Secrets to Theo Epstein’s Success Extend Beyond the Cubs

Spend even five minutes watching a national Cubs broadcast and you’re bound to get a look or two at the lead architect of the team’s rebirth. And while discerning fans know that Jed Hoyer, Jason McLeod, and many others have contributed mightily to the success that’s been so evident at Wrigley over the past few seasons, there’s no denying Theo Epstein’s status as the alpha in Chi.

Realization of a shared goal is a strange thing, whether you’re intimately involved or experiencing it from the inside. As I fan, I can tell you that I often approach competition with a healthy dose of anxiety. I hate losing more than I love winning, so I’m never really happy until the clock hits zero or the last out is recorded and my team is ahead. But I’ve noticed something changing lately.

While I’ll never be willing or able to strangle the last breath from the lungs of my inner fan, this process of “covering” the Cubs has imbued me with an objectivity I had never imagined myself capable of. Maybe it’s just a matter of age, maybe it’s a defense mechanism. Or maybe it’s a desire to bring you stories and analysis of this team we love in a manner that entertains and enlightens without belying my personal loyalty.

I am Evan’s maturing sense of journalistic sensibility.

Just like you can’t miss the cutaways of Epstein in the stands, you’ve no doubt noticed the difference in Cubs Insider’s appearance of late. I’ll spare you all the gory details, but suffice to say a few separate bloggers put our heads together with a goal to provide better, more varied content than what any of us could hope to produce on our own. The funny thing is, I’m not sure I really expected it to work as well or as quickly as it has.

Too often, the best-laid plans end up as a road to nowhere in particular. You wake up to find that the highway you’re paving just dead-ends in a one-stoplight town where everyone looks at you kinda funny because you ain’t from around here. You’re a kid at a 3D movie, reaching out to grab that object floating right in front of your only to realize the moment you take your special glasses off that it’s just an illusion.

Except sometimes it works out.

When Theo Epstein came to Chicago, he did so with a plan and a crew of like-minded folks who wanted to turn things around. As he had learned from his time in Boston, when he was thrown into the deep end of the pool as a 28-year-old with “zero management experience, very little leadership experience, no business school training or principles at all about how to manage,” it’s nice to have people to throw you a life preserver.

Speaking with CNN’s David Axelrod on his podcast, “The Axe Files,” Epstein went on to further explain his philosophy for success.

“Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don’t like,” the Cubs’ baseball boss opined. “So if you can ask them or figure out what that 20 percent is, and figure out a way to do it for them, you’ll make them really happy, improve their quality of life and their work experience. If you do a good job with it, they’ll start to give you more and more responsibility.”

Man, that’s so true. I don’t care what line of work you’re in or what hobbies you have, there are certain parts of them you only slog through out of necessity. Take Cubs Insider, for instance, and the setup and maintenance of the site. Early in the process of running this bad boy on my own, the blog theme we’d been using was updated to something that was wholly unacceptable, forcing me to rebuild everything from scratch on the fly.

The halting, painful process that followed taught me a lot  about putting a site together, but it also proved to me that I am much better off just writing and editing (some of you might prefer I avoid that too). So you can imagine my excitement when a few other individuals, each with varying strengths and weaknesses, approached me about working together. The key to all of this, of course, is having an understanding of exactly what each of you brings to the table and knowing what the goal is.

Epstein began his Cubs tenure in much the same manner, by assembling his baseball staff and getting them all together to make sure everyone knew the deal from the ground up. It wasn’t evident to everyone on the outside at the time, but it’s so plainly obvious now how impactful aligning the efforts of all parts of the organization has been. Rather than a disparate series of fingers, the Cubs have formed a pair of fists with which to beat down their competition. Metaphorically speaking, of course.

In order to make this all work, though, you’ve got ensure that there’s a relatively singular identity. Uniting people of different temperaments, talents, and convictions in pursuit of a common goal will yield great results, but it’s not always easy. Which is why the Cubs have stressed character in their assessment of both players and staff members, seeking out those who can leverage their ability while pushing through difficult times.

“Failure is inherent in the game,” Epstein said. “So if you don’t respond well to adversity, you’re probably not going to have a long career.”

Reminds me of the time I nearly quit this gig after accidentally altering some code and breaking the previous version of Cubs Insider. Or when we exceeded the visit limits of our hosting agreement and sat by as the site slowed and eventually crashed. That was awesome. It was also temporary, alleviated by a few phone calls and emails and a more expensive contract. Huh, kind of like signing Jon Lester.

This wasn’t intended to be a commercial for CI — I mean, you’re already here — but I couldn’t help but see the parallels once I started writing. I look at what we’re building here and at what the Cubs have put together and I feel really good about both. It is my hope that, just as you see a well-rounded product on the field, you’ll be able to come to this site for all manner of information about and discussion of said product.

Here’s the thing, though, and you can go ahead and click back to the main page now if you want to skip this commercial: none of this is possible without revenue. Sure, we could run a bare-bones operation or run this thing at a personal loss (which I did for a while). But just like there’s a reason you see more signage at Wrigley and more legacy partners being announced, we’ve got to have ads to be able to afford things like a more robust hosting agreement and trips to various Cubs-related events and such.

And because man cannot survive on Google AdSense alone, we’ve also got some t-shirts that aren’t entirely awful. There are several new designs that have been added recently, so check out the shop and see if there’s anything that makes you want to part with a few dollars. If you prefer more traditional garb, we’ve got an affiliation with Fanatics that kicks us back a portion of your purchases.

In closing, I just want to thank you again for your patronage and your patience, and I hope our success here can produce even the most rudimentary facsimile of what Epstein and his philosophy have borne out for the Cubs.