[9] The company announced a major expansion in October 2017 with the launch of Crooked.com, a text journalism site helmed by Editor-In-Chief Brian Beutler, a former New Republic senior editor.

The expansion introduced the "Crooked Contributors" network, a group of progressive journalists, activists, organizers, policy experts, campaign veterans, and comedians who would be featured in podcasts, videos, and articles produced by the company.

[17] Hosted by Vietor and former Deputy National Security Advisor Ben Rhodes, Pod Save the World discusses foreign policy and international relations.

Lovett or Leave It is a recording of a weekly live show and features the eponymous host dissecting the news with a panel of guests.

The tour featured live versions of Pod Save America and Lovett or Leave it, and appearances from DeRay Mckesson, Ana Marie Cox, and other guests.

[6][48] The Los Angeles Times reported that according to Crooked Media, it raised $2.7 million and directed 22,000 volunteers to fill shifts in competitive races during the 2018 midterms.

In May 2019, the Crooked Media campaign "Vote Save America" launched the F*ck Gerry(mandering) Fund with Data for Progress to direct listeners' donations to 14 of the closest races in Virginia.

[50][51] Ahead of the 2020 election cycle, under the umbrella of Vote Save America, they raised $32 million in the third quarter of 2020, which was directed to Democratic candidates.

[53][54] As of January 2024, Vote Save America planned to focus on fundraising for and directing volunteers to competitive down-ballot races for congress as well as ballot initiatives because of the lack of interest in the Biden candidacy.

[12] Reviewing the first episodes of the company's flagship podcast, The Guardian noted: "Pod Save America's commentators are sparky and funny—and they have a habit of talking a whole lot of sense.