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.

“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 at MIT, as well as a senior lecturer at the MIT Sloan School of Management and author of “Disciplined Entrepreneurship”. Follow @BillAulet

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11 responses to “What Entrepreneurs Should Learn from John Lackey”

  1. Bill, I loved the analogy you made to Lackey. Wadhwa’s study also rang very true for me as an entrepreneur. When you grow up with no safety net (as I did), and you start a company also in that state (no one is going to bail you out, I had no meaningful bank account), you are 1000% more driven and self-reliant. Oddly that “lack of choice” and having nothing to fall back on is like precious fuel, with a nearly bottomless supply of drive and ambition.

    I always find it odd that investors can gravitate to the “hail good fellow well met” profile (as one VC told me is their preference). Those people have other solid options and comfortable alternatives, and have not proven that they will keep going when the going gets tough. In my case, I never expected building a startup to be easy…nothing else in my life ever was…so that made me a heck of a lot more bankable!

    • Bill AuletBill Aulet says:


      You got it! Interesting how research shows that VCs have other biases as well — see http://www.bostonglobe.com/magazine/2013/11/02/how-female-entrepreneurs-can-get-venture-capital-game/Ahn0XfhG3WABm8Q4uoAq6O/story.html — specifically women.

      This was a real fun article to write and I hope it has impact and creates more people like yourself. Entrepreneurship is the ultimate meritocracy.


      • Bill, unfortunately that Boston Globe article pissed off just about every credible female entrepreneur in town….there is better research and writing on that topic that won’t place the burden on the victim. (Wadhwa’s work alone is a good go-to place. Thanks for pointing him out to the Xconomy crowd.) The Globe author you cite did, in actuality, make it clear that most of the bias issue is on the VC’s themselves, but her more prominent advice/prescription in the piece is what really got women mad: basically she said “be more like a guy”.

        I do agree that entrepreneurship is the ultimate meritocracy if you are a white guy or want to build a lifestyle business that needs little capital. The rest of us have to “make do” with the 4% of PE and VC crumbs that fall off the table. Of course, not all successful (or even giant) businesses need those sources of funding at origination, but when they do, that 4% stat (new, out of Stanford) is so so damning.

        However, I am happy to see that those same populations that struggle to get VC/PE attention have great success in the meritocracy of crowd funding. This is starting to be a real source for venture funding. I like what Launch Angels is doing in that arena, to make crowdfunded equity investments.

        • Bill AuletBill Aulet says:

          You have peaked my interest further, what are the numbers for crowdfunding and women? It has to be better than the track record with VCs. This could be and important avenue to get to a better pure meritocracy.

          • Women succeed at securing 41% of the funding on crowdfunding sites and have a slightly higher success rate in getting to completion of a funding goal than men. Women get 11% of angel funding BTW. 4% of VC.

  2. Bill AuletBill Aulet says:

    The Pats followed this model after getting booed in the first half last night too

  3. Bill AuletBill Aulet says:

    Thank you for the data, very interesting. What is the source so I can use this data as well?

  4. Bill AuletBill Aulet says:

    I have been impressed by the response to this article from people and wish all the dialogue had been on line. It has been fascinating.

    One highly accomplished CEO said this is exactly the kind of motivation that made him what he is today. People kept telling him he couldn’t get done what he dreamed and it just fueled his fire even more. In fact even today (much like Tom Brady is fueled by the QBs who were chosen before him when he was chosen at 99 in the draft), this CEO says “I know the names of all 36 venture capital firms and the 50 plus partners” who turned him down and told him his company would not work. He channels this into energy to take his company to even higher levels of success.

    Another former student, Erdin Beshimov, pointed out “I’d rather be rich and hungry. But if I can’t be both, I’d rather be hungry” which summarizes a key point of the story well.

    Paul English wanted to know if it was really true or simply an American fable about entrepreneurs coming from modest backgrounds. While the recent Unicorn report casts some doubts on this for the $1B software companies in Aileen Lee in TechCrunch analysis (which not to discount Aileen’s contribution nor intellect, we should note was not peer reviewed nor done by a trained social scientist), the earlier work done by Prof. Ed Roberts made clear that immigrants start companies at a higher rate than non-immigrants. The assumption then is that immigrants have more modest means but technically this loop needs to be closed and more work done on this question.

    But glad the article has stirred up such robust discussion. I think it is a great topic.


  5. Bill AuletBill Aulet says:

    This just in from someone else. Jack Parker was the legendary hockey coach at Boston University who just retired after a 40 year Hall of Fame career — “Jack Parker of BU fame also said that over the
    years the guys who made it to the pros from his program were the ones that
    “needed to make it”. “

  6. In this context I would like to mention a Hindi movie Chake De based on Hockey. The movie is inspired from the life of a former Indian Hockey goal keeper. India lost the Asian games final to Pakistan in 1982 and Mr Mir Ranjan Negi was the goal keeper. He was vilified for the loss. He returned as a goalkeeping coach for the 1998 Asian Games in which the Indian National Hockey team won the Gold.Subsequently he became the coach of Indian Women National Hockey field team who won the gold in 2002 Commonwealth Games.