Before Tim Montana signed with Bbr Music Group/Music Knox Records to release his major label debut, Long Shots, the longhaired, bearded mountain man from Butte, Montana, would watch quietly as the career path he carved out for himself was repeatedly questioned by Nashville executives and managers.

While Montana was building an audience of music fans as a hard-touring country-rocker, playing shows with Zz Top, Lynyrd Skynyrd, and Hank Williams Jr., he was also cultivating an online following as an unconventional social-media influencer. He may not have had the massive...