Why Starting A Company Is (Literally) Like Rolling Dice

Learning (and losing at) backgammon is shaping the way I think about my business.

Why Starting A Company Is (Literally) Like Rolling Dice
[Photo: Flickr user Hillary]

I have been learning backgammon.


At first it seems almost as simple as Chutes and Ladders: You roll dice and move checkers. There’s little brainpower involved, you think; most of it appears to be about luck and little else. You analyze the roll and try to build defense and attack at the same time. You can see that there’s some strategy, but it doesn’t seem awfully challenging, and a great deal–way too much, it usually feels like–depends on the roll. And bigger is better: A double four is almost always better than a one and a two.

It doesn’t take long, however, until you realize that if you play against someone who actually knows what he or she is doing, someone who has practiced and observed and thought about how to best play the game, you will lose just about every time. In fact, you can find yourself in an unwinnable position after two moves, even though you may not be experienced enough to realize that.

It turns out that backgammon is far from intuitive, or something you just pick up. It requires study, memorization (there’s a lot of math, and playing percentages–rather like poker), effort, and experience. There’s jargon; there are conventions; there are moves that are not immediately obvious, but are The Right Moves, and everyone who really knows how to play makes them the same way (in this way, it’s like chess; there are openings). You have to be nimble, and smart, and change your strategies on the fly.

You probably can see where I’m going here: As in the case of startups, there’s a lot to learn, and it’s all over the place. By any measure, my startup–Purple Carrot–has been successful since our relaunch 10 weeks ago; we’re shipping 10 times as much product as we were in October, and orders are up by about 10% a week.

I suppose we should be ecstatic, and some minutes–not hours, or days, but minutes–I do feel that way. But there are so many uncertainties that the general feeling is one of discomfort. We’re giving effort, God knows, but we need experience, and we need help and, of course, we need money. And I’m not sure how to remedy all of that at once, except by working at it and then working at it some more.

In backgammon, even as a rank novice, you can spend a few hours a week studying and would, assuming average intelligence, become marginally competent in a hurry. Or at least you wouldn’t constantly embarrass yourself, as I’ve done.


But in startups, even in evidently successful ones, there are no such guarantees, and there is not even an illusion of competence. No matter how much work I do, it seems that just about everything is likely to make me feel like an absolute nincompoop. And no, I don’t think that this is necessarily because I’m a rank novice, because by definition that would describe almost everyone involved in startups (and success at one startup far from guarantees success at another, though of course virtually unlimited money helps).

As in backgammon, the moves in startups are not immediately obvious. And, like backgammon, the situation changes all the time and you have to improvise constantly: One day the priority is funding, the next day it’s hiring, the next day it’s real estate. And so on. Experience and even talent in one arena guarantees neither in any other; in fact, real experience in one field almost guarantees a lack of experience in almost every other (being good at backgammon doesn’t mean you’re good at chess, either).

In backgammon the advice is straightforward, derived from millions of games played, studied, and now computerized. Everyone except an absolute beginner knows what to do with an opening roll of three and one. In startups, the advice is all over the place. I’ve heard all of this: “Don’t take any more money than you absolutely need,” and “Take all the money you can possibly find”; “You either run out of money or you succeed, and in either case dilution is irrelevant,” and “If you’re not careful you’ll be diluted out of existence”; “In the early days, you’re the best talent you can afford,” and “The only thing worth spending money on in the early days is talent other than that of the founders”; “It doesn’t matter where your company is,” and “If you’re not in New York or San Francisco, no one will want to work for you.” And so on.

There’s a strategy in backgammon called splitting: You take two of your safe pieces and, instead of waiting for a lucky roll that will allow them to move forward together, you separate them. This is a gamble, but in many games it’s impossible to move forward without taking this kind of chance. At work, after months of consulting on almost every move, after tackling problems together, our top dogs now find ourselves in a position where we have to trust each other to make quick decisions and tackle projects almost solo. There’s just too much to do.

And what else, besides working hard and giving their most sincere effort, can startup people do? There’s plenty of perceived wisdom, but much of it is contradictory, and there are no real gurus. In fact, as almost every successful entrepreneur will tell you, luck plays a huge hand in all of this.

Just like backgammon. But that’s just a game.

About the author

Food writer Mark Bittman is Chief Innovation Officer at Purple Carrot.