Sinker received media attention in 2011 after revealing himself as the author of @MayorEmanuel, a popular Weird Twitter account which satirized politician Rahm Emanuel.

[7] a parody account that Atlantic Magazine said, "pushed the boundaries of the medium, making Twitter feel less like a humble platform for updating your status and more like a place where literature could happen.

was originally conceived as an eight-week project in which Johnson and Sinker would talk with political experts about how they were surviving news coverage of the 2016 Presidential Election.

The podcast has since continued past the results of the election, switching to a biweekly, then weekly, and then, for a time, daily format in which the hosts attempt to humorously discuss the news of the day, and more personally, share how they are coping as citizens both in the current political era as well as the COVID-19 pandemic.

Since 2018, he has been an independent author, consultant, and entrepreneur, writing for Esquire Magazine,[10] and creating products like the Pee Tape and Robert Mueller III Prayer Candles.