What did you wake up thinking about this morning? “Why did I set my alarm so early?” And then I remember this is the only time I have to exercise, and I’m energized. My most cogent thoughts come while running. It’s during that hour to myself when I organize my thoughts, solve problems and have my best ideas.
What will define your career in the coming year? The streaming music service we’re launching. Jimmy Iovine and Trent Reznor have a vision unlike anything existing in digital music, and I’m looking forward to spending the next year of my life making that vision a reality.
What will define the evolution of digital music in the next five years? The next evolutionary phase of the Web is curation by trusted sources. The magic of the Internet is access to limitless stuff. The greatest Internet applications have all been filters on that stuff. Technology has brought us so much change in the past 20 years. What hasn’t changed is that we are still humans with limited time. We’re looking for the information and entertainment we love most with the least amount of effort to fill that limited time — high signal, low noise. Humans don’t respond to recommendations from robots. Collaborative filtering can get very good at predicting something you might be interested in, but still humans value a recommendation from a trusted source, even if it’s for something they aren’t likely to enjoy.
Describe a lesson you learned from failure. Being too early is the same as being wrong. At Winamp/Nullsoft, I tried to license MP3s in 1999. At Yahoo, we launched the first $5-a-month, all-you-can-eat subscription music service in 2005. Both were the right ideas, but attempting them before having a critical mass of smartphones and mobile networks was foolish in hindsight. Timing is everything.
Who is your most important mentor, and why? There is no telling where I would be without the Beastie Boys, John Silva and the Silva Artist Management team. When I met them in 1994, they had a much clearer vision of how the Internet would impact media than I did. For the past five years I’ve had the good fortune of working with Peter Gotcher, the founder of Digidesign, on Topspin. Peter’s spent his life building smart businesses adjacent to music without letting the industry’s past stand in his way.
Name a project that you aren’t affiliated with that has most impressed you in the past 12 months. The flood of information the Internet has brought into our lives is amounting to a health and fitness revolution. Watching companies like Fitbit, 23 and Me, and the Whole Life Challenge change the lives of friends and family has been inspiring. The Internet and game theory changing lives — wow!
Name a desert island album. “Fresh” by Sly & the Family Stone. This album is the reason Sly’s been tattooed on my shoulder for the past 20 years. I still listen to it weekly.