Week 1: Copywriting, Being Undefinable, and Ideas to Words

Welcome to the first edition of my weekly newsletter, where I share interesting ideas I’ve come across for the week. This is different than my Substack blog, which will primarily serve long-form essays, infrequently posted.

If you’re not interested in the essays but not the weekly side of things, feel free to unsubscribe. Seriously, I really don’t care if you do lmao.

Personal Updates

This past week, I’ve had the honor of interviewing Mitchell Earl, the CEO of Praxis, an alternate college apprenticeship program teaching students life skills to crush it in their careers.

We talked about the relevance/irrelevance of a college degree, skills for a great career, curiosity-driven learning, living life with intentionality, and much more.

I’ve also recently published a new essay called, “The Deification of the University Clock Tower.” It’s a slightly controversial, but thought-provoking piece on why we shouldn’t conflate knowledge with how much time we spend in the classroom. 

This essay was primarily influenced by a chapter in Michael Gibson’s book, Paper Belt on Fire. It talks about the contrarian founding of Thiel Fellowship and how it had to navigate the criticism of many university leaders.

Learnings

1: Learn Great Copywriting with Harry Dry

As a big fan of the How I Write Podcast by David Perell, this episode was by far one of my favorites. Harry Dry was one of the most articulate, fashionable speakers I’ve ever come across. Here’s what I’ve learned:

• You should judge an ad based on how much it sells.

• Write copy that cannot be copied.

• If you can ever make your customer feel like they're making a smart decision, you've done something right.

• One of my favorite ads, “1,000 songs in your pocket,” uses metonymy, a short hand term that stands in for a literal term. Absolutely genius.

• Writing simply = rewriting simply.

• Kaplan’s Law of Words: words that aren’t working for you are working against you.

• A good writer arranges ideas in a way that haven't been laid out before.

I used to associate copywriting with sleazy salesman manipulating words to force you to buy their shitty product. But from this episode, I’ve realized copywriting is a form of art, just like poetry. As David Ogilvy, one of the greatest advertisers of all time, writes:

2: Become Undefinable

I’ve been following Dan Koe for a while, and he writes some pretty banger tweets. In the past year, I’ve completely de-attached my identity pursuing a predictable path in life and have pursued a state of perpetual wandering.

I’ve been pretty all over the place recently – creating music films, running, writing, podcasting – but I’m certain all these creative energies will point me in some direction as I continue creating.

I have no idea where I’m headed, but maybe that’s a good thing.

3: Putting Ideas Into Words

I’ve been learning a lot about writing recently, and Paul Graham is someone I greatly look up to – not just as a startup bro but as an incredibly articulate writer.

Here’s what I’ve learned from reading this essay:

• Putting ideas into words is a severe test.

• The real test is reading what you've written. You have to pretend to be a neutral reader who knows nothing of what's in your head.

• A great deal of knowledge is unconscious, and experts have if anything a higher proportion of unconscious knowledge than beginners.

• No one who hasn't written about a topic has fully formed ideas about it. Someone who never writes has no fully formed ideas about anything nontrivial.

• Ideas can feel complete. It's only when you try to put them into words that you discover they're not.

One Question

Something I’m trying to incorporate more is sparking conversations with my readers instead of making things seem so one-sided.

So every week, I’m going to end each newsletter with a question — sometimes serious, other times quirky and random. So for this week’s question:

Reply to this email with your answer! Would love to hear from you :).

See you in the next,

Jeston