Aki Ranin

Feb 15, 2018

7 min read

Startup Lessons from History: Musashi

I’m a startup guy that rarely lives in the moment. I hate news. It’s brain pollution that leaves no room for original thoughts. Like most business books. I prefer to speculate about the far future, i.e. sci-fi, or reflect on the distant past, i.e. history.

This series is a tribute to what history can teach us about startups, and life itself. We humbly begin with the most famous Samurai of all time.

Other installments you can also check out:

Future sources, ranging from fact to historical fiction, may include famous generals, philosophers, statesmen, and a whole bunch of Romans.


Miyamoto Musashi, arguably the greatest swordsman in history, lived in the golden era of Samurai. His life was a constant wandering path of following “the way”, always seeking new knowledge and skill through a series of meandering adventures.

He wrote two books himself, but the legendary 1935 historical fiction novel Musashi: An Epic Novel of the Samurai Era offers a synthesis of his philosophy as next best thing to teleporting yourself into medieval Japan.

Yes, it’s actually a 1,000 pages. But it’s all worth it for them most epic ending of all books and times. Might be my favorite book, too.

Musashi’s views are deeply rooted in traditional Japanese culture, often brief and cutting sharply as his katana.

Here we go…

Please test the lowly Musashi with hardship. Let him become the greatest swordsman in the land, or let him die.

…on setting expectations for your new venture. You won’t learn from within your comfort zone, and setting easy goals won’t provide purpose. You learn from near-failure. Not absolute failure. In your case, bankruptcy. In Musashi’s case, death. Both are overrated.

I want to lead an important life. I want to do it because I was born a human being.

…on finding meaning and purpose through your work. You only have one life to live. Don’t waste it on something that has no meaning to you, or anyone else. Even if your goals are lofty, what can you do today to start working on the problem? Working on it doesn’t have to be solving it right away!

Let others die heroic deaths, if that suited them. Musashi could settle for nothing less than a heroic victory.

…on setting your goals. Why not (moon)shoot for legendary and epic success? If you aim high and achieve 10%, that’s probably higher than 100% of your easy goals anyway.

Just a little more. How easy to say, but how difficult to achieve! For “just a little more” is what distinguishes the victorious sword from the vanquished.

…on making the difference. Success in any sport or venture is often called “a game of inches”, where the winner and loser are almost the same. Work smarter, not harder!

There was a difference between Musashi’s idea of preparation and his opponent’s. Denshichiro, though physically prepared, had only begun to pull himself together spiritually, whereas Musashi had started fighting long before he presented himself to his enemy.

…on the value of doing your homework. Yes you can try to hack, fail and hustle your way up, but most “overnight” successes were years in the making. Stopping to think is underrated.

If the young cannot harbor great dreams in their souls, who can?

…on defining the limits of your potential. Why couldn’t you be the next Elon Musk or Sam Altman? Really, why? Have you ever asked yourself this question? Is it a matter of intelligence, luck, motivation, or environment? Is it impossible?

There are people who die by remaining alive and others who gain life by dying.

…on what it takes to succeed. How far are you willing to go to prove to the world that you’re right, and all those investors who said “no” are wrong? Quit your day job? Give up your lifestyle? Sell your car? Max out your credit card? Musashi would give his life to his cause.

I intend to live for a hundred or a thousand years — in the hearts of my countrymen, in the spirit of Japanese swordsmanship.

…on creating a legacy. After your 100 years are up, are you satisfied to be remembered by a handful of friends and relatives, who will also pass and allow the world to forget your struggles? Do you want to be history, or make history?

The truly brave man is one who loves life, cherishing it as a treasure that once forfeited can never be recovered. He well knew that to live was more than merely to survive.

…on the value of your work. Nobody needs you to succeed. Or do anything, really. Survival is acceptable. Just live, then don’t. So why do you want to do more?

They say that by planting one seed of enlightenment you can convert a hundred people, and if one sprout of enlightenment grows in a hundred hearts, ten millions souls can be saved.

…on scalability. If you provide crap to millions, are you really making an impact? Then again, by deeply impacting a handful of users you could change the world!

Whether people were great or not, there was not much variety in their inner life experience. Any difference lay merely in how they dealt with common human weaknesses.

…on whether you quality to be great. Yes. There is no secret genetic formula. You can make a conscious decision. Go out with friends, or do an online course on Machine Learning. Start a new fun hobby, or do market research ever weekend. Simple decisions.

One’s self is the basis of everything. Every action is a manifestation of the self. A person who doesn’t know himself can do nothing for others.

…on seeking blame. You’re you because of you. You’re doing what you’re doing, because of you. You’re not doing the things you want, because of you. It’s not the competition. It’s not the market. It’s not luck. Look in the mirror, that’s all you need.

There are times when I wonder if I have any future. I feel completely empty. It’s like being confined in a shell. I hate myself. I tell myself I’m no good. But by chastising myself and forcing myself to go on, I manage to kick through the shell. Then a new path opens up before me.

…on the bad moments, bad days, bad weeks, and bad months that are inevitably ahead. This is where positive habits and stress resilience can make or break you. Prepare and condition yourself for the bad times. Hope is not a solution.

In an instant, the island was quiet and still as it had ever been. Only the rustle of the pines and the swaying grasses mocked the frailty and impermanence of mankind.

…on how much the world cares about your valuation and your growth metrics. It doesn’t. Same goes for your woes and worries. The trees are unmoved and unsympathetic.

All warriors have to face it; winning or losing is partly a matter of luck.

…on patting yourself on the back, or punching yourself in the face. Whatever decisions you made, live with them and the outcome. It happened. Get over it. Get over yourself. Whether winning or losing, keep improving and keep moving.

When I apply the principle of strategy to the ways of different arts and crafts, I no longer have need for a teacher in any domain.

…on the value of learning from First Principles. Any problem can be reduced to First Principles. Alternatively, you can choose, like most people, to look at the same problem through a set of beliefs and assumptions imposed by yourself or society. Which do you think is closer to the truth?

Indulging my chronic wanderlust, I am setting out on another aimless journey.

…on best laid plans. Investors will lead you to believe that modeling, budgets, and spreadsheets are keys to success. The fact is, your success will probably come in a form, place, and time that you couldn’t even imagine from where you are.

Step by step walk the thousand-mile road.

Miyamoto Musashi
c. 1584 — June 13, 1645

Get the books

  1. Musashi: An Epic Novel of the Samurai Era by Eiji Yoshikawa
  2. The Book of Five Rings by Miyamoto Musashi
  3. Dokkodo (The Way of Walking Alone) by Miyamoto Musashi

Much more to come…

Be sure to follow me if you’d like to receive a notification when the next instalment is added.

Thanks for reading,