(Photo Credit: WurFi)

This is a short and very personal episode. Things will be changing for me and for Disrupting Japan, and sometimes when you are facing a lot of big changes, it really helps to be able to share your thoughts with people you care about.

That’s you.

There is no guest this time. It’s a story about me and magic and chivalry and startups.  I hope you find something in it.


Disrupting Japan Episode… well, that’s kind of complicated.

Hi. Tim here. I’ve got some big news that I can only tease you with right now, but I wanted to share it with you in this special, short in-between episode.  There are no ads this episode, because … well, because this one is not brought to you by our sponsors, it’s too personal. It’s brought to you by me.

Now, no one has ever been surprised to learn that I was a huge nerd in high-school. And this was back in the 1980’s, a very long time before nerds were even remotely cool, and female nerds simply didn’t exist.

Actually, no I take that back. I’m sure there were female nerds back then, but social norms being what they were, they had to stay in the closet and hide their nerdy nature from the rest of the world while pretending to be interested in cheerleading and quarterbacks and what have you.  So I guess that the 1980s were a tough time to be a female nerd. Nerd liberation came later for girls than it did for boys, but the 80s were not a great time to be a male nerd either.

Anyway,  I was on the debate team and spent my free time programming my Commodore 64, playing Dungeons & Dragons, and arguing the finer points of Tolkien’s Lord of the Rings with my equally nerdy friends. Now over the years, I’ve given up on the idea of debate for debate’s sake, upgraded my computer, and I haven’t played D&D since high-school graduation.

However, I still enjoy Tolkien and find myself re-reading his books every decade or two.  The Lord of the Rings is a classic tale that is beautifully told, and generations of nerds have found in it not simply an enjoyable distraction, but as profound human insight and as inspiration on leading a life well lived.

But recently, and as a result of this serial entrepreneur life I’ve chosen, the characters in The Lord of the Rings have been seeming a bit thin, and those of another novel have started to seem richer and richer.

Back in high-school, I considered Cervantes’ Don Quixote an interesting enough story, but over the years as I’ve embarked on several radically different careers and started startup after startup, something about the novel started to resonate with me.  As the Lord of the Rings began to feel more and more like a well-told fairy tale, Don Quixote began to seem, well a little bit like me.

For those of you who have not read the book in while or who have only seen one of the movies, all of which miss the core point of the book, let me explain

Cervantes wrote Don Quixote more than 400 years ago, and he tells a story of a man who lived in a time of overdue bills, nosy neighbors and bickering politicians. It was a time when the world was filled with petty people with tiny dreams wasting their lives in mundane and meaningless pursuits. 

Well, Quixote dreamed of a better world. A world where life had honor and meaning. He desperately wanted to live in an age of chivalry. A time of damsels in distress and knights errant, a time when there were still giants left to slay.

He believed in his vision so passionately he began to see the world not as it was, but as it could be; as it should be.  Farmers became noble squires, peasant girls became princesses, and most famously, windmills became ferocious giants.

Now Don Quixote is not a heroic figure. He never managed to change the world.  In fact, no one ever believed in his vision except for him.  The world viewed Don Quixote as a somewhat amusing, but a pathetic and pointless person. 

When you read the novel, you get the impression that even Cervantes, himself, couldn’t quite make up his mind about whether he was on Don Quixote’s side or not. The author is ruthlessly cruel to the character, putting him through failure after failure and moving him from one manner of humiliation to the next.

But every once in a while you glimpse the unmistakable theme that “Hey, Quixote is right. The world as he sees really is better. But this is what happens when one man is right and the rest of the world is wrong.“

Don Quixote spent his life following his vision and his passion to absolutely no avail. He led a life of failure and humiliation, but somehow managed a life well lived.

And that is something that any startup founder should be able to admire.

Now before you get the wrong idea, and before my investors get the wrong idea, I don’t pattern myself after Don Quixote, and I don’t identify with Don Quixote. I don’t seek out and pursue opportunities for failure or public humiliation.  At least not consciously.

Cervantes story resonates with me more than Tolkien’s. It’s more real.  When we are young, we liked to imagine that we are on the hero’s journey. Being the chosen one, fulfilling a destiny that was prophesied in ancient times. Standing clearly on the side of good, struggling together with powerful allies to defeat an evil and seemly invincible enemy.

But the world is not like that.

As Don Quixote finds out, most people don’t share your vision or care to accompany you on your journey. You spend your life trying to shape the reality around you into something that vaguely reflects what you see in your head, and you fail at it most of the time.  And, of course, any giants you slay, are going to be ones of your own creation.

Any startup founder who sees more of himself in Gandalf or Frodo than he does in Don Quixote is probably better off in another line of work.

So, why am I talking to you today about fantasy novels? Well, there are some big changes coming up for me. I can’t announce the details just yet, but it will all come out soon.  All I can tell you is that I’m joining a startup team that is trying to solve a very important, but extremely difficult problem.

.. and I’ve always been a sucker for those.

It’s far from a sure thing, but if we execute right and are more than a little lucky, we’ll not only make a great deal of money, but we will fundamentally transform one of the biggest industries in Japan.

The great thing about tilting at windmills in the startup world is that every once in a while, the windmill loses.

So what does this mean for Disrupting Japan?  Don’t worry. The show will go on. The show must go on. I love producing this show. I love the conversations I get to have with some of the most amazing startup founders in Japan, and I love talking with you each week and with talking with listers when you reach out over email or when we bump into each other around Tokyo. Disrupting Japan has been one of the most challenging and rewarding projects I’ve ever started, and its going to continue.

I will, however, be making some changes. I won’t be able to keep up the weekly releases so I’ll be going back to releasing every-other week, and I’ll be scaling back on a lot of the advertising as well.

This will all be happening in the next month or two, and when it does I’ll let you in on all the details.

And I promise I’ll do it without a single digression into the themes of 400-year old novels.


Ah, Cervantes and startups….. Let’s get back to that….

You know, members of the startup community will tell you that it is important to embrace failure, that the startup community celebrates failure. There are at least two large international startup conferences built around celebrating startup failure. 

But in our hearts, we all know it’s a lie. We don’t celebrate or embrace failure.

We celebrate the winners who have bounced back from failure. We celebrate rich and powerful failures who brushed themselves off and then achieved great things.  This is not an acceptance of failure. Quite the opposite. It is a way of heaping additional glory on the successful by pointing out that they once were failures, but managed to overcome it.

To society at large, failure is only celebrated in retrospect after future deeds prove to everyone else that you were not really a failure after all. Outside of, at best, a small circle of friends, no one but you will assign value to any of your failures unless you later succeed.  And as startup founders, we need to understand that’s the way it is.

Truly accepting failure would mean embracing beautiful failures like Don Quixote. People who spend their lives pursuing their vision, taking risks, defying the odds, but failing time after time. You know, I think part of us really wants to admire people like that, but human nature just won’t quite let us.

And, of course, inviting someone like that to speak at Failure Con of Fuckup Night would be unthinkable. We only want to hear from the successful failures.

I suppose I do see a bit of myself in Don Quixote, or perhaps a bit of him in me would be more accurate.

In fact, almost all of my adult life has been making the best out of one failure after another. With very few exceptions, I’ve never quite managed to achieve what I set out to do, but somehow over the long run, things seem to get better for me, and hopefully for those around me as well.

I’m not kidding about that. I’ve been fired or pushed out of half the real jobs I’ve ever had.  I barely managed to graduate college because I ran out of money and had to graduate early. My music career. Well, we don’t even need to talk about my music career.  I’ve had more than a dozen startup projects flame out and even my two exists were quite modest and a tiny fraction of what they would have been if … if lots of things. There is always an if…

I certainly don’t consider myself a failure, I consider myself to be quite successful, but there are not many things I can point to and say “I succeeded at that”, but hey maybe next time. Perhaps the Bill Gates and Mark Zuckerbergs and all the home-run hitters of this world really are living the hero’s journey,  but I think that far more entrepreneurs have built a life by quietly picking up the pieces after each failure or disappointment and seeing what can be built with them.     

You know, even Disrupting Japan.  I started this podcast after a book deal I was negotiating fell through.

We might want to live in Tolkien’s world, but we actually live in Cervantes’ world.  A world of overdue bills, nosy neighbors, and bickering politicians. A world filled with petty people with tiny dreams wasting their lives in mundane and meaningless pursuits. 

We founders love to tell ourselves that we are changing the world and doing battle with the evil giants of our industries.  It’s a delusion of course. These large companies are not really evil giants, but the world is so much more exciting and meaningful when we tell ourselves they are.