Delivering Episode 9: An Interview with Dan Oshinsky on BuzzFeed, The New Yorker, and Email in Journalism

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In this episode of Delivering, host Jason Rodriguez chats with Dan Oshinsky, the former director of newsletters at The New Yorker and Buzzfeed, and current proprietor of Not a Newsletter and Inbox Collective. Dan and Jason dig into email’s role in journalism, how to vet newsletter ideas, what email professionals should stop doing, and embracing Google Docs.

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Episode Transcript

[00:00:00.870] – Jason
Welcome to Delivering, a podcast about the email industry. Delivering is brought to you by Litmus, the solution used by over 600,000 email professionals to build, test, and analyze better email campaigns, faster. Today I’m joined by Dan Oshinsky. He’s the director of newsletters at The New Yorker. He’s creator of one of my all time favorite resources, NotaNewsletter.com. And we were just discussing before recording that, if we’re going way back, he was one of the first speakers at the very first Litmus conference—The Email Design Conference—all the way back in 2013. So welcome to the podcast, Dan.

[00:00:34.320] – Dan
Thanks for having me. I so appreciate it and 2013. Is it possible that it was 2013?

[00:00:40.130] – Jason
Yeah. It’s wild to think about. That was the first, dinky little one in Boston. It was an awesome experience. I remember you were talking a little bit about starting up the BuzzFeed newsletters, if I’m not mistaken, and I remember there being cats involved and all kinds of cool things.

[00:00:54.980] – Dan
On Sunday, we had just launched “This Week in Cats” newsletter which I remember presenting in London about it and the crowd going, in my head, the crowd went wild. I’m sure the actual response was more tepid but in my head I remember leaving and thinking that is what it must feel like to be Mick Jagger.

[00:01:13.540] – Jason
So I want to talk a little bit about your history because you don’t necessarily come from an email background. It seems like you come from journalism. I know you did, way back in the day, Rocky Mountain News. You had your own project, was it Stry.us? And from there you joined up with BuzzFeed. You’re now the director newsletters at The New Yorker, so kind of walk me through your history and how you came to be in the email marketing space.

[00:01:45.150] – Dan
So it was very much by accident. I went to journalism school at the University of Missouri and the whole reason I’m going to J school was to figure out how I could learn the skills and then come to newsrooms that were trying to transition to the digital age and support them in that mission to help them go through these types of transformations. They needed to really adapt to the Internet.

[00:02:09.270] – Dan
And over the years I was, when I worked at the Rocky, I was just there for a summer, I was their correspondent. One of their correspondents in Beijing at the 2008 Olympics doing blogging. I remember they told me about the potential there. They said, “We’re starting to have some reporters on this thing called Twitter. It’s interesting we’re not really sure what it is. Maybe there’s a possibility there.” And after college I worked at a TV station in San Antonio. I did some reporting in Biloxi, Mississippi on the anniversary of Hurricane Katrina and the five year anniversary. This became Stry.us, which was this long form kind of reporting project that was supported by the University of Missouri and I had some reporters down in Springfield, Missouri later.

[00:02:53.610] – Dan
And somewhere around there was when we launched a newsletter to support Stry.us that did really well. People seem to like it, it was a good way of delivering stories. We had been collecting all of these tools and apps and things that were useful for reporters and decided. Maybe we should go out and launch some sort of product to help reach an audience and help reporters find some tools and thought OK well let’s start a newsletter. So we called it Tools for Reporters and it’s still going at ToolsForReporters.com. Some Mizzou grads four years younger than me have picked up the torch and really run with it.

[00:03:26.850] – Dan
And it did incredibly well and it grew an audience and people responded well to it. I loved the back and forth of email. The idea would actually build a relationship. People would write in with their ideas things that they were working on. It was just such a nice way to start to build a small community. And then, BuzzFeed came around. That was at the end of 2012. BuzzFeed was really growing starting in 2012 into this little powerhouse on the web. It was growing a ton, growing month over month in a really rapid way and starting to push into serious news and long form reporting.

[00:04:04.320] – Dan
So I had reached out just to say hi. I was really curious, the students that I worked with at Mizzou all loved BuzzFeed. And I didn’t know a lot about it frankly in 2012. But I reached out because I was curious why this website that did cat videos was suddenly really excited about news and really hit it off with their team and they came back to me and they said, you know, let’s try to figure out an opportunity. So I started thinking about the BuzzFeed story. Jonah Peretti, who is the founder of BuzzFeed, about 20 years ago had this amazing kind of viral experiment where he sent around an email around Nike and shoes made in sweatshops that went viral and won big back in the day when chain email was a thing that could still exist.

[00:04:46.410] – Dan
And BuzzFeed was really built around this idea of telling stories that people would share. And I came back to Buzzfeed and said email is really the original source of sharing. We had some success at Stry.us with newsletters. Tools for Reporters was doing really well as a newsletter. I think there might be an opportunity for us to build something here. And on top of all of that, the other thing back in 2012 was, you know, we can’t necessarily rely on channels like Facebook or like Google to be consistent sources of traffic and audience and that’s their audience.

[00:05:19.350] – Dan
It’s, you know, they write the rules and if they change the rules if they decide they don’t like us one day, we’re out of business and email gives us an opportunity to really build relationships for the long haul. And they were into that. So I came on board and you know my story with BuzzFeed was my first day at the office. I know our CTO brought me to my desk and said, “Do you know what you’re supposed to be doing?” I replied, “You know I was really hoping you guys would tell me!”

[00:05:47.370] – Dan
BuzzFeed had a handful of automated newsletters that were no good and you couldn’t read them on a mobile device. And they were built around kind of weird, they were just RSS e-mails. So we just tore everything down and started fresh. And over the course of five years built a team, grew a team and email into one of the biggest sources of referral traffic at BuzzFeed. It was an incredibly important source for us, we launched dozens of newsletters and automated products. We ended up launching emails in six different languages and email became a really powerful force in the company.

[00:06:24.450] – Dan
And then, The New Yorker came calling back in 2017. At The New Yorker, email was, still is, one of the biggest sources of referral traffic. The number one way we take casual readers of The New Yorker and turn them into paying subscribers, a huge, huge source of digital revenue in terms of ad revenue. And The New Yorker said you know, this thing that’s a number one in all these different categories, we should probably have someone running that, in charge of that. So that’s how I came on board to The New Yorker.

[00:06:54.880] – Jason
So let’s go back to BuzzFeed a little bit. I feel like that’s such an interesting story. So you’re the first person dedicated to email there. After four or five years being there, what did the team structure look like by the time you left?

[00:07:09.900] – Dan
So when I started, it was just me sitting with our product and data team to try to figure out what the emails would look like after we built out the structure and templates and kind of the base to work off of. I ended up moving over and sitting with the editorial team but there was always sort of a partnership there between us and product and data which was really important in terms of my team. By the end there were five of us who worked on email. Email was really centralized under my team. Some of the folks my team would send emails, work on email, work with other teams on email strategy and then we always had partners on the product and data side to help support the mission.

[00:07:45.450] – Dan
I’ve really found over the years—especially in an editorial operatio— that you need to have not just the folks on the edit side thinking about the strategy, kind of the outward facing stuff with the email, what the emails look like what’s what, what what kind of content we’re promoting, what should our email strategy be in terms of the types of newsletters we have, but also focus on the product and data side to make sure you’re measuring emails in the right way. You’re asking the right questions. You’re building the right tools to grow your email lists and get the most out of email.

[00:08:14.430] – Dan
That partnership is so important. So by the end that was kind of a core team, about five of us. But then there were literally dozens of people around the company who just got involved who were part of our orbit.

[00:08:25.890] – Jason
So you mentioned the data team especially being important. Do you have like a set strategy or anything when it came to testing out newsletter ideas or experimenting within newsletters? How did you go about testing things?

[00:08:39.370] – Dan
It’s a really good question. So something that I learned from my first boss at BuzzFeed, an incredible person who’s still there, Dao Nguyen, and Dao taught me so much about testing. Dao, I think, is one of the smartest smartest people in media and work’s kind of behind the scenes but those of us who work with her in BuzzFeed know that she knows everything when it comes to testing. So Dao is somebody who really encouraged us to think about how to test kind of small ways. So for instance if we had a daily newsletter, let’s say, or do your daily newsletter goes out to one hundred thousand people.

[00:09:18.090] – Dan
We were testing out a new type of concept. We wouldn’t do just a straight 50/50. What we would do is, we’d say, let’s set aside about 20 percent of the audience. We kind of moved them to a separate sort of segment. And then over the course of the next couple of weeks, the next month, whatever it might be depending on how big the list was, let’s just test on these folks and let’s be upfront with them about what we’re testing. But we’re trying make sure we’re asking for feedback so we’re getting that kind of anecdotal feedback on top of the data and using all of that to really decide what’s working and what isn’t.

[00:09:48.330] – Dan
The way I think about it now is, If you’re a restaurant and you’re testing, if you’re Burger King and you’re testing out the Impossible Burger, then you know they don’t go and roll that out to five thousand stores right away. They say, let’s see what happens if we try this out in Columbus, Ohio for a few weeks. How do people react? What do they say, what do they tell us? And it’s kind of the same sort of thing with email. Take a small segment of the audience and test it out and try it. See what works, what doesn’t, get their feedback and then make decisions about what we want to do next. We roll out another set of changes to this audience. We roll it out to everybody and it’s what I did here when I got to The New Yorker. We had a newsletter tied to our old Cartoon editor, Bob Mankoff. Bob left The New Yorker and suddenly we had this big list of people who would be used to getting occasional dispatches from Bob. Bob didn’t work for us. So we couldn’t just keep sending out the Bob email.

[00:10:41.040] – Dan
So we had to figure out what to do next. And The New Yorker actually kind of amazingly didn’t yet have a newsletter built around humor. We had a Bob email. So what we did is we took a segment of that audience, it was a pretty big list, I think was about 10 or 15 percent and it was in the tens of thousands of people, and we shot them a note and said we’re going to test out something different for the next month. We want to try out a daily humor email. It’s going to include these types of elements. Here’s the first one, you’re going to be getting this the next couple of weeks, we’d love your feedback. And every week or so we’d ask, you know, hit reply tell, us what you’re thinking. You’ll like it. We looked really closely at the numbers and we compared it to that. And I believe it was a monthly product basically that we were sending out every other week product that we were sending. So what we were doing, two emails a mont,h were just kind of the cadence the team was already working on with this Bob email, trying to figure out what a humor product might be versus a daily product tested out for a month and found at the end of the month, 1) far more people were actually opening a daily email than opening a twice a month email. We were actually increasing opens even though we were sending more frequently. You’re driving far more traffic and the response is like 85 or 90 percent of people who wrote back to us said I love this. Why hasn’t this been the email the whole time? It never happens, you never get that kind of response rate I expect like when I did at BuzzFeed. We would launch a new newsletter. We test out a new design. And the response would be go back. I don’t like this. Yeah I liked the newsletter the way it was before and then after a few weeks they come back around and say I’m starting to get used to it’s growing on me. And then six months later if we tried a new design they’d say why are you changing the design that I’ve loved for years and years and years even if we’d only had it for a couple months.

[00:12:21.140] – Jason
Go figure. So it the feedback you collect, was it just through replies to the email? Did you ever do any like surveys and stuff?

[00:12:31.120] – Dan
OK. We would, and those were always, and this goes back to my BuzzFeed days. Any surveys that I do are always short. Almost never more than five questions. And I literally make the team take them when we do something like this. I go around and ask some people at the company, will you take this survey and time yourself and see how long it takes you to do it? Because we tell people the survey will only take two to three minutes and it takes somebody 15 minutes. That’s just a lousy customer experience. I want to be upfront with people and I don’t want to waste their time.

[00:13:00.680] – Dan
Typically you know I don’t need to go through, I don’t need to put folks through a series of hoops or steps they don’t need necessarily to to get the kind of feedback about whether or not an email works. I may not have to ask a reader to tell me their age or where they live what kind of job they work. I just want to know what do you like about the email. What didn’t you like. Would you forward this email to a friend? If so why and was there something that was missing? Was there something you wanted? Usually in a couple of questions I can get to the heart of the matter.

[00:13:29.150] – Jason
Yeah totally. So you just briefly mentioned like, would you forward this to a friend and that kind of makes me think about just the growth strategy around Buzzfeed and The New Yorker. What are some of the things you do to grow that newsletter or any of your newsletters you have? Do you offer freebies or do have specific tactics you use to grow a newsletter especially if it’s something that’s just from scratch that doesn’t have a Bob newsletter behind it?

[00:13:56.660] – Dan
Yeah. So at both places organic growth has really been at the heart of what we’ve done, trying to figure out strategies to capture what’s a pretty large audience in both places and convert those people to newsletter subscribers. So that could be sign up units at the bottom of the story. It could be pop ups ,fly ins, a little toaster unit that pops up from the bottom of the screen to try to capture folks when they’ve reached a certain level of engagement with us. At every place I work we’ve never run pop up units that that appear upon entry to the site.

[00:14:32.060] – Dan
That’s the thing I probably, and I think most most readers of sites, say they hate the most and nothing worse than going to a website the first thing you do is having one. Yeah I had one the other day I was on a major news website that I will not say now to protect the innocent but, in the course of 90 seconds of being on their website, I was hit with four different pop ups. And at that point you know I exit out of the first one, the second one, then at a certain point I say I don’t think I’m going to read your website, it’s not worth it.

[00:15:03.620] – Dan
Yeah it’s not worth it even if they had a story that was the secret of life is we have discovered it. At some point I’d say it’s not worth it. Too many pop ups, I’m sorry. I’ll figure it out on my own. I’m sure, I’m sure someone will tell me if it was that important or that useful. It was a lot of organic growth. Thinking about you know a place like BuzzFeed and here at The New Yorker, too. We didn’t really have places that were a main newsletter, basic stuff, where is the main newsletter page where we can highlight all products? Are there individual pages that we can share on social channels and and through email? Thinking about how we cross promote from one existing product to another.

[00:15:43.790] – Jason
You already like one of our e-mails, our daily newsletter. Maybe you would like this new product relaunching around books, fiction, and trying to really take advantage of the onsite kind of opportunities to capture readers at the right moment. At The New Yorker we’ve started to build in some paid marketing strategies to figure out if there are opportunities for certain types of very engaging products. Can we target the right people in places like Facebook and bring them from one source of referral traffic? Facebook, which is good, to another like the newsletters which are a little more consistent and typically drive stronger results for us.

[00:16:20.750] – Jason
Totally makes sense. Between BuzzFeed and The New Yorker, obviously those seem to me like very different audiences. Is that true in the first place and if so what were the biggest differences in what kind of content they liked or how they consume those different newsletters?

[00:16:39.980] – Dan
So the audiences are more similar than you would think. Now the New Yorker, and I loved my time at BuzzFeed and I have so much respect for BuzzFeed, this has nothing to do with them and the types of content they’re producing. The New Yorker is just on a slightly different level when it comes to the storytelling, the reporting, everything. But there are a lot of themes in common. New Yorker readers are really interested in news, commentary, humor, and culture, which is what BuzzFeed did just attacked from a slightly different perspective than over at The New Yorker. We wouldn’t do the quizzes. We do some video content. We do. We have a great podcast network. It’s just a little different than the way BuzzFeed would approach content.

[00:17:25.770] – Dan
The biggest thing for me here at The New Yorker was really adjusting to from BuzzFeed which was very much a startup. When I started at BuzzFeed there were about one hundred and seventy five people in two offices and over the course of five years it grew to I think something like fifteen hundred employees and about 20 offices around the world. The New Yorker is an almost ninety five year old institution with a lot of rules and a lot of structure for a good reason.

[00:17:56.050] – Dan
We put out a magazine forty seven times a year. And in order to put out a magazine that’s the length and the quality of ours you have to have a lot of rules and structure to make it go and keep things going. Otherwise we’d just be chaos every week. Having run only just a high school newspaper and having no other experience besides that I know what chaos is like. I’ve seen the other side, what would organization structure look like, organization and structure tends to work a little better. But the biggest change for me between the two is really not the content but adjusting to the type of workplace and trying to bring a lot to what we’ve done the last couple of years.

[00:18:29.740] – Dan
The New Yorker is trying to bring a lot of really smart digital folks and try to use that to take the mission of The New Yorker and expand them into places like email where there is an opportunity to build a relationship over email, grow our audiences, reach people who maybe hadn’t been reading The New Yorker before and kind of bring people into our orbit.

[00:18:50.600] – Jason
Make sense. So you said at BuzzFeed there were about five people on your team and then a dozen or so that help out. What’s the team look like at The New Yorker that’s working on email?

[00:19:00.990] – Dan
At the New Yorker, it is very much a hub and spoke kind of system, kind of the hub of the network. I oversee email strategy, newsletters strategy, and then work with people across these teams from editorial, audience, development, product, data, consumer marketing. At a company like The New Yorker, consumer marketing of the folks who should ultimately pull out your credit card and pay for a subscription sales. All these different events, all these different teams for whom email is really important. Working with them to coordinate the strategy build out a strategy and actually get our emails out day after day.

[00:19:37.480] – Jason
Nice. So I am curious, how I feel like you talk about this in Not a Newsletter and link to resources around strategy and now I’ve seen a lot of docs around, like, here’s what you should be thinking about when starting a newsletter. So say somebody at The New Yorker comes up and says, “I have an idea for a newsletter.” What are the steps you take to make sure that idea works and then grow it into a full fledged newsletter that’s really effective?

[00:20:06.450] – Dan
So there are a couple of things that have been effective. One is, it’s a resource that I have in Not a Newsletter every single month. It’s this strategy positioning doc. Which has actually been something that’s been going around in recently in the editorial email world for a little while and I kind of took it and helped formalize it. But this is a doc that we’ve used to try to ask a couple of big questions upfront around who is the audience, how are you going to measure success, how frequently does it go out? This newsletter, where does it fit within our existing suite of emails? The New Yorker, we have 14 newsletters right now. We have a lot of emails. So if we’re going to add something, what does this email do that our others don’t? What kind of new territory, what kind of new ground are we breakin? And we do that for a couple of reasons. One is a lot of the times that people say they’re interested in launching a newsletter, they’re not all that interested in actually doing the work to launch a newsletter. It’s something I had seen that is not unique to this place.

[00:21:04.600] – Dan
People get excited about an idea, so great, I want to do this and they’re hoping for someone like me to then go and turn this into reality and then they can take the credit for it down the road which is great. But often you know the sort of strategy positioning doc helps kind of separate the wheat from the chaff. You get a sense of who are the folks who actually kind of want to go for it and have an idea. Or was it just a spur of the moment thing they had on the way in on the subway ride into the office, I thought I should launch a newsletter because often what people say is I’ve heard that newsletters are an amazing way to get traffic to my website. But it’s not like I have just a million people in my back pocket or I go, “Oh yes they’ve actually all been waiting for you to launch this product.” I always tell folks if, the motto in the office is, if you’re launching a newsletter for traffic related reasons you’re launching it for the wrong reasons.

[00:22:02.910] – Dan
You have to be thinking about building relationships and what kind of stories you’re actually telling. Are you utilizing email in a really interesting way and a powerful way or is this just I just want to email readers a few of my stories, please click that sort of thing? It’s not all that useful right now in 2019. So we usually start with the positioning doc, if they go forward they’re excited, then we start to have conversations and often what we’ll do is we’ll do some tests internally, first post and we’ll build some test emails, send it around to some smart folks see what they think.

[00:22:37.260] – Dan
And then if we go from there and we decide we want to launch, we launch from zero. With these we’ll launch and have no subscribers and we’ll start to promote on other channels and often we’ll set a kind of a time frame for how we want to run this newsletter. So if you’re making a commitment, typically it’s at least six months if you’re going to set sign up and you’re gonna say I’m going to be writing this newsletter every week, every other week, every month. It’s a six month commitment you have to stick with that.

[00:23:04.170] – Dan
And then at the end of six months we see where we are. How are readers signing up? Are they engaging with it? Are they opening it? Are they clicking through to stories? Are we getting good feedback from readers? If we did a survey what did the survey reveal? And for the writers and the editors who are a part of this, do they like it? Is it useful for them and then trying to either say this is great. We need to iterate tasks and improve or maybe if this product isn’t working for x y and z reasons and it might be a good time for us to sunset it, when the audience is still small, when we’re still growing it. And we have an opportunity to say you know thank you for signing up. Thank you for being a part of this. You know this was the last one of these emails but you can always sign up for these other products that we have and stay in touch with The New Yorker. Sometimes, when things have gone on for a long enough period of time, it just becomes part of the fabric of the company. I see companies who say we can’t we can’t kill this newsletter.

[00:24:00.960] – Dan
Well why not? Well we’ve been doing it for seven years. Yeah well do you like the newsletter? No nobody likes it. How does it operate? Pretty poor. Are people signing up for it? Nobody does. So why are you sending it? Because it’s the thing we’ve always done. And the thing we’ve always done is often not the thing you should continue doing but it takes time to get to that point and for the light bulb to go off and go oh well we can make a change we could do something different or in some cases, and we’ve had a couple of these at The New Yorker, when I got here they had just launched this newsletter called The Week in Culture and The Week in Culture was a review of the week in culture and, to be honest, it wasn’t doing that well. The writers didn’t like writing it because every week it turned out they just wrote about what Donald Trump said about what was happening in culture. And so it was almost more of a cultural writer writing about the news than an actual look at culture. The framework didn’t really make a lot of sense, readers weren’t quite sure what they were signing up for. And we ended up taking that audience and trying something different that we called The New Yorker Recommends which was a totally service built product.

[00:25:10.890] – Dan
Let’s help you find books podcasts, movies, TV shows, things that you can actually consume. We know there’s a lot of all of this. It’s tough to find good new things that are worth your time. So let’s use all of our staff as a resource. We read, watch, listen to all sorts of interesting things, we’ll pick out the best and we’ll send you them every week and we flip the concept from this kind of strange sort of culture review to recommendations and really started promoting it. And it just, it took off with the audience over the last year or so, has quadrupled. The open rates went from about twenty four, twenty five percent to north of 40 percent. And I think it’s up to like 40 to 43 percent and really responded in a big way to this product because they suddenly got what it was for. They understood why they would sign up for this and how The New Yorker could help them. So sometimes there’s opportunities there to pivot out of something that’s not working and something that might work.

[00:26:05.700] – Jason
So I’m curious what the success rate is like for that kind of strategy. How often are people coming to you with these newsletter ideas, how often are you committing to that six months, and then what percentage, you said you have 14 active newsletters right now, what percentage actually makes it through and sticks around for the longer term?

[00:26:25.540] – Dan
So we have right now 14 newsletters I’d say of the ones they have only been a couple maybe three or four that have either been pivoted to another sort of product or just outright we stopped sending them. Most of them make it through though at a certain point when we get excited enough about our product and I’d like to think that over the years of doing this I’ve gotten pretty good about trying to identify things that I think can work. I’m not going to waste our team’s time with something that I think isn’t going to work.

[00:26:59.850] – Dan
A good chunk of them actually make it through and keep going. There were a couple that we pivoted, different sorts of strategies like Bob’s newsletter be did become this great humor product that goes out five days a week, most of them actually do make it through which has been nice. At BuzzFeed, the hit rate was much lower and we were new, I was newer to the space, we would try ideas that we thought would work and didn’t. I’ll give you an example: We had this product that we were really excited about that was a celebrity driven newsletter. We really thought it was gonna work well cause celeb coverage does well on the site and it kind of tanked as a newsletter. What we discovered was celeb coverage really worked better on other channels like Instagram, like Facebook, like Twitter, where there was a little more of a conversation, celeb news moves pretty quickly. It’s also, there’s a lot of celebrity news and it happens. You know if you follow the US Weekly and those types of sites or the BuzzFeeds there’s new celebrity news every 20 minutes.

[00:28:05.450] – Dan
The TV news of the world, it is celebrity news, is kind of disposable. There’s not a lot of celebrity stories that really tend to last. And that as a product didn’t really work. We did however and I am really pleased about it end up deciding there was a way for us to cover celebrity coverage, to get to cover celebrity news, and the way to do that. And this was an extremely BuzzFeed kind of product and still amazes me that The New Yorker hired me after doing this. But we had a guy on my team, his name is Lincoln Thompson, Lincoln was super bright and Lincoln said you know what we should do.

[00:28:39.400] – Dan
Our audience loves every time we do these kind of. We do these posts on Buzzfeed that talk about celebrities and showcase them in whatever insane attire they are wearing or no attire at all. We should do a newsletter where we talk about celebrities but through kind of like we fawn over them in an interesting sort of way. We should call it Dude a Day and we should send you a dude every day. And we tested it out and the celeb newsletter that never did well but Dude a Day became a very successful product for us.

[00:29:14.230] – Jason
I obviously was looking into some of your work and stuff and I think you still have your BuzzFeed page on all of your articles. And that was the one that pops out because the featured image is just a naked guy laying on a bed with like a one of the BuzzFeed bubbles or something over his ass.

[00:29:37.120] – Dan
Right.

[00:29:37.360] – Jason
And I was like, “All right, Dude a Day. That’s that seems like an interesting, very BuzzFeed, thing to do.”

[00:29:44.450] – Dan
I think by the end of my time there, I can’t remember if it hit a hundred thousand subscribers. It did very well. People understood it. It was simple. It was built for email, you got a photo of a celeb, a weird little thing about them. You were in and out. It was fun and silly. It was a good place for quizzes. The audience really just connected with it in a great way. We got reader feedback.

[00:30:11.110] – Dan
It’s the silliest thing but it worked really well. But you know, my first day at BuzzFeed I pitched three newsletters: a daily newslette,r a long form product, and an email called This Week in Cats. And people laughed at me for pitching an idea called This Week in Cats and it grew to be one of BuzzFeed’s most successful newsletters.

[00:30:38.120] – Dan
The way I put it now, which is a little more sophisticated I’d like to think than how I would have described it a couple of years ago, is when you’re building email you have to think about what you do uniquely well. At BuzzFeed, we covered cats in a really unique and interesting way. We also did the same with celebrity coverage. We did the same with coverage of fitness and healthy eating. Those were all things we did well and we tried to lean into them and build products designed around those audiences.

[00:31:07.990] – Jason
I’m curious to contrast these two things, what was your favorite email newsletter you sent at BuzzFeed and then what was your favorite at The New Yorker? I’m curious if there is a correlation there or if they’re just completely different things.

[00:31:25.540] – Dan
You know I do love This Week in Cats. That was one of, that was one of my darlings, and I said I’m awfully fond of that one. The other one that I still love to this day, it was it was one of our first automated courses. I worked with one of our then writers, she’s now still an editor there. Her name is Augusta Falletta and we worked with her on this course called The Seven Day Better Skin Challenge. And it was an automated course, sign up today, tomorrow, a year from now.

[00:31:49.630] – Dan
Look get these seven days of content around skin and around, you know, taking care of yourself in a really interesting way. And it was thoughtful and smart and the tips were really good. And the response to it was amazing. We actually ended up using it later as a product when we were thinking about launching in a new language, we would take the Seven Day Better Skin Challenge, translate into say Portuguese, launch in Brazil before we had any newsletters to see, does this work because we knew what worked so well in the US.

[00:32:21.310] – Dan
Well we’ll see if there is an audience, if we build an audience then when we do launch a newsletter. Well we’ll have an audience that we can actually reach out to and say hey we launched a new newsletter. Click here to sign up for our, you know, our Healthy Living newsletter or our food newsletter or whatever it might be. And the Seven Day Better Skin Challenge was an incredible, incredible success for us. I’m partial to that one. At The New Yorker, the two that I’m really most proud of are Humor and Recommends because they served really unique audiences. Recommends in particular is a product that we had never really tried anything quite like it before.

[00:32:59.500] – Dan
The New Yorker often kind of takes a fairly neutral ground when it comes to covering books and TV and movies and there’s even cases where you know you’ll read a movie review and at the end go, did they like it? Was it good or what? And this gave us an opportunity to say these are the things we like, these the things we think are great, really positive, be upfront with folks and help them find stuff that we think is gonna be useful.

[00:33:29.350] – Dan
And that’s been really fun. We’re still trying to figure out how we continue to extend that sort of product but I’m really, really pleased with that one.

[00:33:36.460] – Jason
That’s awesome. So, what do you think, and I feel like I might be kind of skewed because you’re definitely in the media world, in the news and journalism. So this might not apply to everybody, but what do you think is the biggest opportunity for email markers today?

[00:34:04.330] – Dan
So there are a few things that I think are really interesting at least on the technical side of things. I’ll give you the non sexy answer and then I’ll give you the content answer. On the technical side of things. Actually a lot of publishers who are still fairly new to the space haven’t really thought about how you onboard readers and how you win them back. And that’s something we really focused on, particularly here at The New Yorker. How do we bring people into our world, showcase some of the personalities, the voices, the types of stories we’re gonna have? Because lots of readers are familiar with The New Yorker as a brand. But many of them may not be frequent readers, may not be longtime readers. So we have an opportunity with onboarding to really bring them into our world and showcase what it is we do. There’s also frankly a lot of readers who think of us still as a magazine, as a weekly destination, and don’t realize that we publish on a given day 10 to 15 original pieces on our site. So there’s an opportunity there to kind of showcase the full breadth of what we do and with reactivation just think about how you win them back.

[00:35:03.810] – Dan
So many of the folks in the industry I talk to what they’re struggling with is deliverability and the deliverability problems are often usually linked to either we didn’t onboard people in the right way and we didn’t actually try to win them back when they became inactive. Those are huge, huge opportunities. The other thing I’d say are really products built around personality. This is something, now Tinyletter was the first in the space to do this. The last year or two some of the newer products that have popped up like SubStack and Revue have been great because it’s really made it so easy for anyone to launch a newsletter and to get started.

[00:35:44.440] – Dan
So there are lots of personality driven newsletters outside the news organization space but inside thinking about how you take some of the voices and personalities at The New Yorker, here we have a guy like John Cassidy who is a writer who covers news, politics, business from a really interesting, progressive, perspective and giving him a platform to have a weekly newsletter where John, every Saturday, sends out an email. It’s John Cassidy’s reading list, here’s what I’m reading and here’s some commentary and thoughts about things happening in the news. It’s great. Readers love it.

[00:36:15.300] – Dan
It extends his personality and builds a relationship, it feels very email, it’s built for email. It’s not built really as a column, it’s built to be read in email. It works great and thinking about how other brands can take some of those personalities and unique voices and showcase them through email eyes.

[00:36:31.770] – Jason
If there’s one thing that you think more folks in email should be doing, what would that one thing be?

[00:36:39.110] – Dan
That’s a really good question. Onboarding and reactivation should be in that conversation. That’s a really, really good question. Honestly I think the thing that everyone should probably do at some point is actually take a step back with your email program and look at the types of newsletters you’re sending and think really critically about what emails work, which emails are working, and how you’re measuring success. So many companies are still just thinking about email and email success as a, was the open rate good? If yes, great.

[00:37:22.000] – Dan
If no, we have trouble, and trying to think about what are the other metrics out there that we’re going to use to measure success. At a place like The New Yorker, we’re thinking not just about open rates but we’re thinking about click-to-open. We’re thinking about growth. We’re looking at mobile open rates to make sure the audience is actually moving with us to the mobile space. We think really carefully about engaged minutes. New Yorker stories are really long. We publish, there’s nobody else in the industry who’s going to publish a six thousand word story on an obscure Polish novelist. We will happily. We write stories that are long about what’s happening at the Met or what’s happening at the opera. We write really interesting, in-depth, thoughtful pieces which I think are worth reading and worth people’s time. But you know we cover stuff in our, in a different sort of way. And some of our pieces are very long. So we look at engaged minutes. Are people actually coming from our newsletter to the site and actually reading? If we push people to read a story that’s 10,000 words long on Elizabeth Warren, did they actually hang around? Did they read it? Did they use email as a way to find great stories to read or were they bouncing out pretty quickly and saying the story’s too long, the story isn’t worth my time? All of those are interesting signals too. I think getting beyond open right. Moving beyond open rate, asking questions about what’s working, what isn’t, and which metrics are the ones beyond open that we can use to measure success.

[00:38:49.080] – Jason
What is one thing you would say more email marketers should stop doing? What’s the reverse?

[00:38:54.060] – Dan
Oh this could be its own separate podcast. One thing I think. I think. Oh goodness what should we stop doin?. I don’t even know which one I want to choose now because there are so many. I’m going to give an unusual answer. I think there is a trend that I’ve seen in the last couple of years in the industry where companies say our email program isn’t working. So what’s wrong is, and then they’ll pick, they’ll pick kind of a scapegoat. Often it’s the ISP, the email program isn’t working, our emails aren’t being opened.

[00:39:32.560] – Dan
It must be the ESP’s fault. Let’s go through this whole thing to switch to a new ESP. We’re going to migrate over. We’re on MailChimp, we’re going to move to Campaign Monitor. This will magically fix all our problems. They sell it in their company. This is the thing that will fix all of our problems. Then they switch. They’re still using the wrong strategy from before, a year and a half later they say this isn’t working. Our ESP’s to blame. Let’s switch. We’re gonna go over to Cheetah Mail and then the cycle repeats. I’ve seen a couple of these happen and it’s hard. It’s often not the tools. It’s the way you’re using them, it’s the strategy you’re using. The tools are often very powerful and have great opportunities there with the right strategy in place and I think if there’s one thing people should really think about, it’s taking a step back and actually looking at the program and saying are we doing things the right way? Do we have the right types of newsletters?

[00:40:25.210] – Dan
So many companies are sending these kind of RSS sort of emails. Here’s just a feed of my stories. It’s not useful anymore. The email space is so complicated. But it’s also very competitive and there are more emails in people’s inboxes than ever before. More good emails in people’s inboxes than ever before. And the bar has been raised for success and the expectations for readers are much higher than they were five years ago or 10 years ago when we started doing this at BuzzFeed. People were surprised that our emails were like personable and subject lines were fun and occasionally throwing emoji or GIFs, people just thought it was mindblowing to see your brand actually or at least in the news space try things that were a little bit different, things that were friendly, things that were personable, things that had a lot of voice.

[00:41:15.150] – Dan
But most of the brands are doing that now. So what’s the differentiator for you? What are you doing that’s uniquely you? Are your products actually designed to be email first? Anytime I run into a brand they say we’re trying these emails, they don’t work and I look and I see it’s still the RSS feed. You know I think there might be an opportunity for you to something a little better and then transfer. I feel bad too when people switch to a new tool and then it doesn’t work and they go, yeah what’s wrong I thought this was going to fix all of our problems. Yeah. Yeah. Puts people in a difficult situation and certainly the employees who pushed for a change, sometimes there are good reasons to change. It’s a good reason switch ESPs but often you have to think about first the strategy and implementation before you get to that.

[00:42:02.080] – Jason
So we’re we’re getting close to time here. I want to talk about two more things before we wrap up. The first is Not a Newsletter. If people aren’t familiar with that, Not a Newlsetter is your monthly guide to all things email, so you collect jobs, you collect articles, tools, all kinds of different things. How did that start? What was the original like strategy behind that?

[00:42:27.970] – Dan
I love that you think there was a strategy. So it came out of a really interesting sort of place. I’d been having a lot of conversations with friends in the industry and folks who were starting to get into email who were saying where do I go to read really smart things about email? Where do I go to learn what other folks are doing? What’s working, what isn’t? Personal stories, resources, all that sort of stuff. And there are great resources for the general sort in the email community. I will mention that litmus has an amazing blog that is incredibly useful. But you guys really tackle things from a larger sort of perspective. Strategy and tactical perspective for folks who work in editorial spaces, the nonprofit world, who are trying to do some storytelling with email. There really wasn’t a lot there and I thought there was an opportunity to build that kind of destination to discuss email and to have a conversation around email. And it started out and it still is. It started out as a Google Doc mostly because one, I was being kind of cheap and didn’t really want to set up a website thing and what I didn’t want hosting and it was just all the extra steps.

[00:43:52.570] – Dan
I just thought what’s really, it’s the minimal viable product, what’s the least I can do to get this off the ground? I’ll open it up as a Google Doc. I had had some various Google sorts of projects before. About a year earlier, I had launched, I’d given a talk here in New York about ways to sign up people for your newsletter and then had taken the presentation, put it into a Google Sheets and shared it around on LinkedIn and other channels. And every time I would pop in there. You know even a couple months later I would see a couple, you know in the way that Google shows you some anonymous animals in the corner, that other people are reading it.

[00:44:25.120] – Dan
There were always a couple anonymous zebras in there. And I think that’s interesting. You know I put this online six months ago. There’s still a couple people reading this and I would get emails from folks they liked it. That was interesting, that stuck in my head. And so the Google Doc was OK. People seem to like the idea of the doc, it’s an easy way to share, people know it. If I’m writing a memo at my office, I put it into a Google Doc and I show it around. So there seems to be a kind of a mentality around sharing built in. Give me an easy way to publish it and a way to start. And I thought I would just go really deep into the topics every single month that were on my mind. And when I launched it I was actually on vacation with with my wife and she had a copy of the first one and I said you know I’m going to put this out there and I’ll share it on some channels that I’m active on Twitter and LinkedIn. We’ll see what happens. You know if 10 people sign up by the end of the month I’ll keep doing it. And we posted it online and I closed down all the tabs and I came back and several hundred people had signed up. And I was Oh OK. And by the end of the week of vacation I think the list was up to 400 or 500 people. That’s awesome. OK. I think, I think I hit something here and maybe a need for this. I guess I’ll keep this thing going. And it’s been fascinating to see the types of people. You know, at Litmus through something like the blog, Litmus Live, you guys are really connected to the world, people who use email, and I had not realized how many different types of people were thinking about storytelling or distributing content through email. You know ranging from, conversations I’ve handled in just the last few weeks with people, ranging from like, I run a credit union and my credit union, the main way we talk with our clients is through email, like I’m working at an airline and the way we talk with our employees, I’m in a news organization and the way you reach an audience and customers. I’m amazed at the different people who use email in very similar ways.

[00:46:31.620] – Jason
Yeah that’s awesome. It’s definitely one of my favorite resources and I look forward to the new ones. It’s kind of a double edged sword there because I love it. But then as soon as I get it then there’s like 40 extra tabs that I have to go through on Chrome.

[00:46:46.740] – Dan
you should see what it’s like when I’m putting it on.

[00:46:49.100] – Jason
I can absolutely imagine. So the other thing is you’ve just started a consulting business called Inbox Collective. And I think you have what, you said two weeks to the day at The New Yorker, is that right?

[00:47:03.010] – Dan
Yeah. Yeah. I’m leaving The New Yorker. I’ll say it has been unbelievable. Great opportunity. I have loved my time here. What really happened was that, with Inbox Collective, I launched Not a Newsletter. I started getting replies right away from people saying this is great. We are starting to invest in email. Who do we talk to to help us figure out strategy, growth, monetization, engagement. And I’ve been trying to find this person who does this for a couple months and there are people who tackle different parts and industry. But the types of questions I was getting, I wasn’t finding anyone and I thought, OK well if the person they’re looking for doesn’t exist the person should probably be me. But deciding that I actually wanted to leave The New Yorker was an incredibly tough decision because it’s been such a good place to be. I love working here and the types of stories you work on are exceptional. But there’s email, and it’s funny to say in 2019 that email is having a little bit of a moment.

[00:48:03.210] – Dan
A lot of organizations are really starting to see the power of email and there’s an opportunity for me to help. A lot of different organizations. News organizations, nonprofits, businesses, brands figure out how to get the most out of email. Building relationships, growing audiences, monetizing these audiences, and using email is a really powerful tool. There’s so many opportunities and so Inbox Collective is an attempt to actually go out and start try to work with a lot of these brands to help them get the most out of email.

[00:48:35.280] – Jason
That’s awesome and you talk about leaning into an idea. This is one where you are definitely leaning into Google Docs because if anybody goes InboxCollective.com, you’ll be presented with a Google slide deck there that goes over your goals and like your service and stuff, which I think is amazing.

[00:48:52.590] – Dan
I figured at a certain point, once once you’ve gone this far… It’s the line from Shawshank Redemption. Once you’ve gone this far maybe you’ll come a little further.

[00:49:01.440] – Jason
Yeah nice. I can’t tell you how many people I’ve shared Not a Newsletter with and then they always come back and they’re like, wait, it’s just a Google Doc, like is there an actual email? Like there is, you get that email notification, but it’s always funny to see their faces when they realize that all this stuff is just driven by Google on the back end.

[00:49:22.320] – Dan
It is. The one complaint that I have with the Google Doc is it’s not that great from mobile devices. They were never really designed to be used in this way. So I’m trying to figure out exactly what to do about that because I I do know the audience is mobile. What The New Yorker and BuzzFeed, our strategy on email was always mobile first. So it seems funny to build, for me to go against that and build a product that is not mobile first. I’m still figuring out exactly how I’m gonna tackle that. Going forward it is something I have to figure out. But yeah the other thing beyond the fact that it’s a Google Doc that I still love is, even though it is literally a Google Doc and it’s a briefing every month, I say, and it’s called Not a Newsletter. I could not have been more clear about what it is. It is not a newsletter. Had I called it, it’s a Google Doc. Yeah. Maybe that would have been more specific but I still on a daily basis get emails from readers who say I love your newsletter so much. Every single day I get one. I guess I can’t outrun it. I guess I’m gonna have to lean into it.

[00:50:28.870] – Jason
Yeah you’re stuck with email for life. That’s that’s just how it goes. Once ther, there’se no going back. So are there, outside of or maybe within Inbox Collective, are there any specific projects you’re really looking forward to in the coming year or two?

[00:50:45.330] – Dan
Yes. So a lot of what I’m doing right now as I get started is one, working with brands to try to lay out the strategy. Working on tear downs of people’s email programs. Doing a lot of coaching actually. This has been really, really fun. There are a number of companies I’ve talked to and said, we feel like we have a pretty good handle. We just want someone we can talk to once a week, once every other week to talk through strategy, to review metrics. Would you be that guy? I hadn’t really thought about it but, yeah, I love working with people and talking through challenges. That’s been really fun. The other thing that I’m working on that’s going to be, oh goodness, hopefully an end of 2019 or early 2020 kind of projects that I am still building up the structure of. But it’s been fun so far has been this email accelerator kind of program that’s going to be, it’s gonna be an opportunity for me to work with brands over the course of about three months and actually put some of the strategies that we’re talking about into play in terms of engagement and monetization, growth, and an opportunity for folks to work with me in kind of batches where it’ll be groups of a couple different similarish sorts of brands all working towards a common kind of mission but with individual sorts of challenges and trying to figure out how we can collect groups of people together to tackle lots of different things all at once.

[00:52:07.600] – Dan
I’m really excited about it. It’s not close to being ready yet but should be by the end of 2019 and folks signed up to Not a Newsletter for the briefing will get notified when that thing is ready. I’m excited about that one, that’ll be fun.

[00:52:26.350] – Jason
That’s awesome. Well, thanks Dan for joining us. So before we go where can people find you online?

[00:52:33.040] – Dan
So if you really want to find me, I mean you certainly could follow me on Twitter but I tweet once every seven weeks. Yeah but for the most part, the way you can find me is either NotaNewsletter.com or InboxCollective.com. Oh, and Jason, I’ll tell you one thing which was you mentioned Stry.us at the beginning. The lesson I learned from Stry.us was, and you asked why don’t you launch any websites where people can immediately pronounce and spell the name of it right away? When Inbox Collective came around, I thought about lots of really bad names, like really clever things, weird misspellings on the word inbox that had different letters. And then at some point I went, this is dumb. People should be able to type into a browser right away without saying it. So yeah that’s how you end up with something like Inbox Collective but you can find me at InboxCollective.com and NotaNewsletter.com. Stay in touch and hopefully those resources will be useful for lots of folks.

[00:53:33.220] – Jason
Awesome. Thanks Dan I really appreciate it. It was a great conversation and I’m not in the news world, like I obviously consume a lot of those newsletter,s so it’s always great to get the inside scoop from somebody that’s been in that industry for so long and kind of giving us the tips and tricks. So I appreciate it.

[00:53:50.500] – Dan
Amazing. Thanks for having me.

[00:53:52.090] – Jason
Thank you.