5 Things Start-Ups Can Learn From the World Series Champion Chicago Cubs

Ask any long-suffering, die-hard Chicago Cubs fan what it meant to them to see their beloved team win the National League pennant and appear in their first World Series in 71 years and you may hear words that transcend the game of baseball and enter the realm of the spiritual. A lifetime of faith, hope, resilience, perseverance – all rewarded when shortstop Addison Russell started and Anthony Rizzo finished that double-play that sent the North Side of Chicago and Cub fans around the world to the promised land.
cubs-winBut it wasn’t a miracle or divine intervention that got the Cubs to these heights, just as it wasn’t a goat, a black cat, or an errant foul ball that kept them in the wilderness for so long. This team is a product of deliberate, patient planning and impeccable execution. It is the result of an organization that set clear goals and made the necessary investments to reach them. It is the product of commitment and talent, leadership and hard work. While a franchise that was founded a few years after the Civil War can hardly be called a start-up, the Cubs’ success does offer entrepreneurs and small business owners some powerful lessons.

Here are five key Cub takeaways for start-ups:

  • When the Ricketts family bought the team and Wrigley Field from the disinterested and neglectful Tribune Company in 2009 and hired Theo Epstein a short time later, they did so as fans, not just investors. Their love of the Cubs, their respect for the hallowed ground of the Friendly Confines, and their desire for a North Side championship are well known. While no one drops $875 million on a purchase just for sentimental value, the Ricketts started this journey with a passion for the organization and a commitment to winning. Start-ups are almost always the product of that same passion. Entrepreneurs do what they do not just for the hope of financial success; the motivation comes from a much deeper place. If you lack that passion for your business, your destiny may lie elsewhere.
  • Invest in the future. Fixing a crumbling ballpark and a losing team required money. Lots of it. The Cubs lagged way behind other clubs in building the revenue streams that are necessary for sustained success in the majors. The Ricketts not only invested hundreds of millions of their own money in the team and Wrigley Field, they made radical changes – video boards, acquiring surrounding properties, expanding the bleachers, new clubhouses, just to name a few – that were not without controversy but were absolutely required. They spent the money they needed to bring the right people to the front office and the right players to the diamond. It took some time for these investments to pay off, and their efforts are ongoing, but the results speak for themselves. The Cubs are in the World Series and Forbes now estimates the value of the Cubs at $2.2 billion. As a small business or startup, you have the challenge of spending as little as possible to bring in exponentially more. But investing resources now that may not bear fruit until much later is key to sustained, long-term success.
  • Hire the right people. Wrigley Field does not host a World Series without Theo Epstein and Joe Maddon. Tom Ricketts set his sights on the most talented leadership he could find and brought them into the fold. Epstein had the baseball acumen to assemble the right pieces on the field, and Maddon had the instinct and approach to bring out the best in his players. As an entrepreneur, you have goals and you have vision, but without the people on your team who know how to turn that vision into reality, it simply won’t happen. From the top on down, you need to hire thoughtfully and carefully.
  • Transparency and buy-in. Asking fans who have waited their whole lives for a championship to be patient is no small task. But that is exactly what Epstein bluntly asked of Cubs fans when he started. He had a 5-year plan that focused on developing young, home-grown talent rather than relying on expensive free-agents on the downslope of their careers. Executing such as plan, however, meant that those first few years were going to be rough – and they were. But by being upfront and transparent about what the plan was and warning of some rough sailing ahead, Epstein earned the trust of Cubs fans while they endured truly horrific seasons. From investors to employees to customers, entrepreneurs who are transparent and offer clear-eyed assessment of facts – good or bad – can inspire trust, confidence, and buy-in that can give their business the room it needs to thrive.
  • Hitting a home run, turning a double-play, or laying down the perfect bunt requires execution. You may have talent, you may know what to do and how to do it, but until you execute, it is nothing but theory and aspiration. The Cubs had a plan to build a team that could win and win consistently. Bit by bit, player by player, trade by trade, they implemented that plan impeccably. The business side of the organization and the baseball side worked together holistically, each focused on what it needed to do to contribute to the collective effort. The business plan you present to investors may get you the capital and resources you need to build your business, but executing that plan is the only way to achieve success.

The Cubs have taken their history – a century of repeated missteps and unmatched futility – and transformed it into the embodiment of vision, planning, and execution. While it is inherent in the nature of a start-up that there isn’t much history behind the enterprise, there may be a lot of history behind the entrepreneur, including failure. And if the Chicago Cubs can relegate their epic failures to the dustbin of history by hiring the right people to run a model business with passion and commitment, it should inspire all small business owners to do the same.