Dan Oshinsky was the Director of Newsletters at both Buzzfeed and The New Yorker. Today he runs his own email consultancy called Inbox Collective. Dan has seen newsletters from the early days, and has been instrumental in developing the newsletter strategy for some of the largest publications around.
In this fantastic interview, Dan shares takeaways for large newsletters and indie creators alike. He shares how his newsletter led to the Buzzfeed job, and how, once there, he discovered the building blocks that make newsletters resonate with their audience (spoiler: cats ARE involved).
Dan also warns us of the danger of obsessing over open rates (or any “silver bullet” metric), and how Job #1 for your newsletter is to earn its place in people’s inboxes.
After talking about the importance of carefully defining your newsletter’s audience, Dan answers these burning questions:
- Can I really build a business around an email newsletter?
- Is email going away?
Tune in for the answers, and so much more!
Links & Resources
Dan Oshinsky’s Links
- Dan’s Website: danoshinsky.com
- LinkedIn: Dan Oshinsky
- Twitter: @danoshinsky
- Inbox Collective – Together, let’s make better newsletters.
- Sign up for Not a Newsletter
It sounds kind of corny, but you kind of have to have a mission. When you start with the newsletter you have to have, this is the thing that I’m doing for this audience.
This is why I think I can be useful and how I can be helpful. And if I do a good job, I build that loyalty. I build the audience in the long run. there’s going to be a return on that investment.
In this episode, I talked to Dan Oshinsky, who was the director of newsletters at Buzzfeed, and then the same job at The New Yorker. And now he runs his own email consultancy called Inbox Collective, and Dan has seen newsletters from the early days. He’s seen multiple waves of newsletters become popular.
And then of course he’s run, some of the largest publications around. So it’s a fantastic interview. He has a lot of takeaways that are good for, you know, large newsletters and indie creators alike. So I’m excited to dive in.
All right, Dan, thanks for joining me today.
Thanks for having me.
So let’s, let’s dive right in. You’ve got an interesting background in that we have all of these newsletter creators who. Come into it from, you know, any number of things, but, but they’re often indie creators where they’re brand new to the space, you know, or they’re growing up through one path and you’ve taken a different path of building newsletters at Buzzfeed than The New Yorker.
And now you’ve got a bit more of the indie path as you’re doing the consulting and everything else, but I’d love to just take us back to when you first started to get into running newsletters at Buzzfeed and what, what started that path?
So it actually started a little before Buzzfeed. The first newsletter that I really launched was a newsletter called Tools for Reporters. It launched in 2012 and it was.
I’ve been doing it a little while. It was Tools for Reporters is exactly what you think it was. It was a newsletter where we share tools that reporters could use.
It’s actually still going. I went to the university of Missouri journalism school and some Mizzou J school grads have picked up that mantle and run with it. And it’s all it just hit earlier this year. Something like 200 additions of this thing has been going for a long, long time. despite my efforts over the years to, to accidentally kill it with, you know, having a job and having other things to do, it turns out when you get hired at Buzzfeed and you have a thousand things to do the like side newsletter, you’re working on becomes a little less of a priority, but it’s my entire newsletter story really starts with this thing Tools for Reporters.
I was playing with lots of different types of tools. And it had stuff that I wanted to share figured a newsletter would be a good place to share it. set up a fairly basic, you know, at the time this was MailChimp. I went to MailChimp, set up a newsletter, pretty straightforward to get something off the ground.
And in a couple of, you know, first couple of weeks, I got to a place where there were a few hundred subscribers. And for me, the game changer with email was I had, I don’t know how many Twitter followers or Facebook, you know, Followers or friends I had at the time, but I had more of those than I did newsletter subscribers.
But if I put something out into the world on Facebook, or I sent out a tweet, nothing would happen, literally nothing would happen. I’d say here’s this exciting new thing I’m working on and nothing would happen. And then I would email a few hundred people and say Hey, here’s this thing I’ve been working on.
And I would get Requests from people that, you know we want you to come in and sit down with us and have coffee, job interviews, the Buzzfeed job partially came at a result of at, or out of me working on Tools for Reporters. They. You know, when I started talking with them, I shared with them my newsletter and they’re like, this is really good.
We like this. We can do more stuff like this. It was amazing to me how much more impact email had. the conversations I had out of email was really the exciting part because it wasn’t just me broadcasting, whatever news right out into the world but Putting stuff out there and then people writing back and saying I actually have some more stuff I want to talk to you about this, or I want to go deeper on that subject.
Or how do you feel about this? I really got to build relationships with my readers and that always struck me as something that was really, really powerful, that set email apart. when I got to Buzzfeed, our, our thinking was twofold. One is we were going to have a chance to build an audience and really have ownership of that audience.
of the relationship with them it wasn’t something where. Social media giant could just say one day, you know, We know you have X number of people who follow you on this channel, but, we’ve made some changes to the algorithm and you no longer have access to that audience. You know, we really have the ability to build relationships through email, which was exciting, but the other thing was the potential for conversations, the potential to ask people questions, to get their feedback and to really get to know our readers.
That was really, really exciting and something we knew there was huge potential for
Yeah, that’s big. And then, I mean, that’s the exact same experience that I had earlier with. Now of like, I actually expected social channels to outperform email, but people were like, you should have an email list. And I was like, okay, sure. You know, if you say so, I’ll listen to smart people and then you actually do it.
And you’re like, Whoa, this is different, you know, 800 people on an email list is, you know, I would take that over like 5,000 people on a Twitter following. You’re definitely on Facebook. And so that blew me away from the beginning. So
There’s also the other thing too, for you, and I’m sure it was, he was definitely for me. And I imagine for you too, like, because it wasn’t something that you were hearing from a lot of other sources you weren’t, you know, like in the news world, when I got started at Buzzfeed, I started going around trying to find, I was like, Oh, I’ll, I’ll talk to the people who have my job at.
The New York times, the Washington post, all these other places. Like I’ll talk to them like these are smart people. I’m sure they’ve already figured out email. Like I’ll learn from them, I’ll steal all of their good ideas and then I’ll bring it back to Buzzfeed. And then I found out those people didn’t exist.
Like those jobs didn’t exist in other places. And. Email. My theory is always out. I’m curious what you think. Like my theory has always been just because everyone uses email all the time. People think they know a lot about it. They just assume like, Oh, I, I send emails all the time. Like we don’t need to have teams thinking about email.
Like, what does email for in a newsroom 10 years ago is what does email for? Here’s an, arguous a reverse Chron RSS feed of our stories. We’ll just send it out to people or many times a day and they’ll click on whatever. And. That’s the end of the story. And so I started getting into it at Buzzfeed was like, all right, let’s talk to the smart people who are already doing this.
And it’s like, Oh, well, there aren’t really that many orgs that even do this. And nobody really had my job. it’s exciting to see how much it’s changed, but it does, whether it’s going to be a Buzzfeed, the work you’ve done through convert kit, you discover that it just takes a certain amount of momentum of seeing like, Really smart people over and over and over again, telling you like this works, this works really well for people like, huh?
I wonder if that email thing works.
Right. Yeah. So what was your title at, at Buzzfeed?
When I started, I was newsletter editor, which was a title that, we made up because everyone at Buzzfeed who wasn’t me was associate editor pretty much aside from a writer, chief, like everyone was associated. And I was like, well, I’m an associate editor, I’m the newsletter editor. I’m sure that’s my title.
And then at some point the team grew and then I hired a newsletter editor and they’re like, well, you can’t be this anymore because that title is taken. And Busby, wasn’t the kind of place where you become like the vice president of newsletters. So it’s like director of newsletters was the next title up.
Then I, when I got hired at The New Yorker, the title just carried over. It’s like, we don’t really know what the title is. Director seems nice. Like, sure. That’s fine. I don’t, I don’t at no point throughout the process was the title a. Important thing for him to work at places like those. I remember telling my boss that new Yorker is like, you can call me whatever you want.
I don’t care. You’re telling me I get to work at The New Yorker, but these smart people and help make a difference. Call me whatever does not matter to me.
Yeah, that makes sense. So you’re bringing up a point about, you know, that, that title or really that job not existing. And I think that’s, that’s fascinating cause even, you know, people just weren’t using email. I mean, they were, but I think about when I was getting started in all of this in 2011, 2012, kind of around the same time, that you were diving in on it.
People were using email, but like 5,000 subscribers was a, was a big email list. Like I remember following, you know, bloggers I followed would be like, Chris Guillebeau or a, Liam about to, from Zen habits. And I remember thinking back to that and like, I think they were like 8,000 email subscribers, 10,000, like, and those are the people that I thought of as being really big in the indie space.
And now of course, like there’s plenty of people with millions of subscribers and. and so much from there, but, but it’s fascinating how even seven, eight years ago, you know, like you said, these job titles didn’t exist. It wasn’t a, Oh, here are all these best practices. Let me go copy them and learn from them and everything else.
So what were some of the things that you learned in, you know, maybe that first time at Buzzfeed running newsletters of like, okay, this is what works, this is what doesn’t.
Well, I’ll tell you this. My first day when I showed up and our chief technology officer showed me to my desk and sat me down and in a very like, He meant it in a very colloquial way. It’s like, do you know what you’re supposed to be doing? And he mentioned it just like, you know, you’re supposed to be doing, I need to go back to my job.
I have other things to do, but I took it into like, do you know what you’re supposed to be doing? I kind of hope when I showed up, they would have like the magic playbook, you know, Jonah Peretti would have like labeled out, like you do this and you do this and you do this. Then you have a job. everyone loves you.
And it’s like, that’s like, no, I don’t know what I’m supposed to be doing because I was scary. But that first year we learned. So much about email. So the big things that first year were just figuring out what an email was supposed to look or sound like from Buzzfeed. Where are we allowed to have personality, your voice?
Where did curation fit in at the time in 2012? You know, even a publication like the New York times, their daily newsletter was not a personal lot. Like today. Even Leonhard personalized, curated, they’re asking questions. We’re starting a conversation 2012. It was just, here’s a list of the stories that are most recent on our website.
As of 6:00 AM. When this email goes out with no thought as to what the right subject line or which stories need to lead, there was no curation aspect. So all of that for us was like, what does curation look like for a newsletter like ours supposed to be, which was trying to do a combination of. News and humor and culture and lifestyle, like what even goes into a Buzzfeedy kind of email.
So a lot of that first year was figuring out what is the voice sound like? How far can we push different sorts of ideas or products? I mean, I remember my first day I pitched three newsletters. The newsletter is for a daily newsletter, a long form newsletter, because we were doing a lot of kind of magazine style, long form reporting, and then a newsletter that I called this week in cats, and everyone laughed about it.
But this weekend cats ended up being a really successful newsletter because among the lessons we learned at Buzzfeed were well, there were really four building blocks for us that made a great newsletter. 1 Newsletters were either about identity, who you are and what you care about. And. being a cat person it turns out is a pretty significant identity. Our cat people love cats. And then the dog people later on got mad at us because they thought we were biased towards the cat people. So we had this week in cats and then we had dog dang, which was also a great newsletter. identity was a big thing. 2 Service was a really big thing.
The stuff people wanted more of, I want healthy recipes to cook for my family. I want ideas because I’m a parent, I’m trying to figure out. How would I entertain my kids? I’m trying to figure out how to do more of the stuff I want to do Buzzfeed Can you help me do that? 3 There was stuff that was more utility based, and these are newsletters around, your job around your community, around the news.
I need to know what’s happening today. So I can be informed that a lot of local news organizations do this now, you know, I need to know what the weather’s going to be. I need to know what’s happening in my community or. if you’re, you know, someone like me, I still do a lot of my work in the journalism space.
Art. I need to subscribe to newsletters around journalism and news. So I’m informed as to what else is happening out there. those utility newsletters do really well. 4 And then personalization. That was a really big thing for us. How can we add and utilize our unique personalities, the voices you could only get from Buzzfeed and bring them into a newsletter that people were really going to connect with and get excited to hear from.
those four building blocks that really shaped a lot of the products, but that came through through testing through really a lot of different launches. Some that worked. Some that didn’t some that people thought were jokes like this week in cats, or, you know, I think we have the w the Internet’s first Royal baby newsletter when George was born at that kid is now like 37 years old or whatever.
It was a million years ago that happened. but you know, we launched these different products, some of which people are like Buzzfeed, but then it turned out like, Oh, people really want this, like, We’re in the business of giving people stuff they want, that they care about. They’re passionate about. Yeah.
Let’s launch the Royal baby newsletter, nothing wrong with that. No reason why we can’t have a news newsletter that caters to a serious news clientele, a politics newsletter, and yeah. A newsletter where where we’ll tell you when you know, the Royal baby is born. These can all exist under one roof.
Yeah. So let’s take a newsletter like this. We can Katz, what does, you know, this is crazy idea that you throw out there and everyone’s like, Oh, ha ha. We’ve got, you know, it’s sort of like two truths and a lie where you’ve got two pitches that we’re suppose to take seriously. And then this third one that like, we’re supposed to ignore and laugh at.
Like, you know, and you’re like, no, no, no, they’re all.
They’re all serious. We’re going to do all of them one day.
But if we have to only do one, it’s the cat newsletter. So you choose, So in that, right. How do you measure success? What does, or what does success look like? is it just that you’re getting X number of subscribers? Is that like the, the growth rate, the open, what are you looking for? Particularly on the cat newsletter?
I got really lucky my first year at Buzzfeed in that I reported directly to Dao Nguyen who’s Now the publisher of Buzzfeed. One of the smartest people in media Dao knows everything about everything. And Dao was somebody who really impressed upon me there wasn’t just a single bullet metric. It wasn’t just like the open rate is the end-all and be-all If the open rates are good, we have a good newsletter. Or if we have a lot of subscribers, this is a good newsletter. We thought about growth. We thought about engagement opens, click to open rate. We thought a lot about, you know, Metrics like clicks per thousand if if the newsletter is going to grow.
How many, you know, how much traffic does this newsletter drive for every thousand readers? so we could project, if this newsletter goes from 1000 readers to 10,000 to 100,000 how much traffic do we think this might drive? We thought about metrics like time on site. You know, we really utilize Google analytics.
If someone’s clicking through on one of those long form stories to a Buzzfeed article, for instance, well, Those articles are going to take you 10, 15, 20 minutes to read. How long do they actually spend with these? Are they just clicking or do they spend time? there? And we would put together a couple different types of metrics to measure success over time.
That’s changed for me now, I think a lot more about loyalty and habit. So how often do people, especially for something like a daily newsletter, how often do people turn to this newsletter day in and day out to read and turn to us for. Know, for, for their news habits. we look a lot more now it’s stuff like onboarding and automation.
How are we utilizing that to drive engagement that we want, but it’s a variety of different metrics across, you know, engagement, habit, loyalty, growth. certainly for a lot of organizations or individuals too, you’re looking at revenue numbers is this newsletter driving the end result that I want in terms of revenue for my business, all of these together, give you kind of a full picture of success.
What I find is the people who just pick oneif the only thing you care about is open rate. You’re going to do anything to get the open rate up. I mean, if the best example I can tell you is sign up for any super PAC’s emails and see the emails they send you. I got one the other day, it was a call to action to support, a a political cause the subject line was, and the, the, the, the sent-from name and the subject line was a flight confirmation.
It was like, Flight confirmation number 6247 And it was like your flight’s been booked. I was like, what is this? And then I clicked and it turned out it was an ad telling me how I need to donate to some political cause it’s like, yeah. When the only thing you care about is opens and just getting people to like getting your message in front, you will do some weird stuff to get people to open your emails.
You’ve You’ve got to have a bunch of different metrics in play.
Yeah, that makes sense. And, well, I mean, first the thing is with any political donation, your email address then suddenly gets like passed on to like 50 organizations. And you’re like, it’s so frustrating, but
It’s it’s the worst part about all there’s many worst parts about politics in 2020, but one of them is you like a candidate. You give them $10. Cause you think it’s, you know, I really believe in this person. And then you find out that until the end of time, you will be getting emails from other candidates asking you for money because that $10 donation means that you are suddenly Scrooge McDuck with an unlimited amount of money to give to all political candidates who come asking.
Yes, but in that you see so many of these subject lines, especially cause I think, well, you touched on loyalty, right? And that being a metric that, if you had open rate, balanced by loyalty as a counterbalancing metric, then you’re not going to push subject lines in a way that, are click baity or spammy or anything like that because you know, that’s going to hurt her loyalty.
But in this case where the email address was just purchased or passed on, you know, like your political party was just like, Hey, by the way, they had made a donation. So now his email address is fair game for any of you. then there’s no thought to loyalty because you don’t have any loyalty to the super pack or whoever else.
And so then of course, they’re just pushing that. So that’s,
And at the, at the end of the day, at the end of the night, too, where people re anyone who’s working on an email needs to think about. If there’s one thing I’ve learned over the years with email it’s that email is not just a broadcast tool. It is a relationship tool. if you think about email as a relationship tool, as a conversation and of the inbox as this really personal space, this is their space.
I tell a lot of my clients, I think of it as like a living room, like the client. So our reader is letting you in and saying, I’m going to let in my family and my friends and some of my colleagues and maybe you, and you’ve got to prove your worth to earn your place in this space. Like, all right. So what are you going to do?
You’re going to start a conversation. You’re going to ask questions. You’re going to seek to learn about them. You’re going to try to make sure your newsletters feel personal and are relevant to them. You’re going to do a lot because at the end of the day, when you think about email as a relationship tool, Well relationships, are a long-term kind of play.
Nobody thinks about how do I develop a relationship for today and tomorrow. And that’s the end of it. You think about how do I, you know, I’m making a new friend, I want to make a friend and I want to keep this friend for a long, long time. I want them to be someone in my life for a long time. You make a set of decisions that’s best to based on what’s best for the Both of you and email is the same way. The more you think about the relationship, the more you think about the conversations you want to have. the more you think long term, you know, it’s not just about getting an email address today and how can I sell something as quickly as possible? How can I get this person to know me, understand me how can I learn from them?
How can I listen to them, establish trust, and then in the long run, once I’ve done that, we can do some pretty cool stuff together. When you think about the habit of loyalty in the relationship, it totally changes the way. You think about email and the types of things you would send to them, the things you want to do with them, what you even build in terms of your email product, all that stuff is great stuff that happens when you shift the mindset from broadcast broadcast, push, push, push to no, this is a conversation. Let’s start talking.
What’s an example that comes to mind from your career. you know, or maybe even from a client that you’re working with now where that relationship really paid off, or, you know, you’re talking about, okay, I’m going to do this in a way that builds long-term loyalty. And that moment where you thought like, Whoa, this is a really loyal audience that we’ve built.
So I’ll give you the personal example with me. I, when I started this Google doc and. January of 2019, Not a Newsletter. The goal was just when I got started at Buzzfeed, I had always wanted there to be a place that I could go to learn from other smart people. And in the seven years between me starting and when I started me starting at Buzzfeed, and then we started Not a Newsletter.
That place never really came up and nobody builds the, the go-to source for, you know, for email conversation, especially for people in news or nonprofits or individuals. There’s lots of great. You guys have one of these, but like there’s lots of great places you can go. For email conversation of high level and a lot of stuff around marketing, but I found that, especially in the new space, it was just lacking.
Like, who am I supposed to go to learn from? So I thought that I might try to step in and, and offer some advice, and be a person that I could share perspectives and learnings from over the years. And then I had this Google doc and just launch it as a Google doc, so I could get out into the world as quickly as possible.
And then I had an email alert tied to that. So you could come back for the next one. So people through that, through my onboarding series, through the emails I sent would reach back out. They they’d ask questions. Sure. Feedback. And what started to happen? I mean, this is one I’m still at The New Yorker.
What started happening was. People started to ask me like this, we’re learning so much about email. We’re really excited. We have this budget to work on our email strategy. These next couple of years, we really, really try to figure out who we should be working with, who can like help us figure this stuff out.
Who’s the person we talk to. And then I would write back like an idiot, like, Oh man, I really wish that person existed. It would be so great. If there was that person who could help you all figure out how to do this stuff, you know, like I have a job I’m working at The New Yorker. I got my hands full. I wish I knew who to refer you to.
And then I got so many of these at some point, my wife just told me, it’s like, people keep asking you who the person is, your, the person. Oh yeah. It’s like, I see. Okay. Now I had to figure out, you know, people who work at it, the people who work at The New Yorker. A great thing about a place like The New Yorker is they always say, there’s that old adage.
Like you want to work with people who are smarter than you you’ll you never want to be the smartest person in the room. There was never any doubt at The New Yorker that I was not the smartest. Like I was always the stupidest person in the room. I was constantly constantly thinking like, I cannot believe how much part of these people are the me, why they let me into this?
Why did they let me into the building in the first place? but that means that people from The New Yorker also go on to like big ambitious jobs. They don’t usually go to. You know, David Remnick can be like, I’m leaving because I started a Google doc and people now want me to show them how to send better emails.
Like that’s not a thing that they’ve ever had to deal with before. but from you really, that was it. That was like, Oh, having, and we’d done this. We’d ask questions of our readers, The New Yorker and gotten great feedback at Buzzfeed. We do these crowdsource posts and get great feedback and have really good conversations.
But with Not a Newsletter, the email attached to that, that was the one who was like just by starting a conversation just by being willing to apply to every email that came in. You know, I had a list when I left The New Yorker at the list was about 1500 subscribers. And I knew when I left that I was going to be able to drive enough business from just 1500 subscribers because I was having these conversations because they were telling me.
It made it real. In retrospect, it made it fairly easy to figure out what I needed to do to make my business successful because readers were writing and telling me, this is the thing I need help with. This is where I want to spend my money. And then when I would hear five, 10, 12 different organizations tell me we all have the same problem.
It’s like, well, Good news. I’m setting up a business to solve your problems, and I’m going to make this one of the problems that I can just solve right away. It was great. I made it super easy now, you know, when I work with teams trying to figure out like, who is our audience? How should we market this?
Like, well, have you talked to them? Have you surveyed them? Have you listened to them? Because they probably have a good, pretty good idea already of what it is that you do really well. And sure. Especially these big organizations, big brands. We’re going to go out and we’re going to spend a ton of money on some fancy marketing agency.
That’s going to come up with a perfect slogan to explain what our product is like. Have you thought first about just serving your audience and hearing from them what it is that you do well, because you might be able to come to that perfect tagline, that explanation without having to spend, you know, five, six, seven figures on a marketing budget that doesn’t actually explain what it is you do well in the first place.
Yeah. Oh, that makes so much sense. And I mean, I love that you brought up earning a living from a small list because I think people that do think, okay, I have to have 10,000 subscribers active 50,000, and we have tons of examples from ConvertKit. If someone earning a living from. 500 subscribers or 2000 subscribers are all kinds of things in that range.
Usually they end up doing consulting, you know, we’re selling a higher priced product, you know, because the smaller number of people that you’re selling to then the higher price point, if say we’re solving for a $80,000 a year salary as our, as our base. you brought up a few things I have on my list here.
In my questions, I didn’t even write it into a full questions or a full question. It just is Google docs. Question Mark. and it’s really not even Google docs. It’s a single Google doc. cause as you talked about Not a Newsletter is in fact not a newsletter. It is a Google doc, that you can go in and as you want to read the different issues in it, you just use the outline.
On the side to go through. And one of my favorite things about it is the, so it’s a, it’s a read only a Google doc, right? You’re the only one who has right. Access to it. But as you’re in there reading that you see like other people popping in and leaving to read it because, you know, I don’t know what it is like anonymous wombat shows up to read.
And so you can see like, wow, there’s eight other people. Reading this at this exact moment, then a couple people drop off and five more people jump on. but so I understand that you’ve launched it as a Google doc to move quickly and you wanted to get it out there and, you know, speed is an asset, but why is it still a Google doc today?
So it started as a Google doc, partially because. It was simple to launch. And also I had done other projects. I had this talk that I’d given a few months earlier where I had produced this as a Google slides. And it was actually, it was a list of ways to grow your, your email audience. And I’ve gotten shared around and people would email me say like, Hey, do you know, we’re just getting started or so-and-so newsrooms.
How do I grow my email list? And then I would go, and I find that Google slides and share it with them. And there were always like four anonymous wombats who are lurking. It’s like, that’s weird. This talk that I gave to a hundred people that I never really publicized. Like, why are there always people hanging out in this Google slides, it just stuck with me.
And so I launched it that way and now it may just be permanently stuck as a Google doc because it got known as the thing. That’s a Google doc. There’s a novelty to it. I always tell my news clients. Who will remark on the same thing going there were 17 people reading the Google doc at the same time on a random Tuesday, but.
You realize that if you go to your Google analytics, there are literally thousands of people reading your website right now. Why are you impressed by 17 anonymous wombats? But I think there’s something about knowing that other, the, the, being able to look and know that other people are looking at this same thing at the same time, there’s something to it about knowing there’s a collective action there.
You’re not alone, especially. This year when everyone’s isolated, the idea of, especially right after I sent it, when people like there’s like 175 people reading this thing right now, I’m like, yeah, the email list is a few thousand people at this point. Like people actually read this thing. I don’t can’t fully explain why, but people keep listening to me for some reason.
And so, yeah, it might just be stuck as a Google doc. I will say. And I’m disappointed to say this, but I’m happy to break the small bit of news here on this podcast. I do think next year there will be an actual website that people can go to, to find some of the resources and links because. It’s to me. I started it to be as useful to as many people as possible.
And as much as I would love to have it permanently, be like a series of Google docs and slides and this weird little world you have to like keep clicking and navigating to find. I also want to be more useful to a wider audience and it would be nice if. You know, I, an ironic thing about Google docs is they’re not actually SEO friendly, despite it all being a Google product, Google doesn’t make Google docs, SEO friendly.
You can’t find it. So if you search for Not a Newsletter, You ended up getting redirected to posts or things, other things that people have written about it to get to it. It’s I would like the stuff that I’m doing that I think is getting really useful to a larger audience to reach a larger audience. So I do think there’s a world in which at least some of the, Not a Newsletter kind of universe exists on a real website that you can, you know, search for and find, it might happen.
I think it’s probably stuck as a Google doc for the long-term though, just because. I don’t know if I switched it over. I think I would get angry emails from people saying that I like sold out to a WordPress or something. I’m not quite,
Well, I like to think of Not a Newsletter as being like, sort of the speakeasy of newsletter content, where you have to know where to find it, you know, it’s like, it’s it’s and then you get there and you’re like, what did I even, what is this? but it goes to show that the important thing in a newsletter or any publishing business is the content.
And really what you did is you cut through all of the noise of, should it be a newsletter? Should it be a blog? Oh, no, sorry, this isn’t a blog. This is a magazine. Or like any of these debates of decisions that people get into. And you said like, look, it’s content like valuable content delivered on a consistent cadence and a Google doc works right for that. so I love the simplicity of it.
I always, always, always urge newsletter. Creator is. If you’re thinking about launching a newsletter, the two things you have to think about first are and not just a newsletter, any product, a blog, a website, an event series, anything, any piece of content or storytelling that’s going out into the world who is the audience for it.
And is it as clearly defined as it can be? Do we know really who we’re trying to reach? You don’t have to come up with. My, my reader is Susie in Des Moines. She’s 36 years old and she likes shopping at Hy-Vee, but like, you should know who your audience is in this case. My audience is people who work in email care about email, send email, and make their money off of email.
Alright that’s about as specific as I can get. And then what am I going to do to serve them? What is the job of this newsletter? And with mine it’s I want people to be able to dive really deep into a topic that affects their lives. Help give them the opportunities for analysis, for insight, to identify trends and because it’s packaged in that way.
It resonates with folks, but if you know any newsletter and you, your newsletter going to have 50 subscribers, 500, 500,000, know your audience and know what you’re trying to do to serve them so often. And I’m sure you get these conversations too, on like a daily basis. People reach out. I have this amazing idea for an email.
It’s going to be great. Well, what is it like? Well, It’s a newsletter where I share the most common one that I get. It’s like, it’s a newsletter where I share all the things that I’m reading every single week, people are going to love it. Like, all right, well, okay. Newsletter, reassurance stuff that you’re reading this week.
Who’s the audience like the audience is anyone who’s like smart and curious and interested. I’m like, yeah, I have really bad news. That audience isn’t there. You have no audience, like you’re building it on an audience of everyone, which means you’re not building for anyone. Like who are you really building for?
Who are your people that you’re trying to reach now? Long-term you might reach more people than your existing audience. You might be able to build an awesome product that starts with a pretty narrow audience, and grows into something really big. Cool. That’s great. a Great outcome. But start narrow.
Start with something really specific. It can always grow from there. People start thinking I’m going to build the next Skimm I’m going to build the next morning brew. I’m going to be the next James clear. I’m going to be the next Malcolm Gladwell. everyone is going to read this. no, you have to start small and specific.
Have an audience in mind, know how you’re going to serve them. Then you can figure it out from there and grow it from there.
Yeah, for sure. So. You know, we talked about newsletter starting back in 2011, 2012. Things have changed a lot, even just in the last 18 months or so to the last two years. What’s your take on like this hockey stick of growth that we’ve seen in newsletters?
it was in some ways kind of inevitable because even just in the time I’ve been doing this. This is at least the second cycle of email is cool. There was one back in 2013, 2014, when products like the Skimm and Horts were doing really well. And TinyLetter was really on the rise and doing well, everyone had a TinyLetter and it’s like, email is cool.
And then there was the inevitable backlash, email sucks. Everyone hates email. I hate getting emails, yada yada, and then, you know, all of us working in email just kept doing our thing. And then when. This came back already for whatever reason. And cyclical comes back around. This is at least the second cycle of email as cool.
And it will be followed inevitably with a backlash towards like emails to add. I hate email. it’s just, it’s going to how it’s going to go forever. someone’s going to invent the brand new thing. That’s the, the email killer. Then people forget You kind of have to have an email address to exist on the internet.
And most people like using email, it’s simple. It’s there on your phone. You don’t have to be taught how to use it. And if you build good newsletters, like great, you’re reaching people in a space they use every day. Plus thanks to the rise of mobile phones. It’s easier than ever just to read something on your phone in those couple minutes, while you’re getting coffee or you’re on the subway or whatever it is anyway.
What I think has really happened the last few years. that’s exciting is people have shifted from thinking about email is cool because email drives traffic. Email is the place, especially in the news and non-profit world and brand world was like, email is what drives all this attention, attention, attention.
And now it’s like, Oh, Email’s The thing that actually drives all my results. My revenue comes from email. If I do a good job building the right products and the right relationships. Email’s going to sell a subscription to my publication. It’s going to drive a sale of my product. It’s going to lead to a donation to my organization.
It’s going to be thing that drives a new member. now we’re seeing also people creators, and this is so exciting thinking, like if I build my audience, if I want to sell courses, I want to sell a membership, a subscription product, get people to come out to an event. Awesome. Like my email list is the thing that’s going to do that.
I think email is just. No matter how much people say that email is like, it’s going to die. It’s not going to last, yada, yada like email is here to stay because it works really well. And it does. At a place like The New Yorker, Conde Nast, our parent company used to talk a lot about this idea of cross-functional teams.
We’d be like, all right, we have people from marketing and sales and editorial and all these different parts of the work we’re going to work together. Email is the cross-functional tool. It’s the thing that does a little bit of everything. It builds relationships. It drives loyalty. It drives traffic. It drives sales.
It keeps, keeps people coming back and reduces churn. Emailed us a little bit of everything. So I know people want email to go away. I think it’s just kind of here. You can accept it and get with it and try to build awesome things for email, or you can keep fighting it and keep fighting it. and At some point, people are going to give in and just say like Alright I guess this thing that works really well and everyone’s everyone’s having success with, I guess I’ll give it a try.
Yeah. Oh, that makes sense. so as you’re looking at platforms and the recommendations on where people should. like how they should set up their list. Obviously there’s the converts and sub stacks and ghosts and WordPress and medium and everything else out there. Like what are you recommending to clients?
And what are the factors that, that go into that as you’re trying to figure out what’s the best bit for each person’s newsletter?
So, wow. One is what that is a giant question. It is, it is one very individualized. I’m always very cautious about making big public proclamations. Like I never want to be in a position where. I, you know, I’m on a podcast or I write something in my Google doc and I’m like, this is the thing that everyone should use, because I remember seeing this back in the day where there’d be like studies done around email marketing and some organization would come out with some big report.
And they’d say, like we did all these tasks, did all these tests and we found out that purple buttons convert best. And then you would open any email for the next six months. And they would all have purple buttons because one test happened and everyone just kind of thought on critically. It was like, well, I read on so-and-so marketing blog, that purple buttons.
So like purple buttons for all. and so I’m always very cautious about being like, Oh, this is the thing you should use because. Everyone’s case is unique. And so a lot of what I do is kind of individualize conversations with folks. I’m trying to figure out better ways to do this. I released a up like a basic version of this ESP guide a couple of months ago, and there’s going to be additions to that.
I’m going to do one in 20, 21 to around monetization from newsletters. And I’m trying to figure out ways to introduce kind of. Different sorts of recommendations for different sorts of users and try to personalize it as best I can. But even with that, I’m still expecting, I’ll probably even do a fair amount of like one to ones and encouraging people to reach out, to ask questions.
Cause like, I think email can be so powerful and so useful. And I’m so incredibly nervous about saying like, everyone should do this and then forever. Or everyone’s like, well, I read this one thing. And even though it doesn’t necessarily apply to my case, I’m just going to take it at face value and use it.
And then people like Dan told us to do this and it didn’t work out. what I will say is what’s very exciting. Is just one of these options, but there’s more options now to use email and use email effectively than ever before, which is amazing. From a creator perspectives is proliferation of tools, tools that can exist and be integrated with other sorts of sales platforms.
So, you know, I’m an individual and I’m trying to sell courses or books or consulting. Or a paid subscription to my newsletter. I’m a news organization or nonprofit trying to drive reader, revenue, an e-commerce business, trying to drive sales, the number of tools that exist out there today, and options is really, really exciting and options.
I mean, as far as I’m concerned and I always, as much as the work that I do with various ESPs and tech partners, like at the end of the day, All the writing that I do and work that I do is in service of my readers, who are writers, creators, newsrooms non-profits brands who are just trying to get the most out of email.
And what I always tell them, it’s like the fact of the matter is there are more things to do with the stuff you want to do now. And there were a year ago and there were five years ago. It means you have choice. Choice is a really good thing for you. You get to pick like what. Back it up. And actually to your question, what I usually tell them, it’s like start with the stuff that you absolutely need.
What’s the stuff that you absolutely absolutely absolutely need to be successful, make that list of the three or four or five things that you care most about. Okay. So at the top of your list is automation’s great. It doesn’t mean that the number one thing is automations. Don’t pick a tool that you aren’t crazy about, the automation kind of feature, and then start to narrow it down and ask to have this sort of automation.
And we need this level of personalization, or we need a tool that has certain integrations, you know, we’re working off of WordPress. So we need something that has a native integration with WordPress. we’re working off of ghost and we want to figure out something there. We use Zapier for a lot of things and we need it to work, whatever it is, think about, you know, what features you need integrations you’re going to need certainly cost is obviously a factor, the data that you want out of it.
And. With whatever tools you’re using, think about whether or not the product is being built by people who get your use case. You know, something that I, I really respect about what you guys have done at ConvertKit is you all have always really been this creator first kind of ESP. And there are lots of great email options out there and different ESPs are being built for really specific use cases.
Awesome. Like. Try to find ESPs or partners who get what it is that you’re trying to do. It’s not just a matter of, you know, I listened to a podcast and I heard this one, ESP advertise. So like, I’m going with them to think more critically, like, do they get what you’re trying to do? And, you know, I. Even at a place like Buzzfeed in the back of the day at Buzzfeed, we use campaign monitor, send our newsletters and they were really good partner for us.
back in the day, what I found was a lot of other newsrooms just automatically without asking us just picked them as the partner there. No, we had a really specific reason for picking it up. There were things we liked about their team, their setup, their customer service, their automations. That were really specific to what mean needed.
You guys are picking them because you saw a press release that had my name on it. That I said that I really liked using their tool. Like, that’s fine. I do like their tool, but I really wish you guys had asked. You know, Dan, like, what do you think of this? We’re trying to do X, Y, and Z. Cause like they might be the right tool for you.
They might not. and you really, because of the choice out there, like I just always encourage teams, like think critically, really make the list of stuff that you need, need, need. And then the stuff that would be really nice to have maybe, you know, Maybe it’s really, really important to you that your email tool will have like a countdown timer built into the drag and drop builder.
I don’t know. Maybe that’s not. It’s like at the top of your list, which case sure. Like that narrows down your options quite a bit. Maybe the most important thing is automations. Maybe the most important thing is integrations. Whatever it is, like start with the list of stuff that you really need. And then that should help you narrow down.
Like, you know what automations is top of the list. This tool doesn’t really do that. This tool doesn’t do that. Integration is really important. Well, that narrows it down a little bit more. You’re going to be able to find something that does a lot of what you want to do. The other thing too. And I mean this with all due respect to the convert kit, which I think is a wonderful platform, no email tool does 100% of the things you want to do.
And, until you build your own email platform that does all the things you want. Like no email tool does a hundred percent of the stuff you want. If you get someone that does. 75% of the stuff you want, you get down on your knees and you think the product team that built that tool that does 75% of the things you want, you signed a contract and you move forward.
Nothing does everything. There’s always gonna be stuff you wish it did. And that’s just kind of, part of it.
Yeah, that makes sense. Well, and I think the biggest takeaway is from what you’re saying is that. The tool is ultimately not the thing that matters. What matters is great content in front of the right readers. And if you focus on those things, then, you know, like you said, get the tool that’s largely a good fit, not going to get in your way and otherwise focus on the content of the vendors because ultimately your newsletter could be a Google doc if you want it, you know,
It doesn’t really matter what the product looks like. It’s about the content. And are you serving a really specific audience? You do that. You can deliver this thing via carrier pigeon and it’ll do well, needs to be, have the content, know what you’re trying to do, do for your audience and do it well every single time.
And you’re going to do good things in the long run. Whether it’s a podcast, it’s a blog shoot. You can prove to a print magazine, you can do a newsletter. You can do an events series, whatever it’s audience content well over and over and over again. And you’re going to have good results in the long run.
Cool. I want to touch just for a second on monetization.
I reccomend it.
Yeah, money. it’s it’s helpful. Yes. I’m pro monetization. Just want to get that out there.
You could slap it right on the, on the, the subject line of this, of this podcast, of this episode. Oshinsky, colon recommend making money. I’m not necessarily going to tell you how to do it, but I recommend trying its very least
Yeah, exactly. So in that you’ve probably seen all kinds of different ways that people are making money. You know, paid newsletters of charging directly for the content, is seeing a big rise. People are doing, you know, courses, books, any of those things I’d love kind of your general overall take. And then what specific area that I want, you know, like your take instead of just some random newsletter creators take is kind of at this price point because you’re seeing the wall street journal, and all of these other publications doing right.
They’ve done paid subscriptions for a long time. And often you have an individual newsletter creator charging more than like a major publication is doing, right. So let’s say that, you know, I’m signing up for, for this sub stack for $20 a month and I’m getting content that I’m really enjoying. And then I come across, you know, the New York times wall street journal, and I’m like $15 a month.
That seems really expensive, you know? And you’re like, well, wait, what, you know, it’s, I’d love your take on, you know, these price points that individuals are charging versus newsrooms and. And, kind of thoughts on the whole paid newsletter thing in general.
So one is. I think it’s amazing that this new format existed. I mean, Ben Thompson, Mr. Tucker was really the first one of these to do it. And it’s the pioneer here, self stack and the work that you’ve done to push this forward. He’s amazing. And now we’re seeing a lot of folks interested in, can I build a business around a newsletter?
the answer is yes. I think there’s a couple of things to keep in mind. One is not everyone needs to have a paid newsletter. Like I am one of these folks, Not a Newsletter, I suppose, could be a paid newsletter product that people would pay for access for I’ve enough readers that if I went paid, it would probably do pretty well.
I don’t really have a lot of interest in doing that because I one. I Want to try to get my stuff out to as many people as possible impact for me is way more important than, you know, the total revenue I drive. Also, I make more than enough money with Inbox Collective. I don’t need the, so I’m happy with what it does and how it helps and, and, and.
You know, everything that is fucked up, doesn’t have not just a lot of works. Dan, Runcie at Trapital is another great example, had a paid-newsletter product realized Oh, my impact is actually in, in telling these stories and doing consulting cool. Like there’s lots of different ways to make money off a newsletter that aren’t a paid newsletter.
Consulting selling courses, getting people out to an event series, building a membership program. these are all ways you can drive revenue and that’s really, really exciting. So anyone thinking about launching a newsletter, thinking about making money from it? You don’t have to immediately go to paid newsletter.
Like there are other options. It is one of several. I also think what’s really crucial and we’ll see, I think a ton of in 2021 are different types of paid newsletter products. So the wall street journal is a fantastic organization. Subscriber love their work. I think they do awesome stuff. We’re going to see a lot more in newsrooms in 2021, say, you know what?
There’s actually a group of us who live in this city. We want to cover the city really, really well. We’re going to launch a newsletter. We’re going to launch and have a subscription product. That’s going to cost X number of dollars per year. People are going to pay for access to local news or coverage, in Charlotte, the Charlotte ledger.
The team that I’m starting to do some work with, and they’re doing amazing work it’s business news for Charlotte, a very small team of reporters working on that. There’s going to be a lot of interesting opportunities there. It doesn’t just have to be, I’m a single person. I tried to build an audience and tell you about what I’m thinking there.
There’s other opportunities out there there’s only so many, you know, Andrew Sullivan’s of the world, and. For a lot of folks actually thinking about a local news angle or thinking about working together with a handful of different writers to put together a real publication, this kind of bundle model publication model is really, really interesting.
I am really bullish on the future of kind of driving record. I knew from newsletters, once you build an audience, there’s lots of opportunities to sell stuff. I just hope that people. There is a little bit of fear on my end that people are going to start these and think like I saw that. No jet lag, launched a newsletter and it’s doing amazing.
And he’s just one guy reporting on this so I can do it too. And they think In three months I’m gonna be making $100,000 a year off my newsletter. I’m like, well, you don’t have an audience yet. You haven’t defined an audience yet. They don’t know ya It’s going to be, if you’re building a, you know, newsletter product you want to be your full-time business.
It’s probably going to be a two-year process minimum to build and grow and drive the revenue you want. this is not a game you get into with like, short-term returns in mind. I often find myself saying direction is more important than speed, where you are going is more important than how fast you get there.
If your goal is to figure out how to make a quick buck getting into the newsletter game is probably not for you. You had a question in there somewhere that I
No, I, I, I think you’ve covered it. I, I, that’s a, that’s a great place to kind of start to wrap up. This is a long-term game and going all the way back to relationships and building that with your audience, building that loyalty with your audiences, it’s going to take time. And when you see things, I think a lot of people online see these gold rushes that happen over time.
Right? You see someone making money, whether it’s, you know, maybe courses and then it’s Bitcoin, and then it’s amp like fulfillment by Amazon drop shipping or whatever else. And. So I think you’re going to have a lot of people right now and go, Whoa, newsletters are the way to make money right now, whether you’re doing a paid newsletter or anything else.
And it’s like stop chasing gold rushes. Like maybe some of the other things, there was a gold rush. The gold rush of newsletters is going to take a long time for you to achieve. And I think most of the people who come in with the intention, or if they’re there for the primary reason to make money, rather than for a love of writing or the craft or whatever else.
They’re going to get burned out and give up while before the money shows up.
it’s the, it’s exactly what I mentioned earlier with, my old boss Dow and that silver bullet. Like if the silver bullet metric is. All I care about is revenue. And I just need to make as much money as quickly as possible. Like this is not something that’s going to work out for you. If your only metric is traffic, like, all I care about is driving clicks.
Like this is not going to work out. You have to have a couple things in mind. You really have to have. Honestly, like, it sounds kind of corny, but kind of have to have a mission. When you start with the newsletter you have to have, this is the thing that I’m doing for this audience. This is why I think I can be useful and how I can be helpful.
And if I do a good job, I build that loyalty. I build the audience in the long run. I think there’s going to be a return on that investment and that time that I put in, but it’s not a short-term play like the, I drop shipping and Bitcoin. These are all great examples. Like email is like spend is like, I have a thousand dollars in the bank, where can I put it to make quick money?
You’re like, well, I guess you could like bet it all on Bitcoin. And maybe you’ll get lucky. I don’t know a thing about Bitcoin, but I all other, other, other than that, Every time somebody tries to tell me about Bitcoin. I get confused. And like, I still don’t understand that at all. But if your goal is like, how do I make a quick buck?
Like, I guess, like spend it on Bitcoin, but you could also just, you know, drive to Reno and put a thousand dollars down on black or whatever. And see if you double your money. Email is like, I don’t know, taking a thousand dollars and going out and buying some shares of Coca-Cola like, could it make, could it be successful for you in the long run?
Yeah, that’s probably a pretty good bet. Give it 10, 15, 20 years.
It’s a longterm play. You gotta be in it to win it.
Yeah. Yeah, totally. Well, Dan, thanks so much for joining me. Thanks for coming on the podcast. I’d love to, for you to just to end by sharing where people should follow your work and, and, you know, follow Not a Newsletter and Inbox Collective, and all
Oh, yeah, thanks. So people can find me, Not a Newsletter is available at notanewsletter.com. and if you want to sign up for it, signup.notanewsletter.com. There is an email alert tied to the newsletter. It’s not a newsletter. It’s an alert. I know it’s a technicality. Please don’t be the 9000th person who’s emailed me about it.
I know, I know. I know when I launched it, I gave it the name. I didn’t realize that one day I was going to have to explain over to him. There is an email alert technically, and it’s not a newsletter, the whole setup. So I signed up at notanewsletter.com. I do writing every single week, not on newsletter topics, just about stuff that I’m learning danoshinsky.com.
And Inbox Collective, which is my consulting work, where I work with nonprofits and news organizations and brands to help them figure out how to get the most out of email that’s inboxcollective.com. Naturally, that’ll actually take you to a set of Google slides. again, once you, once you kind of form a brand as the person who does all their stuff on Google docs, this is what happens.
You got to stay true to the brand. Yes, exactly. All right.
Thanks so much.
Thanks so much for having me.