Money makers: the punk drop-out who made a billion

Yusaku Maezawa © Rex Features
Yusaku Maezawa: “I wanted to derail myself”

“The trains I took every morning were jam-packed with salarymen. They looked so tired and unhappy,” Japanese billionaire Yusaku Maezawa, 42, tells Richard Lloyd Parry in The Times. “My first year I worked hard, but after that school began to seem meaningless… I could see the rails stretching in front of me – school, university, career. I could picture myself as one of those people jam-packed in a rush-hour train. I wanted to derail myself.”

So the young Maezawa dropped out of school, worked on building sites and formed punk band Switch Style. In 1998 the band signed a recording contract that would lead to three albums. It was also the year Maezawa started his business, Start Today, named after the album of an American band he liked. It began small, selling CDs, vinyl and T-shirts to friends, but steadily grew, and by 2000 it was selling online. Maezawa left the band to focus on the company, and today retains a 38% stake. “I don’t know my personal worth,” he says (Forbes puts it at £2bn). “I don’t even have a bankbook… As far back as I can recall, my bank balance has been close to zero, because whatever money I have, I spend.” And spend he does.

In May 2016 he paid $110,487,500 for Untitled, the 1982 painting by Jean-Michel Basquiat. He then surprised many in the art world by posing with the painting on social media, drawing criticism for his “cheap taste in art”. But Maezawa can afford not to care and he has made good on his promise to exhibit the Basquiat artwork around the world. Now he’s building a gallery to house the rest of his impressive art collection.

The furniture business that grew out of a trip to India

In 2012 Debbie Williamson went to India to find a supplier for Swoon, her online furniture business, says the BBC’s Sarah Finley. “I hung out in every cafe, and spoke to local businesses – I wanted to find out which supplier manufactured a French armchair I’d had my eye on at home,” she says. The chair was selling for £1,300 in Britain, and Williamson reasoned that must be a massive markup.

In Britain, she joined with Brian Harrison (both had worked for the Telegraph Media Group), and they invested £10,000 each to fill a shipping container with French armchairs. “We put an advertisement in The Daily Telegraph, hoping we’d get a few orders,” says Williamson. “By the end of the next day we’d sold the whole container.” The pair have learnt to try selling a few examples of any particular design first in case they don’t sell. “Buying a shipping container full of a product that no one wants is a bad idea,” as Harrison points out. Today, Swoon turns over £20m a year, with 100 staff in London, India and Vietnam.

The bet that paid out $30bn

“I want you to know how risky this is, because I want to come home at dinner for Thanksgiving and I don’t want you to be mad at me,” Jeff Bezos told his parents in 1995. Jackie and Mike Bezos were about to put $245,573 into their son’s start-up venture – an online retailer called Amazon. “He’s probably now welcome to extra helpings of turkey — and all the gravy,” says Bloomberg’s Tom Metcalfe. One stockmarket listing and three stock splits later, his parents’ stake could be worth almost $30bn today, making them wealthier than Microsoft‘s co-founder Paul Allen.

Bezos’s parents’ holdings haven’t been publicly disclosed since the end of 1999, and between 2001 and 2016 they are known to have donated 595,027 shares to the Bezos Family Foundation. Assuming they haven’t sold anything else, the pair would own about 16.6 million shares, making them Amazon’s second-biggest shareholders after their son. Their total return would be about 12,000,000%, “a performance that would make even the most celebrated venture capitalists blush”, says Metcalfe.

Getting down and dirty with yoga


Khloé Kardashian © Getty images
Khloé Kardashian: catering to the average woman

“It blows my mind to think that the average woman in America is a size 16 [UK size 18] and that no one is catering to her,” Khloé Kardashian, 34, tells Carolyn Asome in The Sunday Times. “I’ve always been compared to my sisters [such as reality TV star Kim], who I will never look like, so it was really personal to me to create a clothes range that caters to all sizes.”

To achieve that aim, Kardashian (pictured), whose net worth Time magazine puts at $40m, teamed up with Briton Emma Grede, 35, who has a background in entertainment marketing and is married to the Frame Denim co-founder, Jens Grede, to launch Good American. The fashion company started selling denim in 2016, taking $1m on its first day, before launching its Performance range of casual sportswear online and in Selfridges.

Kardashian and Grede hope to address the oversights made by other well-known brands in the “athleisure” market. “There are billion-dollar brands that still don’t perfect their performance wear,” says Kardashian. “They test on machines instead of people; whereas Emma gets women into the design studio to do squats or bend over, and then she asks other women to see if they are revealing anything — we can get down and dirty over here.” Grede agrees. “I think we’ve all been in that yoga class where the person in front of us is showing too much,” she says. A pair of the brand’s Electric Feel leggings costs £124. “We want to showcase real women with real lives and highlight their differences,” says Grede. “Hopefully Good American has a lot to do with a shift in the fashion industry.”