035: Dickie Bush - How To Make $100,000 Writing on Twitter

05/10/21 • 54 min

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 th...

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 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

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

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

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 th...

Previous Episode

034: Jason Feifer - How To Balance Creativity With Your Career

Jason Feifer is the Editor in Chief at Entrepreneur, an American magazine and website that carries news stories about entrepreneurship, small business management, and business.

He also hosts a podcast called Build for Tomorrow, and he is the author of a forthcoming book titled Build for Tomorrow, Not for Yesterday.

Jason is a unique blend of individual creator and polished corporate employee, so he offers a balanced perspective on work and content creation. In this episode, Jason and Nathan discuss:

How to package your work
How to pitch your content and get press as a creator
Time management for creators balancing full time careers

Links & Resources

Jason Feifer’s Links

Personal site: jasonfeifer.com
Jason’s Podcast: Build for Tomorrow
Jason’s forthcoming book: Build for Tomorrow, Not for Yesterday
Jason’s Instagram: heyfeifer
Jason’s Twitter: @heyfeifer

Episode Transcript

Jason: [00:00:00]
You make the thing that you want to make. You believe in it, and you don’t give up on it, and you spend years doing it. And if you’re good at it, and if you were right that this was a thing that was worth making, people will find it because good really does rise up. It happens slowly, but it does happen.

Keep going.

Nathan: [00:00:23]
In this episode, I talked to Jason Feifer. Jason’s the Editor in Chief of Entrepreneur. And we dive into a bunch of different things.

One, how he splits his time as an individual creator and, you know, running a very successful, very popular magazine. How he blends those things. He’s got a newsletter, he’s got a podcast, he has several podcasts. He’s working on a book, all of those things. So how he prioritizes his time. All of that.

The monthly cadence that he works on, I found really interesting. We also dive into how to package your work. We talk about why he changed the name of his podcast and the research that went into that. Then finally we wrap up by talking about PR and how to get press as a creator, how to think about pitching each individual publication, the work that you need to do to actually get covered a lot of good stuff.

So let’s dive in.

Jason, welcome to the show.

Jason: [00:01:15]
Thank you for having me.

Nathan: [00:01:16]
So I want to dive in, you’ve got two very different things going on. They’re actually, I mean, they’re closely related, but, two different worlds, you know, with everything you’re building on your own audience. And then of course, as Editor in Chief of Entrepreneur, I’m curious just how you spend your time, as I would think the Editor in Chief is a very time-consuming thing. Then you’re building an audience. You’ve got two young kids, you know, you’ve been doing it all through a pandemic. And so I’m curious what, you know, what a day or a week looks like, in Jason’s life.

Jason: [00:01:51]
it looks like panic. It looks like absolute mass panic. That’s how I feel. Panicked. Okay? So first I’ve made this, I made this realization a couple, more than a year ago. I can’t remember when this took place for me, but I realized that I needed to maximize how my brain works, like work with my brain.

Right. Which is to say, when am I best at doing various things? And then let’s make sure that I’m doing those things at that time, because if I can write a full, like 2000 word story, in, let’s just say two hours, which sometimes I can do, that’s going to happen in the morning. If I try to do that at 5:00 PM, it’s going to take four to six hours.

So why on earth would I waste my time doing tasks when I’m not primed for them? So I clear out the for if I ca...

Next Episode

036: Ann Handley - How Expert Marketers Get More Subscribers

Ann Handley is the founder and Chief Content Officer for MarketingProfs, a marketing and training education company with more than 600,000 subscribers. She is a well-known public speaker, and has been writing a newsletter called Total Annarchy for the last three years.

Ann is also a Wall Street Journal best-selling author of Everybody Writes: Your Go-To Guide to Creating Ridiculously Good Content, and Content Rules: How to Create Killer Blogs, Podcasts, Videos, Ebooks, Webinars (and More) That Engage Customers and Ignite Your Business.

Ann was named a top thought leader by Forbes and one of the seven people shaping modern marketing by IBM.

In this episode, Nathan and Ann discuss:
- Tiny-house offices
- How to connect with your audience and grow your email newsletter
- How to grow your social media following by mastering the algorithms

Links & Resources

Ann Handley’s Links

MarketingProfs
Personal site: annhandley.com
Ann’s Newsletter: Total Annarchy
Twitter: @annhandley

Episode Transcript

Ann: [00:00:00]
The notion of voice is essentially how you sound. It’s important to read things out loud. It’s a thousand little choices that you make all along the way that over time, grow your voice and add up to something that’s wholly unique. Find those small moments. Those small moments are the things that become a big differentiation for yourself.

Nathan: [00:00:27]
In this episode, I talked to Ann Handley. Ann is the Chief Content Officer for MarketingProfs. She’s been around the content marketing online business space for a long time, since 1999. She’s been writing a newsletter for the last three years on a lot of really interesting things. She’s also a really well-known public speaker.

So in this episode, we talk about a whole range of things like what she thinks of the multiple rises of email newsletters over the years. The trend email is dead. The balance between email and social media platforms. We get into algorithms. We talk about really a whole range of things. Probably my favorite is when we get into talking about style and voice and how you write, how to make things fun. Her newsletter is called Total Annarchy.

Annarchy, it’s spelled like her name. And so you can see if that gives you an idea of the way she likes to write, the energy and passion that she brings to a business and marketing topics. So, anyway, with that, I’ll get out of the way and let’s dive into the show.

Ann thanks for joining me.

Ann: [00:01:28]
I am delighted to be here. Thank you for having me.

Nathan: [00:01:30]
So I want to start with something that has nothing to do with email newsletters, and it is just a shared love that you and I both have that I discovered in research and that is for tiny house offices.

Ann: [00:01:41]
Oh, really?

Nathan: [00:01:43]
Yeah, so I’m in my tiny house office that I built a year ago. I got it finished just before COVID which was good timing. If I understand correctly, you had a tiny house office built, like six or seven years ago.

Ann: [00:01:55]
Yeah, this is it. Yes. I was, it was, turned out to be a prescient move because who knew? This is very, so I’m in my tiny house office right now. It’s in my backyard. and yes, I built it, oh, six or sevenish years ago, something like that. And I built it at the time as a sort of place where I thought I can come and do my best work.

It’s, you know, small enough that it’s just me in here, me and my, and my little dog who’s here with me now. Little tiny porch on the front and a hard wire internet connection. And that’s it. So I built it as a place to really, as I said, do my best work as a place to write, essentially that was just sequestered from everybody else that, that I couldn’t hear anybody breathe back here. It was just, you know, a hundred percent perfect. And then, you know, fast forward COVID happens. And suddenly my tiny house is now thrust onto the international stage. It’s, you know, now the backdrop for all of these online programs that I’m doing, which is fine.

Just that I kind of had to clean things up a little bit. So, so ...