Last year, after pressure from activist investors, Jeff Lawson stepped down from his perch as CEO from Twilio, the cloud communications company he co-founded. But he didn’t spend any time twiddling his thumbs — that same spring, he bought the satirical news organization The Onion, and by the end of the year, they’d tried to buy Alex Jones’ Infowars at a bankruptcy auction. 

Jeff also stayed busy on the political front, continuing his work on DemocracyFirst, a political action committee he co-founded, in 2022, to support candidates committed to democracy. 

So there was plenty to chew on when Kara interviewed Jeff last week at Democracy’s Information Dilemma, a symposium hosted by the University of Michigan’s Gerald R. Ford School of Public Policy.

They discuss the tech founder mindset; how Jeff is remaking The Onion; why political satire is more necessary than ever; why DEI — which Jeff championed as a CEO — can sometimes do more harm than good; and how to fight for democracy during Trump 2.0.

Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher.

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