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Jason Calacanis is a tech entrepreneur and investor who has repeatedly made sexist and/or racist statements without retracting or apologizing for them. He is the winner of the "Most Offensive Tweet" award for 2014 from Vice News, who wrote "With one tweet, Uber investor Jason Calacanis epitomized the sort of white privilege undergirding Silicon Valley culture." The Atlantic said, "As a counter-argument to a much discussed post on why white males dominate the tech blogging world, white male tech blogger Jason Calacanis took to Twitter today in using his own successful experience — and pretty much only that — to prove that such racism doesn't exist."

Background

Calacanis first rose to prominence with the sale of the blog network he co-founded, Weblogs, Inc., in 2005 to AOL for a reported $25 million. He was "Entrepreneur in Action" at major VC fund Sequoia Ventures. He is an angel investor in over 100 tech startups, including Uber and Tumblr. He founded and runs the LAUNCH conference, VC fund, and media company.

Racism, sexism, and Islamophobia

Calling descriptions of white privilege racist

In December 2016, Calacanis called a comment by Kortney Ziegler racist because it described white privilege.

In August 2016, Calacanis recommended owning a gun as the way to stop stalkers. When another Max Lapides asked him to consider that his advice might work better for rich white men, Calacanis accused him of being racist.

In July 2014, when Asian-American blogger Anil Dash pointed out that Calacanis' white and male privilege influenced his success, Calacanis called Dash racist. This tweet won the 2014 Vice News award for "Most Offensive Tweet."

Support of Milo Yiannoupolos

In January 2016, Calacanis tweeted in support of well-known racist, misogynist, and transphobic activist Milo Yiannoupolos, making jokes commiserating with him over Twitter's policies and mocking another person for objecting to being harassed by Yiannoupolos's followers.

Sexist take on sexism in VC

In 2015, Calacanis wrote a blog post entitled "Mansplaining the Ellen Pao trial & fixing the gender issue in venture capital" about Ellen Pao's gender discrimination lawsuit against VC firm KPCB. In the post, he lists questions that he says "folks in the know I’ve talked to" are asking about Ellen Pao and the lawsuit which are all framed in a sexist manner, while being intentionally vague about whether he agrees with them or not (e.g. "Is this case going to cause VCs to hire fewer women because KPCB worked hard to include more women and it has blown up in their face?"). He ends the post by recommending his solution to sexism in VC: more rich women should start VC funds.

Denial of personal racism due to relatives of color

In December 2014, Calacanis responded to winning the 2014 Vice News award for "Most Offensive Tweet" by citing his wife and child, both people of color, as proof he was not racist. "I'm not a racist or clueless. I'm actually in a mixed race marriage, with a mixed race child & from Brooklyn. :)"

Denial of personal sexism due to female relatives

In August 2014, Calacanis denied accusations of sexism by citing the existence of his mother, wife, and daughter.

Proposal to violate privacy of intimate partner violence victim

In April 2014 in response to the Gurbaksh Chahal domestic violence conviction, Calacanis promised to donate $10,000 to a non-profit fighting domestic violence if someone gave him the video footage of the incident, and promised to play the audio from the recording on his podcast. He did not get permission from the victim of Chahal's violence and abuse to broadcast her half-hour long ordeal. In the replies to his offer, he dismissed multiple people pointing out that he was revictimizing the victim without her consent.

All-male speaker lineup

In January 2014, Calacanis' LAUNCH Festival featured a speaker line-up of 16 men and zero women. Calacanis responded to criticism of this by tweeting a photo of women at an event for female founders at the conference and implying that he'd had four women speakers lined up but they had all canceled. The odds that the 16 speakers would all be men by chance is 0.03%.

Denial of racism in tech

In 2013 Calacanis denied that racism had any effect on success in tech. His statements include:

Calacanis made his statements in response to an article by African-American writer Jamelle Bouie pointing out that blogging was dominated by white men. Several publications reported on and dissected Calacanis' statements, including Gawker, Buzzfeed, and The Atlantic. Calacanis expanded his views in a blog post he later deleted, which began with a quote from Kanye West and the statement "I’m a white guy so I’m not allowed to talk about race."

Racism and Islamophobia

In 2010 Calacanis made several statements about people in the Middle East embracing racist and Islamophobic stereotypes in a guest post for TechCrunch. "For over a year, I haven’t visited a gas station and have been able to give the finger to the bastards in the Middle East who believe that women and gays are about as valuable as dogs, and that the freedoms we enjoy in the United States are the root causes of all evil." Talking about Afghanistan, he said, "We have to stop wasting our money building schools and bridges for backwards societies that don’t appreciate them and start spending that money on energy independence."

Bragging about sexual exploits

In 2009, Calacanis addressed a crowd of more than 700 people at a New York City tech meetup and said, "My wife is here [...] If there are any women I used to date in the audience, don’t come up to me afterward."

In 2000, Calacanis bragged to the New York Observer about how many women pursued him sexually (page 216). "I can’t tell you how many propositions I get, it’s absolutely insane... My life is surreal. I’m not used to women liking me... it’s depressing to think they like me for my Rolodex, or for what I can do for their dot com."

Propositioning a woman founder

In 2008, Calacanis invited a woman pitching a company to him to "stay in his summer house" and asked if she had a boyfriend (page 216).

Further reading