Selva Book Club: Steve Jobs by Walter Isaacson

Kiva Dickinson
4 min readJan 9, 2024

The below is taken from Selva Ventures’ Q3 2023 Quarterly Investor Letter

Book available for purchase on Amazon HERE

For the 10th installment we studied the person who will likely go down as the greatest entrepreneur and executive of his generation, and one of the greatest of all time, Steve Jobs. Walter Isaacson’s 2011 biography of Apple’s founder is an incredible lens into a unique and difficult personality who was able to champion a contrarian vision that left a deep impact on the way consumers interact with products everywhere.

Passage: If Steve Jobs had been predisposed to be kinder and gentler, would he have had the passion that allowed him to bend reality and push people to realize their full potential? A person’s good traits and bad traits are often intertwined like a double helix (…) It may not be possible to pluck out the unpleasant strands and be left with the same whole cloth that was Steve Jobs.

Zoom in on Steve Jobs the person and you quickly notice a lot of imperfection. From denying his paternity to his firstborn Lisa to bullying the people who worked for him, Jobs was a challenge to everyone in his life and a negative force to many. It can be tempting to ask why he couldn’t just be a little bit nicer, as if his predisposition to manipulate and berate could be isolated from his tendency to “think different”. Similarly, I’ve often wished for entrepreneurs to think in logical frameworks while still possessing the creativity to uniquely delight consumers. It’s been important and useful to realize that what appear to be independent traits in fact are spokes connecting back to the same hub of who a person is at their core. You can’t just cherry pick the things you like.

Passage: At the root of the reality distortion was Jobs’s belief that the rules didn’t apply to him. He had some evidence for this; in his childhood, he had often been able to bend reality to his desires. Rebelliousness and willfulness were ingrained in his character. He had the sense that he was special, a chosen one, an enlightened one.

I’ve felt imposter syndrome throughout my career, and my experience chatting with friends and mentors is that while it may reduce in time in never really goes away. I’ve tried to be less hard on myself for feeling it, and studying Jobs has been helpful in that effort as he is the example of the absence of imposter syndrome. For Jobs it stemmed from a grandiose sense of self that would be unrealistic and unattractive to the rest of us.

Passage: Sony worried about cannibalization. If it built a music player and service that made it easy for people to share digital songs, that might hurt sales of its record division. One of Jobs’s business rules was to never be afraid of cannibalizing yourself. “If you don’t cannibalize yourself, someone else will,” he said. So even though an iPhone might cannibalize sales of an iPod, or an iPad might cannibalize sales of a laptop, that did not deter him.

I’m fascinated by the fear of cannibalization as it is a powerful force in the CPG industry. The dominant CPG companies are acquiring rather than creating the next generation of wellness brands in large part because they do not want to steal market share from their largest cash-generating assets. The analyses that defend this position internally at these companies are based on indefinite preservation of the status quo. Sony couldn’t consider physical record sales becoming obsolete until it was obvious, just like Pepsi couldn’t consider the existential headwinds facing Tropicana Juice early in the war on sugar. To cannibalize oneself requires deep conviction in a contrarian vision of the future — it’s trading your bird in hand for the unknowns that lie in the bush.

Passage: Despite being a denizen of the digital world, or maybe because he knew all too well its isolating potential, Jobs was a strong believer in face-to-face meetings. “There’s a temptation in our networked age to think that ideas can be developed by email and iChat,” he said. “That’s crazy. Creativity comes from spontaneous meetings.”

I wish we could hear from Jobs on the remote work debate. Few have done more to enhance our connectivity and make productive remote work possible, yet it’s clear that he believes in the magic of in-person collaboration. Our investment in Selva’s HQ opening in early 2024 is a bet on his insight into the power of spontaneous meetings.

Please drop a comment on what you think of the format and what suggestions you have for future books. Next quarter’s book will be Outlive by Peter Attia.

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Kiva Dickinson

Consumer Investor / Founder of Selva Ventures / Proud Canadian Living in San Francisco