The Bootstrapped Founder

Most of Josh Spector's newsletter issues are just a few sentences. Sometimes, just a link. And still, advertisers and readers alike flock to Josh's emails. In our conversation, you will learn why brevity is so attractive, how to make sure you're telling the right stories to the right people, and how to build systems that keep people coming back for more.

00:00:00 How to think about scarcity
00:04:16 Josh's newsletter(s)
00:08:49 Ads that feel less like ads
00:12:21 Why you need to know what you want to sell
00:16:20 How Josh got started
00:22:02 Advertising is just another way for people to connect
00:26:32 Maintain and improve the quality of your audience
00:30:51 How to get people to subscribe to your newsletter
00:34:54 Why you need to shorten your email newsletter
00:39:28 How to use video as part of your content strategy
00:48:12 Empathy with the needs of your audience
00:51:31 Helping your reader
00:57:16 Having an audience centric approach to business

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Find me on Twitter:

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Creators & Guests

Arvid Kahl
Empowering founders with kindness. Building in Public. Sold my SaaS FeedbackPanda for life-changing $ in 2019, now sharing my journey & what I learned.
Josh Spector
I publish a one-paragraph newsletter, three-question podcast, and daily thread to simplify audience and business growth for you - and my 31,622 subscribers.

What is The Bootstrapped Founder?

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.

Today, I'm talking to Josh Spector, audience building expert and author of the most condensed newsletter that I've ever read. Some of his emails are just a single sentence. But that sentence usually packs a punch. We talked about consistency, finding sponsors for your content, and how to be interesting in front of interesting people. Here's Josh.

So Josh, your newsletter is a single paragraph of text with a sponsor linkway. Don't even mention the name of the sponsor. And I don't think any of these things is a best practice anywhere. But it does seem to work incredibly well for you. Why is that? Why does it work?

Why does it work? Well, it's interesting. So let me start with sort of the backstory of how I wound up doing that because it is a little unusual. Basically, you know, I've had my newsletters called For The Interested. I've written it for over six years now. And originally it was a weekly newsletter came out every Sunday, a collection of basically links and summaries to articles and resources to help people grow their audience in business. It worked really well. And I also work as a consultant and I help people grow their newsletters as well. And one of the things that I would, when I'd have conversations with people about newsletters, they'd always go, oh, it seems like a lot of work. I'm not really a writer. They have a million reasons why they you know, we're scared of doing a newsletter. And I used to say to people like, look, a newsletter is just a value delivery mechanism, right? The idea that a newsletter has to be long has to be what "most newsletters" are, isn't actually true. And I said, you know, I bet you a newsletter could be as little as a sentence as long as that sentence was valuable, poeople would love it and they would keep opening it. And I kept saying this over and over again. And somewhere along the line, I was like, well, I do actually believe that. Maybe I should try that. Like I keep saying that like it's fact, but I think people would like it. I don't know. So I started as a sort of side project, this sort of separate newsletter that I called The Daily Graph. And I didn't lock myself into a sentence, but I locked myself into a paragraph, right? So I said, this is gonna be a daily newsletter. It's gonna be one paragraph, usually one paragraph and a link. Sometimes it is as little as a sentence. And let's see what happens. And I promoted it in my newsletter. And I have about 20,000 subscribers on my newsletter. And about, you know, over a couple of weeks, about 1000 or so people signed up for it. And I did it for a couple months. And I found people loved it. That number one, they were opening it, you know, daily newsletter can be a grind for a lot of people. So number one for me, because it was so short, it was actually easy to create daily, right? I would never do a daily newsletter that was like a long, full newsletter, that'd be way too much. Too much work for me and too much for people I think to get. But I found that people opened it because they number one, it was valuable. They liked it. So my theory was correct. But they also knew and I found this in my own behavior that there were newsletters I really liked. But that sometimes I knew if there was long and there was a lot of stuff, I would hesitate to open up. Maybe like I don't have time to read that right now. I'll get to it later. But the newsletters I opened the most consistently were the ones that were short, that I knew I could quickly skim it, you know, whatever. So I found that to be true as well, right? People would open it every day because they realized this is gonna literally take me five seconds. And I'm either gonna click the one link because I'm interested in it or not, right? It's not a big commitment. So what happened was, it was going really well and the types of things I was sharing was audience and business growth tips. It was similar to my main newsletter but just a little different. And I got to a point where I had a couple 1000 people maybe getting it but then I had 20,000 people over here. And so instead of trying to get them to opt in, I said, you know what? What if I just combine the two newsletters? Start sending it to my whole list and allow them to opt out if they don't want the daily. And so that's what I did because I said, I think a lot of these people are gonna like it. They just don't know they don't wanna go to the trouble to sign up for something else. So I did that I said, look, now my For The Interested newsletter is gonna be this week day one paragraph thing and the Sunday one is still the full longer thing. And if you don't want the daily, you can opt out and just get the Sunday. And some people did, but not that many. So literally overnight, I went from a daily that was going to 2000 people to a daily that was going to almost 20,000 people. The other thing that I noticed and the other reason why I did this was because when I was sending the daily before I merge them, the clicks, the engagement was massive. And I could tell and at that time, I wasn't running ads in the daily. I was just running them in the Sunday one. And I realized because it was so short, because it was so simple, because there was basically one link to click that if I sent this to my full audience, the engagement was probably gonna be massive and the engagement on the ads would also be massive. And that's exactly what happened. So that made the ads way more valuable. And because they would drive way more clicks, I sell them package. So when people buy an ad in my newsletter, they get a mention in the Sunday and they're the sole sponsor of a daily one. So there's five ads in Sunday, one ad each day. And to give you an idea of how different the engagement is, and this is such an example of less is more, I will get more clicks on one link in my one paragraph daily newsletter than the 15 or 20 links combined in the Sunday newsletter. The engagement is massive. So that's sort of how I kind of stumbled into it. But it's worked really well. And in terms of not mentioning the brands in the ads. So when people buy an ad, they give me the copy for their ad in the Sunday issue. I write the copy for their ad in the weekday issue. My goal when I write that copy and it's just a sentence, there's no images, it's not like the traditional ad. It's a single sentence with a link. And my goal, in my mind what an advertiser is paying for is they want people to go into their world, right? To their websites, to their landing page to ultimately buy or take whatever action they want them to take, right? Most of my advertisers it's not a brand awareness play. They don't say, oh, there's that company I've seen a million times. It's like get them into that world. So my goal with writing the ads is to what is the sentence I can say that is gonna make my audience most likely to go check out their thing. Because ultimately, that's what is gonna serve them best, right? They're not gonna drive sales or they can't get people into their website or landing page or whatever. So I sort of again, sort of stumbled into it. But I'm, you know, it's not clickbait. I'm not misleading people because that doesn't do me or the advertisers any good either. But I am driving curiosity, right? So like, if I was to promote your newsletter, I wouldn't necessarily say or your podcast, I wouldn't necessarily say go check out The Bootstrapped Founder, blah, blah, blah, blah, blah. I might say, go check out one of my favorite podcasts. That's a must watch for anyone that's trying to grow their business or startup, right? That little bit of curiosity to drive people there. And I know my audience and what they're looking for. So I write that copy in a way that appeals to what they're looking for. But the combination of that with the just minimal nature of it has led to really good engagement.

Yeah, I bet. I've seen your emails and I get them every day. And I find it very exciting all the time because it's just always a masterclass and doing it right. And what I found is that you seem to have really understood the concept of proximity, like you both in terms of the ad, right? The ad is very close to the only text that's in the email. So people's attention is gonna be on that sentence. And then there is the link, right? It's not like hidden two scrolls down or behind some image somewhere, it's right there. So that's approximate to the content that people enjoy. But what you do in phrasing it this way gives people proximity to you. So you become the gatekeeper into that world where your advertisers, your sponsors want people to go. So you have this kind of double sided proximity effect of both in proximity to the text and to you as the person formulating it, which is such an incredibly alluring thing. Like I wanna click on this even though I don't care often about the product that's being advertised. It's bizarre, it's really effective. So I quite enjoy it.

Thank you! I think there's two other pieces about it or elements that I think have helped it work well. The first is just sort of basic, right? There's a lot of trust, my audience trusts me, right? They know that if I recommend stuff, they know, I'm not gonna recommend something I don't believe in. They know I'm not gonna be promoting stuff that's sketchy or shady or anything like that, right? So that's basic, but I think it really matters. And I've been doing this for a long time. And so, you know, the other thing is if the stuff I'm sharing, not the ads, but if the content I'm sharing is regularly valuable, there are a lot more likely to click the ads, right? So the other and I'm not hiding, I'm not pretending. It always says, you know, today's email is brought to you by Bob. I'm not pretending it's not a sponsored link. Like there's none of that. So that trust factor helps. The other thing is, and I think this is really interesting because I've talked to people that run ad networks and stuff. And you know because they're amazed by the engagement I get on my ads and the click through and that stuff. And what's interesting is people as users, as consumers, we're used to tuning out ads that look like ads, right? So the fact that there is no image, the fact that there is no big brand logo, that there is no any of that stuff, it feels a lot more like my ads feel like content, right? And I think that makes a huge difference. I think a lot of these brands that are thinking, oh, I want this box in my brand and logo and my copy and my whatever. While I understand that, I don't think they realize that most users are tuning that out, right? I subscribe to so many newsletters that have the spot at the top, it says you know, sponsored by blah, blah, blah and whatever. And I think lots of other people just scroll right past it, right? And you actually train your readers to know that that top spot is just an ad and I don't care and I go past it. You're never gonna get the click if they're not actually reading it, right? So I think the fact that the ads don't look like ads also makes a huge difference. And that combination of trust and value and you know, people actually like my ads because they're fit and they're relevant. And all that stuff makes a huge difference compared to I think the way most people do ads.

Yeah, it shows that you have a quality expectation and that you do some vetting, right? On the people that you suggest their products off like you don't like if you phrase your own sentence to get people interested in a sponsored product or an advertised product, then you have to at least understand what it is. And if you in figuring out or trying to figure out what it is learn that it's not something you wanna sell, then you don't run the ad. So obviously, you know, it's a very clear message that you actually condone whatever they wanna sell to people, which is powerful, I feel. And you're right. In my own newsletter, I very much highlight the fact that it is an ad for fear of people not seeing that it is one. But I don't let anybody advertise in my newsletter that I would not want to buy the product of myself, like the people that advertise on my thing. I really check that stuff out because I want it to be found or compatible, bootstrapper compatible and all of that kind of goes into it. So why wouldn't I just tell people hey, this is kind of cool. I'm trying to learn from you as you could probably tell, right? This is important to know.

No, it's more valuable. And I also think that, you know, and this has nothing to do with like, I'm a decent copywriter and all that but has nothing to do with copywriting skill. But the truth is, no one's gonna know what resonates with my audience better than me, right? So that's why the one of the reasons why I have them give me copy for the Sunday issues because I can see okay, what did they wanna play up? What's the angle that they want to promote? So now I understand their point of view. And then I'm gonna translate that into language that I think is best gonna resonate with my audience, right? And so whereas if they gave me no copy, that would be hard because I'm just looking at their sales page or looking at whatever wouldn't be hard, I could do it. But who knows if it would align. So getting the copy from them is like, okay, I see you wanna play out these features. I get it. Let me talk to you know, and you might see for example, little things, right? Like, somebody might have a product that they say is aimed at startup founders, right? But I know my audience, even if maybe doesn't use they don't think of themselves as startup founders, right? This product might help a lot of my audience, but those words are not the words that my audience uses, right? So I might change that to creative entrepreneurs or you know, whatever it is or just play up the thing that it will help them do, right? Get more, you know, drive more sales or whatever it is. And those are little things that like no brand or advertiser is gonna know nuances of your own audience. And the other thing that I would say about this also is that understanding your audience and you know, most of my advertisers are my readers. I don't have, I'm not doing sales outreach other than promoting it in my newsletter. It's basically a self serve ad system, you go to for anyone that's listening and you pick a date and you buy your ad and you send your copy. And we're off and running. It's really different if I was out approaching brands going, hey, I have this thing you don't know anything about, wanna advertise in it. And so I think that helps too in terms of relevance of advertisers, most of my advertisers are my audience in some ways, which is awesome, cool, and helps.

Guess it works pretty well within our industry, right? Of entrepreneurs, right? Of people who have some interest to bring a product into their own community as well as going to entrepreneurs serving entrepreneurs. That makes sense. I think you've found a good way to do this. Did you try other ways of getting people to run ads on your newsletter?

So again, it's the ad started. I'll give you sort of I know I told this story before, but I'll give you sort of a quick version of the origin of my ads. And by the way, there's my podcast, which is called I Want To Know. There's an episode there that is all about how I do ads and how I started it and my whole sort of ad system. But the short version is this for the first like four years or so of my newsletter, not only did I not run ads in it, I was strongly anti ads, right? I was like it's not good for readers, the interests aren't aligned. Now you're sort of serving the advertisers. It's annoying, they're interruptions. I was vehemently like against advertising of all sorts. Then I had this thing happened where one of my readers reached out to me and she was a therapist who specialized in helping creative people. And she said to me, she had run a classified ad in Friedman's newsletter and that it had done really well for her. And she said, it's like the best marketing I've done. I got just the right people and the right clients, and whatever. Do you know any other newsletters that have a similar audience that I could run ads in. And again, this was a few years ago before this sort of newsletter ad thing really took off. And, you know, it struck me that I had her audience, right? I was a perfect fit for her. I just didn't have ads or anything like that. And so when I took a step back and thought about it, I said, well, you know, I have this sort of principle in my mind that advertising is bad. And my newsletter is never gonna have ads and all of this stuff. But are they really so bad? Here's a woman who's in my audience, who has a good service to read to offer that would help my audience, lots of people who, you know, are looking for a therapist or, you know, whatever. So it helped my audience, it would help her, it would help me in terms of because at the time, I didn't know direct monetization in my newsletter. So the only reason I'm not doing this is because I have this idea in my head that ads are somehow bad and gonna ruin everything, right? So what I decided to do, I was like, well, let me at least asked my audience and see what people say. So I sent out a one question survey. That was basically like, if I included classified ads, I think I called them classified ads at the time. If I included classified ads in my newsletter, one, would you be curious or want to read them or see them? It was multiple choice. Yes, I'd want to read them. The second option was I want to read them and I might want to buy one. And the third option was I hate ads, don't include any ads. I was shocked 90% of people. 90% of the people that responded said they either want to read them or might want to buy one. Only 10% said I hate ads. And I saw that I was like, well, I'm completely wrong. Like, this idea that ads are gonna ruin my newsletter. I couldn't be more wrong. And in retrospect, this was brilliant. But it was completely accidental. I didn't realize it until I was down the road. So once I realized like, okay, well, maybe I should try this ad thing. I also realized that I had, you know, whatever it was 50 or 60 people that said they might want to buy one. I had basically done lead generation before even launching the ads. So I took that list. And before I even announced it, I started emailing those people who said they might want to buy one. And I said, hey, I think I'm gonna do this, you said you might want to buy one. I priced it really low. It was like $50. And sort of said, this is what it's gonna be. It's just one ad and there was no daily at that time. So it was just the Sunday issue. And I sold out, you know, the first three or four weeks before I even announced that they were available. So when I announced that they were available, I was able to say, hey, I'm doing ads. I sold five per issue, just a sort of random number to limit availability. And I was able to announce it and have people go to the site to buy and see that the first three or four issues were already sold out. So I purposefully, this is a whole other thing. There's my background, I used to work in the comedy industry for a while producing shows. And so I always say to people, it's like, if you think you could sell 75 tickets to a weekly comedy show, would you rather book a 50 seat venue or 100 seat venue? And the answer is you should book the 50. Most people would say the 100 seat venue because I can sell 75 a week, so I'm leaving money on the table. The answer is the 50 seat venue. Because the perception and branding of a new show being hot and it being tough to get tickets leads to create the whole perception that this is a good product that ultimately in the long run is gonna help you versus there's 25 empty seats at every show. And I can go whenever and you know, et cetera. So I took that and applied that to this, right? I priced it low. I wanted it sold out. I wanted so that when from the very first time people saw it, they were like, oh, these ads must be good. These ads must be you know, it was a desirable product. And it went from there knowing that I could raise the price over time. And they've sold out almost every week since and that was you know, a couple years ago. So that's sort of the the quick backstory of how I got into the ad business to begin with because I was very skeptical.

Yeah, that's kind of what drove me to wait for 100 episodes of the newsletters before I started with it too. It's always this weird perception that marketing kind of destroys the purity of a product. But if the whole idea of the product is to connect information with people and people with people, and products with people or ideas with people, then advertising is just another way for people to connect with a certain thing. And this is something that I had to unlearn to actively unlearn the idea that advertising is always malicious that somebody wants to push something I don't want on me. It's not the case, right? People pay to be in my newsletter to talk to other founders, to show them what they could potentially use to solve their problems. And if it's not good for them, they click and nothing happens. And if it's good, which is likely because it's vetted and you know, it's somebody who wants to help them, then there's a chance that there is a business relationship coming out of this at some point, which is the whole point. I want to empower founders to build better businesses, right? So it kind of, you have to understand that advertising most of the time or sponsorships, whatever you may call it, is alignment. It's not diffusion, it's actually alignment. So I'm very glad that you explained it this way. Also how it came to be because I think that is a great way for people to understand how advertising is something that naturally comes with a bigger growing audience. When your audience grows, more people come that might be interested in talking to the same people. Its like a fan club, right? If you are in the Harry Potter fan club, you wanna talk to other Harry Potter nerds. That's just the idea. And if you have something cool, you want to show them, well, you posted in whatever discord that I'm totally not in. You might be communicating with these people, right? Like that's just how that works. And then from there, information just springs out and people are super happy that you shared it. And an ad is just the exact same particularly in our community.

Yeah, and I think that's especially true. One of the things that I came to realize through doing this was that the ads are, if people talk a lot about like, this is a way to monetize my audience, right? But it's actually a way to serve my audience. If you have an audience where members of your audience want to reach other members of your audience, offering ads is actually serving them because you're creating and going back to that first example of the therapist, right? she was in my audience and wanted to reach the rest of my audience, right? And the rest of my audience was gonna find value from what she had to offer. So understanding the mindset shift to going, okay, offering ads isn't just sort of taking advantage of my audience, it's actually serving them. And then the other thing is when you have that situation where members of your audience wants to reach other members of your audience, you also can potentially get in a place where because the other thing that held me back from ads and I think holds a lot of people back from ads is it seems very complicated. I don't wanna do sales calls. I don't wanna cold call brands. How am I gonna find advertisers? If you have the type of audience where that matches, right? Where your audience can be your advertisers, that removes all of that, not all of it, but it removes a lot of that other stuff. Because that was the other thing that held me back was like, it seems like a lot of work. I don't wanna spend my time, you know, negotiating deals and tracking down leads and all that kind of stuff. So it doesn't work for every newsletter, but I think for a lot of newsletters, members of their audience wants to reach other members of that audience. And I think that it can be a really good fit.

You've given me great ideas on how I can incorporate that particular part into my newsletter as just a little sentence, right? If you wanna reach other entrepreneurs say, read this newsletter, here you go. And I have this in there, but I phrased it differently. So thanks for that already. And one thing that comes that absolutely, very clearly comes to mind is that for this to work, you have to have a high quality audience, you have to have the right people in that audience, right? You have to have the people who would be interested in helping other people or be helped by people in their community. And you said two things recently, that I found very interesting. One was you have to not just be a write a good newsletter, you have to write people's favorite newsletter. You have to become their most favorite creator. Because that kind of aligns you know, the quality of the person with the quality of the creator. And the other thing was that if you have too many anonymous accounts in your social feed and your follower group, you have a problem. And both of these indicate from two different sides how important quality of an audience is. Can you tell me more about how to maintain and increase and improve the quality of your audience?

Sure, so let's start with I think the key to growing an audience is providing specific value to a specific audience, right? Alignment specificity is really, really important. And I see a lot of people where, and this extends to products and services as well. But even just from an audience standpoint, there's not alignment, right? They say they want to attract these, you know, these people, but they're talking about stuff that appeals to other people, and sometimes successfully, right? And then they go, I don't understand why I'm not getting clients or business or sales out of this. I'm growing my audience. I'm growing, you know, I have newsletter subscribers, but it's not leading to anything. And they lead to frustration and all sorts of other stuff, right? So even defining that term of what is quality audience mean, I think is really important. And to me, quality is about in some ways that alignment and trust and engagement, right? So for example, like, this is an extreme example, right? I could tweet funny cat videos all day and maybe build a bigger audience is not gonna get me anything, right? Like, it's not gonna get me clients or business or any of that stuff. So I think that alignment part is really important, this specific value for specific people, which is where I sort of start with everything. And I have people ask me all the time. They go, well, you know, how do you define value? What is valuable? And I think in 99% of cases, value is transformation. People are at point A. They want to get to point B, your content, your product, your service, whatever you're offering them is the bridge that gets them there. There's a transformation. If there's not a transformation, I differentiate between valuable and interesting. I see a lot of people sharing content that's interesting, but not valuable, right? Interesting content is I read it and I go, okay, like, that's interesting to hear what's going on in the creator economy or that's an interesting new take. There's nothing for me to do with it, right? It's the difference between, you know, a lot of times valuable content, not always, but a lot of times can be how to do this, how I did this, how to get from here to here, you know. The content I share in my newsletter, because as you know, there's a million newsletters out there talking about creators and entrepreneurs and founders and marketing and all this sort of stuff, right? And I think one of the differences and one of the things that makes mine stand out, is I'm only sharing stuff that's actionable, right? So I literally will ask myself, what can someone if I'm gonna share this article or this video or whatever, what can someone do with it after they read it? And if there's nothing they can do with it, it's just interesting and not valuable. And therefore I probably won't include it in my newsletter, right? Not always, but the vast majority of the time that's what I'm looking for, right? So the other thing that happens in terms of quality audience so if you're putting out content and attracting people or putting out content that offers actionable transformative value, you're attracting an audience that wants to take action and wants to transform and wants to get from this clear point A. This is the specificity part wants to get from this clear point A to this clear point B. If you have that, that is a high quality audience not only for yourself, but for anyone that wants to reach them versus what a lot of people do, which is, hey, here's some interesting stuff about X, Y, and Z topic. And this also ties into what I said about needing to be someone's favorite newsletter, not just, you know, it's funny people think about getting someone to subscribe to their newsletter, they think about it as a high bar. Oh, to get them to give you my email address. And it is like it's not a low bar, like to get someone to invite you into their inbox. But that's only maybe half the battle, right? Because the real question is, how are you gonna get them to open on a regular basis your newsletter, your emails, your whatever, right? And that's ultimately what you want because then subscribing and not reading doesn't really matter. And that's where I think lots of people subscribe to newsletters that are "interesting." But they've read newsletters that are valuable. And that's a big difference. And I think a lot of times people think once I got that they're so focused on getting that subscriber, that they're like, oh, I got a subscriber. My list is growing check. I'm like, but are they reading it? Are they and not just opening, right? Are they reading it? Are they engaging? Are they clicking? Are they replying, all those other things that really convey a true quality audience?

It's kind of, it's almost surprising that we don't really understand that immediately as creators because in the software as a service world, customer retention and customer like service, customers success, and even the idea of this kind of customer nourishment, like share value nurturing, right? That's the idea. That's the phrase that where we show people how useful the thing that we offer them is all the time, that we don't translate that into periodical content, which is kind of just an information subscription, not a software but an information subscription. You can learn a lot from the software service space, when it comes to these kinds of things.

I also think you can learn a lot from your own behavior as a consumer, right? I subscribe to a ton of newsletters. And there's a lot of them that I open sporadically. And there's some of them that I open all the time, right? And so why is that? And you know, a part of it again, for me, that's what led me to this sort of shorter format because one of the things I noticed about my own behavior was here's two newsletters that I really like. And this one I open all the time when I get it. And this one, I open sometimes or get to it late, and I asked myself, like why is that? And I was like, oh, because this one I know is like a 32nd commitment, at least to find out if there's something in it that I do wanna click and dive deeper. And this other one, I'll give you a perfect example. And I don't mean this as a criticism because it's probably the best newsletter that I hardly ever read. And it's Dan Oshinsky's Not A Newsletter. Are you familiar with that? He sends, I think he sends it monthly. He actually the newsletter is actually a Google Doc, which is sort of wild format, whatever. And, you know, he sends it once a month. And it covers like everything related to like newsletter industry, media. It skews a little bit towards like, mainstream media publications, but it is packed with a million awesome things about newsletters. It is I'm in that industry, I'm a perfect fit for it. And I don't even know how long it would take to go through it each time. And I find myself every time going I don't have time to look at it now. I look at it later. And sometimes I do sometimes I don't. And it's not a knock on the newsletter. But it's a user behavior. If he was sending me even if he was sending weekly a much shorter version of it, I'm sure I'd be way more likely to read it. And again, not a criticism of it. People love it. It's very successful. It's really good. And look, there's different readers and audience are gonna respond to sort of different formats and different things. It doesn't have to be for me, but that's an example of for me that I see like, you know, there are a lot of newsletters and like that's really good, and I really like it. But if I'm being honest with myself about my own behavior, I don't always open it. I don't always read it, you know, and there are reasons for that.

I'm very similar to this. I have lots of them and they use Hey as my email client so they all ended up in the newsletter kind of marketing stream. So I sometimes occasionally scroll through there. But a couple, they don't go into that stream, a couple of that actually go into my inbox. And you're in there too because I don't want to have to go to the other thing to see the little things, right? The small little updates that are sometimes, like in your case, just a paragraph, that's enough that I can open an email, quickly read it and get back to it. I sometimes struggle with this with my own newsletter because that is obviously a 2000-3000 words essay. It's essentially an essay in the newsletter shape. But I figured that people who want to read that essay, they will be my subscribers. It's not people like me who don't want to read this long essay, I write it. I don't necessarily, I mean, I do read it, right? I never read it into my phone or into this kind of camera for the podcast. But I am not my own necessarily reader in this case. And I create content for people who want a thoughtful essay every week and you create content for people who want something nice every day. These are two distinct, potentially overlapping, but they are different audiences. And that is perfectly fine, right? It's kind of it's interesting because everybody is trying to find the perfect audience. But we should all be looking for the perfect audience for us, right? For what we have to offer. I think that's yeah, that's kind of what I realized is that it's fine.

Yeah, the one thing I would say to you, and again, this is like, I get this question all the time about, you know, do you put the full essay or newsletter in the email? Or do you have them click through to somewhere, whatever. And there's no right or wrong. There's pros and cons to each of them. One thing that it would be, I'd be curious in your case, right? If you instead of sending the full essay in the email, right? If you had a shorter version of summary, the first couple paragraphs, whatever and then have them click to go read it. What I'm curious about is because you're still sending that you're not shortening the newsletter, it's still the same content, right? You're just shortening again, going back to newsletter as delivery mechanism, right? I would be curious if people would more consistently open your newsletter. Because this is my theory, right? This is what I believe. It's not necessarily correct. And every audience is different. In general, because I do the same thing, right? Sometimes, if I have a long blog post, like I don't put the whole blog post in there. I do a quick little summary, right? Because I want people to open it and not feel like if they open it, it's gonna be an epic long thing. If they want to read it, they'll click and they'll go read it. The advantages of it that I see are I do think it helps send the message that this "newsletter" in my inbox isn't work in the moment. So I think in general, people are more likely to open it. But the other big advantage is when you send a full article in the email, you don't really know how many people were interested. You don't know when people read it or not. You don't you don't get that click number. So you don't know you're not able to go wow, this you can judge the subject line a little bit. He replies you get you can kind of judge like this one seemed to strike a nerve or not. But having those click numbers as an indication of how interested your audience was in that essay, to me I think is also an advantage you get from driving them elsewhere. And then the third advantage is you're driving them into your world, right? Because I'm assuming you're driving them to your website where the article lives. That creates a bunch of other potential good things. Number one, they're in your world, they're in your website, they can see different things. People are way more likely to share from the website than in an email. And maybe you have share buttons. I'm not sure where it goes. But my guess is you'll get more social sharing if they read it on your site than you will in their inbox. So again, not that there's a right or wrong, but those are from my perspective, that's why I've always done it the way I've done it as opposed to full articles in there because I think there's some advantages to it. But the flip side is there's people that are like oh, I hate that. I just want to let me read the thing in my email and you know, whatever. So again, there's no one right or wrong way. But

I very much agree there are many different ways and I'm willing to experiment with that kind of stuff, particularly now because I'm kind of shaking up my whole content strategy with having interviews like this very interview as part of my podcast. I didn't used to have that. So my weekly piece of content, I would sit down on Monday write something that I wanted to write about anyway, right? And get it into the podcast form, get it into the YouTube video, talking into the camera form and then getting it into the newsletter and on the blog. It's like four different distribution channels for the exact same thing. But now that I have the video, which is often related, like the interview to the thing that I then write about in the newsletter, but not necessarily. Now you have two things that I kind of want people to see both of them, both the interview and my thoughts about it, right? So it might make sense to summarize my thoughts into something shorter, link them to the block where they can also find the video and then have a kind of summary of the video, as part of the newsletter. I think I might actually run with this and see if that creates confusion, looking forward to that stuff but also opportunity.

Yeah, it's worth an experiment. And, you know, even you know, be interesting, even if you did it for a month or so and just sort of see and compare like, okay, well, you know what happened. The other thing I would say because I'm similar to you where, you know, I have done 20 or so episodes of my I Want To Know podcast and it's the first time I've done any video stuff, right? So just like you, I record these conversations, I'm putting them on YouTube. So I'm learning all that, you know, all that kind of stuff as we go and learning growing a podcast and YouTube channel and all of that. And like you, so now I have this video/podcast to promote every week as well. And one of the things that I just started doing, which is working well and a tip I would give you is when I share the episode, I also include so my episodes are about half hour, 45 minutes. I'll share the link to the episode and whatever summary description. And then I'll add a thing that says, you know, make sure you don't miss this must see moment at the 22 minute mark or whatever it is, and have so I actually have two links. I have a link to the full video. And then I have a link to that minute of the thing. And what's really interesting, I'm actually just pulling up right now. This week's one what I've seen is so okay, so here's an example. So the one the email I sent yesterday in my newsletter promoting this week's episode. I'll actually read you, which was an episode with Roberto Blake who talks about YouTube and he shares a lot of great stuff. So here was my, I'll just read to you what my full, this was my full newsletter from yesterday, I guess it was. It says, Roberto Blake is a YouTube expert with 500,000 subscribers. And he just told me the secrets to success on YouTube, what to do in your first 30 days and how to protect your mental health as a creator. If nothing else, check out what he said at the 3:56 mark. I've never heard another experts say it, okay? So that's what I sent. And I got 201 clicks on the episode, which the link copy was secrets of success on YouTube, right? So 201 people clicked that, 304 clicked the check to see the must see moment. So in total, I get you know, over 500 clicks to it, but a three to two ratio of people clicking for the must see moment. And I think this also, obviously that's a cheese, right? It's a little clickbaity, but not really. He did say something at that moment that I thought, you know, that I genuinely thought was interesting. And I hadn't heard anybody else say. I also think though, so I've consistently seen higher clicks on the must see moment than the full episode. And I think it also speaks to what I'm saying about people's time sensitivity, right? Oh, I wanna watch this podcast, but I'll get to it when I get to it. Oh, there's a must see moment. I'll click that right now. And it's probably going to take me 30 seconds or a minute or whatever. It's the time commitment, right? Like, there is an investment that this is so true of all content, right? Your decision to read or consume any piece of content or anything, even if it's free is a time investment. And people are factoring that in at all times. And I think to the extent that you can lessen that time commitment up front, they'll dive deeper if they like it and they're interested in it, right? If I know Arvid's newsletter is gonna take me a minute to look at, I'm just more likely to open it than if I know it's gonna take me 10 minutes or whatever, right? So I think that it's really time sensitivity is a huge thing. And I think a lot of people sort of overlook it and just think well if it's good enough if it's quality enough, that'll be great. And ironically like so people click and this I can't track I have no idea. But my guess is if they click that link for the must see moment and that 30 seconds or minute or whatever it is, is really good, they're gonna keep watching. It makes them more likely to watch the full thing or listen to it or whatever, right? It's, you know, I'm "selling the content" as opposed to just going, hey, I got a new podcast. Here it is. I think you'll like it.

That seems to be the most surprising part of this because when I think about sample content, I would just like take it out, put it in its own video, post that on YouTube or post it on Twitter and then link to the original. But if you link to the actual sample content within the video, you want people to watch, they're already there. Yeah, they're already there. They only need to scroll back. And they start from the beginning. And then they can watch the whole thing. And they probably won't mind listening to the most amazing part twice anyway. So it's really not a loss in there, right? That's a really good idea. Man, you're full of great ideas. Did you know? It's really cool. Thanks for all that.

Thank you! And by the way, I do both of those things, right? I still share clips. And I still do the traditional thing. But yeah, I literally it's just something I just stumbled on. Because you know, like you, it's like, alright, well, how do I want to promote this podcast and my newsletter? You know, the other thing I would say is, in the beginning, let me just look at that newsletter again. So in the beginning, the newsletters I would send to promote my podcast would be like, oh, in this week's episode in my I Want to Know podcast, bla, bla, bla, bla, bla, bla, bla. This one I don't even mention it's my podcast, right? Roberto Blake is a YouTube expert. 500 subscribers, just told me the secrets to success on YouTube. I don't mention it's from and again, theoretically, I think people hear podcast and they go, I don't listen to podcasts or that's long or I don't have time to whatever. By the way, I'd say that's the other thing about writing these one paragraph daily newsletters was a really, it has been a really interesting exercise because it has forced me to think about how little I actually need to tell people in summarizing the thing, right? So a perfect example, like if this like, do I need to mention that this is from my podcast? That this doesn't matter. Like what is the real essence of what matters here? And that is always, you know, what is the sort of immediate value for those people. And it's made me realize how much even in short summaries, right? Like how much kind of fluff there is in stuff, right? Does it matter? You know, if I'm sending if I find an article, oh, here's a good example, right? Let's say I was linking to something you wrote, right? Does it matter in that summary that this is from Arvid? This is from The Bootstrapped Founder? Or does it just matter what it's about, and people will go there and see that it's Arvid and see that it's whatever, right? So really trying to remove so much of that stuff has been interesting. And I think also part of why people like it, right? It just gets straight to the point.

There you have this empathy with the needs of your audience, like, it's very noticeable when I look at your emails because you cut away all the stuff that is just like extra context that is not really needed. I mean, it's nice to have the context of who wrote this, or where it lives, or what format it is. But hey, if it's a podcast and you click on it and you don't have time to listen to it, now, that's alright. You'll find time later, but you already clicked on it. It's somewhere in your circle of what you can do with it, right? You don't pre decide that auto, I don't have time to listen to a podcast now. And then you don't click it. So you never see what was in there for you. So it's a much more interesting way of presenting information. And I think people want the information. They don't want the context, which is why I think this empathy level. And you have this concept that I find very interesting is that you understand the difference between what people want to consume and what creators want to create. And then you err on the side of what people actually want to consume. Because as creators, like I said, I write these things because that's what I want to write. But maybe people want to consume this in a different format. So I have to think about that, which is why I even started a podcast. Somebody told me, hey, I love your text. I love your gigantic essay, but I have no time to actually read it. But I do commute. So if you put this like in an audio format, I might actually listen to it on my way to work, which is why I started and now here I am. So it's kind of thanks to that person, I guess. But it's just understanding what people want and what people need, right? Now, it's bizarre but I love how you do this.

I mean, thank you first of all and yes, I'm always thinking sort of audience first and also relevant. So I'll tell you, this is a perfect example. And I say I don't mean to criticize a lot of people with their newsletters, but they're probably going about to feel criticized. But you know, I'm so amazed at there's some things that you see over and over again that have become not standard practice necessarily, but very common. And I look at them. And I'm like, I don't know why people are doing this, right? So the first thing is people that like in their newsletter intro hello, to my 26 new subscribers! Why does the reader care? Good for you, I'm happy you got 26 new subscribers. I understand what you're trying to do. That's a waste of the readers' time, that provides no value to them whatsoever. They don't care, right? The other thing is, you see a lot of newsletters where they spend, you know, the first two paragraphs, I'm telling you what they're about to tell you. You're just length, you know, in this issue, we're gonna talk about blah, blah, blah, and you know, 1, 2, 3, 4 , 5. Well, people understand, they can just scroll down and see 1, 2, 3, 4, 5. Like, you're just wasting time and lengthening your newsletter. And what's funny is, you know, their intentions, they think their intentions are to help the reader, right? That's why they're putting that in there. I want to give people a summary, I want to let them know what's in this thing. Their intentions are not bad. But I think if you step back, it's like, why do you need to tell people what you're about to tell them when it'd be better to just get right to what you're, you know, get right to telling them that? The other thing I always find interesting is, and this again, goes back to newsletter length, like I'll talk to some people. And they'll go, oh, I could never, you know, I can never publish this more than twice a month. And then you look at their newsletter. And it's like a novel. I'm like, why don't you just cut this in half and publish each half weekly? I don't mean like one long article. I mean, like, they're sharing 25 different things. And I'm like, you could probably easily just cut it in half. Like nobody needs 25 things twice a month, you know, share, you know, five things once a week. And it'll be better both for them and you. So yeah, I think it's tricky and look different audiences want different things. But I do think it's really important to sort of check everything that you're doing and going like, is this actually helping people? Like, why would the reader care about this? And I should add the, you know, that doesn't mean you can't sell in your newsletter and promote your products because theoretically, your products and services should be helping them and people should care about them, right? So just because it's in your best interest, doesn't mean it's not in your audience best interest as well, right? So this is not a don't ever promote your stuff in your newsletter thing. This is, you know, look at every element and go and by the way, like, this is an evolution. I've been doing my newsletter for six years, right? So I used to have a bunch of that stuff. I used to have a, you know, random photo at the top. I used to have a quote at the top. And then I started looking at it and was like, and this goes back to interesting versus valuable. I was like, is this quote really helping my reader? Like yeah, it's an interesting quote. But every week, I have to find a quote. I don't know that it really matters. Like, you know, is my newsletter less valuable? Because I don't have some random cool photo I found on Unsplash. Like, probably not, you know. And so there's lots of those things that you know, that are adding time that you have to spend creating, but probably not necessarily adding any value.

Yeah, let's talk about this. I think you've been on this journey, building a media business and you recently shared, like the things you do and all the little parts of it. And I find that very interesting because it pretty much mirrors what I'm doing. And I'm wondering for somebody who's starting out or somebody who's just like building a business and they want to reach an audience or they just want to start, you know, figuring out what they have to say and what they're interested in. And maybe they found something and now they want to build a media empire themselves. With a podcast and a newsletter and social media presence and info products and courses and all that stuff looming, like where do you start? Like, how do you go about this? What are priorities? How would you do this now if you were to start from fresh?

So a couple of things. So the first thing I would say is most of this stuff, "stuff" that we do newsletters, Twitter content, blogs, courses, most of these things are tools, not goals in themselves. So a lot of times I would talk to people and they go, I gotta get more followers. I gotta get more newsletter subscribers, I gotta whatever and I was like, for what, right? So like, what are you? I would it's funny, I do a lot of like social media consulting and when I used to have initial conversations with people, I'd be like, alright, let's talk about what your goals are. And you can't mention the words social media or followers, like what are you actually trying to accomplish separate from all this stuff? So that's always my first question, right? Like, what is your goal? What do you want to do, right? Then with that, I would say, okay, who do you need? The next question is, who do you need to reach to accomplish that goal, right? The question after that is what do those people value? Now what do you want to create? You have this goal that you want and I'm not talking about art now. I'm talking about business, right? So your goal is you want to do X, Y, and Z, you need to reach these people. Those people value this. How can you provide that value to those people for free, right? So now your content and there's lots of different ways, right? But you know, you might go, okay, I can provide that value to them on Twitter by sharing these kinds of tips or in a newsletter by doing this or a podcast by doing this or whatever, right? But this goes back to alignment, right? If you answer those questions in that order, you wind up with alignment between your content, your audience and an audience that ultimately aligns with your goal, right? So that's where I would start with most people. And then you can get into which tools am I going to use. And the other thing I would say about tools, especially when you're starting out, most people try to do way too much stuff. One social media platform, I always recommend a newsletter because I think emails the strongest connection you can have to an audience. So that's where I would recommend that most people start. And in terms of content and what do I talk about, I think an easy way to start for people who really aren't sure is, you know, now that you know who your audience is that you're trying to reach and you know what they value and what they want, just start by making a list of 20-30 questions that those people have actionable stuff that's going to help them get from point A to point B and just start creating content, whatever format around those things and then you're at least on your way.

That sounds like a really good strategy, very audience centric, very straightforward, not too many things at the same time, and focused on solving actual problems. I love that. I'm a big fan of that.

I was gonna say it echoes your Embedded Entrepreneur. You wrote a whole book about it, which I loved by the way.

And that's the whole point, right? The point is to figure out different ways of essentially giving people the right tools and your approach and your description of it is I think, just as not, if not even nicer than mine, so I love it. I really enjoy it. Man, thanks so much for being on today. That was really sweet. If people wanna find out more about you, if they wanna talk to you or hear from you, where would they go?

They can go to They can get my newsletter there or go to I'm also on Twitter, as you know all the time, @jspector and my podcast is on all the platforms. It's called, I Want To Know. You can also go to to see it and see some different episode highlights and that kind of stuff.

I highly recommend it. Thanks so much for being on the show today, Josh.

Yeah, thank you for having me. It's great to actually see you in person. And yeah, I feel like we've known each other on Twitter for a long time. And this is taking our relationship to the next level.

That's right, we're leveling up. Thanks so much for being on.

Yeah, exactly. Thanks.

And that's it for today. Thank you for listening to The Bootstrapped Founder. You can find me on Twitter @arvidkahl. You'll find my books and my twitter course there as well. If you wanna support me and the show, please subscribe to my YouTube channel, get the podcast in your podcast player of choice and leave a rating and a review by going to ( Any of this will really help the show. Thank you so much for listening and have a wonderful day. Bye bye