Playing the long game


Fred Wilson recently posted a great article entitled Don’t Kick the Can Down the Road. It exhorts entrepreneurs to not avoid making hard decisions. Great advice — and yet, sometimes you need the patience to let things develop, or not make a decision before you need to. (Ironically, many VCs — not necessarily Fred — are past masters at not making a decision, happily telling entrepreneurs “come back when you have more data” vs. just telling them no and getting it over with).

I recently read Shogun, James Clavell’s enormously entertaining and informative novel about set in feudal Japan. It is a master class in how patience is necessary to achieve big goals.


A bold English adventurer. An invincible Japanese warlord. A beautiful woman torn between two ways of life, two ways of love. All brought together in an extraordinary saga of a time and a place aflame with conflict, passion, ambition, lust, and the struggle for power… From the Paperback edition.

Blackthorne is an English ship navigator marooned in Japan (loosely based on the exploits of the real historical figure William Adams, the first Englishman to reach Japan and the first western Samurai). He is made Samurai by lord Toranaga (a fictionalized version of the historical figure Tokugawa Ieyasu). The novel is ostensibly focused on Blackthorne but the true central figure of the book is Toranaga. Toranaga secretly desires to become Shogun, the supreme military commander of Japan, and de facto ruler of the country. But against him are an array of other leaders, with a stronger political position and bigger armies. Toranaga is the master of not making a decision until he has to, or the time is right:

though in reality it was only a cover to gain time, continuing his lifelong pattern of negotiation, delay, and seeming retreat, always waiting patiently until a chink in the armor appeared over a jugular, then stabbing home viciously, without hesitation.


“Doesn’t this explain Toranaga? Doesn’t this intrigue fit him like a skin? Isn’t he doing what he’s always doing, just waiting like always, playing for time like always, a day here a day there and soon a month has passed and again he has an overwhelming force to sweep all opposition aside? He’s gained almost a month since Zataki brought the summons to Yokose.”

In the end, it is all about patience, or as Toranaga says:

Patience means holding back your inclination to the seven emotions: hate, adoration, joy, anxiety, anger, grief, fear. If you don’t give way to the seven you are patient, then you’ll soon understand all manner of things…

If you’re building a business, you don’t have to raise venture capital. The tech press romanticize this path. You can bootstrap, but that requires patience (and resources or a very low burn rate). But if you are patient, passionate, and committed, you can build a very interesting company this way.

This strategy doesn’t lend itself well to fast-developing, winner-take-all markets. Competing with an Uber or a Groupon, you have to scale fast or get run over. In venture-backed companies, you are on the “shot clock” as soon as you take money — investors want a return. Conversely you become addicted to the funding and can’t survive without it, so you have to succeed quickly or you’ll run out of money.

In more slowly developing markets, or markets that are small enough that big money or big companies aren’t a threat, patience can be a virtue, or even a requirement. Books are an interesting example. The market develops slowly. The few major success stories, say Goodreads or Wattpad, were almost a decade in the making. Any number of innovative startups (e.g. discovery engine Small Demons, subscription reading platform Oyster) produced great products but were unable to fund operations long enough to achieve critical mass.

So, with my book discovery engine, The Hawaii Project, I’m playing the long game. I’m not raising funding and going for the big splash, because I know the market will take longer to develop than the shot clock will permit. I’m self funding. Cloud computing and open software have made it possible for a single person to build very interesting products, and let them run for long periods of time at very little cost. I can wait out the competition; most of them will run out of money.

When I meet with young entrepreneurs embarking on something, one of my first questions is, “Do you care enough about this problem to spend 5 or 10 years of your life on it?”. Because that is what it’s going to take.

Be Sociable, Share!

Leave a Reply

Your email address will not be published. Required fields are marked *