4 Lessons Entrepreneurs Can Learn From the Cubs’ 2015 Season

3 min read · 6 years ago


The Chicago Cubs aren’t just a local phenomenon anymore — they are taking the country by storm. As someone who lives two blocks from Wrigley and has season tickets sitting with my “Cubbie family” in right field, I’ve watched the Cubs rebuild with no small amount of baseball interest. Even more than that, as an entrepreneur, it’s been a fascinating business to watch being rebuilt. I’ve learned at least four key lessons from this team that I’ll always remember professionally, that I believe other entrepreneurs and small business owners could learn from as well.

1. Talent Trumps Experience

This team is one of the youngest in baseball, with an average age of 28.3 years. But beyond the statistics, many of their most important performers weren’t playing in the big leagues last year. Young guys like Kris Bryant, Kyle Schwarber, Addison Russell are brand new to The Show and performing at an incredible level. They credit “playing dumb” and a willful unawareness that they are trying to achieve the impossible. Similarly, entrepreneurs are generally under matched, under-resourced and less experienced, but need to “play dumb” to achieve the impossible anyway.

2. Keep Grinding and the Tides Will Turn

Besides the young stars, a lot of the other key contributors to the Cubs’ current success were given up on at various points in their careers. Jake Arietta is having one of the greatest pitching seasons in history just a few years after he was traded away from Baltimore for almost nothing. The Cubs are full of other players (like Starlin Castro, Javier Baez, Trevor Cahill and even Anthony Rizzo) who have risen to the occasion on the greatest stage after going through all kinds of trials and tribulations. You’ll rarely find an entrepreneur who hasn’t gone through those times when they felt like they didn’t belong in the Big Leagues of business. But the key for them as well is to keep pushing through.

3. Ignore the Critics

Focus on leading, not lagging indicators. Just ignore the critics. Over the past few years as the Cubs rebuilt, management and ownership have been ridiculed by impatient fans. Their management focused on the leading indicators, primarily their “years of control” of talented players along with progress being made in the minors and the farm system. It took time and courage, but by not abandoning the plan they put themselves in an incredible position. The same holds true for business owners. Stay focused on the direction and leading indicators, and don’t get sidetracked by games lost in the past or by second-guessing yourself.

4. Don’t Let the Pressure Exceed the Pleasure

Since the new manager Joe Maddon was hired, he reminded the players that they are playing a “kid’s game,” and to have fun and play loose. He’s consistently preached that he doesn’t “vibrate at that frequency” when the press asks about the weight of history bearing down on his shoulders. By keeping his team loose, he has avoided the internal pressure most professional athletes feel and put them in the position to succeed. Similarly, entrepreneurs tend to internalize tremendous amounts of pressure and forget that most of us are pursuing an opportunity that the rest of the world can only dream about.

It’s a blast watching these talented hitters knock home runs out of the park. But for me, it’s even more amazing to view this team as the embodiment of a variety of timeless management philosophies.

Erik Severinghaus is the founder and CEO of SimpleRelevance, a Chicago-based company focused on digital marketing personalization. Prior to that he received a patent while in IBM‘s IT Optimization organization, and helped co-found iContact – a leading Email Service Provider.

BusinessCollective, launched in partnership with Citi, is a virtual mentorship program powered by North America’s most ambitious young thought leaders, entrepreneurs, executives and small business owners.