How to Write Longer Form Content

Dickie Bush is a full time Portfolio Manager based in New York City. He is a graduate of Princeton, where he received a degree in Financial Engineering and played on the football team.

Dickie writes a weekly newsletter called Dickie’s Digest where he shares thoughts and links on growth of all kinds, including personal, intellectual, physical, network, economic, and other forms of growth.

Dickie is probably best known as the founder of Ship 30 for 30, an online cohort based course where he teaches writers how to write better, grow their audience, and show up consistently.

In this episode, you’ll learn:

• How Dickie runs Ship 30 for 30
• How to build an online writing habit
• How to shorten your feedback loops to improve your writing
• Tactical tips to build a following on Twitter

Links & Resources

• James Clear
• The Art and Business of Online Writing by Nicolas Cole
• 30 Days to Better Writing by Sean McCabe
• ConvertKit
• Jack Butcher
• Tim Ferriss
• The Nathan Barry Show 031: Mario Gabriele – From Lifelong Obsession to Thriving Business
• David Perell
• Andrew Wilkinson
• Sahil Bloom
• Julian Shapiro

Dickie Bush’s Links

• Ship 30 for 30
• Substack: dickiebush.substack.com
• Twitter: @dickiebush

Episode Transcript

Dickie: [00:00:00]
One that accelerated my growth, every morning, Monday through Friday at 9:00 AM, you’ll get a question to reflect on where a lot of the replies become interesting pieces of advice. Right? I’m playing with one right now that I said, “Give the best advice you can in just two words.” It had 3,000 replies.

The Twitter algorithm. When people respond to something, it shows up in more feeds.

Nathan: [00:00:27]
In this episode, I talked to Dickie Bush, who works in the finance industry, but has this wildly successful side hustle teaching writers how to write better, grow their audience and show up consistently, called Ship 30 for 30. This episode we get into a ton of great stuff, how to grow your Twitter list, how to stay accountable.

We deep dive more than any other episode on the Twitter algorithm, what works, what doesn’t, some of it is pure speculation. Some of it are things that have been pretty verifiable. There’s a lot of good stuff. I think you’re going to enjoy it. I particularly love how Dickie has put together these flywheels that he’s refining each time he does a new cohort of the course. There’s a ton of momentum here. He’s just absolutely going to blow up. And it’s really, really impressive. So with that, let’s dive in. Dickie, welcome to the show.

Dickie: [00:01:15]
I appreciate you having me. Look forward to it. 

Nathan: [00:01:17]
All of our listeners are very active on Twitter. And you can’t be active on Twitter in the circles that you and I run in and not see your Twitter growth. I see Ship 30 for 30 growing, like crazy everyone, you know, posting essays and all of that. Before we dive into all of that, there’s something that I actually didn’t realize until prepping for this episode yesterday.

And that’s that everything we see online is just a side hustle for you. Can you talk about, at a high level, what you do day to day, and then, how you balance that with your wildly successful side hustle. 

Dickie: [00:01:58]
Sure. So what I do, full-time, I’m a macro portfolio manager and the way I kind of describe it as my day job is to predict the global economy and how that unfolds. And there’s only so many charts and numbers you can look at on kind of a daily basis from seven or 8:00 AM to five or six. And so my writing online and kind of journey, and that has been just a, a way to kind of step back from kind of the madness of, of markets and economies and things like that.

And explore just little interests to me. And that has evolved relatively quickly, over the last, you know, nine months.

Nathan: [00:02:38]
Oh, I’m glad you said the nine months time. I, cause that that’s roughly what I’ve noticed as well. What was that inflection point where you decided you’re going to really focus on building an online audience and, you know, start writing online?

Dickie: [00:02:54]
I guess a little bit of a backstory it’s probably longer than nine months. So I started writing online in January of 2020. With just a weekly newsletter. So I came into 2020 saying, I’m consuming all these podcasts and books and articles and just interested in learning. But my notes would end up in the back of a Notion notebook kind of into the void where, you know, there was no upside.

And so I started kind of exploring, how can I start to have a forcing function to learn more about the things I’m doing? So I just started writing a weekly newsletter. I had seen people do it and you just curation and et cetera. So that was kind of my foray into it. And I did that for about 35, 40 weeks, and started writing on a blog, exploring dabbling in some things that I was interested in, but in July, I’d probably published 30 or 40 newsletters in a row, a couple of blog posts, but just felt like I was kind of stuck and had so many ideas that I wanted to explore, but didn’t have the medium to do it. When my feedback loop was slow, I was on the weekly cadence, but it was inconsistent, et cetera. And so coming into August, I started just tweeting more and getting through these ideas. And I’m sure we’ll talk more about Twitter. It’s kind of an idea refinery, right? You can just get these ideas clear the junk that’s in your head to find out what you really want to talk about.

And so that was, you know, that was kind of the inflection point was when I made a new Twitter account in August and said, “I’m going to start to share these ideas that I think I want to talk about.”"

Nathan: [00:04:27]
As much as I want to ask there, but you said you made a new Twitter account. You just started more from scratch and kept, you know, forked off of an old one. What did you do there?

Dickie: [00:04:34]
So that one, I had a Twitter I’ve had Twitter since 2014, 2015, you know, big lifetime, just been involved with the product and loved it. And. There was a little bit of, okay, I’m going to pivot this. I had four or 500 followers at the time, had done some kind of thread curation and things like that. But my follower graph, I think was a little bit not damaged, but Twitter’s algorithm.

If you went on my account and said, who are this person similar to? It was all inactive accounts from high school. And so I just wanted a fresh slate too, kind of start over. And so I made the new account and said, Hey, I’m maki...