10 years of newsletter advice in 65 minutes ft. Dan Oshinsky

**Dan Oshinsky** (0:00)
There's not too many newsletters, there's too many bad newsletters. There's a lot of bad newsletters.

**SPEAKER_2** (0:04)
You launched this seven years ago this month, and you consult businesses on email strategy, growth and monetization. For me, this is the best newsletter education resource on the internet.

**Dan Oshinsky** (0:13)
No one has ever told me they love checking their email every day. Once I get into the inbox, that's not the end of the relationship. That's the start of the relationship.

**SPEAKER_2** (0:22)
What are some of the more unique, particularly tough challenges?

**Dan Oshinsky** (0:26)
There is no secret drawer of tactics. The bar has been raised for newsletter expectations.

**SPEAKER_2** (0:33)
Overrated or underrated? Subject line A, B testing. Overrated. Overrated or underrated? Open rates.

**Dan Oshinsky** (0:40)
Ooh, can I get you a controversial take?

**SPEAKER_2** (0:42)
Please do.
So let's talk about the AI inbox, present and future of this. I know that this is something that you've been on about recently. You've spoken about it at the newsletter conference, maybe elsewhere you've written about it. You're telling people that the inbox is about to change more radically in the next year, a couple of years than at any other point in the last three decades of inboxes. So what is here now? What is already radically changing? And then what do you see really coming down the pipe in the next two years?

**Dan Oshinsky** (1:14)
A lot is going to change, some of which we don't know and can't predict, which is everyone's favorite consultant answer. Oh good, there's an unknown future.

**SPEAKER_2** (1:25)
Congrats.

**Dan Oshinsky** (1:27)
Thanks Dan for coming on the podcast and telling us that we don't know what's coming. So what's here right now, we're in the early, early, early days of AI and the inbox. So the stuff right now are things that, honestly, I'm telling people not to freak out about or worried so much about. It's things like AI summaries, it's different inbox tools that might read your newsletter and rewrite the pre-header text of your newsletter, a little bit of text that goes below the subject line. It's a little stuff right now. What's coming is, one, AI making more decisions about what goes where in the inbox, helping surface the right content for you. Hey, you get a bunch of newsletters on a daily basis in your inbox, some of which you make time for, but some of which end up in weird folders you miss. But we've actually realized that there's some stuff in there you might want to see, so we're going to try to surface that. It's going to be better versions of summaries and end-of-day reports.
I open my newsletter at 5 p.m. on a Thursday, and there's a report that says, by the way, Dan, here's the things you need to deal with right now. We flag these emails as ones that you need to handle and respond to, these emails that you want to read, and we went ahead and got rid of some stuff that you didn't really need, and maybe even replied automatically to some stuff that we could just handle for you that wasn't at all that important.
There were certain basic things that we just scheduled to handle for you, no big deal. We're going to see more AI assistants and agents built into the Inbox. To me, this is a little terrifying because not the idea of AI agents, but the idea of the people who will have access to the AI agents. I think about the idea that my mother, bless her, Lisa Oshinsky, is going to have access to an AI agent who is going to make decisions about things, and I love my mom, but I'm not totally sure that she is, or I am ready for that AI future in which something learns about her and her habits and how she writes, and handle some of her replies. So all of that is coming. It's going to be unusual. It's going to be bumpy. In the short run, what I'm telling teams is like, focus on the macro, not the micro. The macro of the inbox is going to change. We're going to have, I'm less concerned about the summaries or anything like that, more about, for the first time really since the rise of mobile internet, when people stopped just checking email on their computers, they started checking email all the day on their phones, iPhone, PalmPilot, BlackBerry, all that stuff. All of a sudden, we have this new thing that's going to change our relationship with the inbox as a reader. Okay, AI can read, summarize, sort, reply to emails, and we don't know exactly what that's going to look like, but it'll change our relationship. We're probably likely to use email in a slightly different way. My hope, and this is just a guess at this point, but my hope is that if we're able to clear out a lot of the clutter that the average person really doesn't want. The average person, the marketing emails they don't want, the email from that politician that you never signed up for, but you get it anyway, and the emails from your...