Ancelotti, Jackson and startup investing

Carlo Ancelotti led Real Madrid to their latest Champions League victory this past weekend. It's his fifth title in the competition, the highest tally for any coach.

What's striking about Ancelotti is the calm and collected figure he cuts on the touchline. He rarely gets involved during matches and rather lets his players solve problems as they arise.

An anecdote from the recent final highlights his approach. Real Madrid struggled in the first half against Borussia Dortmund and should have been a goal or two down. During half time, rather than shouting instructions to his players, Ancelotti listened. One of Madrid’s players suggested switching shape to give them more control in the midfield and Ancelotti agreed to the change.

Ancelotti bears similarities to Phil Jackson, who won eleven NBA championships as coach of the Chicago Bulls and the LA Lakers, the most in history. He maintained a similarly calm demeanour during games. In his book, Eleven Rings, Jackson summed up his approach: “Leadership is not about forcing your will on others. It’s about mastering the art of letting go.”

That doesn't mean he didn't coach his teams. On the contrary, he coached them hard. Yet, he recognised that the most important job of a coach is to provide his players with a decision-making framework so that they could think for themselves during games.

The role of startup investors is similar to coaches. Effective investors push and challenge their founders. They provide coaching to help maximise the chances of a startup's success. However, when it comes to the day-to-day of running the business, investors relinquish control to their founders.