[Podcast] Pushing Send – Episode 5 with Dan Oshinsky

Dan Oshinsky

With nearly the entire world at home, it’s an interesting time to be working in email newsletters. Email opens and engagement is as high as it’s ever been, but what is the place of these newsletters currently? Dan Oshinsky, email newsletter consultant, former director of newsletters at Buzzfeed and The New Yorker joins us to share his perspective on email newsletters during the pandemic.

We kick off the show by discussing some of the unrealistic expectations that brands may have during this time of increased engagement. From there, we move onto how brands and people can find their voice through their newsletters. Dan struggled with his first pandemic email but learned that it’s about adding the right kind of value to people’s lives. The advice Dan gives his clients is that this is a moment to slow down and truly connect with their customers. We then turn our attention to the importance of onboarding and off-boarding emails and how they take readers and turn them into loyal fans. We round the discussion off by talking about some of the opportunities that come with the rise of pop-up newsletters.

Key Points From This Episode:

  • The downside of increased email engagement during the pandemic.
  • Why figuring out the role he plays in his readers’ lives has been so difficult for Dan.
  • The importance of using email to connect with your audience deeply right now.
  • Hear more about Dan finding his voice for his first COVID-19 newsletter.
  • Walking clients through pandemic-related content: Dan’s experience.
  • The valuable lessons Dan has learned about onboarding emails in establishing trust.
  • Learn more transitioning readers using offboarding emails and explaining what comes next.
  • Pop-up newsletters: What they are and how they can be used as experiments.


“People are understandably scared, they’re nervous, they’re worried about what’s going to happen next. And if you can be useful for them in this moment, it’s a pretty powerful thing.” — @danoshinsky [0:02:26]

“The more human you can be right now, the more honest and transparent you can be at this moment, the better.” — @danoshinsky [0:04:01]

“If somebody signs up for your email list and you’re not welcoming them, you’re not introducing them to your voices, your expertise, the way you can serve them, you’re missing an opportunity to win over that reader and convert them into a paying supporter and someone who could be a fan of yours for a very, very long time.” — @danoshinsky [0:17:17]


Links Mentioned in Today’s Episode:

Dan Oshinsky: Website, Twitter, LinkedIn

Ann Handley: Website

David Remnick: The New Yorker

Bryan Kelly: LinkedIn 

Episode Transcript

It’s an interesting time to be working in email because right now with the entire world at home, working from home, what we’re seeing globally is email opens and engagement is as high as I’ve ever seen it in the decade of working in this space. There is just a lot of interest because readers and subscribers are opening and they’re there in their inbox all day. You know when you don’t have the face to face that you have normally with your colleagues, your coworkers, um, email has kind of replaced that so people are sitting in their inbox all day and we’re seeing what email open rates really, really grow

From home-dev.rasa.io the free tool for sending smarter and better email newsletters. This is Pushing Send a show featuring people who send emails their subscribers actually want to read. I’m Bryan Kelly and on today’s show how an email newsletter consultant who is the former director of newsletters at Buzzfeed and the new Yorker has been helping organizations navigate the COVID-19 pandemic. Here’s Dan Oshinsky explaining his perspective on the current landscape of email newsletters. A moment ago. You said it’s an interesting time for email because of COVID-19, but what’s on the other side of the coin with opportunity? There’s also usually threats or risk.

There’s a downside of this, which is people’s expectations for email is very high because they’re getting inundated with messages. The first couple of weeks, the pandemic, so many businesses sent out the how we’re dealing with Coronavirus email and frankly like if you don’t have something to say at this moment, you don’t, don’t say it. A lot of businesses those first couple of days who were sending out emails because they’re competitors, we’re sending out emails so they had due to um, right now the moment is you have a, I don’t want to say a captive audience, that’s not quite the right word, but you, you have an engaged audience. You have an audience that is in the inbox more than they’ve ever been and it is an opportunity to build a relationship, build a habit, and be useful to readers at a time when people are understandably scared, they’re nervous, they’re worried about what’s going to happen next. And if you can be useful for them at this moment. It’s a pretty powerful thing.

Yeah, I completely agree. Now you write and publish your own newsletter called not a newsletter, so how have you tried to be useful to your audience and what struggles have you encountered or wrestled with?

I think the biggest thing is just trying to find the voice. So many folks, and I am among them. When I had to send my newsletter last month, and I’m not going to say I don’t pick my words carefully, but I tend to write pretty quickly. I come from a writing background and I’m able to write a newsletter fairly quickly. At this point, I’ve got a few thousand of them. I’d never taken as long to write a newsletter as I did for the one that I sent out about a month ago. It must have taken me the better part of three hours to write 300 words. I couldn’t figure out what the voice was, what I was supposed to say and what other people wanted to hear from me at that moment. I think that’s the hardest thing right now. Getting to a place where you understand kind of the role that you play in a reader’s life in the subscriber’s life and how you can be helpful to them at this moment. How you can serve them this moment. It’s why honestly it’s not a bad idea just to be quiet right now if you’re not sure what to say, but the thing that I’m seeing across the board, people who work in news organizations, nonprofits, brands is everyone to say, what do I sound like at a moment like this and how can I be helpful? The more human you can be right now, the more honest and transparent you can be at this moment, the better. Now is not a great time to throw out the old kind of batch and blast sort of emails. And that was a really good time though to try to make a personal connection and to think of email as this one to one sort of tool. You know, writing an email. My advice to clients has been write the email as though you’re only writing it to that you know that one reader of yours who might be reading right for them and make it personal. It could feel like a letter. Ann Handley, who is great and has a fantastic newsletter herself and it comes from a great marketing background. She said this great thing about a year or so ago. You know people, when they think about newsletters, they think a lot about the news. They often forget about the letter part of it, which I thought is so, so great. I would encourage you to think about that letter part and to be as human as possible when you’re trying to think about finding your voice right now.

When you were trying to write that first COVID newsletter that you said you struggled with, can you walk me through the process of what you did to feel like you got the voice right?

I went through a couple of stages when I was writing it. To give you a sense of the timeframe, this email was written mostly on an airplane flying back from Austin, Texas. While I was on the plane, the president announced they were shutting down flights to Europe. The NBA season was canceled while I was watching ESPN and Tom Hanks got the coronavirus and that was my flight back cause I was trying to write this huge email. There was a lot on my mind. I think like a lot of folks around the world, on their minds at that point, what I wanted to say in the email and when I ended up landing on after going through that I need to be, I tried being funny at first and it just seemed, it seemed off to try to be funny or make light of the situation. Knowing even then, I don’t think we knew just then exactly how bad this was going to be, but knowing that things were going to get bad, being funny or being sarcastic didn’t seem right.

How were you initially trying to incorporate humor into that?

Oh, that’s a really good question. When I send out my email for a not a newsletter, the subject line is always the same. You know it’s always, the subject line is always the April edition of not a newsletter is here. The may edition, whatever month it is. And I had a very brief moment where I thought, Oh, I should try to be funny in this moment. Initially what I wrote down was the world is ending additional not a newsletter is here. And I chuckled for a second and then thought, Oh no, that’s not right at all. That’s not what people want to hear from me right now. In fact, that would be upsetting for readers to see something sarcastic. And I just switched completely and just went, how can I be empathetic? And what I kind of got to was place where in the email I talked a little about how I was feeling. I tried to take an empathetic tone and now this sort of commonplace, but when I wrote it up, my, my thought was, I’m certainly not the first person to have done this, to try to tell people, you know, I’m scared, I’m nervous, I hope you’re well. I hope you’re safe wherever you are. And I wrote a little about how it felt a little odd to even be writing an email at this moment. You know, is this what people want from me? And it’s funny now looking back, I was about six weeks ago, but when I wrote it, there was a thought in my mind that maybe the kind of thing that I was doing was not going to be all that useful now 714 webinars later, uh, about email marketing and the role that it plays. I clearly mistaken about how much of a need there was going to be for my services and for people to be talking about the role of email. But at the moment I thought maybe I’m not delivering the news to people, maybe I don’t have a role at all. And when I kind of landed on this, let me just be honest with people. If it does feel a little odd to be sending this email, it feels strange. This is pretty unprecedented. And I told readers I’m sending it because I hope it’s helpful and you know and I’d love to hear from you, is it helpful right now at a time like this, I got a lot of nice notes back from readers which was really encouraging to hear and since my of everything that I’ve written is just try to be be empathetic, be personal, be human and write as though a person reading this is your next door neighbor and somebody who you care about and you just want to be, you just want to be good to at a pretty scary moment for all of us

When we come back. How Dan has specifically been guiding his clients during the pandemic to move away from promotional emails and towards truly value based content. Plus Dan talks about the importance of using both onboarding and offboarding email series to move readers through different levels of engagement. I’m Bryan Kelly and you’re listening to Pushing Send from home-dev.rasa.io.

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Welcome back to Pushing Send. I’m Bryan Kelly. Dan Oshinsky has seen how the Corona virus has pushed brands to be more personal and sensitive in their tone and voice, but Dan knows there’s still a tremendous amount of work to be done in understanding subscriber needs and also how to educate and communicate value to them. Here’s Dan explaining one example of this. You shared the experience of what it was like creating your first message at the onset of the pandemic, but can you give me an example of how you’ve been able to walk your clients through the same process?

One example that I’ll give from some news organizations that I work with. Often, and in a way coronavirus has actually pushed many of these organizations to be more personal in their tone and their voice and literally in the, in the people who are sending these emails, sending these emails from a person making it a letter as opposed to before where what I’d seen in the news kind of world was a lot of organizations and if you’ve signed up for a newsletter from literally any newspaper or website, um, you know, or news organization in the past couple of years that it has a subscription business, you probably been bombarded with emails that tell ya special offer 12 weeks for $12 $1 for the next month of 99 cents special deal. It’s president’s day. So it’s our special president’s day new sale, that sort of thing. They’re never from a person, they’re always just from the org and they’re really more about deals and sales than about making a connection. And what I’ve been encouraging all of my clients to do is really just switch that kind of tone. Really just send us a few of those types of generic emails as possible. As much as possible. Talk about, you know, make the, especially journalism organizations make the case for why the work that you’re doing right now matters. Especially in local news. Historically readers had told many news organizations I don’t subscribe because I can get my news anywhere. I I know what the president is saying cause I’m watching CNN, I know what’s happening overseas cause I read the New York times but right now the, you know, CNN and the New York times are probably not going to tell you what’s happening in your neighborhood. So there is clear value for local news and what I’m trying to remind all these organs is step up to the plate right now and make the case for why you have value and why long after this crisis over you’re still going to be committed to serving readers and making sure they know what’s happening, you know on their block in their neighborhood, in their city. The more personal, the better these emails should come from a person on your team. It should make a pretty strong case for why you matter. If not now, then when are you going to do it, exactly? So in a way it’s not a blessing, but it certainly has opened some doors for organizations that had avoided that sort of messaging that had avoided that kind of personal tone to try it. Because you know, just sending out deals is not really enough at this moment. Readers want a little more.

During the month of April this year in 2020 you opened up free office hours to talk coronavirus strategy with folks and I wondered if there was something from those discussions that stood out.

Something that I’ve seen this year that I’ve been writing about a lot on not a newsletter, trying to release resources around and just talking a lot about with clients and and readers alike is the importance of onboarding your readers and talking with your readers and welcoming them. There’s some that we saw at the new Yorker when we kind of came into the assumption at the new Yorker that readers knew a lot about us, that they understood our business, they understood the digital side of things and how we publish there. They knew about our podcasts and newsletters and our crossword puzzle and all these our app, all these different things that we were doing that were really exciting and then you went out and built an onboarding series to make sure that readers understood all these things and found out that readers didn’t understand any of it and that many readers weren’t even aware that published original pieces on the web. It was brand new information to them. We tell them that David Remnick had a podcast and that David Remnick has a podcast? Yeah. Every week he publishes an hour long podcast and interviews with new Yorker writers that you, you know care, read and love. We were amazed at how little readers knew about the work that we were doing. There was a lot of education and that was at the new Yorker brand with a pretty literate and pretty smart audience and with mood at this point. I think 95 years of history, so for me, ever since then I’ve always been a believer in the power of onboarding. How much helps open rates, how much it helps to build relationships with your readers and how useful it is. This is in establishing trust, establishing trust before you get to that point where you’re asking somebody for their support, whether or not it’s a customer or to pay you for the product you sell or a reader to support your news organization. Establishing that trust is so important and onboarding is really, really crucial in that process. And for me something that’s stood out. To go back to your question is how few organizations that I’ve talked to this month really on board their readers that many of them will send a welcome email, but then they’re surprised when readers aren’t converting on or becoming paying subscribers or supporters because well those readers don’t know enough about the org. They don’t know about who they are, what they do, how they support the community. Who are the writers, editors, staff, photographers, designers. Who does the people are who produce this product. They don’t know about the types of work they do or examples of working with pass that might be useful. They don’t know about the impact that your organization has had on the community and so something that has come up over and over again that’s been surprising to me is just how much room there is for growth in the industry in particular in the news space, but this goes across the board with brands and nonprofits too and really thinking carefully about welcoming greeters in that first 30 60 90 days. How do you introduce yourself? How do you start the conversation? How do you make sure that a reader knows how you can be useful for them and using that onboarding series as a way to do and accomplish all of those things. The organizations that I’ve been talking to by and large do very little with onboarding and especially now for news organizations, like I was saying earlier, where people are trying to establish trust and prove that local news matter as well. Heck, if somebody signs up your email list and you’re not welcoming them, you’re not introducing them to your voices, your expertise. The way you can serve them, you’re missing an opportunity to win over that reader and convert them into a paying supporter and someone who could be a fan of yours for a very, very long time.

Yeah, it’s something that gets missed quite a lot and certainly goes way beyond just a single welcome email message. Well, since you’re talking about onboarding, is there a way to shift or transition subscribers the next level of engagement with the brand? You know, maybe something like an off-boarding series?

Yes, it’s a really good question. The answer is yeah, there is. I think it depends on exactly what you’re shifting them to, but I would think about one within the newsletter in the couple of weeks leading up to it, whether or not it’s an intro note in the newsletter, kind of a banner or a call to action at the end that’s pushing people from one product to another. Just being upfront about what you’re doing and then sending a couple more personal notes from a person on your team and editor or a specific voice founder, kind of explaining the situation and what you’re going to do. You know, readers, you don’t want to surprise them with anything. You’re going to have to give them a message a couple of times to make sure they see it. But I think it, what I would really turn to is thinking about using the trusted voices within your organization to step up and say over the course of a couple of emails, one off emails and messages within your regular newsletters, here’s what’s happening and here’s how we can continue to be useful to you or serve you going forward. You works that do a well. We’ll send a couple of these sorts of messages and just thinking about providing value for the reader and you know, at buzzfeed A mistake that we made often is when we do these, we would send like a one off kind of message, just one email and you just did this thing. Now you know, if you want to sign up for another newsletter, click here. They didn’t click. It was just kind of the end of the story and I don’t think we were aggressive enough and frankly upfront and transparent enough with our readers about what we wanted them to do next. So I encourage you to send a couple of different emails, make them from a person in your organization who’s a trusted voice, and talk about what comes next and just really it’s a conversation. Talk them through what you want them to do next and how you can continue to be useful going forward.

Absolutely. It’s a two way conversation. Now, before we hit record, you mentioned the explosion of pop up newsletters during this pandemic. Do you see any new opportunities for that style of email newsletter?

Launching a pop up newsletter can be great if you go into it as an opportunity to learn. Let’s see what we can do. Let’s try a different format. We’ve always done newsletters that are kind of a feed of stories. Let’s do something that’s personality driven. We’ve never tried something that we’re going to grow really quickly, so let’s figure out what kind of tools we have to grow a newsletter super quickly. We’re trying to use a popup newsletter to see if we can start a conversation with readers drive engagement, like we’ve never done it before. It could be great for that, but when you launch a popup, I would think actually about the learnings that you’re going to hear and expect to get from it first. And so a great popup newsletter could it be around Corona virus, but it could also be around down the road and events happening. Your city could be around the election, it could be around the Olympics, it could be around something that you know, a film festival happening in your town. Something brief enough that you can try a lot and throw a lot at it without a lot of risks because it’s only going to last a couple of days or a couple of weeks. But also something where there’s enough interest that readers are going to want to sign up and you’re going to be able to get enough email addresses to learn from. I think with the popups we’re seeing right now going forward, we’ll see probably fewer news organizations and a lot of brands launching popups around COVID news and more launching around specific services that they’re trying to provide to readers during this moment. So for instance, depending on how things go going forward, you may see newsletters popping up to help readers with tips for mindfulness or exercise that might only last a newsletter, might only last a month with exercise tips. You know, here’s a really great newsletter that if I was at Buzzfeed right now with a health and fitness team that was there, you’d be thinking about, you know, maybe we should launch a 30 day coronavirus exercises newsletter to serve readers cause they’re home. They’re looking for ways to work out and be active. Even if they’re home, let’s provide them with that value. And it’ll only be 30 days, but we’ll get a lot of value. You don’t provide a lot of value for readers and do a lot right now or you know, it could be around all sorts of service in your community. I’m seeing organizations that are starting to launch family-friendly newsletters, things to do with your kids while you’re home together, newsletters that are trying to inspire you to cook new things while you’re home. All sorts of opportunities there. They get away from what I think a lot of organizations that continent to at the start, which was, well, this thing is happening, so we need to launch a daily news newsletter to serve our readers. I think as we go forward, some of these products that we’ll see some popups and hopefully see ones that are launched specifically to help you learn, but also ones that are built around a specific type of service for readers, which is a little different, but I think there’s a lot of value there.

Dan’s comments about utilizing popup newsletters in order to be nimble and responsive to the needs of your audience makes a ton of sense. It’s a chance to go deeper with subscribers and even potentially offer that pop up as a service or product. Coming up. On our next episode, we’ll hear from Joanna Wiebe, the founder of copy hackers, who is also the originator of conversion copywriting, which our guests Lianna Patch mentioned back in episode four of season one. Joanna talks about how lots of people are great at building an audience with a really good email newsletter, but missed opportunities to effectively sell and promote their services or products. You won’t want to what Joanna tells me during our conversation. So if you’re listening to Pushing Send for the first time, be sure to subscribe at Apple podcasts or wherever you’re listening so you don’t miss an episode. And if you’ve enjoyed what you’ve heard, I’d encourage you to check out a few other episodes while you’re here. Lastly, leaving a review will help us share these stories with others like you. Thanks in advance for doing that. I’m Bryan Kelly, and you’ve been listening to Pushing Send from home-dev.rasa.io. 

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