One of my passions is the study of strategy and leadership. Whether military, business, sports or political, I have always been fascinated by the thinking and decision making that goes into out-thinking your opponent and getting people to follow you, especially in chaotic times. I have read untold number of books and treatises on the subject and have been fortunate to discuss strategic concepts with many different types of leaders who are at the top of their field.
When I was younger, my preferred outlet for strategy engagement was playing chess. I ended up being the junior high school state champion and later, when playing speed chess, obtained a draw with a Grandmaster. In the early days of World of Warcraft, I organized raids and led PvP teams. I have studied a number of martial art styles, eastern as well as western sword fighting and the philosophies behind them.
More recently I find tournament poker more closely estimates the right kind of mind set for strategy. My take is that unlike chess, where there is almost no element of chance involved, poker consists of 33% playing your cards and position, 33% knowing the habits and psychology of the opponents and 33% blind chance – all with the ticking time clock of continuously increasing ante (burn rate for all you startups). It is worth noting that sometimes the very best hands, played perfectly simply don’t win – but as the saying goes, the better you can play your hand and the people at the table, the luckier you become.
So now, while I like to play poker now and again, I note that the world’s greatest chess player, Gary Kasparov, quit chess to enter politics. Like him, I have found that the most meaningful strategic wins are not from cloistered study nor are they merely games. That is why I seek my strategic fix elsewhere these days. I discovered that the real joy for me is in using those skills to create organizations that matter and advocating policies that I care about. Having founded a dotcom startup and later working as an advisor to two Prime Ministers and as a political operative, I have been fortunate to be able to apply the theory I learned to many real world issues. I tell myself that my motivations are to make a difference in this world, but I have come to acknowledge that I also enjoy the game.