Jason Calacanis is a tech entrepreneur and investor who has repeatedly made sexist and/or racist statements without retracting or apologizing for them.
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
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. E.g., "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."
Denial of racism
In 2013 Calacanis denied that racism had any effect on success in tech, claiming "There isn't a race wall in tech" and "I can tell you the tech industry & tech media space are both largely post-race. Pure meritocracy... Page views rule." When Asian-American blogger Anil Dash pointed out that Calacanis' white and male privilege influenced his success, Calacanis called Dash racist. 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."
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%.
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.
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.