Dickie Bush — Harness the Power of Digital Writing

Modern writing is very different from sitting in a reclusive cabin in the woods secretly toiling away for years to write the next bestseller. Modern writers write in public, in front of and with their eager readers. My guest today, Dickie Bush, has helped thousands of people start writing online. And he does this with such kindness and a love for teaching that I just had to talk to him about all things writing. We'll dive into Ship 30 for 30, building a media business, and why his mom has been such a wonderful and pivotal figure on his professional journey. This episode is sponsored by acquire.com. More on that later. Now here is Dickie. Hey Dickie, thanks so much for being on the show today. You've taken one of the most solitary acts, that's writing, and you've turned it into a team sport with Ship 3430. Where did that idea come from?

Man, so we're right on the 3-year anniversary. We're coming up probably a week away from the original tweet that started the entire Ship 30 for 30 journey. So excited to dig into that. But first, just want to thank you for having me. I was sharing before this that I think that your positivity and energy that you bring to the X Twitter timeline is something that the world needs a lot more of. So I just wanted to make sure that we shared that because I've been listening to this podcast. You hear your voice and just the way you bring founders on and talk to them, and it's so positive sum what you do across the board. So just wanted to make a point on that before we dive into— the stuff that we're going to talk about today.

Thank you.

Okay. So anyway, on the Ship 30 side, we're about 3 years since that original tweet where, backing up before Ship 30 started, I was working a full-time job on Wall Street as a hedge fund trader, graduated college, immediately started working. It's the only full-time job I ever had. I quickly saw the writing on the wall about 9 months into that job that I did not want to be commuting to the subway at 6:00 AM, sitting under fluorescent lights for 14 hours a day, leaving when the sun was down and repeating that every day and hoping that one day I maybe made enough money to be happy. I saw that writing on the wall and said, okay, I'm not going to quit immediately. I'm going to start writing on the internet. This was January of 2020. And for the first 9 months, I followed that conventional path that I think a lot of people fall into when they start writing, which is start a blog, write on that blog, hope that readers find you someday. If your writing's good enough, people will find you, et cetera, et cetera. And 9 months in, I had 150 newsletter subscribers, maybe 200 Twitter followers, and was like, this is not what I was hoping. I'm still working this corporate job. I have no potential new opportunity because of this. So I was ready to give up entirely on it. But rather than stop, I said, I'm going to give this one more shot. But instead of writing on a blog, I'm going to write a daily Twitter thread every single day for 30 days. And instead of publishing like on a blog, I'm going to put it out in social where other people might be able to find it. I wrote for 27 days, and on the 28th day, I hit publish on a Twitter thread that got zero likes, zero comments, and zero retweets. So I said, well, here I am back stuck again at square one. Looks like this challenge failed, and I'm probably done with this writing on the internet thing. I'm gonna go explore some other opportunities. But I wasn't one to quit. So day 29, I ended up hitting publish on something that I didn't think was gonna go anywhere, only for the sake of getting to my last 30 days. Hit publish, turned my computer off, went to bed, woke up the next day, it went viral. Naval had retweeted it, Balaji had retweeted it, a bunch of people that I really looked up to. Had 4,000 or 5,000 likes. I went from 200 followers to 1,000 overnight. I like to say it took 9 months to get to 200 followers and 12 hours to get to 1,000. And everything compounded from there. So I tell that full story because you mentioned that it was a very solitude, solitude Activity, writing. And that exactly is how I felt on that 30-day challenge. It was very lonely. I'd started to meet some other people, but realized, okay, if I want to continue doing this, I'm going to need a community of accountability and support to keep me going. So I tweeted out after that 30-day challenge and said, who would be interested in an accountability group where everyone writes and publishes an atomic essay every day for 30 days? And I retweet that tweet all the time. I comment about it because it's all chronicled on the timeline of when it started. And that was the original vision for it was just getting people together because riding online typically is pretty boring and lonely if you don't have other people doing it with you. So that was the origin. And the last 3 years has been kind of a wild journey of trying to get as many people as possible to recognize all the upside that I unlocked from my personal 30-day journey and getting them to experience the same thing.

Yeah. Oh, I bet that, that must've, that must've been quite the, Quite the day when you got that viral moment and that kickstarted all of this community building and teaching that you've been doing until now. That is so cool. I was there too. I was there watching it. I remember this. I remember like the early days and when Ship 30 happened, I was like, what's going on here? Like, somebody is actually trying to turn this into something that is not just for him, but for others, right? Teaching others. I do wonder like, how did the first cohort when you started out, when you just experimented, how does it differ to what you're doing now?

Oh, it's night and day different. So the very first one, it's so fun because so much of the story comes from that first cohort where I tweeted out this Typeform and said, who'd be interested? And I had like 300 or 400 responses to that. And I was only, I only had a couple hundred Twitter followers at the time. So I'm like, oh my goodness. Yeah, because like other people picked up on it and there was clearly a need here. So rather than let everyone in, I said, okay, we need some kind of buffer in some way. to make a little bit of accountability. But at the time, I had never made a single dollar writing on the internet. I was terrified to charge anything because I didn't think I had any kind of credibility. So to create that little bit of friction, I said, okay, to join, it's $50. And I'll give you your money back if you write every day for 30 days. So everyone who came in put $50 into a PayPal pot. And I said, I'll donate the rest, whatever we end up, because I was like, so terrified to charge money for this thing.

Right.

And I'm like managing a spreadsheet during the cohort, like who's written every day. And people at the end are like, I wrote every day, can I have my money back? And all this, and I'm managing it. And really that original cohort was just an accountability group. I didn't have any credibility to teach writing. I did one thing well, I could build a daily writing habit. And all I did was prove that I had done that for the 30 days prior. Yeah. Now, how things are different now is after that cohort, which was November of 2020, I met Nicholas Cole. And he had written at the time, The Art and Business of Online Writing. And I was still working for BlackRock. I partnered with him in January of 2021 to basically take his education and his way much richer, denser experience writing on the internet than I had, package it into a 30-day curriculum, and then deliver that as part of Ship 30. So the last 3 years has been, it's a community-powered course is how we say it, cohort-based course, community-powered course. Where we teach the fundamentals of digital writing based on his book. And you have the accountability of hundreds of other people who actually are writing with you, and you have the structured output goal of writing every single day. So the original cohort was us spamming essays in a Slack channel with no structure, and it was $50 and you got your money back. And today it's, you know, 500 to 1,000 people join every single cohort. We've helped almost 10,000 people start since then. So it's been quite a journey since that original managing of a spreadsheet journey.

That is so cool. It's an amazing story, obviously, like as a narrative of how something that just started out with you figuring out, oh yeah, there might be some people out there. And then it turned into this community-driven thing, which I love. It's such a nice thing. As a writer myself, like I feel like the best feedback comes just from writing and getting people reading it and telling you what they think. And if that happens in an organized structure, which a community is and a cohort is, that just makes you so much less afraid to write.

Yeah. Right? Like, I wonder what are the common things, or maybe not even the common things, what are the uncommon things that keep people from writing? Because accountability happens when you already start writing, right? But what keeps people from writing to begin with?

One of the beautiful things of Ship 30 is you, and it goes with the name of this podcast, we kind of bootstrap your initial audience where you have other people in the community, not necessarily that are going to be that interested in your writing, but you're going to find 1 or 2 or 3 people who do really want to read whatever it is you're writing about. And that people overestimate how many people they need to read their writing to go and iterate and improve on it. Where in the beginning, one of the things that holds them back is they think they need this massive audience if they're going to do anything. So they say, you know, I have all these great ideas, but I'm actually not going to publish them until I have more followers because then I'll unveil my good stuff. And what happens is they, they don't write any of their good stuff, which means the handful of people that do see what they have to say aren't impressed. So they never get to start spinning that feedback loop where instead we say, look, you only need 2 or 3 people because imagine you were in a coffee shop and you started to read your writing aloud and 2 people next to you were like, hey, I'm really interested in this. Could you tell me more? And you go, no, no, no, I don't want to hear your opinion. I need like thousands of people if I'm going to go publish any of this. It's like, no, you would just have that conversation with those 1 or 2 people and you'd be over the moon excited that they had anything, that they were interested in any way in what you had to say. And that's kind of what we emphasize with writing is you don't need a big audience to start. You just need 1 or 2 people who are going to say, hey, could you talk a little bit more about that? And then you talk about that thing the next day. And then they read that and you talk about their next questions and next questions. And before you know it, the scale of the internet guarantees that if 1 or 2 people are interested in your writing, the algorithms are going to work overtime to take what you have to say and show it to as many of those people as possible. And so that's what you get to tap into.

Oh, that's a very interesting observation. Like the seed audience doesn't need to be massive. It's kind of— I hope that's still true in a couple months on Twitter, because the algorithm seems to be a bit problematic in terms of discovery for many things, right? Is

that something that should impact your writing, like writing for discoverability, not just by people, but also by the algorithms that amplify our things that we have to say?

Well, yes, because the algorithms aren't going anywhere, which means you do have to figure out how to put things in a packaged way that the reader is interested in. Where people go wrong with algorithms is they blame them for something. It's like, oh, the algorithm is blank. The algorithm is the same for everyone, which means every— and I kind of internalize this idea as one of my core beliefs, but anything that every circumstance I come across is an opportunity, which means if the algorithm's the same for everyone else, I'm going to look at it and say, well, what's working about it? That doesn't necessarily mean you become a slave to the algorithm where you only end up publishing like Google Chrome hacks that go viral. But you do have to understand that we live in an algorithmic feed age, which means there's far less, and this is something we've been learning, right? So a lot of people might end up in my situation with a couple hundred thousand Twitter followers and say, oh, I've done all this work and now the algorithm's changed and I'm screwed. And I'm going to go complain about it. Whereas I said, oh great, I've been writing for the last 3 years and it sounds like and feels like my interpretation of the algorithm change is that Your level of followers matters far less than it ever has. And they're following more of a TikTok-style algorithm where you never know where your writing is going to go, which means every single piece of writing has far more upside than it ever has because you never, you don't know what's going to happen to it. What's the solution there? Publish more pieces of writing to unlock that upside. Yeah. So I went on a podcast like 2 months ago and someone said, how are you reacting to this algorithm change? I'm like, I'm just going to post way more. Right. Like, that's the solution because what is that going to do? It's going to give me more data. It's going to give me more information on what's working. And I've had more success over the last couple months on Twitter because of that. Whereas other people I heard complaining and they're like, oh, you can't do XYZ. It's nope. That's an advantage for me. I'm going to go publish more and I'm going to figure out what's working because of that.

Yeah. And that's, that's the big difference, right? Like figuring out how new things work in a new way. Like you need to kind of fall on your face a couple of times. And I think you have this, this concept of micro failures. That's what you call it, right? The idea. Well, Do explain it. I guess that this is probably a good opportunity to just introduce that idea, right?

I love Twitter as an idea refinery, which means the second I come up with something that I might find interesting or I want to explore more, I put it in a note. And every Sunday for the last 3 years, I've sat down and cleared that note into individual tweets. It's like my favorite part of the week because I end up with 8 or 9 ideas. Like, I'll re-listen to our podcast interview and pick up on 1 or 2 things that you say that I want to go deeper on. And I've been testing ideas for the last 3 years on my Twitter account. Some of those have gone viral. Some of those were not my best writing and they went nowhere. And because of that, I now have pretty good idea of what people are interested in, what I like to talk about. All the while, all these proven data points from my old writing are compounding for me that I can then repurpose. But then I also have all the new ideas that I'm putting out that Hey, I didn't know that if I talked about this topic, people are actually really interested. Cool. I'll go double down on it. So rather than 500 years ago, if you were, I don't know how long ago, but if you wanted to publish a book, you had to go write the full thing and slave away in a cabin in the woods for multiple years and hope that you emerged with a bestseller. And if you didn't, too bad, you wasted 10 years of your life. Now you have an idea, you can tweet it out into an algorithm that's going to show it to a lot of interested people and they're going to give you that instant feedback. So that's kind of the digital writing versus legacy writing approach that we talk about in Ship 30, which is you now have access to rapid-fire feedback loops for all of your ideas such that you have no excuse now to invest a lot of time writing something that the market has not already validated that they're interested in. You look at a lot of the successful writers right now, like Morgan Housel, Shane Parrish, uh, Polina Marinova, a lot of these writers who are coming out with a lot of successful books. have proven these ideas on their Twitter account for years. And of course, people are going to buy it because they built up credibility and they validated those ideas over the last decade.

That's a genius idea. And that's the concept, I guess, what you've also been doing. And I think I've been doing with like building in public, like the idea of sharing things, everything in public and seeing where resonance happens, right? Because resonance is the validation that you're talking about.

Exactly. We talk about there's 2 types of content. There's reach content and resonance content. Reach content is the 9 books that will blow your mind about X thing where those go viral and it actually doesn't matter who writes it because you actually, you don't even look at who wrote it. You just look at the content. And so there's no resonance with the writer versus when you write a story and share some lessons or you build in public and share your journey so far, the reader gets to the bottom of that and goes, wow, that was actually, that was a valuable writing and I'm glad I read it, but now I feel more affinity towards this person. And that is what you're going for with testing ideas as well, is you want to figure out what ideas can I share that if I can sprinkle on my personal story, people are going to then say, I just like reading you, not only for your ideas, but because I like following along.

Yeah. For the longest time, I've had a lot of trouble with the concept and the validity, I guess, of this reach content that you talk about. Because to me, I had this mental limitations. So let's call it a self-imposed limitation here that all content aimed at reaching more people that is kind of supposed to go viral is bad content. I was like really, and even like until a couple months ago against like this kind of virality seeking because it feels to me often that the concepts and the formulas you apply for that or to that kind of content to make it have reach harms often or can harm your existing audience that is already there. Because like, what I thought was, well, if you— if I write to get new people interested in me, it kind of doesn't serve the other people that are already there, right? Whereas if I write for the people that are already there, it might also attract new people.

How can you help me overcome this limitation? Because I know that writing stuff to attract more people is good, because it will attract more people to the things I have to say.

I'll give you 2 frameworks that I think about a lot for this type of content. First is my general content raiser right now, which is how I decide whether or not I publish something, is I want to create content that only I can create that I also would enjoy to consume. Now, that might mean there are some pieces I put out that are more on the reach side that I then have to figure out, well, how can I make this valuable? Do I care about 7 Google Chrome extensions that will 10x my productivity? No. So I'm not going to publish those. But will I potentially look at, like, I published something today about Gary Halbert's writing tips, and it was something I've proven in the past that has gone viral and people enjoyed. I make sure to put my own personal spin on it of my interpretation and how I'm using his principles. So it's only content that I could create. And I make sure before I hit publish on anything, would my former self have found this valuable? Then you can dial up the size of the question. So we talk about the size of the question dictates the size of the audience. So something like how to be happier, how to make more money is going to be a lot bigger than how to grow your niche podcast from 2K to 10K downloads, right? So if you look at potential things that you could share that would widen your top of funnel is really the right word for it, of people just to find you and then keep your resonance content of like sharing the more actionable stuff that you're working on on a daily basis. The hard part to get over, and I still struggle with this, is I think we overestimate how much of our content all of our followers see. Right. So when you say something like, I don't necessarily want to publish this because it's so top of funnel that my readers who are already reading me aren't going to get more value out of it, I think we sit there and think we're kind of the center of the universe and it's like every single thing I publish. And my fun story about this is when I wrote my newsletter for those first like 35, 40 weeks, I had like a couple hundred subscribers. And I remember going out of my way multiple times, like heavily inconveniencing myself to publish on a Sunday because I wanted to keep my streak. Wow. And I just felt like there's these 300 people and they're going to, if I don't publish, like Oh no, they're never going to read me again. And they're waiting, refreshing their browsers at 10:00 AM, waiting for me. And so one Sunday I could not get back to my computer and I didn't publish it. And I was like, oh no, it's over. I'm going to have 50 emails in my inbox being like, I can't believe that I've been reading you for all this time. You didn't publish. And I finally got back to my computer on Monday and I opened up my email and there were zero people. Wow. who messaged me like, hey, where's the newsletter? And I remember that all the time because I think we overestimate our relative importance. And most people have so much going on, they're way too busy thinking about themselves to be like, oh, he's writing in a different way and I'm not finding, you know, I think that'd be my like small tough love piece of advice because I feel that all the time still to this day.

Oh, me too. I actually had that last week as well. Similarly, I integrated, I think that the ConvertKit sponsor network into my newsletter because I started working with them for, you know, ads and sponsorships. sponsorship in the newsletter itself. And I was so afraid to send out that email with the first kind of programmatically generated ads. Because I never had that in there. I always just had like sponsors that reached out to me, I helped them with copy, put it in. But now it's just a little fragment and they insert ads that fit the person that the newsletter goes out to. And I was like, I'm probably gonna get like, I have 20,000 subscribers on the newsletter now, I'm probably gonna get 10,000 emails about people complaining and massive unsubscribes because people don't want ads or whatever. Zero. Zero people.

Isn't it crazy how we can build up these stories in our head and they just have zero evidence to back them, but can dictate so many of our actions? I think about that all the time. It's not an easy problem to solve, but at least we can start to inch closer from a self-awareness perspective when those biases start to present themselves.

I think having a conversation like this where 2 people who do this regularly still share this, it's like imposter syndrome, which we all have in many different ways and different intensities. I think that's important. And I think it's also, and it's kind of what I tried to hint at with the whole solitude, solitary thing of writing, the creator life is a fairly kind of encapsulated, isolated life, right? A lot of the things we do happen in here, and they barely leave our head before we turn it into the shape in which we want to deliver the thing. So, you know, there's a lot of involuntary feedback mechanisms and feedback cycles in the brain that we probably shouldn't have running most of the time.

Yeah. And so I agree, having a couple people that you can stress test the absurdity of some of these beliefs with is very powerful. Like, I'm lucky to have my co-founder Cole where I sit down, I'm like, oh dude, it's all over. I'm freaking out about this. He's like, no, that's just not going to happen. And then all you need is a little, you really only need one person to tell you that that idea kind of doesn't make any sense. And you get out of your head. You're like, oh yeah, you're right. Okay, thanks. On to the next thing.

Yeah. Yeah, you do get stuck with this. I'm fortunate to have a partner, my girlfriend. She's amazing with this. She just pulls me back out and she has this kind of bird's eye perspective on what I'm doing. You know, because I'm in the trenches, I'm in the arena.

Yeah.

But she gets to see like the bigger picture. And it's nice to have this conversation. So I guess have a great partner either in life or in business to help you out of this is interesting. And that's, I guess, something new for creators. Like I see this accountability group thinking that you have, like where you find people who are on the same journey and masterminds, you have that too, right?

The idea of having people that are your peers that are on the same kind of stage of what you're doing, and having consistent exchange with them. I feel that's new. I don't think I've ever really been part of these kinds of groups. And now I am. And it's so much better.

It's so much better because you recognize how difficult is it for you to find people to have a conversation about the biggest problems you're facing as you scale your podcast from X to Y. Like you can't talk to your high school friends. You can't talk to the people that you work out at the gym with. You can't, like the amount of context to have The conversation that you actually need to have, the number of people are so few that you have to go and intentionally find and set those groups up yourself to make sure that you have that feedback of ideas. Because otherwise you just end up in that spiral where you're playing a solo game for no reason other than you haven't found those people. But once you find them, this game becomes so much more fun because especially the early on, like I wish I had built more of those relationships at the beginning of my journey, and I have, and I'm still close with some of them, and I've gotten to grow with a handful of people throughout kind of my creator journey. But you get that double compounding because you're getting better, your relationship is getting better, and the other person is getting better, which means the conversations you can have further and further down the line, you both have more skills. So for anyone's like, yeah, I feel very lonely in this journey, it's you just intentionally figure out how to take the same attitude, positive sum that you bring to Twitter all the time. If you just bring that, you're going to attract people at the same stage of your journey. And that's what those relationships are really the main bread and butter of why you should be creating in the first place is because as those compound, those are the most fulfilling.

Yeah. That's, and it's all, it's also kind of almost a side effect or kind of a consequence of doing this in public in front of people, right? Not just writing, in complete solitude and then publishing every now and then, but being this enigma of a person. I think that used to be a thing for writers, right? Where you were so untouchable and you were so mysterious, and it still is. But I don't think it's in the creative space, particularly in the, in the audience-driven creative space. This just doesn't work anymore, right?

It really doesn't. And the evidence is in the people who've had the most success. They are not spending years slaving away over their manuscript hoping that a publisher picks it up. It's, no, I've built a newsletter to 200,000 subscribers. Here's your 7-figure book advance because of that. That's the new game that we're playing. And so the more that you can tap into it, you're just at a bigger advantage and it's more fulfilling. You get to engage with your readers the entire time on your journey up rather than hoping that you just drop this masterpiece at the end.

Yeah.

And they also get to tell you if it's good or not while you create it. That was, that was my experience with my second book. I think I had What was it like 500 beta readers, which was quite an interesting group of people to wrangle. But you know, it was a lot of feedback. Let's just say that, right. But it was incredibly powerful because the book that came out of it was a different book that I intended to write. And I'm glad for it because that's the book they needed, right? It's not the book I wanted. It's the book they needed, which is yet again a validation of necessity and problem rather than just a solution looking for a problem.

Is this Zero to Bootstrapped? What's the name of it? Can you remind me?

The second one I wrote is called The Embedded Entrepreneur.

Right. What was the one before that?

Zero to Sold. That's my first book.

Zero to Sold. That's right. I remember, and it's so funny you say this about the beta readers, because I remember watching your Twitter as you were writing it, where you would post the Ulysses word count of like, knocked out this many words. Here's what I wrote about today. And the comments were like, oh my goodness, can I read this chapter? And it makes sense that when you publish that book, You had voracious readers ready to knock it down and it was solving the right problem. So you're the perfect example of what we call lean writing, which is you are validating those ideas as you go, just like the best startups are validating their product as they go. It's really the same thing. You're just the CEO of your writing and that's your product.

Yeah, absolutely.

That, that's one of the biggest things I've learned over the last also like 3 years, just like you kind of started around 2020, late 2019, like days before the world changed, right? That was kind of when I started there. So I've noticed the same thing. I've been running software businesses before, and they had their own internal dynamics. And now that I run a media business, which is a writer— being a writer is all about kind of, I guess, you are a media person or a media product creator. It's the exact same thing. Right. It's structurally the exact same thing. You have a product, which is whatever it is, right? Might be writing, might be a software thing. It's both writing, just one is for machines, the other one is for people. And the mechanisms with which it grows into a better product is the exact same. Small iterations, close feedback loops with the people that the iteration is supposed to help, right? Or in the product in general. I've seen the exact same thing. SaaS business, media business, structurally exactly the same, which is funny because I wrote Zero to Sold thinking this is for SaaS businesses only. It kind of says bootstrap SaaS business on the title. But I could cut the SaaS part out and take a couple chapters about tech stacks out there, even though even these articles where I talk about choose the tech you know, That translates to writing just the same, right?

You don't need to install Scrivener or Ulysses or whatever. Just use Word if you want to write. The words matter, not the tools. And it's the same for software.

Yeah, just to double-click on that, because there are so many people out there who are paralyzed getting started writing because they're like, I can't write anything until my Notion dashboard is perfectly optimized, ready for this content flow that is just beautifully optimized. And I hit every— no, My ideas, nope. It's, I've been using Apple Notes to write for a long time now because it's the only thing that intentionally doesn't have anything shiny that is going to go pull my attention away from doing the writing itself.

Yeah, that's great. Yeah, that's that.

I've recently started like writing in audio a little bit.

Like I've started just talking because to me, writing is thinking. And I think that it's just a different word for that, right? A different kind of way of thinking in a in a specific kind of technical term. But I started just dictating stuff into— I use AudioPen. I had Luis Pereira on the show and I talked to him about his tool, which is just, you know, it records you and then it kind of slightly summarizes it using like OpenAI. And I use that as my baseline outline. And then I start like, you know, filling it up.

2 things there. First, so Luis Pereira was the very first paying customer of Ship 30 that I didn't promise their money back to. Oh, wow. So very, I still remember his name, $99, and it's legendary to see all the cool stuff that he's gone on and built. But Lewis will always hold a special place in my heart because right when you said that, I was just brought to so many memories of seeing that first stripe of $99 when I put it for sale with no money back if you wrote every day for 30 days. So, so funny you mentioned that. Shout out Lewis if he's listening. But on top of that, yes, I find writing is the best vehicle for thinking because you've experienced this too, as you've been writing. Now, when people have conversations with you, when they ask you a question, 90-plus percent of the time, I would wager that your head jumps to a topic or a concept that you've already written about. And because you've already written about it, you've thought through it clearly and you can articulate it better than other people who just riff off the cuff. And so writing is really pre-thinking future conversations you're going to have, and you just are figuring it out during the writing process.

I love that. That is such a great way to explain it. And beyond pre-thinking, which is definitely an amazing part, it's also you have a tangible asset to give to people, right? Here are like weeks worth of thoughts distilled into thousands of words on the exact thing that you just asked me about. Enjoy, right? You link them, which is such a wonderful thing to be able to do. Yeah. I mean, you don't have to convince me that writing is amazing. But I think the potential for it to impact Not just money concerns, which are important, but also just the scope of the topics that you have consciously confronted with your mind.

And then having this, this kind of long tail of like evidence of your thinking out there for people to find. That is just such a massive investment into your future.

And the key thing to keep in mind here, and what keeps a lot of people from writing in the first place is they think they don't have anything valuable to say. And so we have them conduct what we call the 2-year test, which is over the last 2 years, you look back and you reflect on skills you've built, life transitions you've made, hobbies you've started, jobs you've stopped, started, jobs you've quit, topics you've learned, rabbit holes you've gone down, et cetera. And picture for a second that your 2-years-ago self got to have a conversation with current you. Think about how valuable they would— they'd sit and talk to you for hours. They'd ask you hundreds of questions. of all the things that you've gone on and learned. That's the same thing that writing on the internet is. You are going to take the ideas that have now become painfully obvious to you, but would've been incredibly valuable to your earlier self 2 years ago, and you're going to write and share those ideas. And the internet again guarantees, like we talked about earlier, that there are tons of people at that old stage of the journey that you used to be on who would find it valuable. And that is really the entire game that I've been playing for the last few years is learn a topic, write about it to my former self, where in that process of writing it, I better understand it. At the same time, I build credibility with people behind me while also learning from people ahead of me. And I've just been continuing that path all the last 3 years, and I intend to for the next 50 years of my life.

Oh, I bet. Well, I'm going to be there for those, for those 50 years if I physically can. But yes, that's super stringently put because we tend to only look at the people ahead of us, right? That's the kind of the star appeal that we just, I think we're socialized with, look at the people who are better than you so you can learn. But the fact that you can actually teach to the people who are behind you on the same journey, that seems to be somewhat, you know, suppressed in terms of what we get taught about. But I think it's such a central part of why we should write and why we should create.

Yeah, you end up better understanding the ideas that you thought you understood well. Like if you think you understand something, try to teach it to someone who's 2 years behind you. And you quickly realize, ah, maybe I don't, and maybe I'm not as good as I think. And that writing just forces you to level up.

Yeah.

And in a funny way, in doing that, you also get to a level where you can teach the people ahead of you as well, because the thing that you create gives them a different perspective on the thing that they also think they already know. But they're learners too, right? I had Aaron Francis on the podcast just a couple weeks ago. And he's into screencasting and all that kind of stuff. And he knows there are way better people that do like screencasts and videos, but his style, his unique style is also an inspiration for them, not just for the people who come up behind them who want to do things like he does, but also to the people that he learned from and he admires. I think that circle, circular thing that in you teaching, you learn things that you can teach the people who teach you. It's kind of a Möbius band of feedback, right? This infinite thing that just wraps around you and the people that you care about in this interesting and multidimensional way.

A great example of this was in February of 2021, I kind of hit an inflection point when I published a Twitter thread that was probably 2 months before that of 12 questions that changed my life, 12 journal questions that I reflected on. And that was inspired by Tim Ferriss's article of 18 questions that changed his life. I saw those and was like, wow, a handful of these I'm going to ask myself. So I'm learning from him. And then I was getting a haircut and I get a text message with a screenshot from one of my buddies. And it's a screenshot of Tim Ferriss's 5-Bullet Friday. And the first item that he linked to was my Twitter thread talking about questions that I was reflecting on. And he said, adding a few of these questions to my list, really enjoyed it. And there's the perfect example of someone that I had learned at the time. I'd listened to every Tim Ferriss episode. Wow. So I still remember I was getting my haircut. I'm like halfway through and I see this text and I tell the barber, I'm like, you gotta stop. And I'm got like half my head shaved and I walk over and I'm like freaking out because what do I do with all this? I'm getting a bunch of texts now and it, it's starting to go viral on Twitter. So, oh, nice. So funny. And just a great example of, yes, you learn from the people ahead of you, teach those behind you, because that's all I was doing was saying, wow, I'm learning from Tim. I'm behind him, but I'm also have a bunch of experience from the last couple years from these questions. I need to publish those because I feel morally obligated to the people behind me. And then in the meantime, he got to pick up a few as well. So it is so fun when that comes full circle.

Yeah, I'm really happy for you. That must have been a wonderful experience. But it just shows that if you're just your authentic self, and you are taking things from other people and adjusting them and, you know, making things your own, and then sharing that back, which is the big part, right? The big part is not just keeping them to yourself, but actually sharing them back. A lot of interesting things can happen.

Especially, just one final point on that, especially in the age of algorithmic timelines, you never know whose For You page you're going to end up on, which means you right now could publish something that pops up on Jeff Bezos's timeline. Never before in human history has that been possible. So again, if there, you need another reason to actually go and publish your thoughts, there's another one.

Digital writing is the great leveler, right? The great equalizer in many ways.

Like if what you do is good, it doesn't really matter how well you're connected, or who you know, or, you know, who follows whom, like it will get to the weirdest and most interesting opportunity spaces possible. That's so cool. Yeah, I'm really happy for you. And really happy for everybody who's writing, to be honest. And I'm glad. And that's the thing why I'm so excited to talk to you about all this, that Ship 30 even exists. Yeah. Because that to me conceptually, it has unblocked so many people, thousands, and hopefully soon tens of thousands at the same time. That is an interesting business. And I think it's just a calling that you fell into or that you found, I guess, which is super cool. Beyond Chip 30, I know you're doing a couple more things. And that's also something that I found very interesting looking at you not just as a writer, but as a business owner, right? As a person running businesses, you've diversified in several different ways. And one of the interesting things that I found is Typeshare. That is something that you also built, which is a software business, which is— I said it earlier, it's structurally the same as a media business, but it is technically something different. What drove you to build that in particular?

So Typeshare was born, we had been writing our atomic essays during Ship 30 cohorts, like via the Apple Notes app or like screenshotting. Yeah, I remember that. Your Word. And Sam, the founder, came to us and said, hey, I built this thing that I think your students would love. It would allow them to publish high-quality visual atomic essays. We're like, this is great. Absolutely. And so that was in August of '21. So a little over 2 years ago, we've been building basically the software version of Ship 30, which is if our mission, within Ship 30s to help a million people start writing on the internet. We can reach a good bit of them, but at the end of the day, the most helpful thing for people will be to set up the publishing and everything that could take someone who's never written about— I use my mom as an example who's writing. She's been a part of 20 cohorts. And I try to think, how could we have gotten her to write with software 2 or 3 years ago? And that's kind of the entire product vision is someone who has some kind of ideas in their head. They open up Typeshare and it pulls all of those ideas out of them. So it asks them questions, it preps the page for them, it gives them templates, it shows them analytics, it helps them write headlines, it helps them format, it helps them do everything where basically, like you said, they could just speak. Like that's where we're headed is that the ideas in your head, the amount of friction to go from idea that you have to published asset in the real world. We're trying to minimize that time and minimize all the friction that keeps millions of people from being able to do that. So yeah, Typeshare is founded by Sam, and then Cole and I are co-founders with that as well. Um, and we onboard people during Ship 30 into Typeshare and they get to use that. And then also people find Typeshare from other areas, but a lot of fun, a lot more difficult to build a software business, as I'm sure you know, than a media business. Like they're similar, but— One is a lot harder. And there's a reason why people raise money for these kinds of things, because you do need a talented team. So we've learned, we're still learning and still growing Typeshare and figuring out what role it wants to, what role we want it to play in kind of our overall business portfolio. But it's been a lot of fun, a lot of lessons.

Yeah, I bet. Yeah. And software, unlike people, either it works or it doesn't, right? There's no in between. That's, that's one of the big problems there, man. Since you mentioned your mom and her blog, It is. I don't know how it feels. And I do want to ask you, how does it feel to have your mother blog on your software?

Like, so it's funny because my mom's story, she's been pivotal to the entire Ship 30 journey where back up to April, no, May of 2018. So I'm a senior in college and I'm about to graduate and I receive a phone call from her that she's been diagnosed with stage 4 ovarian cancer. And that shook me pretty heavily at the time. I ended up going home right after that emergency surgery, whole 9 yards. And that was right as I was about to go enter the real world to work at BlackRock. I took care of her for 2 or 3 months. She was on the path to recovery, and then I went and started working in New York, but it gutted me to be away from her and recognize that I didn't have the freedom if I wanted to, to go spend more time with her. Fast forward a year and a half into 2020 when they sent us to work from home. I got to go live back with her during that time, and she was actually rediagnosed with a small recurrence while I was her primary caretaker then during 2021. During all of the Ship 30 cohorts, she was writing, and that was one of her vehicles through recovery was I could write and share my ideas and talk about stories. She shared tons of information about how to you know, best care for someone dealing with cancer, how to talk to them, how to have conversations. She's recently started a nonprofit, all based on the ideas that she's shared and attention she's generated. So it's so fun to have her back for every cohort. She's kind of like a mini celebrity where we do breakout rooms at the end of every, uh, at the end of every live session. And I always get a bunch of messages from people like, oh, I got to be in a breakout room with your mom. It was so much fun. And so she loves being a part of it. And it's so cool to see she's writing right now. We did a trip to Greece, uh, over this summer, which was kind of a dream trip for her. She'd always wanted to go there. And I had made that promise when she beat cancer for the second time that we'd go to Greece. And so now during this cohort of Ship 30 that we're currently on, she's writing a bunch of essays recapping our trip. So I get to read those. It's, it's super special and a lot of fun. And I appreciate you asking that because she's been such a pivotal part. She was there from that original tweet. She was supporting me every step of the way. It's, it's been great.

Well, I would like to give her a massive shout out because I've been reading all her blog posts in preparation

for this

episode. Amazing. First off, she loves you from such a deep place. It's really incredible. That is such a— you can really feel it. I was tearing up a couple of times during, during those blog posts. And I really mean it. It was, it was a wonderful and it felt like a very private thing, but that was still public. That I'm really happy that she shared that and that she shares how proud she is of you and how amazing you are as a son

and as a person, as a human being. I mean, there's a lot of stories in there about you as a kid and all that, that give— if I know you from Twitter, I know your adult, fully realized self. But through her stories, I also get the person and the story that happened along the way. There's texture, you know. Yeah, a lot of texture and a lot of heartwarming, a lot of embrace around it. It's really cool. And to see her and her story and your, as you said, pivotal part in all this and her pivotal part in your story. I love this. I really, I was so happy that I found her blog on your product. Right. It was such a perfect storm of love and kindness It's all in one. It was really wonderful.

So I just, I appreciate that. And I know she's going to love listening to this. So shout out, Mom, as you're listening to this. Thanks. This is proof that you need to keep writing, right? Sometimes she wakes up, she's like, oh, no one's reading this. I'm like, you have no clue the amount of impact that your writing has every single time. So my cheeks hurt from smiling so much. Thanks for, thanks for telling that story. And I know she's, she's smiling listening to this.

And you seem to be a great teacher of writing as well. If she is not also a great writer to begin with and taught you all these things. But the way that her blog posts in particular, like, if she's part of Ship 30, let's just talk about her writing for a second here. Yeah, they're really short blog posts, but they're impactful.

They're thematically focused. They're narratively rich. Texture is the word. They add so much to just learning. Like, I could turn what she wrote in a tiny little 2-sentence tweet, and it would have none of the richness and the feeling that comes from these, these stories that she writes. So you must be a great writing teacher if, if that is the outcome of Ship 30, man.

I think, I think I was born with it from her and it just took me a few years to encapsulate it. So it's been fun to have, like I said, with Typeshare, it's like she's the, the best Typeshare product critic because I just talk about like the, what is it, the Collison installs where the Collison brothers used to sit over the shoulder and they'd watch people like click on their software, right? I've been doing that with her and Typeshare. I'm like, All right, team, my mom can't find this button. That means we got to redo this thing because if she can't find it, that means no one else can either. So it's been fun across the board where she gives feedback on just about everything, for better or worse, you know?

Yeah. Well, that's the thing.

For better. Exactly.

Probably for better. And if it's worse, then it's still better, right? It also puts a completely new meaning to the mom test, which I think Rob Fitzpatrick would really like conceptually, right?

Yes, exactly.

That's wonderful. I'm really happy to hear this. And I think that's— now you are my favorite family business now.

Oh, man, I appreciate that. That's awesome. Yes.

Well, okay, so you have Typeshare, you have Ship30. Is there anything else that you're currently working on that's interesting?

We have a couple other that we are dabbling in. So one is our Write with AI paid newsletter. So we have a paid newsletter, that we're growing right now that's $20 a month that gives ongoing updated information on how to best turn ChatGPT, Bard, other AI writing assistants into your personal intern. So that is a paid newsletter on Substack that we find that is one type of information that is going to be changing so rapidly that you want to stay on the cutting edge of it, which is why it's a paid subscription newsletter. Why? Because you get 2 editions every week that's going to show you how to stay on the cutting edge of using AI as a digital writer. So that's been a lot of fun. We have a vision for kind of a suite of paid newsletters where we're getting to the point of our business where we're interested in decentralization, where rather than focus on one product from one type of person, we want multiple products. So we have software, we have paid newsletters, we have group coaching, we have cohort-based courses, we have digital courses, we have everything to kind of build out this entire ecosystem. That as you mature as a business is really the goal. So you're not dependent on one thing where for the first year we sold one thing to one person and got to $1 million and that was Ship 30. And then as you get to different levels, you want to expand who you market to, who you sell to, and how reliant you are on all of those people. So that's one with our paid newsletter. And then the one that we've been giving a lot of focus is our premium ghostwriting academy. So this is a group coaching program that helps freelance writers become premium ghostwriters. We teach them everything they need to avoid the freelance writing hamster wheel. And we also help people who are stuck in 9-to-5s like I was escape that 9-to-5 job using ghostwriting because of everything. There's no startup costs. You don't need a big audience. You really don't need that much skill. That's a very trainable skill. You don't need thousands of people to say yes. You need one person to give you $5,000. And then boom, you see an entirely new world. So we're currently building and growing that as well. So it's kind of a portfolio of different writing businesses all through the lens of our goal is to help people start writing online and monetize and build a lifelong sustainable career out of writing on the internet.

Wow, that is quite the portfolio. And I'm really happy to, to see it honestly, because the more I talk to successful creators and entrepreneurs like yourself, The more I see people intentionally starting with something clearly defined, and then growing a portfolio of de-risked and diversified bets in many different ways and different kinds of products as well. So it's really interesting to see you going from the cohort thing, which is a pretty high presence thing, I guess, into SaaS, which is a low presence, but high, you know, brain melting stuff and high frustration if it doesn't work.

High frustration. is the term there.

Yeah, wherever you have customer service, that's gonna be a problem, right? People send you emails.

And then going into like special consulting and also, you know, just teaching people in different ways. That is really, really interesting to see. That would also be an interesting topic that I would like to hear your long-term learnings from one day when it turns into like a bigger portfolio of things.

Yeah, we've been doing that with our Espresso Hour podcast, which is basically Cole and I were sitting down twice a week, Monday and Friday. Monday, we'd set the plan for the week. Friday, we would recap what happened with the business. And one day we're like, why don't we just record this? And people loved it because we were just like, no, there's no one that you can get the level of depth and richness of insight from a group of 2 guys building a portfolio of internet companies. And so we love doing that because again, it goes back to this free upside. Worst case, we were going to record it anyway. Best case, people pay attention and now we have new product ideas. So We have a massive problem in our business right now, which is we have too many ideas that we want to go and execute, which is a great problem to have that I've reframed of like, I know that we're going to grow forever because we have 50 low-hanging fruit to improve every single product on top of the 50 other product ideas that we eventually have. So it's, it's a fun game to get to sit down and play. And I'm sure you feel the same way every day.

Yeah. Oh, for sure.

And it's really nice to see you like the podcast in particular. That's so building in public.

This is literally allowing people to be a fly on the wall behind the scenes. Like, if you're not listening to this podcast, what are you doing? It's kind of what I'm wondering. So listen to the podcast. Where else do you want people to go and find you and follow you along your amazing journey here?

I spend too much time on Twitter and X. That's @DickieBush. I write on LinkedIn, write on Instagram. I'm the same there. I'd say it depends on what you're looking to do. If you are looking to start writing on the internet, the best place to go is startwritingonline.com. That's our free 7-day email course with everything you need to get started. If you're already writing and you want to start writing with AI, you can go to startwritingwithai.com and that'll have a free email course that'll help you there. If my story about working on Wall Street and eventually leaving kind of resonated with you, I'd recommend exploring the world of ghostwriting. So you can go to premiumghostwritingblueprint.com and you'll get a bunch of information there. So those are kind of the big 3. And then Typeshare, if you're interested in, hey, I love writing and I just want a better software platform to go and do it all. you can go there too. So a lot there could be changed. It could all change by the time this episode goes out because that's just the way this all goes. So I appreciate that. And it's been just a fun journey. And I think back to when we met, where this is really the first time we've exchanged and chatted. Right. And I've been kind of Twitter friends for a long time, but it really was like that early 2019, 2020 when I watched you write the new, the Embedded Entrepreneur book. And I remember seeing that, I'm like, he's just doing everything that we talk about. It's awesome. You're validating your ideas. You're bringing the public with you. They're all ravenously ready to read it. So I'm excited. Do you have any other books in the works?

Oh yeah. I'm writing my third one on building in public, probably unsurprisingly, but, you know, that's, that's, that's where I'm currently at. And I'm, I'm not self-publishing this one. This time, this time I'm going a bit bigger, which is also fun. And it introduces me to new issues with the actual feedback cycle, because now specialists are involved, and they tend not to want people involved too much. So yeah, trying to juggle that, which is going to be a whole other little challenge for me. But yeah, I'm— I can't stop writing. I mean, I write every week, right, for my own podcast and stuff. But I do want to get the new one out too. Yeah, I'm excited.

Well, definitely keep us in the loop on how that one's going and reach out to Cole too, because that's one of his favorite topics he has such a strong opinion on, self-publishing versus going the traditional publishing route. Like if we eventually write, I think the pinnacle book on building a daily writing habit, that we will go publish or work with a publisher or work with a book deal because the goal would be to get it to as many people as possible. But the rest of our books, we want to publish in a niche way because we don't want that bureaucracy and specialists to say, hey, we own your next 10 books. It's like, we're publishing one under your name to get as many people as possible, try to play the New York Times bestseller game. But otherwise, it's self-publish all the way.

That's an interesting observation. I feel the same way. Like the first 2 I wrote were kind of indie hacker niche specific. But this one has the potential to just help people generally build whatever they want or do whatever they want in front of an audience, right? And benefit from those. So I think there's a lot of overlap between what we're doing because Effectively, we're just teaching people to build their own legacy in different ways, right?

I'm really happy that you shared all these insights and all the plans with me today. I'm like, I was already like 99.8% excited to follow your journey. Now I'm at like 157% excitement.

Amazing.

If that's possible. I'm super happy. I'm happy to finally get to talk to you. I'm happy to see how all of this fits together. I'm glad we talked about your mom because she's awesome. And I'm really happy that to see where this is going. So thank you so much for being on the show. That was a wonderful conversation. Thanks for all the things you shared.

Arvid, thanks so much. And again, I really appreciate just the warmth and energy and positivity you bring to The Timeline, this podcast. It's awesome. So I'm excited to keep listening in and hopefully we do another one in a couple of years. We look back on this one and go, here's all the things we've gone and done since then. Here's all the books and all the good times we've had. So I appreciate you having me.

Well, thank you so much.

Awesome.

Boom.

Boom indeed. What a guy. There's just something about a founder who has a plan, a vision for their future. I will now briefly thank my sponsor for this episode today, acquire.com. Imagine this, you're a founder who's built a solid SaaS product, you acquired customers, and all of this is generating really consistent monthly recurring revenue. It's the dream of every SaaS entrepreneur, right? Everybody wants to build this company. The problem is— You're not growing as much as you like for whatever reason. Maybe it's a lack of focus, a lack of skill, a plain lack of interest, and you just feel stuck in your business. What should you do? Well, the story that I would like to hear is that you buckled down and you reignited that fire within and started working on the business, not just in the business. And you did all these things you always wanted to do. You built an audience, you do marketing, sales, and outreach, and 6 months down the road, you made all that money, you've tripled your revenue, and you have now a very hyper-successful business.

Wouldn't that be great? But reality is that unfortunately, it's just not that simple. And the situation that you might be in, well, it looks different for every founder who's facing this crossroad. But too many times, the story here ends up being one of inaction or even stagnation. Until the business itself becomes less and less valuable over time, or at worst, completely worthless.

So if you find yourself here already, or you think your story is likely headed down a similar road, I would consider just another option, a third option, and that's selling your business on acquire.com. Because capitalizing on the value of your time today, that's a pretty smart move that you can also make. And acquire.com is free to list. They've helped hundreds of founders already. Just take a look, go to try.acquire.com/arvid and see for yourself if this is the right option for you and your business at this time. Again, just take a look, won't hurt. Thank you for listening to The Bootstrapped Founder today. You can find me on Twitter @arvidkahl, A-R-V-I-D K-A-H-L, and you'll find my books and my Twitter course there too. If you wanna support me and this show, which I would really appreciate, please subscribe to my YouTube channel, get the podcast in your podcast player of choice, And leave a rating and a review by going to ratethispodcast.com/founder. It makes a massive difference if you show up there because then the podcast will show up in other people's feeds. And we talked about this on the show. That's where you wanna show up. Any of this will help the show. I really appreciate it. Thank you so much for listening. Have a wonderful day and bye-bye. Bye-bye.