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As collaborators during their time at Chicago Technology Cooperative, Dave and Nick worked around the clock and through the weekend to implement custom design elements for the Drupal, the blog boasts custom content structures for columns and features, social media sharing tools and support for embedded third party multimedia content. Additionally, a robust permissions model for handling regular contributors and guest authors, integration with third party spam control tools, and a powerful moderation workflow were developed to give the appropriate level of control to the editors. Dave and Nick also migrated the project through a few different hosting providers due to their incredibly rapid growth; the project was mentioned on the front page of the Daily Kos and the Huffington Post in the same week, less than a month after launch.

In September of 2008, just ahead of the election, Midwest Business voted Progress Illinois the number one political blog in the state, ahead of the Daily Kos IL, ArchPundit, and Prairie State Blue.