An all-too-typical email from an earnest founder (“How do I know which of my ideas will ultimately command the highest valuation…”) reminded me of Steve Jobs’s explanation of why Apple triumphed over Microsoft’s Zune with the iPod. His words about motivation shed light on an oft-overlooked factor in the age of entrepreneurship:

"The older I get, the more I see how much motivations matter. The Zune was crappy because the people at Microsoft don’t really love music or art the way we do. We won because we personally love music. We made the iPod for ourselves, and when you’re doing something for yourself, or your best friend or family, you’re not going to cheese out. If you don’t love something, you’re not going to go the extra mile, work the extra weekend, challenge the status quo as much." (from Walter Isaacson's Steve Jobs)

Love doesn’t factor into the sterile calculous of today’s valuation-obsessed start-up culture nearly enough.

I was struck by a similar description of Jeff Bezos’s affections in shaping the strategy that propelled the Kindle, a product category that most folks had consigned to the dustbin of history at the time Amazon undertook its development:

“Bezos’s colleagues and friends often attribute Amazon’s tardiness in digital music to Bezos’s lack of interest in music of any kind... Steve Jobs, on the other hand, lived and breathed music. He was a notoriously devoted fan of Bob Dylan and the Beatles and had once dated singer Joan Baez. Jobs’s personal interests guided Apple's strategy. Bezos’s particular passions would have the same defining impact at Amazon. Bezos didn't just love books — he fully imbibed them, methodically processing each detail. Stewart Brand, the author of How Buildings Learn, among other works, recalls being startled when Bezos showed him his personal copy of the 1995 book. Each page was filled with Bezos’s carefully scribbled notes.” (from Brad Stone’s The Everything Store)

(Interestingly enough, you know what else Jeff Bezos has loved all his life? Outer space! In fact, In his high school valedictorian speech, he outlined his “dream of saving humanity by creating permanent human colonies in orbiting space stations while turning the planet into an enormous nature preserve.” And I thought Blue Origin was just a crazy billionaire’s club thing…)

So what did I tell the earnest founder?

“May I suggest a better question: What do you love?”

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