This is the amazing story of Yoshiaki Tsutsumi (tsoo-TSOO-mee) — who, for four years straight from 1987–1990, was ranked the richest person in the world, the most powerful and probably the most revered businessperson in Japan throughout the 70s and 80s. And yet, for all his wealth and power, very little is known about him — but what we do know of his rise and very public fall (because there is a big fall) makes for a fascinating story. It’s a cracking episode — enjoy.
Yoshiaki Tsutsumi (tsoo-TSOO-mee) was born on May 29th, 1934 — the son of Yasujirō Tsutsumi, one of Japan’s richest and most complex postwar tycoons — and the more I researched this story, the clearer it became that Yasujirō, the father, has a story that is equally brilliant, so I will do an episode on him someday.
Yasujirō, the father, was born into a relatively wealthy land-owning rural family, but he didn’t want to stay a large farmer, so he started building houses, then investing in other businesses and expanding into resorts, eventually building what became the Seibu Group.
His son Yoshiaki had an unusual upbringing because he wasn’t born into what you’d call a traditional family — his mother was one of Yasujirō’s several mistresses.
He was one of seven acknowledged children — and I say acknowledged because his father was rumoured to have anything between 50–100 children. And because Yoshiaki was born out of wedlock, he spent his early years quietly, tucked away in a Tokyo suburb with his mother and two younger brothers. Hidden, really. The arrangement suited his father’s secretive life — Yasujirō kept each of his many families at arm’s length from the others.
But he seemed to have marked young Yoshiaki as a potential heir, because he brought him along to meetings, gave him small jobs — holding blueprints, giving him little lessons about how to run a business. Insiders said it was clear that Yoshiaki was being groomed.
In 1941, when he was seven years old, Yoshiaki met his half-brother Seiji for the first time. Seiji was fourteen, the legitimate heir — the two were like chalk and cheese. Seiji was the intellectual one — soft-spoken, reserved — but also probably the only one who rebelled against his father. As a student he joined the Communist Party, which was an affront to his father, and many believe that it was that act alone that resulted in his father favouring Yoshiaki, because Yoshiaki was very much in line with his father — he had his father’s blunt confidence and drive. And he idolised his father, often saying throughout his life that his father was “the greatest entrepreneur I’ve ever met.”
After WW2, Japan was shattered — bombed out, broke, and occupied by the Americans. Yasujirō saw an opportunity. Around 1947, he began snapping up land from noble families who couldn’t afford new property taxes and built the Prince Hotel chain to add to his existing business holdings of railways and holiday resorts. He was also very active in politics — in 1953 he was elected Speaker of the House of Representatives of Japan.
In 1955, Yoshiaki was 21, still in college.
He’d always loved sport — skiing, ice hockey, anything that involved speed and spectacle — and that shaped how he thought about business. Leisure wasn’t a side bet for him; he believed it was the future because Japan’s middle class was growing at a very fast rate, and they were looking for recreation, and Yoshiaki saw that coming before most.
So with this vision in mind, and keen to prove himself to his father, Yoshiaki planned his first venture.
Using some land that the company had along transport lines controlled by the parent group, he built an ice rink. Now, this first venture wasn’t huge — but it was a success, and its success not only demonstrated that his instincts were right, it also gave him credibility, confirming his own father’s judgement — that Yoshiaki had the right stuff or, as Logan Roy might say, he was a serious person.
After graduating in 1957, Yoshiaki joined the family company full-time. Colleagues said he was soft-spoken but steely, modern-minded but deferential to his father. He studied operations in detail, touring every hotel and rail line. And by the early 1960s, he was co-running major projects, handling political relationships, and quietly consolidating his position as heir.
In 1961, the company launched its most ambitious project — the Naeba International Ski Resort, situated about two hours from Tokyo — this huge, sprawling alpine complex: a full-scale destination with ski runs, chairlifts, and the Naeba Prince Hotel at the base of the mountain with hundreds of rooms.
And while his father officially led the project, it was Yoshiaki, then still in his twenties, who was working behind the scenes to make it happen. He was obsessive about the details — slope angles, lift capacity, guest flow — every little detail. People who worked with him said he could talk as passionately about the curvature of a ski slope as he could about a balance sheet.
For context, this was at a time when Japan’s middle class was emerging and incomes were rising. The late 1950s and early 1960s marked the height of Japan’s postwar economic miracle — years of rapid industrial growth, urbanisation, and newfound optimism. Western fashions, cars, and sports were flooding into Japanese life. Skiing represented affluence, sophistication — a sign that Japan had rejoined the modern world.
In 1964, Yasujirō died at seventy-five, and in his will he left Yoshiaki the businesses that he had already been more or less running: the railway lines, the hotels, resorts, and vast amounts of land, while Seiji, the eldest son, got the struggling department store business — which, of course, was no surprise to those who had worked within the company, but to the rest of Japan it was a huge scandal. One paper called it “a shock that upended every rule of succession.”
And the ultimate insult for Seiji, the older brother, happened at the funeral because it was Yoshiaki who served as chief mourner, a role traditionally reserved for the eldest son, and by all accounts Seiji was really pissed — which is pretty understandable.
Under Yoshiaki, the Seibu Group expanded at a fast rate throughout the 60s, with new Prince Hotels springing up across Japan. Private railway lines stretched deeper into resort areas. And he stuck to the formula that he had built the business on: build a hotel at the destination, extend the railway to reach it, and surround it with leisure facilities that kept people spending.
Now, some of these new resorts he built were massive, and while the group was very profitable, it still needed vast amounts of money to build these huge developments, so Yoshiaki did what his father had done: he borrowed heavily, using rising land values, borrowing against one property to build the next.
So he was taking on a lot of debt, a lot of risk. But risk was very much part of his father’s philosophy — because Yasujirō had gone deep into debt after the war to buy all that land from cash-strapped aristocrats.
By the early 1970s, Yoshiaki had become one of Japan’s most powerful men.
He was widely respected (and feared) in business circles, known as a man who rarely took “no” for an answer and who kept his operations notoriously opaque to outsiders, rarely ever giving interviews.
So it’s really hard to get any real sense of his character — the few friends who comment on him describe a complicated figure: tough, but shy. Creative, yet unassuming. Inventive, with a tendency to be dictatorial. This is the real problem with trying to get an insight into Yoshiaki — we only have a few quotes from friends, or maybe it’s more accurate to call them associates, because by most accounts Yoshiaki was, and is, a very lonely figure, with very few real friends. He did marry and has three children, but as you’d expect, his family life is a closed book, and so we can only get a measure of the man based on what he did — on his actions.
In business he was progressive in some ways, in that he brought in professional managers and used market research to keep up with changing tastes.
And yet at the same time, he continued to micromanage — he’d obsess over the tiniest details. For example, he once ordered that all the hotels' sugar packets be shrunk because he felt they were holding too much for a cup of coffee.
And other than business, the only other things we really know about him are that he loved sport, was a passionate skier, and held a black belt in judo — just like his father did.
And he combined his passion for business and sport in 1979, when he bought the struggling Crown Lighter Lions baseball team for $3.3 million. He renamed them the Seibu Lions and moved them to a brand-new 30,000-seat stadium he’d just built outside Tokyo.
Now, I always wondered why or how baseball became such a big sport in Japan — so here’s the answer: it was introduced in 1872 by American teacher Horace Wilson at a time when Japan was modernising and adopting Western ideas. It spread quickly through schools and universities because it resonated deeply with Japanese values of precision, hierarchy, and dedication. Its professional league was launched in 1936, and it became a unifying national pastime and a core part of the country’s cultural identity.
Now, while Yoshiaki loved some sports, he admitted himself that he knew little about baseball — but he understood brand power. Because the success of the baseball team reinforced the company’s, and Yoshiaki’s, identity as the architect of Japan’s leisure culture — a company that didn’t just sell holidays but built the experience of modern recreation itself.
Within three years of taking over the Lions, they were champions, and the team dominated the 1980s and early 90s.
By 1984, his influence and power were evident at his mother’s funeral — and remember, she wasn’t his father’s wife, she was a mistress — and yet the sitting Prime Minister, alongside three former Prime Ministers, attended her funeral. For a private citizen’s family ceremony, this was unprecedented.
So by now politicians and other business leaders treated him like a kingmaker. But unlike his father, he didn’t have any interest in getting into public politics — he lobbied behind the scenes, pushing for policies that aligned with his developments.
And then came 1987 — Forbes launched its first-ever list of the world’s billionaires, and sitting at number one was Yoshiaki Tsutsumi, with an estimated fortune of $20 billion. This was the moment when the rest of the world became aware of this Japanese tycoon.
But there was a lot of secrecy around his fortune. Forbes believed he owned 40 percent of the holding company, but admitted it didn’t know who held the other 60. If Yoshiaki secretly controlled those shares too, his real wealth could be over $50 billion.
Now, I’m always interested in these lists. It’s childish, I know, but there you go, so I took a bit of a detour to dig into that first list. Four of the top five people on that list were all Japanese, and there were six Japanese people in the top ten.
I was so surprised to find out that there were no Americans on that list. The other four countries represented were Canada with two billionaires — Paul Reichmann, the real-estate mogul, and Ken Thompson of the Thompson Corporation — the Hansing brothers from Sweden who owned Tetra Pak, and Salim Ahmed bin Mahfouz from Saudi Arabia who founded the National Commerce Bank.
Now, of the six Japanese people on that list, five of them were involved in real estate in some shape or form, giving us a great insight into the wealth and the booming nature of the Japanese economy at that time. Because the country was in the middle of a huge land bubble. Land values had risen fifty-fold since the 1950s, and Japan’s total land value was now said to be four times that of the entire United States, despite being a fraction of its size. In one of Tokyo’s shopping districts, the cost per square metre was $250,000 — to put that in perspective, property in Manhattan today averages around $25,000 per square metre — so 35 years ago Tokyo was ten times more expensive than current-day Manhattan. The Nikkei index was soaring toward its all-time peak, banks were lending freely against skyrocketing land, and Japanese conglomerates were buying trophy assets like the Rockefeller Center, Pebble Beach golf club, and Van Gogh paintings. I think we can see where this is headed.
A year later, Yoshiaki topped the list again with his fortune put at $19 billion. When reporters pressed him about being called the richest man on earth, he brushed it off. Paper wealth, he said, wasn’t what mattered. “True value is in lasting assets, not rankings.”
And yet, despite all his wealth, Yoshiaki’s drive continued and was relentless. Inside his companies, he ruled with the same intensity that built his fortune. He expected his workers to show the same commitment and effort that he put in — as can be seen from this quote where he once told his executives: “If you want Sundays off, don’t be a manager in my company.”
Now, I always have a big problem with this kind of leadership. We see, or rather hear, it from Elon Musk all the time — and I’m singling out Musk here because this is something he is known for; he’s very public about it — but just to be clear, there are things that Musk does business-wise that I do admire. But this idea that your employees should work themselves to the bone, should work around the clock to realise the founder’s vision? Screw that. Yes, by all means inspire your employees, get them fired up by your vision, get them to give you 100% when they're at work — and if some of them are workaholics just like the boss, then fine. But to expect all of your employees to work 24/7? That’s just not sustainable. It might have worked 30 years ago when people stayed in the same job, but these days you’ll end up losing some of your best people.
Anyway, for Yoshiaki and his employees in the 1980s, it was all work. His firms bought and built at breakneck speed — new resorts, luxury hotels in city centres, suburban rail towns springing up almost overnight. By this stage his company operated $400 billion worth of railways, hotels, golf courses and ski resorts.
While all of this was going on, there was still an apparent simmering rivalry between Yoshiaki and his half-brother Seiji. I say apparent because nothing is really clear about their relationship.
Most reports say that they’d barely spoken since their father’s death in 1964, but there must have been some communication between them in the 1970s, because at that time Seiji’s company had incurred debts of $550 million and Yoshiaki rescued his half-brother from ruin, and it is not known whether the help was appreciated or resented.
Seiji’s companies recovered and then thrived, and whatever resentment they may have had towards each other was kept relatively private. But there were small instances where it seemed to bubble to the surface — for example, at Yoshiaki’s mother’s funeral — the one with the Prime Minister in attendance — a blimp reportedly flew overhead publicising a newly opened store belonging to Seiji. Pretty bad form, in fairness.
And while Yoshiaki topped Forbes’ rich list, Seiji appeared in Time magazine as one of Japan’s most influential cultural figures, and there were also glowing reports about his business achievements in business magazines and even The New York Times. Because after the wobble in the 1970s, Seiji not only rebuilt the department store business, he also launched a very profitable credit card business and had invested in a growing portfolio of cultural ventures. And his business had revenues of $28 billion by 1987 — and he had a net worth of $1.8 billion.
The half-brothers were total opposites. Yoshiaki was the hard-nosed one — calculating, relentless.
Seiji was an intellectual, an author, an award-winning poet.
Now, they never spoke publicly about any kind of rivalry. Not once.
But because of that silence, and I suppose because of instances like the blimp at the funeral, and the fact that Yoshiaki had been chosen over Seiji as the heir apparent, people assumed that there was a cold war simmering between them, an animosity just below the surface — and they may well have been right — but we don’t really know. A lot of it is speculation — for example, I could only find one source for that blimp funeral story, so it may not even be true.
Now, friends who knew both men said that it was a love–hate thing. Complicated but loyal — which could be seen when Yoshiaki helped Seiji out in the 1970s.
When reporters asked Yoshiaki about the rivalry, he brushed it off.
“It’s no use comparing us,” he said. “Our philosophies are different, and we are in different lines of business.”
And in fairness, he was right. They were — and for the most part, they kept out of each other’s way.
But that changed in October 1988, when Seiji bought the Inter-Continental Hotels chain for $2.27 billion, instantly planting his flag in Yoshiaki’s domain. It was one of the bubble era’s biggest global deals, splashed across front pages as the moment the intellectual brother went to war with the hard-nosed businessman. The Economist even called it “Brotherly Hate.”
And while it looked like everyone, including Seiji, was spoiling for a very public fight, from my research I got the impression that Yoshiaki just wasn’t very bothered about it — he was far too busy and focused on his own business.
In 1989 he topped the Forbes rich list again for a third successive year, and he also became president of the Japanese Olympic Committee and set his sights on winning the bid for the Winter Olympics in 1998 — which he succeeded in doing.
So as 1990 dawned, he was untouchable: the wealthiest person in Japan, and in the world; the best baseball team in the country; a web of companies employing tens of thousands; head of his nation’s Olympic movement; and, behind the scenes, a level of political influence that reached deep into the country’s centres of power.
Inside Seibu, he was treated like a feudal lord, and here’s a quote from an employee: “He had more power than God.” And he kind of acted like it, too. When he visited his companies, the employees had to line up and bow at precisely the right angle.
Everybody feared him and deferred to him.
He seemed unstoppable, all-powerful — but remember, the Japanese economy had been in hyper-growth for years, and as we all know, economic booms have to end at some stage — and the bigger the boom, the bigger the bust.
Japan’s stock market hit its all-time high in December 1989, but by early 1990 it was crashing. Half its value disappeared within months. And while Forbes named Yoshiaki the world’s richest man again that summer — his fourth straight year at number one — the cracks were showing.
He began selling off peripheral assets, spending on new projects was cut, he told his executives to “tighten our belts” as property sales slowed. Still, to most of Japan, he remained the man who could do no wrong — and in many ways they were right, because despite the Japanese economy tanking from 1990 onwards, Yoshiaki held on regardless.
Through Japan’s Lost Decade, which is what the 90s were referred to, he managed to hold onto his prized assets — and when you look at the Forbes rich lists between 1991 and 1995, he stays in the top five richest people in the world up until 1995 — with an estimated $9 billion fortune, a sizeable drop from $20 billion. And the truth of the matter is, as an article in The New York Times had it: nobody knows whether he is worth $4 billion or $24 billion because his business was shrouded in secrecy.
On a side note, his brother Seiji’s companies struggled when the bubble burst, and after a decade of failed restructurings, he had to sell off most of what he’d built — Walmart actually ended up taking over his supermarket business.
So it seemed like Yoshiaki had weathered the worst of the hangover from that lost decade. I mean sure, he was no longer making the Forbes top ten rich list, but he still had a huge business, he still wielded significant power.
But then in 2004, long-whispered rumours surrounding his empire began to break into public view.
That April, Tokyo prosecutors launched an investigation into his railway companies’ ties with sōkaiya — corporate racketeers who specialised in extorting money from companies in exchange for silence at shareholder meetings. Investigators discovered that senior executives had been paying off underworld figures to suppress revelations of financial misconduct. The scandal exploded. Police raided Seibu’s headquarters, and evidence of “vast corporate corruption” piled up. They found that Yoshiaki had falsified the company’s financial statements to hide just how much control his family held, and that he’d used inside information to orchestrate secret share sales.
The company’s share price fell by 60%, and it was delisted from the stock exchange. Yoshiaki resigned as chairman, taking “moral responsibility.”
And then a year later, March 2005, he pleaded guilty to insider trading and falsifying company records, and later that year he was sentenced to 30 months in prison, suspended for four years, and a fine of 5 million yen — only about $30,000.
And despite the collapse of his companies’ fortunes, he was still a wealthy man — his last appearance in Forbes was in 2006 when they gave him a net worth of $1.2 billion.
While you could obviously say that he got off lightly — it wasn’t a harsh sentence, more a public shaming than a punishment — in Japan, that public shaming is seen by most as the worst kind of punishment. And I’ve always wondered why that is the case — so here’s why: in Japan, to lose face publicly, to be seen as having betrayed the collective trust, it doesn’t just stain your name — it stains your company, your family, even your ancestors. And so this type of public dishonour is seen in Japan as being even worse than any jail sentence.
But in a way, it’s no surprise that Yoshiaki, who revered his father, found himself in this position, because one of the nuggets that I found in my research was a maxim that Yoshiaki’s father had:
“Those who don’t get close to the prison door will never succeed; those who wind up inside failed.”
Well, Yoshiaki obviously took that to heart.
At the time of recording, he’s still alive, 91 years old. It’s hard to know what to make of him.
He was such a private man. No real friends by most accounts. A closed book, even to those who worked beside him for decades.
I’m not a fan of the fear he wielded over his workers. Not a fan of any one individual holding that much power — not just within a company, but within the politics of a country.
Look, I admire the vision. The drive. The way he saw Japan’s leisure economy coming before anyone else did.
And yet, for all that, based on my research, he never seemed to be a happy man. He seems lonely. Driven by a need to appease his dead father — a drive that ultimately led to the worst thing that could befall a businessperson in Japan: total and utter public humiliation.
For one of the world’s most successful businesspeople, the world’s richest man for four straight years, he cuts a tragic figure in the end. But of course, that also makes for a great business story — which brings me to listeners’ emails, and this one is from Michael in California, and he’d love to hear the story of how the iPhone came into being. And Michael, there is such a great story around this — this is a story I really want to dig into in the new year, so keep an eye out for it.
And remember, if you have any comments, any corrections, or any story you’d like us to cover, email me at info@gbspod.com.
All the best, folks.