How to Build A Wildly Popular Newsletter in Six Months

Nathan Baschez and Dan Shipper explain the meteoric rise of their paid newsletter bundle, Everything

Nathan Baschez, founder of Divinations, and Dan Shipper, founder of Superorganizers, join Stew Fortier to discuss the ups and downs of building a six-figure newsletter business in six months.

The summary and transcript below were prepared for Compound Writing, a paid invite-only community of online writers. Apply here

What should I write about?

Find a topic that makes you come alive and start there. Over time, you will develop a voice and worldview that will guide the narrative of your newsletter.

Don’t fall into the trap of pre-defining the scope of your writing in the early phases. Some writers worry that they need to identify the one topic that they can elaborate on for many years, but this is unnecessary. Writing and publishing consistently are the two most critical habits that will help you discover who you are as a writer.

Focus on each essay individually. Once you’ve developed a small portfolio, take a moment to zoom out and see the forest through the trees. Over time, you will develop a unifying theory that is organic to you and reflective of your passions and strengths.

How do I get started?

Don’t put too much pressure on yourself to succeed quickly. Focus on what you want to say rather than immediate growth. It's important to have something that you want to say that you're excited about and have that be enough.

There’s often a temptation to spend a lot of time preparing before you launch your newsletter, but this can be antithetical to the process that will yield the highest result. Just write the articles.

In the early stages, separate yourself from the “results” or performance metrics of your writing and instead focus on the writing process itself. Hold yourself accountable to your inputs.

We always say that your writing should be a reflection of you as a person. It should tap into your soul and what makes you tick. The minute you find yourself writing articles because you feel like you have to, or you feel like it's the right thing to do, the content will suffer.

Over time, as you develop confidence as a writer, you can begin to incorporate data and insights to help drive your writing.

Finding Your “Signature Move”

Over time, it’s important to develop a personal style and approach to writing that keeps your readers engaged and distinguishes you from other industry thought leaders. It will take some trial and error, but once you find it, you can continue to employ your “signature move,” refining it so you understand why it works.

With Divinations, Nathan identified two writing strategies that drove growth. The first was analyzing a topic of conversation in tech Twitter and providing an analysis framework from business school literature. His second winning strategy was breaking down business school literature and explaining it in a digestible way for the reader. The latter “move” was more natural fit for paid content, which is the explainer, while former is ideal for free growth because it is commenting on timely discussions.

To find your own “signature move” or writing strategy, focus on what you feel compelled to write and don’t be afraid to experiment. If you feel like the approach you are taking isn’t working, give yourself permission to try something different for next week.

Evergreen vs. Timely Content

Both evergreen and timely content can serve their distinct purposes. If you're writing something evergreen that's not timely and not part of the current conversation, it can be harder to capture the attention of your reader.

How often should I ship? What length of article works best?

Aim to write and publish on a weekly basis. We try to write one long-form and a few short-form articles per week.

Both short and long-form content can be successful, depending on the context. In our experience, long-form content tends to be shared more frequently, while short-form articles work well in emails. Long-form articles are also generally better for paid content.

If you’re struggling to get your ideas on paper, start by writing short. Write 500 words and make it a good 500 words. Expand from there.

How to Get Comfortable with Sharing Your Ideas Online

Feedback from others is a necessary but sometimes painful part of becoming a better writer and building a lucrative business, but that doesn’t mean you have to start by publishing to the entire world.

Start with a few friends on a private newsletter, or even just an email. Compound Writing is actually perfect for this.

What are the “core engines” that drive your success?

We’ve learned through our experience that there are a number of drivers or “core engines” that continue to deliver growth. Nathan always asks himself if his writing fulfills a few basic premises: is it surprising? Is it important? Is it true? Is it relevant? This is the foundational framework for every piece of writing he produces.

We also choose to style our writing in a way that is distinct from other newsletters in the industry. Our approach with Superorganizers and Divinations is to make you feel like you're sitting down to dinner with a really smart friend who knows a lot about productivity or strategy. We try to go into a lot of detail and write long-form articles around what we are passionate about. It works for us.

How do you build an audience?

You don’t have to have a large pre-established audience to develop a successful newsletter.

Involve other people in your newsletter. Interviews can serve as a significant growth-engine in their ability to tap into your subject’s pre-existing audience. Start with friends and acquaintances. As you build your subscriber base over time, you can climb the ladder of influence and obtain higher profile interviews. The people we interview now are far different and more famous than the people that we interviewed at the beginning.

Also consider co-writing articles with individuals that will expand the scope and reach of your writing.

Tap into like-minded communities. Find communities of people online that are interested in what you’re interested in. Engage with them regularly.

Offer premium services to subscribers. Anytime anyone signed up for a paid plan with Superorganizers, Dan emailed them and said, “Hey, do you want to do coaching?” and offered a 30-minute, one-on-one productivity coaching session with them. Dan met so many readers that way. The experience was fun, provided a lot of immediate value in their subscription, and even inspired content for future articles.

What have you seen negatively impact growth? What drags the engines down?

There are some basic mechanics you need to have in place to grow. Does your article have a shareable title, or is it just “Dan’s Newsletter #5?”

Do you have a clear call-to-action to generate subscribers? Are you publishing frequently and consistently? Basics like this will drag you down and stunt growth if not addressed.

Free Content vs. Paid Content

After publishing a portfolio of free content, you can transition to paid content. Don’t overthink this process or feel as if you need to announce it. With Superorganizers, Dan just turned on the paid feature and people started paying.

Lifestyle and entertainment newsletters generally charge between five and ten dollars per month, while business industry newsletters can bring in ten to fifteen dollars per month.

What’s the most unexpected thing you learned in launching your newsletters?

The sheer profitability and growth potential really surprised us. You can grow quickly – but you need to dedicate a significant amount of time and energy. Having an audience already definitely helps but you can get it going pretty quickly, when you're really consistent about it.


Full Transcript & Highlights

Lightly edited for clarity and highlighted for key takeaways.

Stew: I am just totally thrilled to be sitting here with Nathan and Dan to talk about everything that they've learned, growing appropriately named Everything. So, I'm going to start by talking about the last six months with Everything and and what you two have done to build your audience and your newsletter. What really kind of struck me is that you both have this background, launching, selling and operating companies in Silicon Valley backed by world-class VCs. So, why not do another tech startup? Why launch a paid newsletter as your next business?

Why launch a paid newsletter as your next business?

Nathan Baschez: This all really started with Dan, who started Superorganizers in order to start a tech company. So I think that'd be a good place to start.

Dan Shipper: Yeah, I was not trying to start a newsletter or a media business. I was sort of trying to do another tech startup. Previously, I started and sold an enterprise software company called Firefly and had taken a couple years off and was doing some investing and trying to figure out what I wanted to do. I decided I wanted to start a productivity software company, because I'm super nerdy about productivity stuff. My idea was, in order to start, I will start a newsletter. I will interview a bunch of people. Then I'll use the insights that I gather from the interviews to build a product. And then once I'm done maybe I'll have built a little bit of an audience from the newsletter that I can launch into. So I started doing that in August of last year. Over time, people just really liked the newsletter. I was like, hmm, maybe there's something here. Maybe I shouldn't start a software company, maybe I should just start a newsletter company. I got super excited about paid newsletters, and specifically, business focused, paid newsletters. So I was thinking, who is the best person in the world to start something like that with? Nathan was the first person that came to mind. We've been friends for a long time. Nathan's background makes him probably the best person to do this with. So I called him and he was psyched about it. And if you want to pick it up from there...

Nathan Baschez: Yeah, I worked at Substack for about a year. I was the first employee that they hired right after they finished Y Combinator. I was thinking about what I wanted to do next, and I've always really enjoyed the intersection of media and technology. It's not the most lucrative or hyped part of tech, but I love stories and learning. It's cool to facilitate that. It's cool to sort of use the internet to do that in new and better ways. Maybe it's not like Google or whatever, but who cares? You could build a great business on it. So when I left Substack, I didn't realize that Dan was thinking about starting something like this, but had I known I would have reached out to him instantly because Dan and I have been friends for a long time and have always been, I think we are mutually on each other's list of people we'd love to work with.

So, when Dan reached out to me I was like “Yes! Let's get started.” Dan took the first step and was like “let's just work on these newsletters on our own and maybe it'll become some sort of business or maybe it'll just be a cool project to work on for a little while.” It was really important to not put too much pressure on it early on to succeed because I think especially in media, you can kind of ruin it if you put a lot of pressure on it to succeed really quickly. It has to come from someplace that's distinct from immediate growth. It's important to have something that you want to say that you're excited about and have that be enough.

On December 11th we launched Divinations, and Superorganizers went paid right around the same time. And then for a while, we just really focused on growing it and writing and helping each other and editing each other, and you know, keeping track of metrics together. We really treated it like a business in some ways and a partnership from the start, but we didn't incorporate. It was just sort of like we're putting a lot of focus and energy into this, and maybe something really cool will come from it.

Stew: Yeah, that was something I'm curious about because a lot of people I think on the call are thinking like, “What should I do? I have many interests, maybe even a few areas of expertise. What the heck should I actually double down on and write about? What will people actually pay for, what will be valuable to people?” So I think you both kind of touched on it there with how you stumbled into the topics you chose. I am curious. Do you encourage folks to think about the three or four things they’re really interested in, how do they choose an area of focus? And how do they kind of double down on being disciplined with their subject matter?

Dan Shipper: It's such a good question. And it's interesting because, yeah, I write a productivity newsletter but me saying that, it doesn't include the fact that over the last several years I've worked on like 20 other projects that just haven't worked, that all reflect different parts of my personality. Yes, productivity and knowledge and organizing all this stuff has been a very consistent thread for me for a really long time. But there are lots of other things that I could have started that I could have done. And so I think from my perspective (and I'm curious what what Nathan's perspective is here) saying, “Oh, I need to find the thing that is the most reflective of my personality and going to be my main thing and that I can do for many years,” is actually the wrong way to think about it, because it puts way too much pressure on writing or working on stuff. And you end up just like being like, “Oh, I give up. It's just too hard. And I don't want to pigeonhole myself. I don't want to commit to something that I can't sustain. You just get all these objections that come up. And instead, I would even think about it like, “I want to write one article. What should I write one article about?” Don’t worry about the rest. And this is how we develop in-house newsletters, and we can tell you about how we've done that as well. But just write one article and then write another one. And over time, you will develop something that is very organic to you; something that makes sense, looking backwards, will emerge. But it's not this top down thing where you just decide “Oh, I'm the productivity writer today.” Instead you say, “I'm gonna write one article. Oh, that was cool. I like that. I'll do another one.” I think people just get tripped up thinking that they have to identify these big parts of their personality and write about them; or write about the thing that makes them most unique when just writing and shipping consistently is going to be the thing that will help you discover who you are. There's no substitute for that.

Nathan Baschez: Yep. I totally agree with that. I think that it helps to have some sort of label, but not to worry too much about it, because you can always change it. And the definition of what fits in that label can be pretty expansive, especially once you start to have an audience. I remember there was a moment when Coronavirus was first becoming a crazy thing. And I was like, “how do I write about anything else?,” because we were in the middle of it. I write about strategy. So I was personally interested in understanding the dynamics that would sort of generate a recession from Coronavirus, and how bad the recession might be. And it's, within the realm of business, roughly, it's kind of adjacent, but it's more like economics and markets. But it has implications for strategy. And then there's just this more general thing, which is, I love to take a big question about a complex topic and research it really thoroughly and feel like I kind of understand it, and do my best to explain it in a way that's intuitive and engaging and interesting. I just love doing that. And so, even though technically, it wasn't about strategy, which is what I normally do, it kind of worked. And I think that viewing your marketing label of “strategy” or “productivity” as meaning that's all I can do is a wrong assumption. Another even crazier example happened two weeks ago, Dan, you published an essay that was really beautifully written that took more of an emotional path than anything else. It talked about what it's like to be in a family with a doctor during the height of the Coronavirus pandemic in New York City. It's not really about super organizing, and that's okay. That's not the meat and potatoes of Superorganizers, but you can throw that stuff in there if it moves you, if you have the opportunity to and you don't lose people's trust.

Dan Shipper: Totally, totally. And to add on to that, I think what Nathan said is really important. It's choosing something that’s specific but could be broad enough that you can play around with it, is really interesting. I think one move that I see people making when they are faced with this challenge is to just name it, like Dan's Newsletter, and honestly, Lenny Richardski is the only person that can do that successfully, as far as I'm concerned.

Nathan Baschez: Yeah he's really about product management. It's not called Lenny's PM Newsletter, but it might as well be. It's in a subtitle and he's got a pretty clear...

Dan Shipper: Yeah, But generally, I think some people make that move, like “I don't want to get boxed in, so I'll just make it like about me, and then I'll be able to talk about whatever I want. I think it's a little bit of a mistake. Trying on the constraint is really important both for yourself in giving you a direction, but also from a marketing perspective, so people know what they're going to get. Because if people don't know you already, like no one wants to read Dan's Newsletter. So I would avoid that as a move. But I think the primary way to do this is to lower the stakes for yourself and just write an article.

Stew: Yeah, it's funny, Paul Smolera, who, obviously, you guys work with and who's been adding a lot of value to Compound talks about that theme of just writing each essay on its own. And then every once in a while, zoom out and see the forest if you will. And I thought that was a really powerful example. I think there often can be a lot of advice of really choosing a niche and just like staying in your lane, if you will. So that was a cool emergent way of discovering it. So one thing I'm curious about is when you start to see these themes and start to really nail the stuff you really like to write about, how do you both think about how to create timeless content? You know, when I think of Superorganizers, a lot of that content is kind of evergreen. Or should I do timely content like Nathan's analysis of clubhouse which got a lot of play? Do you guys give much thought about making something that's going to be still relevant in 10 years, or do you focus on current events and adding opinion and commentary? I'm just curious to hear about that aspect of how you write.

How do you think about the lifespan of your writing?

Dan Shipper: Yeah, I'll talk about myself. I started doing Superorganizers without thinking about the fact that it was evergreen, but I think the fact that it is evergreen is kind of nice. And it turns out that one of the problems with evergreen stuff is if it's not timely, it can be hard to grow. If you're writing something evergreen that's not timely and not part of the current conversation, it makes it harder for people to pay attention. how I accidentally got around that was I just did interviews, and I did interviews with people that had audiences, and that helped me grow. So I think the fact that Superorganizers is evergreen is great, but I personally don't spend that much time thinking about it. It was a little bit more focused on quality rather than like the “Evergreen vs. Timely” stuff. But Nathan, what do you think about this?

Nathan Baschez: I think every writer has got to discover their signature move. And once you find it, hopefully you can keep exploiting it and refining it and understanding why it works and doing it again and again. I think if you don't have one yet, then the goal should be to experiment with a lot of different types of moves until you find one that feels sustainable and feels like you could do it on a regular basis, people like it, and you'll grow. When I started Divinations, there was one sort of move that I thought could work. And then it turned out, it was a totally different kind of move. I figured that out three months in, and the growth was just totally inflected, and it's very obvious in the graphs of Divinations where that point is -- when I started writing in a different way. And I think if there's one thing that would have accelerated me finding that signature move, it would have been A) potentially focusing more on just what I wanted to do rather than what felt strategic or, trying to define too much of a framework upfront, and then B) just being a little more experimental, if it felt at some level that something wasn't working, just giving myself permission to try something different for one week. I think I waited a little too long to do that. But in the end, it worked out. It only took three months. It was a fairly good process, and you're not going to find that out after publishing one thing. You'll find it out on the fifth thing when you feel like, “I just really don't want to do this anymore.” That's when you know. And so I think it basically works. But the key is to find that signature move. And so, for me, it was like, okay, there's something that tech Twitter is talking about, like a new company, or a company that launched a new thing or, something kind of timely, and there's elements of it that are complex. And there are basic questions around it, such as, “Will it work? Who is it for? Why would it work? What does using this example teach us about broader concepts about why some businesses succeed and others don't, or why businesses grow to become really powerful and others don't?” There are patterns, and those patterns have been studied in business school. It's not a science, but it's hopefully on the road to it. That's a personal project of mine -- to make business stuff less like alchemy and more like chemistry. And I found the two moves that have worked for me are 1) analyzing something that's like going on in tech Twitter because that's on people's minds, that people are thinking about that's an active conversation and, and bring to that analysis frameworks from the business school literature. And then the other move is 2) to actually just dive into the business school literature on this stuff, and try and really deeply understand it and just explain it in a way so that the reader doesn’t have to do all of that diving, but you get the benefit of it. And I think it really helps that there's two moves, and one is a more natural fit for paying, which is the explainer ( because it is essentially business school stuff), while one is good for free growth, which is commenting on timely discussions. But that's not the only way to do it. There's lots there's different ways

Dan Shipper:I was just gonna say, what that made me think of is that we're very metrics driven. We have a meeting every Monday where we see how much we've grown each week, and then we try to figure out what worked and what didn't. So we're thinking about this business and we want to grow it as a business. But there's this weird art thing that we do - we say that this has to be a reflection of you as a person and your soul and what makes you tick and makes you excited and makes you want to lean in. The minute you're phoning it in and just doing it because you feel like you have to, or you feel like it's the right thing to do, is the minute the content isn't any good. And, and I think that finding your signature move is so right. It's finding the thing that really makes you come alive. And when you find that, other people will notice. But don’t do it in a way that raises the stakes where it's like, “I need to find the thing that reflects my soul.” We know that this is a kind of art. And the way that we express that is just by experimenting a lot and in a low stakes way until we find the thing that really hits and resonates, and then we just do that over and over and over again.

Stew: I think that's a perfect segway into something you said earlier, when we were thinking about what's really worth covering, You're putting your ideas out there. It seems like a big gamble or a big risk or you don't want to sound like an idiot. So I’m curious to hear from both of you -- and Dan, maybe you can start -- about the psychology of getting more comfortable with sharing your ideas online. Given that what I'm hearing you both say is to play with it. Put stuff out there. Do it. Write about the stuff that you're going to really be interested in and intrinsically enjoy, and then see what sticks and double down on that. So it's not this terribly strategic approach where I'm only going to write about this market and that's my thing, and I'll do it no matter what. There does seem to be a more playful approach where you just try stuff out. So I'm just curious to hear what's worked for you all and how you've gotten more comfortable just taking more shots on goal.

Dan Shipper: Yeah, I think it's really important when you sit down to write or sit down to push publish, to really listen to the objections that come up, because your inner psyche is going to throw up a bunch of objections like, “this isn't any good,” or “I don't want to be pigeonholed” or “what if people don't like it?” or “what if they will get mad at me.” There's going to be a bunch of stuff, and the way that you overcome that stuff is going to be different depending on what kind of objections come up. So for me, I definitely have that “I don't want to be a productivity guy. Like, what if that’s all I am, you know?” And so some of the things that worked for me is thinking about this as a learning experience or an experiment. Especially in the beginning, separating myself from the actual results of the thing, like how many people read it or that kind of stuff and really focusing very, very hard on the process. Really being less focused on the quality or any of the outcomes tends to help a lot. Because those are the things that can get super judgmental and super self-critical about. And those judgments end up stopping you from doing anything which is the worst possible outcome. The best outcome is, “I do great stuff.” The second best outcome is “I do bad stuff regularly.” And if you do bad stuff regularly, you will eventually do great stuff.

Nathan Baschez: The thing I'd add to that is this classic thing, every single creative field has a version of this thing. And the best articulation of it, I've heard is from Ira Glass, where he's talking about how the reason why you're motivated to start to do something like this is because you love it, and you have great taste, and you can really appreciate a lot of nuances in the craft. Then you start to do it, and you accurately assess that your stuff does not measure up. That feels bad, right? But the answer to that question is not to stop doing it, Because your first draft is not a test of your ultimate potential. It's just the first step, So the hard part is to keep going anyway. That's why it's so useful to do this thing that Dan is suggesting, which is to hold your nose and press publish on a regular basis.

Get feedback from generous readers, from friends, from anyone you can, and just talk to them about your writing. Think about your writing and make it better, but above all else, ship. it's really, really important to hold yourself accountable to your inputs, rather than your results, in the early days. Then once you're shipping regularly and you’re extremely confident that you publish a thing or two every week, then, at that point, let's start looking at the metrics every week and talk about the story that the numbers are telling us this week. That's a little bit more useful later on.

Dan Shipper: Yeah, and to add on to that, that word publish is very loaded for a lot of people. You have this image of yourself with your hand finger hovering over the keyboard and the wind starts blowing and lightning flashes and then you press publish, and the entire world looks at it and laughs at you. That's one of those things that makes you not publish or not write at all. Another way to think about it is to lower the stakes for that word. What's really important about writing early on is that feedback loop that you get from people, but you don't have to get that feedback loop necessarily by publishing into the entire world. So other things that I've seen people do successfully is first, just like start with a couple friends and put them on a private newsletter, or just send them an email, don't even think of it as a newsletter. Send an email once a week with some thoughts to your friends -- that's how Brain Picking started -- and there are all of these techniques. If you notice, for example, that publishing feels threatening, you can do something that is kind of like publishing and gets you most of the benefits of it, without it being scary. Just use that as a way to do it.

Nathan Baschez: The great Matt Mullenweg quote related to this is “usage is oxygen for ideas.” And I think consumption of content is oxygen for you to keep creating more content. Because ultimately, it's an act of communication, right? And so you just need to run your thoughts that you created through someone else's brain and see what they thought of it. Right? That's ultimately what you want. it's about finding some early readers, even if it's private, or even if it's just friends. That's what Compound is great for.

Stew: I know, there's just enough social accountability to where if 20 other people ship a draft in a week, you know, you feel that pressure to do the same, and you have that early reader base built in. I love Dan’s suggestion to start sending an email to 100 people you know, I mean, you can start with five, but I threw something up on my Facebook, “hey, I'll send an email each week” to do exactly what Dan just said, just shipped something. And I just found that to be such a great low-stakes way of getting comfortable. And then certainly with Compound, it's the same deal. We're trying to get you five guaranteed readers up front. They'll beat it up. If you really had anything that was amiss, at least it's caught then. And then you really have the confidence and the support to get in front of a broader audience.

I think that's fantastic advice. So one thing I'm curious about -- I think a lot of folks on the call already have email lists and have an audience. But a lot of people are just getting started. And maybe they have developed a habit of publishing but are still thinking “how the heck do I get a few thousand subscribers to my list?” I'm just curious. That might be a tad open-ended, but I'm just curious to know how you all have thought about just growing the list fundamentally. How do you drive people to the Substack to get their email and get a relationship started? And then I think if you're open to it, Nathan, you mentioned that you’d be willing to share some of the stats from the last few months of how you guys have grown and what's worked. I just want to leave the group with some really practical ideas of what they can do to grow their own audiences.

How do you grow your subscriber base?

Nathan Baschez: Yeah, totally. It's important to separate out the mechanical things that are necessary, but not sufficient, from the stuff that really drives it. The way that we thought about it is there's sort of your core engines, and then there's drag on that engine. It's like a car that's not particularly aerodynamic. And so the mechanical things you can do to screw that up, vary from publishing on a website that literally doesn't have an email call-to-action anywhere -- and that doesn't mean that you need to shove it in people's face all the time -- that's actually adds drag. But you just have to collect emails or Twitter followers or whatever like you. There's got to be some mechanism to accumulate an audience and again, that's actually not so important, really early on. But if you're really starting to ship regularly and you like it, especially if you have ambition to turn it into a business, then that becomes one of those mechanical things that's important. Mechanically, it's important to ship at least once a week at minimum. We could probably get away with less, but it just becomes a lot harder. Other sources of drag include if your newsletter has titles, like My Newsletter Edition Number 31. That's not really a very shareable title. So if you look at the way that it shows up, if someone were to tweet the link, -- it should be a little hint at the sort of value you get from reading this thing. My Newsletter Edition Number 31 does not do that. But that's all drag. Sources of actual energy/engines that will propel you forward are speaking the stuff that is really interesting to you or important to you or is emotional. For the kind of writing I do, I think about it like, “Is this surprising? Is this important? Is this true? And is this relevant?” This is my main framework for doing stuff. Just to break down like a recent piece -- the Apple Health one did better than I expected because it wasn't a conversation that people were having like Clubhouse it was one of those like, I thought it would probably do well, because everyone was -- like Clubhouse, everyone was starting to talk about Clubhouse and ask the questions, “What is Clubhouse?” so I felt like I could write a post that answers that. With Apple Health, no one was really talking about it. It was a collaboration with this guy named Rob Litters, who's amazing. A lot of it was really driven by his ideas, but then I put together some of the business school, strategy/theory side of things. So we came up with something that neither of us could have written on our own. And I think the reason why it worked, was it basically became the most viewed post ever on Divinations, maybe Copass beat it, but it's at least number two, if not number one. And the reason why is if you go down that list, surprising -- if you read the post the implications of what Apple is doing, most people aren't aware of it. Important -- well, the thing that Apple is building would be like crazy if it existed. True -- It feels true when you read it, and then you talk to people in healthcare, and they're like “Oh, yeah, I thought everyone already knew that.” No, people don't know this. It's crazy. Getting back to the surprising point, and then relevance. This is the part about the public conversation thing. It wasn't relevant to the stuff that people were tweeting about that week, but generally, people are super interested in these themes -- Apple and the way that value chains evolve over time, if you're kind of a strategy nerd. There's a lot of stuff there that's relevant on the order of years rather than weeks, and so it was still keyed into something pretty relevant.

Dan Shipper: Yeah. And I think to get into the engines a little bit more, one of the things that we've noticed in building this over the last six months or so is there's a big difference between the stuff that we write, the stuff that good newsletters do, and the stuff that other types of publications do. Not to say that one is necessarily better or worse, but they're just different. So the stuff that you might read on an ad-supported, general reader-type, website, even stuff related to productivity or strategy, is going to feel pretty high level. It's almost like if you ask a person at a call center to explain to you productivity. You would get an almost scripted, high-level thing where it's someone trying to give you the very basics and get you to nod your head and then go. That makes sense because their business model is to essentially drive traffic and ad revenue. What we try to do is make you feel like you're sitting down to dinner with a really smart friend who knows a lot about productivity or strategy. And we try to go really detailed, like really long-form about stuff that we feel passionately about and that works.

I think more tactically, there are a couple of different things that have worked for us. For example, the interview model works really well. And I would extend that to involving other people in your newsletter. That works really well. So for me, I interviewed someone every week. Often that person has an audience, and in the interview, they get to share all this stuff that they've never gotten to share before. And so I have this built-in growth engine where every single week someone is tweeting it out. And often those people have lists or they have Twitter followings or whatever. So you just stack that growth week after week after week, and that's really great. And you can climb the ladder of influence. So the people I interview now are far different and more famous than the people that I could interview at the beginning. But you can do that in a lot of other ways. Nathan mentioned that he co-wrote articles. You can co-write articles with people and have them bring their audiences. You can do link sharing. There's just a lot of tactical things that you can do to get growth aside from just writing quality stuff, which is obviously the core. Something that Nathan's done successfully that we've already mentioned is l just writing up timely stuff and helping to push that and push the conversation forward about timely things and being a part of that conversation and even having the conversation on our platform. Nathan wrote a really great article about the bull case for Quibi when no one else was, everyone else was just completely demeaning Kwibi in the news, and they threw out a bull case, which was amazing. And what happened was not...

Nathan Baschez: Currently, but you know, yeah, they sold it, then they got $27 billion from SoftBank and can bail me out.

Dan Shipper: We'll see. We'll see. It’s an unfolding story, but the point is, what happened is that the Head of Product at Quibi then came in and interacted on Divinations and had a conversation, which he never would have done if Nathan had just written another takedown. So I think one thing that we try to do is like be the center of conversation if we can, which means being even-handed to people as much as we can. And finally, I would be remiss if I didn't say this, Hacker News has been a really great audience driver for both of us. And I don't have any tips for you other than be sure to submit early in the morning with a catchy title, cover productivity or strategy, and if it doesn't work the first time, submit a couple times, because sometimes it gets picked up. But that has really worked well. You might get like 50 or 70,000 people to read it, but most of them will just bounce without reading it. So you're not going to get a ton of new subscribers, as much as you might think, but it still is a really good source of growth. Maybe I would broaden that point to say, find communities of people that are into what you're into and make sure that you're sharing with them regularly.

Stew: Totally. Speaking of which, we're going to do a Q&A. So everybody, if you've got questions, type them into the Q&A box. So I was going to start. I think Steve had a couple questions. I am going to upgrade him to a panelist here.

Steve: Hey, guys. Yeah. Good to see you, Dan. Thanks for chatting again.

What was the most unexpected thing you learned from starting a newsletter that you didn't see coming?

Dan Shipper: How profitable it is and how quickly it can grow.

Steve: And I got a second question for you. If you could go back in time and talk to yourself before you started this, what advice would you give yourself in retrospect?

Dan Shipper: Start earlier. Yeah, I think this has been a really surprising journey for me because, coming from the tech world, it's not something that you expect to grow like this. This is our graph [screen share]. We started in December and now we're at almost $250,000 a month. Not at month -- a year -- in revenue. And that's just not something that I ever thought was possible with just writing online. And writing has been kind of a passion for me for a really, really long time. And I never expected to find something that would grow like this, to do something that I liked so much. So, yeah, I don't know, Nathan, what do you think?

Nathan Baschez: Yeah, I think it's the same thing. It's a little different for me, because I knew this when I was at Substack, I saw people do versions of this a lot. But I alway thought, “Oh, they already had a huge audience and it took them years.” Having an audience already definitely helps but you can get it going pretty quickly, when you're really consistent about it. And the hard thing is being really consistent about it. It requires being pretty much full-time on it. And being full-time on it requires a lot of confidence that it's the right thing to do. And then, some way to get paid -- either by someone else or by yourself. And that's a very hard sort of chicken and egg thing to do. So there's that. Also for fun, I can show on the Divinations graph, it'll show you the inflection point where I started, I figured out the move that worked, and then the list started growing a lot faster. The metrics are a little bit messed up, because when we merged our publications temporarily, we subscribed everyone to everything. And we're like, no, we don't want people who actually had signed up for our newsletters. But anyway, right around here, you can see this was the early part. It was growing, Okay, it's kind of growing. And then right around here, I started publishing different kinds of stuff. And it just took off in this totally different way. So it's pretty clear in retrospect that there is a phase change here.

Steve: I was gonna say I have one last question.

What is the one thing you've picked up about writing along the way -- like the day-to-day craft?

Nathan Baschez: I tweeted yesterday about how sequencing ideas is so hard, and asked if people had tips. It was really funny, because there are a lot of people -- I looked at their Twitter profile -- and they didn't publish that much and they very confidently told me I just needed to do something really obvious. You know, make an outline, or whatever. I tried that. But it's still hard. I think maybe one thing I've learned is that, at least for me, so far, it hasn't felt a lot easier. It's still really hard every time. I write, I can design stuff, and I can write code -- these are sort of my main three skills. You can include product management type stuff in there. Writing is by far the hardest when you're trying to do something that explains something complex, and also entertains people. It's really hard. I'm not expecting it to feel very different years from now. We'll see. My goal now is to talk to more people who have done this for longer and see how it evolves. But so far, everyone I've talked to who has been doing it for a lot longer than me, says basically, it's hard. It just sucks. Get used to it. So, embracing that. It’s like working out or whatever. There's a lot of things in life that are really beneficial to do but never end up feeling easier.

Dan Shipper: Here's one little thing that we picked up. And this is mostly from our editor, Paul. Write short. So we had a lot of pieces where we were really struggling to figure out how to frame things. We had so much we wanted to say and there's just so much here and we don't know where we’re going with it and all that kind of stuff. And the solution is actually to just do a short version. Write 500 words and make it a good 500 words, hopefully. And then if you need to make it longer, make it longer. If you're struggling to write and struggling to write consistently, start by just writing short pieces, and then and then make it longer if you need to.

Nathan Baschez: That does really help. Yeah.

Stew: Fantastic, guys. So Jess, I'm gonna turn you on here. I think you have a question around fiction as a genre. And if that's something that you guys have thought about, I know, Dan, you've been interested in writing fiction. So Jess, I don't know if you're with us, but feel free to unmute and elaborate if you'd like.

Jess: Sure. So this is actually more of a question on behalf of my sister. She has her master's in creative writing, and she is a prolific writer. I don't say that just as her sister. But I've also thought of writing in a serial fashion because I always think about writing a novel, but it seems like such a large undertaking. So I was thinking, you know, of shipping chapters as a way of writing a novel. And it seems like a newsletter would be a great way to keep yourself accountable, and what you all said earlier about just getting it out there and not overthinking it. I was the one that said analysis paralysis is what gets you every time. What do you think of newsletters as it pertains to fiction and serial fiction?

Nathan Baschez: Yeah, I mean, so I can definitely answer. Also, Dan is actually writing a novel.

Dan Shipper: Let's talk about it. So I've been writing a novel for like two and a half years and am on my fourth draft, and obviously, none of it is released. And, yeah, it's a really big undertaking. And the only way that I was able to just continue doing this is just like, because I just really like it. And I'm not really thinking too much about the magnitude of it or what I'm trying to achieve. I'm just trying to consistently make progress on it. And for a long time, I was running it in a vacuum. And I think that was a little bit of a mistake. And, yeah, I'm on my fourth draft. And each draft has almost been like a different book. And so it was a little bit difficult for me to write it in serial fashion because if I write it serially, then make a mistake in the first chapter, I won't be able to go back, revise it, and I want to have the whole complete thing. At the very beginning, I almost did it as a serial kind of open source book. And I can't remember exactly what you said Nathan, but you definitely convinced me not to do that. You're like, don't do that. Then I kind of got in my head about it. I don't think it was necessarily a mistake, because at the time I was such a bad fiction writer.

If I could go back, I would probably just write it in public or write it in like a semi public way where I had friends reading it and all that kind of stuff. You just have to do it in a way that protects your ego so that you don't get demotivated. Do it with people who will be supportive. Like my friend, my friend Alex is like, I loved showing him my early drafts because he was always 100% supportive no matter what. And that's what I needed because I was writing really bad stuff. And yeah, so anyway, I don't know if this is helpful, I would totally consider doing a serialized fiction newsletter. I'm not sure. There are some examples of that, like Andy Weir, who wrote the Martian did this. Historically, a lot of novels were written that way, like in the early 1900s. I don't know of a ton of popular fiction newsletters currently. I've seen people try.

Jess: Twilight started out as fanfiction in serial fashion. I didn't know that. Yeah. And my sister has won awards for her writing. So it's not even that this is like a dream that she's having it's coming to fruition, she's worked her whole life towards it. I think it's a matter of getting it out for more people to see and seeing that she can, you know, take the mindset of startup, which I'm from the digital world, that's been where, you know, working for startups and, and SaaS companies, and translating that into her world. And that's where the question came from, and why I encouraged her to be here. So I think this is really helpful. So thank you for that. Thank you for sharing. I'm glad you actually had the direct experience. So it's great.

Dan Shipper: Yeah, we're sending our best to her. I hope she's feeling a little better.

Jess: She's listening so she's heard it firsthand. So thank you. Her name's Annie.

Nathan Baschez: I'm excited to read more of Annie stuff and look it up. I think it's especially great if you already have an audience and a world you're building. Characters who you just want to keep hanging out with. I think a serial newsletter that just expands on that world a little bit every week would just kill. It's seriously underrated. It’s such a better business model than selling books just in terms of creating stability, right, like through subscriptions where you have a predictable amount of revenue that's growing somewhat predictably. It's just such a great foundation to build on. And I remember what I told Dan, back in the day, which was like, our instincts are around software, where you just ship it really early when it's really embarrassing, and then you keep improving it over time. And it works because software is the kind of thing that you use over and over and over again, because it's like a tool, but a story is like, you go through it once and like you're not going to read it again, probably when it's better. And so I think it really works if you have characters going through new stuff all the time. Maye one specific plotline is not that big of a deal, but it's more a world and its people and especially for people who comment about who those people are and why people care and like what their world is and what kinds of situations they go through. And like, you can think of a bunch of ideas. But also in retrospect, yeah, I probably should have just said like ship anyway. But it was just it felt like there was a very specific plot that was very important to Dan that he was like, wanting to really craft that plotline. And I think that's the thing that's harder to do in this sort of iterative ongoing basis.

Dan Shipper: The other thing that I think motivates a lot of authors is seeing the book in a bookstore with Random House on it.There's this real romantic appeal to that. And it's part of the reason why people write, and you definitely lose that doing this and that's just like a trade off that you have to accept I guess, I mean, maybe if it does really well, you'll still get bought by Random House but it’s not the traditional path. You have to be willing to just kind of jump off the traditional path and do something new that I think will probably be more common over the next 10 years, but isn't something that people are doing right now.

Stew: Awesome. Great question. Thanks, Jess. And Annie, hope you're feeling better. The next question comes from Megan. And it's around kind of the switch between free content and paid content and how you guys may think about that funnel or what should be gated and what shouldn't.

Megan: Yeah, thank you. For those of us who've been accustomed to doing a lot of free content marketing or have a number of articles out there, that people are, you know, pretty familiar with getting access to, without paying, do you have any tips on making that transition and kind of when and how to start Launching that subscription feature.

How do you make the transition to paid?

Nathan Baschez: Yeah, I mean, what we did is we basically just flipped the switch and then figured it out after we flipped the switch.

And I don't know if that's the optimal way, but I think it basically works. It's really hard to figure out ahead of time.

Dan Shipper: Yeah, I'm curious: are you worried like that if you have a free audience that expects something that they'll get angry at you putting it behind a paywall? Or is it more of a tactical question in what should be behind the paywall?

Megan: Both good questions could be part one, part two, but more the former. It sounds like what you're saying is build the audience and then risk losing them potentially when you make that switch and not worry about it rather than you know launch something that's paid from day one or you know try to continue to cater to an audience in a certain way long term. I guess the second question it could be part of the answer right is just being very diligent about selecting which pieces are free and which are not

Dan Shipper: Yeah, that’s actually what I did for Superorganizers. So I just turned on paid for Superorganizers and didn't announce it. I didn’t even paywall anything, I just turned it on, and people just started paying for it. And I was like, well, this is cool.

Dan Shipper: Then I locked the archives. And so there was now like a couple free posts. And then the rest of the old interviews were all locked, and people kept paying for it. I kept writing the free stuff, but then I would layer in some paid posts, like in addition to the free stuff. And then I would send out to the free list like, Hey, here's a paid post that like you can read if you pay. So I just built it organically rather than having to have this moment where I’m going paid and have to risk people getting angry at me. It was just like, flip the switch, lock the archives, write some paid posts and see what happens and there's a bunch of things that you can do like that that will allow you to experiment with it without potentially risking your free customers.

Megan: Thank you. Yeah, I'm not publishing on Substack yet. Any tips on pricing? Do you get to set your own pricing?

Nathan Baschez: Yeah, on substack you set your own pricing. A lot of the kind of more personal and entertainment newsletters charge in the neighborhood of five to ten bucks a month. And then the more work relevant newsletters are maybe like 10 to 15. Sometimes they’re a lot more like there's one that's very specialized on the bankruptcy industry, appealing to bankruptcy lawyers and it costs $40 a month. So it depends on the market and the use case. But yeah, that's like roughly sort of what the market has settled around. It's very early though. It's not like it's a figured out thing.

Stew: Sure. Awesome. Thanks, Megan. So actually, I think Jose had a question around, kind of where to find these early audience members. You mentioned Hacker News is a really effective kind of growth channel where a lot of your readers are hanging out. So let me, Jose, if you're available, I'll promote you here. And feel free to unmute and elaborate.

Jose: Hey, great. Thanks. Thank you guys for being here. Yeah, so I've got two questions ready to go. So one is, what's your process for finding active communities. And just to be a bit more specific here, we can always be a bit lucky if we find a good channel, like maybe post on Hacker News. And we might be lucky. But do you have any process for how you do this? And the second one is, how do you build relationships with early adopters to help that grow?

Dan Shipper: I wish that we were more scientific about this. And I think we'll probably have to be over time but we're just doing stuff, basically. We're just making stuff we like.

Nathan Baschez: All of our energy and scientific thinking and systems has gone into what kind of stuff to write. After that, we just chuck it onto Twitter and post it to Hacker News or whatever. Distribution has been very unscientific.

Dan Shipper: I would say like if you want to be systematic -- and the reason that works is because like we are writing about stuff that we care about, so we're already part of those communities. So we don't have to go search for a community. But if you want it to, I would just Google, like, go on Reddit, like Google for it, you'll find a dozen, whatever it is, if it's like lawn care, like there's a dozen like lawn care sites, there's a dozen, like lawn care subreddits. And it's not going to be as well formed to the community, probably as Hacker News is just for tech nerds. But like, that's the thing.

Nathan Baschez: Sorry, one other really quick tip is being a really good member of those communities, supporting other people's work, replying to things that other people are doing with care and giving people real quality of attention is I think, actually really important and I realized like, that's something I think that Dan and I, both on that have helped is like, we're a part of these sort of communities on the Internet and on Twitter, and I use community in like the lowercase sense. People roughly in our universe on Twitter that we just reply to and joke with and dm. And that's organic, we’re just making friends, you know?

Dan Shipper: Yeah. And in terms of your second question around how do we nurture that early community..we're not doing this as much anymore, but I think we should probably restart. For a while, anytime anyone signed up for a paid plan, we emailed them and said, “Hey, do you want to do coaching?” And I'll do a 30 minute, one-on-one productivity coaching session with you. I met so many readers that way. And it was really fun. I think it was fun for them and gave them a lot of value in their subscription, right off the bat. And then it just gave me a ton of stuff to write about. Every time I had one of those conversations, I had a bunch of ideas for what I wanted to write about next. So it's a really, really positive thing to do to make a point to reach out to people that are subscribing.

Jose: Okay, now that's really interesting. Just as a quick follow up related to this, which I think is very, very tightly tied to it, do you guys follow any process where you guys just knew you had cracked the format? Or how specific your content was going to be? Or was it more like something that you were improvising and it just felt right?

Dan Shipper: Yeah, it's been different for both of us. So for me Superorganizers has been roughly the same since I started. The interview model and the way I write interviews has changed in little ways but the broad strokes are the same and then I layered in the paid stuff on top of it. And then Nathan I think basically started with the interview model and then flipped to something else that worked way better for him.

Jose: Okay, cool. Thanks guys.

Stew: Cool. You guys want to rip through the open q&a questions? We got some in the chat. Maybe we could do right after?

Nathan Baschez, Dan Shipper: Yeah, yep.

Stew: Awesome. So I think we'll start with Corina’s then, which is, “I have a question on writing articles. I'm really interested in how you weigh up writing more frequently versus publishing less frequent, but longer and more in depth articles.” So to reiterate, how do you think about being prolific versus making these more polished pieces.

How do you think about writing frequency?

Nathan Baschez: Yeah, we've kind of vacillated on this. And we've done both at times. And I don't know how much it matters. I think you can do either and be successful. And I don't even know if you really have to pick. You could do short stuff most of the time, but occasionally throw up a really long post, or do long stuff most of the time, but occasionally do a really short thing. And I think it's more important to just find something that works for you and that works for your audience. Certainly if you write a long thing, it could take longer and if you're waiting two months to publish something and you publish four things a year or whatever, that's probably not enough. But yeah, I think that there's a lot of variations within this deck of work.

Dan Shipper: Definitely, I mean, what we've tried to do is, write one long thing a week and then write a couple of short things a week. We've not really been able to fully do that all the time, but that's what we shoot for. But other people, like Bern Hobart or Ben Thompson, they just write four days a week. And whatever I get out, usually like 1000 to 1500 words. But yeah, I think it's about finding what works for you, for sure.

Nathan Baschez: I think that the longer things tend to get shared around more, and the shorter things are maybe a little bit of a better email experience. When you're trying to swat away emails, you can go, “oh, this will be good, and it won't take that long, so I'll just read it right now.”

Dan Shipper: Yeah, the longer things are also better paid stuff. People feel better about paying for like a big, long article than they do about paying for a 500 word article.

Stew: Awesome. Yeah, that's great advice. So I'm curious, actually, Dan, you just kind of touched on this, especially early on, did you interview your readers to shape the direction of your newsletters? So kind of hand-to-hand combat with early readers? How influential was that in deciding what you wrote about next?

Dan Shipper: 100% although I didn't start doing it until I went paid, so that was about six months into Superorganizers. I hadn't really been publishing regularly on Superorganizers. I did a couple posts a month from August to December. And then I started to take it seriously. But yeah, once I went paid, like I tried to interview every single person that signed up. We also do surveys and that kind of stuff to see how people are feeling about the newsletter.

Stew: I'm just curious, did it shape the direction of what you maybe doubled down on or cut out? To resonate with folks?

Dan Shipper: Yes, There's a bunch of different sub-communities inside of Superorganizers. I have a much clearer conception of the types of people that subscribe. And then I try to make sure that the content mix hits the different topics that those different types of communities care about, even though they're all under the Superorganizers productivity umbrella. There's a bunch of people that have different needs. And so it helps me to figure out where to go.

Stew: That's awesome. Cool. So Sara Campbell had a question around building on Substack. “Are you planning to build a more robust homepage, especially with you guys doing kind of the bundling approach, so that people can kind of go through the archive a bit more easily? How do you kind of think about, long term, the hub for you guys?”

Will you stay on Substack?

Nathan Baschez: Yeah, I mean, we're not really a technology company. We're a media company. So we want to stay on Substack as long as it works. Also, you know, it sort of depends on Substack’s direction. There's a world where it doesn't meet our needs anymore because they want to go more in a YouTube-y type direction almost, where there's not a lot of flexibility or customization. But if they go in a more Shopify-y kind of direction, where it's more powerful, and there's API's and all that kind of stuff, then we could potentially stay. It's just a question of pragmatism on what does it take to make this sort of bundle work? And right now, it works on Substack. So we're thrilled to be on it. We love Substack. And we'll see where it evolves from there. But yeah, I mean, we'd love to make it easier to discover past issues more easily. The way we solve for that now is in the weekly digest that goes out on Sunday mornings. We just always highlight some stuff from the archives because so much of it is pretty evergreen. So that's one thing we do.

Stew: Awesome. Cool. So the next question, “What did you already have in place before reaching out to your initial audiences, like kind of just the raw materials that you all had in place before you really launched Superorganizers, launched Divinations? What are the table stakes for starting to build an audience?”

Dan Shipper: Nothing.

wNathan Baschez: I mean basically nothing. Dan has written a lot of stuff that has done really well over the years. I have to a lesser extent published some stuff on the internet. You know, we had a really interesting set of life experiences, I would say. We did a lot of reading and you know, my time at Gimlet and Substack. And building products has shaped a lot of my opinions. We had all that kind of stuff. What did you mean by nothing, Dan?

Dan Shipper: Yeah, I guess what I was trying to say is, yeah, obviously we've done a bunch of stuff before that. But I didn't spend any time preparing four different posts or writing a manifesto about what Superorganizers was, I just did an interview and wrote the interview and then published it. I was like, I'll figure out the rest later. So basically, I don't know where that question was coming from, but sometimes there's a temptation to do a bunch of preparation before you do the thing. And usually, the preparation is wasted. Preparation is great when you know exactly what you're doing. Basically, the most important thing is shipping an article rather than preparing to ship or preparing to start the newsletter or whatever. Just do the article.

Stew: Totally. Awesome. Cool. So Alberto says “Both your newsletter strike me as highly educational. So you kind of get introduced, especially in a lot of Nathan's stuff, there's some foundational concepts and theories that are then called back on later. So is that intentional? Do you have this almost narrative you're crafting throughout these pieces?” And then just generally, “How do you think about introducing these concepts and theories throughout your work?”

Nathan Baschez: Yeah, I think it's definitely intentional. I think it really helps to have a worldview that you sort of develop. I haven't introduced any new ideas and strategy, I just try to understand the ideas that are out there and then apply them to new stuff that comes up. Maybe one day some original thing will occur to me. And until that happens, I'm very happy to just apply stuff that other people have come up with and use it that way. I think the basic job of a columnist is to have a model of the world and then run current events through that model, and spit out some analysis or explanation of those events. It's a little bit different, I think, for Superorganizers, because it's not current events, but you still have a model of how productivity works, and there's fundamental concepts. Then you can interview people and each person is almost like the Superorganizers equivalent of an event. But you can even talk more about that.

Dan Shipper: Yeah, I mean, what I try to do is take a pretty unbiased view for the interviews where I'm literally putting out what people do. And then at the top of the interview, I'll usually have a little bit of my thoughts on why this is interesting or important. And then for the paid stuff, I have some models for how to think about productivity. And I'm not responding to current events, I’m just responding to whatever is top of mind for me, and then talking about those models and applying them to different situations, all that kind of stuff.

Stew: Awesome. So I just had another question. “Are you seeking out the people to add to the bundle? Are they approaching you?” So, how much outbound are you doing and how much just magnetic force is coming on you via Twitter and Substack?

Nathan Baschez: It's all inbound. We’re just swatting people away. We can't keep up with it. Haha, just kidding. It’s both. It’s both

Stew: Yeah, that actually ties in well. There's one question that is still floating around in the chat, which is, “What is the ratio of your time spent writing versus your time spent promoting?” Because I think that's something that a lot of people overlook. You're not only a writer, but you're a marketer, a digital strategist. You have a lot of other hats you have to wear. So how do you think about that ratio of producing the work but also making sure you're promoting it.

What is the ratio of your time spent writing versus your time spent promoting?

Dan Shipper: I wouldn’t say we spend that much time promoting stuff. But we do spend a lot of time doing things that are not writing because we're building an organization where you bundle in more writers, we're hiring writers, we're doing a bunch of stuff. And so that takes up a lot of time. But it's not really a promoting-versus-writing thing. It's like a writing-versus-creating-the-organization-to-make-more-writing thing and it depends on the week. I think usually I'll spend a day or two a week writing and then the rest of the time doing other stuff.

Stew: Cool. Oh, my goodness, I think we're down to our final two. Ethan is curious about your individual approach for reading other newsletters consistently each week and a few other paid newsletters that you're subscribed to. So who are some of the writers that you guys really liked reading? Have they been a good source of inspiration? You've probably already partnered with a couple of them. Do you guys look at them consistently each week?

Who are your favorite writers?

Nathan Baschez: So obviously, Ben Thompson is obviously the GOAT of my world. I love a lot of writers. Some publish less frequently like Kevin Kwok published a really awesome thing on Figma this week that I have yet to dive into but, the outside of it looks amazing. Then there's Brian Hobart who's publishing all the time and is awesome. There's great podcasts. I love Dithering, I love Invest like the Best. It's all the stuff you'd probably expect and then also I think it's really important to dip into stuff that's more straight. I love Slate Star Codex. There’s too many to mention. And it's a little bit chaotic. I don't have a super intentional approach. I just indulge my curiosity and hopefully something good will come from that.

Dan Shipper: Same thing. I just read a ton of different stuff, including a lot of the people that Nathan mentioned. Two other people that I read a lot are Poina Arinova and Web Smith. I actually just read Web today. Definitely recommend those two people.

Stew: Cool. So final question. Brian asked, “how do you decide on people to interview or even cross promote?” So how do you think about the folks that you feature who are likely to share their respective audiences? And then, “what if they are initially kind of apprehensive on a fairly new blog?” So Dan, you mentioned that it's tough to get those early people but once you do, you can kind of climate change, and you got Seth Godin as somebody in Superorganizers. So how do you think about picking people to interview and getting them convinced to take the call.

How do you decide on people to interview or even cross promote?

Dan Shipper: As with most things, it's not very scientific on the thinking about who to interview. I just found a bunch of people that I thought were successful and - I'm like this. I do a lot of the nerdy productivity stuff - so I had a list of people that I knew were doing stuff that I personally knew. And so those are the people that I started with.

There's this guy, Cesar, which is in the first Superorganizers article I wrote. And I just knew him from college. And I knew he was this crazy guy who had been running his own personal encyclopedia for six years or seven years. And so when I needed to interview people, he was the first person I thought of. So basically, I just started with my friends, or people that I was, acquainted with. And then those articles did well, so I gained a little bit of audience and that gave me permission to get intros to people I didn't quite know but were slightly above my friends in terms of audience and status. And then I got to interview them, those interviews did well and then I just climbed up from there. And then in terms of mix, I do a lot of interviews. I've done probably 50 or 60 or something interviews and I've only released 20 or 30. So there's a lot of interviews that I have in the can that either just didn't work or weren't interesting enough, or I just haven't had time to release yet. So I cast a pretty wide net, and I'm pretty open to spending an hour with pretty much - well not at this point, not anyone - but very early on, almost anyone. And then over time you tune your eye to people who are really interesting. There's a lot of times where, on Twitter, I'll just see someone talking about their productivity hack, and I'll be like, “oh, that person be great. And then I just DM them.” That's a good way to do it.

Stew: Awesome. I'll let this one tangential question slide in here, or as a follow up question. “If someone's not doing this full time and they want to do an interview - what takes the most time in an interview? Do you have any advice on how to be somewhat efficient?”

How do you conduct interviews?

Dan Shipper: The most time consuming thing about interviews is writing. Conducting the interview is pretty simple. You just ask questions. I mean, sometimes you might have to do research beforehand, but writing the interview is really hard. It's deceptively hard. So if you read a Superorganizers interview, it's like 3000 words. It reads in the person's voice. But actually, if you look at the transcript of a Superorganizers interview, and look at the finished product, they're completely different. And I'm basically rewriting what they said in their own words, but in a way that reads well and has a narrative arc and has all this stuff that makes it feel like an essay written in the first person. And that is actually really, really hard to do. Because people don't talk like that when you interview them. They talk in circles. They jump from point to point like they don't fully explain things. And so most of the work is actually making the interview read well.

Stew: Fantastic. Well, I think we've done it with an extra little half an hour Q&A, I just thank you. Nathan and Dan for being so generous with your time. I just learned an enormous amount. And I hope everybody else did too.

Nathan Baschez: Thank you everyone for being here. It's like so cool to just do this. This is great.

Stew: Yeah, this was a blast. Thanks, everybody for the awesome awesome questions. Those were just stellar. Stay tuned for the notes and the recording.

Nathan Baschez: Let's all give ourselves a big pat on the back.

Stew: I mean, these are the true believers. These will be the people who build the next Everything bundle. So thanks again for all the time everybody.


Dan Shipper and Nathan Baschez are co-founders of the paid newsletter bundle Everything.

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