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OutspokenKieran originally joined in the summer of 2011 on his previous account, trooper687. His current account was created on September 12, 2011 under the name FriendlyLOLpwnzr. He changed his name to OutspokenKieran on New Year's Day 2015. In 2012, OutspokenKieran received his Red Banded Top Hat for sharing a glitch with the Personal Build Server tools with the admin ReeseMcBlox. On February 29, 2015, OutspokenKieran achieved 10,000 posts. He has never been terminated from the site to this day.
OutspokenKieran discovered the ROBLOX Forum in 2012 and began to post in ROBLOX Talk. In 2013, the sub-forum All Things ROBLOX was created and he moved there on the day of its creation. For two years, he primarily posted in All Things ROBLOX and considered himself an "ATRer." He eventually stopped posting in the sub-forum entirely due to him being uncomfortable around newer posters. In December of 2014, OutspokenKieran grew fond of Off Topic and started posting there regularly. This is where he found a community of other users who he could relate to.