Skyrocket your newsletter growth with Dan Oshinsky


In this episode, Dan Oshinsky shares his insights on proven growth tactics for publishers and content creators. He breaks down strategies that work at different stages, from just starting out to having over 1 million subscribers. Dan provides tips on optimizing signup forms, using lead magnets, referral programs, contests, earned media, paid acquisition, and more.

Key Timestamps

01:41 – Dan’s epic guide of 52 ways to grow your email list

02:09 – What are some foundational principles of growth?

05:46 – Creating a compelling “why subscribe” message.

06:37 – Create a newsletter landing page.

07:30 – Publishers need signup forms in multiple places

11:41 – Adding signup form at 25%, 50%, 75% and 100% for long articles

15:24 – What are some of the best growth tips for a list with 10K people?

17:47 – Contests and giveaways to get signups and engagement from readers.

23:42 – Lead magnets work well for publishers of any size.

28:04 – Referral programs work best above 10-25k subscribers.

39:25 – Are there growth tactics that you’d like to share for publishers in the 10K to 100K range?

41:44 – How does using brackets work to grow your list?

48:39 – Let’s go to one million subscribers. What tactics work at this stage?

55:53 – What’s one uncommon growth tip you like that you wish you’d see more often?

58:15 – What’s your favorite ESP and why?

01:01:20 – What’s your favorite must-read newsletter?

01:02:09 – What’s your favorite piece of advice for a new set of publishers?

Show Notes

Inbox Collective

The New Yorker


52 Ways to Grow Your Email List

Nathan Barry







Spark Loops


Madison Minutes

Tone Madison

Charlotte Ledger

Berkshire Eagle



Second Street

Google Forms



Dan Oshinsky/@danoshinsky

Inbox Collective


Lesley Sim Twitter

Lesley Sim Website

Stay in touch

Apple Podcasts


Twitter Website



If you’re a news or media publication running on WordPress, check out Newsletter Glue. It cuts your newsletter publishing time in half, and enables you to manage your entire newsletter ops in WordPress. Go to to learn more.


Welcome to Sticky, the podcast that helps you build a must-read newsletter through actionable case studies and playbooks. Today’s guest is Dan Oshinsky. Dan runs Inbox Collective, which is a consultancy that helps news organizations, nonprofits and brands build loyal audiences via email and then converts that audience into subscribers, members or donors. He also runs one of the best curated lists of newsletter news, I can’t really call it a newsletter,


not a newsletter. It’s called that because it’s so long, it can’t fit into an actual newsletter and it’s actually a monthly Google Doc full of the latest articles and updates from the newsletter industry. If you’re not already subscribed, you really, really should get on that. Before that, he was the director of newsletters at both The New Yorker and BuzzFeed. And I’m really happy to say that Dan’s a friend and he’s been a supporter of newsletter glue since the beginning.


In fact, he was the one that got me off my ass to start an affiliate program. And he’s one of the kindest and most knowledgeable people in the world of newsletters and I’m so excited to have him on the show. Hey Dan, so glad to have you on the podcast. Hey Lesley, thanks for having me. That was a very, very, it’s a very kind intro. It’s been fun to watch newsletter glue grow and excited to be here on the podcast. Yay. So today we’re going to talk about growth tactics.


from small, medium and large publishers. Because you recently published this epic 50 plus, was it 52 or something? 52 ways to grow your email list. It took… 52 years. A long time to write the article. Yeah, I was reading it and it was really, really comprehensive. And there’s so many tips on that, that I kind of wanted to break it down for our listeners, so that whether they are at 1K, 10K…


100k or even a million, there are specific tips that work best for them. So let’s start. I want to kick things off with the basics. What are some foundational principles of growth that we should cover before we dive into the specific tactics? So there’s a few things that I want to say upfront about growth. One is, not everyone needs to grow fast.


And I think for a lot of newsletters, this is a struggle because there are some amazing examples of newsletter first businesses and big news organizations and nonprofits and independent operators who have grown their list in amazing ways. And it’s really easy to feel jealous when you see somebody else doing well or that thing of


somebody else launches a newsletter and you’ve been at it for a while and then you see them growing quickly and you’re like, no, but our newsletter is really good. Why aren’t we growing the way that they are? A lot of it depends on what kind of business you run. So for someone like me, you know, I run a consulting business. My business is mostly monetized through getting people to become clients. And so when I first launched Inbox Collective in 2019,


I went back and looked, I had about 1,750 email subscribers. And that was more than enough to launch a successful consulting business, because there were enough readers who said, we wanna work with you, Dan. We’d love to work with you. And I could charge pretty high price points for them to work with me. Oh, you want me to do this audit or this research or this work or consulting? Great, here’s what I charge. Newsletters that monetize through subscriptions or memberships or donations,


often have smaller audiences, but can monetize really well because one person might say, you know, yeah, I love your newsletter. I wanna pay a hundred dollars a year for it. Or I wanna make a thousand dollar donation to your newsletter. Fantastic. A consultant like me can monetize in different ways. If you’re selling a product, like I love the story that Nathan Barry at ConvertKit tells about how he got into email. He said, you know, he was a designer on the…


iOS side, he was designing iPhone apps, and he had a small email list and built this guide to building out your first iPhone app, and he sold a ton of these digital guides. He realized, oh my goodness, I should get out of the iPhone app designing game and into the email game because email sold so many of these guides for me. Now


If you’re monetizing through something like ads or affiliate revenue, you may need to scale up your audience to make the revenue you want. But it’s important to note first off, you know, do I need to grow and how fast do I need to grow? Monetizing through ads, you probably have to grow a little bit faster. Monetizing through affiliates, a little bit faster. Monetizing through subscriptions, you might be able to grow a little bit more slowly. Not everyone needs to grow fast. And two is, before you start to think about the tactics, make sure you understand the


the why. Why should someone subscribe to this thing? So many organizations, especially newsrooms that I work with, when I start consulting with them will look at their sign-up forms and they’ll say on every page and they’ll say, you know, Dan, we’ve tried all these tactics, we’ve looked through the list, nothing works for us. And then we’ll go to their page, you know, they’ll have a sign-up box at the bottom of a story or a pop-up, something like that. And we’ll look at the language and the call to action is sign up for our newsletter.


No context, no details, no other information. When do I get it? Why should I get it? Why should I make time for this in my inbox? I go, I don’t think you have a promotional problem in terms of the spots. You’re promoting in a lot of the right places, but the message isn’t there. We have to give people the why. Why does someone subscribe? The newsletter is gonna create some sort of value for them. It’s gonna impact their life in a positive way. There’s gonna be some sort of…


emotional connection, it’s going to strike kind of an emotional chord. Or maybe they just like you and want to follow your work. And so as you’re thinking through, you know, why should someone subscribe? Why should they make time for this in their inbox? Starting with that why is really important. And then once you have that, you can start to figure out, okay, how do we take that message, that core message, that thing that someone says, yes, this is great, give me more of this, and then figure out


how to get in front of the right people and how to convert them to subscribers. So to actually answer your question in terms of the tactics, once you’ve figured out the why, once you figured out how fast you need to grow, that’s where I’d start thinking about a few things. One is that everyone should create a main newsletter landing page. Now, depending on your platform, a lot of email platforms like Beehiiv or Substack, these are built in. Other platforms, they’re really easy to create.


If you’re on WordPress or even using a tool like Carrd, which I really like, you can create a landing page super easily. But give them the basics. What’s in the newsletter? Why should I subscribe and what’s the value for me? How often is it going to show up? Maybe you want to showcase a sample of the product. I always like doing the kind of screenshot of the product. Use a tool like Canva to create one really quickly.


I prefer to do that as opposed to linking out to other places because if someone can leave the page and go, for instance, read a sample version of the newsletter, they might read it and then not actually end up subscribing. So I don’t want to give them too many choices on that landing page. They should either be able to sign up or they should click the X and leave the page. Those are really the only options. And then over time, we might want to add other stuff. Maybe it’s testimonials. Maybe we want to add additional signups through other newsletters as we launch more, but…


that main newsletter sign-up page is huge because once you have that, you can start to deploy it in other ways. If you have a website that you’re building out like me, you’re gonna wanna put calls to action in your header or your nav, the menu bar, add something to the footer. It’s really easy real estate. The number of people who make it to the footer isn’t huge, but I find with just about every client that I work with, I see this on my own site too.


the conversion rates on those footer units is really high because usually if you get down to the footer, you’re looking for something specific. You’re looking to find something. Yeah, it’s like they wanna commit, but they don’t wanna commit too much and the newsletter is kind of the perfect amount of commitment. It’s a really nice place to have it. And plus if it’s on the footer or in the header, you have a sign up on every page. So that worry of, you know, so many organizations, they’ll start by, for instance, putting a sign up box on their homepage. And that’s fine.


But the issue for many big publishers, nonprofits are like this too, often the traffic isn’t going to their homepage. People are coming via a story that got shared or they were searching for something and got directed directly to a story page or an article page or a petition or whatever it is. And so if you don’t have signup boxes on those pages, well, we’re missing out. The homepage is just one entry point to your website. So header and footer is great.


And then the other thing that I always recommend to new publishers in particular is make sure you have some sort of call to action on the story itself. That could be, you know, something as small as a line of text at the top of the story. You know, want more stories like this in your inbox? Sign up for our newsletter. It can be something on the right rail, you know, a sign up box. It can be in the middle or bottom of the story. It could be a pop-up or a toaster unit, but there should be some sort of call to action as you’re reading the story.


and be thinking too about where and when you want to deploy these. So for instance, when I was at BuzzFeed, we were strongly against basically any tactic that would annoy a reader. We didn’t do slideshows, which at the time when I first joined BuzzFeed in 2012, were super common on the internet, and the reason was the incentive was around page views. Every media website in the world…


They said, we just got to get as many page views as we can so we can serve as many ads as we can. And at Buzzfeed we said, people hate clicking through those slideshows, click, click, click, click, click, you know, find stuff. It’s really annoying. We’re gonna build these sorts of slideshows as lists so people can just scroll through it and read. That’ll be way better. People will spend more time on the website. They’ll read more cause our reading experience is better. It’s also part of the reason at the time we didn’t do things like pop-ups. We were afraid of annoying readers, but-


Our articles were usually relatively short, so we made sure that we deployed calls to actions in a few different places. We found that two places, one, at the bottom of stories were really, really effective on something like a DIY or a food article. If you got to the bottom of one of those and we told you good news, you can get more great stories like this twice a week in your inbox. The signup rates were really high. We also built some house ad spaces around the website. So on every page, there was always…


different headlines driving people to different sorts of newsletter signups. When I got to the New Yorker, we started using pop-ups and we were pretty careful about where we wanted to deploy those for us because the articles were so long. Some New York articles are 10 or 15,000 words long. So having a signup box at the bottom of the story is great, but not everyone finishes the story, so pop-ups became really important and we thought about where to test those on longer articles. We tested them at about.


25%, 50%, 75% in the end, and they’re continuing to test this today. But at the time, we were usually running them somewhere between about 25% and 50% of the way down the page and using some of the time on site data to make sure, okay, are people actually reading enough that they’re going to see the sign up box? Because if someone reads a story and they only read for two minutes and that sign up box or that pop up appears.


three or four minutes in. 5,000 words. Yeah. Then they didn’t see it in the first place and we missed out on the opportunity to get them to come back. So utilizing that site data is super, super important. And so for a publisher, sign up pages, header, footer, something on the website too, as you’re reading an actual story, is it a pop-up? Is it something at the bottom of a story? Something in line, something on the right rail? That…


to me are table stakes. That’s what every publisher should be starting with. But let’s keep going, because there’s a lot more you can do beyond that. So what I’m hearing is if you’re a 1K publisher, you should basically be doing this table stakes, right? You need a landing page for a newsletter, and then you also need for all your other assets to have enough calls to action and subscription forms so that people can actually subscribe to the thing, right? Yeah. Nice. Yeah. And the good thing is about…


for a publisher, setting some of these things up is relatively straightforward. There are so many tools now, like an OptinMonster or Poptin or WPForms if you’re on WordPress, that are really easy to set up and deploy. Adding something to your footer, on my website I use WPForms, it’s great. I bought a subscription to it, a license for it. It’s relatively inexpensive. Set it up, created a unit, put it at the bottom in the footer.


and it’s there and I get a report every week about, you know, every week for me and my website is relatively small compared to a big news publisher, but every week a couple dozen people find that footer and sign up. I’m happy about that because, you know, based on the site traffic that I get, there are consistently conversions coming through there. It was something that took me five minutes to set up and I see the return on it every week. Same thing with something at the bottom of a story or a pop-up. Relatively easy to set up. You can use third-party tools that don’t cost a ton.


and then have something running that’s collecting signups. Then you can make it better over time. Once you have some of that baseline data, hey, this pop-up is converting at a half a percent of people who see it are converting, great. Let’s test out a different version and see if we can get the conversion rate to 0.75% or 1% or higher, can we do better? Yeah, okay, so I feel like just to be clear to people listening.


doing stuff like testing is like very far out of the 1k subscriber. Oh yes. So if you’re just getting started, you’re not running like big A-B tests. Not there. Because I feel like yeah, A-B test is something that sounds really sexy that like people always want to do and like think is really important. But if you aren’t getting enough traffic to do it, like you get so much more out of just reading a book or a really good blog article on how to convert and how to do copywriting and just following those best practices, then…


trying to set up A-B testing and going down that rabbit hole. Oh yeah, that’s something we’ll get to in a little bit, but once you get to that 50K, 100K and beyond, that’s where you really start to think around, okay, some of the audience has seen these sorts of calls to actions. What else could we do? What else could we try? Let’s update the message. Let’s update the design. Let’s see if there’s a better version of this kind of signup box or landing page that we could create. But at the start, I just want something that exists. Yeah.


And that’s okay. So let’s go to 10K now. What are some of the best growth tips for 10K people? So there’s some really interesting stuff happening right now in the newsletter landscape. There’s basic stuff that you can try. Things like, you know, encouraging readers to share the newsletter with a friend. A small call to action that says, hey, you know, do you have a friend who might like this? Click this button, share it with them. Pops open a pre-written email and they can just enter their friend’s email address, hit send. A recommendation.


engines are out there. So depending on what tool you’re using, if you’re on something like Behiiv or Substack that have these built in, great. A lot of the independent writers in particular that I talk to are seeing great returns from these newsletter to newsletter recommendations. These also can exist from organizations that aren’t on one of those platforms. You can use a tool like Spark Loops, Upscribe to recommend other newsletters and have other newsletters recommend you.


You could just think about direct outreach and cross promotion. I like that the best. Hey, we have a newsletter, I mean, a great example of this from Madison, Wisconsin. There’s a great newsletter up there called Madison Minutes. They have a daily newsletter. There’s an alt weekly in town called Tone Madison and they have a partnership. Madison Minutes highlights events that Tone Madison has recommended with a link out to sign up for their newsletter and Tone Madison on some of their stories recommends back Madison Minutes. They…


both serve the community. They do different sorts of things. One is daily news, one is arts and culture, and together they help each other grow. And partnerships like that might exist. And so finding other partners, those could be other news organizations, other writers in your space. A lot of the local newsletters that I talk to, they’ll find businesses in the community that might have some sort of reach. Hey, maybe it’s the local theater or…


the music venue or just a big restaurant in town or an influencer maybe who has some sort of audience. Can we partner with them to do some sort of recommendations? And that’s really, really huge. And so you wanna think about stuff like that and those recommendation engines can be really, really helpful, cross-motion can be really, really helpful. And then as we start to go from, you know, 10K and beyond I start to think about other stuff like contests or giveaways. Now with these, we wanna be really careful about


you know, which ones you want to do first. A great example from this, I had this listed in my big guide, but Wesley Verhoeven, who’s a photographer based in the Netherlands, fabulous guy, who also took the headshots on my website. Lovely guy, thank you, Wesley. But he has a great newsletter called Process, all about photography. And every single week in his newsletter, Wesley does this small giveaway. And it’s all photography related stuff. He gets sponsors for it, so the sponsors give him the stuff for free. I’m giving away,


black and white film or socks that are like photography related or some sort of print from a photographer, something that’s photography related, if you’re subscribed to the newsletter, you’re automatically entered to win. If not, sign up right now. And then he has a little caveat in his where he asks people to leave a comment or reply to the newsletter and that engagement triggers the like the entry. But I see this with a lot of


organizations, let’s give away something and let people sign up as long as it’s relevant to your newsletter. And as long as it’s not, I’m going to say this, as long as it’s not too attractive of an offer, like I was in Philadelphia the other day and I saw this billboard driving through downtown Philadelphia for a law firm in Philly. Philly, for whatever reason, has a very competitive


law business. There’s all these different personal injury lawyers and they all have billboards. I’ve never really seen anything like it except in Philly. There’s all these companies that are all trying to compete for your attention. How do they get your attention? This one company had a thing they said, Taylor Swift is coming. Actually, I think the concerts were last week in Philadelphia, but Taylor Swift is coming and if you follow us on Instagram, you’ll be entered to win.


Taylor Swift tickets. Oh no. And, no this has nothing to do with newsletters, but I saw that and went, they’re going to get a ton of people who follow the… And they’re not like qualified leads, right? Yeah. None of these people are going to turn into leads though, because, you know, the person who wants to get a Taylor Swift ticket and the person who says, I was injured and need a lawyer…


Maybe there’s an overlap, but that’s just a… Unless they know something about that Taylor Swift concert that we don’t. Yeah, unless they were thinking there might be like accidents or shoving or a stampede at the Taylor Swift concert. No, they’re doing what we would call in the business the spray and pray kind of approach, which is like, let’s get it as wide as possible than just like, please, let’s hope that somebody shows up. And so that doesn’t really work, but small giveaways, tickets, gift cards, restaurant…


Stuff like that might be useful. And you may want to clean your list too as part of the process, because sometimes people will sign up, but then they only wanted the reward. That’s valuable. I feel like you said that kind of like as a throwaway comment, but that’s almost like 50% of the tactic in my mind. Like it has to be contest and this cleaning together, right? Like you can’t do it. You can’t just do the contest because the yeah, what will happen is you have horrible.


stats and the quality of your readership would just decline dramatically over time. Oh absolutely, and I think for a lot of organizations, if you’re doing a contest, for instance, a lot of the independent newsletters look at something like a morning brew or the skim or the gist, doing great stuff, they’ll often do these big giveaways. Hey, enter to win a trip to Fiji. Now entering a win to win a trip to Fiji has nothing to do with reading a daily newsletter


So the goal there is we’re gonna partner with five other big newsletters. We’re gonna build this big pool of email addresses. We’re gonna drive all these registrations and then we’re gonna add them to our list and we’ll keep the ones who engage and we’ll drop the ones who don’t. The bigger the giveaway, the more aggressive you have to be in pruning your list afterwards, checking to see are people opening? Are they clicking? The ones who aren’t, we may wanna try to win them back or we might just let them go. And you know, a lot of the…


organizations that I talk to, if they’re doing a big kind of contest or giveaway, especially some sort of co-registration with other organizations, the conversion rate on those might be as low, not always, but might be as low as 10%. You know, 10% of the email addresses that come through actually stick around. Sometimes they’re as high as 40 or 50%. Smaller contests might be even higher. But in that case, where, you know, in a good one, 50% of people who signed up to win that trip to Fiji…


stick around, that’d be great, but it means that half the people are going to go away. And so you have to be a little bit aggressive about saying, all right, these people signed up, they just wanted the trip. They don’t want our newsletter. Let’s be willing to let them go. Other stuff that’s out there. Referral programs are definitely out there. Hey, I’m going to refer a couple of friends in exchange for something. Could be, you know, entrance into giveaway, some sort of sweepstakes, some sort of contest. It could be for some sort of digital reward.


digital download, access to a premium newsletter, you can get creative with those sorts of things, those still can drive returns, not quite at the levels they did 10 years ago, five years ago, but they are still, there is some value there, even getting people to share the newsletter with two or three friends, there’s certainly value there. Other stuff that I’m thinking about, getting people to engage and then convert, so that might mean stuff like, running a survey on your website, asking questions, then at the end saying,


Do you want to sign up for our newsletter? That’s actually a really good way to convert people over from social media or who are reading your website. They’re not on the email list. They answered some questions. They’re pretty engaged. Ask them to convert. Maybe we want to think about things like, you know, user generated content. Hey, ask us a question in this form, send a letter to the editor. And then in the process, check a box, sign up for our newsletter. If we’re getting your email address, why not?


The one other thing that’s out there for a lot of organizations at this kind of level are lead magnets as well. So I’m going to put together whether it’s an email course, whether it’s a downloadable PDF, here’s this really good piece of content. Do you want to trade your email address for free access to the content? That often does really, really well. And just with lead magnets, would you say that this is something only someone at 10K and beyond should try? Because I kind of feel that this could work really well with a 1K.


Oh, absolutely. I work with publishers who are smaller who use these two. Often the issue with the 1K publishers is they just don’t have the time to do it because they’re so busy, they’re so focused on all these other things, you know, growing their email list and publishing articles on a regular basis and all the other things. But yeah, if I work with people who, out of the geek, when they launch, that’s the first thing they have is…


You know, let me trade an email address for access to this course or guide or resource that I built. So yeah, if you can do it sooner, absolutely. There’s not a, you don’t have to wait. With any of these tactics, by the way. I feel like you can do one great lead magnet when you’re just starting out. If you’re larger, you can do, you know, 10 or you can do like one for every single blog post if you want to go nuts with it. But, you know, if you do one lead magnet to start with.


and forgo writing blog posts and a whole bunch of other stuff. Like I think that could be a more valuable way to grow your list right out the gate. Absolutely. I mean, a great example of this from the independent space, there’s a guy I work with, Kevin Friedberg, who has a newsletter and website called Seven Second Websites. It’s all around how you write the first seven seconds of your website to make it as good as possible to convert people. And he built this, you know, it’s a short week long boot camp that’s delivered via email with tips and resources.


And that’s the focal point for his newsletter. And he’s just starting to build up his audience, but that bootcamp, that lead magnet is the thing that he’s using to drive conversions and grow his audience. And so, yeah, it’s exactly that. A great example, Leslie, to your point of, let’s put my attention to a really good thing upfront. I’m gonna build it once, and then it’s gonna drive a lot of conversions and signups over time. And then I can worry about…


The weekly articles or the guides are optimized in my website later on. That’s also a perfectly fine way to go.


Newsletter Glue cuts your publishing time in half by enabling your team to publish newsletters the way you publish articles in WordPress. Find out more at Now back to the episode. More than anything else, I think, as we talk through this, if you take something away from this, there’s lots of different ways to grow your email list. You have to make sure you have some sort of clear why statement, why is this valuable? But also the stuff that works for other people.


or in the order that worked for other people may not work for you. I see so many organizations that say, we’re so similar to Morning Brew and we tried a referral program and it didn’t work. Is something wrong with us? And it’s like, no, it just may be your audience, your audience. You know, you’re trying these tactics and you, you built attractive swag or you have a really good lead magnet. Your audience may just not be super eager to share that sort of thing. That’s okay. Let’s move on to the next idea. There’s nothing.


maybe wrong with what you’re doing, it could just be that your audience isn’t engaging or isn’t taking the step that you want in the way that you thought. It’s okay. What’s next in the list? Like I said, we put together this list of 52 ways and there’s lots and lots and lots of effective ways to grow your email list. So if something doesn’t work, move on to the next thing. Don’t get discouraged. What works for one audience may not work for you or what works for you may not work for another person. That’s just kinda how it is.


I’d like to hear your thoughts on it as well, but to me, I feel like for certain tactics, you have to get to a certain level before you get to unlock the next level of tactics. So with certain things like referral programs and stuff, I would actively advise the 1K subscribers to stay away from them, just because it’s not… There are just so many reasons, it’s not important to go through all of them right now, but I think it’s important to know that the tactics that we’re talking about are kind of one-way streets. So in the sense that…


Like the million subscriber list should also be doing the things that 1K people do. Correct. But the 1K people should not be doing the same things that 1 million lists are doing. Correct. I mean, referral program is a great example of that because if you’re so small, you just don’t have enough people there yet that referral program is going to be super effective. You need to hit a certain level of scale. Usually the number is 10, 15, 20, 25K where you start to see the returns. So if you have


a thousand people on your list, it’s just not enough. Don’t give away swag or stuff at that stage. Just ask people to share it with a friend. You don’t give them a pre-written email. But there’s also things like paid acquisition, which as we get to the next year, is a super valuable tactic. Paid acquisition can be a really good thing at the start to help get you to that first thousand readers to test out the concept and make sure the voice is right and the content is connecting. But…


Most organizations don’t really start to invest in it as a core tactic until they’ve gotten a little bit bigger and know, all right, as we grow, you know, this next stage, we have 10,000 readers, if we can get to 25,000 readers, here’s what we can charge in terms of advertising, or here’s what kind of conversions we think we’re gonna see to our paid subscription. Once you have some more of that data and you know, there’s gonna be a return on this investment. Investing now leads to X down the road.


That’s where people really start to get into things like paid growth as opposed to organic channels like a sign up box or a form or a pop-up. Just because they know what the return is. And if you invest too much too quickly, you might find, oh, at this stage, actually I’m still testing the product. I’m still learning about what people want. And I realized that I’ve talked with so many newsletters, whether it’s a newsroom or independent operators who just go,


I realized we spent a bunch of money at the start and we really didn’t know if it was the right newsletter yet. We still had so many tweaks and tests and improvements we needed to make and so we grew the list. But we lost lots of folks because, well, the product wasn’t right yet. And you really want to make sure with certain things that, hey, if you’re going to spend your own money, is it the best possible newsletter? Is it great? Do you know it engages people for the long haul?


Do we know how we’re gonna monetize it in the right ways? Great, if we’d have answers, yes, let’s go out and start spending some money to help grow the list. But if you do it before, you may be throwing away money. So you’re absolutely right, you wanna level up as you go. You wanna, the people of million person lists, they still do things like have a link to their newsletter signup page in the signature of their emails. You know, they send out an email, a personal email. I got this the other day from a writer who joined my email list, who is a…


New York Times bestseller with a massive, massive audience. And there in her footer was a link to her newsletter signup page. It just made me so happy. It was like, this person’s got a million people on her email list and it’s still there. Every email she sends, by the way, sign up for my newsletter, it’s great. And so you still have to utilize those tactics. You just start to, as you grow, you get the opportunity to open up and try bigger or more aggressive things to scale.


Let’s go into our intermission. So I’ll ask a bunch of quick intro questions and you can answer with a single word or a sentence. Totally up to you. Ready? Let’s do it. Shake Shack or Russ and Daughters? Oh, Russ and Daughters. Absolutely. I mean, I have strong feelings about New York food, but the Russ and Daughters… It’s one of a handful of places you can get fishes like a pastrami, smoked.


piece of locks. It’s just a special and unique New York place. Russ and Daughters all the way. What’s your favorite international city? I love Copenhagen. I’m obsessed with that place. It’s so… The food is great and it’s beautiful and the people are super friendly and it’s easy to get around. Being in Copenhagen feels like you’re in the future. It just feels like the future we were all promised. It’s so great. I love it there. New York’s not bad either though. I’m pretty lucky to live here.


Outside of work, what’s something you’re really into? I will give the two answers, the answer you’re looking for, which is something that I actually do outside of the office. I got really into golf during the pandemic. It was a thing that I could do outside with friends that felt safe. And so I did a lot of that. I’m not good at golf, but I really like trying to get better at it. And there’s a part of me that…


golf really appeals to the like get a little bit better every month. There’s a part of me it’s like you know I learn a new thing like oh I know a new thing and also like in building a business it doesn’t happen linearly like I always think I’m good for a week or two and oh this is gonna how I’m gonna be forever. It’s like no it’s not really how it works like you get better at stuff and then things change and so it’s the testing and iteration and learning part of it really appeals to me plus I like being outside.


pretty fun. And then I also just love spending a lot of lazy time on the couch with my wife binging whatever we can binge. A lot of House Hunters and HGTV here in the US. We’re rewatching right now, 30 Rock, like Start to Finish. That’s been fun. I hadn’t watched that in 10 plus years. That’s been fun. Yeah, lazy time with my wife is a pretty good thing. I, in fact, put her above golf, just to be super clear when she listens to Sally, you are above golf in my book.


You’re the second person that I’ve recorded with that said golf. So I don’t know, maybe golf really took off over the pandemic. I know a lot of people who got into it. I played as a kid. It was always a really hard game. But then going out and playing and practicing and being outside, I was like, this is really nice. I like doing this. I’m not good. I don’t think I’ll ever be good. But I’ve gotten to a point where


I’m not terrible, but I’m not good at it. Somewhere in that in-between zone. It’s one of the only sports that you could just say like, oh wow, I play a lot and I’m just not good at it at all. And I love it. It’s so much fun. It’s an excuse to walk around, right? Go for a really nice walk. It’s not a bad excuse to get outside and walk and where I get to play here in New York, I usually walk, which is fun. Anytime you can go on a four or five, six mile walk outdoors on a nice day, it’s a pretty good day. Yeah.


What’s one favorite TV show from your childhood? Oh my goodness, I have so many. The one that I will say that I always wanted to be on and never got to be on, there was a show here in the US called Where in the World is Carmen Sandiego? I watched that. And I loved that show. There is still a part of me that likes playing, you know, like a Sporkle type of, you know, guess all the countries of the world kind of thing.


I just loved those. I always wanted to be on that show as a kid and run around with the fear that they were gonna You know ask you to pick some country That was really small like a tiny island and the kids would just be like I don’t know where Naoru is. It’s got to be over here somewhere. I know it’s by Australia. Where is it? And then just running around I always wanted to be on that one Would love to build a time machine where I got to go back and do that or maybe Just throwing throwing this out as an idea


The adult version of that, based on videos I’ve seen online, I feel like adults would be pretty bad at that game show too. I would watch a kids versus adults version of that game. Find things on a map. Okay, last question. If you could only drink water and one other drink for the rest of your life, what would that other drink be? Ooh, what would my one other drink be? If it’s not water, probably wouldn’t be milk. I’m lactose intolerant.


I don’t know if I could do orange juice every single day. I’m gonna go and I’m gonna say, I’m gonna go with an unconventional pick. I wouldn’t drink it all the time, but whenever I’m on flights, I always like to drink ginger ale. There’s something about ginger ale on a plane that always tastes right. I think I would be a little sad if in those moments on a plane, I could only drink water. I don’t drink ginger ale very often, pretty much only on planes.


But I fly enough that I think it would actually be a loss for me. I’m gonna go with the ginger ale final answer. Wow. So you’re not like a coffee or a tea person? I don’t drink coffee, which my wife luckily drinks all the coffee for us. She drinks enough coffee to, you know, when the Census Bureau comes around every year and asks us how much coffee are we drinking, are we supporting our local Starbucks enough? We’re doing enough of that, don’t worry. Sally does that enough for both of us.


I like tea, but I don’t need tea. I don’t really drink coffee. And I’m lactose intolerant, so I don’t drink a lot of milk. Ginger ale, it is. Orange juice sometimes, sometimes sodas, yeah. Root beer every once in a while. I mean, I could pick an alcoholic beverage, but to be honest, if you told me that I couldn’t drink beer anymore, I’d be okay. I wouldn’t be. I wouldn’t be devastated. That’s fine. Ha ha ha ha. Same, I kind of stopped drinking alcohol altogether over the pandemic, and I don’t miss it.


I will say that I will drink sometimes a lot of the non-alcoholic beers occasionally when it’s, you know, a weeknight and maybe my wife who works at a hospital will come back and she wants to drink something and we’ll just say like, I don’t really want to drink a beer but I kind of want to drink something that’s beer-like, like a non-alcoholic beer. I could do one of those, like a Heineken Zero, sure. Yeah. But I don’t, I don’t know.


I had a non-alcoholic IPA recently that was really good, and it tasted exactly like the real thing. So I’m glad that those options exist now. Yeah. Yeah, they’re really quite good. I can’t vouch for all the various non-alcoholic gins and tequilas. I haven’t gone through all of those, but the non-alcoholic beer is pretty good.


Let’s not put that as that’s a pretty poor endorsement, like Heineken Zero to have on a label. It’s pretty good. Yeah, I could see the billboard in Amsterdam as you’re driving through, my face. Non-alcoholic beer is pretty good. I drink it, it’s not bad. With the shrug. It’s fine. All right. So while we were talking, I put in some of the answers that you gave into chat.GBT and got it to write you a limerick. Oh boy. I’m going to read it out to you.


Okay. There once was a fellow named Dan, whose cravings for bagels began in a chase quite stupendous from San Diego to Copenhagen, searching the globe for Carmen’s clan. That’s pretty good. It is, huh? As someone who spent a fair amount of time as a kid going up to Nantucket, and that’s where most of my limerick-related rhymes are going, I’m pleased by this. This sounds good, and there was no cursing in it like all the Nantucket rhymes, so that was great.


So now you have a little souvenir from this podcast. Amazing.


So now we’re going from 10k to 100k. And to be clear now that the numbers are getting bigger, we were starting from zero to a thousand, and then a thousand to 10k. And now it’s everyone who is between 10k and 100k. So once you get into that 10k category, that’s where things like earned media really starts to come into play. So, hey, you’ve built an audience. You have expertise on a topic.


maybe you’re going to be able to go on. Today’s a great example of this for me. This for me is a piece of… Or media. Yes, to make it sound purely transactional, which this is not. But if this was, I’d look at this and go like, this podcast with Lesley, being here on the Sticky Podcast is a great way for me to get another 25 or 50 subscribers. It’s free, we’re having a conversation. Hopefully people learn and see here like, man, this DM guy knows a lot about newsletters. Let’s sign up for his newsletter.


That’s not how I’m thinking about this today, but this is a form of earned media, going on a podcast, writing a guest post for somebody else’s blog, getting a shout out in somebody else’s newsletter. That sort of thing really starts to add up as your audience grows a little bit because you have a wider reach and you have some influence and that can be really useful. Events and talks are definitely in that category as well. Often people have larger lists, start getting invited to do things like speak at a conference or…


do their own webinars or events where they might be able to attract people to come in and check their stuff out. Brackets and best of lists get really interesting at this stage. So I see, especially with publishers, once they’ve reached a certain level of scale, they might be doing things like… Charlotte Ledger does one of my favorites. Most people do a 40 under 40. They do a 40 over 40, the opposite. Instead of doing the young people, they say, what about the love for the people who have been in our community for a long time?


And they also do a great event every year tied to it, because of the ages that people are, if they’re over 40. The last couple of years, it’s been an 80s themed kind of event where people dress in 80s clothes, but they’re getting pretty close to where people born in the 1990s will be eligible for this. So they might have to change what the party looks like. But theirs is a big annual contest. People nominate their colleagues or other businesses, business owners for 40 over 40. They can check a box in the form to sign up.


They write stories about the winners. They do events tied to it, all these different things that bring folks in. Brackets, hey, voting on the best stuff in your community. The best pizza place, the best restaurant. This could be a big bracket vote on 20 different things. Yeah, look at a lot of the big magazines and organizations. Right, and so with the brackets, how does that work? So those are things like the Chicago Reader, they have literally like 100 plus categories that people vote on. It’s everything from best hamburger and best bar to certain best businesses in various categories.


And so they use a tool called Second Street to do these, but I see teams that use Google Forms or Typeform for something like that as well. People can first nominate a business, then there’s a round of voting where there might be a couple finalists. And in order to vote, you just have to…


check a box and sign up for the newsletter too as part of it. So that way. So you wanna support your local pizza place, you have to sign up for the newsletter. Correct. And they do that to make sure that people aren’t abusing it. They don’t want people just voting a million different times for the local pizza place. So the email address is a little bit of quality control. Now, any semi digitally savvy person can kind of figure out ways around entering different email addresses, but still. And the nice thing about those too is the local pizza place often goes on their Facebook page or they might have a QR code.


in the restaurant that goes, hey, we’ve been nominated for best of Chicago. Scan this QR code, go to the form, vote here. And then that business is promoting you. It’s a form of cross promotion, which is really, really cool. I just want to say that like, you know, we see these voting brackets really, really commonly with local news, but I feel like more businesses, like non-local news businesses, more niche newsletters could utilize this growth tactic.


Even if you were running a software company or a newsletter about aerospace, you could still do brackets. It’d still be really interesting and people would be really motivated to sign up and vote for, I mean, I don’t know that much about aerospace obviously, but their favorite space organization, international space organization or something. Because I always like seeing the brackets in the wild, kind of from a consumer spectator perspective.


And so I just love to see that happen more often. And even like for myself, I love to participate in more of those as well. I mean, I feel like for newsletter like mine, for instance, I haven’t done this, but if I wanted to do a newsletter of the year contest, I probably could. And get a sponsor for it. Or newsletter tools bracket that we go to. Absolutely. I think there’s tools, newsletters.


people who have done influential stuff in this space, there’s all sorts of things that I could do if I wanted to go down that rabbit hole. And so there’s certainly opportunities there. The one other thing for local publishers that I think, you know, you don’t need to start with a best of where it’s 50 different categories. I work with a newsroom in Western Massachusetts, the Berkshire Eagle. And during the Super Bowl, right before the Super Bowl here in the US, they did a big bracket around the best chicken wings in the area.


A lot of people order chicken wings while they watch the football game. And they saw great results and a couple hundred email signups from a pretty simple thing, which was a Google form that they embedded on their website, which is like, nominate your favorite chicken wing place and give us a sentence and tell us why. Also, do you want to sign up for our dining newsletter? So now they’re thinking about how we do more of these sorts of things throughout the year. Hey, it’s the best soft serve ice cream place because it’s summertime. Hey, it’s the best hiking trail because there’s a lot of hiking to do in their part of the country.


So anyone can use these sort of things as you go, and there’s certainly opportunities there. Are there other growth tactics that you like to share within this kind of 10 key, 100 key range? I think the one other thing that’s there, we mentioned earlier, but this is where organizations start to do a little bit more testing. So, hey, we’ve tested out a pop-up on our website, but now we wanna test out different marketing language or copy or when it appears.


We want to see what happens if we run the sign up box, not at the bottom of the story, but halfway through. That’s where you start to do a little bit of testing to figure out, all right, we have a lot of these tactics, but how do we make them better to allow us to continue to scale and grow and bring in the audience? Or we’ve rolled out things like an initial lead magnet, but now we’re gonna try another thing that we could have. We’ll have a second lead magnet or a fifth. This is also the place too where, for a lot of the newsrooms in particular,


One of the best things you can do to grow is not actually a tactic in terms of, you know, a sign up box or conversion unit, but just launching more newsletters. You may find that there’s an audience that says like, Hey, I like a daily newsletter and I want it. I, you know, I want a daily newsletter. It’s fantastic. But there’s many readers who go, I get a lot of stuff in my inbox. I don’t really want a daily newsletter. But if you launched a newsletter tied to my favorite writer that you have on staff or on a topic,


you know, give me a parenting newsletter or a weekly newsletter around dining in the area or events to do. Yeah, I’d sign up for that. And so not everyone wants the five day a week or seven day a week daily newsletter. There may be other things. And so at this stage of the game, this may be where you think about how do we launch other newsletters and recommend people from, you know, hey, you already like our daily newsletter? Sign up for a second thing or


you’re not on our newsletter yet, that’s okay. We have this new thing that we think you might like. Using a banner at the top of the page, sending out an email to the list, a new pop-up, and you know, announcing, hey, we have this thing, check it out. There are lots and lots of opportunities there. One more small thing too, as an aside, I mentioned earlier the idea of, you know, the restaurant shares the QR code, but this is also where businesses and, you know, local newsletters, big publishers start thinking about the IRL sort of thing. So,


Hey, we’re gonna do something where we go to the local farmer’s market, or we’re gonna have ads around town, posters that we’re gonna put up. I mean, here’s a publisher who’s using newsletter glue, Larry Hoffman down at Dine Sarasota in Florida, he said his newsletter’s all around dining and restaurants in Sarasota, Florida. What if I make some QR codes, put them on coasters and distribute them to local bars and restaurants? People will be at dinner, they’ll be at the bar.


the bartender will hand them their beer or wine, whatever it is, and the coaster, and they’ll look down, they’ll just be sitting while they’re waiting to order, and they’ll go, oh, look at this. There’s a newsletter about dining in the area. Scan the QR code and sign up right there. So that IRL stuff comes into play at this stage of the game too. Awesome. Yeah, Larry’s awesome. That’s such a great idea. Yeah, I loved when he did that. Just make sure if you’re doing those sorts of things.


use a UTM or a unique landing page so you can track the conversion. Because otherwise, you have no idea what’s working. You know, it’s just all go into this one sign up page. So, you know, create a spinoff landing page or have a UTM so we can see, all right, this many people came via this specific link. All right, let’s go to one million subscribers. So the infinity and beyond.


Yeah, and this 100k or beyond, frankly, anytime you get beyond 10k, you can start to do this, but paid acquisition is one of the most important things that’s out there. Now, you could think about direct kind of lead ads. So these might be, for instance, on Facebook, an ad that says, hey, sign up for our newsletter. Now you can do these in different formats. You can have a lot of the local newsletters that I work with. It’ll be the same kind of format. It’s an image of the skyline of their city.


There’s an image of the product on like a phone overlaid over that. And then a call to action that says, you know, sign up for our daily newsletter. Here’s what you get. It’s free. Fantastic. You could be creative. I see a lot of great examples of these out there. People using, they’ll write the ad and put it into the notes app and take a screenshot of that and use that as the kind of call to action. They’ll use videos. Those sorts of lead ads can be great. You can think about content to capture, which is


What if I promote a piece of content and then make that essentially gated content? So someone sees it on Facebook or another channel, or they see an ad on Google, they click through and they go to your website, they see a registration wall. It’s like, hey, this content’s free. You just have to sign up for our newsletter first to get access to it. Those can work. I see a lot of people doing these kind of like two or now it’s kind of like a three-step sort of conversion campaigns.


where they’ll drive people, they’ll have some sort of call to action that says, you know, sign up for our newsletter. But instead of collecting the email address on Facebook or wherever, they’ll drive people to their website. They’ll get them to sign up on a sign up page. And then Spark Loop built this thing called Upscribe. And there are a bunch of different newsletters that are in the Upscribe world that say like, hey, we’ll pay you for every email address you send our way. So people take someone from, all right, sign up for Dan’s newsletter about living in New York City.


go to my website, sign up, and then afterwards, there’s a pop-up that says, hey, there’s some other newsletters that I like too, check these out. And some of those newsletters are actually paying people after, you know, hey, if you drive any of your signups over to us, we’ll give you a dollar, two dollars, three dollars, whatever it is. So for many organizations, they’re finding, oh, this multi-step kind of campaign, we’ll drive people to our website, we’ll convert some of them, and then we’re actually gonna get paid on the backend. We might be able to lower.


our costs or even end up getting paid to drive email signups. That’s an option that’s out there too. So your paid acquisition becomes free potentially. Yeah, it’s potentially your cost per acquisition is as close to zero or maybe negative. You’re actually getting paid to integrate your email list, which is really, really fun. The one other thing that’s out there for publishers that I should have mentioned earlier, but as in particular for publishers, newsrooms, or anyone who has some sort of read revenue strategy like a nonprofit then does donations. After somebody


supports your work. They pay to subscribe to your digital publication. They donate to your organization. They become a member. Offer them the chance to sign up for newsletters as part of that. So many of the organizations that I work with, this was the case at the New Yorker, after you go and subscribe to the New Yorker, we showed you a couple of related newsletters that we thought you might like. And those were hugely, hugely useful ways to drive people to…


our newsletters, some of us, you know, a lot of the signups that came for our daily newsletter, the crossword newsletter, things like that, came via that post support page. We already had their email address, they already want to read our stuff because they’re paying us for a subscription, why don’t we get in front of them at that moment and say, hey, there’s some great ways right now that you can engage with our content. Click here, check this box and sign up for the newsletter. So that’s something I’d look at.


and paid really becomes a valuable thing at this stage of the game. As you start to grow and say, how do we reach the right audience? Oh, it’s through paid ads on Facebook. It’s advertising and other newsletters. It’s through recommendations. It’s through Upscribe. It’s through utilizing a lot of these tools together. It’s through, hey, we’re gonna use a combination of paid plus a lead magnet. We’re gonna drive people from a paid ad they saw on Instagram.


over to our website, they’re gonna sign up to get this lead magnet, and that’s gonna funnel them in. You start to mix and match these kind of things together, which is really fun. Cool, are there any other million list pieces of advice you have to give? I think we’ve gone through a lot of the basics. You wanna keep testing and trying stuff. Homepage units become really important. Some stuff that I will say as you get bigger, you start to think about just optimizing. So for instance, a lot of publishers, once they’ve reached a certain level of scale, will say, hey,


Maybe we can offer ways beyond an email address to sign someone up for our newsletter. So let’s use OAuth so someone can register via Facebook, LinkedIn, Apple, something like the Google, something like that to register for our newsletter. Maybe we’re going to start using house ads on our website to register people for our newsletters. Maybe someone’s already signed up for a subscription. We have their email address. We can do kind of check a box and sign up for a newsletter with a single click kind of units.


So you start to get creative in how you optimize and improve over time. What I find is once you’ve laid the foundation, sign up boxes, header, footer, sign up pages, pop-ups, doing some paid acquisition, a lot of this becomes around testing and improving the ways you convert people, as opposed to desperately searching for, oh God, we’ve tapped out of all the people who could possibly sign up on our website, what’s next? Like that’s not really the case. You’re always looking to improve.


at that stage of the game, not, there’s nobody left, we’ve gotten every possible sign up out of the footer. That’s not true. You know, there’s always gonna be more. It’s possible if you’re like a local publication in a town of 5,000 people and you have 5,000 people on your newsletter. Oh yeah, I mean, I remember having, and again, this comes back to being realistic about your goals or if you’re a local newsletter, how many people are in the community? There’s gonna be a limit on how big we can go.


I remember a couple years ago having a conversation with somebody who said their goal was to grow their newsletter, local newsletter, to 100,000 readers. But we looked it up. There were only 110,000 people who lived in their area. I told them, I think it’s great to have these big goals, but you have to be realistic. It’s probably not realistic to expect that 90 plus percent of people in the community are going to subscribe to your newsletter.


And if you were able to get 100,000 people on your list, it probably means there’s a lot of people in the email list who don’t have a connection to the local area who aren’t gonna stick around. So, you know, you have to set realistic goals. In a case like that, getting five or 10% of the community to subscribe to your newsletter would be an amazing success. It’d be a huge number of people. But it might mean that person says, the biggest our list can really be is five or 10,000 people. That’s okay. That’s great. If we get 10,000 people, we’ve done it. We’ve built a really big list.


Cool. So we’re going to end off with a bunch of quick recommendations from you. So I’ll just ask a bunch of questions and I hope to hear what you recommend. Yeah. So since you’ve been talking a whole bunch about growth tips, what’s one uncommon growth tip you like that you wish you’d see more often? So I’ll mention two. One is…


I mentioned earlier about surveys, I think are actually really underrated. I use this personally with my newsletter. I have my main newsletter, but then I have some side alerts that I can send you when I publish new articles. So in things like an end of the year survey or my welcome email survey, which I send about two months in, I ask a couple of questions. How am I doing? What can I do better? Anything, you know, open-ended feedback you wanna provide. And then also, hey, did you know I have these other newsletters you could sign up for, you know?


check the box, I’ll add them to you. You know, I add you to those lists. And those are actually really effective at driving signups because the people who fill out the forms are always like, yeah, I want more alerts around this topic or this topic, send me more. That’s out there. The other one that’s really fun and we’re starting to see is acquisition of newsletter products. So a lot of these newsletters will point to something like the Daily Up side has been doing a lot of this.


They’re going out and identifying other products that are in this landscape, you know, they’re doing well, and they cover a similar sort of topic or similar audience but a different topic and say, hey, this person’s over on an independent platform. They have 25,000 subscribers, they have 50,000 subscribers. Could we bring them into our world, have them be one of our products, we can do cross promotion across the newsletter and knowing what we know about growing and scaling an audience.


We think we can take them from 25,000 people, 50,000 people to 100,000 people really quickly. Because we have a pretty big audience and we can funnel a lot of those people down. So acquisition of existing engaged email list, not going out and just buying a bunch of random email addresses, but saying, hey, this person has a great newsletter. Could we bring them under our umbrella and find a way to work together? That’s something that I’m seeing a lot more newsletters in the space start to consider. And I think it’s actually really smart.


As long as that person’s going to stay on, write the product, engage with readers, you’re going to be thoughtful about how you grow and monetize it, there are opportunities there. Love that. All right, next question. What’s your favorite ESP and why? It’s funny. Earlier today, I was having a call with a potential advertiser, and they were saying, you know, we feel like from the outside, you try to…


act almost as Switzerland in the newsletter space. I was like, that’s exactly it. Like, I try not to say, you know, I’m sure the team at Mailchimp would love me to say, Mailchimp is all I need. Anyone who’s not on Mailchimp is an absolute fool. I really like Mailchimp. Great tool, highly recommend. But I can’t tell you that they are the only tool out there that’s good at sending emails. And there’s lots of these that are out there.


And it’s the reason earlier this year I published a guide to six different email platforms for independent writers. And I was like, any of these would be really good options. It depends on, you know, if you’re on a tool like Substack, it’s because you’ve said, hey, I love the recommendations tool and I think I can grow really quickly that way. So all I’m hearing is excuses. And what I want to know is which is your super biased, completely irrational ESP that you kind of have a soft spot for. I…


See, you’re asking me to do something that I don’t really have an opinion on. I’ll tell you that I use, here’s what I will say. I use Mailchimp on my own newsletter. And that’s because I use it most. It’s the ESP that I use like on a day to day the most. It’s the one that I have the most clients on. I’m most familiar with. And I like a lot of the features and it works for me. But if I was an independent writer, I might say like.


Look at an AWeber, look at ConvertKit, look at Beehive, look at Substack, a lot of different things there depending on how you’re monetizing. Oh, you’re monetizing through ads and need automations? ConvertKit’s a great option. Oh, you’re really focused on growing your audience but want no fees? Beehive is a really good option. Oh, you don’t have any money to put into like an email platform but you’re trying to grow subscriptions? Substack’s a great option. AWeber has some really good design tools. Like…


I, on a daily basis, get these questions from readers and funnel them towards any of like nine different ESPs that I like because there are truly, I think this is the best part of this space, there are a lot of really good options right now and competition among these platforms has forced all of them to step up their game. There are really at this point only a handful of ones that I say, I’m not going to name them here and be mean, but there are ones where I’ll just say like,


these guys are stuck in like 2005. It’s not a great option for you at this point. I would look at other options. But a lot of the tools have really stepped up their game, which is fantastic and great for readers. Because the products are gonna be better. They’re gonna be great for the folks who are making the newsletters, because they have more features and automations and different tools. It’s a really good time to be in this email space, because you have so many good choices. Last two questions.


What’s your favorite must-read newsletter? Oh man, I would love to tell you that mine is… No one else needs a newsletter besides mine. One that I’ve been reading a lot lately, that I really like… I like their newsletters and podcasts, just because they cover the media space really well, is a newsletter based in the US called Puck, paying subscribers to their stuff, and I just really like how they cover the space. They do a great job giving scoops and insider information, and I happily pay for that one and read it.


every time it shows up in my inbox. That’s the one lately that has been out there that I consistently, consistently read. I will also say when I’m a big college basketball fan here in the US, when March Madness was happening, there’s a newsletter called Field of 68 that covers all things college basketball daily. And that was a must read for me as I was getting into.


March Madness because I really wanted to win my bracket and not that they deserve too much credit for it, but I did actually win my big bracket this year. I was number one. So I was happy about that. I felt like all that newsletter reading really paid off. Yeah. And the last thing is growth tips aside, what’s your favorite piece of advice for a new set of publishers? I think for a publisher, if there’s one thing that they can learn from my experience. So when I started Not A Newsletter,


It still is. It was a Google Doc that I made publicly accessible and started sharing. And it still to this day doesn’t really work very well on your phone. And it’s impossible to find in search. And it’s kind of a weird experience to share a Google Doc. But the content was really good. And I can put a lot of effort and time every month into compiling it. And that was the feedback I got from readers that this was


pretty unusual and pretty well done and that they were willing to make time for it because the content was good. This goes back to the Buzzfeed days. We used to say that we could send our email via Comic Sans, but if it was a good enough email, people would go, I don’t know why they sent it in Comic Sans. It’s a weird font choice, but the newsletter is really good. And so I make time for it. The content is the most important thing. So whatever allows you to start quickly and get the idea out there and start to build the audience.


is the thing you should do. Because the sooner you start to build that audience, the sooner you start to engage with that audience, the sooner you start to learn what people want, what you’re doing well, what you can do better, and then you can make it better from there. Almost nobody mails the newsletter product and has, the first thing they put out into the world is the perfect thing. It’s about testing and iteration and using surveys and feedback to make the thing better. So the sooner it’s out into the world, the better. And improving on your own craft.


as well. Oh, 100%. 100%. The sooner it’s out there, the sooner you can start to make it better. And that’s where all the good stuff comes from. So don’t wait. It doesn’t have to be perfect. It doesn’t have to look exactly right. You can always make it better over time. But first, it has to be out in the world because otherwise you’re just talking about this hypothetical thing. Oh, I will launch it once it’s perfect. Once I designed it this way, once I just get it out into the world.


make it better. And over time, as you start to learn from the audience, you start to develop it into the newsletter product that you want it to be. I am four plus years into writing this monthly newsletter of mine, and it still has a long way to go. It still has things, and I’d like to think that I know a lot about newsletters and think about newsletters and help team with newsletters, you know, and I’m paid to professionally help people on newsletters. And I look at mine and just go like, it’s getting there. It’s got a lot of room for improvement.


And so everyone has opportunities for that too. Start small, start quickly, start as soon as you can, then make it better over time. Awesome. On that note, thanks so much for coming on the show, Dan. It’s been great to have you. Thanks for having me. It’s been a lot of fun. If people are interested to learn more about you and Inbox Collective, how can they find you? is the website for all things.


There’s a link there to my sign up for my newsletter. is also out there in the world. You can find me. I only am really on one social media platform at this point and that’s LinkedIn. Follow me at Dan Oshinsky there. Yeah, sign up for the newsletter because if you sign up, I ask every single reader who signs up, you know, what they’re struggling with, what they need help with. And people always think that I’m crazy for doing this, but I respond to literally every email that I get. And so.


I love the email replies and conversations that come out of it. It’s probably the most valuable thing that I do with my business. I learned so much from those. So sign up, hit reply. I’d love to chat. Awesome. Thanks, Dan. Thanks for having me. It’s been fun.

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