Chess and Business Lessons from the Grateful Dead

by CEO Evan Rabin

What do, Alphabet Inc. CEO Larry Page and HubSpot CEO Brian Halligan and I all have in common? We are all self-proclaimed DeadHeads, followers of The Grateful Dead. No other band has become such a successful enterprise. Here are three of the most important lessons Barry Barnes, PHD teaches in Everything I know about Business I Learned from the Grateful Dead and how they related to chess:

  1. .Master Strategic Improvisation.

In chess, while it’s important to study and understand openings, middlegame themes and endgame knowledge, it’s also necessary to learn how to think on your feet. A few months ago, I was teaching a private student a line in the Scotch Opening. I then asked him to regurgitate the line. I purposely played a slightly different move order to see if he would change up his moves but he was so set on repeating what I taught him that he didn’t realize I played a different variation.

The Grateful Dead could play a song 1 million times and it will never sound the same. In both their music and business, they would constantly innovate as Barnes writes, “Fluid situations demand the simultaneous blending of planning and doing.” (10-11) I tell students even if they have seen an opening or endgame many times, they still need to spend time at the board making sure they are making all the right moves. This will help them avoid mixing up the move order of an opening or accidentally stalemating an opponent when attempting the king and queen checkmate.

2. Innovate Constantly: How the Dead Stayed on the Cutting Edge.

While endgame fundamentals like triangulation and the Lucena Position will never change, opening theory changes everyday as grandmasters play new novelties. Whether you are a complete beginner or a super grandmaster, it is important to continuously improve as Brian Barnes writes, “To stay ahead, a business must keep reinventing itself, keep working to change things for the better.” (128). In chess, if you are not preparing for your next tournaments, your rivals certainly are. When I was at Oracle, my Vice President Kevin McGee would often say ” If you aren’t calling your prospect today, your competitor is.” It’s important to continually look for ways to improve and provide the best possible product and service to your clients.

3. Share the Power

Many beginners make a lot of pawn moves in the opening as they are afraid to lose their pieces. Others will faultily move one piece over and over again, rather than developing all of their soldiers. It is important for a player to develop all of his pieces so they become worth their point value. A knight that is sitting home on b1 is not worth a full 3 points.

While the queen is the most powerful piece, each piece has an important role on the chess board, including the pawn. Rabbi Levi Welton likes to tell a story about when he was the rabbi at the Hampton Synagogue. Many people were confused because instead of reaching out to the older synagogue members for contributions to the shul, he decided to talk to the ‘pawns’ Erica and Mark Gerson, some of the young professionals who didn’t have as much disposable income. Rabbi Levi was actually the chess player as these ‘pawns’ ended up getting promoted as they became wealthy Jewish philanthropists.

In this sense, Rabbi Levi and Jerry Garcia think alike; while they are both great leaders, they abide by the importance of modesty. While Garcia was technically the leader of the band, “[the whole staff’s] opinion carried weight- any major decision required consensus, from everyone at the meeting.”(173). A chess player must make a plan that will incorporate all of his pieces. A band must include all of its stakeholders, ranging from the band leader to roadies, in major decisions. Likewise when Premier Chess expands into other cities, we take into account the needs our instructors, schools, partners and more.

If you don’t think that the Grateful Dead, chess and business have a lot to do with one another, you just gotta poke around! While the Grateful Dead was a rock band, it was a also a business that used many business lessons, including improvisation, innovation and sharing of power, which are all used on the chess board. Keep on truckin’!

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