Money talks. But what is it really saying? In the mainstream music market, money has a tumultuous history, exploiting even the world’s most powerful musicians. From Prince painting the word “Slave” to his face in rebellion against his record label to Taylor Swift re-recording her old songs to reclaim her master rights, money has long been perceived as a corrosive force. But this all changed when streaming emerged. With the average payout per stream yielding to a mere fraction of a cent, record labels and listeners have been redefining how music is priced and valued. In this digital re-arrangement, my senior thesis asked how music tastemakers and consumers managed these new forms of monetizing music. Specifically, I adopt Viviana Zelizer’s connected-lives framework to identify how these new forms of monetizing music are instead regularly shaped by symbolic meanings and participants’ social relations. Using in-depth interview data from six music tastemakers and eleven music consumers, I find that tastemakers, defined as industry experts within an internationally acclaimed music company, use behavioral data to strategically manage relationships between artists and consumers, each other, and social media influencers. Through these connections, they effectively cultivate high-profile media attention, brand recognition, and fan loyalty, which in turn, elevates artists’ social status and sustains their long-term economic viability. Conversely, consumers draw upon relationships with artists, each other, and streaming platforms to construct communities, friendships, and social identities, which in turn, makes them more likely to spend more on in-person music events and personalized merchandise.