In this episode, Tim sits down with Annie Ortmeier, co-president of Triple Tigers Records, for a deep dive into the evolution of the music business and what it takes to stay ahead of it.Annie shares her unconventional path into the industry, from early roles in e-commerce and digital marketing to helping shape the streaming era at a major label. Now at Triple Tigers, she’s helping lead one of the most successful label models in Nashville by bridging the gap between radio and digital strategy.The conversation covers everything from adapting to new technology, navigating industry resistance to change, and how data has transformed decision-making—while still respecting the power of radio. Annie also breaks down what it looks like to build an artist’s brand the right way, highlighted by the breakout success of Russell Dickerson and the importance of aligning identity with music.