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During Punk's time in IWA: Mid-South, he had high profile feuds with Colt Cabana and Chris Hero while also rising to the top of the roster winning the IWA Mid-South Light Heavyweight Championship twice and the IWA Mid-South Heavyweight Championship on five separate occasions, beating stars like A. Styles, Cabana and even Eddie Guerrero for that Championship.

Punk's feud with Hero included a 55-minute TLC match,a 93-minute two out of three falls match, and several 60-minute time limit draws.

As part of the training, he wrestled at Steel Domain Wrestling in St. It was in the Steel Domain that he met Scott Colton, who soon adopted the stage name Colt Cabana.

Punk and Cabana became best friends and spent most of their early career together working in the same independent circuit promotions, as opponents or allies.

Shortly before a TNA show on February 25, 2004, Punk had a physical scuffle with Teddy Hart outside of a restaurant that was broken up by Sabu.

The scuffle reportedly stemmed from an ROH show in which Hart performed three unplanned spots putting several other wrestlers in danger of injury.

At the same time, Punk joined the wrestling promotion NWA Total Nonstop Action (TNA), in which he was paired with Julio Dinero as members of Raven's TNA alliance The Gathering.

Punk started climbing the ranks of ROH, including coming in second at the Second Anniversary Show during the tournament to crown the first ROH Pure Champion, losing to A. Styles in the finals and winning the ROH Tag Team Championship twice with Colt Cabana as the Second City Saints.

Unlike his friends, Punk genuinely wanted to be a wrestler and saw it as more than simple fun.

When the promotion started taking off, doing spot shows out of a warehouse in Mokena, Illinois, Punk found out that his brother Mike had embezzled thousands of dollars from the small company, causing them to become estranged. He soon left the federation and enrolled as a student at the "Steel Dominion" wrestling school in Chicago, where he was trained by Ace Steel, Danny Dominion and Kevin Quinn to become a professional wrestler.

In the independents, Punk, along with fellow Steel Domain graduates Colt Cabana, Chuckee Smooth, Adam Pearce and manager Dave Prazak, formed an alliance named the Gold Bond Mafia.

Punk's home promotion for his early career is usually considered to be Independent Wrestling Association: Mid-South (IWA: Mid-South).

Punk's matches with Cabana led him to being hired by the Ring of Honor promotion.

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