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Art Took The Risk. Chess Got The Check.

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Art Took The Risk. Chess Got The Check.

Published on December 29, 2015

Eating Christ and Grinding Meat

Unless you were dipped in Catholic holy water as a babe, then you might have been old enough to remember your first visit to a Catholic church. I was. There's a choreography that noobs don't understand, that I didn't understand.

When the priest signaled communion, the entire place went into motion, overlapping, single-filing, and then looping. My wife and father-in-law, both lifetime Catholics, knew exactly how to eat and drink the Christ, but I did not. In a bustling sanctuary roughly the size and solvency of Home Depot, there I was, marooned on aisle 9, with no clue how to join in. It was like the path meat travels once inside a meat grinder: choreography to insiders, chaos to noobs.

Every novel rhythm begins this way. Then, in time and repetition, chaos looks more and more like choreography.

Now, I'm going to give an entrepreneur's take on chaos and choreography--mine--so let me be clear that this is where we part ways with my Catholic church story. MC Escher said of humans, "we adore chaos because we love to produce order," but as a first-timer at Catholic church, I neither adored the chaos nor desired to produce order. I just desired lunch and for people to stop looking at me on aisle 9.

Let's come up with a new illustration for chaos. How about a blank, white canvas? When the possibilities are endless, it's as probable to achieve nothing good as it is to achieve something good, because you can't really know whether you're on the right path until you happen upon the right path. To begin anew is to accept chaos and the risk of never graduating beyond it.

What kind of a person accepts that kind of risk? Hint: don't say "entrepreneur." Like the ethnic label "Hispanic," the occupational label "entrepreneur" lacks instructive meaning apart from the variety underlying it.

There are two competing definitions of "entrepreneur," and in order for one to be correct, they both must be correct. One version is that of the risk-taker, the artist, the visionary. The other version is that of the planner, the executor, the analyst. It wasn't until I became a full-time, failed entrepreneur that I really understood this co-dependency, that one by itself just isn't good enough.

Sure, one could argue that being just one of these still qualifies you as an entrepreneur, but the low-hanging counter to that argument is probably the arguer's own track record. Is that arguer a successful entrepreneur? Probably not. Did he try, though? Maybe. But that's not really the point of talking about what it means to be an entrepreneur, is it? We want to succeed, not just be smart but poor.

That brings me to this disclaimer: I do not yet consider myself a successful entrepreneur...just a guy who tries hard and thinks-out-loud even harder.

And here's what I'm thinking: it takes art to begin, but chess to win.

(FYI, imagining the combination of art and chess on a timeline left to right, I think I'm somewhere right of center; I've pretty much nailed art but have a lot to learn about chess.)



Entrepreneur-artists stand out for their eccentricity and apparent naivety. They embody quotes like: "Only those who attempt the absurd will achieve the impossible. I think it's in my basement...let me go upstairs and check (Escher)." "The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man (Shaw)." "The earth is round, not flat (some Greek dudes and then Columbus, probably)."

To me, Steve Jobs is the quintessential entrepreneur-artist. He didn't cut off his ear and mail it to an ex, but he did do some crazy stuff for crazy reasons. I wouldn't say that he, at times, suspended rationality; I would say that he, at all times, subscribed to a different brand of rationality than everyone else, his own eccentric brand, one in which form and function were one and color trumped thrift (if you don't know: Jobs famously spent millions painting Apple's manufacturing facilities handpicked colors over and over again).

The entrepreneur-artist is a tragic hero in the Greek sense. If he fails, we all say, "if only he had heeded our advice and stopped doing that one thing we all clearly knew would doom him." If he succeeds, we all say, "I don't know how he did it, nor did I see it coming, but he clearly knew what he was doing--must be a genius."

But did he know? Or did he just believe, and then eventually get it right, find the luck that evades most?

When asked, one painter described his process as "telling a story to which you don't know the end." To me, that's the tautological definition of an entrepreneur-artist:

  1. You believe something no one else believes.
  2. This belief is purely faith-based.
  3. The outcome of your work is uncertain.

The conviction of your belief is based on your own original analysis, consisting in part of data, inferences, and synthesis.

Imagine three napkins, one for each part of your analysis. On one napkin, you compile data, on another, your inferences from that data based on your experience, and on the last, the visual part of your art, your novel synthesis. You combine things no one has combined before, and this is what the rest of the world will see. The first two napkins are footnotes in support of the third, your argument. Your startup matters because [your synthesis] and can do something no one has ever done before because [your synthesis].

Importantly, though, your belief is faith-based, unless/until you prove it, and entrepreneur-artists, by definition, precede proof (that's my view, anyway).

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(For example, this is the synthesis Columbus probably used in arguing for a westward route to India, much of which he borrowed from earlier syntheses of others.)




Now let me say something about Jobs that illustrates my point. Yes, the guy was nutty--in the beginning, that's what he mostly was. He alienated people; he didn't bathe; he lied constantly; and he completely disregarded his first-born daughter. In sum, he ignored consequences. Yes, he had passion. Yes, he was brilliant in painting the future he aimed to build. But it wasn't until he learned to plan and consider consequences that his march to success really began. He learned to envision his endgame and to simplify the map leading to it. He became a chess grandmaster--still uniquely artistic, but accountable.


To my earlier questions (But did he know? Or did he just believe, and then eventually get it right, find the luck that evades most?), no, I don't think he saw it coming. Nor do I think he got lucky. I think the experience of tragedy (getting booted from Apple), of failure (foundering at Next), taught him how to focus on results, to take nothing for granted, and to methodically apply all of the practical lessons and skills learned along the way.

Making this point, Peter Thiel quotes Grandmaster Jose Raul Capablanca: to succeed, “you must study the endgame before everything else.” What I've learned, though, is that this isn't step 1. This is something like step 40, the first thing you do after you've learned everything not to do, but as important, after you've deluded the artist in you to first take the risk. It's like WD-40, which stands for "water displacement, 40th try." It takes an artist to discover the formula through 39 failed attempts, but it takes a planner to turn that formula into a successful business.


The entrepreneur-chess-player is defined as:

  1. You know the winning formula (or at least the best formula to lead you to the next best formula to eventually lead to the winning formula).
  2. When you wake up in the morning, you know exactly what you (and your team) should be doing to inch toward success.
  3. You study the game obsessively, and you modify your moves as needed.

If you think about it, the entrepreneur-chess-player is really just an investor's ideal entrepreneur. He knows what to do; he gets it done; and he's data-driven. The inverse lesson here, though, is that the artist matters, too. Which matters more is a question of timing and order and results. This dichotomy, I bet, is the root of most difference between how entrepreneurs and investors think. Yes, you should know what to do, get it done, and be data-driven, but expecting to begin there is like expecting a Picasso print from a blank, white canvas--there's a bit of setup work first.


My Take on Chaos and Choreography

Art must take the risk. But chess must get the check. If you want to do something truly novel, this is the proper order. I learned this by fire and observation, and although I'm telling you this now, I suspect that the only way you can learn this is to fail yourself. It gives you no advantage, I think, to have read this. You still have to dream, fail and starve yourself, as artists do, before you land.

On the other hand, if you wanted to simply be a plumbing startup, then there's no necessary invention, and you can thus leave your finger paint at home. Just plumb and plan, and leave the IoT, cloud-based plumbing apps to the crazy ones.

If you need me, I'll be boning up on my chess game, watching the paint dry.