Perhaps no modern presidential son-in-law in-waiting has been more in the spotlight than Jared Kushner. The “de facto campaign manager,” and a key member of the transition team, Kushner is reportedly angling for a position in the Trump administration.  But here’s something you might not know: Jared Kushner’s younger brother, Joshua, is the cofounder of a startup trying to capitalize on the Affordable Care Act — which Donald Trump has vowed to move quickly to dismantle.  Josh Kushner is a 31-year-old venture capitalist on the fast track. He’s been called “a modern-day Vanderbilt,” “the boy wonder VC,” and “your mother’s dream man.” He’s dating supermodel Karlie Kloss — Taylor Swift’s best friend — who posted a photo of herself on Instagram voting for Hillary Clinton, with the hashtag #ImWithHer.” (Josh Kushner reportedly didn’t vote for Trump either.)  If that’s not awkward enough, Josh Kushner counts Peter Thiel, the contrarian Silicon Valley venture capitalist, among his loyal investors.  Thiel, you’ll remember, donated to Trump’s campaign, spoke at the Republican National Convention, and now sits alongside Jared Kushner on the Trump transition executive committee.  Changes to the Affordable Care Act seem certain, and they will surely affect Kushner’s startup, Oscar Health, which sells individual policies to customers in several states.  Oscar Health is in many ways a poster child for the problems of the health care law. The privately held company has lost $128 million in three states so far this year, following a $105 million loss in 2015, according to Bloomberg. It’s bowing out of two marketplaces, in Dallas and New Jersey, and restructuring its hospital and physician networks elsewhere.  In February it expects to begin selling insurance to small companies. Entering that market, which doesn’t depend on the Affordable Care Act, has been part of Oscar’s long-term plans from the start.  But since so much of Oscar Health’s business hinges on the health law, its fortunes will be shaped, in part, by the Trump administration’s decisions on the Affordable Care Act.  Oscar Health, Josh Kushner, Jared Kushner, and the Trump transition team did not respond to requests for comment.  Born into a New Jersey real estate dynasty, Josh Kushner was a freshman at Harvard when his father, Charles, went to prison after pleading guilty to tax evasion, witness tampering, and illegal campaign contributions. The father’s absence left Jared Kushner to run the family business.  Josh Kushner had a brief stint at Goldman Sachs after graduation. He then went to Harvard Business School, where he met the two men with whom he would start Oscar, named after Josh Kushner’s Eastern European great-grandfather.  Investors have poured more than $700 million into Oscar Health so far, and the company was recently valued at an eye-popping $2.7 billion.  But the individual market has proved a tough nut to crack.  “They’ve been met with the reality that it’s difficult to control health care costs, and it’s difficult to control people with chronic diseases, and just hanging out a shingle with a really cool logo is not enough to do it,” said Les Funtleyder, a health care investor at E Squared Asset Management, which has a holding in Oscar competitor UnitedHealth Group.  A rising star in venture capital, Josh Kushner has made 30-under-30, 35-under-35, and 40-under-40 lists of executives to track. He’s closely watched by the tabloids, thanks to his four-years-and-counting romance with Kloss. And he’s something of a regular on the high-brow conference speaking circuit.  In one appearance at an event nearly two years ago, sitting beside Theranos chief executive Elizabeth Holmes and former president Bill Clinton, Josh Kushner provocatively declared there are “a lot of people” in the health care industry who are “just evil.”  Glamour aside, he cultivates an image as a wonky, mild-mannered workaholic. In one interview he said he moved to an apartment two blocks from his office because he was too often sleeping at his desk overnight.  He’s also kept a low profile as Trump’s rise has spurred curiosity about the Kushner family. Through a spokesperson, Josh Kushner told Esquire magazine before the election that he has been a Democrat his entire life and would not be voting for Trump. The spokesperson also said that Josh Kushner loves his brother and did not want to say anything that would embarrass him.  Josh Kushner and his partners timed the 2013 launch of Oscar Health with the implementation of the health law, which created state exchanges where consumers can enroll in insurance plans. The company sought an edge by targeting millennials with playful ads and a Silicon Valley vibe.  Oscar Health has also built ties to Obama’s team. During its first year, the company reportedly turned to several campaign operatives from President Obama’s reelection campaign to aid open enrollment.  Last year the White House trumpeted an online video from Oscar highlighting the affordability of health insurance. “We are incredibly motivated by the support the White House has shown us today on this initiative,” the company said in the video.  Oscar said in a statement after the election that “we can’t speculate” on what the results mean for the Affordable Care Act, but “we hope and expect that the new administration will keep the spirit of consumer choice and competition alive in the marketplace.”  Experts on the health law said it’s unlikely Trump’s win will directly spell either doom or boon for Oscar Health.  Its future, like that of other insurers, depends on how the market for individual plans fares — and that depends on what Trump proposes for a replacement, said Katherine Hempstead, who specializes in health policy at the Robert Wood Johnson Foundation.  The Trump administration could boost Oscar, particularly if Republicans can manage to fix some of the problems with the health care law. But Oscar could take a hit if the GOP reduces the public subsidy for coverage. It could also be hurt if fewer people sign up for health plans — although new federal data show the pace of enrollment up considerably since Trump’s election.
Joshua Kushner is a rising star in the venture world whose health care company depends on the contentious law.