The Other Brother

At A Very Young Age, Josh Kushner Has Built One Of America’s Ascendant Venture Firms And A $2.7 Billion Business Off Obamacare. Now His Brother, Jared, Sits At The Center Of A Trump White House That’s Endangering The Whole Operation.

- Steven Bertoni

As the world’s attention on November 8 turned to New York City, where both candidates awaited the results of the U.S. presidential election, one of Manhattan’s most connected people, Thrive Capital founder Joshua Kushner, boarded a flight to San Francisco.

In a few hours, his brother and best friend, Jared Kushner, would experience arguably the greatest political upset in American history at the side of his father-in-law, Donald Trump. Josh Kushner, who didn’t vote for Trump, would make due with seatback television on Virgin America Flight 29, en route to a board meeting for the messaging startup Slack.

Josh Kushner’s expectation: By the time he touched down, the Trump political experiment would be retired as a historical ego trip. Pre-Trump, Kushner had pretty much everything an ambitious 31-year-old could possibly hope for: a $1.5 billion venture capital shop that shot to prominence with an early bet on Instagram, a slew of high-profile startups that he was directly incubating and a life that remained low-profile even as he dated supermodel Karlie Kloss. The Trump Train had derailed much of that. Press and paparazzi gobbled up everything Kushner, family demons included, while Josh found himself linked, at least in perception, to proposals most of the tech community abhors.

As Kushner traversed the country in coach, however, glued to a small TV screen and reliant on sketchy airplane Wi-Fi, the professional relief that he expected upon touchdown disappeared, in lockstep with Hillary Clinton’s electoral hopes in Ohio, North Carolina, Florida and then Pennsylvania and Wisconsin.

“I was surprised,” Kushner says. “But not as surprised as the other passengers sitting around me.”