The Nathan Barry Show
The Nathan Barry Show
035: Dickie Bush - How To Make $100,000 Writing on Twitter

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

Dickie Bush’s Links

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 making a new account when I kind of reset this thing. And so I didn’t also have like tweets from high school and things like that in there.

so I just started fresh and it felt like a good way to do it.

Nathan: [00:05:19]
So you made a new account. Did you slide over like, you know, swap the same username or is it a different username?

Dickie: [00:05:26]
I swapped the username. So cause that one, it’s just thinking like, I didn’t want to lose it. So yeah. I changed the username on the old one, made the new one and then change back. So.

Nathan: [00:05:34]
Yeah. And you have that, that brief 45 second window where you’re

Dickie: [00:05:38]
Yeah. And like sprinting, I’m like, Oh, there’s hundreds of people who are about to steal it. Yeah. They’re just counting down.

Nathan: [00:05:42]
So that’s the first time I’ve heard the, like the Twitter algorithm or this idea of a damaged account.

Can you talk about that more?

Dickie: [00:05:51]
It’s a total hunch. Right. But now if you go on my account and it might’ve just been, I didn’t have kind of that breakthrough or followers, but it was. You know, now when you go on my account that people, similar to, or other people in kind of our Twitter sphere. Right. Whereas in the old one, I was engaging in that community, but it was just inactive.

So I, you know, I have no proof to back it up, but I was able to kind of grow what, sell more quickly right after.

Nathan: [00:06:22]
Yeah, that’s interesting. And I wonder how that plays into it.

But I could totally see that of Twitter being like, I don’t know, the guy’s just tweeted about random stuff for five or six years. Like, what do you want me to recommend them for? And then you’re like, no, no, no, this stuff. And you’re like, okay.

But that’s like 2% of what you’ve ever tweeted. Yeah. Got it. So,

Dickie: [00:06:42]
Yeah, there’s something there, but I don’t know.

Nathan: [00:06:44]
I’d love for someone to run some experiments on that and see if, how much that matters. But, one takeaway from it that I appreciate is you didn’t just say like, Oh, here’s a new thing that I’m doing.

Let me lean that direction. You said, no, no, no. This is something that I’m taking seriously. We’re going to go all in on. And really you didn’t, you weren’t attached to the sunk costs. You know, or like I, but I I’ve already 500 subscribers, then I’m going to throw that away. It was just the approach of like 500 is not going to take that long to get

Dickie: [00:07:16]
It was almost like an acceptance of an inconvenient truth because I did have that sunk cost for like two months of like, Oh, I have 500 followers. And when I made the new one and said, Oh, I’m making this new one, like 45 came over. Right. So, so many of those were inactive accounts as well.

So it was kind of this mental thing of like, Oh no, I can’t give this up. But it was clear that I really hadn’t done as much as I thought.

Nathan: [00:07:38]
So that’s interesting. Cause that’s the, you know, the person

With an email list that they’re proud of, but with a terrible open rate and they’re still like, I have 10,000 people on my list and you’re like, yeah, but you have a 5% open rate, but you don’t have 10,000 people. And they’re like, no, I have 10,000, you know?

And it’s just like, you got to accept the reality and realize that. Now you’ve got 500 people that actually are paying attention to you.

Dickie: [00:08:00]
Yeah, there’s, there’s tons of, like. Goodhart’s law or just whatever, whatever it is, where you have this indicator of like, Oh, I have 10,000 email X, but now you’re, you’re spot on.

Nathan: [00:08:10]
Yeah. So how many subscribers did you have, like last July when you sort of started to take Twitter and writing more seriously or just before that?

Dickie: [00:08:17]
On my newsletter, I had about 200 and that was over 40 or 35 weeks. And, you know, I probably signed up about half of them. And I, I hadn’t done much on the growth side. I just was kind of writing it and saying, now this is fun. It’s a forcing function. What have you? And, I started that Twitter account really with about a hundred.

So relatively small, to start.

Nathan: [00:08:43]
You know, at that point it sounds like you, you transformed it from like journaling. Here’s what I learned all of that to actually focused on, on growth. Is that right?

Dickie: [00:08:54]
Right. It was, I started to just, I, I took a look at all these things, what I, to basically done in the nine months leading up to that was built up this idea of a blog post in my head where it’s like, Oh, I have to sit down and write this thing and edit it and get feedback on it. And so it just had this super slow feedback loop.

And I had this massive list of ideas, like, Oh, all these different areas I wanted to explore, but no medium to do it. And so what Twitter became was just, I could share these one-off ideas, Write, feel like, do a little bit of writing, make these small bets on if things resonated. And then at the same time to kind of have just more eyeballs on there.

So I wasn’t publishing into the void. I took what I was doing on my newsletter. you know, Podcast curation and started just summarizing the ones I was listening to. Right. And people appreciated that it made them more digestible. So it was kind of this, this, value add while I was exploring these more ideas.

Nathan: [00:09:51]
Yeah. And that’s interesting. I think, I probably do the same thing of like building up, like my favorite blog posts that I read are from where you can tell someone to put a huge amount of time and effort into it. And it’s polished detailed Research. Do you know whether it’s a piece from like someone like James clear or, you know, I love these like complete guide type posts.

And so I find myself waiting, you know,

And I might publish four of these a year or something myself, but. Exactly. As you’re saying, there’s a lot more ideas out there. And a lot of unrefined ideas that if you’re not careful, like that’s the unrefined ideas, what’s going to make it into your, like your long form detailed blog post.

Dickie: [00:10:34]
Well, I think it’s important. That’s an important point because now you can publish for a year because you have a credibility to it. Where in the beginning you could publish the ultimate guide, but there’s not really anyone who sees you as an authority in that area. Right? So in something we preach and Ship 30 is you have to just get these ideas out there and work through a lot of it.

Where people are going to come to your blog later, once you’ve kind of built a small following versus people just finding their way onto your blog, right? So its kind of a chicken or egg problem. And that’s why I think the beauty of Twitter is you can start to accelerate these feedback loops, versus just kind of publishing into the void.

Nathan: [00:11:16]
Yeah. Yeah, that makes sense. So something that you’re doing

A lot, and I’m curious when this started is playing around with different formats for tweets. You know, and, and really with Ship 30, I’ve seen you popularize that a lot of having a headline, you know, you’re leading in the tweet itself and then the essay, as an image, when did you start to notice that working and was that inspired by anybody?

Dickie: [00:11:39]
So I’ve seen it all over Twitter early on. not early on, but a couple months ago where I think the very first one was, I can’t remember his name, but he, he was doing like venture capital, blogs, like blogs in a single screenshot. And I loved the media. Right. It’s like Twitter is a horrible place for long form content.

Well or medium form content. I should say, Write threads are kind of they’re just a little bit clunky, right? There’s a time and place for threads on like, Poignant advice and things like that, but there is a, sometimes you want to read something like that. And so the atomic essay is just a way to tweet something, expand on it all in the same medium.

Right? So it’s like you said, with the lead in, you put something out there. If people want to read more, it, they can click on the image, read it, but it’s also kind of a standalone, whatever it is at the top. Right? So it’s like this optionality that you create. That leads and it’s kind of a, it’s a scroll stopper, right?

People stop on images versus a, just a sea of text. And it’s easy to kind of scroll through.

Nathan: [00:12:45]
Yeah. And what’s interesting about it is also the load time. I have spent a lot of time in user experience. You know, I got started in designing mobile apps and, and just people have really interesting. behaviors when they’re on their phone, especially, if the, the internet connection might not be the best and all of that.

And you just see so many people click through to a site, let’s say it’s currently popular on hacker news that day, and it’s overwhelmed. And the server’s loading slowly. And they’ll just click right back out and move on because it didn’t load fast enough. And there’s also just this unknown of sure. I clicked through this link, but what am I actually getting?

And Twitter tries with the Twitter card, sort of give you a little preview maybe. but the expectations and the load time are

Things that I don’t think you should underestimate with. You know, what you’re calling in a telematic essay of just clicking right in. And I know. You got to fit the whole thing in that screenshot.

And so, you know, it’s going to load super fast and I only have to commit to reading it for, I don’t know, the next 45 six.

Dickie: [00:13:51]
And it’s, it’s something we talk about. And it’s a quote from Julian Shapiro. That’s where I, first of all, it is people don’t have short attention spans. They have short consideration span. And so it’s a, it’s an empathetic writing medium, right? It’s like, you’re not going to have to read very much. We try to say that you better grab attention even in your atomic essay in the first line, because people can just swipe it away.

Right. So it’s like a, it’s a way, it’s a way of thinking of, we’re not asking you to do very much by reading. This is clearly not going to take you all day. you can swipe away if you want. And yeah, the load time is interesting too, cause it’s always right.

Nathan: [00:14:25]
You named it and atomic essay, is what impact do you think that has had on, on, you know, giving it a specific brandable name?

Dickie: [00:14:35]
It made sense to me as I see these as the building blocks for a lot of longer form content. And these, like you said, these, these blockbuster blog posts are really 15 or 20 writing sessions boiled down and kind of put all together where you could take one of the sections and it could be a standalone blog for a lot of them.

So we see it as like this building block, atomic chemistry. What have you, physics, a lot of these longer form ideas. And so it just brings down the friction. It’s I’m not publishing anything long It’s I got to take one idea. I got about 200 words of space and I’m going to do it every day for 30 days.

So all of these things kind of make it of lowering the, shaky hand to hit publish. Take all that friction away and make it as small as possible.

Nathan: [00:15:29]
Yeah. I love it. You know, so many people obsess over word, count, obsess over. I was going to say substance, I think, I mean more like making it really impactful. And so, you know, if you’re publishing on a weekly or a monthly cadence, then you’re putting so much more pressure on yourself. And so, or they’re doing other things where they’re saying I’m going to write every single day and it never leaves their computer.

I’m curious as you made this pivot, Ooh, you know, last, last July last August, what did you notice different in your own writing habits and maybe what were some of those examples of ideas that got refined? You know, when they actually, I guess, hit the market rather than just being inside your newsletter.

Dickie: [00:16:13]
I think first and foremost, I learned to write quickly the part of the constraint is we say under 250 words, try to do it under 45 minutes and just get in the habit of being okay with B plus quality, with a plus consistency in the beginning. Right. Earn the right to focus on quality by getting through and building this consistency.

And then. So that was kind of, for me, my ability to sync has gone through the roof to where it’s like, I have this every single morning, this Coliseum to do, thinking on a single idea where anything I’m kind of want to explore further, I get 45 minutes to an hour to try to refine it. And the. The constraints of it, of getting it down to 250 words really improves my ability to kind of work through it in a, in a simple way.

So it’s all of these things that just bring my thoughts a little bit more coherent.

Nathan: [00:17:15]
Yeah. That makes sense. and then are you still bringing it to long form essays or you found that you’re really focused on, on the shorter, medium?

Dickie: [00:17:24]
So I haven’t, I’m disappointed in how much long form writing I’ve done, just because building the business side has kind of taken a lot of the long form content. So I’m still publishing along. I’m about to hit my 100 and at that point, I’m going to start to flip back through them because I’ve a lot of the things.

Like my threads have been, you know, expanded upon atomic essays and things like that. So I had this foundation that I’m looking to put on a blog or on a whatever from here, but I just haven’t found the time. So I got this big backlog and eventually I hope to kind of pivot into, into the longer form.

Nathan: [00:18:01]
Yeah, well, it’s interesting. I’m, I’m thinking about the number of ideas that I’ve been putting down and writing into a book and found that because that format requires so much thought and structured and they all almost should be accompanied by. This other side of the really casual, like it here for a high friction of we’re going to put it into a traditionally published book.

These are well-refined ideas. Then we should have the opposite of anything here is where there’s complete freedom.

You have to publish. I love the time constraint of like, try to do an under 45 minutes, and just iterate quickly and refine those ideas.

Dickie: [00:18:42]
So we think the constraints are the biggest part of it, right? Any I’m writing a down on this now it’s like there’s seven or eight different constraints you can have as a writer and decisions. You can make, you know, medium platform, topic, length, time to Write publishing and. Every ounce of thought you put into those decisions takes away from your rights.

So everyone that comes into Ship 30 it’s like here are the eight things you might have to decide, and we’ve already made them for you. Now go Write everyday for 30 days, we give you the templates. We give you all of the things you need. It’s like, okay, just explore 30 ideas now. And we, the creative freedom that we see it unlock is, is tremendous.

Nathan: [00:19:25]
Yeah. Okay. So let’s talk about, for a second about the format of Ship 30 and. So you it’s a, a course, you know, cohort based course that you’re running monthly. How many months have you been running it now?

Dickie: [00:19:38]
So it’s every six weeks just to give a two week break in between kind of reset. so the very first one was in November and we’re on cohort number four Day 16 and today’s April 14th. So yeah, we’re on the fourth cohort right now.

Nathan: [00:19:52]
I had, like in first reading, I had seen it as monthly and I was like, that must be crazy to go 30 days, like, and just

Dickie: [00:20:01]
Yeah, we found it, with, with off-boarding and trying to make improvements like the two week between each one has just been a heads down sprint of how can we make this better? What can we learn from our off-boarding and how can we Ship as many new features? and so that’s always a fun time, but yeah, it’s about every six weeks.

Nathan: [00:20:17]
So is it a ramp up? And then like when I sign up as a student, is

Dickie: [00:20:23]

Nathan: [00:20:24]
up over our first week? Or take me through that experience?

Dickie: [00:20:26]
You will sign up. We drip you through like a resources sequence until the start of onboarding week. So onboarding week will start one week before the first day of the 30 days. So on that Monday, You’re brought into the community Slack. We take you through a pretty comprehensive onboarding where, which is when you take the, how to Ship 30 for 30 course, which is, are just, it’s a, it’s a writing course, but it’s really a habit design course.

We give you everything you need to set up your daily writing workflow, all the templates and everything, and then work you through some more resources. Get you introduced to the community, sets you up in your accountability partners, et cetera. And then on Monday, you’re ready to hit the road.

Nathan: [00:21:05]

So, and then before that you’re talking about dripping it. So if I were to sign up say, let’s say I were to just miss, you know, sign up for one cohort and I’m like, Oh, the next one sounds interesting. I could buy that. Today. And then I would receive that Content timed out, you know, over a couple of weeks.

Dickie: [00:21:25]
So you wouldn’t have access to the actual how to Ship 30 course. We put that just as the week on this, these are more just how to improve your writing Podcast articles, you know, things like that. And then on the first day you are entered into a 30 day email course written by Nicholas Cole. Who’s just one of the most he’s my business partner.

And. The master of online writing in my opinion. And he put that together every single day, you get a prompt if you’re running out of ideas and then kind of an actionable piece of writing advice on crafting headlines, gathering attention, distribution, those kinds of things.

Nathan: [00:21:59]
Nice. Yeah, that’s great. Something else I noticed that you do, in your pricing is that the pricing changes as it gets closer to the date. Can you talk about that?

Dickie: [00:22:09]
Yeah. The, we like to have a good sense of how many we are going to have. and there’s also a bit of the most public momentum on it happens at the beginning of each cohort. Right? So on day one through five, we’ve been on kind of a two week, two week break. And so during that first week and a half people that are unfamiliar are going to be greeted with a bunch of new essays.

And so we try to capture that momentum in saying, Hey, if you want to sign up now, like you’re going to regret it later if you don’t pull the trigger earlier. And so it’s just a, it’s a way to incentivize early sign-ups and that gives us more clarity on the size of each one.

Nathan: [00:22:50]
Right. So it’s something I. I’m realizing I’m relying on a screenshot from my notes, but the pricing being like one 99 until April 5th and then two 49 until April 26th and then two 99 from April 20, 2016, up until close. So, you know, it’s basically saving 30% if you sign up today rather than say, Oh, that’s so cool.

I’ll totally do it. And then in 20 days from now, when it’s actually time to sign up being like, Oh yeah, I’ve, you know, I’ve got busy or whatever else.

Dickie: [00:23:21]
Right. It’s all about taking action. And so that’s what we try to incentivize.

Nathan: [00:23:25]
Yeah. So how do you think, the balance in, right in the product that you’re selling of in Ship 30 for 30 it’s obviously courses, Content, accountability, and all that. How do you think about the balance between a course like in the, the content and the structure that you’re selling versus the accountability of like, look you have.

You have all the ingredients, you, you just need someone to say like, like hold you accountable to Shipping and, sitting down and doing the writing.

Dickie: [00:23:55]
Yeah, it’s a, we try to front-load the. Here’s everything you need. And then the 30 days give as much accountability as we can. So we have office hours sessions. We have a, popping into Slack. We have accountability partners. It’s we try to say, okay, if you have all these things in place to sit down on the first day of the 30 days and start writing, no matter what Day 11 is going to be hard.

And so how can we intervene in that and continue to give you new ideas, engage with friends, bounce things around, you know, that is so it’s like a Content Content Content course to begin. And then all about accountability.

Nathan: [00:24:37]
When you’re running the same cohorts, you definitely see those trends of like, alright. Day 11 is hard. I can totally imagine that. The number of times that I’ve had a daily writing habit. Start or any kind of daily habit practicing the piano, you know, running or whatever else.

And you hit basically that like day seven, you’re like, yes, I’ve got a streak and then Day 10, 11, 15, somewhere in there. You’re like, damn it, this is hard. This is a lot

Dickie: [00:25:03]
Exactly. And we track a lot of that data where we’re attracting the analytics to our web app, where you publish the essay and we’re able to see, as people started to fall off, what can we do? And we’ve learned from the first three lines. If you can get to Day six or seven with some momentum, you’ve got a good chance.

And then you’re going to face another struggle around day 15, we call it the debt. Just, you know, Seth Godin’s the debt. It, it happens to everyone. And so we really intervene during that time. You get them over that hump and then they’re getting to day 30. So we’ve found kind of these places to intervene, to maximize the number of people that get all the way through.

Nathan: [00:25:38]
Yeah, that’s interesting. So you’re talking about this web app. So people aren’t just posting their essays on Twitter, or maybe to their existing email list there they’re actually publishing them inside the application as well.

Dickie: [00:25:48]
No. So the application is just kind of a text box that allows, so we started with just a Figma template. And distributed to everyone, but you can imagine the user experience is not that easy to maneuver a Figma template. So shout out to the first two cohorts, who’ve kind of put up with that. And then we had a community member build this web app where you get full creative control, but with a much easier interface.

And then you export it right to an image you tweet right from there, but there’s no platform kind of for the images themselves yet, or thinking about something with it. But for now it’s just, just a standalone.

Nathan: [00:26:25]
Yeah. So how do you think about the, like the viral loops on this? I guess there’s two sides of it. One is for the individual creator, you know, of the audience of their building and all of that, but I’m, I’m work here is about for the product that you’re selling. Right. Of, The shift 30, it needs, you know, new, new creators to come in and participate in all of that.

And you haven’t really conveniently that all of your students, you know, all of your successful students are doing your marketing for you. How intentional was that? And then what changes or what tweaks have you made along the way?

Dickie: [00:27:04]
That was not as intentional as I would like to say that I had this thing, you know, big vision, but when it hit me that the more successful you are. The more marketing you do for the program, every successful one becomes kind of the front end asset for it. It was, I knew we were onto something when that clicked.

So I threw in, there was a little things like in the Figma template, if you want, you can put it your own URL, but if not, it just says Ship 30 to You know, we have the hashtag, we have people it’s a very ubiquitous thing, right. So there’s a lot of parts to, The branding of it, wherever it’s very recognizable and it’s working, right.

The audience that each member builds wants to then do it. So its kind of a, it’s a beautiful loop.

Nathan: [00:27:52]
Yeah. Are there other, products or courses or things like that that you’ve seen with a similarly successful, viral loop?

Dickie: [00:28:00]
I’m not sure to be honest. I think it’s. Because of the nature of it being like a writing challenge, in a sense you there’s a lot of other courses, you learn something and then apply it to something completely different. But this is a very specific thing of what your goal is, is to write. And so by nature of writing, you build in that, that viral loop.

Nathan: [00:28:24]
Yeah. And it’s just, it’s taking everything that would be spread out over a long period of time. Like someone might be thinking about, okay, I’m going to do a cohort based course. I’m going to, I’m going to charge a thousand or 2000 or $3,000 for it. It’s this big thing. It’s, it’s going to be six weeks or three months, like a semester long, you know, or.

All of this stuff. And then they’re going to implement what they learn over the next three, six, 12, 24 months. And that like, that’s interesting, but what you’ve done is you’ve just taken all of this and crammed it down into one thing with very clear deliverables. And so all of that momentum happens all at once and it’s fascinating to me.

Dickie: [00:29:07]
Yeah, and I think that’s why we’ve been able to grow relatively quickly. We started with 55 and the first cohort were 171. Then two 50 and now the current one is 335.

Nathan: [00:29:18]
Wow. Hmm. Okay. So, so those are some of the numbers get into the revenue side, right. how much have, have you earned from the business and, and what are you looking for going forward?

Dickie: [00:29:30]
So total we’ve, we’ve done some things with the pricing where in the beginning, In the January cohort, the price was $99 because we didn’t have the how to Ship 30 course. We didn’t have the email course. We didn’t have a lot of the things that we put in place now where we feel much stronger about charging.

So now Write the price. As of right now is 250. And so our average price for every single person who has come through is about 135, but that’s increasing now. And so the revenue breakdown. From just shift 30 is right around a hundred, a hundred thousand. And we have now Nicholas Cole and I have launched a follow on writing course called the right to Ship, which is for everyone who takes Ship 30 for 30, and really wants to double down in kind of an immersive online writing masterclass.

It’s the only way to describe a Nicholas Cole’s book, the art and business of online writing, which of course is based on his kind of head blowing emoji. Where he’s just been in this game for so long. and so he, he’s a primary teacher for that, and that has done about 45,000 between, so those are when the first quarter, and based on just our, our current trajectory where we’re looking to, I don’t have an exact projection, but we just start, it’s hard to forecast.

Right. We’re just moving quickly and continuing to improve all the products. And, and on that side, we’ll see what happens.

Nathan: [00:31:00]
Yeah. Yeah, that’s good. One thing. Right? So those are all the really positive, exciting, sides of it. one thing that I want to ask about it, especially because it involves, you know, our community directly, is some of the, like when you first came out with the sales page and everything for, shift 30 for 30, like the cost and similarities to Sean McCabe’s, 30 days to better writing.

And so I’m curious. One how that came to be. And then also, you know, how you handled a mistake like that. And then maybe the final thing is, is sort of this, this balance between, inspiration and us all being in the same community and learning from each other versus, you know, something like plagiarism, which is a big deal in the, in the writing community.

Dickie: [00:31:48]
Yeah, that that was a, drastic mistake on my side and caught up in. The idea I had was just market research on some are things. And I, to be honest was, it was just a terrifying moment for me when I realized what I’d done caught up in kind of a, a swipe file of notes and different things like that. And right when I kind of clicked two and three, it was, I need to own this mistake spot on.

And so I said, Sean, this was a massive mistake. I, I. Take full ownerShip of it. I apologize. And I took it. I mean, it would have been up there for no more than a minute or two, no lie. And I took a step back after that and said, I have some, this has grown faster than I thought and had some work to do. And so I tried to, you know, took a step back and said, how can I prevent anything like this?

I need to check myself and. That was a big moment of growth for me, where I kind of got shaken awake and I’m glad Sean was tremendously respectful and had every reason to be, you know, not as, as nice as he was about it until I’m very glad that we were able to, to kind of work that out.

Nathan: [00:33:06]
Yes, I’m in, Sean’s an incredible human I’ve known him for a long time. He actually lives here in Boise. He was over at my house like four days ago for dinner. and, and so I, he’s just so generous with his time and everything. And I think on the business side, there’s a lot of places that you can make missteps.

I’ve certainly had them with ConvertKit over the years with my own writing. And so, you know, one, I think it’s important to talk about them, too, like exactly like you did, I’ve just own up to it. There’s this other angle that people can take of like, Oh no, I didn’t like let’s pretend that happen or something.

And that is a sure way to take, you know, a small problem and turn it into a huge problem. cause the internet is very unforgiving of people who. Pretend that they didn’t make a mistake, you know? and so just like owning up to it directly and then sharing lessons learned from it. So, I love to hear that, you know, that was a point where you’re, you’re putting in more, safeguards or things like that.

Is there anything that you recommend for writers going through your course or how they should, you know, make sure to cite sources properly or, You know, bridge this gap between inspiration and, and, like w wild side of inspiration and what they’re actually publishing.

Dickie: [00:34:31]
I think it’s a, you hear it to imitate then innovate where the more you can, all of these ideas are remixes and you want the best way to do it is say where your you are inspired from. And so it it’s credit in the footnotes or whatever it is, but the more you can take ideas and then expand upon them, remix them, bring them together with others, is something we preach heavily.

Nathan: [00:34:55]
Yeah. Yeah, that’s a good one. It makes me think of there’s this idea of, you know, leverage selling products, multiple times, all of this that I’ve talked about for a long time, you know, I wrote a book about it and back in 2013, All this stuff. And then I came across Jack butcher, you know, in the last couple of years, phrasing it as build once, sell twice.

And that was just the, you know, the, all these concepts that he had just narrowed down into one really simple phrase. And it’s like, Oh man, one, I wish I thought about that. I thought of that because it’s such a good phrase. and then, you know, too, I want to use it in my work. And so it’s just like, okay, I.

As a writer. I absolutely can. I just have to immediately say like, well, I learned from Jack butcher. You just have to give that, that credit immediately. cause there again, there’s nothing new under the sun. It’s all been said one way or another and it’s just cite your sources.

Dickie: [00:35:54]
Yeah, spot on. It’s fine.

Nathan: [00:35:56]
Let’s dive into the Twitter growth side. Cause that that Twitter account that you spun up, you know, starting from scratch, is now over 20,000 subscribers. So things have, have taken off. what have you learned in going from zero to 20,000 and what are we at eight months now?

Dickie: [00:36:16]
Yeah, I think it’s a, it’s definitely a consistency side where I think I’ve tweeted. 35 times a week for the last call. It, however long since August, have written three or four threads a week and Twitter, it’s a fickle platform because you have to consistently create content and continue to put it out.

There is a way you can kind of put some Metta threads together and have, you know, ways of, of linking your old content. But at the same time, if someone visits your site or your profile, They get about four tweets or your bio to decide to follow you. So it’s a consistent kind of putting things out and also just having a clear value proposition either whether it’s in your bio or things like that, where the amount of optionality that anyone has to follow other people on Twitter, you kind of have to have a decent calling point.

So all those points you can put in place to make that easy is the name of the game.

Nathan: [00:37:17]
So were there, like in all the different types of. Tweets. And I’m wondering if you even break this down. All right. There are things where you’re or if I look at what’s working for me, sometimes I’m surprised by it. Like I asked a question of, Hey, what is genuinely asking? what has made for a great Airbnb that you’ve stayed in because I own a few Airbnbs, I’m looking to level up the experience, et cetera.

And that was like 350 replies and all this engagement and all of these followers. and I was like, I was just, you know, taking advantage of the fact that I have bunch of trends. That’s what our followers to get an answer to a question rather than, you know, looking for engagement. So I’m curious in all the different types of tweets that you could do, whether it’s threads questions, pithy, little perfect, you know, quotes like things that people will always agree with.

What stood out to you that has worked in those, or are you just always playing with every different style?

Dickie: [00:38:16]
I have a couple consistent ones that I do. So in February, I for I’ve been journaling every morning for two or three years now and have kind of a staple of questions. And so this was one of my old blog posts that I published kind of into the void of my 10 favorite journal questions, 10 favorite questions to reflect on and where I found them.

And I wrote up a thread on, on those, inspired by Tim Ferris. And in February he shared a link to my thread in his five bullet Friday. As a and so that was, for me, it was, I mean, I’ve listened to every episode. It was one of the coolest things to, you know, be just scrolling through and boom, get your name hit in the middle of it.

So one that accelerated kind of my growth, but at the same time I’d been tweeting some reflection questions. And so now every morning, Monday through Friday at 9:00 AM, you’ll get a question to reflect on. And it’s just an interesting question for me. And so I find that these consistent formats where. You kind of become a Chipola like consistency, where people come to your profile and they know what to expect on a lot of things.

Like I ask a question of the day on Mondays and Wednesdays of just, you know, what is financial freedom look like to you? 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. And it had 3000 replies.

Had just because it was, and it was just a classic example of these constraints, creating creativity. but now those, the ones that are just engaging, asking questions, obviously scale is you have an audience, but they’re the most fun task. And as a nature of the Twitter algorithm, when people respond to something, it shows up in more feeds, right?

So there’s that kind of, like you said, about the Airbnb, it was the reason so many people saw it was everyone else saw other people respond to it.

Nathan: [00:40:10]
As you look at that algorithm, are you seeing other things that are, you know, rewarded more? since Twitter does reward, you know, at first it was just retweets. You know, if you want to be seen in other feeds, it had to be retweeted and now favorites and replies are, are playing into it as well.

Dickie: [00:40:27]
Yeah, I think less so on that. What works? It’s the, what does it work or posting the links. And so if you try to take Twitter off, if. You can see it in the data of, if you try to post links to something, you’re it just gets crushed. I don’t, I understand why I don’t know how they kind of program it, but I’m sure it’s some algorithm to do so, but that is a reason to any kind of writing you do.

And you’re seeing it more is you have to repurpose everything for Twitter. And that’s what their goal is, is like they are taking flight in this creator ecosystem, right. They want you to stay on the platform, create content there. And so if you have a blog post and you’re not, you know, I think Mario who was on the last episode does a tremendous job breaking down every post of the generalist into a thread.

And that gets a lot of engagement naturally, because if he just said, Hey, here’s the breakdown, go click on it. One people don’t like to leave Twitter very much. And two the algorithm doesn’t like when you try to bring them off. Right? So it’s a double whammy that, if you’re repurposing, you’re going to get the best of everything.

Nathan: [00:41:31]
Yeah. And I mean, that’s something that we’ve seen with, YouTube quite a bit where YouTube does not like to drive traffic off of the algorithm or off of the platform and the algorithm, you know, you could say. It’s debatable, whether it penalizes videos that drive versus it rewards, videos that keep people on the platform.

Probably some combination of both, when we have these, this Content that, you know, so I wrote an article, probably the last, like really serious, essay I wrote was called the billion dollar creator. And I wrote that on my blog. It’s, you know, I don’t know, 3000, 4,000 words long or something. and. That Twitter thread that I wrote of taking the highlights all the way down, you know, turning it into a threat and making sure there’s images for each thing.

That’s probably the most popular tweet I’ve ever put out. but I’m curious when you’re thinking about taking long form writing and repurposing it for Twitter. When do you go to a thread? When do you go to, you know, an atomic essay or something put into, you know, a screenshot and. Is there a system there?

Dickie: [00:42:43]
There’s not that clean of a system, but my kind of mental hierarchy is everything starts as a tweet. And if it’s got a little bit engagement, I’ll explore it more for myself and posted it as an atomic essay. And then if that gets a lot of engagement, I know there’s people are more likely to share threads.

I think just because the, you know, I think it’s a little more natural of like a retweet versus retweeting, the image. so that’s kinda my. Sot. And I think on the long form side, it’s definitely a thread because it ties nicely in to most of your long form content. It’s going to be a lot of not standalone things, but sectioned off things.

Right. So you can repost each one is its own kind of standalone, all the way down.

Nathan: [00:43:28]
Yeah. That’s interesting. Somebody else I see is like, David Perell will often do this as he’ll go back to these old threads. or AIJ who created card? he’ll do, he has this thread, that’s probably like 500 tweets long at this point of like every update and improvement he’s ever made to card. How do you think of that as opposed to new Content

Dickie: [00:43:48]
Yeah, that, one’s a little bit of inside baseball, where if you, if you have a tweet thread and you respond to it later, it shows the top tweet and the most two recent replies. So I just wrote a thread in my most popular one, ever. And it was just 10 inside Twitter, like advanced Twitter tips. And that one blew up beyond my wildest dreams had 40,000 likes or something like that.

And one of the tips was if you want to re, re bring Content back up to the top, just respond to it. And don’t retweet it, like add a new layer of thinking to it or something like that. And it naturally just brings it back up to the top as if you just tweeted it.

Nathan: [00:44:31]
And so then people are seeing this, this tweet that’s already, popular. It’s already maybe got 300 likes and twenty-five retweets and they’re like, Oh, this must be good. And they’re not paying attention to the fact that it’s, you know, six months old or six weeks old,

Dickie: [00:44:48]
Correct. Yeah, exactly.

Nathan: [00:44:50]
What are some of, of those other things? And then we’ll obviously point people in the show notes to the thread about Twitter threads. If we can get more meta than that.

Dickie: [00:44:57]
Okay. The first one of the big thread was just advanced Twitter tips and it was things like how to create lists, how to block, meet words. So that one is a little less prevalent, but I wrote one breaking down. Why I thought that one was successful. And that is kind of my approach to thread writing.

And so a couple of just small ones, his eye of the camp that every tweet should act as a standalone. So I don’t number things because you’re able to engage and pop in and reply to single ones on your own. I think there should be. 90% of your thread success is going to be the very first tweet. And it’s just a exercise in copywriting.

And we’ve seen all the trends of, you know, time for thread or capitalized thread, those come and go. And once people get sick of reading them, there’s a new one that comes out that kind of captures people. So that one is something we’re spending more time on than cause at the end of the day, like that’s the click-through rate, the better that you can get people to.

You’re just clicking on an article in the same sense. Right? So however you can. Write your copy too, to bring that up. and then just, if you break down the virality of it, it’s people share things that are educational or entertaining. And so you should very clearly see which one, like Sean periods, clubhouse thread, that’s the funniest, one of the funniest things I’ve ever read.

And there was just, no, it was as long, it was the longest thing I’ve ever read on Twitter, but there was no way I was, wasn’t going to go back up to the top and share it. And speaking of which, I guess one last tip is after you post one, you can quote, tweet it at the very bottom to give someone kind of a call to action, to jump back up to the top, to share it.

So it’s, Hey, if you enjoyed this. You know, jumped back up to the top and, and share it with your, with your followers and then they can tap right on it. And it brings it back up because so often you get to the bottom and it’s just, you just swipe away. It’s, you know, I’m onto the next thing, but this is, this is a way to say, Hey, if you enjoyed this, you probably forgot that this started up at the top here.

They can click on it right away and share it. So it’s just, you know, empathetic writing, getting them to do a little bit less work to go up and, and share it.

Nathan: [00:47:01]
Yeah. And that works well for you. And so one thing that you could do is if you had some popular threads in the past, you could even put that tweet at the very end referencing, you know, doing the circular reference and that, you know, would work well to, make the thread more effective going forward.

And as you were saying, it would resurface the thread almost like a retweet would.

Dickie: [00:47:23]
Yeah. There’s like a, there’s a. Ecosystem of content you can start to create. Once you have a bunch of threads on a bunch of different topics, it’s like, Oh, I’ve already covered this here. If you want to learn more about it. So, and it it’s a, like a Roam Research of, of Twitter, which they don’t do a great job of, of working out.

But there’s like a way to link all your content together in a way that’s almost immersive. Right? You can just jump around and stay down the rabbit hole.

Nathan: [00:47:48]
have you noticed something like on threads? You’ll see people, you know, do take Mario for example, with it,

you know, club, he’s writing all of that up. And then at the end, he’s usually linking to like, go read the full piece. Ha when that’s buried a little further down in the thread, do you think Twitter penalizes that?

or do you think that works fine to link people off if it’s at the end, right? Yeah.

Dickie: [00:48:14]
I think that works fine. I think it’s on the tweet level that you will, are penalized for a link. So it’s not that they like sense that you’re trying to do it at the bottom. I think it’s, if it’s like a simple statement of, if this contains a link like penalize share-ability.

Nathan: [00:48:30]
How that’s fascinating. What about media? Like, I think about a thread, from Andrew Wilkinson that he did on, it was like the. The real story about private equity firms and being bought. So it was like a mix of his, his experience plus general experience and all that. And his media all the way through was

mostly like Scrooge McDuck, you know, gifts like diving into gold coins.

And like, it wasn’t that relevant, but it didn’t make it a lot more engaging. And so I’m curious, does obviously the image to get people to click in and pay attention, but he had an image tied to every single one.

Dickie: [00:49:11]
Yeah, I have. I’ve noticed that I have, more pure text, mostly because I’m not creative enough to like figure out an image for every single one. But. Some like Sahil, Blum who writes tremendous threads on, on finance does a lot of images and everyone just to kind of give it some context and some texture, I think it is.

And I’m sure it works for, for everyone. Right. But, it’s not something I’ve particularly explored, but I think it’s, I enjoy reading them when they’ve got some kind of image or a little video clip here and there. or gift that, that keeps the reader going.

Nathan: [00:49:43]
Somebody else that I want to touch back on is you mentioned you don’t number threads, or like, you know, this is tweet four of seven, which is something that always annoys me for whatever reason. when people number the threads, I feel like, I don’t know. It makes it feel like non-native Content.

Like it doesn’t actually belong on Twitter. it, and like you were saying, each tweet can’t stand alone and often you’ll find that where you’ll click you’re seasoned and retweeted you back. Oh, that’s interesting. You click into it to see the replies, and then you realize that it’s actually tweet five of a 25 tweet thread.

It’s not even the beginning of it. for some reason, it just seems less engaging when you’re putting something in there that is not necessary for the tweet itself. So I think that’s a really good point.

Dickie: [00:50:34]
Yeah, like the one flash, it just, it, it doesn’t do much, you know, it, it takes away from the flow of it. Right. That’s how I feel.

Nathan: [00:50:41]
Yeah, that’s good. Keep bringing it back to newsletters. so Twitter, these days is one of the biggest channels that people are growing newsletters. how has your efforts on Twitter? How has that played back for your newsletter? And what’s worked to drive, subscribers or followers from Twitter to newsletter subscribers.

Dickie: [00:50:59]
I haven’t done. So my newsletter is it’s just a curation of links that I’m interested in, on. I just really call it growth. So growth of companies, people, systems improvement, that kind of thing. I have had really three events. I think I have like 2,900, 3000 subscribers on my newsletter. because I’ve kind of focused more on Twitter.

I feel like I could start to share my news that or more to drive traffic, but the three that had one of my very first successful threads, I wrote one on biology’s tryna Boston, that Naval picked up and I went from 300 to a thousand Twitter followers. And. From 250 to 800 newsletter subscribers, just cause I popped it at the bottom.

And that was, I like to say it took 40 weeks to get to, to 300 in about nine hours to go to to 800, which is just how it goes. Right. but I have, my newsletter has turned more into just kind of a personal thing and the, the growth of it, I’m less focused on because there’s not. Everyone has enough curation his letters.

I’m really writing it for me at this point. Will I take it to a different medium or something in the future, maybe, but, today it’s really just, you know, I’ll tweet it out and pop the link at the bottom. every, every Sunday when I write it, but nothing too, too crazy.

Nathan: [00:52:25]
Yeah. That makes sense. Is there anything that, as someone let’s say they’ve got 10,000 subscribers or 5,000 subscribers, they’ve got some traction. Is there anything that you would want to leave them with of things that have worked really well for you that you think other creators listening should, should take into account?

Dickie: [00:52:42]
Yeah, one of my biggest lessons learned on the content side was from Sahil, who I mentioned earlier and it’s create great content, but don’t underestimate the importance of distribution and for a lot of us Twitter, especially if, or whether it’s your newsletter. You want to feel confident in sharing the things you’re writing, right?

So it’s almost this forcing function where if I say every thread that I write, I’m going to DM it to 10 people who I think will find it valuable. I know that I’m going to put more effort and more refining into my content, but at the same time, that’s going to force me to create better content. They’re going to be more likely to share it.

And so I’ve fallen into this trap of, “Oh, I’ve, I’ve hit that 10,000 Mark enough people are reading.” You never know, they could be on an off day. And so hustle for distribution and take it seriously, I think is the biggest lesson that I’ve learned and the result is better content and just more growth.

Nathan: [00:53:46]
Yeah, that’s great. Well, where should people go to follow you on Twitter? Subscribe to the newsletter, check out the course and everything else?

Dickie: [00:53:53]
Sure. So on Twitter, I spend way too much time. That’s @Dickiebush, D I C K I E B U S H. I’m sure you’ll find me there. If you want to learn more about Ship 30 for 30,, and my newsletter is So I keep it simple. And yeah, the DMs are open. Reach out.

I love to chat, and you’ll definitely find me on Twitter that’s for sure.

Nathan: [00:54:21]
I think what we’ve established for sure is that you’re very accessible on Twitter. Well, good times. Thanks for coming on and we’ll chat soon.

Dickie: [00:54:31]
Cool. Thanks Nathan. I appreciate it.

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