Hi friends,

Greetings from Silicon Valley!

I'm out here for a How I Write interview with Marc Andreessen, the man who single-handedly ruined college for me, when I realized there was no point in going to lectures because I could sit in my room and read his tweets/essays instead. The year was 2014. That moment of epiphany showed me the potential of online learning and writing, and almost a decade later, I'm still squeezing the juice from that fruit.

If you're itching to write yourself, I'd love to have you in the next Write of Passage cohort which runs from October 2nd to November 8th (but hurry, because enrollment closes in three days).

A few things to share this week:

1. The Write of Passage Grant: I want everybody who needs to be in Write of Passage to get into the course, regardless of where they live or how much money they have. So, we're offering up to two full-rides to curious and ambitious people who want to improve their writing, publish consistently, and build an audience. The application is super simple. Answer three questions. Share a link to something you've written. The deadline is Sunday, September 24th. Apply here.​
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2. My Podcast with Danny Miranda: This time, I was interviewed, and I don't think I've ever been so candid on an interview before. We spoke about finding your life's work, cultivating deep friendships, and about how I became a Jesus-follower. ​
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   (Watch the interview on YouTube | Listen on Spotify or Apple)
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   Oh, and I have a few of clips to share too: Staying focused | CEOs are sloganeers | How I met The Cultural Tutor​

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Today's Finds

Experts Talking Like Experts: I have a friend who's about to take his company public. He says that you know you're talking to a domain expert when you feel the need to frantically write down everything they're saying, because so much of it is new to you. Learning to recognize real expertise from fake expertise is a skill worth cultivating. It helps you sniff out the charlatans from people with serious game. I've picked up a few mantras: (1) great people speak in specifics, and (2) they're so comfortable talking about their craft that the rhythm and patterns of their speech don't change when they do. For a few examples of domain expertise in action, I recommend this 2.5-minute Phil Mickelson distillation of all the factors that go into a golf shot and Bill Belichick's 10-minute explainer of how the long snapper position has evolved in professional football.

​​Always Bet on Text: People often ask why I teach writing when the world is "clearly" moving towards video and audio. Gone are the days of books and in are the days of TikTok and podcasts, they say. "Always Bet on Text" is the article I share in response. The author writes, "Text is the most powerful, useful, effective communication technology ever, period." Text is unusually precise as well. Bruno Latour argued that the printing press inspired the industrial revolution not only because it increased the reach of text, but because people it allowed people to improve on specific points in an argument (or steps in the manufacturing process). Text, too, is so easy to store that before starting Stripe, the Collison Brothers created an app where you could basically download all of Wikipedia on your phone.

​Leaked Tech Emails: Exactly what it sounds like. The most revealing thing about conversations with high -evel people in Silicon Valley is how casual the conversations are. Tons of slang. Lots of typos. Billiondollar deals getting done in iMessage. Start with this thread about an Instagram cofounder talking about Mark Zuckerberg or this back-and-forth between Steve Jobs and the CEO of Adobe about hiring policies. If you're looking for more of a choose-your-own-adventure kind of experience, here's an index of all the documents they've collected.

​Preference Falsification: One of my favorite ideas from Timur Kuran. It comes from a book called Public Truths, Private Lies(here’s a written summary and a podcast about it), where Kuran shows how people lie about their beliefs to look good in social situations. As Martin Luther King once said: “Many people fear nothing more terribly than to take a position which stands out sharply and clearly from the prevailing opinion. The tendency of most is to adopt a view that is so ambiguous that it will include everything and so popular that it will include everybody. Not a few men who cherish lofty and noble ideas hide them under a bushel for fear of being called different.” Once you learn about preference falsification, you’ll start seeing it everywhere. For more ideas like this, here’s a list of 50 that shaped my worldview.

David Foster Wallace Interviews: I devoured David Foster Wallace’s interviews for his takes on the American spirit and the darker sides of consciousness. His writing is uniquely perceptive, but also sad, dreary, and at times, haunting. History will remember him as one of the most iconic authors of the late 20th century. Start with this unedited interview, which is as revealing as it is awkward. Then, watch his interview with Charlie Rose. This YouTube comment says it all: "Homeboy grapples with every single word, and every single idea, and drags it from the pit of his soul. Watching him grimace after answering questions is strangely compelling and also devastating." The guy was tender and tortured. What stands out is the way he's tormented by attention, poor performance, and the tens of thousands of people watching the interview. Rest in peace, DFW.

How I Write

​Derek Sivers belongs on the Mount Rushmore of online writing. He's a master of short articles, invented the concept of the "Now" page, and has pioneered new business models for online writers by selling all his books direct-to-consumer on his website.

Here's what I learned from our interview:

1. When Derek finishes writing a book, he goes over every sentence to ask himself: Is it worth killing a tree for this one? Then, he deletes everything that doesn't make the cut.
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2. Marketing is the final extension of your art. It’s not the enemy of your work, but rather your biggest friend.
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3. Pour your personality and philosophy into the way you do business. People actually appreciate it when you do things in a surprising way. It shows you care more than most — that you’re putting your self into this — and that you’re not just in it for the money.

Listen to the episode on Apple or Spotify.

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P.S. I came to interview Marc Andreessen about writing, but left with a PhD in obscure Silicon Valley history and a list of book recommendations large enough to fill The Library of Congress.