How Tyler O’Shea Fixed His Deliverability and 2X’d His Open Rates

Cool. All right, Got Tyler o' share here from. Sorry, o'.

Shea.

I got slurred there with my Invisalign from the Underdog newsletter. And we met back a few months back, back in the spring, maybe of last year.

Yeah, I think so.

Found us each other on Twitter and helped them out a little bit, getting to understand more about email deliverability. So I wanted to have a chat with him on how things are going, his newsletter, what he's learned over that time, what's working for him, and then you know, just kind of spit off from there. If he's got any other things he wants to kind of dig into, ask questions with, we can do that as well. And so if you want to go ahead and just give your little elevator speech of what inspired you to start the Dog Underdog newsletter and how it's gotten to where it's at now.

Sure. Yeah. So I got cut from the baseball team in seventh grade, and long story short, I was digging into the weeds, looking for inspiration and a reason why, you know, I should continue playing baseball, basically, and, like, keep trying. I was always undersized. So I looked to those stories and, you know, after graduating college, launched my own website, got into the newsletter game after that, and, you know, my whole mission's built around telling inspiring underdog stories that are happening around sports or have happened historically, to kind of give that inspiration to future generations, you know, people of all ages, to give them the same feeling that I. That I was looking for when I was, you know, that undersized baseball player growing up.

Nice. And how big is the list right now?

It's at 22, close to 23,000 now.

Nice. When. When you started building the list. And I know we went over this. We first met. What were your issues you were having? What was the deliverability problems you were having, or what were the challenges you were facing when you're trying to kind of catch your stride of the newsletter?

Yeah. So, I mean, our conversation last year was, like, pivotal, I would say, completely changed, like, how I approach things. Like, I. I was sending to my entire list to begin with, always. So basically, the. The engagement was dependent on the source of subscribers that I was pulling from in a given month. So if it was Facebook ads and if it was a lower quality ad or for whatever reason, Facebook wasn't targeting the right people that month. My list, like, my open rate would slowly erode over time. So it got to a point where Beehive actually emailed me last, probably April, and was, like, flagging my sent, like, me as a sender. And that was like, holy crap.

Like, what?

What am I gonna do? So luckily, I came across you on Twitter, and I feel like, yeah, like, I. I didn't really know what to do. And we jumped on a zoom call, and, like, you gave me a lot of free advice, which was amazing. And I had such a hard time accepting that I had to send to less people than I had on my list. And, like, that was really hard to grapple with. But I actually pulled up the metrics, and from that time, like, April, May, June, I cut a few thousand subscribers and then just kept sending to the entire list. And then I think after we spoke, I implemented a base sending segment and started just sending to them. And then I think I originally got a little impatient. So a couple weeks after that, I sent to my full list again. And it was a story. It was like, 25 open rate or something crazy. And then I was like, all right, I just gotta accept it. Trust the process, and then over this next year, commit to this. And I've been doing it ever since. On my open rate has gone from, like, at its lowest, it was like 23, 24%. And I remember showing that to you, and you're like, for. For your kind of newsletter, like, that's. That's not, like, right, like, there. It should be a lot higher now. Like, we just had our most unique opens ever this past Sunday, and we're trying to keep hitting new records. And it's like 55 open right now, which I'm really happy with.

Yeah, that's awesome. And I just shared in my newsletter this past week about the. I called the news newsletter engagement flywheel. You know, the Flywheel is a big, hot thing that's going around now with the term, so I went with that. But, you know, it's basically what you're saying, like, to be able to grow your list and keep growing it, you gotta. You gotta have the engagement, right? Because the engagements, which shows all the ISPs that people want your newsletter, they're reading it, they're engaging with it, which means they're gonna put you in the inbox. Otherwise, you're gonna end up, most likely spam. And then worse off, things get really bad if you keep on sending the whole list and never stop. You know, you start getting bounces and, you know, get. Get into the hole. So by getting that engagement metric higher, you're actually getting your domain reputation up, which is putting stuff in the inbox, which then more people are seeing. When you're onboarding these people On Facebook, no matter where it's coming from, everyone's getting in their inbox now versus maybe a small percentage of them or none of them, which then your list is going to keep on growing and it keeps growing, growing, growing. So the earlier people understand that and they get this whole idea of a base sending segment or focusing on engagement and not just list size. They're going to see their, you know, their list grow, you know, effectively. Not, not, not the list size. It's. The list size is always a vanity metric. Right. You want to engage people there. But then you can totally see it'll start, you know, ramping up, which I think you're starting to see here, at least in the past couple of months I saw I've seen some good growth from you and. Good. And your engagements haven't gone down. Right. So your list is growing, your engagement is not going down. So it's not like you're, you're churning out and then, you know, purging out subscribers. That affects anything. You're just keep on sending to the people that are engaged and your list is growing.

So yeah, and I think, yeah, if anything, engagement's gone up as I've grown. Like it's something that I've seen. And I think another thing I learned from you was like monitoring specific ISPs. I guess that's, that's what it is, right? ISP is like, yeah, service providers. Yeah. So I have it like, I have it very basic for myself. Like, you know, I have Gmail and non Gmail. I also have everything else broken out, but I have like last seven days because I'm a weekly sender. Last seven days sent, last seven days open, last seven days clicked. And just like monitoring that every week is helpful. My Gmail versus non Gmail are pretty similar in terms of open rates. Around 50%. Gmail tends to be a little bit higher for whatever reason, probably because there's more people in, in that bucket. But and then also like the idea of the, the base sending segment, I think when I first started I was just like very like keeping that tight. And then I like, I slowly expanded it as like my reach or my open rate like started being consistent or growing. So I started expanding that a little bit. Now I think I'm at like 120, 90, 60 or something like that.

Right? Yeah. So that, I mean that's a perfect example or explanation is it hurts in the beginning when people get this concept of base setting segment. I'm getting rid of a bunch of people and now I'm sending to 60% less or whatever the number is. But one of the reasons you do that is because you never did it before. So you gotta take the medicine, unfortunately. But if people start off with that, then the idea is that you're always going to have good inboxing so you, you won't have to, you know, cut your knees out, spot your face, whatever the saying is, where in your case you have to tighten up probably tighter than we may want it to because you want those engagement metrics at the inbox. And then you're doing the right things, you slowly start losing it up. If you don't see your, your engagement metrics changing, your open rates are the same, your, your click percentages are the same, then yeah, keep on loosening up a little bit because that's also going to help try and re engage people that may have fallen off already. So you're, you're doing the right thing there. It's perfect.

And then I also, I loop in those people. I, I think I even named it like audience bridge segment like from your newsletter. Because you know, people who have clicked anytime ever or anytime in the last 365 days. I'm not sure what I set it up as, but looping them in every so often to try and re engage those people is helpful too.

Nice. Do you have any questions or issues or things you'd like to touch on?

Yeah, I mean, should I, should I expand my sending segment even further? Like now that it's been like I've been over 50 open race for the past probably couple months now.

I, I would, I wouldn't be scared of opening it up a little bit more. I mean again, it's just the way you're doing your, your introduction every once in a while of the, the AB segment you call it is one way for the re engagement by expanding your, your base segment out, pushing it out a little bit more. It's another engagement technique, right? You're just adding more people that may have engaged in the past. I would, I would expand, you know, openers, clickers, numbers. I would never expand out your. You're added, right? Newly added, whatever that base is like they've had enough time to open or click. If they haven't, don't send to them. They're not interested. It's just a waste. All I can do is probably hurt you. So I would, I would leave that added. What is that at 30 days? 60 days?

30 days? I think actually no, it might be at 60. Actually now might be 60 because you.

Said once a Week.

Yeah, I think it is 60. Yeah, but just as like a testimonial for, for your help with me. Like, I have, I have all the numbers in a spreadsheet. So I started tracking in July of last year and I believe we talked like towards the end of June maybe. So like my base sending segment, my, my list size was like 13,500 at the end of June. And talk about like the pain of like just narrowing down to a base sending segment. It was like 90, 65, 33. I think I did something weird and the base sending segment size was like 6700. But at that time I could just, like I could even just share my screen to show you. Oh, sorry, you can go ahead. Yeah, just to show you my post report. I just thought it was interesting to look at. So from that time, can you see this?

Yep.

Okay.

Yeah. So from that time, like it was, you know, 20% was like the low before I really started sending to the base sending segment, but it was like 29%, 30%, 37. Like you could just see it slowly climbed and like, I don't even think I was really even growing my list during this time. Like it was actually getting smaller to the amount of people I was sending to. But once like I got this open rate up a little bit, it's just steadily grown since then. Like the engagement, like the number of people opening my newsletter, you know, even. Even though the list only grew like by say 2,000 people, the unique opens are like what they were, you know, like, like I'm reaching more people in the inbox objectively. Like there's no debating that. And you know, click through rate was really strong. I. It's kind of gamified in, in Beehive because of the poll feature. But you know, you'll see like this has come down a little bit since then. But then I turn growth back on. You know, now you're, now you're getting like 5,000 into like the 5,000 range. And now we're closer to like the 6,000, hopefully 7,000 unique opens range. But you know, I'm still sending to a very small percentage of my list, like compared to everything else, like to the, to the total size. So, you know, I probably have to delete like people and actually remove people now because I, I've like that's the last thing I'm clinging onto is like the size of the overall list in my mind. Like, I just don't want to go back down. But you know, I'm, I'm just mainly focused on this, this base sending segment. But I've kind of tracked that over time here. Just checking in, leaving my notes, measuring the, you know, welcome email engagement over time. I have a second welcome email that goes out seven days later, but just tracking that. And then I also have, you know, not engaged. A lot of overlap here, but removing hard bounces. People that were sent, not delivered. But, you know, it's, it's been really helpful just for tracking all this stuff and knowing that I have an engaged list of people that actually want, want my emails.

Yeah, that's awesome. And congrats with the sponsorship for the, the movie that went out. Yeah, that was, that was cool.

They reached out to me. It was like an independent film and it was really well received and I thought it was a really good fit. But that's something I'm trying to get a little bit better at is like only accepting sponsorships that are a good fit for, for my audience.

Yeah, that's always a tough one.

Yeah, it's hard to pass up money.

Yeah.

But also that's, that's why you release your own products too. Like, the book did pretty well. So, you know, I'm trying to focus on more future products, like maybe a trivia card game or something like that to go with my trivia, which is like the most engaged, engaging section of my newsletter usually. But yeah, there's a lot. There's endless ways you can monetize. And I think, you know, it's only up from here.

Yeah, it's awesome. Well, what do you think the, the most common mistake is for. For people that are doing newsletters on.

Their own, I would say not respecting the relationship with the inbox. Like, in general, like, beyond deliverability. Like, if a person signs up for your newsletter, they need to be treated with respect. Like, you're taking up real estate in like their phone and they're in their laptop inbox. Like, that's, that's like a pretty like, intimate, like, relationship in terms of like, compared to social media. You can like follow unfollow people and like skip past things. Like if someone's coming into your inbox. Like for a lot of people, like, that's where like everything is managed is like their work email or whatever, their personal email. Like, they, they curate that very carefully. And like, just like people don't want to get like blasted with spam text messages. You shouldn't blast them with emails that they don't want. Or even like the survey thing. Like for B2B, it makes sense. But like, I see some B2C newsletters like putting people through like a five step process just to sign up the newsletter and like just get someone signed up and like show them value immediately and like why they, they should like why you deserve their attention basically.

Cool. Just thought popped my head going back to when you were saying how you have your, your Gmail stats segments and then the other domain segments for monitoring. When I did the webinar with EJ last week or the week before a couple weeks ago he did mention that they are because I have my own software that we built to track that on our different ESPs that we use to pull in there so we can see the stats for having to calculate it and look at it all the time. But he said they are coming out with that, that's on the roadmap being developed right now. They don't see delivery by domain group.

Yeah, that'll be amazing. And yeah it's, it's helpful not to have to make a bunch of segments because I have like 150 plus segments right now.

That was the problem with BE, which I mentioned on the, on the, on the call was that their segments obviously they run for the web but then they'll, they'll go dormant or they'll, you know, they won't run anymore because they just don't want to use all that processing power for all these segments for no reason. So that should be coming soon, which will be great. And also are you doing any email cleaning as far as email validation of the people that are signing up or. No.

So I have like where my signup boxes are. I think I have like embedded with it like the cloud flare or capture.

Google Capture.

Yeah, the Google capture like the invisible captcha I believe. So I'm hoping that's enough. I mean when I try to like I get signups to like a third party tool I use like through my ad network. It's like kind of like it's called like a Spotlight subscribe like model basically and I have to like manually upload those subscribers and like oftentimes like Beehive will reject them or it'll be like a duplicate subscriber. So I feel like they're pretty decent at like cleaning the list up front. But yeah, I am kind of worried in the back of my mind about like spam traps or anything like that that could.

Yeah, you're gonna want to check that out eventually. Beehive did say that that's another thing that they're coming out with is okay email validation service kind of built in natively so that they can actually use a third party person, whatever software to check that it is not a spam trap or bundle of roll or whatever it is. So.

Okay.

I mean, they're, they're innovating a lot and releasing a lot of new features. The one problem I will say though, if they, if they're, if anyone listens to this, like their, their template roll out was like horrible and it like ruined my, my newsletter template. But I think they fixed it so.

The new website builder came out and it messed up the way your, your newsletter was set up.

Yeah, like they rolled out like a newsletter template thing with that or something in it. Yeah, it changed.

Well, that sucks.

But I saw a lot of people, other people complaining about it, so I think they did fix it.

But does it find out for you or do you have to like just rework your whole template to fit the new.

I kind of had to rework it to make sure it was good, but once you do it, I think you're good. Until they release another feature, then they roll it back.

Yeah. New one that doesn't work on the old one.

Yeah, I mean, not a big deal. I mean, I can't really complain. They're. They're pretty cost effective for what they.

Yeah, they'll figure it out. Well, a few, a few side topics here. Since you are into sports and you have a sports newsletter. Who are the Eagles drafting tonight?

Honestly, this is the first year I haven't really cared or paid attention like their draft. I. I haven't even looked at a single mock draft this year.

Well, you're lucky.

Super bowl champ.

I mean, I have, I have it pulled up right here.

You guys, who are they projecting at 32?

Projecting? Josh Conley Jr. Offensive tackle from Oregon. Actually a guy that I would want for the Dolphins.

Okay.

Yeah, I wouldn't mind bolstering the O line. I mean, we had some injuries in the playoffs where Jurgens had to push through and Dickerson had to push through injuries to play. So you can never have too many O linemen.

Speaking the defensive line.

Then where are you guys?

Which we need about 1313. But I mean, we need everything. We need defensive line, we need offensive line, we need quarterbacks. Ramsey's gonna be gone. So all we have like no. No cornerbacks, no secondary, basically on our team, really. Only thing we have are receivers, an injured quarterback, and that's about our team. And a running back. A chain's pretty good.

It's concerning to see like TUA still going out there and like putting his Body on the line. And like, I feel like they got to make moves with their receivers. Like just either trade Tyreek Hill or, like, do something to like, get some more talent in there, you know? Like you.

You figured they would have trade Tyreek this year, but yeah, he's not. He's not a. Adding too much value with all his antics. So I'm sure his stock isn't. Isn't that they probably want Waddle more than him. And who you got winning the. The NBA finals?

I'm not a big basketball guy. Honestly. That's like the one. My one weak point is I really can't write well about basketball. I don't know. Who do you have?

Who do I have? I want the Heat to win. They're probably not gonna win it. I. I think. I don't know why. I just. I think the Lakers are gonna win it because.

I don't know.

Yeah, I think. I think it's Luca's time.

The narrative too.

Yeah.

Doesn't hurt.

I don't care about LeBron winning another one. I just.

Yeah.

Like Buka, were you a LeBron guy when he was down. Down there?

I mean, we're always a way guy, but I mean, it was great to have the best player in the league down there. So it was fun until he left, but. Yeah, liked him. Liked him when he was there. Don't like how he left. And I think he. It's his fault that Wade ended up leaving. Not staying the whole time with the club because of his, you know, ah, you should just leave and get your money here. They don't. Whatever. And so he left and they came back anyways. But that was my. That's probably the biggest thing I hate about that. Yeah.

I mean, that was an iconic ESPN special when he announced that he was.

Coming to the Heat. Oh, like the boys and girls club.

Crazy.

What a crazy time that was.

It was awesome. And then what about Stanley Cup?

It's another. It's another weak point.

Man.

I can't keep up with all these sports. I just follow, like the story. Yeah. I. I mean, when the Flyers have been horrible. So I just really haven't watched hockey as much lately.

Panthers here that are, you know, pretty good, so.

Yeah, always pretty good.

Yeah.

It's pretty funny that the Florida teams, even the Lightning, are like, that's the most southern you can get in the US and they're the best in the NHL. Hockey, it's crazy.

You don't think of, like, Florida as a hockey, like hub, but it kind of is now.

Oh yeah, it's 100. It's funny because my, like, I live West Palm, so just north of Miami. One of my good friends back in high school is in Tampa and they're big Lightning fans because their son plays hockey over there. But they got like crazy hockey, ice hockey leagues and stuff all over the place now because of these teams. Yeah, it's like travel hockey and it's like huge. I'm like, geez, Florida.

Yeah.

Don't get it. Like, get out. And it's freaking 105 degrees up.

Crazy.

It seems awesome down there. I mean, I've always kind of saw myself in the future living in Florida, but I know it's changed a lot.

It's good, freaking packed. Traffic is out of control.

Have you been there your whole life? I forget if you, if you said that.

Yeah, I've been, I've been, I've been down here pretty much my whole life. Went to Florida State University, then came back, back Palm Beach County. So I've been here the whole time. But you never know. Eventually I'll probably move once my kids are away and out in college. Maybe move to the mountains or something. Some little slower pace.

Yeah, that'll be a big difference, right?

Yeah.

Yeah.

I mean, we love it whenever we go to the mountains or the lake. It's so peaceful. And sit there by the fire, smoke cigar, go fishing. Pretty much a dream in my opinion.

Get away from the screens.

Get away from the screens. The noise, that's. It's awesome.

Yeah. Yeah.

But can't take my kids there and then they're away from their friends, school. It's like, but not too much more time.

That's my biggest struggle this time of year is like I work remotely. I'm on screens all day. My, my newsletter is on a screen. Like I have to look at a screen all the time and like, I just want to be outside, so I gotta find a way to work around it.

Are you, you're not going to the newsletter conference, are you?

No, I, I haven't been able to make any of these conferences and I'm kind of regretting it because people reach out and ask if I'll be there, but maybe once I'm a little bit bigger, we'll see.

You're getting there. I'm impressed with, with the growth and what's going on. And you can just see with all the, how much attention you, you put to it with your spreadsheets and everything that you know you definitely wanted. So it's going to get there for sure, Yeah.

I appreciate it. Is there, is there anything I could do to help you out? Because you've given me a lot of free, free advice and help. I mean.

Yeah, I mean, this is, I mean, more than. It's like, you know, you, you, you've, you've taken the stuff that you've learned, and it's not just me. I mean, you get stuff from all other people and I see you talking about it and you just, you can learn a lot out there and apply it and be successful at it. You know, that's, you know, that's the biggest thing.

Yeah.

I mean, the space is like, getting invaded with, like, a lot of, like, people that don't know what they're talking about. So, you know, that's the one thing I'm kind of trying to push people towards, like the right people to get advice from and kind of ignore, Ignore the noise that's out there because now.

It'S trying to focus more on, on, on the engagement and, you know, deliverability side of things. I don't think enough people talk about it out there. I don't think enough, enough people understand it either. You know, like you said, everyone just gotta get bigger. I'll keep on sending.

Yeah.

Until you get to a certain size, and then it doesn't work anymore. Now you're screwed. So.

And I'm glad it happened to me at like 10,000 instead of like 50,000, because this would be a whole different conversation at that point. Like, it would be a business. More of a business problem than just.

Like a. I mean, like, you, I guess you looked and you said you weren't having that Yahoo problem, but that, that, that Yahoo block that's happening right now is devastating people.

There's some people, people, like, people won't prioritize this stuff until it is a problem. That's, that's kind of what I learned. At least in my experience. Like, it's not a sexy thing to talk about or care about, but, like, it's a big difference. Night and day.

Yeah. Well, cool. Great. If anything else, you know, always reach out, keep in touch and looking forward to seeing. Oh, and don't forget to go out and buy his books on Amazon. Bestseller.

Briefly. Briefly.

A bestseller in five different categories, not a bestseller in one category. One time.

Thank you. Yeah. Thank you for reading it and, and for, for the shout outs about it. I appreciate that.

Yeah, no problem. All right, Tyler, we'll keep in touch. Talk soon.

All right, thanks, Chris.

Yeah, bye.

See you.