The Other Kushner’s Next Move

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For most of its 12 years, Thrive Capital has been known as a fast-growing venture capital firm that struck some savvy deals, most famously an investment in Instagram that doubled in value within days.

But for the past four years or so, the firm and its 35-year-old founder, Joshua Kushner, have become just as well known for something unrelated to the fortunes of the fund: Mr. Kushner’s older brother, Jared, a top adviser and son-in-law to President Donald J. Trump.

And though having one’s brother in the White House may seem like a benefit, for Thrive, the questions mostly arose about whether the Trump connection would hamper its ability to invest in start-ups, especially those run by liberally minded entrepreneurs.

That filial bond had put Mr. Kushner in an awkward position, subject to calls to push his brother and sister-in-law, Ivanka Trump, to change administration policies. But Mr. Kushner steadfastly refused to do so, at least publicly.

Now that Mr. Trump is out of office, that complication may be reduced. But don’t expect Mr. Kushner to say much about the challenges of the Trump years, or whether there are any lingering effects on Thrive, good or bad.

He declined to comment for this article.

The Kushner brothers are close. Associates say the two drew even tighter after their father, the real estate developer Charles Kushner, was imprisoned for two years after pleading guilty to illegal campaign donations and witness tampering in 2005. The brothers have also done business together, co-investing in ventures like Cadre, a real-estate technology start-up. (The younger Mr. Kushner has never formally worked for the family’s real estate business.)

Jared Kushner divested his holdings in Thrive before joining the White House, and no member of the Trump family has invested in the firm, according to a person briefed on the matter. After leaving the White House, Jared has not invested in Thrive.

In public, Joshua Kushner has said little about his feelings regarding the Trump administration, unless one counts appearing at protests like the Women’s March in 2017 and the March for Our Lives the next year. He has also mostly donated to Democrats over the years, including Beto O’Rourke and Cory Booker.

His wife, the model Karlie Kloss, has been more openly critical of Mr. Trump, from elliptically referring to disagreements with her in-laws on talk shows to holding up a 2020 ballot while wearing a Biden-Harris face mask. (When a Twitter user pressed Ms. Kloss to chide her in-laws over the Jan. 6 Capitol riot and Mr. Trump’s baseless election conspiracy theories, the model responded, “I tried.”)

In private, Mr. Kushner has made his feelings clearer. Stewart Butterfield, the chief executive of Slack, recalled that shortly after the 2016 election, Mr. Kushner, whose fund invested in the workplace messaging firm earlier that year, called him.

“I don’t remember what he said exactly,” Mr. Butterfield said, “but it was a tactful way of saying, ‘These are not my positions.’”

Mr. Kushner espouses socially liberal ideals, associates say, with interests in causes like racial justice. “He understands that we have a real challenge of racism,” said Darren Walker, the president of the Ford Foundation, which has invested in several of Thrive’s funds. He praised Mr. Kushner’s work with Black entrepreneurs like Ryan Williams, the chief executive of Cadre.

There are also business-related disagreements. Mr. Trump’s efforts to unwind the Affordable Care Act threatened the existence of Oscar, the health insurance provider that Mr. Kushner co-founded, which draws the majority of its revenue from plans built around Obamacare. At a private event for Oscar in 2018, Mr. Kushner concluded a recap of the year’s challenges by quipping, “We survived Donald Trump.” He then added, “Don’t tweet that.”

But those who know Mr. Kushner say that he tends not to talk much about politics or his brother, particularly in business settings.

“Unfortunately, he has had to defend his brother — not with me, I don’t talk about that with him — but that has occasionally put him on the defensive,” Mr. Walker said.

Mamoon Hamid, a partner at the rival venture capital firm Kleiner Perkins, who says that he is a friend, had pushed Mr. Kushner to speak out against Jared and the administration on issues like the ban on travelers from predominantly Muslim countries, to no avail.

“Blood is thicker than water,” Mr. Hamid said, adding that he eventually stopped trying to persuade Mr. Kushner to act. “At some point, I don’t think my conversation was doing anything, and my friendship was more important.”

The brothers remain close, even physically: Mr. Kushner bought a mansion in Miami last August; several months and one presidential election later, Jared and his wife bought a multimillion-dollar plot that is a short drive away.

Since founding Thrive in New York in 2009, at the age of 25, Mr. Kushner and his team built a reputation as low-key, nerdy investors who prefer sifting through balance sheets and strategy documents than pontificating on social media.

Mr. Kushner has also benefited from a high-powered network: Early backers included Princeton University and Peter Thiel, and in 2013, Thrive hired Jon Winkelried, a former president of Goldman Sachs who is now co-chief executive of the investment giant TPG, as a senior adviser. Employees include former staff members in both the George W. Bush and Barack Obama administrations.

Thrive’s investments include early-stage start-ups and so-called growth rounds in older, more established companies. Unusually, it also incubates companies, including Cadre and Oscar (which is named after Mr. Kushner’s grandfather).

Thrive controls around $9 billion in assets, having raised $2 billion for two new funds last month. The firm declined to comment on its financial performance. “They have been consistently a high performer in our portfolio,” is all that Mr. Walker of the Ford Foundation would reveal.

Thrive first focused on consumer-facing businesses like the eyeglasses retailer Warby Parker and the e-commerce platform Jet. Among its first blockbuster hits was Instagram, where it invested in 2012 at a $500 million valuation as part of a financing round, only to see Facebook agree to buy the social network for $1 billion 72 hours later.

Despite all the attention that later went on Mr. Kushner’s high-profile brother, Thrive didn’t appear to alter its approach in the Trump era. One big win was the sale of the online code repository Github to Microsoft in 2018. Thrive had invested $150 million in Github for a 9 percent stake; the company was sold for $7.5 billion.

In the waning days of the Trump administration, Thrive’s bets included becoming one of the first outside investors in Vimeo, the video platform owned by IAC, when it led a fund-raising round for the company at a $2.75 billion valuation in November. In January, Vimeo raised another round, at a $6 billion valuation.

Thrive was “a bit of an underdog” when Vimeo was vetting investors, said Anjali Sud, the company’s chief executive. But she was won over by what she called “this insanely dense, nuanced analysis of Vimeo and our market.”

Since then, she said, she texts or calls someone from Thrive most days for advice or guidance as it prepares to be spun off from IAC this year.

Other portfolio companies that have either sold themselves or gone public in recent months include Slack, which Salesforce agreed to buy for $27.7 billion; Affirm, the e-commerce lender whose shares doubled on their debut; and Opendoor, an online home-selling marketplace that jumped in value when it merged with a blank-check company.

Although the political clouds hanging over the firm may have lifted, Mr. Kushner and his businesses aren’t necessarily in the clear.

Take Oscar, in which Thrive has a stake worth more than $1 billion. Despite its heady initial offering last week, raising $1.4 billion at an $8 billion valuation, the insurer’s shares fell in their first day of trading and only recently retraced their ground. The company has warned that it may not turn a profit for some time. Skeptics say its core insurance business is too small and limited to justify its valuation.

“Oscar’s philosophy doesn’t seem very different than the others,” said Les Funtleyder, a portfolio manager at E Squared Asset Management who focuses on health care investments. “After looking at their financials, their execution hasn’t been spectacular.”

Mr. Kushner also recently lost a longtime business partner at Thrive, Miles Grimshaw, who was involved in start-ups like the software company Airtable. In December, Mr. Grimshaw joined the Silicon Valley giant Benchmark, though the split wasn’t acrimonious.

And then there is the possibility that politics could intrude once again: Mr. Trump has hinted he may run for president in 2024, and Jared could again serve as one of his top advisers. That would renew the tests of loyalty and related complications that the younger Mr. Kushner may have thought were behind him.

What do you think? Will Joshua Kushner’s family ties always loom over his ventures? Let us know:

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