In this interview, Dan Oshinsky, the former Newsletters Director of both The New Yorker and BuzzFeed explains why your newsroom should have a newsletter strategy. 

No matter if they are big or small, newsletters are a bedrock of your reader revenue efforts. Even without a direct reader revenue strategy, Oshinsky says, newsletters are a great way to stay connected to your audience.

There are a lot of tips, insights and resources within the interview. We collected them into a shorter piece: 7 potent insights, ideas and resources for your newsroom newsletter.

About Dan: He runs Inbox Collective, an email consultancy that works with news organizations, non-profits, and brands to grow audiences, build relationships, and convert readers to subscribers, members, donors, or customers via email. He is also the creator of Not a Newsletter (sign-up here), a monthly briefing with news, tips, and ideas about how to send better email.

This interview has been edited and condensed for clarity. Estimated reading time: 18 minutes.

Dan Oshinsky, former Newsletters Director of both The New Yorker and BuzzFeed
Source: courtesy of author

Should every news organization have a newsletter strategy in place in 2020?

Yes, next question (laughs). 

Newsletters allow you to build a relationship with your readers. The amazing thing about email is that you can ask a reader a question and they can write back, just hit reply and share their thoughts directly.

The other thing is that, as an old colleague of mine, Jonathan Perelman at BuzzFeed, used to say, is that content is king, but distribution is queen. And she wears the pants. The stories, the reporting a newsroom does, is so important. But if you don’t have a way to get stories out to readers, you’re in trouble.

Facebook, Google, Twitter or other algorithm-powered channels control the audience. You can have 10 million fans on Facebook, but it’s not necessarily the audience you can reach tomorrow. Facebook could decide it doesn’t want your fans to see your content anymore, or it wants you to pay for them to see it. You can reach them, but you’re going to have to spend money to get content in front of them.

With email I know that if I get an email address today, tomorrow, a year from now, if I do a really good job, if I build a relationship, a reader will stay with me. I still have readers of my very first newsletter I launched in 2012 called Tools for Reporters. It’s still going. Some fellow University of Missouri alumni took it over from me a few years ago, and are still doing an amazing job with it.

There are people who signed up in 2012 who still read it every week. If you do an amazing job, you can keep a reader for a really long time. The other reason email is so powerful is that email does a little bit of everything. 

You can use it to drive traffic to your website, convert new readers to paying subscribers or donors or members, get readers out to an event or to show up on Zoom – if you want them to do anything and you want people to stay engaged. 

The best way to start a conversation, to sell something, to get people to take any sort of action is email. It’s a rare tool and a channel you own. For all these reasons, email is really, really powerful.

Email is one of the oldest digital communication forms there is but we have a better overview of active Facebook or Twitter users than email metrics. Reuters Institute started tracking it in the Digital News Report, but it’s not perfect. Do we have any data? Can we say if people open our newsletters?

First of all, no organization sees 100% of readers open their emails. If you can get 30% of your readers to open your newsletter, that is very good. A 25% click to open – meaning 25% of readers who open a newsletter click on something – that’s really, really good.

The other number I can share, this is in a Google News GNI report that came out last year – the best newsrooms convert about 10% of unique visitors to newsletter subscribers. So if you have a million unique visitors, you should have about one hundred thousand email subscribers. That’s the general rule of thumb for best in class sites, at least here in the US.

The bigger thing you’re describing is that most newsrooms haven’t spent that long investing in email. When I started at BuzzFeed in 2012, I was hired as the newsletter editor. I spent a lot of time trying to find other people who had the same job. The New York Times, The Washington Post, The Wall Street Journal – they didn’t have newsletter editors. Quartz had some people working on newsletters and there were news products like the Skimm. But there weren’t a lot of people who had my job.

In 2012 most newsrooms had an RSS feed of stories they would send once a day to readers. There weren’t a lot of organizations investing in email. Politico had a newsletter called Playbook. That was very unusual. Quartz had a really good newsletter. It was very unusual for news sites to invest in email.

Most organizations have changed. Most big newsrooms have a newsletter editor, someone in charge of the email strategy, for the last three to four years. The New York Times, The Washington Post, The Wall Street Journal, The Economist, The Telegraph, The Guardian… But because it’s new, it means a lot of organizations haven’t shared publicly a lot of the data they have, or don’t want to share.

Some of the stuff you’re looking for, that exists elsewhere – a lot of that infrastructure just doesn’t exist. The other issue is a lot of Facebook data is public. Email data is all private, and because it’s private, a lot of these organizations hold it really close to the vest. They will say “we don’t want to say publicly how many readers we have or how many people open it.” 

From Dan’s free presentation: 25 Ways to Sign Someone Up For Your Newsletter

In the last two to three years there was a resurrection of editorial newsletters and we have actually seen a rise in anchors for newsletters. This is what The New York Times is doing with several newsletters, and other publications are joining in. There is visible investment from big news organizations. But what would be your advice for smaller newsrooms with not enough resources?

Smaller, local newsrooms should start with a daily newsletter. Start with the local news and figure out what your best version of a daily newsletter is. It doesn’t have to be incredibly complicated to start. A really good daily newsletter could mean we have an introduction at the start from an editor every single day and then we highlight a few specific stories.

It doesn’t have to be incredibly long. That’s not the goal. It’s about what is useful for readers. Provide value for readers every single day. Combine a little bit of personality and then a basic structure.

I work with a team in Vancouver, Canada. They have a website called Vancouver Is Awesome. You can sign up for the newsletter, you’ll see what is there. They are a really good example of a daily newsletter – introduction, five stories every single day, and then something fun to close the newsletter. 

It’s short, usually around 350-400 words, but it’s really useful to readers. It’s enough to start and doesn’t take a million hours to produce. It takes the team 30 to 45 minutes to make every single day.

But what I see with every organization I work with is that email is the best way to build habit and loyalty with their audience. The more loyal readers are, the more likely they are to convert and become paying supporters, and then stay paying supporters for a long time. It’s well worth the investment.

It’s where your revenue comes from if you have a reader revenue strategy. My former employer, The New Yorker, is a good example. They had a newsletter that went out every day and there were a few different people in the team who pitched in and helped make it happen. But there wasn’t really a clear strategy around converting new readers.

They had launched a few different newsletters and needed help figuring out how to take it to the next level. Then they did some research and realized the number one way they got new paying supporters is through their newsletter. 

I always tell my teams that direction is more important than speed. Where you’re going is more important than how fast you get there. It may take a year, two years to build the newsletter – the voice, the audience – and start to see results. It doesn’t happen immediately. You have to be patient.

It works with organizations as big as The New York Times, and as small as really local newsrooms. I’ve yet to see a newsroom that said our investment in email wasn’t worth it. The one rare, universal truth in news today is that organizations that invest in making good newsletters and focus on converting those newsletter subscribers to paying supporters universally see good results from this.

In e-commerce newsletters have been a thing for decades. News media only realized this in recent years. Newsrooms are doing this research and the e-commerce guys are just looking at us like “we’ve done this for years, we know it works well, this is not new.”

I think we’ve seen a rise in newsletters as newsrooms started to pivot towards reader revenue models. If you look back a decade, many newsrooms were selling a [print] subscription of some sort.

Just imagine a hypothetical U.S. or European newspaper. They have a print subscription that people pay for. There is a digital subscription, but maybe no reason to subscribe digitally. No paywall or registration wall – no limit on the content you see.

Over the past three to five years most publications, big or local, shifted towards a pay for access model, including digitally. As that’s grown, we’re seeing more organizations build clear revenue models.

Revenue we get from readers will be the number one driver of revenue for our newsroom, if it isn’t already. So we started to invest in channels that drive that revenue. Facebook, Twitter, and Google drive a lot of audience and if you’re just selling ads that’s what you want. You want as big an audience as possible. It doesn’t really matter where they live – the more people read, the more ad revenue we make.

But when you start thinking about revenue from readers, everything shifts. It doesn’t matter how big your audience is, only how loyal your audience is. Where does loyalty come from? Loyalty comes from building a habit and a relationship with your readers and email does that really, really well.

Organizations realized they need to invest in platforms that support reader revenue and the easiest and most straightforward one is email. It’s not the only way to make money but it is a really clear path to success. Grow an audience, build a relationship, launch a daily newsletter and other products, then start to convert those readers.

Photo by Yannik Mika on Unsplash

The same can be said about podcasts, in a way. My newsroom is experimenting with a companion newsletter to a podcast and we get asked why do we do it. Why isn’t a subscription to a podcast enough? Do you need a newsletter as well? Have you come across something like this?

I’ve seen some examples. National Public Radio is a big newsroom that does this with many newsletters. They have the Planet Money podcast and then they have a companion newsletter, too.

Morning Brew did with their newsletters, they have a podcast that complements their daily newsletter. We did it at BuzzFeed with a few of ours. Even at a smaller level, like Substack, take Simon Owens who I link to in this month’s Not a Newsletter. He has a newsletter called The Business of Content and a podcast with the same name.

These are great because if you have this podcast audience, it’s loyal and there is a relationship too. They make the time for you and then you can say “follow us here on this newsletter because we might ask you questions, engage with you, share additional things we talk about in the podcast.”

A lot of organizations, not just the podcasts and newsletters, would think about this. I have someone as a newsletter subscriber. How can I get them to do one more thing to build the relationship with me? They’re newsletter subscribers, but they also listen to our podcast. They’re newsletter subscribers, but they also came to an event or are coming regularly to our events.

How can we get them to do one more thing? Bring them closer to us, so that when we ask them for the next step to support us or donate, they will really care about us and have a good relationship with us on a few different platforms.

Those are the readers who are most likely to convert. So that’s where that comes in. It’s just an additional way to deepen engagement.

So let’s say someone is reading this interview and thinks, “OK, I want to become a newsletter editor or start this newsletter thing in my newsroom.” I tried to google resources but came up really short. In a recent interview you said that when you started at BuzzFeed in 2012 there were almost no resources for newsletter editors. It’s eight years later and I feel the situation isn’t better.

It’s why I started Not a Newsletter, actually. I started it when I was still at The New Yorker. I didn’t start the Google Doc with the intention of leaving The New Yorker. It was just something I did because I wanted to share things.

I was really frustrated that, at that point in 2019, seven years after I first started working in newsroom newsletters, there were still basically no resources to help people. It was really frustrating and I would get emails from readers and people from newsrooms starting that job.

Someone would get hired as the new newsletter editor at, let’s say, The Economist and I would get an email from them saying: “Hey, I just started this job and I have no idea what I’m doing.” 

I felt like every single time I saw on Twitter or in NiemanLab that a newsroom hired a new newsletter person, 20 minutes later I would get an email from that person like “Hi, I’m Steve, I’m the new newsletter editor. Can we have coffee? Can we talk?”

I realized that even though I’m just 33 I’m one of the oldest people in the newsletter for newsrooms space. Not in terms of newsletters – there are people who have been in newsletters for decades, who know way more than me. But when it comes to editorial newsletters, I’ve actually been around for a little bit.

That’s not good. A 33-year-old probably shouldn’t be like the dean of the newsletter corps. So I started Not a Newsletter to try to help. That was the initial place. Here’s what I can tell you – I do plan in 2021 on releasing a series of digital courses specifically for people who work in newsrooms.

I’ve heard it so many times, too. “We want to launch our first daily newsletter. We want to know how to convert readers, how to grow the audience. Also, we’re a local newsroom and our budget is pretty small. Can you help us?”

I got into this when I left when The New Yorker. When I tell people I’m a consultant, in their heads, they have an idea of what a consultant looks and dresses like or what their goals are. In the U.S. there’s a lot of big consulting agencies and they make incredible amounts of money. So if people think “he’s a consultant” it must mean his goal is to buy a mansion in New York City or a private plane. No.

I got into this because I thought there was an opportunity to help the industry. This is so important. We’re at a moment when journalism organizations around the world have a chance to build a better model for the future. To support local journalism that holds politicians and businesses to account, that acts as a watchdog and serves its communities. I think email can be a really big part of that. 

So I left The New Yorker. Not a Newsletter has been a big part of this, so has Inbox Collective [Oshinsky’s email consultancy – Editor] and the work I’ve done with news organizations. I know there’s more I can do.

I hope this time next year I will have released this series of online courses. So when someone googles “I’m a newsletter editor, what do I do, help!” they can find resources that will actually help them.

There’s only so much of my time to go around. I hope in the future, when someone gets this job, someone will tell them they have to take this class Dan taught. You know: “sign-up for his Google Doc, I’ll share more resources and ideas each month to keep you going, but there’s also this course where you go to start.”

It’s why I got involved with this the past 18 months. I’ve done many talks like the NewsPack one you saw, been a part of the Facebook Journalism Accelerator and got to talk with 150-200 newsrooms through that program. But there’s just more. So it’s a really good question – there should be more resources.

I know there is stuff like a newsletter guide that came out a few years ago. It has been useful for a lot of folks. Membership Puzzle Project helped with a number of guides and resources. We just need more.

Photo by Patrick Fore on Unsplash

There’s this trend of journalists going independent on platforms like Substack. On the one hand, this truly embraces reader revenue, but on the other hand there’s a reason we have publications. When I subscribe to one publication, I get all this news. This unbundling is still a small trend but I already have to subscribe to so many newsletters. What do you think of this “going independent on Substack” movement?

What Substack has done to open up the possibility for individuals to launch a publication is phenomenal. It’s fantastic for the industry. I think there’s a lot that Substack could do to help. I know there are other email service providers and companies that are starting to pop up. So Substack is great, but they also take a really large percentage of your revenue.

I think the competition is coming for them, which means journalists will have more choices. More choices typically leads to better options, better features, better deals, which is a really, really good thing.

I would bet that three years from now, the number of individuals with their own paid newsletter will actually be pretty small. Because building your own paid newsletter requires you to start with a big audience. If you already have it, you might be able to launch your own thing. But it’s pretty hard to do.

We see Andrew Sullivan or Judd Legum (Popular Information) can pull it off because they have a really big audience already. It’s hard to do if you’re starting small. I think there will be a lot of individuals who launch newsletters that drive revenue for them, but not necessarily paid newsletters.

Not a Newsletter is actually a really good example. I don’t charge for it – it’s free and open to everyone. But the number one way I get new clients for Inbox Collective is Not a Newsletter. It drives all of my revenue, my clients, the talks I give. It’s how I make my money, but I don’t charge for it.

So I think we’ll see a lot more reporters, writers, creators who are going to be able to make money off of a newsletter because they’ll have events they can do, because they’ll be selling products like books or classes, because they’ll be able to do a combination of memberships and advertising…

There’s going to be a lot of different ways for people to earn revenue from having a newsletter, building a loyal audience that opens up possibilities to do really interesting things. So one prediction is I think a few years from now you won’t see a lot of individuals making money exclusively off of newsletters. Not like Ben Thompson with Stratechery: “here’s what I charge, read my content and pay for me.”

What I think we will see is a lot more publications that are newsletter based. But it’s not going to be one reporter. It’s going to be three or four or five people who say we came together to cover local news or cover a topic. The primary way we make revenue is off of a newsletter subscription. 

I live on the Upper East Side of New York City. There are some great publications that cover the Upper West Side and Brooklyn. I haven’t seen many that cover the Upper East Side. So if I was to start my own thing, I would say, can I find another reporter that lives on the Upper East Side and could we work together to build an amazing Upper East Side local publication?

We’ll deliver it mostly through a newsletter. We might use something like a Substack to try to build an audience. We might do events, we might have advertising, too. Together we build a publication. I think we’ll see a lot of that going forward in the paid space.

What about Europe? Do you have any advice for anyone in Europe?

As far as Europe is concerned I do think there are opportunities. There’re lots of local opportunities and enough things that are topical.

For instance, I’m thinking of Gonz Sanchez, who writes a newsletter called Seedtable. Seedtable covers the European venture capital market and investment market. He writes a lot about Western Europe, but Eastern Europe, too. What’s happening with technology investment in those companies. There’s an interest across a broad range of folks.

So I do think there are opportunities for you all in Europe. It’s just about making sure the audience is really specific and really clear.