πŸ“» β€” Content Creation, Community, and Monetizing Audiences with David Perell & Jimmy Song

Reading Time: ~ 6 min.

Good morning yenizens!

Before we jump in to the deep-dive, here are a few links of high-value:

  1. You are not the default by Holly Liu
  2. Orbit raises $4M via a16z β€” πŸŽ‰
  3. Contrarian Thinking β€” Everything Codie‘s written has been great (so far)!
  4. Creator Grants via Makerpad β€” Wonderful opportunity!
  5. The Community Playbook by Flybridge β€” Whoa. Yes.
  6. Critical Lessons from Startup Community Building @ Instagram

And finally, one of our amazing readers and yenizens, @authorettestory, connected me with a long-time friend Chris Brogan!! And, as a result, we’re scheduled for a podcast this coming Monday!!

I love this community, seriously. So amaze.

To infinity & community,

β€” john


David Perell is known for many things (and many names, like “The Writing Guy”) but the one thing he’s most-definitely figured out is how to maximize content on the internet and he’s on a mission to help others do the same:

I’m on a mission to teach thousands of people to write online, share their ideas, and build an online audience.

via Perell.com

He sits down with Jimmy Song and has a candid, fun chat about creating content, building communities, and monetizing audiences β€” here are my essential notes from their time together.

Oh, and he’s terribly quotable.


Currently, David is writing 100 articles in 100 days and is building a system to help folks learn how to write better that doesn’t sound like a traditional text-book or how-to:

I want to communicate writing advice in a way that doesn’t sound like writing advice β€” in a way that’s fun and interesting.

David Perell

How did you create this career for yourself?

In David’s telling, a “total accident” β€” he was, admittedly, a “terrible” writer and didn’t perform well in school. Because of those failures, he been intentionally on honing his craft, spending more time reading (as well as writing), and thinking differently about largely-held beliefs; for instance, in response to the Peter Thiel Question, David responds:

I believe that writing online is the biggest arbitrage opportunity in the world right now.

This is largely due to the growth and availability of distribution channels.

How did you gather the courage to teach others to write?

David has always loved performing and through his competitive play on the golf greens as well as being a tv producer / director for his college television channel. As a result, these live features allowed him to intentionally work on his communication skills in a variety of scenarios and environments.

David also shares his intense focus on just a small number of topics and themes; a powerful reminder about how you don’t necessarily need a wide-range of skills to create meaningful work (and income) online.

Inspired by folks like Ben Thompson of Stratechery and Charlie Munger, he “doubled down” on the scale of the internet and decided to “produce, produce, produce!” β€” it’s worked.

As he shares, the only way that you can become better at writing is by writing (and writing a lot) β€” through sheer repetition. He borrows heavily from his discipline on working and training towards making a D1 school for the sport.

Consequently, through his practice he has gained the confidence that was created through “doing the work” and helps train others to think (and do) similarly.

Where do you see education for content creation going?

Two things:

  1. Notetaking
  2. Hyperlinking

David shares his belief that building a persistent repository of knowledge for oneself that, over time, increases the number of connections exponentially. The result? A “web of ideas that you can always borrow from” β€” a competitive advantage for the technologically-inclined!

Now, one can write from a place of “abundance” and being able to curate one’s ideas, a “collage”, of who we are and what we’ve done.

The future of education as it revolves around content is creating these digital reserves and being able to summon those at-will through notes and hyperlinks.

How has podcast and video creation changed?

For David, he uses a similar, systematic approach to how he thinks and creates content:

  1. Knowing the difference between converging conversations and diverging conversations and how you should engage with both depending on context. For instance, in a podcast, converge to a point after each question while in a room with friends, diverge to open it up.
  2. Cycles in audio, a repetitiveness to a singular theme that we’re going to come back to over and over again in the interview. This helps absorption.

How does rhetoric play in content creation?

David says it plainly:

The world rewards the people who know how to best communicate the ideas that exist, not the people who have the best ideas.

David Perell

Studying the formation of words, sentences, structures, placement, and the addition and/or elimination of even the slightest of words, phrases, and punctuation can dramatically impact (and improve) one’s writing β€” wordsmithing, just like engineering software.

This is why David believes that software programmers are particularly adept at writing because of how they more naturally see language in this way.

How do you get better at something?

Two things:

  1. Practice
  2. Feedback

He uses both Trump and Chris Rock as examples of how they are practicing in smaller arenas to practice and test-drive their speeches and programming. They listen (and experience) the feedback through silence, pauses, and more. They know that they have to “bad is where you start“.

This is what you do with writing and, if it were up to David (and his followers), you want to produce as often as you can. And, if you do, you’ll begin to experience the compounding effects of this simple workflow. Writing, for me, has been the most important investment of my entire life.

There are a number of thoughts around video creation that are worth sharing plainly, especially as it relates to art:

  • There seems to be a “right” mix between too often and not enough. With video, especially, it can take more time to “absorb” from David’s perspective.
  • There’s a cadence and rhythm of creating a series of steps toward a climax instead of offering that type of event all the time.
  • Writing matches the cadence of speech a lot more than folks realize.

In David’s program, for instance, they use the acronym C.R.I.B.S.:

  • Confusing β€” If something’s confusing, change the wording.
  • Repeated β€” If it’s repeated, delete it.
  • Interesting β€” If it’s insightful, double-down on it.
  • Boring β€” Change the wording.
  • Surprising β€” That’s the “bass drop” or the climax of the piece.

Identifying these breaks or ways of analyzing writing (and then making it better) can become a flywheel for better writing.

What about “fiat education”?

Academic writing is extremely precise but it sacrifices for speed and distribution. The internet allows for what David calls a “beautiful challenge” which is the competition to get the attention of the best minds and thinkers in the world to read what he writes and give him the feedback he desires to further his development and reach.

πŸ‘†πŸ» β€” I really do love that! πŸ₯°

And David’s metaphor of dancing and dance partner is well-worth the listen but in summary it’s about the writer being the “lead” partner and the audience being the other who is actively participating in the dance but who is not in control. Meaning you, as the writer, are always in control, not doing it for the audience alone because without them you couldn’t dance in the first place.

What do you think about monetization and the future of content?

David puts it plainly:

I believe that the wealthiest people in the 21st century will be those who have audiences.

When it comes to the actual mechanics, he sees it in three parts, order from least to most profitable:

  1. There’s advertising
  2. There’s subscriptions
  3. There’s audience-first, influencer-driven products

His bottom-line, in terms of revenue generation, is building and selling a product β€” a product, as he puts it, that transcends your name.

One angle that he also shares is a focus on curation as the source of new creators, not just content.

How do you manage the junk content out there?

David uses filters that help him mute most of his distractions β€” he allows himself a few select distractions and websites but the intention is clear: Only visit sites that will improve his end goals of content creation.

What do you see as important for the future of bitcoin?

David shares that Bitcoin needs to do a better job of telling their story, the narrative around what cryptocurrency is and what it can do.

Whew! There’s more to this, of course, but those are my notes from this great show:

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