[3] He began his career at Merrill Lynch before joining InternetNews.com and the Silicon Valley news blog Valleywag.

[4][5] In 2015, Carlson published the biography Marissa Mayer and the Fight to Save Yahoo!.

[2][6] He won a Longform award for best business coverage for his reporting on AOL CEO Tim Armstrong's controversial investment in the local news initiative Patch.

[7] In 2022, Gawker reported that Carlson earned an annual salary of $600,000 as Insider editor-in-chief.

[8] Carlson was observed on June 13, 2023 taking pro-union posters with his face on them off lampposts in Windsor Terrace, Brooklyn during a labor strike at Insider by its journalists.