Inside the relationship of billionaire venture capitalist Josh Kushner and model Karlie Kloss, the power couple with unconventional ties to Trump

Thrive Capital has made some of its biggest investments in tech startups like grocery delivery service Instacart, stock-trading app Robinhood, and insurance company Lemonade, according to PitchBook.

Because of his investments, Kushner sits on the boards for shaving product maker Harry's and wedding planning platform Zola.

The firm has also invested in companies like Instagram, Stripe, and ClassPass.

Kushner's savvy investments have made him a billionaire with a net worth of $3.6 billion, Forbes reported. Thrive Capital is valued at $5.3 billion.

Oscar, which aims to use tech to provide a more consumer-friendly insurance option, secured $375 million from Alphabet, Google's parent company, in 2018. It is now the third-largest for-profit health insurance company in the US, Forbes reported.

Meanwhile, Cadre was valued at $800 million in 2019, according to Forbes. Kushner founded it with his brother, Jared Kushner.

Kloss skyrocketed to prominence as a Victoria's Secret Angel and became one of the highest-paid supermodels in the industry, Forbes reported.

She also runs a free coding camp for girls. In 2015, Kloss started Kode With Klossy, a charity that encourages girls to get involved in coding and tech.

On June 8, 2016, Kloss shared a photo on X, formerly known as Twitter, of her and Kushner revealing that she had met Kushner exactly four years before, placing their first encounter on June 8, 2012, although it's not known exactly how they met.

Their relationship became public when Kushner was spotted on Kloss' arm at a Victoria's Secret Fashion Show after-party in November 2012, Us Weekly reported.

They have tried to keep their relationship relatively private since then.

"It's really refreshing to leave all the fashion shows and shoots and chaos totally behind," Kloss told People magazine.

Elle magazine's Lotte Jeffs asked Kloss if she and Kushner have a "no phones in the bedroom" rule. Kloss answered by shaking her head and saying, "I keep my phone pretty close to me." She added that she tries to digitally detox once a week.

When asked if technology ever causes arguments in their relationship, Kloss "deftly deflects the question," Jeffs wrote.

Kushner is the younger brother of Jared Kushner, son-in-law to former president Donald Trump and former senior White House advisor.

Josh Kushner told Forbes in April 2017 that he and Jared Kushner spoke every day, but refused to comment for an Esquire article about his brother in 2016 because he "did not want to say anything that might embarrass him."

Kloss posted a photo of herself on Instagram in November 2016 filling out an absentee ballot. She included the hashtag #ImWithHer in support of Clinton.

Kushner's spokesperson told Esquire he's a lifelong Democrat and that he didn't vote for Trump.

"It is no secret that liberal values have guided my life and that I have supported political leaders that share similar values," Kushner told Forbes in 2017. 

Kushner told other marchers he was there to observe, The Washingtonian reported.

Kloss also posted a photo on Instagram from the same Women's March, along with an Audre Lorde quote: "Women are powerful and dangerous."

"At the end of the day, I've had to make decisions based on my own moral compass — forget what the public says, forget social media," Kloss told Vogue. "I've chosen to be with the man I love despite the complications."

Kloss also pointed out the sexism in the questions she's frequently asked about her relationship with Kushner. 

"It's frustrating, to be honest, that the spotlight is always shifted away from my career toward my relationship," she said. "I don't think the same happens in conversations with men."

The couple was spotted in March 2018 at the anti-gun-violence March for Our Lives protest in Washington, DC.

Kloss and Kushner didn't hide their presence at the march: They posted photos on Instagram from the March for Our Lives rally. A few weeks earlier, Kushner made a $50,000 donation to the anti-gun-violence group, Axios reported.

"There is a lot of discussion in the Valley about political tests on both who you'll take money from and who you'll work with," the venture capitalist Marc Andreessen told Forbes in 2017. "Having said that, I haven't yet seen an instance of anyone hesitating to take money from Josh because of the affiliation with his brother."

Kushner proposed "during a romantic weekend together in upstate New York," People magazine reported at the time.

"I love you more than I have words to express," Kloss captioned a photo on X announcing their engagement. "Josh, you're my best friend and my soulmate. I can't wait for forever together. Yes a million times over."

Kloss confirmed she had converted to Judaism in a March 2019 appearance on Andy Cohen's "Watch What Happened Live."

The wedding was a small Jewish ceremony with fewer than 80 people in attendance, including Jared Kushner and Ivanka Trump.

"So much love for you both as you begin forever together," Ivanka Trump wrote in a post on X. 

Kloss wore a custom Dior wedding gown with lace sleeves and a flowing train.

"The wedding was intimate and moving," a friend at the ceremony told People magazine. "The couple was beaming with happiness."

Kushner and Kloss' second wedding celebration was held at Brush Creek Ranch, an all-inclusive ranch resort near the Wyoming-Colorado border. The weekend included activities such as horseback riding, paintball, and off-road ATVing.

Photos shared from the wedding show that guests wore Western-themed outfits instead of traditional gowns and tuxedos. Attendees included Diane Von Furstenberg, Orlando Bloom, Katy Perry, Ellie Goulding, Princess Beatrice, and Ashton Kutcher.

Brandon Maxwell, a judge on the fashion design reality competition show, criticized contestant Tyler Neasloney's creation. The assignment had been to design a look for Kloss to wear to a fashion event in Paris, but Maxwell told Neasloney that he couldn't see Kloss wearing the outfit "anywhere."

"Not even to dinner with the Kushners?" Neasloney replied, eliciting gasps from other contestants.

"Keep it to the challenge," Kloss responded. "You really missed the mark here, on all accounts."

When asked about the viral moment on "Watch What Happens Live" with Andy Cohen, Kloss said "the real tragedy of this whole thing is that no one is talking about how terrible that dress was."

She added: "Andy, I'm sure I'm not the only person in this country who does not necessarily agree with their family on politics. I voted as a Democrat in 2016 and I plan to do the same in 2020."

Kloss and Kushner welcomed their first child, Levi, in March 2021.

Kloss revealed her second pregnancy on the red carpet of the 2023 Met Gala while wearing a black Loewe dress designed by Jonathan Anderson. Their son Elijah was born a few months later in July 2023.

Kloss has posted photos of the couple traveling the world and celebrating Kushner's birthday, but she doesn't share much else about their relationship. She also keeps the faces of her young sons hidden in photos.

"I know in my life what really matters to me," Kloss said in an interview with Harper's Bazaar in 2018. "I'm not trying to hide that from the world. I just really like having a more private life."

Kushner and Kloss bought the publication rights to Life magazine through Bedford Media, their media startup that also acquired i-D Magazine. They plan to revive the brand as both a print and digital publication.

"We see Life as an uplifting and unifying voice in a chaotic media landscape," Kloss, who serves as CEO of Bedford Media, said in a statement. "While Bedford is a new media company, we are deeply inspired by Life's iconic legacy and ability to connect diverse audiences with universal narratives of humanity."