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July 29, 2025 24 mins

This conversation hit different. JR Butler went from Division I hockey at Holy Cross to building a company that got acquired by IBM for $2 billion. But the path wasn't straight. And it definitely wasn't easy. JR's story starts in a bar after a men's league hockey game. He was planning to go to law school. Study for the LSAT. Take the traditional route. Then he met a guy who owned a VAR who told him technology was the future. Guaranteed him he could make a quarter million in three years. JR said screw it. Decided to try tech sales instead of studying for the LSAT. By his third day he knew this was what he wanted to do for the rest of his life. But here's where it gets real. JR grew up as the oldest of three boys. All three played Division I hockey. One of his brothers was an Olympic athlete who played in the NHL. When JR asked his dad when he knew his brother Bobby would make the NHL his dad said he knew when Bobby was seven. That creates a dynamic. The naturally gifted kid gets the attention. The oldest learns to fend for himself. JR had to find his own lane. He wasn't the most talented hockey player. But he was accountable. Self-reliant. He learned to bet on himself. That translated perfectly to sales where you eat what you kill and it's 100% on you. Extreme ownership became his foundation. This episode is about finding your lane when you're not the most naturally gifted. About learning from failure. About transferring skills from one arena to another. And about building something meaningful from your own struggle.


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Connect with Rick: https://linktr.ee/mrrickjordan

Connect with JR: https://www.shiftgroup.io/ 


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About JR:  JR Butler is the Founder and CEO of Shift Group, a sales recruiting and training firm that specializes in helping college, professional, and Olympic athletes transition into the world of Technology Sales. Prior to starting Shift Group, JR was Chief Revenue Officer at Pillir, a fast growth low code software company out of Arizona. Prior to becoming a CRO, JR built and ran multiple sales teams at Turbonomic, helping the company go from a Series A start up to a $2B acquisition by IBM. JR grew up playing multiple sports but went on to play Division 1 hockey at Holy Cross in central Massachusetts where he grew up. He was a sophomore on the 2006 team that beat Minnesota in the biggest upset in College hockey history. JR comes from a hockey family, with two brothers that played at the college level, with one going on to play in the NHL and the Olympics and a father whose in the Massachusetts Hockey coaches hall of fame.

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