After his lead investor helped get Donald Trump elected, Ryan Petersen was beset by misgivings -- and he wasn't shy about saying so.
On stage at TechCrunch Shanghai 2016, Petersen, CEO of the shipping logistics startup Flexport, said that he he might not have let Peter Thiel lead the company's $20 million Series A round if he had known that Thiel was going to be a vocal Trump supporter. "Well, it depends on how desperate we were," Petersen said when asked about that hypothetical scenario.
"I don't think that supporting Donald Trump is an acceptable position, honestly," he added. "For our business, it would be disastrous."
In particular, Trump's protectionist rhetoric clashes with Flexport's reliance on global trade: Goods flowing from East Asia to North America constitute roughly 85 percent of Flexport's volume, Petersen tells Inc. He points out that protectionist policies like imposing high tariffs on Chinese goods could hurt the importers who use Flexport.
Petersen knew that talking out of school about an investor -- much less one as well-connected as Thiel -- carried risk for him and his company. But, true to his contrarian ethos, the billionaire Founders Fund principal didn't react in the predictable way.
"My relationship with Peter actually got much better after that," Petersen says. Rather than take umbrage, Thiel appreciated Petersen's directness: "Everyone else started calling him names, and at least I was arguing about the actual ideas and debating him on the central point of an argument rather than making ad hominem attacks," Petersen says, recalling their conversation. (Thiel did not respond to a request for comment.)
Thiel's measured handling of a portfolio founder's airing of political grievances puts him in stark contrast to Jared Kushner, another Trump adviser with ties to Silicon Valley. Kushner is Trump's son-in-law and has become a trusted aide. His background is in real estate and media, but Kushner has also invested in multiple tech startups. One of those was Good Uncle, which helps users find "crave-worthy food."
According to Business Insider, Kushner invested "no more than a few hundred thousand dollars," which is not a huge amount in the world of venture capital. Good Uncle's liberal founder, Wiley Cerilli, decided to give the money back because he was so troubled by Kushner's participation in Trump's campaign and administration. Not only could the association hurt Good Uncle's brand, he felt, but it was an ethical strain.
Cerilli reportedly told Kushner, "Your involvement is something that is not incredibly clear to me, but what is your unwillingness to speak out against it? This is not a conversation about what [Donald Trump] or you believe or what he and you do and feel behind closed doors. This is about what he says and does publicly and what is not said and done publicly by you."
Kushner reacted angrily, calling Cerilli cowardly and childish. Seemingly blurring the lines between business and personal relationships, Kushner said that his new involvement in politics had shown him which of his friends would stick around and which would be "exfoliated." He told Cerilli, who took notes during their conversation, "You clearly don't have the depth to take on a big challenge [like scaling a startup] when something like this bothers you, and so clearly your team doesn't either."
Kushner's outburst did not earn him admiration in Silicon Valley. Well-known seed investor Hunter Walk remarked on Twitter, "So much respect for @wileycerilli returning investment from @jaredkushner. And so little class from Kushner in response."
The contrast between Thiel's and Kushner's responses may account for the former's continuing social currency in Silicon Valley. Thiel is persona non grata in certain liberal quarters, but high-profile friends like Y Combinator president Sam Altman have stuck by him. Thiel also does not seem to be the type of person who is overly bothered by his public image -- he's a radical futurist and has a history of heterodox thinking.
In a January interview, Thiel told Maureen Dowd, "One of my good friends said, 'Peter, do you realize how crazy this is, how everybody thinks this is crazy?' I was like: 'Well, why am I wrong? What's substantively wrong with this?' And it all got referred back to 'Everybody thinks Trump's really crazy.' So it's like there's a shortcut, which is: 'I don't need to explain it. It's good enough that everybody thinks something. If everybody thinks this is crazy, I don't even have to explain to you why it's crazy. You should just change your mind.'"