Ben Gilbert

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. I personally read it for the first time when faced with my first job offer to help make the decision. This was written by Marc on his old blog before starting a16z, and is now hosted on an archive of the blog.

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. It takes a bit to get rolling but I found myself nodding along over and over by the end.

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? What do you need to succeed vs. competitors for the long term? Much has been written since (including the great 7 Powers as a spiritual sequel!) but this is the foundation of it all.

The Success Equation: Untangling Skill and Luck | Michael Mauboussin | Talks at Google

This talk will break your brain. It’s like one of those proofs in math class where all the individual steps make sense one-by-one, but you’re shocked at the answer at the end. Michael unveils the crazy idea that in a 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, whatever that meant to them. Big takeaway is what we all can learn from them in our own lives. And Bill is just an incredible orator, of course.

Survivorship Bias

I think about this XKCD comic all the time.

Paul Graham’s essays

In particular, I have had big ideas stick with me for years after reading the following. I’ve excerpted a key segment from each one:

Stuff: “Unless you're extremely organized, a house full of stuff can be very depressing. A cluttered room saps one's spirits. One reason, obviously, is that there's less room for people in a room full of stuff. But there's more going on than that. I think humans constantly scan their environment to build a mental model of what's around them. And the harder a scene is to parse, the less energy you have left for conscious thoughts. A cluttered room is literally exhausting.”

Having Kids: “The fact is, most of the freedom I had before kids, I never used. I paid for it in loneliness, but I never used it.I had plenty of happy times before I had kids. But if I count up happy moments, not just potential happiness but actual happy moments, there are more after kids than before. Now I practically have it on tap, almost any bedtime.”

Black Swan Farming: “To succeed in a domain that violates your intuitions, you need to be able to turn them off the way a pilot does when flying through clouds. You need to do what you know intellectually to be right, even though it feels wrong.”

How to Make Wealth: “Wealth is what you want, not money. But if wealth is the important thing, why does everyone talk about making money?”

Startup = Growth: “In theory this sort of hill-climbing could get a startup into trouble. They could end up on a local maximum. But in practice that never happens. Having to hit a growth number every week forces founders to act, and acting versus not acting is the high bit of succeeding. Nine times out of ten, sitting around strategizing is just a form of procrastination.”

Wait But Why

Finally, Wait But Why is some of the best long-reads on the internet. Tim Urban is just so gifted at explaining complex science-esque topics, but also at creating frameworks for some of life’s trickiest decisions. Some of my favorites are The Fermi Paradox, How to Pick Your Life Partner, and The Marriage Decision: Everything Forever or Nothing Ever Again.