How Karlie Kloss went from Victoria’s Secret Angel to multi-million pound angel investor… As she snaps up British fashion bible i-D

The early hours of last Sunday morning at the Delilah supper club inside the Wynn Hotel Las Vegas, where the pillars are marble and gold, the carpets are deep, and the atmosphere decadent. Supermodel Karlie Kloss, 6ft 2in and in a ruched mini dress and high-heeled knee boots, is touring the room with her great friend, the plus-size model Ashley Graham.

The international playboy crowd is here —Leonardo DiCaprio and his film star sidekick Tobey Maguire, singers Justin Bieber and Axl Rose, socialite heirs Balthazar Getty and Brooklyn Beckham, rapper Lil Baby and many more. The DJ is the American record producer Questlove. Behind firmly closed doors, the most fortunate 0.01 per cent is in the mood for celebration following a particularly starry Formula 1 Grand Prix.

But Kloss, 31, has more cause to clink champagne flutes than most. For the former Victoria’s Secret model has just bought the bi-monthly British fashion publication i-D from Vice Media Group, months after the company filed for bankruptcy.

The acquisition, through her company Bedford Media, comes three years after she and a group of other high-profile investors, including fellow model (and daughter of Cindy Crawford) Kaia Gerber, bought W, the high-end glossy fashion magazine.

Indeed, the woman we mostly associate —fairly or not — with a glamorous party lifestyle and a controversial lingerie company is now, it would appear, becoming an influential media mogul.

At first glance i-D is not an obvious fit. Founded by designer and former Vogue art director Terry Jones in 1980, the magazine made its name as the home of Britain’s post-punk anarchic street style. At the height of i-D’s fame in the early 1990s, all-American Kloss, who grew up in the Mid-West state of Missouri, was a babe in arms.

Yet in recent years, i-D’s following has dwindled and Kloss has spotted what she believes is a prime business opportunity. In a statement, Vice Media Group bosses said they have high hopes she can now save the magazine. ‘She has a deep passion for technology and the intersection of fashion, media and culture on a global basis, and we believe that the brand is in great hands to continue to build on its important position in the fashion world and to continue the growth trajectory we see for the business,’ they said.

Clearly Kloss, who now becomes the CEO, thinks she can breathe enough life into the edgy brand to make it worth her while.

Karen North, a professor of communication at the Annenberg School for Journalism, says it’s an increasingly common tactic in the world of the super-rich. ‘What’s happening is that people with the means are finding things they care about and deciding to rework them so they stay alive — and it’s not just traditional businessmen with the means any more.’

Kloss, indeed, is just one of a new breed of female entrepreneurs who have made their fortunes in entertainment and/or fashion and now seek to build empires elsewhere.

From actresses Gwyneth Paltrow and Sofia Vergara to pop star Rihanna, celebrity businesswomen are flexing the power amassed by their high public profile and huge personal bank balances. Worth £32 million in her own right and married to venture capitalist Josh Kushner — brother of Jared, the husband of Ivanka Trump — who’s worth a cool £3 billion, Kloss has form for making counter-intuitive, but potentially very clever, investments. 

Recently she launched a venture selling digital clothes to avatars in Roblox, the online gaming platform beloved of pre-teens worldwide. The older generation may shrug their shoulders, but it’s part of an industry worth billions — and she wants in.

Kloss has made a dozen more investments, too, each worth close to or more than £1 million, in companies that have caught her eye. This spring, for example, it was announced she was an investor in a new nappy firm called Coterie. Now a mother of two, she came across the company when expecting her first baby Levi, in 2021, did her research, and decided this was a business which could turn a profit. Her second son, Elijah, was born this July.

Indeed, Kloss has been investing since she was 21. ‘I’m an optimist. When I see a problem, I see it as an opportunity to solve something,’ she told Forbes magazine.

‘I feel very entrepreneurial, I love business, I love meeting entrepreneurs who are building interesting things. I think my first angel (investment) cheque that I ever wrote was to a company with a product that I originally had an idea to start.

‘I really thought long and hard about it, and thought I’d rather invest in them because I believe so deeply in the problem that they’re trying to solve, and I think they can do it better than me.’ (That product was an organic tampon delivery company called Lola.)

Unlike Gwyneth Paltrow, who has built her empire on ‘curating’ recommendations for products mostly made by others, under her own umbrella brand Goop, Kloss has not yet sought to unify or personalise her portfolio. Her highest profile venture outside modelling was the Kode With Klossy non-profit platform which she set up in 2015 to try to get more girls into computer coding via scholarships and summer camps.

Neither does she have quite the same ‘goody two shoes’ air about her as Paltrow.

On the one hand she is a serious businesswoman who is outspoken on any number of hot topics in the U.S., campaigning for reproductive rights and gun control and stating her admiration for Hillary Clinton (despite her brother-in-law’s direct link to Donald Trump).

On the other, she is the party-loving queen of the private jet set. Her closest pals are Katy Perry and husband Orlando Bloom, designer Diane von Furstenberg and her billionaire husband Barry Diller. She’s also besties with Princess Beatrice and singer Ellie Goulding, having met both on the arty New York social scene.

She hangs out with Amazon billionaire Jeff Bezos and his fiancee Lauren.

More controversially, having fallen out with former close friend Taylor Swift, she is now good pals with super-successful music manager Scooter Braun, who infamously acquired the rights to Swift’s back catalogue.

Kloss has also courted controversy for posting support for Israel to her near 13 million followers on Instagram and sparking a wave of criticism, as she must have known it would. Kloss converted to Judaism just before marrying Kushner in 2018.

In an interview she said: ‘Changing part of who you are for someone else can be seen as weak, but you know what? Actually, if you’ve been through what I’ve experienced, it requires you to be anything but weak.

‘It requires me to be stronger and self-loving and resilient. I really did not take this lightly. It wasn’t enough to just love Josh and make this decision for him.

‘This is my life and I am an independent, strong woman. It was only after many years of studying and talking with my family and friends and soul-searching that I made the decision to fully embrace Judaism in my life and start planning for a future with the man I chose to marry.’

She and Kushner had two weddings, both suitably starry. For the first, in New York, she wore bespoke Dior, while the second, at the luxury Brush Creek Ranch in Wyoming, was cowboy themed. Home is a colossal £33 million penthouse in New York, while there is also a mansion on the water in Miami, Florida, worth more than £16 million.

That super-prime life is some distance away from her middle-class origins. One of four daughters, Kloss was raised in St Louis, Missouri, by Tracy, an independent filmmaker, and Kurt, a doctor.

Though Karlie herself had dreams of studying medicine, she was ‘discovered’ at a charity fashion show aged 14 and started a modelling career that has so far included 42 Vogue covers and countless advertising campaigns for brands including Chanel, Donna Karan, Dior and Nike.

But it’s been hard for her to shake off her image as a Victoria’s Secret Angel. When she joined in 2011 aged 18, she was the first model ever to be given her angel wings — actual wings that only the company’s top models wore for the annual show — and her extraordinary figure made her one of company’s biggest stars.

By 2015, however, she was clearly questioning her day job, explaining that it was at odds with her feminist principles. Indeed, not long afterwards, the lingerie powerhouse was embroiled in a MeToo scandal with employees complaining of misogyny, bullying and harassment by two senior male executives.

Kloss, meanwhile, had enrolled at New York University to study feminist theory. She said at the time: ‘The reason I decided to stop working with Victoria’s Secret was I didn’t feel it was an image that was truly reflective of who I am and the kind of message I want to send to young women around the world about what it means to be beautiful. I think that was a pivotal moment in me stepping into my power as a feminist, being able to make my own choices and my own narrative, whether through the companies I choose to work with, or through the image I put out to the world.’

It was a brave statement, though many might argue Victoria’s Secret’s less than feminist credentials were glaringly obvious from the start.

And marrying into the Kushners hasn’t been easy. While she denies it, there was reportedly pressure from her husband’s wealthy Jewish parents for her to convert.

Then there’s the matter of Josh’s father Charles having been jailed in 2005 for making illegal campaign contributions to the Democratic party and for tax evasion.

During his trial, in details so murky you can’t help but feel for the woman joining such a family, he also pleaded guilty to witness tampering after hiring a prostitute to seduce his brother-in-law, record the encounter, and send the tape to his sister. Charles was sentenced to two years in prison.

Further family awkwardness was caused by the Ivanka-Jared marriage. The two power couples seemed to be on good terms until Donald Trump got into the White House, at which point the political differences between the Kushner boys became glaring.

Josh’s investments include a health insurance company which is structured around the Obamacare system that Trump wanted to dismantle. He and Karlie campaigned against gun ownership, with Karlie holding a sign reading ‘Load Minds Not Guns’. She also openly supported Joe Biden against Trump in the 2020 American presidential election.

‘It’s been hard,’ she admitted to Time magazine. ‘But I choose to focus on the values that I share with my husband and those are the same liberal values that I was raised with and that have guided me throughout my life.

‘Looking back at my late teens and early 20s, I think I was fearful that I would lose a job or lose my position if I said I didn’t want to do something.

‘But I did not lose out on jobs. If anything, the more I exercised the power of my voice, the more I earned respect from my peers. And I earned more respect for myself. Only now do I have the confidence to stand tall — all 6ft 2in of me — and know the power of my voice.’

Now that she is the CEO of her own fashion magazine, and a British one to boot, we can expect to hear rather a lot more of it.