It was created by Ken Doctor, a media analyst who had studied the decline of local newspapers in the United States.
[1] Lookout won a Pulitzer Prize for Breaking News Reporting in 2024 for its coverage of the 2022–2023 California floods.
Its three top editors and chief revenue officer left to work in other cities, and in February 2023, only two original staff members remained from the organization's October 2020 start.
[1] Ken Doctor, the newspaper's founder, frequently writes about the operations of Lookout Santa Cruz in his column for Nieman Journalism Lab.
[1] Lookout Santa Cruz won the 2024 Pulitzer Prize for Breaking News Reporting for its community-focused coverage of the 2022–2023 California floods that destroyed more than 1,000 homes and businesses.