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9.6.21   6:06 PM

An armada of tiny ship icons is quietly amassing on Twitter. Showing up in bios, the little boat pictures signal an influx of personal essays appearing in people’s timelines, covering wide-ranging topics like work, life lessons, family and pets.

The culprit for this invasion is Dickie Bush. A 25-year-old portfolio manager, Bush decided during the pandemic he wanted to establish a daily writing habit. He set a goal of writing one short piece every day for a month, and found other people on Twitter who wanted to do the same. He was so pleased with the results that he turned his project into an online writing course. 

Now there are at least 1,200 new writers who have been unleashed on the internet by Bush (each paying about $350 for the course). His program, called Ship 30 for 30 (referencing the word “ship” as a synonym for publishing), challenges participants to post 30 micro-essays, of 250 words each, on Twitter in 30 days. The package includes training sessions taught with help from his friend Nicolas Cole, an author and online media entrepreneur who got his start by becoming a top writer on Quora.

Along with helping newbie writers get more comfortable putting their thoughts out for the world to consume, the program promotes an ethos: Legacy media and gatekeepers are out; engagement-driven content and self-made creators are in.  

“What the internet enables you is to get rapid fire feedback on potential ideas,” Bush explained. “So you don't have to wait for this giant epiphany, you can test a lot of small things, and then double down on what's working.”

Although I’ve been writing professionally as a journalist for about 16 years, I decided to try out Bush’s course. The experience was refreshing. It was especially enjoyable to connect with other “shippers,” who were enthusiastic about practicing their craft, and dedicated to giving each other feedback. This is a far cry from the cynicism you often find in traditional publishing, where the norm is getting ignored by overworked editors perched on ivory towers.

We caught up with Bush (between his busy day job and his very absorbing side gig) and he told us more about why he started Ship 30 for 30, and where he sees his fleet of online writers heading.

This interview has been edited for length and clarity.

  • Finding a community through a personal writing challenge


    Business of Business: So Dickie, you have an interesting resume. You work as an investment professional, but you also run an online writing course, where you help people be better writers on the internet. How did you get started doing that?

    DB: It goes all the way back to the start of 2020. I'd been reading all these books, and listening to podcasts and all these things,  and kind of thought, "I have all this information. It's not going anywhere. It's kind of just being stored in the back of a notebook somewhere." And I wanted to start sharing it. So I started a newsletter that basically summarized all the podcasts and books and whatever articles I'd read that week. And so that was the beginning of 2020. I'm still doing it today, and I found just the number of opportunities and friendships and just fun I had doing it was something I wanted to help other people do as well. And so there's a bunch of different steps that got to where we are now. But it was really just the positive experience I had, and getting other people to do that.

    How big is this now? Like, what are the metrics you can give me?

    So we have about 1,200 students who have taken Ship 30 for 30 in the past. That blew my expectations away for sure. What's cool about it is it scales pretty well in terms of how many people could do it. And I think 1,000 or 10,000, could do it at once, really, because it's a 30-day writing challenge at the end of the day. Now there's kind of more to it. But yeah, it's it's definitely been faster growth than I ever thought. It's pretty cool to look back on it as we kind of lap the one-year point soon.

    Can you explain that 30-day writing challenge? How did that come together?

    The original thing for it was I wanted to start writing every day. I've been publishing a weekly newsletter for a while. And I wanted to start doing it every day. So I tried and I went about seven days on my own trying to do it. And then I realized that there was no way I was going to be able to stick to that on my own. So I went on Twitter and just said, "Hey, is there anyone who wants to do this with me?" To kind of have some public accountability. And it was overwhelming, the response — the number of people who are like, "Yes, I've been I've been looking to do this forever."

    So it kind of emerged organically out of solving my own problem. And then the the 30-day part was just long enough to form a habit, do it consistently. I feel pretty good about how we went about just building the habit. The results kind of spoke for themselves. You work through so many ideas during that time that you get a lot of clarity for things you're interested in. There are things you maybe assume you're interested in, but are really aren't..after six days, you just kind of run out of things to write about [on that topic]. So it's a pretty cool kind of personal exercise on top of getting to meet a bunch of other friends and have fun doing it, too.

  • Learning how creativity thrives with constraints


    I am actually taking this course right now  to kind of experience it. You're having people write these short 250-word essays each day. What went into setting those types of parameters?

    One of our core concepts is that creativity thrives with constraints. Writing every day is very difficult. But writing every day, a 250-word essay, in an hour or less is a lot easier and more manageable. I think one of the biggest things that holds people back from writing online is how many choices they have to make. What platform do I use? How long should it be? When should I post?  We've tried to just give them this playground with very tight rules and say, "Now go focus on the writing," which you can do if your mind wasn't occupied making all these other decisions.

    What we find is that the constraint unlocks so much creativity, because [writers] don't have to think about all that. They just sit down and it's like, "Oh, I could operate right in here." And so that emerged really just from what I thought was manageable for myself on a 30-day basis. That has stuck really for the last eight months.

    It looks like a lot of the target audience are aspiring business writers or maybe self-help. Is that a good characterization? Or what other types of writing have you seen?

    It's really wide. I wish I could show you the chart, but the number of topics is everything from fiction, to self improvement, business, everything. And outside of that, the number of perspectives, we have every single time zone represented, which to me is the coolest part of doing anything on the internet is how global it is. Right? You have. So I'm posting a call at 6pm. Eastern, and I'm realizing that it's 2am in all these other countries, and it's actually kind of the harder part to manage. But, yeah, it's just such a rich, diverse group, which is been the coolest part of doing it.

  • Why online writing has different rules than legacy publishing


    That's amazing. Have there been any content creation or writing careers launched by this?

    We're right at that inflection point now, where we've had people who have done it multiple times, who are launching their own products and businesses and really starting to accelerate them. In one or two years, it's going to be pretty cool to look back and say, "Wow, look at all these people who have audiences and their own business. And they started with Ship 30." So it's kind of like an angel investment in a lot of these writers in a way. They're going to be able to tell other people in the future,  'This is where you should get started, because this is how I did it." 

    I've noticed that you guys do have a lot of good tips in your sessions. There's also some kind of philosophical...attacking isn't the right word, but talking about legacy writing, and and kind of explaining it as the past, whereas content creation, the way you do it, is the future. Can you talk about that a little bit? 

    It's really just understanding that writing on the internet has a completely different set of rules than what people are used to. I think the way it's taught in schools is still so much in that old legacy way that you have to have an idea, and then you retreat into the woods for 18 months, hopefully, with no internet, and then emerge with this masterpiece. But now, the internet enables you to get rapid fire feedback on potential ideas to write about. So you don't have to wait for this giant epiphany, you can test a lot of small things, and then double down on what's working.

    So it's kind of a data-driven approach. I go out and think I want to write about 10 different things, I'm going to go write small, make small bets on all of them, see what happens, and then double down on the ones that you know, resonate. It's just a different approach. I think there's more tactical stuff of recognizing that when you're reading something on the internet, you're not competing with other writers, you're competing with Netflix and TikTok. So you have to keep attention, you have to be concise, you have to use headlines.

  • Tapping the power of thousands of aspiring writers


    That's very cool. Who else runs Ship 30 for 30 with you? 

    So I have a partner, Nicolas Cole. He's just a master of online writing, and doing a lot of the things we preach. He's been writing online since 2014. He's like a top writer on Quora, Medium, everywhere. He  understands this game better than anyone else. The live sessions are co-hosted by us, and we're partners in the business. It's kind of a mix of my habit-building and understanding that I solved this problem for myself a year ago, and then with him, it's "here's everything from my 10 years of knowledge in a four or five-week course. So it's a nice little partnership." 

    I've also noticed an interesting aspect of the program is you get a supportive audience — people who want to, you know, look at your stuff, see what you're doing. And that is nice on the internet, because we see so much negativity on the internet. Was that an intended part of the program? Or did that just evolve organically?

    One of the things we hear all the time is "I came for the writing, but stayed for the community." And it's true, because writing online can be a lonely endeavor — especially if you're publishing on your own blog, and you've hit publish, and it just you hear the crickets of indifference from the internet, right? But what Ship 30 does is enables you with that feedback from other people, and you get to make friendships along the way. It just creates a more immersive, rich, rewarding experience versus "I'm slaving away over a hot keyboard to publish a blog post that no one ends up reading, and then I'm frustrated and I quit." 

    Yeah, that's cool. And you have you have a pretty good Twitter following now? How many followers do you have now compared to before you started Ship 30 for 30? 

    The original idea for it was in November of last year, and I had a little over 1,000 followers....[Now] I think I just hit 56,000, maybe 57,000. 

    How much do you think this will grow? And where do you want to take this? 

    I don't know. It's been really fun to do. The last seven months have been such a blur...we haven't taken off more than two weeks off between a cohort yet. So it's like I get that extra week to think. And, look, I think a million people can take Ship 30, right?  The number of people who should be writing online is massive. There's so much knowledge out there. And so if it got to a million people, how cool would that be? But I don't know how big it could get. I'm having a blast doing it. So I'm not in any rush to scale or I'm really just kind of letting things grow organically and have fun along the way. 

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