There's an awkward moment from a 2020 episode of "Project Runway" that perfectly captures the tightrope walk Josh Kushner and Karlie Kloss have been doing for years. Contestant Tyler Neasloney, trying to save his failing design, asked supermodel host Kloss if she'd wear his dress to "dinner with the Kushners." It was a cheap shot—less about fashion and more about Kloss's politically contentious in-laws.

Neasloney apologized, claiming "no hidden agenda," but the damage was done. The moment illustrated just how tricky it is being married into one of America's most prominent Republican families when you're actually a Democrat. Yet somehow, Kloss and her husband Josh Kushner have managed not just to survive that scrutiny, but to thrive despite it—building a personal and professional empire that's actually more successful than fellow billionaire and Trump son-in-law Jared Kushner's.

The Venture Capitalist Who Made His Own Fortune

Josh Kushner isn't riding on his family's real estate coattails. His identity in the business world comes from his own sharp instincts as a venture capitalist. After founding Thrive Capital in 2009, he made prescient early bets on companies that became household names: Instagram, Spotify, Slack. Those calls turned out pretty well.

According to Forbes, Thrive now manages a staggering $25 billion in assets. A January 2023 funding round valued the firm itself at $5.3 billion, pushing Kushner's personal net worth to $5.2 billion—more than his brother. That makes him one of the wealthiest young people in the country, and he did it on his own terms.

Here's what's interesting: being Jared's brother hasn't hurt Josh's business. While Jared served in the first Trump administration, Josh kept closing deals. Marc Andreessen, the legendary investor, told Forbes back in 2017: "I haven't yet seen an instance of anyone hesitating to take money from Josh because of the affiliation with his brother." Jared has no official role in the second Trump administration, but the point stands—Josh's venture capital success operates in a different universe from his family's political entanglements.

Family Drama Behind Closed Doors

The political differences might be just the tip of the iceberg when it comes to family tension. According to journalist Vicky Ward, author of "Kushner, Inc.," Josh's relationship with Kloss was apparently a major source of conflict within the family, Town & Country reported in 2021.

Ward alleged that family patriarch Charles Kushner told Josh that Kloss was "not the right person," with sources pointing to her not being Jewish at the time as a key issue. Jared allegedly agreed. According to Ward's sources, the Kushner family even banned Josh from bringing the Victoria's Secret model to family holidays.

The book suggested the family viewed Kloss as lacking the right pedigree—certainly not "real estate royalty" like Ivanka Trump. It's a portrait of family disapproval that adds another layer to understanding why Josh and Karlie have carved out such a deliberately separate identity.

Drawing Political Lines in the Sand

The "other" Kushner couple hasn't been subtle about their politics. In 2016, Kloss publicly backed Hillary Clinton, while a spokesperson for Josh told Esquire he was a "lifelong Democrat" who didn't vote for Trump. They've put their money where their mouths are, too—Kushner donated $50,000 to gun control efforts at the 2018 March for Our Lives, according to Axios.

That said, navigating these waters requires finesse. Kloss addressed the "complications" in a 2018 Vogue interview, saying: "I've had to make decisions based on my own moral compass—forget what the public says, forget social media. I've chosen to be with the man I love despite the complications."

Their political contributions tell the same story. Federal Election Commission data from the 2024 election cycle shows Kushner contributed $250,000 to the Growth Democrats PAC, while Kloss made significant donations to several Democratic congressional campaigns. They're walking the walk.

Building Their Own Power Brand

Through a decade together, three children and one of the most polarizing political eras in American history, Josh Kushner and Karlie Kloss have built something remarkable. They've assembled a multibillion-dollar financial portfolio and a growing media empire, all while maintaining a public identity as committed Democrats.

The real story here isn't about the famous family they're connected to by blood and marriage. It's about how they've deliberately built their own powerful brand—one that's worth more, both financially and reputationally, than trying to coast on family connections. In a world where the Kushner name carries serious political baggage, Josh and Karlie found a way to make it mean something entirely different.