The Site of Big Shoulders began in the summer of 1995 as an idea for an online publication which focused specifically on Chicago. A group of early 1990s Northwestern University graduates started getting together every week to hang out, geek out and work on pulling together the first edition of the online publication.

Brian Nemtusak, Justin Kerr, Mike Browarski  and Jake Eldridge work on The Site of Big  Shoulders circa 1996.Brian Nemtusak, Justin Kerr, Mike Browarski and Jake Eldridge work on The Site of Big Shoulders circa 1996.

Early participants in these sessions included Chicagoans Chris Brandely, Mike Browarski, Yvette Marie Dostatni, Jake Eldridge, Justin Kerr, Brian Nemtusak and a rotating cast of friends and acquaintances. Thursday nights became the default time for staff meetings, which were as much about learning new publishing technologies and having fun as they were about developing the publication.

The staff prepared five features comprising the content of the first edition of The Site of Big Shoulders, including poetry, artwork, a guide to Chicago-area street gangs, the first installment of "The Secret Lives of the Chief" story and a photo essay about Whiting, Indiana. Each Web page was laboriously hand-coded using text editors, and the staff created a great deal of accompanying art and photo illustration for each feature. Dave Homan, proprietor of the online magazine Chicago Psyberview, donated space on his Web server, and in the summer of 1996, the first edition of The Site of Big Shoulders went live at the Web address http://www.chitown.com/bigshoulders/ .

Following first publication in 1996, the staff continued to work on The Site of Big Shoulders, adding new content and recruiting new contributors and staff members. In 1998, the magazine took another step forward by getting its own Web hosting environment and Internet domain name: sobs.org. The staff pulled together a new "city-on-its-side" design concept and relaunched version 2.0 with a new look and more content.

Interest in The Site of Big Shoulders continued to grow – both through increased submissions and burgeoning Web site traffic – and around 2000, it became clear that the informal, kitchen-table nature of The Site of Big Shoulders needed to change. As put by Chief Operations Officer Jake Eldridge: "We need to either grow it, or kill it." The Site of Big Shoulders staff decided on the former and began to formalize operations and pursue official not-for-profit status, as the magazine had always been non-commercial in nature.

One first step toward not-for-profit incorporation was applying for and receiving a Community Arts Assistance Program (CAAP) grant from the City of Chicago, which provided the initial funding needed for filing state and federal 501(c)(3) not-for-profit incorporation documents. The Site of Big Shoulders received its probationary 501(c)(3) status in 2002 and its final 501(c)(3) status in 2007. Two succeeding CAAP grants provided funding for promotional materials and development help.

The Site of Big Shoulders also underwent another design and technology overhaul during this time, retaining the city-on-its-side design, but refining it and re-coding all of the index pages to better support contemporary Web browser technologies. Around this time The Site of Big Shoulders began employing Web applications for both publishing purposes and to support production activities.

Starting in 2002, The Site of Big Shoulders began to participate in local arts events, including the Pilsen Artists Open House and Around the Coyote art festival. For these events, The Site of Big Shoulders would sponsor the exhibition of artists and photographers, and concurrently publish online articles showcasing the artists' work. These events also often included live music, particularly for the evening receptions.

Although The Site of Big Shoulders existed as a formal not-for-profit entity, it had always lacked an actual office: Meetings were typically held at staff members' homes, and a virtual office environment enabled remote work. That changed in 2007 when Salvage One, a Chicago-based architectural salvage and furniture store, offered The Site of Big Shoulders a space in its warehouse to use as an office. The Site of Big Shoulders used the donated space between August 2007 and May 2008, and then moved to its current office at 1543 North Milwaukee in the Wicker Park neighborhood of Chicago.

During this era, The Site of Big Shoulders also invested heavily in deploying Web site technology to assist managing the content of the Web site.  The Joomla content management system (or "CMS") provided a platform for publishing site content, and new features were produced and presented within Joomla (while links to static vintage features were retained and integrated into the system).

The latest iteration of this platform is SOBS 5.0, deployed in February 2012.  This includes an upgrade to the latest version of the Joomla content management system and related software, full migration of all vintage content into the CMS, deployment of a new design and layout for the index pages of the Web site, and an overhaul of the site's Joomla template frameworks to support fast and easy deployment of content into custom designs.

Since 2010, The Site of Big Shoulders has been producing Art+Poetry Chicago, an annual program that brings together the poetry and art of the Chicago area.  This includes a poetry contest, an art contest based on winning poetry submissions, and a poetry reading and gala reception that brings the art and poetry together.