Now, I'm not into fashion and I really didn't know anything about Klein before I did my research for this episode, and I found him to be such a fascinating character — how he, together with Ralph Lauren and Ann Klein, no relation, dragged American fashion out of the shadow of Paris and made it stand on its own two feet; how he didn't do it on his own — Calvin Klein the business was always two people — Klein and Barry Schwartz; how Klein pioneered designer jeans; how he built his company while partying in Studio 54 and burning the candle at both ends; and how the business was just days from bankruptcy before David Geffen came to the rescue. Also, his marketing genius — he was behind some of the most controversial and influential ads of the 1980s and 90s. He makes for a cracking story. Enjoy.

Calvin Klein was born on November 19, 1942, in the Bronx, New York. His father, who had a grocery store, was an immigrant from Austria-Hungary — current-day Ukraine. But it was his mother and grandmother who had the biggest influence on Klein.

He describes his mother as having an intense appreciation for design and tailoring. She specifically liked beige, cream, white, and brown colours — as a result, Klein said that he spent the first ten years of his life absorbing these colours, laying the foundation for what would become his signature minimalism. Then his grandmother ran a seamstress shop in the Bronx, and she taught Klein how to draft, choose fabric, and alter a garment properly. So while other kids on the street were playing sports, Klein was sketching designs and sewing.

His father, mother, and grandmother all instilled in Klein a huge work ethic. "I came from a family in which all they did was talk about work."

When he left school, Klein went to the Fashion Institute of Technology, graduating in 1963. And crucially, when the top FIT graduates were heading to Paris for haute couture apprenticeships, Klein didn't go. He stayed in New York because he believed that his aesthetic was fundamentally American — so he had a vision of what he wanted to make from the get-go.

He started working in various fashion businesses in New York but he wasn't enjoying it. A lot of his work entailed copying collections that came from Paris — so while this gave him technical exposure at a high level, he didn't like just copying. He wanted to design his own things.

Now, he got married in 1964 to a textile designer — just a year out of college, when he was 21 and she was 20 — way too young, in fairness. Their daughter Marci was born in 1966, and when you combine the pressure of young fatherhood and providing for his family, together with the fact that he wasn't enjoying his work, Klein was at a bit of a crossroads. And this is when the second most important person in this story comes into play — Barry Schwartz.

I had never heard of Schwartz, because he's a very low-profile guy. Schwartz and Klein had been best friends since they were five years old — both of their fathers ran grocery stores. Schwartz had been in the army but had to return and run the family store when his father was murdered in a robbery at the store in 1964, when Schwartz was 21.

So when Klein spoke to Schwartz about his frustration with his design career, initially Schwartz proposed that they start a grocery business together and open up loads of stores.

Fortunately, Klein also went to his parents for advice. Klein expected that his father, who was the practical, hard-working shopkeeper, would advise him to go with Schwartz's plan, and that his mother would recommend he stay in the fashion business — but that's not how it worked out. His mother said nothing. His father did all the talking. And here's a passage from an excellent Vanity Fair article on Klein that was a great resource for this episode: "His father advised his son to stay the course, and see his fashion vision through. Otherwise, he'd be sorry. Calvin recalls the conversation as the best advice anyone has ever given him. 'What he was really telling me is it's not about money. It's about being happy and feeling good about what you're doing. I just sailed out of there.'"

God, fathers can surprise you sometimes, can't they? I love that story because it pretty closely resembles the few times I ever asked my dad for advice — because whenever I did, he surprised me, just like Klein's father did. I don't know why I never asked my father more often for advice.

Anyway, Klein took his father's advice, turned down Schwartz's offer, but did ask him for money to help fund his first designs. Schwartz immediately gave him $10,000 — about $100,000 in today's money — so a huge gamble. But as Schwartz said of Klein: "I always believed in him — it was pretty easy to believe in him, because he's a pretty impressive guy."

And Klein must have been a very impressive figure. Here's what Barry Diller had to say of him: "In any place, in any business — in anything — Calvin would succeed. With him it's a force of curiosity and willfulness."

December 28th, 1967, Klein incorporated Calvin Klein Ltd. with Schwartz as a fifty percent silent partner. He wasn't involved in the business quite yet — he was still running his grocery store.

Now, Klein stayed working at his day job; he needed the security and the money. He was working on his own small collection — just six coats, three dresses — every night and at weekends. But then his boss found out about his double life. Klein is quoted as saying: "I felt terrible. I had a contract with them, and I was close to one of the owners, and I betrayed them. They asked me to leave immediately, and I did."

So now, in early 1968, Klein was operating out of a small showroom in the York Hotel on Seventh Avenue.

And then came a stroke of luck — a massive stroke of pure luck. What happened was a guy called Donald O'Brien, the merchandise manager from Bonwit Teller, one of the premium luxury retailers back then, was visiting an established designer in the same building as Klein, but the elevator opened on the wrong floor — it stopped on Klein's floor. O'Brien stepped out, saw Klein's work, and loved it. He told Klein to bring the collection to Mildred Custin, the president of Bonwit Teller and one of the most powerful fashion retail figures in America.

Again, from the Vanity Fair article: "The next part of the story is firmly entrenched in fashion lore. Instead of taking his goods in a taxi, which might have led to the clothes becoming creased, he put everything on a rack and wheeled it himself, from Seventh Avenue and 37th Street to Fifth Avenue and 56th Street — a distance of nearly a mile and a half. 'This way everything could be perfect,' he remembers. ('Perfect' is a word that comes up a lot with him.)"

Custin loved his designs as well. So what was it about Klein's designs that O'Brien and Custin loved?

Well, for context, the 60s was a time of huge cultural upheaval, and American fashion was still heavily influenced by European and especially French style. But at that time, the fashion coming from France was loud, chaotic, very experimental. And here you had Klein with these beautifully tailored wool coats and simple dresses. Klein had the vision — he was betting that underneath all the cultural upheaval, women wanted finely tailored, simple but classic clothes. And he was right. This was Klein's DNA from the get-go — what was described as stripped-down elegance paired with a bold, modern attitude.

Custin was also impressed with Klein's confidence, the way he presented, and just his overall persona: "He is down to earth, direct, and has an easy sense of intimacy. He also has a seductive boyishness, not to mention good looks, cool, and a magnetism that attracts both sexes."

And even if you look at photos of Calvin Klein from his younger days, he was very cool.

So Custin placed an order of $50,000 on the spot — but she also insisted on exclusivity. Klein refused, which shows a level of confidence and bravery — this was his first big order, but he insisted that he could sell to other retailers. And Custin relented. He got what he wanted. As a result, he got large orders from other major retailers, and in its first year of operation, the company grossed a million dollars.

Now, also in 1968, following the assassination of Martin Luther King Jr., riots broke out across American cities. Schwartz's grocery store in Harlem was destroyed. So Schwartz decided to go full time into the fashion business. He invested another $25,000 to ensure they could fulfill the orders that were coming in, and he took over the business side of things.

This freed Klein from the financial side entirely, which meant he could just design. And that division is what made the company work. As Schwartz said: "It was the ideal partnership because we didn't compete."

So with this initial success, a buzz was starting to build around the label. In 1970, Klein produced his first formal runway show and the fashion press in the US loved it. By the end of 1971, the company had hit $5 million in annual sales. In 1973, Klein won his first Coty Award — the Oscars of the fashion business. He was thirty years old, the youngest designer ever to receive it.

Also in 1973 — and this is crucial — he pivoted and changed from wool coats and formal dresses to casual, everyday clothes like relaxed blazers, comfortable pants, and simple sweaters. This was the emergence of what was called luxury sportswear, casual chic. This was very much a time when American fashion was starting to break free from its traditional French and European influences, and Klein, together with Ralph Lauren and Ann Klein, no relation, were leading the charge. The timing was perfect — the market was ready for what they had to offer.

But Klein was working 18-hour days, often sleeping in his showroom, and so his marriage ended in 1974.

By the end of 1975, revenues had reached $17 million, and Vogue said: "If you were around a hundred years from now and wanted a definitive picture of the American look in 1975, you'd study Calvin Klein."

But by 1977, Klein's social life had become hectic and very public. This all coincided with the burgeoning and hedonistic nightlife scene in New York at that time, which was perhaps best exemplified by Studio 54, which opened in 1977. And it was really with Studio 54, and all of the publicity, paparazzi, and crazy stories that surrounded it, that Klein emerged as this fashion icon. He was appearing in photos with all of the hottest celebrities, like Andy Warhol and Bianca Jagger, and I recommend you Google Calvin Klein Studio 54 — he looks so stylish and so cool.

Again, from the fantastic Vanity Fair article, in relation to Klein and Studio 54: "The club, where the creativity and license that were coursing through the 1970s flowered, seems to have been made for him. For a few years, the disco was the nerve center for New York's fashion, art, and entertainment worlds."

And as Klein himself said: "It was an amazing time in New York City. Everyone from all walks of life, from any part of the world — I had the opportunity to meet them and get inspired by the way people looked or by what they did."

So while Klein drew inspiration from those wild nights, he also picked up a pretty big coke habit, as he has said: "I burned the candle at both ends. When you're young you can do that to a certain degree. The thing is, we were successful. We managed to be very high-functioning people."

And that's the thing about Klein — for a few years, until he eventually went into rehab, and he ended up going to rehab a few times, he was still able to work and produce the goods. As the photographer Bruce Weber said: "He could be out all night and might not go home, but he was in that office, on time, ready to go."

Even so, by burning the candle at both ends as well as having a drug addiction, life becomes very chaotic. So it's hard to even imagine how, in the middle of all of this chaos, Klein dealt with what must have been the most traumatic event in his life.

Because in February 1978, his 11-year-old daughter was kidnapped by her former babysitter and two accomplices. A ransom of $100,000 was demanded. The actual exchange was straight out of a Hollywood movie. A terrified Calvin Klein had to walk into the bustling Pan Am Building in Midtown Manhattan carrying $100,000 inside a brown paper grocery bag. He took the building's main escalator and dropped the bag on the steps at a particular location. But the kidnappers were complete amateurs, and what they didn't realise was that the entire lobby was crawling with undercover FBI agents tracking Klein's every move. So they were caught quickly and Klein's daughter was released. All three kidnappers were sentenced to 8.5 to 25 years in jail. That must have been such a harrowing experience for Klein.

Anyway, back to Studio 54 — because it was there, in the late 70s at four in the morning, that Klein came across an opportunity that catapulted the brand into the mainstream. A guy danced up to him and asked Klein, "How would you like to put your name on jeans?" This concept of designer jeans was pretty new back then — and even though the music was blaring, as Klein himself said: "When it's about the work and the business, I don't miss it. I thought this could really be interesting."

So that morning, after Klein gets into the office from Studio 54, he asks Schwartz to contact the jeans guy, who worked for a company called Puritan Fashions, and they struck a deal. The agreement gave Puritan the exclusive licence to manufacture and distribute Calvin Klein Jeans.

Within the first few weeks of launch they were selling 200,000 pairs per week. And sales increased massively when the hugely controversial TV ads featuring a then 15-year-old Brooke Shields were released in 1980. Critics argued that they were overtly sexual and exploitative of a minor. Now, personally speaking, I don't have any problem with most of Calvin Klein's ads — he's in the fashion business and sex sells — but using a 15-year-old in a sexualised context, that's not good. Several TV stations banned the ads outright. Conservative groups called Klein a child pornographer. The backlash was enormous. And of course the jeans sold out everywhere — at their peak they were selling 500,000 pairs per week.

By this stage, we're in 1981/82, and the brand's total global retail sales were hitting $750 million. But what's crucial to understand here is that Klein's actual business was really a highly profitable licensing operation. They charged other companies a 7% to 8% royalty fee just to use the brand name. They had very little overhead, and Klein and Schwartz's personal income in 1981 was $8.5 million each.

And the growth and brand exposure just kept increasing in 1982 when Klein launched his men's briefs — with the ad campaign showing Olympic pole vaulter Tom Hintnaus in nothing but white briefs against a whitewashed wall. The Times Square billboard reportedly caused rear-end collisions as drivers slowed down to look. Teenagers used crowbars to break open bus shelter casings to steal the posters. The underwear line became an immediate cash cow, while the ad campaigns also, of course, amplified the brand.

By 1982, Calvin Klein Jeans had become a commercial juggernaut. But while the manufacturer, Puritan Fashions, was pulling in $250 million in wholesale jeans sales, Calvin Klein's company was only taking home about $15 million of that in royalty checks. Wanting a bigger piece of the pie, Klein and Schwartz bought Puritan outright in 1983 for over $60 million.

But now they were entering a totally new world. They were moving from a hands-off approach where they simply controlled design and marketing, to suddenly owning a massive manufacturing business. Now they had to manage a huge labour force, fabric costs, warehouses, and mountains of unsold inventory.

To make matters worse, the buyout happened at the exact moment the American designer jean market began to cool. Within a year, this new manufacturing arm posted a loss of $11.3 million. To keep the company from going under, they had to refinance their debt by issuing $80 million in high-interest junk bonds through Michael Milken. It was a perfect storm: they went from making effortless profits from royalty checks, to bleeding cash on factories, machinery, and wages — all while that high-interest junk bond debt compounded in the background.

With the jeans business in big trouble, the brand's survival fell on its fragrance business, which really came to the fore — first with the launch of Obsession in 1985. The men's aftershave came out a year later, in 1986. It's still one of my favourites — for the last 30 years I've just used Obsession and Fahrenheit. Man, I'm so stuck in my ways.

The launch of Obsession was backed with a $13 million advertising campaign — the print ads featuring nude bodies again resulting in huge condemnation from conservative groups, and again sales went through the roof. As did the sales for Eternity, launched in 1988. So these successes provided the company with a bit of a financial cushion — but the overall business was still in trouble. The payments on those junk bonds were crippling the business. The banks refused to advance additional credit, and by 1992 the company was about to default and looking at bankruptcy. And this was happening at a time when Klein was back in rehab in Arizona, having relapsed after being clean for several years.

But the company was saved just weeks before the default deadline by one of Klein's best friends, David Geffen, who had sold his record company just two years earlier, walking away with $700 million. He lent Calvin Klein $62 million, no strings attached. As the New York Times wrote at the time: "Geffen is the kind of friend many businessmen could use during this recession." His help gave the company much-needed breathing room.

While all of this financial trouble was going on, Klein had gotten married again — and I know that might surprise a lot of people, because for the last 20 years or so Klein has been dating men. The reason I bring this up is because I already mentioned how New York's vibrant nightlife helped inspire Klein, because like all great creatives, he drew inspiration from his personal life and his lived experience. Here's a quote from the Vanity Fair article: "I've fallen in love with women. I've married women. And I have a family. I have experienced lots of things that have influenced my world. I am, for good or bad, a real example of whatever I've put out there. It's not something where we tried to say, well, let's outdo the other people and see if we can be more outrageous. It was real."

And while I can't really comment on his fashion, because I just know nothing about fashion, I believe his marketing was so good because it was inspired by the lifestyle he was leading, combined of course with his own instincts, his creativity, and originality. It wasn't contrived — it was intrinsic to who he was. And while much of his marketing playbook has been copied so many times over the years, at the time, Calvin Klein ads were so original, so authentic — that's why it worked so well.

Anyway, having stabilised the business in the early 90s, 1993 saw the launch of the CK brand — a lower-priced, youth-oriented line. It was a huge hit. The New York Times said it "looked like an incubator for everything exciting in street-level fashion."

In 1993, revenue hit $1.5 billion, $5.1 billion by 1997, and approaching $6 billion by 2000. By this stage they had sold the jeans manufacturing business and they were back to being a licensed business — with the company handling just design and advertising.

To maintain the illusion of a traditional luxury brand, they had these ultra-minimalist flagship stores on Madison Avenue, Paris, London, and Tokyo. These stores barely broke even — but that wasn't the point. They were physical billboards, promoting the brand's luxury prestige.

But then in 2000 they hit serious trouble with one of their biggest licensing partners — a company called Warnaco, who held the licences for their jeans and underwear. Here's what happened. Warnaco were in huge debt and under pressure to shift volume fast. So what did they do? They started dumping Calvin Klein jeans and underwear directly into high-volume retailers — places like Costco and BJ's Wholesale.

And to Klein, that was an absolute nightmare. Because the whole point of the brand — the premium positioning, the aspirational image he'd spent thirty years building — depended on where the product was sold. By sticking it alongside bulk toilet paper in Costco, that was so damaging for the brand.

So Calvin Klein Inc. filed suit against Warnaco for breach of contract, trademark dilution, and brand equity degradation. And it got very public. Klein went on Larry King Live and compared what Warnaco were doing to counterfeiting.

The case was settled in January 2001. Warnaco kept the licences but agreed to strict limits on mass-channel sales. However, for Warnaco, the legal costs, on top of their existing debt, pushed the company into Chapter 11 bankruptcy in June 2001.

But this whole case had exposed something much bigger. The licensing model that had made them so wealthy had also made them very vulnerable — to partners over-distributing the product, to quality drift, to expensive legal wars that were messy and damaging. Klein and Schwartz were in their sixties. They'd been running this company since 1968. The whole thing was still privately held. They came to the conclusion that it was time to sell.

In February 2003 they sold the company to Phillips-Van Heusen — PVH — for $430 million. Now, PVH also owns Tommy Hilfiger and, interestingly, it had been founded in 1881 selling shirts to Pennsylvania coal miners — they might be worth doing an episode on at some stage.

Schwartz took his 50% — $215 million — and walked away completely, retiring to focus on his great passion, thoroughbred horse racing. Klein got his $215 million upfront and worked with the brand up until 2006. Plus, because they were obviously going to continue to use his name, he also had a 15-year earnout based on global sales, which ultimately brought his total to somewhere in the region of $865 million. By 2025, global retail sales of Calvin Klein products were running at just under $9 billion.

So where do I stand on Klein? It's hard to overstate the impact Klein has had — not only on fashion but also on culture. He helped shift American fashion out from under the shadow of Paris and establish its own identity. Alongside people like Ralph Lauren, he helped define what modern American style looked like — clean, simple, confident, and understated.

He turned designer jeans into a global phenomenon, men's underwear from something nobody thought about into a fashion category of its own, and created an advertising playbook that influenced virtually every fashion brand that came after him. You can argue about some of the campaigns, and some of them rightly deserve criticism, but there's no denying that his marketing was powerful and truly original.

And what I like about Klein the person is his authenticity, his vulnerability, and his honesty. He never hid from who he was. The New York nightlife, the relationships, the struggles with addiction — he was open about all of it, and then all of that fed directly into what he created.

And this openness and honesty made him a good boss. Yes, he was a perfectionist and obsessive about details, but the overwhelming impression I got was that people genuinely liked him. Here's how one former executive described working with him: "We were all in love with Calvin, as were all the editors. He was the most seductive person. You wanted to please him. Men, women, everyone."

In short, Klein is probably one of the most significant fashion and cultural icons of the last 50 years, and he makes for a fascinating story.

And that brings us to listeners' emails, and this one comes from Ali, who would love to hear the story of Ben and Jerry's — great recommendation, Ali, thanks so much. And remember, if you have any comments, any corrections, or any story that you'd like us to cover, email us at: info@gbspod.com

All the best, folks.