This episode of A Productive Conversation features Chris Dalla Riva, a musician, data analyst, and Senior Product Manager at Audiomack who bridges the gap between creativity and analytics. Chris joins me to discuss his book Uncharted Territory: What Numbers Tell Us About the Biggest Hit Songs and Ourselves.

As part of his research, Chris listened to every Billboard Hot 100 number-one song—nearly 1,200 of them—tracking trends, rating songs, and discovering how randomness, technology, and taste shape what becomes a hit. We explore the intersection of numbers and nuance, how data can deepen our understanding of art, and what the patterns of pop music reveal about us.

Six Discussion Points

• The origin of Chris’s experiment to listen to every Billboard number-one hit
• Why Bob Dylan never topped the Hot 100—and what that says about luck and timing
• How data, subjectivity, and quality intertwine when rating songs
• The cyclical nature of musical trends, from movies to TikTok
• The uneasy relationship between music and technology—from Auto-Tune to AI
• Why the album format—and vinyl—still matter in a streaming world

Three Connection Points

• Check out Chris's newsletter
• Buy Chris's book
• Read Mike's essay, The Sound of Time

Chris and I cover a lot of ground in this conversation—from Bob Dylan’s surprising chart record to the influence of AI on modern music. If you’ve ever wondered what hit songs say about culture, creativity, and ourselves, this episode hits all the right notes.