With 11 NBA championship titles to his name, Phil Jackson is widely regarded as the greatest coach ever to play in basketball’s most competitive league. The strategy he deployed with such devastating effect during his stint with the Chicago Bulls in the ‘90s and the Los Angeles Lakers in the ‘00s was known as the “Triangle Offense.” In sports lore, the Triangle Offense emerged as one of those terms that everyone knew but no one could explain. Basketball analyst Jay Williams once said that trying to describe the strategy was like “a kid with Magic Markers drawing a cartoon. It’s all over the page. So many series of actions, I get lost trying to explain it.”
Since you are probably wondering where I am going with this piece, I owe you an attempt – albeit a feeble one – to define the Triangle Offense for context. It is a complex choreography of synchronous movement by all 5 players in a 24-second offensive possession to achieve optimal floor spacing, resulting in an unknown number of ways to score a basket. Its concept and execution seem like two different universes: a paradox of method and madness, art and science, and heart and mind if you will. Its adoption is so exclusive and successful execution so rare, you can say it rises to the level of a team philosophy. Say what?
With confusion abound, it’s no wonder other coaches would rather deploy more digestible Sloanesque pick-and-roll sets or the high octane offense that is D’Antoni’s run-and-gun ball. Yet, at the end of the day you can’t argue against results. Coach Phil’s teams have won the most and at the highest level with remarkable consistency. There is something intriguing about this hyper-technical yet amorphous strategy – or at least the analogy of it – that is worth looking into.
It’s part of my job to make sense of a business equivalent of Jackson’s vaunted strategy. At Reapra, we have adopted an abstract and dynamic philosophy that our founder has used in the past to build successful businesses. We try to harmonize the 500,000 foot view from above with the operational minutiae on the ground. Along with my peers, we look to make the abstract tangible by joining the dots of this complex way of thinking and offering start-ups a practical, replicable playbook for success.
Easier said than done, though. For starters, Reapra does things a bit differently from VCs and other types of startup investors. Whether it’s the metrics we use (profits and efficient entrepreneurship over valuation-fueled hyper-growth), the time horizon of our startups (investment horizon longer than usual, success horizon across generations), the types of businesses we select (not all sexy tech and many times traditional) and the types of founders we prefer (empathetic, sometimes deliberate and less aggressive), the Reapra Way is somewhat antithetical to the well-established tenets of Silicon Valley. Suffice it to say, going in this direction can feel very uncomfortable, sometimes lonely.
Luckily for me, I am surrounded by colleagues who also subscribe to Reapra’s mission: making society better through building sustainable industry leaders. I wasn’t interested in a game of rolling the dice on quick-to-build, quick-to-exit startups that might have had either a small or a large but short-lived impact on improving our society. But I won’t lie. There was a time when I thought there was only one way to play the game.
In a previous life, I had been a practicing lawyer before moving to work at tech giants. This put me in touch with many tech entrepreneurs in US and Asia, and I soon immersed myself in the startup world initially as an angel investor. On first impression, I was enamored with the high-energy startup culture and acquiesced to a “spray and pray” type of approach to investing. Eventually though, I started becoming uncomfortable with the norms of surviving and thriving, such as less innovative companies lacking any impetus to figure out how to make money while being hooked up to the life-support of venture capital. Being labelled as a “serial entrepreneur” was at times seen as a badge of honor, but I wasn’t fond of how others were abusing this title to justify a slash and burn approach to running businesses.
So when Reapra showed me a vision of business that put long-term sustainability, efficient entrepreneurship, and the betterment of society at its core, I immediately jumped at the opportunity to join the team.
The growing pains of putting together the playbook and making actual plays can be overbearing. We have been discouraged by the failures that have occurred under our watch. These losses rocked us to our existential core, putting into question what it is we were doing on a daily basis and what we thought we were trying to achieve in the long term. The Triangle Offense offers us some perspective. Take a look at all the flak it got despite the 11 championships associated with it. The system is too complicated and impossible to execute consistently. The system didn’t win championships; MJ, Pippen, Shaq and Kobe did. Their opponents were less talented players and teams. What about those seasons when these teams didn’t win it all? Blah, blah, blah. The debate continues to rage on. But we know we have to start somewhere. Coach Phil did too, ploughing ahead until he won.
The truth is, despite our growing research capabilities, there is a lot we do not and cannot possibly know about the future of our chosen industries. Hence, we still require some faith in the Reapra Way of investing and building businesses that go beyond relying on hard data. This is where the players come in. When Tex Winter and the authors of the Triangle Offense put things together, they had to experiment and validate their hypothesis by having actual players play out the moves and patterns. Only through continuous practice and execution did the playbook take shape. Another way to look at this is that the players themselves had co-created the Triangle Offense by putting into action in the first instance and continuing instances that which Winter had in his genius mind.
We see our relationship with our founders in the same light. Without perfect data in the industries we look to build, we look to our founders to help develop our playbook as they grow their businesses. They give life to our plays in their own way and help us revise and learn over and over again. Without consensus and impeccable best-selling business validation methods at hand, we hunt for talented founders who are at least committed to learning how to learn and learn better with us. Thus, this should not be mistaken as a traditional teacher-student relationship (how could it be if the teacher has a lot to learn too over time?). Also, we shouldn’t view the playbook as being the definitive guide on becoming a successful entrepreneur. The Triangle Offense didn’t define MJ’s individual style of play nor was it the primary factor in him becoming the G.O.A.T. It did, however, give him the system and airtime (pun intended) through which his talents shone.
And because we believe we’re doing something very different, we have no clear, single benchmark to measure against. We may still end up with more air balls than high percentage shots in the near future. Which is why I think this job to extract a plan of action out of an abstract philosophy with the right players will be key to increasing our win column. Because when we finally get the playbook right, with the right players on board, there’s no telling how many championships we might be able to rack up in the coming years.