AI Is the Biggest Change to Email Since the iPhone w/ Dan Oshinsky

Email has only had two truly big moments: the AOL CD in 1998, and the rise of mobile. Dan Oshinsky says the third one is happening right now — and nobody, not even the Gmail team, knows what the inbox looks like on the other side.

Dan ran newsletters at BuzzFeed and The New Yorker before founding Inbox Collective, where he helps newsrooms, nonprofits, and independent newsletters get more readers and make money. I caught his AI talk at the Newsletter Conference in May — it was the conversation everyone kept having in the hallways afterward. So I brought him on the show.

We get into who you should actually be writing for (people, robots, or deliverability), why depth is the new moat, where AI genuinely earns its keep in a newsletter operation, and the one fear keeping publishers up at night: email's stability — the entire foundation of this industry — is being challenged for the first time.

🔔 Subscribe for weekly conversations on newsletter growth, deliverability, and monetization: https://www.youtube.com/@audiencebridge

📬 Get the newsletter breakdown of every episode: https://www.audiencebridge.io/subscribe

CONNECT WITH DAN:
Inbox Collective: https://inboxcollective.com
LinkedIn: https://www.linkedin.com/in/danoshinsky/

CONNECT WITH CHRIS:
X: https://x.com/miqchris
LinkedIn: https://www.linkedin.com/in/chrismiquel
Audience Bridge: https://www.audiencebridge.io 

Transcript

Intro: who is Dan Oshinsky?

SPEAKER_00 0:00

It's tough for me to imagine a world in which email just goes away. The newsletter operators, the editors, the writers, who they're writing for. Are you writing for email of the lord ability? Are you writing for the people? Are you writing for now AI? For me, it's still writing for people.

SPEAKER_01 0:14

No, the writing for robots is really interesting.

SPEAKER_00 0:18

90% of people still don't even know what the heck to do with AI. They're not really using AI on a daily basis.

SPEAKER_01 0:23

AI is coming. Think about how you're writing and creating really good deep content for your audience. I've never met someone who says, oh man, the thing that I love most about my day is checking my inbox.

SPEAKER_00 0:33

Is there anything you can think of the newsletter ecosystem AI can't replace?

SPEAKER_01 0:39

The one thing that I hope AI doesn't take away from us in the long run is our curiosity.

SPEAKER_00 0:57

A little list flare, I guess, to have Dan Oshinsky on the pod today. Dan, how are you doing? I'm doing great. Thanks for having me. Awesome. Sure, many of you know who Dan is. Dan is the owner of Inbox Collective. He helps, I'll let him give the whole spiel, but newsletters are not even newsletters, I should say. So the email, uh growth, monetization, you know, basically helps you make your newsletter what it needs to be to grow. He worked at the New Yorker as the new head of newsletter over there. Also a BuzzFeed, the two very uh high-level operators. So he's got a lot of experience in that. And now an inbox collective. He's more of a consultant helping bringing all that knowledge he's earned over the years to businesses. You can give your little spiel there. That's probably not as great as you're gonna think.

SPEAKER_01 1:44

You did just fine. My one-liner is that I helped newsrooms, nonprofits, and independent newsletters figure out how to get more readers and make money. See? Perfect. I've had I've had eight years of practicing the one line.

SPEAKER_00 1:56

It's it's gotten pretty good at this point. So was this back in I guess May? Uh we're at the newsletter conference. I got a chance to uh hear Dan's little chat on AI and how it's expected, you know, gonna affect newsletters and how it's what it's doing now and kind of the future, what to expect, which no one really knows, which he kind of got into, but it was a very good, thought-provoking conversation. I think a lot of people were talking about it at the conference and afterwards, and I said, well, we should probably get Dan on on the show here so we can talk about it. I think uh my audience would appreciate your insights, uh, what you got to say. So that being said, we can just get right into it. And

The three big waves of email history

SPEAKER_00 2:33

I believe, you know, one of your big things like emo hasn't really changed over the years since it originated and all that stuff. And now with AI and what they're doing with the inbox summaries and whatever is gonna be the big first big, I guess, major change outside of like deliverability and algorithm changes just trying to get in the inbox, but like as far as user experience, stuff like that, that this is like the biggest thing that's happened since email. What's your thought on that?

SPEAKER_01 2:59

Uh yeah, I think there's really the kind of uh a handful of very big moments in email history, and this is maybe the the third really big one. There was the rise of email as a platform we all use, that AOL CD shows up in your mailbox in 1998, you set up an embarrassing AOL screen game and you know start using email on a regular basis. There's the rise of mobile email when Blackberry, Palm Pilot, iPhone are coming out in the early to mid-2000s, and now there's this. And those other waves have been generally pretty good for email. More people using email because of all those AOL CDs, Yahoo! email addresses, all that good stuff. Uh, the rise of mobile email meant that people became untethered from their desks. They were no longer just checking email when they were at work or at their home computer, but suddenly on the go wherever they were, checking email, responding to email. If you're in the newsletter space, that was generally a pretty good thing because your reader was much more likely to be spending more time checking that inbox every day, looking for new stuff, a lot more chances to get in front of that reader on a daily basis, or even on a potentially an hourly basis. And now there's this next wave, and it's the AI wave that's coming. And you said it a second ago. Some of these changes that are coming, we can start to see. We're starting to see things like AI summaries or people using AI agents. We'll get into all this today. But a lot of the changes that are coming, we one, don't know that what the boy we don't totally know what's coming. Two, we can't necessarily totally anticipate what's coming. And three, I think if we were sitting down with the team at Gmail, for instance, today and say, what's on the roadmap? They would say the same thing, which is we don't entirely know what this inbox is going to look like in three or five or ten years because the changes are happening so quickly. And one thing I want to emphasize up front is we know this is going to come. Like, there's AI is coming for every part of our digital lives. Email is one of those things where nobody, I mean, you've been in the space for a long time, so have I. I've never met someone who says, Oh man, the thing that I love most about my day is checking my inbox. Like, I I just so psyched to check email and that those emails from my boss and those back in the day.

SPEAKER_00 5:10

You were, because it was the first gamification when you got absolutely you got mail.

SPEAKER_01 5:14

You got mail, yeah, absolutely. That that sound, can you imagine if you had had that sound happen every time you got an email? Just ping, ping, ping. You would be all you'd hear me.

SPEAKER_00 5:23

Talking about that, it's kind of similar because we have a Shopify store and we used to have that all the time. The little cash register ring ching, ching, and you like for the first week, you're like, oh, this is amazing. And then over time, you're like, this thing just doesn't stop ringing, it's freaking annoying, so you just gotta turn it off.

SPEAKER_01 5:38

You'd start to learn some of those gamification sort of things. Good at the start, not always forever. But to my larger point, nobody gets excited about checking their email anymore because there's too much of it. A lot of the stuff you end up with in your inbox isn't stuff you want in the first place, or even remember signing up for in the first place. And AI is so good at making some of these decisions about what you want, don't want, about learning about you relatively quickly, and about streamlining a lot of processes of behind-the-scenes stuff, the unsexy, boring stuff that you do on a daily basis. AI is really good at at taking some of those repetitive tasks and saying, I can handle that. And so it only makes sense that AI in the not too distant future is gonna get good at managing your inbox and being integrated into your inbox in a way that will change the way you, the user, use your inbox on a daily basis. My hope, my real hope is that this will lead to a cleaner inbox and people say, Hey, I want to make space for the things that I like. It's gonna look a little bit more like a podcast feed, maybe. You know, hey, here are the things that I really like, I want to make time for. But there's also a universe in which people say, Hey, I don't have to check my emails much, because my AI assistant, my agent is behind the scenes working on my behalf. I need to check in, you know, once a day to handle a couple of high priority things, and otherwise I'm good. I don't need to check it 12 times a day, 50 times a day. Anyway, let's get into it. There's it's

Writing for people vs. robots vs. deliverability

SPEAKER_01 7:01

coming for us, it's coming for the inbox. We gotta figure out how to adapt.

SPEAKER_00 7:04

Cool. So let's start with let's go more of the content route. Obviously, we don't really know what's gonna happen with AI, its impact, what they're gonna serve. Obviously, they're doing summaries now. And you have all, you know, you have all these apps that you connect to your inbox provider to do all the filtering of it, which I hate. Like I turned mine off, it just it was too crazy for me. So we don't really know what what's gonna happen there. Well, we'll talk talk about some of that later, but let's get into the the content piece and and more specifically, who should the newsletter operators, the editors, the writers think about who they're writing for? Are they writing for people? It's always like the thing, especially me with the email deliberability stuff. Like, are you writing for email deliberability? Are you writing for the people? Are you writing for now AI? How are we gonna navigate that in this new AI-driven world?

SPEAKER_01 7:53

Yeah, I'm I'm still telling my clients to continue to write for the person. Write for that human who's opening their inbox, making these choices. And part of this is because, and this is an assumption, but it's it's a pretty educated guess at this point, based on 30 plus years of people using inboxes. If you're someone like me, I'm almost 40 years old. Email has been part of my life since I was in elementary school, essentially. And there's never been a part of, aside from uh the you know, third grade and earlier, never really been a part of my life where email wasn't involved in some way. And of course, since college, graduation, everything that email is very deeply integrated into what I do on a daily basis. A lot of people like me out there who use email, who they're in the habit of using email, it's part of how they communicate with their colleagues, their friends, their family. It's tough for me to imagine a world in which email just goes away. As much as I think there would be some people who would love for it to just disappear, I don't want the hassle of it. It is still a really valuable communications tool, something that we all use. And it's it's really tough for me to say, hey, there's gonna be a universe in five years in which people no longer check email. Maybe they'll check it a little bit less, but I still think they're gonna be using email on a daily basis. It's just so integrated into our lives, and in particular, our work lives. So for me, writing for a human is still top of mind because as I try to think about what's gonna stand out in that inbox. Hopefully, it's gonna be a less, less cluttered inbox if my AI agent is clearing out the stuff that I don't want anymore. The stuff that I'm gonna make time for is gonna be really good stuff that's voicey, it comes from a person, it has expertise, it has perspective. It's gonna be stuff the way I'm thinking about it is depth, depth of knowledge, depth of insight, depth of access, depth of analysis. The people who are bringing me really, really deep looks at whatever I care about, whether that's local news in my community, whether that's a topic that I work on, uh, whether it's something that I'm passionate about as a hobby. The people who bring me that kind of depth are gonna be the ones I think that stand out and win. So I'm still trying to write for that person because I made the show cure before we started the call, but I'm not gonna break my own rule. I said, we asked, you know, you asked, hey, is there a topic you want to talk about? I said, just don't make me talk about the Washington Nationals right now. The bullpen is annoying me too much. But I'm gonna talk about the nationals for a second because as a nationals fan, and you know, I care about the team. I have various text threads of family members and friends. And one of the things that's missing actually out there, there's a couple reporters who cover the maths. But if there was a really, really good like weekly newsletter on the maths that just broke down stats and trends and the farm system, what's going on behind the scenes, I would always make time for that because it goes really deep on a topic that I care about. I spend time during the week every week, you know, paying attention to what's going on with the team. And and so that deck

Why nobody outsources what they care about

SPEAKER_01 10:40

is gonna win out. Am I going to outsource my Washington Nationals fandom to my AI agent and say, just send me a couple of stats on what James Wood did this week and, you know, add at the plate or whatever. I'm not gonna do that because I care about the sort of thing. And the same thing is true for what happens in my community, local news, a thing that I'm I'm not necessarily gonna outsource. I really want to know what's happening in, you know, my neighborhood, my part of the world. I'm out here in Utah right now, there's a bunch of fires happening. You know, I I don't want an AI, I don't want to I don't want an easy telling me, oh, hey, Danny, here's what's going on with these fires. I want to go really deep and figure out what's happening. You know, what do I need to be prepared for? How worried should I be, all that kind of stuff, because it affects me on a day-to-day basis. And so for me, it's still writing for people. Now, the writing for robots is really interesting. I'm still trying to wrap my head around exactly what that's going to look like. And I think some of it's gonna depend on what kind of tools end up getting plugged into your inbox in the long run and what we end up using. Is it a, you know, a chat GPT, a clod, a perplexity, something like that, a Gemini, where we say, hey, there's a universe in which it makes sense for, you know, Gemini to put together a quick hits look of the handful of things that I really care about today. And what I actually be sending is two versions of my newsletter, one that's really written for the robot, that here are the five things that Dan needs to know right now. It Gemini goes and pulls it and puts it into a summary for me. There's a world in which that would make a lot of sense. But I'm also thinking about okay, as the reader, I'm gonna want to go really deep on certain topics. And that's not gonna be produced through a quick summary or through something that, you know, claw I can spit out for me with a I throw it question. I'm gonna want to sit and spend some time with some of these topics. And so to me, that still requires writing for a person.

SPEAKER_00 12:20

Have you been thinking about, you know, coming up with at least your own thought process strategy? I wouldn't say algorithm or something, but like what how you can integrate some sort of knowing knowing that there's gonna be a lot of inbox summaries and all this stuff happening, you might not even have to open emails and stuff to like see what's going on to kind of lift up that call to action that's gonna get them to want to come in to to read the actual newsletter. I mean, I I I I agree, I think that I mean, look, this is this is probably the next step of when they just came out more than uh it's probably three years now, when they came out with the new book set of requirements, and all stuff was released within Google, Yahoo, and then Microsoft within the last year adopted it, killed the inbox for a ton of people and all this stuff, which is great. I said it doesn't uh fill everyone no worries. It's gonna be better inboxing for you and all the the garbage and stuff, it's gonna be harder for them. And to me, I see this as the next evolution of that too, because now you have AI. So, like people are gonna really they're still gonna want the stuff, like you said. They're gonna want their their niche stuff that they're interested in, the voices that they want to hear. Uh, and all the they can just get rid of all the other stuff. So I think yes, the top operators, the top voices, the top stuff have nothing to worry about. Email is always gonna be around, it can't not be around. I mean, you need to, I mean, it's not gonna be social media. Um, social media, you can be a fan, you can like certain things, and you still won't see their stuff. At least if you're if you sign up for an email, you can whitelist it, you know, whatever. Make sure you get it. So I don't think that's ever gonna go away, and then all the transaction stuff's gotta be tied to something. And let's say put some you know, QR chips or something in our bodies and we just start use speech.

SPEAKER_01 13:59

Help us, please help us. I I hope not. So I kind of lost my train of thought there, but what what I'll throw out to you is as kind of an analogy, the physical mailbox, the one that you have at the end of your driveway, or you know, your apartment building, you go downstairs in the lobby, wherever you go to get your mail, you go to the PO box at the post office, is a good analogy for this, in that over the last two to three decades, our reliance on physical mail as a thing that we use for communication has gone down and down. I still, um my wife and I are still birthday card senders. We have our little list of friends and family, and you know, we sell still and send birthday cards to people and send postcards when I'm on you know on vacation somewhere to various friends. But I also think about the handful of magazines and publications that I get in print. And it's not a huge list anymore. It's a small list, but it's places like the New Yorker and the Atlantic and New York Mag, and uh, I will confess this uh secretly an old man, a young old man. Uh we get all the AARP publications, and I just love them. AARP magazine is the greatest. It's it's it's I genuinely love it. It's a delight every time for a variety of reasons. But it it it's those sorts of things they show up. I actually make time for those. And I go down to the end of the street, I go down to our mailbox, and I get

The mailbox at the end of the driveway

SPEAKER_01 15:13

those sorts of things. And so to me, yes, I I look at the mailbox now, and there is still plenty of clutter that gets through. There's still plenty of junk mailings and you know, the catalogs for stuff that you don't really want. We still get some of that, and that goes straight in the trash. And like the analogy here is the inboxes are gonna get better at identifying that stuff and just going like these marketing messages that you never engage with, gone. We're just not even gonna show them to you, you're not gonna see them anymore. Gmail, Microsoft, Yahoo have done a good job over the last couple decades of getting better, better filtering goes out, but stuff still gets through. Hey, you know, Chris, you never open these. They're gone. We're not gonna bother them, we're bother with them. We're gonna give you a chance to prove to us you want to engage with these, but if you don't, we're gonna let them go. And then what you're gonna be left with is that really good stuff where you're like, oh, it's that magazine that I look forward to, or it's the birthday card in the mail, or a postcard from a friend, like, oh, yeah, I want to make time for that. So I get excited about that version of the inbox where it might be a little less cluttered and the stuff that comes through feels a little bit more relevant to me, which is really exciting. I do get excited about the idea of my inbox and some of these AI tools helping me, you know, sort through some of those things, and maybe finding stuff that I might otherwise miss and you know not seeing in my inbox right now, because like I get so many things. As someone who works in the space, I'm sure you do too. I subscribe to a billion newsletters, so I often do miss things, and there is a world in which those AI tools might actually be able to help find things for me that I'm not seeing because things are going into all these folders, and I'm I'm trying to manually like you know sort the clutter and you know, kind of weed through everything to find the stuff that I really want. I do think there's a pretty good future for the inbox on the other side of this. But I also think one of the pieces of advice I've been giving to my clients these days is like, think about the macro, not the micro. So the the macro being AI is coming, think about how you're writing and creating really good deep content for your audience. Really think about the behind-the-scenes stuff that you need to be doing, like email authentication, or I've been telling a lot of my clients, like, if you haven't purchased like a verified mark certificate or common mark certificate in the check mark in the inbox, like this is a good time to do that sort of thing. Like anything that you can do to stand out in the inbox, anything that might send a signal to the various inboxes that you are reputable and worth being in that that good part of the inbox, you should be doing thinking about building out your brand, thinking about all of your automations and how you use those to trigger really relevant messages the right time, like do that big picture stuff. But also don't get caught up too much in the micro of the like, well, I saw this thing that you know, Gmail was starting to you know, go through an email, summarize it, and replace the pre-header packs with their own summary. How do I optimize for that? Because what I've seen over the years is these inboxes roll out lots of different tests and features, and some of them stick, and many of them do not. If we were having this conversation 10 years ago, we would have been talking about all the different Gmail tabbed inbox features, and there were lots they tried, some of which is still around today, and many of those features did not stick, it just didn't resonate with audiences, and they dropped them. And so I don't want teams to get too caught up trying to optimize for every new press release or tweet that you see, or you see one of us post something on LinkedIn, oh, there's a there's a new thing happening, you should check it out. Because then teams freak out, they they panic, they spend all this time trying to optimize for

Macro, not micro: the fundamentals that matter

SPEAKER_01 18:32

something, and it may not stick. And so think about the big picture of AI's coming. How do we build great products? How do we maintain relevance? How do we build loyalty? But not too much of, oh boy, how do I build for this really specific new feature? Because it may not be around in a year or two.

SPEAKER_00 18:49

Yeah, I think the um, you know, I think the MB the AI, uh, I mean, you gotta remember, AI is still in its mainstream and you know, beginnings. There's uh in the infancy of it, because I mean, yes, we're in the in the space, we're in the market, we're in Twitter, LinkedIn, wherever we're at. And it's a big rave there. Everyone's talking about it, like the whole world is like so engulfed in AI. 90% of people still don't even know what the heck to do with AI. They're not really using AI on their daily basis, you know, versus like going to Google and ask questions, they see the AI summaries there, they might be asking Chat GPT, but they're not implemented at certain levels. So as far as like the I think it's gonna be beneficial because I still think most people see their inbox, specifically with Gmail. Like, you have the inbox, you know, your promos, you have BAM, you have, you know, they do have newsletter stuff, and they're in a few different folders, but like people still don't, I don't think they've really fully adopted the full folder structure, tab structure. Just think that inbox is where all my stuff is. That as AI goes, and it's like now they're starting to implement all these AI apps and tools and they're categorizing stuff. Once they start categorizing stuff, now they'll be using those tabs more often. Yeah. So, like my newsletters, if I can put all my newsletters in one tab and I know they're all there and I can just see them and I don't have to worry about them. I can just go there and I listen to all this like transactional junk

The AI adoption gap nobody talks about

SPEAKER_00 20:07

and notifications and stuff I don't care about that's in my inbox. You know, I think that'll be get you know more adopted over time and it's gonna be a lot easier. And then you'll actually see an improvement and and your engagement as a newsletter provider.

SPEAKER_01 20:19

Yeah, and you're right, there's this window of time that we're in right now between your most tech savvy friend uses AI and how they use it, and you know, how I think about my mom, the idea that like there's gonna be a day when Elise Oshinsky, bless her, has access to an AI agent, and there's a gap right now between those things. Big gap. And so I think sometimes we get caught up panicking about you know that that that top, let's say 3% of users and how they're using it all these cool ways they're using AI. And then the other, you know, there's that, and then there's that next wave of people who are using it in a you know, some ways it's part of their you know daily or weekly life. And then there's the 90% of people who are just out there, and they are only vaguely aware of what these tools are or how they can be used, and widespread adoption is not there yet, and it's certainly not integrated into our daily tools like email yet, in the way that it will be in three to five years.

SPEAKER_00 21:20

Right. And and also you gotta look at it in a in a in a B2C point of view or a V2B point of view, you know, a regular consumer who's just using it as their personal email, they're not probably using AI as much as someone's using it for work. They're organizing all their stuff, they're doing all this stuff, so it's a totally different experience. So I think the consumer side of things still, you know, they're their their adoption's way less. So they're gonna stick around. Whatever's been working for years now will continue to work. I think a lot longer than than the B2B side of a newsletter marketing, email marketing in general for B2B. When you're doing your content, I know your your your big uh what's the word? You like to write it. You don't want AI writing your your content. Yep. Uh truest. Truest. Sure. Truest. What do you use AI for? I know research is a lot, but if you can share, like, what do you what what what's on your like, you've got to use it for this because it's going to make a huge difference. But you need to keep it off of here because of your, you know, authenticity or voice or whatever you want that you're still not comfortable with AI taking over. Yeah. Um, well, what what are you doing there?

SPEAKER_01 22:29

For me, it's a couple things. Uh, a lot of it is on process. So AI for the behind-the-scenes processes, the repetitive stuff that I I do on a regular basis. So I'll give you an example. Uh a client of mine started with them a couple months ago. I was asking them about a big newsroom out here in the West and local newsroom. How do you guys you do your reporting? How do you share data with the team? They walked me through the process, and it was a very involved set of download these CSVs, and then we're going to these spreadsheets and this, and it was just the number of steps. And I just said, look, this is a really good use case for AI because we can upload a lot of the raw data. We can go to a tool like Claude, walk it through the processes you've already built. We do these things in these steps, these are these spreadsheets we're using. Here's how we've set it all up. What I want to be able to do is upload this one CSV and then say, once I do this, it triggers these next 10 steps. I want you to take this data, break it down to these ways, spit it out in these ways, want you to turn it into this PDF that I'm going to share with my colleagues, turn it into some different dashboards and charts, XYZ, these sorts of things. And so those sorts of processes where they were saying, you know, we're spending five or six hours a month really manually sorting through this data, have been for years. Got that down to a point where we taught Claude how to do this, built uh a thing that runs on their machines, they upload the CSVs, and in a matter of seconds, it spits out the thing that they were looking for. And actually, now, because the data is easier to slice and dice, they're able to build an app able to build these cool dashboards and they can do more actually with their data than they had before. But it starts from okay, we have these processes, these things we do all the time that are super time consuming. It's repetitive. A machine can learn this. Let's teach AI to sort through these sorts of things. And because the data is anonymized, like I tell teams, like I never want teams at this point to be uploading lists of email addresses, for instance, to claw. I'm telling them, like, I don't want you to do that for now. It's gonna violate a lot of your privacy policies. It's conversations with your lawyers that you don't want to have. But the raw data of like, these were the 150 newsletters we sent out these months this month, open rates, click rates, various

What Dan actually uses AI for

SPEAKER_01 24:43

things, great, we can pull a lot of that data in. Or, you know, we can pull in some of the data in terms of you know click behavior of these newsletters, sort through it and figure out, you know, what are the trends in terms of what people click on? Help me figure out topics that are kind of undervalued that we might want to identify more of. Email is great for the process stuff, it's also great for a lot of the analysis and helping you identify. Look, what am I missing? I'm looking at this data every day. What am I missing that's obvious? Like, what's the thing out there where a smart observer, in this case, you know, uh your AI assistant can go, Dan, look, you should be doing more of these sorts of topics, more of these sorts of stories. This is what resonates with people. Do less of this, more of this. It's great for the analysis piece. It's also really great as a brainstorming tool as well. You know, right now I'm working on a couple ideas for some different workshops that I want to run in 2027. And so to be able to have a kind of a brainstorming partner where I can go and dump a lot of these ideas in and say, all right, here's what I'm thinking about. I want you to put yourself in the shoes of this kind of ideal customer. What am I missing? Be critical, tell me what else I might need to identify, help me try to get this to a better version so that way I can kind of work through that and get to a version of a pitch that I can take out to other friends or other places and go, here's what I'm working on. And it's been road tested a little bit. Like there's there's it's gotten a little bit of a critical eye. So for me, it's process, it's brainstorming, it's analytics, those sorts of things. It's really, really great for. I'm not using it a ton yet in terms of creativity, in terms of doing things like writing. I've played around with different versions of this to try to help me write LinkedIn posts and those sorts of things. Although to be perfectly honest, usually the perfect LinkedIn post is one that I spend about 35 seconds writing. I write in one go, look through it to make sure it's not an obvious typo and hit send on. Like, and the stuff that I spend all this, you know, I worked with, I spent a bunch of time in this. Oh, I'm gonna work with, you know, my AI tool, work with Claude to really learn my voice and how I write and come up with these really great posts. Like, nothing happens on those. And then I toss out this casual thing with like a you know a hot take or something in 20 seconds, and like that's the thing that gets engagement. So at some point I just went like, why am I bothering trying to to do to use AI in this way? When I would just like come up with an idea, you know, I write it down on my little like yellow legal notepad or whatever, but like when I get back to my desk, I'm gonna spit out the the quick LinkedIn post, and there it goes, and that's the one that takes me.

SPEAKER_00 27:14

You need to do a better job training your AI Oshinski.

SPEAKER_01 27:17

I maybe I maybe I do. Maybe I need to teach it how to write shorter, more like I don't know. But anyway, the point is those the things that I've been using it for. It's a lot of behind-the-scenes stuff, and then there's the stuff that I use, you know, various AI-powered tools. So, like I've been used for a couple of years now, I think. Like granola, I really, really love so I send a lot of calls, it takes my notes. Uh, I use WhisperFlow for a lot of transcription stuff that's super fast, you know, just the spitting out a quick thing, that's great. I've been loving this tool called Tela T L A, kind of like an alternative loom that I do a lot of screen recording stuff for clients. Clients that be like, hey, can you help me? I can't figure out this thing. Can we get on a call? And I go, actually, I actually have access to your account. I can pop in, record a video, show you in 45 seconds where to go. And it's been great because for some of those longer videos, I can record like a 10-minute video, and then I go like cut out the the likes and the ums and the pauses, uh, zoom in and follow my mouse around, those sorts of things. And I've gotten to a point where I can record a 10-minute video, I spend a minute or two, you know, editing it, and then it goes out the door. Whereas two or three years ago, those were like, I gotta upload it, I gotta, you know, this might go into like a final cut type of place, editing, making sure it looks really polished. And it's so much better than it was for stuff, you know, if it's gonna be behind the scenes, none of my clients are paying me for professionally edited videos. Like, they don't care about you know, it it needs to look at it doesn't we're not talking about a thing that needs to win an Oscar here, like it needs to help them figure out how to do X and save me from doing other call.

SPEAKER_00 28:59

So that's the thing that I'm using it for. I'm curious what you're using it for right now. Even this, even this podcast freaking uh riverside that we're on right now goes amazing because then you can just you do that, boom, it'll it'll cut out all the the stops, the pauses, the the ums, like you were saying, it'll give you snapshots of like different takes. Yep.

SPEAKER_01 29:20

So Chris, what what are you using? I mean, in terms of AI still what what's on your list?

SPEAKER_00 29:24

So what when you're talking about, so this is interesting, when you're talking about your client and and getting those spreadsheets and all the information and trying to upload it so they have the data and stuff. You did mention, and this is what's something I've been using it a lot for lately, especially with my clients, you can still provide like all the date, all the all the data uh in a secure way, you know, just provide I'm talking about the raw data of all the all the activity and everything, just with a unique identifier, you know, it could be a contact ID

The 35-second LinkedIn post problem

SPEAKER_00 29:53

from the system, it'll give you whatever it is, doesn't have to be the email, so you don't have to worry about the email kind of floating around there. But what I've been doing a lot lately in this past month or two, especially, uh I just did a post about it, I think yesterday, day before, and I think my newsletter tomorrow is gonna talk about it. Is I've really been analyzing everyone's basically onboarding, longevity, their LTV of their of their subscribers, what the activation windows are, what the opener bloat is. Uh, when I say opener bloat, it's like these these people that always open, they never click or do anything. A lot of times it's bots or security scans or pre-fetch images, whatever it is, and just analyzing it all and seeing where that fall-off is. So I just basically we export all the data, all the activity from all the emails I get sent out. We export all the profiles, and usually the profiles will have, you know, sign up date, first open date, first click date, last click date, last open date, like all this information. I'm able to suck it into uh my AI that's already, you know, modeled and stuff to analyze this stuff. And it gives me a breakdown of the median of when people are falling off. It'll do it by source of traffic, and we've been able to develop better sunsetting rules for when people should fall off, when but when back segmentation processes for the best time to win someone back, when it's not worth it. We've been doing a lot of that analysis off of it, which has been a game changer. And we've been able to cut, I mean, just the opener bloat in general. And it's always a scary thing for people like, oh, you're gonna cut all my engaged openers and stuff. Uh the the truth of the matter is, is if they're opening and they're not real opens, it doesn't matter one because Gmail knows if it's real open. You you don't, they know. They know if they opened it themselves as as a test or

Opener bloat and the 2-Minute Rule

SPEAKER_00 31:40

person opened it. Same with all the other inbox providers, and that's not really uh a signal you can rely on too heavily. Clicks, especially in Gmail, are are more uh reliable. Uh I know people, I forgot who was it, uh, who'd I hear talking about it? The Adam at work week, maybe a study like, oh, like 90% of the clicks are bots. I don't I don't believe in that, not the numbers I've seen, but that I mean they are B2B just because everything's on in in their B2 in their B2B world. Yeah, you're an Outlook, big corporations are scanning. So yeah, those are all clicks. But if you're if most of your lists, uh top-level domains, Gmail, Yahoo, things like that, then click is usually a click. I mean, I've I've gone across different platforms and checked it out, like what they consider a real click is versus a just a click, pretty close. I have plenty of clients with custom uh setups, paw uh Matt Paulson and Market Beat. Um we can pull that stuff and we'll do like analysis on on how many the click activity, but like we've set up click windows where like if someone doesn't click with if someone clicks within the first five minutes, we don't count it as a real click. You know, we we kind of exclude those along with you know any other activity, just knowing that there's no way someone always clicks within five minutes of email delivery to them. You might lose some, but over time they're gonna click again at some point in time. There's no way someone's always clicking. I believe in the two-minute rule, which was when I originally talked about it. Um, so any any activity within two first two minutes, I kind of like don't even count as a real real activity. Matt got a little crazier to to go even tighter. He went five minutes. Um, but we we analyzed all the data. So we're doing a lot of data analysis on the actual user activity, subscriber activity to try to determine what what we should do for our sending segments, what we should do for our Wimback segments, sunsetting people, and things like that. So that's been the biggest thing uh that we're using AI for. I use it for for obviously development. Uh we all all of our coding and everything we're doing through through AI. And then content-wise, I use it for my content, not to create my content, not to create my ideas, not to create my strategies. I feed it what I want, I tell it my story, I tell it whatever. I'm just not a good writer, never have been. Never, you know, I was like a D plus freaking English person my whole life. So for me, it's great. I give it something that it's not gonna get anywhere else because it's my it's my experiences, it's my my stories, it's my my knowledge that I know, and then it'll clean it up so it polishes it up some of things that I don't have. But people read it and and they still think that it's it's unique, it's it it hits all the points, they they everyone loves it. So uh I couldn't do that without it. It would take me like five hours to write a freaking newsletter.

SPEAKER_01 34:28

Well, and I think this is a good example of for me, uh I love writing as a kid. I went to journalism school with because I loved writing and loved reporting, love digging in and stuff. I just finished today uh editing a piece for the Inbox Collective website that we'll run in a couple weeks. And you know, I I I spent a couple hours over the course of a few days with this story, editing it and working with it and getting it into shape. And it's the kind of thing that I know there are plenty of people, and you are probably one who would look at this and just be like, I cannot imagine spending this amount of time like editing somebody else's story in this way, spending time through like, why would you do that? And I was the third game, I'd love doing this sort of thing. I get a lot of satisfaction out of it. So am I gonna outsource to AI a thing that I genuinely enjoy doing? No, like I like doing this sort of stuff. But then there's all the behind-the-scenes stuff that is, I'm not gonna say grueling, but is time intensive and that I don't get a lot of satisfaction out of. And coding is a good example of this. Well, I worked with some of my clients and we've built little tools and resources. Oh, hey, there's a section in your newsletter where every day, for instance, I have a client every day in their newsletter, they highlight certain stock market uh ticker, uh, you know, things. All right, some of these stocks and these market indexes. Here's how they did yesterday. It goes to the top of their newsletter. And they had somebody for a while who was manually pulling this, like going in every day, looking up what the Dow Jones and these handful stocks did. It's like, we can do a better job of this, and built them, used AI, used Claude, built a version of this tool that spits out this top section. You push a button, it spits out, you know, it uses we used um some different APIs to pull in the feeds, these are the tickers, how they all did, the green arrows go up, down, format it the way you want, yada yada. Anyway, it was a thing where it was like, hey, this is a thing that's super manual that you hate doing, but you have to have the newsletter every day. Good news, we can now do this with a click. It's a click, copies the thing, and puts it at the newsletter, and working to try to figure out how we can streamline it even further so it just pulls it automatically, you don't have to click the button and copy the HTML over and paste it in. That's an extra eight seconds, but like we're gonna figure that part out too with their ESP. Anyway, I like you find the stuff that you actually like doing, and you keep those, and the stuff that you don't enjoy doing, you think is repetitive or time consuming that you can outsource to AI. Yeah. I think it's there's absolutely cases where it makes sense to do that. And you were right, by the way, like I have not gone as far down the rabbit hole of trying to train AI to talk the way that I talk to think the way that I think. And I do think there's a world in which it would make sense for me to go and spend even more time with some of these tools and really get it inside my head, because it might spit out better versions of social media copy or help me write intros or marketing emails or stuff that you're talking about, like you

Using AI for your voice (without losing it)

SPEAKER_01 37:30

know, win back emails. All right, these are things that I you know, I think having the voice matters, but I also think there's cases where you say, if your email program is big enough and complex enough, hey, there's there's only so much time today. We could use AI to help get the first version of this out into the world, get it out to various readers and segments, see what works and what doesn't, then try to optimize it, improve it, and add our voice and personality, layer those things on, but let's use it to to supercharge what we're trying to do. And I think that's a great use of AI.

SPEAKER_00 38:01

And the biggest project we're using it for is basically it's it's my AI clone, Chris AI clone. I basically continuously feed it all my information, all my strategies, all the stuff I write, all the stuff that we've we've tested and implemented, my voice. I have it interview me every week, and we keep on going and going through it because that piece and the app that we're building, it's gonna be a big part of the deliverability aspect of it. So people are gonna be able to like, I mean, it's gonna be giving you notifications, alerts, what to do when everything's happening, but it's all gonna be coming from me, not me, because I can't be there for 10,000 people using it, but it's all my best practices and things based on it using my uh my knowledge and then my voice to help people out where I can help a lot more people doing it that way than if it was one-on-one consulting, right? I mean, it's it's it's it's unscalable. Like, I mean, I think I have like too many right now to deal with, to account for, so you can't really keep on adding anymore. So this is gonna help more people because that'll be also way more affordable for more people. Of course. Um, but they need to, and I and I've been on this journey the last like specifically the last like two, three years, especially in the newsletter space with the whole deliverability aspect. Because no, I mean, no one talks about deliverability in newsletters or in the newsletter space too often. It's like an unsexy guy, you know.

SPEAKER_01 39:18

Well, they do when things go wrong. When something goes wrong, you get these pings, and so do I. Oh my goodness, a thing is wrong, it's broken. I need help now. But other than that, it's just a thing that you know it's behind the scenes. It's like it's magic, whatever.

SPEAKER_00 39:36

Any of the conferences I've been to, then no one talks about it. It's always about list growth, it's always about monetization, it's all you have content, which I'll break. Those are the sexy things, but like problem is, is and I've plenty of people have come to me, it's not a problem till it's a problem. And when it's a problem, it's already too late because you have a business. So you go from, you know, maybe you know, you finally went on your own. Oh, you maybe you're doing 10k a month or something, you know. You're like, oh my god, and then overnight you can't deliver, you can't do anything, half the people reaching you, you can't get your advertisers anymore. Now you you know you're down to 3,000 a month. Like, what do you do? Uh so that's what I've been trying to, with all the stuff I've been sharing and my newsletter and implementing, is trying to just educate them on like the best practices to be there. So when you get there, you're not, you know, you're not gonna get your knees cut out from under you. Um, you'll have a good base. I mean, things are always gonna happen, obviously. The more you scale, the more you grow, you're gonna have complications and it gets more advanced, and things you have to have more strategies put in place and and things, but at least so I can get most of people to that part where it is a big deal, then you know, that's been my goal.

SPEAKER_01 40:40

Well, deliverability to me is like it's like plumbing in a house. You don't really think about it until something breaks, and so the thing that people get excited about, you know, you you you buy a house, we want the occasion to look this way, and we're we're painting these colors and adding these elements and the furniture, all the fun stuff. But if the pipes don't work, you got a problem in your house, and suddenly everyone wants to know where's a plumber. And so I love the idea, by the way, of using AI in that way because it's just an extra set of eyes. It doesn't sleep, it's always watching, and it can say, hey, there's something over here you need to put some attention on. Or there's uh, you know, some opportunities over here when we were talking around you know, things like you know, win back emails or abandoned card emails or some of these automations. Hey, there's a segment over here that we could target, there's a thing that we could do for them right now. Using it as an extra member of the team to help you move faster to go further, I think is really exciting. And I don't think I I for me coming from I think the journalism space, when I talk to a lot of media organizations, there's hesitancy around AI because the thing that that a lot of these reporters and marketers think about first is AI is going to take over my writing and I don't want to lose my

Chris's AI clone project

SPEAKER_01 41:55

job because my job is doing the writing. It's like actually, I want you to think about it as a competitor. I want you to think about it as a partner. What does it look like if you had AI to bounce some ideas off of to make that marketing email better, or to identify new segments, or to help you do some analysis to go, hey, there's an opportunity over here. Let's dig into that. So to use it in that way, as opposed to saying, no, no, no, I'm never gonna let chat GPT write my emails. Like that's to be honest, the the most basic of use cases for AI. Like, but I don't think it's necessarily the most exciting or most practical for you. You gotta figure out how to take these tools and make them work with you and for you as opposed to competing against you.

SPEAKER_00 42:35

Right. I mean, the AI is look, AI is great at writing the stuff, but it's it's not great at the initial strategy or what angle to go after. Like, you have to tell it what you want, and that's still gonna be your the unique angle that you provide in the story, or it's just gonna be a canned story that you're gonna see anywhere else. You can give it your angle or identify something that no one else is doing, that's what's gonna stand out in the crowd. Yep, I think that's right. I have this another good zinger, and I can't remember what it's about.

SPEAKER_01 43:04

This is see, you know what the good news is? The good news is you'll remember it later or later, you'll record yourself, and then you'll clone me la here. We'll just do it right now. I'm gonna I'm gonna laugh. Ha ha ha ha. Great one, Chris. You'll just plug it in right there, and and you've already got me. You'll copy that in. Riverside's

Deliverability: it's not a problem until it's a problem

SPEAKER_01 43:22

gonna take all of this, plug me with you.

SPEAKER_00 43:25

Thank you for that. That breaking up my brain space. So talk about so this is where AI I think is gonna be amazing. And I just had a conversation before this call. Let me just write this down so I don't forget, about using AI, but you being being more timely, relevant, and and win back scenarios. So a lot of people are doing their win back and their, you know, their reactivation kind of strategies with emails. A lot of them are like evergreen, like generic, can, same. They set it, they forget it, let it run for months. Usually it doesn't do much, maybe just a little bit, but with AI, it depends. Depending on, and it could be for any niche, it it notes going on. If you have a train and you keep it relevant within, especially in the news space, and you know enough about subscribe or whatever, when you're sending these these win backs and they can each one be customized to that person with whatever it knows about that person or what stuff they've read in the in the past that might be able to hook them back versus generic, oh, did you know whatever story you're you're missing stuff like this, but they can you can be specific to that. Yeah, that's gonna have a lot more engagement and a lot more reactivation than than these canned hybridgreen ones.

SPEAKER_01 44:35

Yeah, I love that. I'd also think just to add on to that, you know, if someone's listening to this conversation, I think something that that gives me pause sometimes when I see people talking on you know LinkedIn, for instance, about the power users or how they're using AI, it can feel really intimidating. And the goal is not to go from wherever you are today to the top 1% of AI power users. The goal is to figure out how do I add on a little bit more. And maybe that little bit more is there's a repetitive process that I have. And I want to try to figure out how to use one of these tools to streamline it. Or I want

"Deliverability is like plumbing in a house"

SPEAKER_01 45:08

to find, you know, for me, for instance, I have these client calls, I take notes, they get uploaded into a doc for the client. It was a lot. And when I started using granola for my note taking, I found I was able to actually be a lot more present during the calls because I wasn't always just trying to jot down the notes and then spending all this time afterwards transcribing. I would write down in these little these I had these notebooks and they they were full with all of these notes from all of these clients, and I'd jot them down in my incomprehensible scribble. Then I have to spend time at the end of the day, copying over the scribble into a Google Doc. And so finding little things like that where it's like, this is a tool that I can use that listens in, helps me kind of identify some of the big stuff, um, streamlines that process and allows me to be a little bit more present on my calls that I'll deal with clients. Awesome. That's a great little thing. And then when you have those little unlocks, oh, this could be used in this way. How else can I use this to refine my note-taking process or my documentation process or what you were saying around? I love that idea of let me have AI interview me every week and learn a little bit more about me and ask me questions, and then that goes and helps feed the machine so that way you can get better and better at being in Chris AI. That's so fun because it just you start to, once you start to go through these doors, I think what you see is, hey, there's a little bit more that this can do. I hadn't thought about this, but here's a way that I could use AI AI that's fun. I was talking with uh somebody the other day who does similar sort of space to us and was saying, you know, one of the ways he uses AI is for prep when he's doing talks at conferences. Because he's like, I'm giving this talk, and here's my notes, and here's the presentation. I'm trying to figure out what they are gonna ask me afterwards because I want to practice some of my answers. I want to be ready so that way I have that five minutes for QA. And I want it to be really good. I don't want my presentation to be 50 minutes and be awesome, and then the QA to be out there and be like, I don't know. That's a good question. I hadn't really thought about that one. It's like that's the last impression of me they have is is the QA part. And then they leave going like he couldn't even answer this basic thing. It's like, so I'm using AI to interview me to try to really hone my answers and find that's such a cool use of AI. I'd never thought about that. But you start to identify these little things, and then you go, well, what else is there? What else is there? What else could it do for me? How else could it help me get smarter and better and faster? And so that's what I get really excited about. And I hope people see these as so much of this is going to be incremental. It's not AI novice to AI super genius. It's I use it in this way and I liked it and I thought it was really powerful. What else? How can I do a little bit more with it?

SPEAKER_00 47:45

Let's uh let's kind of shift gears

AI-personalized win-back emails

SPEAKER_00 47:48

and talk about monetization. Sure. Where wherever you think or what's the impact AI has had on monetization, or what are you using AI possibly for when you're discussing with your clients or anything else about you know the monetization uh monetization aspect of things, or is it still too early or you're not really using it for monetization at all?

SPEAKER_01 48:07

It's really early. There's stuff that I'm excited about potentially, but I'm not yet implementing. So those things include some of some stuff you actually mentioned already. So stuff that's already in the works of various clients, how do we use AI to identify different points in the funnel where we might want to convert or retain a supporter, a subscriber, customer. So starting to use it to identify segments, targets, messaging, setting up some of these automations, lots of possibilities there. And some teams are in the early stages of trying to use it for various things there. That's exciting. Uh, stuff that I'm excited about potentially is this was a big one at the newsletter conference this year. Andy from USIS talked about what they do after someone becomes a reader. So someone subscribes their newsletter, they put them through a survey to ask some questions, and then they go into a welcome series. So I've been referring to this kind of this thing from newsletter sign up page, survey, more data collection, welcome series as the larger welcome flow. So we used to just think about a welcome series. You sign up, you get five emails from me. The exciting stuff is gonna be all right, how do we use AI to try to optimize these? So you sign up, we ask you a couple questions. AI may then say great based on these answers instead of you know two or three versions of like a you know a thank you page with some special offers. Well, hey, we have lots and lots of permutations and combinations that that come from these survey answers. So based on that, we can show you different offers from sponsors or partners or affiliates afterwards or upsells to like a subscription or course, whatever it is based on what you told us. Really, really exciting. And then we can then feed some of that data into the ESP and start to personalize something like a welcome series in a really fun way. So that way, you know, I think about this for me, for instance, that reader who subscribes to Inbox Coactive, the reader who works at a newsroom, looks a lot different than the reader who is on Beehive or Ghost or Substack. Even within those independent worlds, Beehive Ghost versus Substack versus kit, that sort of thing. A lot of different choices that you're making. And the dream scenario is that someone could answer some questions and then I'm telling them about different offers, either ways they can work with me, or you know, book some selling course I'm selling products I offer, that sort of thing, or stuff from affiliates that's gonna be target to you based on what you just told me. And for me to try to come up with all the different variations of landing pages and going into my ESP and giving it rules for dynamic content would just be incredibly complicated. But the dream scenario is that all right, based on you know you signing up for this thing and telling me a couple things, I can then show you a lot of different stuff to help you in a more personalized way that is good for you as a reader, because it feels much more relevant than just having this something generic and that also drives revenue for me. And so I get excited about that sort of thing. And then of course, within the newsletters themselves, if you're, for instance, if you're a nonprofit that I'm working with, you know, there's different messages that might get you to convert and become a donor. And there's only so many that we can test at once. But I'm excited about the idea of using AI to say, hey, we want you to try to uh help us, you know, we're gonna give you some basic rules, voice rules, but help us identify the right segments of the right people so we can go a little bit deeper with some of our segmentation and targeting than we could before uh to try to get people to convert and donate. And so there's a lot to unpack there. I'm still trying to figure out the tools, how to implement, but I can see a world in which this stuff is possible, and that gets me really excited.

SPEAKER_00 51:43

And there's uh so I had a conversation a few weeks back, a couple months back, maybe, modization of newsletters and stuff, and it was a very good conversation. Uh, and it all ties back to attribution, where I think now AI even more than ever is gonna be a big, an even bigger issue. Um, where newsletters, newsletters general, but email in general, newsletters specifically over the years, uh from the traditional media space and stuff, they always sold that inventory. They didn't sell everything, they always gave that inventory as like an free add-on, right? Like uh, oh, you got you know, you're gonna be in the newspaper here, this, plus we're gonna throw we'll we'll throw you extra impressions on the website and the newsletter and just kind of bucket it in to get more impressions out there, devaluing basically the the true value of that audience. So that's been an uphill battle since. And, you know, slowly there's been, you know, quite a bit of ad dollars coming into the newsletter space and things like that, which has been good. Still not enough, uh, in my opinion,

AI and monetization: the new welcome flow

SPEAKER_00 52:45

because it's still predominantly taken by more direct response buyers, more people that are looking for it as a at as an end-of-the-funnel, last touch attribution point where oh, I didn't get any, I didn't make any money off of my my click from your your newsletter, it didn't back out for me. And not enough value of people giving a top of the funnel awareness. Yeah, this is the first time they ever heard about you, probably from my newsletter. And now with AI, even more. And this is this is more of a gonna be more of an industry change of a mindset change and conversation between companies and advertisers and the newsletter operators, like changing the thought that no, this is a top of the funnel. You're getting access to our audience to learn about your product. This isn't just a direct response. Other than driver, you're gonna drive a lot of uh of signups or a lot of sales and stuff right off one cent going out and more rent. And now with with AI, you know, the worries like if if click rates go down and monetization is gonna go down even more because of that, that doesn't mean there's no value with even if they're seeing AI summaries, even if they're seeing whatever, they're still seeing the brand, whatever the sponsorship might have been. That's what I'm interested to see what happens. I think it needed to happen already, these conversations. And I've been talking to my uh clients last year or two, telling them, like, hey, you guys need to stop selling your inventory on a CPM basis. You sell it flat rate, you can tell them you can expect X amount of clicks, X amount of traffic if you want. Like, this is what you can expect, but don't sell CPM. It just shoots you in the foot because, like, oh, I sold million million impressions of inventory. I gotta, I gotta, I gotta ship out a million uh newsletters, but their deliverability is hurting. They can only, you know, they're they're not delivering, they have a 10% over rate, 15% over rate. So sending to $100,000, they're sending uh they could be sending to 40,000 and have the same route, you know, same amount of clicks and activity that they would normally, but just compound the deliverability hurts. So they're not getting performance. People are asking for make goods. It's just a vicious cycle of things happening where they need to, the newsletter people need to take more control and and value the audience of what it actually does, then that where it's at right now with AI, I think it's gonna make it that much more important about we focus on that.

SPEAKER_01 55:00

Yeah, I think too, you mentioned Adam from Work Week earlier in the conversation. I'll give them a shout out here. Some of the stuff they've been playing around with to try to figure out how do we connect the dots between the reader who clicks in our newsletter on an ad and that ideal customer that the advertiser is trying to reach and sync up some of the data to be able to show not just, hey, this person, you know, we got X number of clicks, but these specific people who you were trying to reach are the clickers and are the engagers. And I think this is a really good moment now for all of us in the industry to not throw away the best practices that we have done or the practices that you've employed for a while, but to say, if we were to start again, if we were to start from zero, we didn't know anything about how to run ads, for instance, you know, would you just sell it on a CPM basis? Maybe not. Maybe there are better processes or better ways that we can, you know, implement advertising or partnerships, or better ways that we can sync the data, or better ways that we can use AI to help target the right people with the right message. This might be a good time to break with the past a little bit and say, okay, well, AI is gonna disrupt a lot of things before we let it disrupt this part of our business. Why don't we go ourselves and see what we can change and how we can make things better? Because I do really the only teams that I worry about are the ones who are gonna try to cling a little bit too much to the stuff that, you know, maybe worked in the 2010s or the early 2020s, and may not work in the second half of the 2020s, and may not work at all the 2030s. And, you know, I still see, like in the news world, there are still the teams that I work with who are, you know, our newsletter is an RSS feed of the they eat stories we published in the last 24 hours in reverse chronological order. Like, we can do better than this, guys. Like, well, this is how we've always done it. Like, that's not a particularly good reason for us to keep doing things this way anymore.

SPEAKER_00 56:57

Is there anything you can think of the newsletter ecosystem, news ecosystem that AI can't replace? I think there's a matter of your voice, but I'm pushing back. I think I think a good Dan Oshinski day, the uh Dan, the AI.

SPEAKER_01 57:11

You still have to have that perspective

The attribution problem and why CPM is broken

SPEAKER_01 57:13

and voice. And voice voice also means like it's not just like the way I structure sentences, it's how I approach problems and how I think through things. Nope. It's the topics I choose to write about, it's how I interact with my audience. There's voice means a lot of different things in there. And to me, some of those initial choices, who do I want to write for, what kind of content that they need, how do I approach things like partnerships, like AI. I don't want AI to replace those those choices because those are kind of fundamental to the newsletters that you're creating or the businesses that you're building. I also think more and more, a lot of the stuff that's going to resonate with audiences is going to be, you know, more of the one-to-one kind of touch sorts of things. And that that could be things like email replies, but it's also things, you know, events. There's a reason so many people in the newsletter space are excited about events because we're all trying to figure out how to get out from behind our screens and connect and meet people and share new ideas. Well, I even think certain things like print products are probably likely to make a little bit of a comeback in certain ways, because there is there's something to be said in a digital world for having personal connection or having that touch point, the literal touch point you're holding that thing in your hands. And so I think if you really wanted to, there's a world in which you could AI probably everything. And we're not that far away from it. I could AI can write, it can research, it can design my landing page and build my funnels and do all these sorts of things. I would just say you still want to find ways to have the person behind that in the inbox. Because I do think people are gonna be what wins in the inbox in the long run, and we want to think about these AI tools as helpers and assistants as opposed to, you know, all right, they do everything for me and they make all the decisions for me. They're powerful, but I don't want them to be all powerful if you don't want to say.

SPEAKER_00 59:21

Oh, don't get me wrong. I have I I have guardrails in mind, especially for programming. I'm like, you can do this, but you can never do this. You gotta I can only request you to do this. So it'll go do its thing, and then it's like we still gotta do this, but you need to give the okay for but it also holds back because like there's people that are and then that this is more development um aspect that they have stuff just constantly running and churning and doing things and programming and learning and and uh just gotta be fully autonomous. So like um you just gotta be careful because when it's doing that, yeah, they're churning all away. If it updates something wrong or a production that it shouldn't have, and the whole system goes down, then it's like uh who knows how long.

SPEAKER_01 1:00:05

Yeah, I want to give you a better it's a really good question, yes. And I want to give you a better answer to this, and maybe a little bit a higher level answer, which is like the one thing that I hope AI doesn't take away from us the long run is our curiosity, is that sense of looking at a product or looking at a problem and going, why are things that way? And how could we make things better? And what else can we try? And I think AI could be part of helping solve some of those problems, but there is still that that truly human thing where you look at a problem and go, huh. I mentioned earlier I was editing the story, it took me a while, and part of it was because it started as a Q there was a pitch for the story that was really good. I liked, and it the the interview came back and it was kind of presented in a QA format. And I read it and I went, I've read this story and this interview with this person. I'd seen this one before. This person we interviewed has been interviewed many times. I was like, I've seen this before. And I went on a walk and I was out there just like how else could we present this content that's gonna make this feel original and new and different, and in particular, help my audience get the insights out that they want so they can do something with this. And so that curiosity in trying to solve that problem was really fun. I think we got to a point. I'm pretty excited about the story. Like, I think we figured out a way to present the content that people are gonna like, but that curiosity piece of it really matters. I hope we don't lose that. But I can't wait.

SPEAKER_00 1:01:30

Yeah, we won't we won't, because it's it's you know, you still need to, it's AI is good at, I mean, I guess we'll never know where it gets to, you know, when it becomes sentient, but uh the you know it's it's it's good at analyzing stuff, it's good at at knowing what to look for, how to apply things that have already happened, and and and knows how to do things, fix things, informate. It's got its own information. What it don't know if it has are those those out-of-the-box ideas, the things that change the world, right? Like out of nowhere is is AI gonna be sitting under a tree when an apple falls. Like, oh, there must be something pulling the apple down to the ground and come up with gravity, right? So you're always gonna have to ask questions. It that happens when I'm programming or I'm and I'm doing stuff and I'm trying to figure out the system architecture for our app and stuff, and it's doing something like, okay, but what about this, this, and this? And and if this happens, you're like, oh, great idea. That could happen. Then what you have to do is whatever. And then, like, so you always have to be angles, yeah. And you gotta have the pushback, you gotta give, like, what about this? And then what about that? What if you so you still have to challenge it, ask it questions, give it, give it ideas, gonna help you fine-tune those and and help you discover them, but um, it's not gonna do it on its own. I don't I don't know if it ever will. I think that's right. I know we're probably getting down a bit. We've been we've been on here for a while. I'm not sure what your your hard stop is, but just a couple closing questions. Sure, let's do it. What's one thing in newsletter publishers are worried about with AI? The unknown piece. So the writers losing their jobs.

SPEAKER_01 1:03:06

No, no, no. There's that, but the unknown piece of it.

What AI can't replace

SPEAKER_01 1:03:09

I talked about this at the conference that there's these different potential paths that it could take. There's a world in which AI and the inbox, AI agents, AI tools make it so that people don't really need to use their inboxes in the same way. And we don't know whether that will lead to outcomes that are good for newsletter folks. People spend more time with the content they want, or that people spend less time in the inboxes, period. And that unknown, of course, is very scary. Uh so much of the newsletter space, your job and mine for many, many years, is built around this idea that email doesn't change all that much. You have this stable place that you can go and build. There's no one big algorithm or company that sets the rules. It's not like social media, email is different. And AI will potentially challenge that notion of email being different. And so that unknown to me is that existential thing. Like, what does email look like in a decade? If you had asked me 10 years ago what email looks like in a decade, it would have been email looks a lot like it does today. And it still largely does look the way that it did 10 years ago or 20 years ago. What does email look like on you know, we're recording this thing on June 30th? What does the email look like on June 30th, 2036? I truly do not know. I think it'll look probably larger the same in a year or two or three as we implement or implement more AI tools, but that fear of the unknown is the big thing. It's tough to play in for what you don't know. It's tough to play in for an unknown future. But it's also exciting. It is. You just gotta have that, you gotta have that mindset of this could be exciting. We have to be open to possibilities, things are gonna change, and that'll be okay. Let's not cling too tightly to the past. What we build next may be more interesting and more exciting than what's come before.

SPEAKER_00 1:04:56

What book are you reading right now?

SPEAKER_01 1:04:58

I have a couple things that are on my bookshelf at the moment. Uh, if you're looking for, well, the book that I'm reading right now. Oh my goodness. I'm forgetting her the author's name right now. I'm gonna have to Google this live on the call. I wasn't prepared for this one. Uh Pen 15 author. I never I never know the author's name. See, this is what happens when uh it's a writer named Anna Conkl. She had a series called Pen 15 that was on Hulu, and she has a book right now that is called I'm enjoying the book too. I just don't remember what the title is. Uh it's called The Sane One. I've enjoyed that one a lot. It's fun. It's like uh she's had a weird, strange childhood and writes about her fake crazy family and that sort of thing. And I like funny, weird, sometimes sad stories. Um, that's a really good one. And next up on the list, I'm really excited for it. Uh Joanna Stern, formerly of the Wall Street Journal, she talked at the newsletter conference this year, and I got a copy of her book, which is all about AI and how. How she used it over the course of a year. So I'm excited to get into that one because it's kind of same kind of I so much of this right now. I just I like conversations like this. I'm still figuring out so much about this. And I definitely am not in that place where I go like I got it all under control. It's like there's so many questions. And so I'm always uh I'm so I'm so fun to have those conversations with people like this. Just be like, what what else are you doing? What else are you trying? What am I missing? Where are my blind spots? So I'm excited to read hers because they're just always interested in how people are trying to mess around with these new tools. Where's where's where's Joanna from? Joanna's formerly the Wall Street Journal. Uh, and then her book is called I Am Not a Robot.

SPEAKER_00 1:06:43

I think I think it I think I saw her speak at uh Mbox Expo in Atlanta.

SPEAKER_01 1:06:48

Well she was at the she was at the newsletter conference this year too. She did uh she did one of the first.

SPEAKER_00 1:06:52

I think she was at more stuff.

SPEAKER_01 1:06:54

Yeah. But I'm excited. I got a copy of the book. I'm excited to read that one as well. Just always, she was a Wall Street Journal tech columnist for many years, and so always curious how what are other people messing around with right now with this thing? Like what's working and what isn't? The what is it is by the way almost as interesting as the what is.

SPEAKER_00 1:07:09

Well, I'm reading user story mapping right now. Uh, I had to look it up because I can't remember the guy's name. Uh Jeff Patton. Um, but it's all about, you know, instead of the traditional like creating whatever your your the campaign is, or especially development is more tied to development too. Like you're like trying to like give requirements and things like that versus developing a story of what needs to happen. It's how you can map all that out and like all these sticky notes everywhere you're supposed to do. So that's AI. I feel like we gotta knowing the whole journey is gonna be the biggest important part. That's fine. Um well, I think that should do it. I I appreciate talk. I thought it was uh a good one. Do you wanna give a little uh pitch on where people can find you? Obviously, all over social media, inbox collective. Yeah, inboxcollective.com.

SPEAKER_01 1:08:01

Uh I the only social media platform I spend any time on LinkedIn on is LinkedIn. Uh, we've got, by the time this conversation comes out, it should be live. The next of these free email courses, the next uh we have one live right now about how to grow your newsletter. Uh, the next one, totally free, is gonna be about how to audit and find mistakes and things in your newsletter, not fixing typos, but hey, there's these holes in my newsletter strategy. How do I fix them? How do I build a stronger strategy? So I'm really excited about that. Just finishing that one up right now. Free to subscribe to you on inboxclap.com. Oh, and if you happen to be someone who can throw a baseball 100 miles an hour and you're looking for a job, call my Washington Nationals because we could use a bullpen pitcher.

SPEAKER_00 1:08:42

Um the uh we which you should do in and your the course thing at the end is create some little upsell at the end for some uh AI prompts.

SPEAKER_01 1:08:54

Well, that's a fun idea. I like that. The the first version that this is a long-term play. First version is putting the courses out, getting people to take them, learn surveys of other things to learn how people react, and then figuring out all right, the content, the structure is there, how do I add more? And certainly some of the stuff we talk about, like upsells, love that. I get the AI ones, that's a really fun one. I'm a steal. Uh, is definitely on the list of things of all right, if people respond well to these, great. How do I add more to make them more valuable for them? And also to monetize, too. Right.

SPEAKER_00 1:09:24

Fun. Awesome. Are you speaking anywhere coming up or gonna have a break?

SPEAKER_01 1:09:28

I have some small uh gigs coming up at some various media conferences in the not too distant future, but nothing, nothing huge, no giant, you know, uh nothing quite like speaking on stage at the newsletter conference in New York. I'll be in Palm Springs, California at the American Alt Weeklies conference.

The biggest fear: the unknown

SPEAKER_01 1:09:46

I'll be up in Alberta, Canada in the fall speaking at a conference, uh a bunch of magazine publishers in Canada. I'm excited about that one, but small stuff for for right now. Otherwise, I I I like being I like living where I live. I I try not to get on planes too often, but I don't have to.

SPEAKER_00 1:10:02

Right. Well, I'll be speaking next week at uh at Market Beat. They're doing their FMS mastermind over there, so enjoy. That's all I got going on. Enjoy. Well, enjoy your fourth of July. Thanks. Thanks for having me. I really appreciate it. Yeah, it was great. All right. See you soon.