Ben Gilbert: Career Planning, Seinfeld, Psychology of Money, Skill and Luck, Survivorship Bias
Our curator this week is Ben Gilbert (@gilbert). Ben is the co-founder and co-host of Acquired, the podcast about great companies and the stories and playbooks behind them. What started as a side project in 2015 has become a phenomenon in business and tech culture—the show has over a million listeners, has been ranked #1 in Technology on Apple Podcasts and Spotify, and has sold out live shows at Chase Center and Radio City Music Hall featuring guests like Mark Zuckerberg, Jensen Huang, and Jamie Dimon. Previously, Ben co-founded Pioneer Square Labs, a Seattle startup studio, and shipped the first version of Office for iPad at Microsoft.
Please enjoy these words that have mattered to Ben.
Ben Gilbert's Picks
Marc Andreessen's Guide to Career Planning
This is the single best resource I can recommend to anyone in college (or after!) trying to figure out what to do with their life.
Tim Ferriss Show – Jerry Seinfeld
Jerry is possibly the greatest comedian of all time. And this interview gives you a sense of how and why that happened. His observation that comedy "is writing" stuck with me. He's a grinder through-and-through.
The Psychology of Money by Morgan Housel
This is, no doubt, the book that most impacted my life in the last 5 years. Morgan is just a ridiculously talented writer. It is ostensibly about finance, but really opens up the big questions about how you want to live your life.
"What is Strategy?" by Michael Porter, Harvard Business Review
It is a classic for a reason. This is the single best read I've found on business strategy. Why do some businesses endure while others are a flash in the pan?
The Success Equation: Untangling Skill and Luck | Michael Mauboussin | Talks at Google
This talk will break your brain. Michael unveils the crazy idea that in an ever-more-globally competitive world, it is actually luck that governs the winners all the way at the top.
How The Economic Machine Works by Ray Dalio
A wonderfully-illustrated video explaining economic cycles, debt, and consumer behavior.
Runnin' Down a Dream: How to Succeed and Thrive in a Career You Love - Bill Gurley
Three great stories of some of the best to ever do it in different fields. Bill details their journeys to create greatness.
Survivorship Bias
I think about this XKCD comic all the time.
Paul Graham's essays
Key essays: Stuff, Having Kids, Black Swan Farming, How to Make Wealth, Startup = Growth.
Wait But Why
Some of the best long-reads on the internet. Favorites include The Fermi Paradox, How to Pick Your Life Partner, and The Marriage Decision.
Excellent curation of foundational reads. The inclusion of the XKCD survivorship bias comic is clever, especially alongside Mauboussin's talk on skill vs luck. These two pieces work together well sinse they both challenge the narrative that success stories follow a replicable formula. I remmber applying this lens when evaluating startup advice, realized most "how I built this" stories completely omit the timing and market conditions that were just luck. That combo forced a way more honest assessment of what's actually controllable.