Jason Calacanis. Photo: Earl Mcgehee/Getty Images

At an Oakland event last Friday, a prominent Silicon Valley investor walked back some controversial comments about bias in tech — and unintentionally offered an inventory of the industry's persistent blind spots on diversity and inclusion.

Why it matters: Many Silicon Valley leaders believe they've created a meritocracy that's working just fine. Progressive critics and people in groups that feel they've been excluded see it as fundamentally broken. It's rare to see these two perspectives face off head to head, civilly, in a public forum.

The background: Jason Calacanis, an angel investor in media and tech whose early bet on Uber paid off big, spent an hour onstage at the Kapor Center, a downtown Oakland nonprofit that aims to "level the playing field in tech" (and that explained the reasoning behind Calacanis's invitation here).

The talk: Calacanis was pitching his Open Book Challenge, which is offering seven $100,000 grants to startups that "want to build a billion-user social network to replace Facebook — while protecting consumer privacy." His appearance certainly got that opportunity in front of the crowd, which contained a lot more entrepreneurs of color than your typical tech industry event.

The real talk: But most of the conversation between Calacanis and Phaedra Ellis-Lamkins, a serial entrepreneur who is the founder of Promise, focused on Calacanis's record of provocative comments on Twitter and elsewhere, for which he has faced years of criticism (including a "most offensive tweet of 2014" prize from Vice).

Evolution: Calacanis said that his belief in the tech industry's meritocracy has changed: "Does everybody have an equal shot in Silicon Valley? The answer is no." If a company has "performed" by achieving massive growth, investors won't care who the founders are, he added — but when they're betting on startups that have not already taken off, then biases can kick in.

  • Calacanis said he'd had faith in the tech industry's fairness because he'd seen himself as "an outsider's outsider" growing up working-class in Brooklyn. Later, he said, "I learned that my personal experience of 'I had it hard' is not contextually correct. Others had it harder."

Devolution: Through much of the event, Calacanis embodied the arrogant-tech-dude stereotype he seemed to be trying to transcend:

  • Egotism: ""I'm the greatest!," he announced — "the greatest angel investor currently investing...."
  • Arrogance: "Probably one of my greatest strengths is I don't care what anyone thinks of me."
  • Interrruption: When Calacanis tried to break into a question Ellis-Lamkins was laying out, she had to remind him to let her finish.
  • Deflection: Calacanis likened his situation to that of Joy Reid, the MSNBC host who's been criticized for intolerant decade-old blog posts. Ellis-Lamkins called him out for trying to change the subject from his own missteps to those of a black woman.

Lack of trust: Ellis-Lamkins told Calacanis that his Twitter record made her feel that, as an investor, he wouldn't have her back. "Some of the things you said or tweeted about race and women would make me feel not welcome. I'd think, 'he's not my people.' He can't see me, and when I have issues as a woman of color, he's going to think, 'It's me.' How will people here know that you're on their side?"

No deal: At the end, Calacanis thanked her for "the most interesting interview in my life." Previously in the conversation, he had asked her whether she would take an investment from him, and she'd said no. He asked one more time, but she shook her head.

Correction: This article originally reported incorrectly that Calacanis had said Ellis-Lamkins' company had previously turned down its investment.

Go deeper

Updated 25 mins ago - Politics & Policy

Coronavirus dashboard

Illustration: Sarah Grillo/Axios

  1. Global: Total confirmed cases as of 8:30 p.m. ET: 30,911,999 — Total deaths: 959,059— Total recoveries: 21,147,903Map.
  2. U.S.: Total confirmed cases as of 8:30p.m. ET: 6,796,384 — Total deaths: 199,474 — Total recoveries: 2,590,671 — Total tests: 95,108,559Map.
  3. Politics: Testing czar on Trump's CDC contradictions: "Everybody is right" Ex-FDA chief: Career scientists won't be "easily cowed" by political vaccine pressure.
  4. Education: What we overlooked in the switch to remote learning.
  5. Health: The dwindling chances of eliminating COVID-19 — 7 states set single-day coronavirus case records last week.
  6. World: England sets £10,000 fine for breaking self-isolation rules — The countries painting their pandemic recoveries green.

Arrest over letter to Trump containing poison ricin

President Trump returning to the White House from Minnesota on Sept. 18. Photo: Win McNamee/Getty Images

A suspect was arrested for allegedly "sending a suspicious letter" after law enforcement agents intercepted an envelope addressed to President Trump containing the poison ricin, the FBI confirmed in an emailed statement to Axios Sunday.

Details: The suspect, a woman, was arrested while trying to enter New York from Canada, law enforcement forces said.

Trump campaign goes all in on Pennsylvania

Trump poster in Scranton, Pennsylvania. Photo: Robert Nickelsberg/Getty Images

The president's campaign is placing more importance on Pennsylvania amid growing concern that his chances of clinching Wisconsin are slipping, Trump campaign sources tell Axios.

Driving the news: Pennsylvania, which has 20 electoral votes, twice Wisconsin's number, actually has been trending higher in recent public and internal polling, a welcome development for the campaign.