Tokyo Cowboy: Waking up Before it’s Too Late

Movies and their lessons show up at the strangest and usually right time. On a flight to Paris with my family, I got to watch “Tokyo Cowboy”. The synopsis: “a Japanese businessman goes on an unwitting journey of self-discovery when he takes a company trip from Tokyo to a Montana cattle ranch.” With a description like this, how can you not be intrigued?


The main character is a businessman named Hideki Sakai, when we first meet him he is a dedicated yet dour salaryman responsible for acquiring and turning around companies. Maybe too dedicated to his career. 

Like many folks around us, he is doing what he thinks he is supposed to do in society. Rising through the hierarchy, getting promotions and money. He focuses on efficiency and numbers far too much. Over optimizing everything. Except the important things in life. I get it, I was once this guy. 


There is a scene early in the movie when he takes over a chocolate factory. He sees how dedicated the owner is. He says to the owner: “you really love your work.” The owner asks him: “Absolutely. Don’t you?” The blank look by Sakai says it all. It’s the blank look of NOT understanding. 


His trip to Montana is driven by a project and his own personal brainchild: turn a loss making cattle ranch in Montana into a mass wagyu beef ranch. But he starts to run into problems. The expert named Wada he hires tells him. “Beef was always meant to be a small business. Quality or quantity. You can’t have both.” 

This seems like a universal axiom. Relevant to relationships, products and positioning. High end niche or mass scale. Exclusive or widely available. In my world, it’s the barbell: big massive venture banks on one side, small niche emerging venture funds on the other. Woe to those stuck in the middle. 


Another complication, he is dating his boss, and during a business discussion she tells him: “speaking as your boss. You messed up.” He responds: “So I had a miscommunication. But the numbers are solid.” She wisely says: “Not everything is about reading the numbers. You need to read people too.” 

She is sharp. It’s good advice & something many young business people get wrong, especially MBAs. The focus on numbers. When running a business, it certainly is about numbers, but it’s mainly about managing people: the soft stuff is the hard stuff. 

We see Sakai’s lack of understanding this point. When he is about to reject an invitation to meet the ranch manager over drinks, his consultant Wada stops him and says he has to. “Look, ranching is a people business. If they wanna have a drink, we should have a drink. Drinking’s not about the drinking. It’s about building rapport.”

And this rapport is needed. When his consultant gets into an accident, he is stuck by himself & has a bad start with the ranch hands when presenting his new vision of the ranch. It’s awkward because it shows how little he understands their business. And the culture clash. So painful to watch. He is just the man in a suit showing up every few years trying to tell the local experts aka ranchers and cowboys how to do their job. 


But Sakai slowly learns. It’s like a Japanese modern City Slickers (for those old folks who know the Billy Crystal movie). He also starts to learn about himself, the deep emotions he keeps bottled up inside. Japanese culture (like many Asian cultures) can be a stoic and some would say oppressive culture. You stifle your emotions to fit in. (Taiwan used to be a Japanese colony btw, so I get this). 

His guide and minder Javier schools Sakai on getting the ranch hands on board with his plans. “You could change their minds but you are doing it wrong. You gotta meet them halfway. Learn how we do things here. You gotta speak their language. And I’m not talking English. You know.  Get them to trust you and they will listen.” So basic, so simple yet so powerful. And it works in movies and in real life. 

Sakai ditches the suits and dresses like a cowboy. He starts to learn the ways of the cowboy and goes on a cattle drive with the ranch hands. It’s neat to see him learn, adapt and grow. 

Something all of us need to be doing on a regular basis. Sakai starts to love the life. He enjoys the camaraderie with the cowboys. He even finally notices and appreciates the beautiful wild Montana scenery all around him. 


He also learns that efficiency is not always better. “I thought I was making things better…….

If I have to destroy it to save it, then I won’t be saving it at all.” This was exemplified by the take over of the previously custom handmade chocolate company. One that he wrecked by changing to cheaper chocolate bean suppliers and putting in new processes to speed up production to increase margins. He discovers the chocolate tastes waxy and terrible. 

This reminds me of widespread financialization and private equity-ization of large swathes of the American economy, which has led to ruin for these industries and companies. 


Well at least Sakai-san wakes up before it’s too late. He has a re-awakening of his soul. He has a chance to fix things. And so do we all. “It’s not all about the numbers.” 

It ends with Sakai on a horse overlooking the gorgeous Montana mountain scenery of the ranch he has just acquired himself to save it. To me it also shows that he has saved himself. 

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Marvin’s Best Weekly Reads Nov 2nd, 2025