his cap, and feel the accomplishment of greatness by a man whose talent was strong, but whose drive to succeed was stronger.

Bill Aulet is the managing director of the Martin Trust Center for MIT Entrepreneurship and a senior lecturer at the MIT Sloan School of Management. He is also the author of “Disciplined Entrepreneurship: 24 Steps to a Successful Startup”, published by Wiley, which was released in August 2013. Follow @BillAulet

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