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Photo illustration of Peter Thiel

Peter Thiel may be the most successful venture capitalist of his era, with a resume that spans from Facebook to SpaceX to Airbnb. But no venture capitalist bats 1000, and Thiel's biggest whiff was of much greater consequence than pushing a mediocre app into the market.

Flashback: Just days before Donald Trump's 2016 election, Thiel criticized the media for taking Trump literally rather than seriously, contrasted to Trump voters who took him seriously but not literally.

  • This was not an original framing, as Thiel lifted it from a pre-election column by Salena Zito in The Atlantic.
  • But Thiel's forum (the National Press Club) and his profile (iconoclastic Silicon Valley billionaire) amplified his message far beyond The Atlantic's readership, and helped establish and then cement a viewpoint through which even Trump's most egregious statements were taken at other than face value.

What's come into stark relief, however, is that Trump says what he means and means what he says.

  • We heard it in his call with Georgia's secretary of state, in which Trump made clear that his conspiracy theory was not just for public consumption.
  • We saw it in his reticence to condemn the Capitol insurrectionists, after weeks of telling them to fight.

Thiel, who didn't respond to interview requests, himself gave up on advocating for Trump earlier this year, in the midst of White House mismanagement of the pandemic, not speaking again at the Republican National Convention nor donating in 2020 to Trump's re-election campaign.

  • His fundamental framing of Trump's presidency, however, had already taken root. And far too few Americans, including media members who Thiel had initially critiqued, recognized the flaws in his thesis until it was too late.

Go deeper

Off the Rails

Episode 6: Last stand in Georgia

Photo illustration: Aïda Amer/Axios. Photo: Drew Angerer, Raymond Boyd/Getty Images

Beginning on election night 2020 and continuing through his final days in office, Donald Trump unraveled and dragged America with him, to the point that his followers sacked the U.S. Capitol with two weeks left in his term. Axios takes you inside the collapse of a president with a special series.

Episode 6: Georgia had not backed a Democratic presidential candidate since 1992 and Donald Trump's defeat in this Deep South stronghold, and his reaction to that loss, would help cost Republicans the U.S. Senate as well. Georgia was Trump's last stand.

On Air Force One, President Trump was in a mood. He had been clear he did not want to return to Georgia, and yet somehow he'd been conscripted into another rally on the night of Jan. 4.

Off the Rails

Episode 3: Descent into madness ... Trump: "Sometimes you need a little crazy"

Photo illustration: Sarah Grillo/Axios. Photos: Tom Williams/CQ-Roll Call, Chip Somodevilla/Getty Images

Beginning on election night 2020 and continuing through his final days in office, Donald Trump unraveled and dragged America with him, to the point that his followers sacked the U.S. Capitol with two weeks left in his term. This Axios series takes you inside the collapse of a president.

Episode 3: The conspiracy goes too far. Trump's outside lawyers plot to seize voting machines and spin theories about communists, spies and computer software.

President Trump was sitting in the Oval Office one day in late November when a call came in from lawyer Sidney Powell. "Ugh, Sidney," he told the staff in the room before he picked up. "She's getting a little crazy, isn't she? She's really gotta tone it down. No one believes this stuff. It's just too much."

Off the Rails

Episode 2: Barbarians at the Oval

Photo illustration: Sarah Grillo/Axios. Photo: Jim Watson/AFP/Getty Images

Beginning on election night 2020 and continuing through his final days in office, Donald Trump unraveled and dragged America with him, to the point that his followers sacked the U.S. Capitol with two weeks left in his term. This Axios series takes you inside the collapse of a president.

Episode 2: Trump stops buying what his professional staff are telling him, and increasingly turns to radical voices telling him what he wants to hear. Read episode 1.

President Trump plunked down in an armchair in the White House residence, still dressed from his golf game — navy fleece, black pants, white MAGA cap. It was Saturday, Nov. 7. The networks had just called the election for Joe Biden.