Almost exactly a decade ago, Steve Jobs was accompanied on stage by U2 when he introduced an odd-sounding device called the iPod and a marketplace for music called iTunes. Even now, every time a listener presses the artist button on iTunes, their thumb lands on a silhouette of Bono’s head.

I assume it has been a profitable relationship that has burnished the image of both, until now. To my mind, the bigger hair shirt should belong to Apple. Given the context, the company should have been more sensitive to the consumer’s right to be left alone — after all, the company is fresh off a hack that allowed strangers to steal, view and share nude photos of famous actresses from iCloud accounts. If the introduction of a new phone left Apple feeling a sense of largess, it could have offered music fans dozens of options of bands that they could download if they felt like it.

Bono, a singer who often takes a knee when he wants to amp up the drama in an arena, has stood tall on business matters from the beginning. Back then, the band chose a letter and a number for its name “because we could make it really big on posters.”

“We’ve always worried about the marketing, even before people thought of bands as brands,” Bono said as he nursed a Heineken backstage after a panel at the event.

U2 saw its chance with Apple and grabbed with both hands. But in this instance, Bono’s fervent desire that a passion project be heard by the masses may have gotten the best of him. We live in a time when music is meant to be pulled by consumers, not pushed on them by big rock music acts and an even bigger company.

As savvy as he is, Bono probably knew this was one U2 caper that would not go unpunished. Still, it’s surprising to see him strike a sour note, because as Jay Z might say, Bono’s not just a businessman, he’s a business, man. Bono is an investor in Elevation Partners, a venture capital firm with a futuristic bent, and he is hardly nostalgic for the good old days in the music business. From the stage, he railed against the lack of transparency in music label accounting. And even as he handed me one of the deluxe editions of U2’s new record at his house, I asked him if he felt that a physical artifact was necessary to validate the work of the artist.

“Absolutely not,” he said.

Last week, Taylor Swift, one of the biggest musical acts on the planet, withdrew her work from Spotify in part to protest the challenging economics of streaming for artists. But Bono defended the streaming model.