Earn a Living as a Writer, Without a Writing Background

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

1:59I am fascinated and okay, fine. Also, sometimes a little jealous and frustrated by people who build amazing content-focused businesses as a writer, as a creator, but don't actually have a writing background. They come from somewhere else, and yet they somehow entered into writing and then blew up. And the reason why I find this so fascinating is because I do come from the content world. I come from a writing and an editing background. And the peers that I have in that space, they don't really know how to build product. But then I look around at people who come from other places, who come from finance, who come from product development, who come from business and marketing.

2:48And then they enter the content space and sometimes they just kill it. They just build incredible, powerful brands. And it's always a reminder to me of how success does not rely upon mastery of one skill. It's often a mastery of many skills or recognizing an opportunity to marry skills in maybe unpredictable or unusual ways. And that's what I want to learn more about. Because I think that we all, whether or not you want to be in the content business or not, we all need to think about how we can marry skills, how we can take part of what we've learned in one arena of our lives and our work, and then match it with something new that we're going to explore or something that we learned from somewhere else.

3:41Anyway, all of that is to say, that's why I reached out to Sahil Bloom recently, because he is one of those guys, one of those guys who does not come from any kind of writing or content background and has really mastered the business of being in that space. And I wanted to understand what it was that he was doing and where he was drawing his insights and how he saw them match up to this new space. And you know what's fascinating is you can hear a bit of this shift right there in the way that he introduces himself. I am Sahil Bloom. I'm a writer, entrepreneur, and investor based in the New York area.

4:23And broadly speaking, I like to think that I create content to help people live a healthier, wealthier life. His newsletter, which is called the Curiosity Chronicle, has 600 ,000 subscribers. And Sahil has expanded into all sorts of areas in media production, which we'll get into later. But anyway, let's go back for a second here. Did you catch how he introduced himself? He said, I'm a writer, entrepreneur, and investor, which is interesting, because if you think about the way that I just kind of introduced this whole thing, people coming from the non-media space and then entering media. Sahil starts with writer.

5:08That's the first word he uses to describe himself. But that's not his background at all. So you're correct. I did start my career in the world of finance. I spent the first seven years of my career as an investor at a private equity fund. I had a great experience, learned a ton in the early years of my career. And fundamentally, what it was for me was that I didn't get a lot of energy out of the work. And I'm a big believer that you do your best work when you are deriving the most energy from what you're doing on a daily basis. There are plenty of people who do derive a ton of energy from the work as an investor.

5:40I just wasn't one of them. And what I found was for someone like me who is most excited about the potential impact that he can create in other people's lives, and someone who doesn't necessarily place money at the top of my chart of what I'm most excited about, I found that I could create the most impact and derive the most meaning from writing and from the scale of the internet in particular as it relates to that. But to get there, he'd have to understand the business of writing. And he'd have to understand how writing travels and how it connects. And so what he did was take the analytical mind that he had developed that worked so well in the finance space and applied it to this entirely different arena, an arena that's more art than numbers, but as it turns out, can be built by thinking numbers too.

6:35And so that's what we're going to talk about today. Sahil is going to break down for me how he understood this space and where he sees the opportunities. It was a really fascinating conversation. And I should say even more so because, and I didn't realize this until we started talking, that he didn't really set out to build a big business in the writing space to begin with. He just realized that he understood how to make an impact there. And in a way that I think a lot of writers don't think about enough. So that's what's coming up today on Problem Solvers right after this break. Hi, I'm Robert Tuchman, and I host Entrepreneur's How Success Happens podcast.

7:19Each show, I get to interview a successful entrepreneur. Many have built some of the biggest brands in the world, like Lululemon, Warby Parker, Patron, and Drybar. But here is the part I love, because after doing hundreds of episodes, I've noticed, regardless of one success, we rarely get to hear about all of the challenges they faced and overcame to get there. They all had to pick themselves up off the mat at one time or another. I love hearing their stories and how these people we find incredibly successful today are really just like you and me. They all faced difficulties, but they all kept going and got through them.

8:04On How Success Happens, we dive deep to find out how they overcame these issues and what was it that drove each of them to keep going and never quit. Because let me tell you, they all face difficult times. It's a great podcast if you want to learn from the best while inspiring yourself. All right, we're back. I am talking with Sahil Bloom, author of the Curiosity Chronicle newsletter, among many other things. And we're talking about how he built a really thriving business in the writing and content space without having come from that background. And to start, I told him that thing that I had said to you at the beginning of this episode that I'm fascinated by people who come from outside the media space and then seem to understand how to build in the media space better, I think, than many people who spent their whole careers just thinking about words and communication because they're able to think about words and communication, but also business and structure in a way that's frankly pretty useful.

9:09So that's what I said to Sahil. Yeah, it's a totally fair point. And I think broadly, probably correct that people that come from a background in investing or in business and then take to a creative endeavor naturally have this lens of, okay, I'm going to apply those business frameworks and principles to how I think about writing. I would add a nuance to it in my own case, which is I started it like purely as a hobby. It was 2020. I all of a sudden wasn't traveling four days a week and flying and working 80 to 100 hour weeks just because we were stuck at home. But I was still working my full time job as an investor at a private equity fund.

9:46And I started writing on Twitter originally in May of 2020 with 500 followers, just because it was like a fun, creative outlet. I had always loved writing, but it was not something that I thought, oh my God, I'm going to quit my job a year from now and go all in on this on a business. I don't think I had a single inkling that it could be a business until like a year after that, maybe when I had built, I don't know, say 100 ,000 people in my Twitter audience at the time. And it was only because it got forced upon me where I wanted to move back to the East Coast to be closer to family. I realized I was going to have to leave my job and I couldn't really find another investing job that was grabbing me and creating energy for me in the way that the writing was and in the way that the creative work was.

10:28So it was really like a combination of the two where once I flipped the switch and I started thinking about the business of writing and the business of creating, that was when I kind of had the aha moment that, all right, I've been doing this as like a little side thing on the weekends and it's grown to where it is today. What if it becomes my main thing? How big could I build it? How impactful could I build it? How much money could I make off of it? There was all these new questions that then sort of jumped to the fore that previously had just been existing in the background. Before you go there, before you go forward, I want to take half a step back because I'd like you to orient me to that exact moment.

11:03Because I think when somebody thinks, is there a business here? The first thing that they do in their head is they lay out their assets and they try to understand why those assets are working or why they have any kind of market value. So what do you think you were doing right that had developed the kind of audience and created this opportunity? You weren't doing it strategically to think of it as a business at first, but something was working for you in a way that it wasn't working for others. I remember, for example, you lean, and I can't remember if this was in this time or not, so you'll have to correct me, but that you and I would see you on Twitter leaning very heavily into threads and into the kinds of things that you were clearly doing because number one, you had good things to say, but also because you were optimizing for whatever the medium was going to reward at the time.

11:51So what do you think you were doing right before you started to think of it as a business? Yeah. And think of it as a business is an interesting phrase because I wasn't thinking of it as a business in the sense that I wasn't trying to monetize and make money and make a living. But I was thinking of it as a business in the sense that I wanted to grow. I wanted it to be the most impactful and largest thing I could possibly build because that's how I'm wired, I got a scholarship to play baseball at Stanford. When I was going to do something, I wanted to do it at the best possible level. And so in that sense, I was thinking of it as a business from day one.

12:24And so to your point, Threads was the medium that was my initial thing. And I was probably the first person on Twitter to really recognize the potential of long form content. There had been a few people that had toyed with Threads, but no one did as consistently as I did over a long period. And what I really figured out was that you could effectively create a Twitter native blog by embedding other threads that you had recently written into new ones. So when I was writing originally around topics related to finance and economics, I could couch topics into a new topic. So if I was writing about something that was happening in the market and I was going to reference something like a call option, well, I had already written about call options.

13:09So I could say, oh, if you want to learn more about that, here's the thread I'd written and sort of create like a Ben Thompson, like blog almost that was Twitter native that just, if you think of like a market, those threads were clearly driving outsized impression growth on the platforms, which was leading to follower growth because I was writing, you know, at a high quality bar, like I was spending four to eight hours per piece, probably long, long times really focusing on it. And I was one of the few people doing it. Now, like any market opportunity, when people notice that something's working, then everyone floods into it and the opportunity gets, you know, the window gets squeezed shut, which I would argue happened.

13:47But in that early period, the biggest thing I was noticing was like, okay, this is clearly a medium and a format that is working. I'm doing it early. I'm one of the earlier people and I'm doing it better than people. And so I'm going to keep doing that and keep replicating it until I kind of like, you know, have a reason to stop at that point. Okay, that's really, really helpful. And just to be clear, you're right, that opportunity had shrunk. Everyone did it, it became incredibly annoying. I actually don't know if you still post threads or not. Not really. No, I mean, I think like, look, the opportunity window definitely shrunk as more and more people did it.

14:23And as more and more people did it poorly, like there's still an opportunity to write something exceptional that will still get seen and stand out. But the vast majority, like 99 % is crap, like it is in any other market. And because there's all this noise, it's harder to stand out as a result. Right. And I think that right there, before we turn into how you then started to think about how to monetize this and your point before is well taken about what does it mean to think of it like a business from the very beginning, you were looking to grow and to optimize, even if you weren't thinking of it as a primary revenue source.

14:56A lot of pure writers don't do that, they see, in fact, I think, a focus on the market and a focus on playing to what a market rewards as in some way diminishing the value of the thing that they're making or that it isn't as pure or as satisfying. You, though, don't sound to have any regrets about it. I would argue you You probably figured out that if you could play to what was being rewarded in the marketplace, which at the time was Twitter and you've expanded in a lot of other arenas, that you could just do what you were enjoying doing, but bigger and better, that there was an impact to be had by figuring out what was reaching people.

15:41And yeah, maybe it means that you had to write them differently or structure them differently, but that ultimately you were at your core getting your thoughts out and there was a satisfaction to that. Could you just square that for me for people who maybe feel like they're in that limbo stage between how much do I play to a marketplace and how much do I create a pure version of what I want to make? Yeah. The mental model I have for this is that everything exists on a spectrum. So basically, on one end of the spectrum is the ultimate purity, only creating the exact thing you want to create, even if you know that the market for that thing is effectively nobody.

16:18Like, hey, maybe nobody sees this, but I feel so amazing at the purity of this exact thing on one end. The other end of the spectrum is like the most cringe piece of content you've ever seen in your life. Talk like, here are 10 TED Talks that will change your life and someone makes a thread or here are 10 movies that'll change your life and it's a bunch of posters. And those were, for whatever reason, exploding and people like hundreds of thousands of likes. And I don't know who was liking them, but people were. And what you have to do as a creator, as a writer, as an entrepreneur is figure out where you want to exist on average on that spectrum.

16:54I was never going to be on this end of the spectrum, i.e. like the most, most purity, because I want people to see my work. I want to impact people. And so I would think I was shooting myself in the foot by going all the way over there. I also was never going to be on the cringiest end of the spectrum. I've never once created one of those like on trend things about Excel tips or about, you know, Google Chrome extensions or TED talks. I just wasn't willing to do that because for me, like Tim Cook and Jeff Bezos follow me on Twitter. I don't want them to roll their eyes at me. Like they are real amazing people that I admire that follow me.

17:26And if they see me post something like that, they're probably going to roll their eyes. And so my whole perspective was it's somewhere in the middle that I wanted to live. And are there things that I would have posted over time that I thought were more growth leaning and more growth oriented, more mass market? Sure. Then there were things that I thought were more niche, more esoteric that I didn't expect tons of people to like, but that I did know that the people that interacted with them would get value from them. And my whole bet was that by getting larger than the things that you do that are more pure, which is where I focus my energy now are just going to reach more people.

17:59So now that I have a larger platform, I can reach people with the weird inspiration driven esoteric stuff because my platform is much larger. Yeah. So let's, let's go back now. I had taken this a half step back, but let's talk about that. So you said, you know what, I think that there's an opportunity here. There's an opportunity to build something real and substantial as a business. What'd you do? Yeah. So there are two pieces to this. You know, the first one is just sort of like a broad, overarching strategic view that I had, which was that most creators monetize in kind of a core set of ways.

18:31It would be like ads or selling courses slash products. And the challenge with that is that you're constantly having to sell, right? Like you're constantly having to create a new piece of content and then sell to your audience. So you say like, well, I have a big audience now, let me sell courses or let me sell an ebook or whatever the thing is. And the challenge with that is that it's really hard to do over like a 20 or 30 year time horizon. It's it's like really hard to make a true long-term career in that. And I knew that going in. So my view was, what's like a more sort of durable way to earn as a quote unquote creator.

19:08And what I did was I looked at my P &L. So I looked at, you know, this is like the business minded me. I looked at what I was spending money on, on a monthly basis while trying to grow my platform. And it was things like design services. It was things like video editing services. It was things like the backend operations for my newsletter, like people to kind of like play with and tweak, you know, things on the backend, the non-creative part. And my perspective was then, okay, how can I flip those cost centers into profit centers for my business? Take the Amazon model of what they did with Amazon web services.

19:40It was something that they were spending a ton of money on. And then they decided to turn it into a profit center. It's, you know, it would be standalone, a fortune 100 business today. And so I wanted to do the same thing, albeit not at the same scale. And so what I did was I started partnering with people and launching these businesses to actually go out and turn these things that I was spending money on into profit generating machines. So in the time since I went all in on this two years ago, I've launched now, I think it's a portfolio of 10 businesses, you know, that'll collectively do over$10 million in revenue this year, you know, at really high margins, because they're high ticket services businesses, they don't require a whole ton of upfront cash or investment.

20:17And I don't have to talk about them on a daily basis because the lead generation comes in naturally from existing clients and from whenever I'm actually putting out pieces of content that are created by my company. So like my video editing company, it's every time I post a clip or a reel on Instagram, that's content that's coming out from my company. It's effectively content marketing. So that's really what I did from a business perspective that created this profit engine that then sort of just runs in the background and allows me to actually focus my time and energy on the real creative work, which is what I love.

20:50It's funny that you... So I'm going to go back to your introduction. You would first identify it as a writer. But it's so interesting to hear what the business of writing is for you because writing isn't just about communicating. It's also about creating a marketplace. Writing is the exploration of the needs of everyone else who is writing. and you're recognizing opportunities in there. In a way, you're using your own writing as an experiment for what that marketplace demands and what people who follow your path need. Yeah, I think that's exactly right. I mean, I knew if I was encountering any of these needs that there were a lot of people that were.

21:34The creator economy was growing at a rapid, rapid clip. There were tons of businesses and people that were looking for these services. And I also knew that I would be able to reach many more people if I never had to sell products or worry about charging people for things. And so that was like, in my mind, the really big unlock, which was, I can grow my newsletter, and my social platforms, and ultimately my book much faster, if I'm not constantly having to sell some new product or course to people. Like if I'm having to come out and keep saying like, hey, buy this new course on social media growth or buy this new journal or whatever the thing is that I have to sell in order to feed my family and pay my bills as a creator.

22:15If I don't have to do that, I can just focus on creating incredible content that people naturally want to share. And I can make money elsewhere. And I can make money in a way that's like sort of on autopilot. It has CEOs, there are operators running those businesses. That was a huge mental unlock for me because it just allows me to focus on creating great things that I'm proud to share with people. What did you do strategically on the content side itself to be growing that audience? So the way that I think about content is you need to have a halo product that you can then reproduce across multiple formats.

22:49And so what I mean by that is a podcaster, as an example, has a podcast. That is one piece of halo content. Most podcasters will go record the podcast, and they release the podcast, and maybe they post about, hey, the podcast is out and that's it. If you were to tell me I had a podcast, I would approach it differently. I would say, okay, I have a podcast. I just recorded this halo piece of content. Now, what can this turn into that will create this unbelievable growth engine everywhere? Well, a podcast can be turned into at least like 15 or 20 shareable moments, video clips or audio clips that are shareable.

23:26Those will all go out across the video native platforms like Instagram, TikTok, now Twitter, etc. A podcast also turns into a bunch of interesting learnings. I might have learned some interesting frameworks, mental models, ideas. Those become Twitter threads. Those become newsletter articles. Those become LinkedIn posts. So now you're kind of getting the point that like one podcast is not just a podcast. A podcast is actually like 20 pieces of content that can go out across everywhere and over a long period of time. And now what I'm trying to do as a creator is how do I create once and have it amplified 100x across everything?

24:03So for me, my newsletter is really my Halo product. That's what I spend the most time on every single week, really writing in depth. And I want to know on a weekly basis, how can I turn that like in-depth research driven newsletter into a bunch of content that goes out everywhere. So there's a lot of sort of like reproducing, tweaking, grabbing ideas from and expanding on them, that's where I kind of focus my energy. And it allows you to create a whole lot more content than you would otherwise be able to on a weekly basis. That is a great and tried and true strategy for content producers. But I'm curious to hear if you have a system underneath that, that helps you do it and do it well.

24:46For example, I try to follow what you just described there, where I will record a podcast, and then somebody will have said something in interesting. And maybe I'll turn that into a newsletter. And then maybe I'll turn that into a LinkedIn post that promotes the newsletter and so on. But it's kind of ad hoc, if I'm being honest about it. You're not, you don't seem to, you know, strike me as an ad hoc guy. You strike me as a guy with systems. What's behind all this? How are you breaking this all up into different pieces of content? Are you tracking it in some way? Are there buckets to fill? What's going on?

25:14So I have a chief of staff who's like my, I don't know, my Robin, I guess, to my Batman or something like that. He's like my right hand. And he is the extremely organized one. I am the disorganized, like creative one. And he has created a really, really strong. So it's in Notion that we use, but it could be in anything system for basically logging and tracking ideas and where they've been shared. So if a new idea goes out in the newsletter, okay, that's been used in the newsletter, but it hasn't yet been turned into an Instagram reel. It hasn't yet been turned into an animation. It hasn't been turned into a Twitter post or into a LinkedIn post.

25:50And it allows me to then just like on any given day, if I'm looking at something, pop that idea tracker open, know what I've shared, when I've shared it, how much I've written about it, whether I want to expand on it. And because I'm more inspiration driven, like I don't create content in advance. There's no, I don't know what I'm posting tomorrow. As an example, I don't know what my newsletter is going to be next week, because I'm creating kind of like on demand and then posting things. That idea tracker has been really, really critical for me on just like staying on a daily cadence of putting things out, which is really, that is like at the heart of growing and scaling your platform across all of these is just like a steady cadence of high quality ideas and content.