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25 Entrepreneurs Learn from the Chicago Cubs

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Spring training is here and baseball is back. The Chicago Cubs pulled the improbably last year by stopping the curse. There’s always parallels between sports and business. We asked some entrepreneurs and business owners what they learned from the Chicago Cubs.

#1 – Overnight Success

Image Credit: Rodney Fife

If the Cubs were a startup or an entrepreneur they would be considered a overnight success. The long hard work of 108 years would be forgotten in an instant. Those entrepreneurs who end up with success build their own luck by hard work and taking the initiative to follow their dreams. Another, takeaway is to never give up. You will never know when the right opportunity will show up. Finally, everyone else may give up on your dream. You may need to shoulder the load alone and be a solitary traveler.

Thanks to Rodney Fife, Ironrod Media!

#2 – 3 Things

What Entrepreneurs Can Learn from the Cubs: 1) Make a plan, and stick to it – but be flexible enough to shift course within reasonable parameters if necessary. The Cubs ownership put a five-year plan in place in 2011 and it finally led them to the promised land in 2016. Along the way, they had a terrific manager, Rick Renteria, who they intended to build the franchise around. But when Joe Maddon became available in 2014, they scooped him up and changed direction following their new skipper. It really paid off. 2) Have a culture. They Cubs are not just a great ballclub. They are FUN. The play the game hard, and right, but there is a feeling of exuberance and boyish adventure that players like Kris Bryant and Anthony Rizzo exude, that cannot be found anywhere else. It filters through to the rest of the ball club, the fans, the city. Companies that build their own cultures in similar way can have similar positive impacts on their key audiences and stakeholders – and shape winning products. 3) It all starts with talent. Even with the legend, hype and management vision surrounding the ballclub, the World Championship does not happen if they do not have Arrieta, Hendricks, Lester, Chapman, Rizzo and the like. There’s just no substitute for raw ability, on baseball teams and in companies. 4) Some things that are more than 100 years old still have great relevance. Like iconic brands, great organizations, and heritage. Being an entrepreneur means embracing the new and often, focusing on the future and new modes and orders at the expense of the past. But there’s still lots to be learned and built on, from what came before – be forward-looking, plan for the future and shape it, but don’t discard the value of “old” things willy nilly. Sometimes, they will surprise you with their vitality.

Thanks to Michael Frenkel, MFC PR!

#3 – Don’t Give Up

Image Credit:Ludovic Huraux

The Cubs teach entrepreneurs not to give up, even during rough years. You can have obstacles thrown your way, get a bad reputation, or have times where you rank on the bottom. However, if you surround yourself with the right people and believe in your product or team, you can get a major win in the longterm.

Thanks to Ludovic Huraux, Shapr!

#4 – Keep Going

Image Credit: Dallisa Hocking

Even when you’re not winning, keep going! Your company may not be working the way you originally envisioned it would, but with dedication and time, the tides can turn. It’s important to not get stuck on your losses, but instead build on momentum and stay focus on each task at hand. And, when faced with a (rain) delay, pause and remember why you got into the game in the first place.

Thanks to Dallisa Hocking, Love FrogKisser!

#5 – Live in Day-Tight Compartments

Image Credit: David Radin

While the Cubs used many techniques to become 2016 World Series Champions, their ability to not succumb to worry after the Indians took a 3-1 series lead back to Cleveland was key to their series victory. To do that, they used Dale Carnegie’s first Fundamental Principal for Overcoming Worry: “Live in day-tight compartments”. The players could have worried over their losses from the Series games played at Wrigley Field; which would have affected their performance in the final two games in Cleveland – but they didn’t. They removed previous games from their mindset, and focused only on the game being played. That focus on today’s goal is part of a winning attitude – whether you’re an athlete or a CEO.

Thanks to David Radin, Confirmed™ Instant Scheduler™!

#6 – Rebranding is Tricky but Beautiful

Image Credit: Eric Gautschi

All this winning the Cubs did this season has helped to rebrand the team as a winning franchise…finally! It takes foresight, discipline and a willingness to accept fundamental change. Whenever I talk baseball with a non-Cubs fan, this subject inevitably comes up. If the Cubs win, won’t Cubs fans forever lose their
identity? What will we do without the curse and the lovable losers label? Honestly, I don’t know. The logo won’t change, the uniforms will stay the same. Wrigley will still be Wrigley. But what will the Cubs brand be? By the time this posts, the World Series will be over. Maybe the Cubs will have made history and won it all or maybe they will have just come really close. Regardless, their rebrand is already underway. What entrepreneurs and business owners can learn from The Cubs is, rebranding can be tricky, but when done correctly, it can be a beautiful thing.

Thanks to Eric Gautschi, The New BLK!

#7 – Anything is Possible

If ever there is a victory story worth noting, it is the story of the Chicago Cubs, who, with the support of a proud city, never gave up. Finally, for the first time since 1908, the underdogs won the World Series. This goes to show that with a strong team, the support of fans, and dedication, anything is possible. This is not only a lesson for fans but for entrepreneurs, and dreamers of all sorts.

Thanks to Sarah Lisovich, Central Infusion Alliance Inc!

#8 – Chill

Image Credit: Christine Pietryla Wetzler

This year it’s been very apparent how chill the team is — its temperament was fun and easy going. This positive attitude extended to the dugout and interviews, you never really saw someone acting down or beaten. As a business owner, I think it’s really important to celebrate the wins, focus on the good, and try to fight the tendency to get pulled down by a bad turn.

Thanks to Christine Pietryla Wetzler, Pietryla PR!

#9 – Stay the Course

Image Credit: Fred Schonenberg

The hype, both positive and negative, around each playoff game the Cubs played was so intense. Every loss was magnified into proof of a curse and that the wheels were falling off. Some would say, this guy can’t handle the pressure, they don’t have the tools, the series is over.. That being said, each win was met with equally hysterical celebrations of their inevitable greatness, as if they were destined to win. These super highs and super lows are very similar to running a company. Some days you feel you are the next Zuckerberg and the next day you feel overwhelmed as challenges avalanche over you. But by staying the course, focusing on your game plan and what you can control, you can slice through the hype and distractions to accomplish seemingly impossible goals like the Cubs winning the World Series!

Thanks to Fred Schonenberg, VentureFuel!

#10 – Longest View in the Room

Image Credit: Mark Aselstine

One thing that I’ve noticed about watching the Cubs, is that sometimes having the longest view in the room is a good thing. They were ok being bad for quite some time, high draft picks led to Schwarber and Bryant. Some trades were made with the long term in mind, even when it led to short term pain (ie more losses). As an entrepreneur, I think we can take away the fact that sometimes, having a longer view is a good thing. Creating compelling content won’t necessarily bring in as much business today as Google Ads, but may very well bring in many times that much business in the future. There’s some other examples in play, but sometimes being willing to work toward a longer goal gives you the space to make bigger goals happen.

Thanks to Mark Aselstine, Uncorked Ventures!

#11 – Perseverance in the Right Direction

Image Credit: Monica Georgieff

It seems ineffable to wait 108 years to be first when it comes to entrepreneurship. Especially in an age in which billion dollar unicorns are popping up every couple of years and the acquisition of a new company can come as soon as its’ first operative year. Many businesses begin to feel cursed when they find they are not growing fast enough to get ahead of their competitors immediately. In situations like these, if you believe your business or idea has the potential to be truly great, you need perseverance on your side most of all. The goal should be continuously improving your sales, your community, and your product – steadily and strategically. Accept that there is no luck, just smart, hard work to get you where you want to go. We have noticed our startup peers and competitors get penalized time and time again in various environments by betting on the shortcut to success. Although I admit, I’ve seen the shortcut work for others, I can’t guarantee it from experience. The only guarantee I can give is that perseverance in the right direction will get you to your goals sooner or later.

Thanks to Monica Georgieff, Kanbanize!

#12 – Get the Basics Right

Image Credit: DJ Francis

One real lesson from the Cubs is to get the basics right. You saw Bryant and Rizzo happy with singles and doubles. Small ball worked for them. We also went back to the fundamentals, completely re-writing our code base this year. If we didn’t have the foundation right, we wouldn’t be seeing the kind of growth we are right now as a company. We’re able to support more users and allow them to better manage their field service jobs than ever before. Go Cubbies!

Thanks to DJ Francis, Useful Systems Inc.!

#13 – Hard Work & Resilience

Image Credit: Deborah Sweeney

The Cubs have long been considered cursed – all dating back to 1945 when a proprietor cursed the team to never win another World Series because they banned his pet goat from a game. But I don’t believe in curses. I believe in the power of hard work and resilience. Over the decades, the Cubs stayed determined, worked hard and played hard, and were 100% all in for the love of the game and it paid off. This is exactly what any entrepreneur going through a tough spell needs to see to get inspired to keep on going. Maybe you might not be an immediate success, but I know for a fact that if entrepreneurs stay dedicated to their business, great things do happen.

Thanks to Deborah Sweeney, MyCorporation.com!

#14 – Invest in Talent

Image Credit: Eric Wall

Building the right team is a combination of growing from within and key acquisitions. The heart and soul of the cubs is a core of players 26 and under – Anthony Rizzo, Kris Bryant, Addison Russell, Kyle Schwarber, and Javier Baez. The Cubs trusted in developing their own talent to forge a powerful line up and excellent defensive team. However, they supplemented this youthful core with more veteran talent, including John Lester, Ben Zobrist, and Jake Arrietta. Similarly, entrepreneurs and business owners need to invest seriously in their talent so that they can develop to be the powerful core of their business. This talent should be supplemented with bringing in outside talent to critical positions where necessary.

Thanks to Eric Wall, Equity VA!

#15 – Not Let Adversity Paralyze You

Image Credit: Alon Popilskis

I think one, of many lessons, that entrepreneur can learn from the Cubs is not to let adversity paralyze you, regardless of past events. I think it could have been easy for the Cubs to resign to a believed fate of failure given the following: (1) 108 year drought (2) the fact that they were up 5-1 going into the bottom of the fifth inning only to see the lead cut in half and then up 6-3 only to see the game tied at 6-6 at the bottom of the 8th. (3) Having Chapman, their go-to reliever, give up hits to the first three hitters he faced which would then allow for a comeback by Cleveland to tie the game when he gave up a game-tying-two-out, two-strike homerun. Instead of using the curse as an excuse/believing they were destined to failure because of previous events, they regrouped as a team and focused on what needed to be done to achieve their goal of winning a World Championship. The past is just a product of your mind and while it’s useful as a learning tool, it doesn’t define future outcomes. No matter what adversity you may be facing, believe in yourself and product/company and focus on the present and what you need to do so that you reach your fullest potential and achieve success.

Thanks to Alon Popilskis, The Local Taste!

#16 – Investing in Employees Works

Image Credit: Caleb McElveen

The most important thing entrepreneurs can take away from the Cubs is that investing in employees works. The Chicago Cubs built their team from within, not by acquiring big time talent for a lot of money. They understood that acquiring the individuals that fit their culture and investing the time to develop those individuals rather than just bringing in top talent, it would pay off. Creating a culture, a process, and getting individuals to believe in that culture will be powerful. The best talent won’t matter if they aren’t in line with your company mindset.

Thank you to Caleb McElveen, Listing Power Tools!

#17 – Determination

Image Credit: Lori Cheek

Just like any successful entrepreneur, one of the most crucial traits is determination. The Cubs had their eye on the prize and they never gave up. Their performance during the series reminds me of one of my favorite quotes by Baseball Legend, Babe Ruth, You just can’t beat the person who never gives up.” and that’s how The Cubs won the most epic baseball game in history.

Thanks to Lori Cheek, Cheekd!

#18 – Surround Yourself with Stars

Image Credit: Bret Abbott

Much like the Cubs players depend on each other for success, business owners need to be on a team to push themselves to be better. Entrepreneurs are wired in a unique way, and they can learn from others who think like they do. The best way to increase the value and efficiency of your business is to get involved in a group of entrepreneurs who are willing to honestly share their experiences. In Minnesota, Entrepreneurs Organization has a group of 90 business owners who get together in smaller groups to dig deep into each other’s businesses for the purpose of growing and learning.

Thanks to Bret Abbott, Minnesota Chapter of Entrepreneur’s Organization!

#19 – Be Dedicated, Adaptive, Take Risks & Pursue Innovation

Image Credit: Robin Smith

I don’t think you need to be an industry expert to be an industry leader. Be dedicated, be adaptive, take risks and pursue innovation. This same advice can be learned from the Cubs victory, just because you are the underdog doesn’t mean you can’t win the World Series.

Thanks to Robin Smith, WeGoLook!

#20 – Believing in Myself

The Cubs’ win gives entrepreneurs, like me, a light to follow and speaks the lesson that believing in myself is the key to success. Watching the Cubs overcome years of disappointment to achieve such a sweet victory – teaches me that persistence overcomes failure. Launching Zen Squared on my own is one of the toughest, most exhilarating things I have accomplished in my forty-something life. Small failures along the way created doubt about my company being successful – The Cubs inspired me to keep going no matter the obstacles in my way. The Cubs never gave up and I will never give up.

Thanks to Julie Breaux, Zen Squared!

#21 – Ignore the Negative Critics

Photo Credit: Lisa Chu

The Cubs faced tremendous amount of negative criticisms and adversity for over 100 years, but they never let others perceptions bring them down. Year after year The Cubs kept making improvements and through their dedication, motivation and willingness to never give up pushed them to finally win the world series. Entrepreneurs can learn a lot from The Cubs. They ignored the negative criticisms and understood success did not come overnight. Negative criticism can really effect your performance, but if you choose to ignore it it will have no effect on your mindset. Never give up because success is obtainable.

Thanks to Lisa Chu, Black N Bianco!

#22 – Investing in Balanced Teams

Image Credit: David Adams

Many will continue to blame the Billy Goat for the Chicago Cubs’ previous on-field impotence. However, I believe that the Cubs suffered from decades of poor ownership that mismanaged star players and club operations. When the Ricketts family took over the club, however, they understood that building a winning club means investing from the ground up. As a result, they hired Theo Epstein from the Red Sox. They also began investing in a farm system that brought up young players who wanted to make an impact with the club, and they brought in successful veterans like Jon Lester to help these rising stars settle in the Big Leagues. Building a successful business (including baseball clubs) requires building a team balanced between young and motivated employees and veterans who have been through your industry’s ropes. The Cubs’ 7 game triumph over Cleveland just reinforces the importance of investing in balanced teams.

Thanks to David Adams, HomeSuite!

#23 – Don’t Get Discouraged When Obstacles Present Themselves

Image Credit: Jacob Dayan, Community Tax

One thing business owners and entrepreneurs can learn from the Cubs win is that it’s important not to get discouraged when obstacles present themselves. Take for example David Ross, catcher for the Cubs. In the bottom of the 5th inning, Ross let a ball get past him which ended up costing his team two runs. Instead of sulking and getting down on himself about the mistake, he brushed himself off and focused on the things he’s learned over his lengthy career. In the top of the following inning, Ross got up to bat and smacked a homer over the center field wall! Similar to that series of events, sometimes as business owners we have important deals fall through or other unexpected curveballs (pun intended) disrupt our normal course of business. When things like this happen, it’s important to not focus on the shoulda-coulda-woulda, but instead step back up to the plate and hit a home run!

Thanks to Jacob Dayan, Community Tax!

#24 – Keep Pushing Hard

Image Credit: Julie Cimity

I think entrepreneurs and business owners can learn a lot about how important it is to keep pushing as hard as you can, despite the struggles and obstacles that might appear. I was in a car accident in 2009 and broke my neck, lost my license and was unable to work for 1 year. I had a 3 year old son and had to move back into my parent’s house to raise him. Things weren’t looking good for me and I couldn’t see the light at the end of the tunnel for a few years. I had a 9-5 job and started getting clients to work for on the side at night and on the weekends. I slowly built my business until I had enough clients that I was able to work from home. That was in October 2012 and in December 2015 I was able to have my husband leave his career at DreamWorks Animation to come on board and help me build my business full-time. That was my World Series win after many years of struggling and thinking I’d never get there. Work hard and keep pushing because one day it will pay off.

Thanks to Julie Cimity, Branding Monster!

#25 – Identify & Squash Negative Patterns

Image Credit: Rick Manelius

Most people think of a curse as something inflicted upon them by other people. In reality, it’s a hypnotic trance that individuals and teams reinforce on themselves. I lived in Boston before and after they broke their curse, and the energy and attitude felt throughout the city was night and day different, which undoubtedly led to the subsequent victories shortly after it. Organizations can learn a lot from this by not allowing pessimism and negativity to reinforce itself into a self-fulfilling prophecy. Identify and squash those negative patterns early, and often so that it doesn’t take a century to reverse.

Thanks to Rick Manelius, newmedia!

What Did You Learn from the Chicago Cubs? Tell us in the comments below.

About Gresham Harkless Jr.

Profile photo of Gresham Harkless Jr.
Gresham Harkless is a Media Consultant for Blue 16 Media and the Blogger-in-Chief for CEO Blog Nation. CEO Blog Nation is a community of blogs for entrepreneurs and business owners. Started in much the same way as most small businesses, CEO Blog Nation captures the essence of entrepreneurship by allowing entrepreneurs and business owners to have a voice. CEO Blog Nation provides news, information, events and even startup business tips for entrepreneurs, startups and business owners to succeed.
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