The Number One Thing Is Automation

Dan Oshinsky was the Director of Newsletters at both Buzzfeed and The New Yorker. Today he runs his own email consultancy called Inbox Collective. Dan has seen newsletters from the early days, and has been instrumental in developing the newsletter strategy for some of the largest publications around. 

In this fantastic interview, Dan shares takeaways for large newsletters and indie creators alike. He shares how his newsletter led to the Buzzfeed job, and how, once there, he discovered the building blocks that make newsletters resonate with their audience (spoiler: cats ARE involved).

Dan also warns us of the danger of obsessing over open rates (or any “silver bullet” metric), and how Job #1 for your newsletter is to earn its place in people’s inboxes.

After talking about the importance of carefully defining your newsletter’s audience, Dan answers these burning questions:

• Can I really build a business around an email newsletter?
• Is email going away?

Tune in for the answers, and so much more!

Links & Resources

• Buzzfeed Newsletters
• The New Yorker Newsletters
• The Wall Street Journal Newsletters

Dan Oshinsky’s Links

• Dan’s Website: danoshinsky.com
• LinkedIn: Dan Oshinsky
• Twitter: @danoshinsky
• Inbox Collective - Together, let’s make better newsletters.
• Sign up for Not a Newsletter

Episode Transcript

Dan: [00:00:00]
It sounds kind of corny, but you kind of have to have a mission. When you start with the newsletter you have to have, this is the thing that I’m doing for this audience.

This is why I think I can be useful and how I can be helpful. And if I do a good job, I build that loyalty. I build the audience in the long run. there’s going to be a return on that investment. 

Nathan: [00:00:24]
In this episode, I talked to Dan Oshinsky, who was the director of newsletters at Buzzfeed, and then the same job at The New Yorker. And now he runs his own email consultancy called Inbox Collective, and Dan has seen newsletters from the early days. He’s seen multiple waves of newsletters become popular.

And then of course he’s run, some of the largest publications around. So it’s a fantastic interview. He has a lot of takeaways that are good for, you know, large newsletters and indie creators alike. So I’m excited to dive in. 

All right, Dan, thanks for joining me today.

Dan: [00:01:00]
Thanks for having me.

Nathan: [00:01:01]
So let’s, let’s dive right in. You’ve got an interesting background in that we have all of these newsletter creators who. Come into it from, you know, any number of things, but, but they’re often indie creators where they’re brand new to the space, you know, or they’re growing up through one path and you’ve taken a different path of building newsletters at Buzzfeed than The New Yorker.

And now you’ve got a bit more of the indie path as you’re doing the consulting and everything else, but I’d love to just take us back to when you first started to get into running newsletters at Buzzfeed and what, what started that path?

Dan: [00:01:36]
So it actually started a little before Buzzfeed. The first newsletter that I really launched was a newsletter called Tools for Reporters. It launched in 2012 and it was.

I’ve been doing it a little while. It was Tools for Reporters is exactly what you think it was. It was a newsletter where we share tools that reporters could use.

It’s actually still going. I went to the university of Missouri journalism school and some Mizzou J school grads have picked up that mantle and run with it. And it’s all it just hit earlier this year. Something like 200 additions of this thing has been going for a long, long time. despite my efforts over the years to, to accidentally kill it with, you know, having a job and having other things to do, it turns out when you get hired at Buzzfeed and you have a thousand things to do the like side newsletter, you’re working on becomes a little less of a priority, but it’s my entire newsletter story really starts with this thing Tools for Reporters.

I was playing with lots of different types of tools. And it had stuff that I wanted to share figured a newsletter would be a good place to share it. set up a fairly basic, you know, at the time this was MailChimp. I went to MailChimp, set up a newsletter, pretty straightforward to get something off the ground.

And in a couple of, you know, first couple of weeks, I got to a place where there were a few hundred subscribers. And for me, the game changer with email was I had, I don’t know how many Twitter followers or Facebook, you know, Followers or friends I had at the time, but I had more of those than I did newsletter subscribers.

But if I put something out into the world on Facebook, or I sent out a tweet, nothing would happen, literally nothing would happen. I’d say here’s this exciting new thing I’m working on and nothing would happen. And then I would email a few hundred people and say Hey, here’s this thing I’ve been working on.

And I would get Requests from people that, you know we want you to come in and sit down with us and have coffee, job interviews, the Buzzfeed job partially came at a result of at, or out of me working on Tools for Reporters. They. You know, when I started talking with them, I shared with them my newsletter and they’re like, this is really good.

We like this. We can do more stuff like this. It was amazing to me how much more impact email had. the conversations I had out of email was really the exciting part because it wasn’t just me broadcasting, whatever news right out into the world but Putting stuff out there and then people writing back and saying I actually have some more stuff I want to talk to you about this, or I want to go deeper on that subject.

Or how do you feel about this? I really got to build relationships with my readers and that always struck me as something that was really, really powerful, that set email apart. when I got to Buzzfeed, our, our thinking was twofold. One is we were going to have a chance to build an audience and really have ownership of that audience.

of the relationship with them it wasn’t something where. Social media giant could just say one day, you know, We know you have X number of people who follow you on this channel, but, we’ve made some changes to the algorithm and you no longer have access to that audience. You know, we really have the ability to build relationships through email, which was exciting, but the other thing was the potential for conversations, the potential to ask people questions, to get their feedback and to really get to know our readers.

That was really, really exciting and something we knew there was huge potential for 

Nathan: [00:04:57]
Yeah, that’s big. And then, I mean, that’s the exact same experience that I had earlier with. Now of like, I actually expected social channels to outperform email, but peopl...