Dan Oshinsky, founder of Inbox Collective, is one of the foremost experts on building, growing and monetizing newsletters. Oshinsky discusses how email newsletters remain a powerful tool for local newsrooms to build an audience and generate revenue, best practices for creating successful newsletters, and the benefits of AI-powered tools for writers. Oshinsky provides examples of successful newsletters and offers advice on how local newsrooms can grow their audience and provide value to paying subscribers.

Episode chapters:
(02:11) – Why should people care about newsletters in 2023?
(07:48) – Accidentally becoming an email power user and newsletter expert
(12:40) – Translating lessons from large national brands to smaller local publications
(14:55) – Local newsroom success stories
(19:56) – Building relationships via different types of newsletters
(24:38) – What is the jobs-to-be-done for your newsletter?
(28:17) – Optimizing your newsletters
(33:13) – Pricing newsletter ads
(37:54) – Paid and subscriber-only newsletters
(43:37) – AI in the newsletter space
(48:12) – Rapid-fire questions

Listen to the episode here:







Dan OshinskyDan Oshinsky runs Inbox Collective, a consultancy that helps news organizations, non-profits, and indie newsletters get the most out of email. He specializes in helping organizations build loyal audiences via email and then converting that audience into subscribers, members, or donors. He’s the creator of Not a Newsletter, a monthly briefing with news, tips, and ideas about how to send better email. He previously worked as the Director of Newsletters at both The New Yorker and BuzzFeed. He’s been a featured speaker at events like Litmus Live in Boston, Email Summit DK in Odense, and the Email Marketing Summit in Brisbane. He’s also been widely quoted on email strategies, including in publications like The Washington Post, Fortune, and Digiday


Full transcript:

(recorded via Riverside.fm; transcript automated via Castmagic.io, unedited)

Oshinsky [00:00:00]: 

If young people don't read email, then why are these organizations succeeding so wildly in building an audience of young people who read email? Just have to spend time listening to them, figuring out what they're interested in, figuring out what they need from you, and trying to build products that serve them. Young people read email. They just want to make sure the stuff you're sending them is really good and going to be worth their time. At this point, nobody has time for lousy email. Nobody has time for for a mediocre newsletter. If I'm going to make time for it in my inbox, it better be great. And so young people read email. They just have to know that it's good first. 

Regan-Porter [00:00:39]: 

Welcome to the Local News Matters podcast, where we explore pathways to stronger journalism, better businesses, and healthier communities. I'm Tim Regan-Porter, CEO of the Colorado Press Association. In each episode, I sit down with guests from newsrooms and others in the local news ecosystem to highlight the innovative work of local newsrooms and those that support them, as well as the crucial questions they face.   

This episode, I’m excited to bring you Dan Oshinsky, founder of Inbox Collective and creator of Not a Newsletter, a monthly briefing (in the form of a Google Doc) on sending better emails. Dan is the foremost expert on building, growing and monetizing newsletters. He was Director of Newsletters at both The New Yorker and BuzzFeed. He works with non-profits, brands and news organizations of all sizes. 

A couple of years ago, the Colorado Press Association brought in Dan to work with a small cohort of newsrooms in a newsletter accelerator because newsletter are such and important part of newsroom evolution. Simply put, if you’re serious about remaining relevant, you need a good newsletter strategy. It forges meaningful connections with readers, is arguably the best way to build regular reading habits, and should be one of your biggest drivers of revenue through memberships, subscriptions and advertising. 

If you like this episode and what we're doing more generally, never miss an episode by signing up for our newsletter at lnmpod.com. 

And now I bring you Dan Oshinsky. Welcome, Dan. 

Oshinsky [00:02:10]: 

Thanks so much for having me. 

Why should people care about newsletters in 2023? 

Regan-Porter [00:02:11]: 

So let's just start off and jump right into it. Why should people care about email newsletters? A few years ago, I was meeting with an executive at one of the major chains and she had just met with an email startup that had built its business on several regional emails and they were building a product. And she just could not believe that in 2018 email was being pitched as this solution because it's such an old technology. Of course, anybody who's been around the industry and dealt with newsletters knows how powerful they can be. But give us that story a little bit. Why should people care about newsletters in 2023? 

Oshinsky [00:02:51]: 

It is amazing to me, too, that email is still so powerful, but the truth is, it's effective for all sorts of newsletters. Newsletters for large media organizations, for big ecommerce companies, for individual writers. It is one of these tools that works for so many different types of newsletters. And it works for a few different reasons. One is the inbox itself is very much this digital living room. It's a place that everyone uses on a daily basis. If you exist on the internet, you have an email address. And thanks to the rise of mobile technology, it's so easy to check your email wherever you go. So you wake up, you check email on your phone, you maybe go to the office, maybe you're going to a home office. Wherever it is, you're checking email during your commute. You're checking email throughout the day, you're checking it at night. It just kind of follows you wherever you go. And the inbox is very curated, unlike a lot of the algorithmic powered solutions out there, a lot of the social media channels out there where you don't really have control over what you see or when you see it. The user has full control over who they let into their inbox, where they see it, and in some cases how often they want to hear from a particular newsletter or writer or brand. So for the user, it's actually a pretty good experience. Now, I'm not going to tell you that everyone who sends email sends great email. We've all had the experience of, I buy a pair of jeans at the store and then suddenly they email you five times a day for the next three weeks until you finally say, that's enough, I'm going to unsubscribe. But you have the ability to say, I don't want emails from you anymore. I have the ability to unsubscribe. I, as the user, control who I let in and who I kick out. And for publishers, what they realized is you get access to this really personal space. On top of that, you get a direct line to readers where, you know, if you get an email address, you can build a relationship with them today, tomorrow, for years in the future. You can build habit through email. Hey, I'm going to send a daily newsletter every day at 7:30 in the morning. Here's what it's going to look like, here's who it's going to come from. You can start to build a habit and routine around reading those newsletters, which is fabulous. And email is really, really effective for converting readers to paying subscribers, members or donors. And so as so many news organizations pivot towards reader revenue centric strategies, ads might be part of the mix, but not the whole thing. Nothing is really more effective at driving conversions than email. So for all those reasons, the conversion rates, the ability to build habit, direct relationship, fact that it's not algorithmically powered, the super personal space, it just makes email a really, really powerful tool for newsrooms. 

Regan-Porter [00:05:44]: 

Agreed. You and I have been around the digital media space for a while and it seems like every few, few years there's an article that, hey, surprise, surprise, emails turned out to be the killer app. And then you get the is email dying? Does it reach saturation point and just keeps, keeps plugging. And I think part of the reason is what you're alluding to there. It just touches so many different aspects of the way we consume information and on the brand side, so many aspects of their business. So you've got the relationship with the readers, but even on the advertising side, as we look towards a dramatically different cookie future, first party data, people know what happens when the platforms own all of your data. And so having that direct relationship, having that email address, and even advertising itself. Burrell's Report this year believe list email as the number one or number two growth area for advertising dollars. So it's ubiquitous, it continues to be. 

Oshinsky [00:06:46]: 

Super powerful, and even skeptics of email typically come around. My all time favorite is in 2009, the Wall Street Journal ran a piece about how email was dead. Jessica Lesson, the writer who was pioneered Jessica Lesson, had a line that was, I'm looking it up right now just so I get this right. Email has had a good run as king of communications, but its reign is over. Jessica Lesson now runs The Information and they have a very successful brand built largely on email and newsletters. So everything kind of comes around. Even the skeptics ultimately often say, I thought it was dead. I thought we were beyond this. And here we are in 2023 with people saying, email is a really powerful tool for us, we're going to keep investing in it. 

Regan-Porter [00:07:35]: 

And the coda to that story with the newspaper executive was talking about was six months later, the company had very much pivoted to a very strong email strategy. 

Oshinsky [00:07:46]: 

It's a pretty common tale. 

Accidentally becoming an email power user and newsletter expert 

Regan-Porter [00:07:48]: 

So tell me a little bit about your background and how you came to be so involved in the space. 

Oshinsky [00:07:55]: 

I am very much an accidental email power user and newsletter person. I got into this space first in 2012. I was the first newsletter editor at Buzfeed, later the director of newsletter there. And I got the job because I'd had some conversations with the Buzfeed team. I thought they were doing interesting stuff and they didn't really have a specific job for me. But they said, we think you're smart. Let's try to figure out a way for you to work with us. Tell us what you're interested in. And I said I'd had some newsletters. I had launched this newsletter and think it was either 2011 or 2012 called Tools for Reporters still around Toolsforporters.com. Some other folks have taken it over and have done amazing things with it. And I said, this newsletter is great. I mean, I send it out to just a couple hundred people, but when I send out a newsletter, I get replies and comments and feedback every time I hit send. People really like not just the product, but they like starting a conversation with me as a result of the newsletter. I said, I think there's something here. At that point in 2012, a lot of the big publishers, like a New York Times, were not really investing in email. They had email newsletters, they had some automated stuff that went out, but they weren't really investing in curated products or reporter driven products or really expanding their stuff beyond RSS and automated Power automated newsletters, there were a couple of places that were doing it at the time. Politico notably, was one like Allen with Playbook was one that was doing great. The Skim had launched and was doing really, really well. Quartz, which launched around the same time as we were doing the stuff at Buzfeed, was doing some good stuff, but it was not going to say early days for newsletters. But in terms of investing in email, hiring someone like me to run email strategy, that was pretty unusual in the media space at the time. I know because I tried to find other people who were operating the space so I could learn from them and not make the same mistakes and heard over and over again from organizations, now we don't have a person who does that job if they were surprised to find out that I was doing the job. So I started in Buzfeed in 2012, built up the newsletter team there. Newsletter strategy grew the audience into the millions of subscribers. 2017, I left and took over as the director of Newsletters at The New Yorker. And there the goal was not just growing the audience and driving traffic, but converting readers to paying subscribers and operated there for two years. 2019, I launched a Google Doc that I published monthly called not a Newsletter@notandewsletter.com, where I was just writing the stuff that I was learning about, mostly because I had become a stop on the New York media tour. Someone would get the job as the head of newsletters at whatever local newsroom or national newsroom, and they would find out that I'd been doing this for a while and they'd reach out and say, we'd love to talk and pick your brain. And I kept having the same conversation. I just thought I should just write down the stuff that I'm learning. Hey, if you're interested, read all this and then come back to me and let's have a conversation. If the writing that I did didn't answer your questions. And over the next couple of months I was doing this while I was still at The New Yorker, and people started reaching out and saying, we're trying to get smarter at this email stuff, we're not really sure who to turn to, we're not sure if we're doing the right strategy. We have some budget though, to work with somebody who's the person we should talk to. And my wife helpfully pointed out after the 12th, 15th, 20th, I don't know how many person reached out. And she said, people keep asking you if they could hire some sort of consultant and they're asking for you. Do you want to be that person? And it was a real light bulb moment. Oh, okay. So I had some conversations with folks around email and consulting and what that might look like. I was really unaware of what kind of this indie consulting world was. I was only familiar with the McKinsey level of consultant. I didn't know individuals for consultants and met some folks and really liked what I heard and decided to jump in with both feet and launched Inbox Collective, my little solo consulting business in 2019. And now I've gotten the chance to work with hundreds of newsrooms and nonprofits and some local newsletters too, and independent newsletters, helping folks figure out how do you build the right strategy, how do you grow your audience? How do you drive revenue through subscriptions, membership, donation, through ads? Through affiliate driving events, deliverability issues, content, strategy testing? I've gotten the chance to work with a lot of teams on a lot of different parts of the newsletter landscape. 

Translating lessons from large national brands to smaller local publications 

Regan-Porter [00:12:40]: 

Talk a little bit about that transition. So we worked together. We had a newsletter accelerator in Colorado where you worked with about ten different newsrooms that were mostly smaller. And of course, you're entering into this consulting phase. You had been at Buzfeed and the New Yorker. How was that transition to working with pretty large national and international brands, to working with this variety of type of publications and particularly the smaller ones? What translated and what didn't? 

Oshinsky [00:13:11]: 

So a lot more translated than you'd think because organizations big and small and even individual writers that I work with have similar needs. The issue is just the scale of the need and the complexity of the need. Every organization that I work with, every newsletter that I work with, wants to grow their audience, get more readers. They want to figure out how they get the most revenue they can get out of whatever strategy they're building. They want to make sure they're landing in the inbox. They don't have deliverability issues. They want to figure out what stuff to test and try and maybe what products to launch next. Now, when I'm doing this with a really large kind of national brand or even large regional brands, the scale of the issue is going to be different. A big regional publisher is going to be able to launch dozens of newsletters. They have maybe several people on a team devoted to audience development or conversion or even newsletters by themselves versus some of the smaller teams that I work with, where just launching and building and growing one really good newsletter is enough. And so it's mostly about the scale of the issue. But I find that the challenges that even I'm working with, one international kind of fortune 500 brand. I usually don't work with a lot of brands outside the news and nonprofit space, but this was one where it was a fun opportunity and I said yes to it. And we're talking about growth and testing, and it's the same things that I talk about when I'm talking with a team in Lewiston, Idaho, or in Los Angeles, or in Texas, or in Tennessee, or in Georgia. It's the same stuff, just at a different level, just at a different scale, different level of complexity. 

Local newsroom success stories 

Regan-Porter [00:14:55]: 

Tell us a little bit about what are some of the big success stories, particularly among smaller independent newsrooms, that have not really had a newsletter strategy. Maybe they didn't even have a newsletter and you've gone in and helped them. What are some of the standouts where you say this really transformed their relationship with the reader and their financials and all of that? 

Oshinsky [00:15:17]: 

One of my favorites is a team based in New Mexico, Searchlight, New Mexico, and I've been working with them since 2019. And at a point where the team was three people when I first started working with them, and now they've grown, and I think they're close to a dozen staff, full time staff now. And email has just been this amazing engine for them. They've used it to build an audience, to drive traffic. And when it comes to fundraising for them, whether it's a pop up kind of flash fundraiser in the spring or a big end of the year fundraiser tied to NewsMatch at the end of the year, email has been this amazing driver of revenue for them. And so I look at an organization like them and just see an organization that started small and built and built and built and over time, with a lot of work and patience and some smart strategies, has been able to build email into a core channel for driving the engagement and habit and revenue that they hope for. And I see this at newsrooms across the country, teams, sometimes small, that'll say when we started we were one or two people and we used email to figure out how we could bring in the audience and the revenue to grow from one or two to three or four and then scale from there. And I see it at larger Newsrooms, a place like WBUR in Boston that I've worked with for also four plus years. Now. When I started working with them, it was just Megan McGinnis, who's their lovely and fantastic newsletter editor, and now they have a team of three people full time on newsletters, plus a whole group of other folks from audience development and events and monetization who are pitching in to help build the strategy. And it's grown from just really this one core. They had a couple of different products, but they had this one core newsletter, WBR, today that they were trying to grow, and now they have several different newsletters. They've done some short run products, these automated newsletters called Courses. They've done these around elections and they're about to launch the second version of one around environmental issues and climate up in New England. They've launched some pop up newsletters like they're doing another one this year called Beach Books, where just for a couple of weeks during the summer, they're highlighting stuff to read while you're at the beach. And so I'd look at them and just say, there's another organization of a team using email to drive all sorts of results. It's great for the editorial team. It builds habit. They're using email to get people out to events at city space, a space that they own where they do live events on the WBO property. They're using it to convert readers to members and donors. All sorts of good uses there. 

Regan-Porter [00:18:02]: 

Yeah, the habit building piece is pretty important, particularly for news organizations that are transitioning from print to digital. Because one of the things I know, one of the conversations in some of the chains that are looking at cutting back on print days, the thing they fear the most is cutting out that daily habit of people consuming their news. And a newsletter is one of the best ways to engage people and form and keep that habit. 

Oshinsky [00:18:31]: 

Absolutely. I think for a local newsroom that produces news on a daily basis, a daily newsletter is a must. Now, some teams don't have the bandwidth to start daily. I've worked for a while with the team at Boulder Reporting Lab, not too far from you, Tim, from where you're based, and they're a great example of a local newsroom. What Stacy and the team there have done, they started with a three day a week newsletter have built that audience into something really impressive. It's driving results for them. It's a huge driver of donations and membership. They're starting to build advertising into it. And now the conversation is shifting towards, well, as Stacy grows her team, how do we do more? How do we go from three days a week to four and ultimately towards a five or maybe even seven day a week product down the road, starting small and building. But every team should be thinking about how do we build the relationships with readers? How do we get them to come back day after day, read our content, engage with our content, provide value, get value from us. And email is still one of the most effective ways to get people in the door and reading, building that habit. And then ultimately, if you have some sort of reader revenue strategy saying, look, if this content is good, if you're reading it every day, we'd love you to pay for it and support us so we can do more of this. 

Building relationships via different types of newsletters 

Regan-Porter [00:19:56]: 

Yeah, one of the things I love about newsletters is that relationship piece, that newsletters can be a product in and of themselves and have their own voice and personality and entryway into getting to know the editors and reporters. And I think when many newsrooms start a newsletter, and certainly this was the case years ago, they started with, I think what you referred to as Glorified RSS feeds just delivered via email because all they were trying to do was push traffic to a website. But now you've got things like Punch Bowl News, where almost all the content is in the newsletter. The Colorado Sun has newsletters where I don't have to click out to read a story. I get the information I need from the newsletter and that makes me value that relationship so much more. I certainly don't feel like there's clickbait there, I'm getting what I need to know and I'm getting to know the reporter. Can you talk a little bit about the different ways people look at newsletters? And do you encourage them to lean into the personality and voice and providing information as opposed to just linking off? 

Oshinsky [00:21:04]: 

Yes, when it makes sense for the organization. Not every team has, for instance, a specific writer or staffer where they feel comfortable making the face of the newsletter. And so you mentioned punch bowl news. There's a great example. Anna and Jake, who started that were already writing the Politico Playbook newsletter, had this voice, had this name, launched this. Yeah, made a lot of sense to put them as the face of the newsletter, to build newsletters around them. Axios has done a very similar thing. So as Politico, a number of organizations have gone that route. Not everyone has that, though. And I think it's absolutely okay to build a newsletter that has a generic voice or maybe isn't even that voicey. The bigger thing for me is around one identifying a really clear audience. Who are the people we're trying to reach, where are they going to be reading this? When can we actually produce this sort of newsletter? Not every newsletter needs to go out at six in the morning. When I was at The New Yorker, that was an initial point of contention. The team, a lot of the editors liked the really early morning newsletters, and we looked at two things. One, when we were producing stories, we tended to publish most of our stories mid to late morning, sometimes early afternoon. We didn't publish a lot of stories at five or six in the morning. We weren't an overnight breaking news operation that we did break news occasionally, but that was not the core strength of The New Yorker, and the other piece was The New Yorker had editorial constraints. We wanted stories to go through, and newsletters too, to go through a certain number of edits and copy edits and fact checks. And we couldn't produce a really good newsletter at six in the morning unless we were going to pay a whole bunch of people to start waking up at three in the morning to do it, or hire a team in London to do this. Sort of thing that didn't make sense. And so we launched a daily newsletter in the afternoon, went out about 1130 in the afternoon, and readers built a habit around it and loved it, and it did great for us. But editorial constraints might be a factor when you publish might be a factor. Staffing in general just might be a factor. If you can build a newsletter around a person or a writer, fabulous, go for it. Readers like building relationships with specific people. It's what makes the inbox stand out. When I open my email and I see an email from a friend or a colleague, I'm going to open that before the email from a random brand or something generic, because I know the person, I have a relationship, of course I'm going to keep an eye out for them. And readers only see a couple of things before they open the newsletter. They see the subject line. They see the preheader text. Sometimes it's known as the preview text. It's that little bit of text either alongside or below the subject line, and they see who the email is from. And so if the sent from name is a person that I trust and like, yeah, I'm going to go out of my way to open that thing. So if you can build something around a personality, fabulous. But it's not a necessity. I think there are a lot of newsrooms that just say, we don't have that person right now. That's okay. I'd rather you figure out who the audience is, what they need from you, what kind of stuff needs to go in the newsletter to serve that audience on a daily basis than say, we have all those elements, but we don't have the writer yet. Let's hold off and wait until we have the perfect person to launch this thing now, let's launch it sooner. We can always make the newsletter better down the road. 

What is the jobs-to-be-done for your newsletter? 

Regan-Porter [00:24:38]: 

And you mentioned, what does the audience want from you? One of the things that Clayton Christensen contributed in addition to disruption theory, was the jobs to be done framework that you should look at, not the demographics of your audience or the qualities of your product. You should start with, why are people consuming this? What is the thing they need and want out of this? And when we did the newsletter accelerator, that was one of the first things you did is walk the teams through, what does your audience want? What are the jobs to be done? Can you talk a little bit about that way of thinking? 

Oshinsky [00:25:14]: 

Yeah. I'll give you a good example of this from a newsletter that I've worked with since the start at WJCT in Jacksonville. It's a product called Jax Today. And they've done a great job with this newsletter, building it up. That team has done a fabulous job creating an editorial product. And at the start they said, there's a couple of things we want the audience to get out of this newsletter. We want them to be aware of what's happening locally. We want them to stay up to date and find out what's happening in the area. But we also want them to get involved. We don't want them to just read this newsletter and go, oh, there's some sort of city council meeting, or there's this proposal, local government all right, I'm aware of it. That's good. They say, we want you to take a next step and actually get involved. We want you to show up for city council meetings. We want you to call your representatives to talk about whatever issues you care about. We want you to volunteer in the community. We want you to take some sort of action. And that was a goal of theirs from the start. And so in the newsletter you'll find a lot of sections that look like other newsletters. There's an intro section with the top story, there's a handful of curated links, but they also have a daily section where they show people what's happening locally, where you can get involved and how to get involved, so you can take that next step. And that's a differentiator for their product. It fills a user need. Readers say I want to know not just what's happening, but how I can do something about it. And their newsletter helps you take that next step. Now, it doesn't tell you call your local official and tell them X. It doesn't advocate like most local newsrooms. It's not advocating on behalf of particular policy, just that here are the places where you can get involved and here are the ways you can get involved if you would like to get involved. And so a lot of local newsrooms that do a great job with your product, they'll think about for every section of the email, what need does it fill? What does it do for the audience? Why are they reading this sort of thing? Often those needs are understood through surveys and research. They'll do a survey of their newsletter audience and say why do you read this newsletter on a daily basis? What's in it for you? What do you look forward to? What's the value you get from us? And then based on that feedback, they'll go, oh, readers told us they read our newsletter because they want the context around what's happening. Great, let's design our newsletter in a way so we explain this happened and here's what it means. Or we're building a newsletter, we want to start a conversation with our audience. So every day let's have a question in the newsletter where we're asking readers how do you feel about whatever issue is on the table today? Hit reply. Let us know tomorrow in the newsletter we'll highlight some of the examples that we and answers we got from the community. If you understand what the needs are, then you can start to build in certain sections and certain. Things within your newsletter that serve the audience in a really clear and specific way. 

Optimizing your newsletters 

Regan-Porter [00:28:17]: 

Right? I think these big picture questions of who's your audience, what do they want, and just the logistics of how you're going to produce this, those are the first things to answer. And that's where we started, in that accelerator. But then there's the technical, not as encoding, but just sort of the minutiae of optimizing newsletters. And I know that's one of the things you work with a lot of organizations on cleaning email newsletter list, making sure you've got everything set up for good deliverability, all of those things that really help you grow your newsletter list, opt in monster and tools like that. Can you talk a little bit about how important that is and what difference it can make to achieving your goals? 

Oshinsky [00:29:01]: 

So there's a lot of newsletter best practices. In fact, it's a lot of the writing that I'm doing on the inbox collective website now is around talking through what I've learned best practices from everything from writing a good subject line to doing a reactivation campaign. A lot of the stuff that I hear from my readers and clients who say, I know I'm supposed to be doing this, but I have no idea where to start. So simple things like testing. Testing is something that I would encourage anybody to do with their newsletter. Maybe you want to start small, testing out the sent from name. Who should this email come from? Is it your name? Is it the news organization's name? Is it a combination thereof? Dan Oshinsky Comma the New York Times. Whatever it is. Or is it just The New York Times? Or is it just Dan Oshinsky? All right, let's try to optimize and test there. Also, congrats to me on being a new member of The New York Times right now. That was a great addition to the resume. You might be testing out subject lines. You might be testing out things like the format of the newsletter or the number of links in the newsletter. Testing is a great thing to do. And you mentioned one other thing, Tim, cleaning your list. So many organizations are afraid to remove inactive subscribers from their list. Usually it's because the sales side is selling based on the total audience versus the number of people who actually open the newsletter. I would encourage anyone who's selling ads the newsletter sell based on how many people actually open and read your newsletter on a daily basis. So for many news organizations, they'll sell what's known as either a cost per opens or a CPM per open. So for every thousand people who open in the newsletter, here's what it costs to advertise. And for something like a native ad in your newsletter, that number might be a good starting place. Plus or minus a little bit might be about $30. So for every thousand readers who open the newsletter, if you have 10,000 readers who open your newsletter every day. Divide that by 1000, that's ten. Multiply it by that cost per opens $30. And the cost of a native ad with a title sponsorship might be $300 in your newsletter. But so many brands are selling based on the overall list size. So we have 10,000 people who open, but we actually have 35,000 people on our list. They're selling based on the 35,000 number, not the 10,000 number. And what ends up happening over time is as. The percentage of people who open your newsletter shrinks because your list is growing, but some people aren't actually opening and engaging that can hurt your deliverability. It might be one of the things that lands you in the spam folder and organizations that grow quickly but see changing rates of engagement. So if your list grows super quickly but your engagement opens and clicks drop pretty quickly, that's a sign that something might be suspicious. The inboxes how all have algorithms that look for suspicious behavior. One of the things they're looking for is, hey, this email newsletter used to go out to 50,000 people. Now it goes out to 250,000 people. The open rate dropped from 35% to 10%. Something's up here that's not normal, and it might flag your email as spam. So cleaning your list is a generally good kind of thing to do. I just published a thing on inboxflective.com about reactivation strategies. There's a few different types of emails that you might want to send. Maybe you want to send a newsletter or an email to reader saying, hey, you might have missed a couple of stories from us recently. Here's some of the great work we published recently. You might want to ask people to change their preferences. You may want to tell them, hey, our emails might be going to spam. Here's how to get our emails out of spam. You might want to give them a chance to opt back in. Hey, we noticed you haven't opened newsletters in a while. Do you still want emails from us? If you do, click this button and we'll keep you on the list. Otherwise we'll remove you you. But reactivation is something that every news organization should be looking at doing at least a couple of times of the year, because it gives you a chance to win back some inactive readers and clean your list. A clean list is a list that is going to have newsletters landing consistently in the inbox and not in the spam folder. 

Pricing newsletter ads 

Regan-Porter [00:33:13]: 

And you mentioned pricing. We get that question every once in a while from particularly smaller newsrooms who have no clue as to how to go about setting that. And I'm sure you get that and recognizing that it's different for niche publications versus general, and it's different for different locations in particular, smaller rural areas versus large cities where there's a lot of competition. How do you talk people through thinking about how to price newsletter advertising so. 

Oshinsky [00:33:41]: 

It depends on a couple of different things. One is the type of ads that you're going to be running in the newsletter. So, for instance, that $30 cost per open rate that I quoted. If you do something like, let's say I launch a newsletter here in New York City. I live in Midtown East. I launch the Midtown East monitor and the Midtown East monitor goes out five days a week. It covers my neighborhood. My neighborhood. It's big. It's a big community. A lot of people live here in this side of town, but it's not the 8 million people who live in New York City. And so maybe I launch and every day at the top of the newsletter, there's the Midtown East Monitor presented by some local sponsor, and then there's a native ad in the middle of it. Well, that $30 cost per open might be a good number for that. It's a big metro area. There's a lot of businesses that might want to advertise and reach this audience in the community. That's great. Now, if I'm selling a secondary ad below, it like a classified text based kind of ad. Local businesses are saying, hey, we're looking to hire someone for a position on our staff. We're looking for waiters. We're looking for secretaries. We're looking for people to run whatever business that we have here. Great. A job listing a classified ad, an event listing. I'm going to price that differently. I'm going to price it usually somewhere like a quarter of whatever I'm charging for a big native ad. And if I'm selling something just like, straight up programmatic kind of ads, hey, there's a banner ad that I'm running in the newsletter, and you can buy into that. I'm selling those at probably a lower rate. I've seen local newsrooms that'll say, we sell these on a daily basis. If they're really big, some smaller newsrooms might sell these based on a monthly kind of cadence. Hey, if you're going to buy advertising in our newsletter, we want you to be the title sponsor for an entire month or two weeks or a quarter. So that way you can charge at a rate that might be a little bit bigger and make more money off it and not have to worry about selling on a daily basis. If you're selling programmatic. I've seen teams that'll say, okay, well, we're going to have ten different sponsors for the entire year, and here's the rate. Let's say it's $2,000 a year. Great. You'll be one of the sponsors. We have these banner ads that rotate through automatically in the newsletter, and you'll be one of the ten, and we're going to sell $20,000 of two k yeah, $20,000 of banner ads in the newsletter, and that'll be our monetization whatever it might be. Just making up a number there, I think, for organizations, you understand kind of based on the size of the area, the competitiveness of the market, whether you can scale up and charge a lot or whether or not you're selling smaller ads and starting at a lower rate, which is also okay. I will say that organizations big and small, though, can do this. I see teams like a rough draft that covers communities in Atlanta. They're doing great with ads. Ads are big business for them, big metro area. But then I also see teams. Like there's a newsletter in Annapolis, Maryland called The Naptown Scoop. Napolis is a small community, and they do a really good job with selling ads. There part of that's because they target a really interesting sort of audience. Annapolis is the kind of place where there's a lot of folks who it's a very competitive real estate market, a lot of folks who retire there. And so there is a certain affluence among their readership, and so they can charge because the people who are competitive in the space, realtors wealth management folks, they want to get in front of these readers. They want to reach them on a daily basis, smaller communities. The rates of your ads might be a little bit lower. It really does vary. But a lot of it starts with, are we selling these big kind of native ads? Classified. It's just programmatic stuff, understanding that helps you kind of price it at a, you know, low, medium, or high kind of point. 

Paid and subscriber-only newsletters 

Regan-Porter [00:37:54]: 

You know, one of the things a few years ago that consumed a lot of the tech and media press was substack, and they had funding and they were lowering away big name writers. And people like Matte Glaciers were dramatically increasing their personal wealth with paid newsletters. And maybe substac's become a bit of a victim of their own success in terms of the narrative and stock price around that. And most newsrooms are not experimenting even with paid newsletters. But what do you see as the future of paid newsletters and should newsroom, are you seeing any newsrooms playing around with that? 

Oshinsky [00:38:32]: 

Sure, there are absolutely newsrooms that are doing a good job with subscriber only products. I'm thinking, for instance, of The Post and Courier down in South Carolina is a good example of this. They have a few different subscriber only products. A lot of them are tied to sports. They have two big universities there, South Carolina and Clemson, huge fan bases for the football teams. And they have some subscriber only products that are targeted towards readers who want to read everything they can around Clemson football or South Carolina football. They're a good example of those. More local newsrooms should be thinking about subscriber only products for a few reasons. One is it's a really good way to retain your talent because we're seeing some writers decide to leave local newsrooms and go independent. Why might they stay? Well, we're going to give you your own newsletter. You're going to write it. We're going to compensate you for it. That could mean some sort of bonus, it could mean some sort of profit sharing too. I would love to see more newsrooms. A great example of this actually is from kind of the independent space, but Puck, which covers DC, New York, La. And Silicon Valley, those power centers. And one of the things they've done, which I love, is their writers who are on staff. When readers convert to a paying subscription because of their newsletter, that reader gets a small bonus and so they're incentivized to create a great product. The better the product we get and the more conversions you get from my newsletter, the more money that I make. Over the course of the year, I'd love to see more local newsrooms, identify ways to say, hey, our star talent, who brings in an audience, who converts an audience, who helps us keep our paying audience, we should compensate them accordingly for that because they're really, really valuable. I think more local newsrooms should look at these sorts of things, though. Start small. At the start, honestly, you're just trying to build out an initial newsletter product that's free, a daily newsletter, arts and culture newsletter, a food newsletter, a sports newsletter, a politics newsletter, whatever it is. But maybe as you scale up and you build, you start to say, there's this more niche product out there. We get a lot of readers who are interested in a certain topic. Could we use a local newsletter that's subscriber only to cover that topic? Maybe it's covering the State House, maybe it's covering City Hall, maybe it's covering a local sports team where there's a ton of general interest. But are there places where we could serve an audience, provide value and tell readers, hey, this is one of the benefits that you get a subscription. Pay us, get access to all this content, and you get access to these exclusive newsletters too. 

Regan-Porter [00:41:24]: 

Yeah, and I guess in my mind I differentiate a little bit between subscriber only newsletters and actually paying for a newsletter because a Substack pretty much while I guess you can log into Substack's website, I think people think of that you are paying for the newsletter itself, not an overall website. Do you see any parallels to that Substack type model coming out of local newsrooms? 

Oshinsky [00:41:48]: 

So not necessarily direct parallels. What I see are more local newsrooms recognizing that they can deploy really great writing talent and give them their own newsletter product and maybe build audiences around those unique writers. I see newsrooms thinking about how they can convert readers from those newsletters to paying subscribers. I see newsletters that are thinking about subscriber only products. All of those things are really for local newsrooms and national newsrooms too. What happened with a product like Substack was it really opened people's eyes to, one, how effective newsletters are at building an audience, but also, two, how effective newsletters still are at converting readers to paying subscribers. Readers are willing to pay for really good content and willing to pay when it's easy to do so. So many of the newsrooms that I talk to and work with have incredibly complex payment systems that are often tough to navigate and use and you look at something like a substac and just say they made it really simple to subscribe to pay. And that simplicity has paid off for a lot of great writers on that platform. And so I think it's been an eye opening experience for many in the media industry just going, wow, these newsletters are really, really effective. It's so simple to sign up, it's so simple to subscribe. Why aren't our processes, why isn't our tech stack set up in a way? Why aren't we using some of the same strategies that we're seeing these individual writers use? 

AI in the newsletter space Regan-Porter [00:43:37]: 

And the big story for the past handful of months has been the release of ChatGPT and AI in general. Have you started to wrestle with AI's application to the newsletter space? 

Oshinsky [00:43:52]: 

I have definitely been thinking about it. I think for any writer, especially writers who are going at it alone, there is some interesting stuff that comes out of this. One is, I think for so many writers, some of these tools that are designed to help with editing and copy editing are going to be hugely beneficial. It's going to make it a little bit easier to take care of that first round of copy edits, for instance, before it goes off to a human editor for finishing. I see interesting opportunities around using some of the AI power tools on websites. I use one on the inbox collective website. It's called Summary Summari and it's a little AI tool, that little bit of code that I plug into my WordPress site. And when people mouse over links on my website, it sees where it's sending them, it reads the article and puts automatically a little summary in so someone can see when they mouse over a link, this little pop up that appears on desktop that tells you a little bit about the story before you click. And people spend more time reading the website than they would otherwise because they find stuff and go, oh, that seems interesting, I'd read that too. There's going to be some applications that go beyond newsletters as well. Starting to have conversations with folks who are building stuff specifically for newsrooms tools that are designed to help you figure out things like how to optimize your headlines, which tags or categories you should be putting a story in. Little things like that that operationally are frankly kind of a pain for a lot of newsrooms and individual writers to do. And that the AI tool can help with stuff like hey, I need help writing the first version of this caption for an image or the alt text for this image. Well, an AI tool might be able to help you do that and do it a little bit faster which speeds up the publication process. Those are all really good things. I think some of the newsrooms I talk to say, should we just be taking our fundraising pitches and running those through Chat GPT and having that run our full fundraising pitch? And the answer is no, not at this stage. I don't want Chat GPT being in charge of your fundraising strategy. You should be in charge of that. You know what your audience is interested in, what they're willing to pay for, why they're willing to pay. We're not asking the robots to do all of our copywriting for us, but I think there's going to be opportunities to use some of these tools to speed up certain processes or workflows or simplify things or take care. Of the less exciting kind of tasks, like writing the alt text for your images that you know you're supposed to do, but that take up time, and they just take a while to do. 

Regan-Porter [00:46:50]: 

So to draw to a close, tell people about how they can find more information about not a newsletter. And working with you and the Inbox Collective team, do you have a team yet? 

Oshinsky [00:47:04]: 

Inbox Collective is really just me. I occasionally bring on some folks to help me with larger projects, but it's really just me. Actually, I will say there is a small team that helps me out with the website. I have a managing editor, she's part time, Claire Zolke, who's great. She's based in Evanston, Illinois, and a woman named Zoe Lambert, who's a recent grad of the University of Ohio's, a journalism school. She's fabulous looking for a job right now. She's great and she helps me out a little bit with production stuff. So there's a small team with the website, but otherwise the consulting business is just me. People can learn more about the consulting business@inboxcollective.com. That's also where I'm publishing stories every single week, a new story every week, all around different parts of email strategy. Some are feature stories, but a lot are how to's and tutorials can dive in there. There's a big archive. And also once a month I publish not a newsletter@notandewsletter.com. And that's this big Google Doc with links and stuff to read that I highly recommend. That goes out once a month as well. Those are the two best places to find me. 

Rapid-fire questions 

Regan-Porter [00:48:12]: 

Great. And then I also end with some rapid fire questions. And the questions are rapid fire, but your answers don't have to be. So, first question are you compared to a year ago, are you more or less optimistic about the future of local news? 

Oshinsky [00:48:29]: 

That's a great question. I'm actually a little bit more optimistic now. I will say this in two parts. We're not going back to a world where certain local newsrooms have hundreds and hundreds of staffers. I've talked with people, for instance, who used to work at Newsday, the moment when Newsday out on Long Island had 500 people on staff. I don't think we're going back to a world where a local or regional publisher like that has the resources to have that many reporters and editors. But I'm very optimistic about the possibility that with some of the tools that exist, some of the opportunities that are out there, that people can build really strong local newsrooms. Now, they just may be smaller than before, but I'm very optimistic about that possibility. I mentioned them earlier, but a team like Searchlight New Mexico is doing pro publica type of reporting but for the Southwest, and theirs is never going to be a world where they have 100 people on staff, but they're building it into a really great sustainable enterprise. Or Boulder Reporting Lab doing an amazing job of covering local news in Boulder, Colorado, rough draft in Atlanta, doing an amazing job of covering some of these big communities in the Atlanta metro area. And that's absolutely possible. We just have to adjust our expectations. We're not going back to 1997, we're not going back to 2005. But I'm very bullish that local newsrooms can be built, can be sustainable and can cover their communities in really powerful ways going forward. And I think email has been a pretty key delivery channel and conversion tool as part of that. So I'm thrilled about that part. 

Regan-Porter [00:50:17]: 

Is there a favorite piece of advice that you've been given either personally or. 

Oshinsky [00:50:22]: 

Professionally when it comes to newsletters or just in general? Well, there's a couple of different pieces of advice. I'll give you two. I'll give you a piece of advice that's newsletter specific and a piece of advice that's not. The newsletter specific thing is when it comes to doing something like a survey, ask something, to learn something. If you are trying to do a test, if you're trying to do a survey, if you're trying to do a poll, if you're going to ask something of the audience, what are you trying to learn from them? I find so often teams will do these tests. They won't have a specific question behind it. They'll run a survey and they'll ask questions and they'll go at the end, all right, well, what's next? What do we learn from this? And they'll go, I'm not sure we should have gone back and figured out a different question because we always want to be asking something where we know, all right, I've learned something here. I know what to do next based on that question. As far as the general advice, just say find the things you love to do and find the people you love to do them with and make time for both. I find that the older I get and I'm not that old, but I'm 36 and starting to get to a certain age where I now talk with recent college grads and realize what year they were born and start to feel very, very old and maybe Jurassic in some cases. Although I know I'm not that old. But the older I get, the more I realize if you find stuff you really love doing and people you love doing it with and you make time for those things and if you do that, you end up having a lot of good days and weeks and months and years. 

Regan-Porter [00:51:53]: 

Is there a piece of common advice or conventional wisdom that drives you crazy and it's wrongness or oversimplification? 

Oshinsky [00:52:00]: 

I will tell you the newsletter thing that continues to drive me more than a little bit baddie, which is that young people don't read email. I get this so often. Young people don't read email. It's thrown out as though it's a fact that's carved into the base of the Statue of Liberty. It's been there for thousands of years. It'll be there in the future. Young people don't read email. And then I always point to these organizations out there like the Skim or Morning Brew or the Hustle, and I just go, if that's the case, and I saw this at Buzfeed too, that's the case. If young people don't read email, then why are these organizations succeeding so wildly in building an audience of young people who read email newsrooms? So many of them just take it for granted, oh, we'll never reach a young audience. Well, you can just have to spend time listening to them, figuring out what they're interested in, figuring out what they need from you, and trying to build products that serve them. Young people read email. They just want to make sure the stuff you're sending them is really good and going to be worth their time. At this point, nobody has time for lousy email. Nobody has time for a mediocre newsletter. If I'm going to make time for it in my inbox, it better be great. And so young people read email. They just have to know that it's good first. They have to have to know that it's going to be valuable to them in some way. 

Regan-Porter [00:53:16]: 

What's one thing you do to restore yourself and maintain your sanity? 

Oshinsky [00:53:20]: 

I am really, really lucky in that I'm married to my wife is so fabulous. I love my wife Sally. We've been married now seven years, seven years this summer. And she's always really good at reminding me when I need to step away from the computer or shut things down and do something for myself. I will give you the most boring answer lately, which is now that it's summertime, I play a fair bit of golf. I have a very flexible schedule with the consulting work that I do, so I can block out 4 hours on a Monday morning and go at a weird time to go play golf. I play at a lot of public courses here in New York, especially in Queens and the Bronx. And they are not the most glamorous golf courses. They are not Augusta national. But I will tell you, I put my phone in my bag and walk around for a couple of hours. I'm not very good at golf, but that always I always come back and go, I feel better. Went for a long walk outside. Not bad. That's definitely on the list. My wife is very good at reminding me too when I need to step away from the computer, hey, let's go to dinner. Let's watch a show, let's read a book. Let's do something that allows you to get away from this for a second because you need it. 

Regan-Porter [00:54:29]: 

What's your smartest time saving hack? 

Oshinsky [00:54:33]: 

I take a lot of notes for my job, so I work with a couple dozen different local newsrooms. Right now. One of the big ways I work with teams is through this thing that I call coaching, and we'll set up a call with a client to say, once a month we're going to set up a call. We'll check in a couple of days in advance. We'll figure out what we want to talk about in the call. It's growth. It's your end of the year fundraiser. It's your ad strategy. It's the next testing thing you want to do, what's the next newsletter you'll want to launch? We'll figure it out month by month, and over time we'll end up doing a lot of stuff. It's not going to all happen at once, but we'll get a lot done over the course of the next year. I work with a lot of local newsrooms in this way, and what it means is that there's a lot of people to keep track of. And so I take notes in a notebook. I put everything into a Google Doc for every client so I can revisit my notes. But the biggest time saving hack is that every and it's kind of funny because it takes time to save time, but I spend a little time every Sunday going through my notes for the upcoming week for clients, so I can check in and say, here's what we talked about last time. What do you want to talk about next time? When I first did this, I wasn't doing it, and it just took me so long to prep for these meetings. And I'll have weeks. Tomorrow is one. Tomorrow is a day where I have eight calls from basically nine in the morning until six at night. And there's a little break in there in the middle for lunch, but otherwise it's just calls all day. And I'll tell you when I do eight calls in a day, by the end of the day I can barely remember my own name. And so it's really important that I have these notes where I can pop in and go, all right, I did this prep in advance. I look through my notes. I remember what we're talking about in this upcoming call, fabulous. And I can jump in and get working with the client because they're paying me for this time, and I can't go. Let's take the first 20 minutes to remind me what we talked about last time. They always remember what we talked about, and I need to as well. The one other small thing that I'll mention, just in terms of productivity, I'm a huge believer in this. Everyone should set meetings that end a little bit early. I never do hour long meetings anymore. When I work with clients, I tell them the calls are 45 minutes. We end 15 minutes before the top of the hour. Some clients are vigilant about ending exactly on time. Many clients go a little bit over, but if we go a little bit over, if we go ten minutes over, that's okay. We still ended five minutes early, and I still have a minute to stand up, to get some water, to walk around and stretch my legs before I jump into the next call. Everyone should do meetings that end a few minutes early. I don't understand how people do meetings that go to the top of the hour and then dive into the very next thing. 

Regan-Porter [00:57:22]: 

Do you have a favorite failure of yours? Or you might even come up with a newsletter example where the failure led to something great. 

Oshinsky [00:57:31]: 

When I was really early on in my days at Buzfeed and I was writing the newsletter, and the newsletter audience was still pretty small at that point, in the tens of thousands compared to the millions that it would become later on when I was there. There was a Friday where Buzfeed at that time was publishing a lot of lists. There was one featured, a lot of kind of YouTube footage of people screwing up on the job, so some guy who works at a Home Depot who accidentally knocked over an entire shelf of stuff, that sort of thing. And I was trying to come up with the right subject line. We were testing out a lot of shorter subject lines, and I thought, I have a good one for this. Based on the story. A good subject line would be, you're fired. That'll be a fun one. So we put it in the newsletter and sent it out. The newsletter went out, I think, about 730 in the morning, and readers didn't seem to mind it. But a whole bunch of my colleagues were on the newsletter and got an email from Buzfeed at 730 in the morning as they were coming into the office that day that said, you're fired. And it didn't seem implausible at that stage of BuzzFeed in 2012, 2013, before Buzfeed had an HR department that you could have maybe gotten fired by Buzfeed through an email that had an exclamation point in it that didn't seem entirely implausible for the company that we were. And so a lot of my colleagues came to my desk and let me know how displeased they were with that subject line. And from then on, I really thought about if I'm going to send a subject line. It's not just about getting people to open it, but how are they going to react to it? What are they going to think when they see this in their inbox? Because there's other things in their inbox. Is it going to catch their eye in a good way? Are they going to react in a positive way? Are they going to understand what they're getting into? Am I setting the right expectations? And I'm not glad that I upset a whole bunch of my colleagues, but I learned a lot from that experience about how powerful a subject line can be and how careful you have to be when crafting one. That's a good story. 

Regan-Porter [00:59:45]: 

And then last question to steal from Ezra Klein, but broaden it. What are three to five pieces of media that you would recommend? 

Oshinsky [00:59:55]: 

I've been listening a lot to a podcast called The Town. It's from Puck Media, and it's around mostly Hollywood, actually. But there's so much conversation going on in Hollywood around some of these subscription businesses, big businesses like Netflix and Hulu. And with the business that I'm in, which is often advising newsrooms around subscription strategies, it's just really interesting to see how other folks in a subscription business that's media but slightly different are handling things and making decisions. I love that podcast and listening to it a lot. I still love the Neil postman book. Amusing Ourselves to death. I just think that's one of those books. It's at this point almost 40 years old, but I find myself learning all sorts of new things when I reread that and think about that one as well. And I want to give you a third good example from the newsletter space. There's a guy actually, I'll give a shout out to, Reid DeRamus, who's got a newsletter called Growth Croissant from the Substack Universe. He works at Substack and he writes a lot around customer lifetime value and running a lot of the behind the scenes numbers to understand your subscription business. Really been enjoying his newsletter a lot, too. 

Regan-Porter [01:01:15]: 

Well, thank you for your time, Dan. 

Oshinsky [01:01:17]: 

Thanks for having me. This was fun. 

Regan-Porter [01:01:20]: 

Thank you for listening to the Local News Matters podcast, and thanks to Dan for your time and all you do for newsrooms around the country and beyond. 

A final thanks to our production partners at Pirate Audio. Pirate Audio believes every community deserves great things to listen to, and they are on a mission to help local newsrooms reach their communities via audio. If you're interested in starting a podcast or need production support for an existing one, let me know and I'll be happy to connect you.   

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