Episode 416: Leveling Up Your Email Marketing With Adrian Tobey

Show Summary

Rob Cairns talks to Adian Tobey about Email Marketing.

Show Highlights:

  1. Why does E-Mail marketing matter?
  2. Subject lines in e-mail marketing.
  3. Groundhogg roadmap.

Show Notes

Hey everybody.

Rob Cairns here and today I’m here with my guest, Mr. Adrian, Tobey of Groundhog. How are you, Adrian?

I’m doing fantastic. Thank you.

Great to have you again and good to see you’re doing. Well.

Yeah, yeah, I’m. I’m. I’m really excited. Thanks for having me on the show today.

Yeah, my pleasure. We were talking offline about some of your thoughts on e-mail marketing and we were kind of saying how e-mail marketing has become very hard. Art, and I think it’s hard to do. And I think. Honestly, AI is starting to convert the whole process just a. Little. Bit what are your thoughts on that?

I I’ve been actually like really thinking about. How e-mail marketing has become. Difficult, and which is? Which is counterintuitive or like or at least counterculture to sort of the e-mail marketing culture that’s out there, which is like, there’s everybody on Twitter saying use AI to like, you know, write your newsletters and. And all you need to do is plug and play 8 subject lines to improve engagement by 30%. And like CRM providers and e-mail marketing software providers are guilty of this and I’m guilty of this as well. Saying like you’re just one e-mail sequence away from sort of unlocking a whole extra revenue stream in your business when the reality of the situation. Is that it’s just, it’s just not that easy anymore. There has been a major effort on behalf of. Inbox providers. Like Gmail, iCloud, so Apple, Yahoo to really. Reduce the effectiveness of of of e-mail marketing in the inbox and make the barrier to entry for small businesses to get seen in the inbox much, much, much higher. And so I have. I have some thoughts and opinions on on what. Sort of. The current state of the inboxes and and what small businesses should be doing. To be seen in, in, in the inbox. So I’m going to start off with just a little bit of sort of like. Anecdotal experience, so I being sort of an e-mail oriented guy. Have a few e-mail inbox I have Adrian at Groundhog dot IO. I’ve got Adrian at Mail hawk dot I got Adrian at Holler box. I have Adrian at adriantoby.com. Those are all e-mail real e-mail addresses. If you want to e-mail me with. A question. Go right ahead. I’m. I keep my ear to the ground if you wanna. If you wanna chat, we can chat. So I I get a lot of e-mail as you can imagine I get probably upwards of 100 to 200 emails per day about. 55% of that is corporate correspondence. Of the e-mail that I look at, I wanna actually. I’m gonna preface that so of the e-mail that I read of those 200, you know, plus emails per day across all these inboxes 55%. Is corporate correspondence. That’s stuff like credit card notices or account information, action required stuff or just like stuff that I have to do just to keep the operation. Running. Right of the e-mail that I read about 55% of that. And then the other 40% is personal correspondence, you know, it’s whoever sending me a cat photo or something or or or. My wife wants to send me an e-mail to book for a special event that’s coming up, like, stuff like that. And then 5% that I invest my time in is. Is. Marketing and there are really only three types of emails that I’ve laid out. There’s corporate correspondence, which is just your notifications and transactional emails and stuff. There’s personal correspondence and everything else is basically just marketing. There’s different types of marketing. There’s different ways to do marketing emails, but really anything that’s not corporate correspondence and personal correspondence. Is just. Marketing and I personally only probably invest maybe 5% of my time doing e-mail. Looking at that like if I see a catchy subject line, I’m like, OK, what’s the? Feel, but beyond that, a lot of it just gets lost in the noise. I’m not. I’m not sure I’ll actually throw it back to you. Do you? Do you? Do you feel the same way or too much?

Yeah, pretty.

How do you invest?

In market. Yeah. Somebody who’s in this space A lot, I find I don’t read most marketing emails. This kind of look at subject signs. Oh yeah, this is good today. This isn’t good today. I’m not interested in the ones that say, oh, you can have 50% off. I don’t care. I. Move on. Very quickly, unless it’s something I’m really looking for, like for example, recently I bought glasses online so the glass company I deal with was sending me emails every day and that I paid more attention to. But once I’m done with that, that goes. Away too so.

Basically right. It’s it’s, it’s a we we get so much.


Yeah. And and especially like now. Our society, more than ever, everybody is stressed out, stretched thin and like people are just over it. Like like mentally there is very little capacity left to invest.


It’s true.

In just the marketing, the basic marketing drivel that most of us are putting out, I’m putting it out. I’m adding to the noise. I know that it it does have its place.

So am I.

Right. Like you, you you still need to have, like, some follow up stuff or some long term nurture like that has its place because yeah, sometimes it works right. But a lot of people are expecting it to work all the time and it’s just not going to. It’s actually it’s probably more uncommon that it works than. Than common that it works right? It’s more likely to not work than to work. Is is sort of my opinion on a lot of the stuff that that we’re putting out and. I responded to. I saw. I saw Derek, who is doing sunshine Photo cart, which is like a cart system for photographers. He was on Twitter and he was like, and he’s actually a a Groundhog customer of ours, which I think is pretty cool. But he sent out an e-mail to a bunch of people that cancelled their subscription.


Vision. And I’ve done this before, right? Just like you. You, you. You round up a bunch of people that cancel the subscription. You wanna send them? An e-mail be. Like, why did you cancel right? And but there’s no segmentation on when they cancelled. There’s there’s all of that. And so you’re sending an e-mail to maybe like 1500 people and you’re like, hey, what’s up? But you’re and you’re super professional. You’re super nice.


About it. But you know, like help me improve the product and or or help me sort of like figure out our analytics here, but there’s really that’s a lot to ask of someone who’s already divested themselves entirely of your.


I think so, I think so.

It’s just, it’s just a lot to add. Like we’re asking a lot from people to pay attention to us when there’s very little in it for them. Like you mentioned that you just straight up ignore the discount code subject line emails. Which is totally fair. I send those, right? They’re not very effective.

I know you do.

The truth is that they’re not very effective. They’re very effective for a very specific target market. Which is not always the target market that. I love to. Work with, but I’d rather you know, take their money than not. So we send them. But that e-mail is is pretty. Ineffective for most people. Yeah. And so the question becomes, OK, so I all all of our emails like they’re not working, they’re ineffective. Like what gives? Like, what do we do instead? Right, like, what’s what’s if we want to be seen and heard? Like what what should we? Be doing and I have. I have yet to come up with a specific formula for how to write. An e-mail that works, but I’m going to take 30 seconds to open up. Something that I wrote a little bit earlier. Because I want to. I want to make sure that I got all my points. So let me just pull this up here. So I want to start off with the first e-mail that I sent that actually worked. Which I sent on April 1st of this year, which is the reason that we’re actually having this conversation. As it turns out. So I sent an e-mail I saw, I saw Insta WP.

Here. Yeah.

Right. They’re they’re great. They did an April Fools joke where they were like pretending to launch. A page builder and they’re like, go like, hey, we’re launching a new page builder. Go check out the details here. And it’s like April fools. This is just a joke. We’re not doing a page builder. We’re just gonna focus on hosting, which is like, ha ha, very funny. And I’m like, hey, it is April fools. I want to do something because I feel like, like, I’m, like, Groundhog is a branch. Like, we’re we’re going towards, like, very snarky, very cheeky. Very sarcastic, like we’re just sort of being counterculture because like all the CRM’s and all like SAS companies basically like all their brand is exactly the. Same and their tone is exactly same. They’re all very approachable, very, very professional. I’m like, that’s boring, right. I wanna. I wanna be a little bit like edgy. And so I sent out this April Fool’s joke because a lot of our brand is associated by being self hosted and open source and flat rate cost.


And I’m like, OK, well, what would be completely contrary to. It’s like, well, if Groundhog turned into a sass and we started like doing the whole software as a service thing and billing based on the number of contacts that you have and hosting data in a centralized location and spying on customers and just doing a bunch of like shady SAS stuff that SAS does. And so we sent out an e-mail. And the subject line was Groundhog is going sass. Right. And we started to say, hey, listen, we’re going SAS because, you know $600 a year, it’s just not enough to charge. So we’re gonna start price gouging our customers by charging more for based on contacts. We’re gonna host all of your data in a centralized location so that we can spy on your subscribers and do a whole bunch of shady.

Yeah. Yes.

Privacy stuff. We are going to what else did I say in that e-mail? Because it’s hilarious. e-mail. UM. Oh, yeah, so we’re we’re a totally bootstrapped company. We spend the money that we make, but we’re gonna turn into a SAS so we can take venture capital money and sell out and be beholden to investors instead of focusing on the features that are actually going to improve the lives of small business. Right. So that’s the e-mail that we sent out. And then it goes on and it’s written in sort of like a very like. Absurd but professional way. And so right until the end. People are like doubting it. They’re like, is this e-mail real and like just before, like the pieces click. We’re like April fools, right? And so the reason and I got tons. I got maybe, like maybe like.


30 replies to this e-mail across social channels in my inbox personally, which is the most that I’ve ever received, really, which which for an e-mail company might be a little bit embarrassing, but it’s it’s like compared to the stuff like just like hey, you know new feature release or whatever like that we typically send like this was.


I got some of the responses I got were like, Oh my God, I **** my pants. This was brilliant. This is the best ad for anything that I’ve ever seen in a long time. Like where some of the responses that we got. Yeah. And I’m like, why did this e-mail out of all of the, and I think I’m a pretty good copywriter. Like, no, I’m. I’m. I’m not terrible.


You are.

Why did this e-mail specifically work? Out of all of the emails that I’ve ever sent, it didn’t have an offer. There’s not really any value in it like there was a big red button that said, see the facial press release and it took takes them. To. The the video of the guy dancing. What’s what’s oh, my God. What is it? It doesn’t matter. But it was just a joke prank, right? Like there’s no call to action. There was really nothing of value in this e-mail. But why did it work? And I have a theory. I have a theory. So. My theory of why it worked is a couple of reasons. So the first thing that happened when people did when they looked that e-mail is they see Groundhog is going sass and that immediately causes a fear based reaction.

A motion, OK.

Immediate immediate emotion, immediate panic, urgency, fear. Second, they start reading the introduction. It sounds very professional. Right. It’s compounding like the it’s it’s settling in. But as they get deeper into the e-mail, it starts to become absurd. Mm-hmm. Right. And then that starts creating doubt, confusion. And then just before the pieces click, we do the old the whole April fools gag, which causes immediate relief and release of tension. And so there’s.

A whole.

Set of feelings and emotions that happen while reading the e-mail. And I think what really made it work is that it made people feel.

Yeah, yeah.

Right. Like like most e-mail is just really drivel. There’s no it doesn’t. It doesn’t cause feeling like when you when we send a discount code, people don’t feel it’s just like, OK, great. Thanks. OK.

Yeah, that’s another off. They’re off.

It’s just, it’s just I I. Don’t. I don’t feel anything. Yeah, as I don’t feel gratitude. So like, I know you’re sending that offer to other people. It’s not like I’m special. Right. So. Maybe the best way to elicit feeling from people in your e-mail marketing is not to scare the bejesus out of them. But then but, but what it caused me to do and it’s like, OK, so people felt and they expressed to me in the replies that it made them feel. And so feeling is important in order to get engagement. So I went back to all of the emails that I remembered that I loved reading. All the newsletters that I loved, I went back in my inbox and like I remember this e-mail, like I I what? And I went through it and like, why did I think that this was a great e-mail? Why did I engage with it? And I found several common themes among all of them. And I’m gonna. I’m just gonna. I have a list, and I’m just gonna go through them. Is that OK?

Yeah, go ahead.

All right. It’s like, why? Why did I personally think that these emails were great? And why do I know that other people also thought they were great so. Theme number one of a great e-mail. Is that I cared, and I mean like really cared. About the subject or topic of that e-mail, which seems obvious, people care that Groundhog is self hosted flat rate cost and open source. And so when I took that away, they cared about that. And when I read other emails like there’s a, there’s a. There’s a newsletter that I love to read. It’s called no mercy, no malice. Economist in new. Work and he basically does. Hot takes some like economy and SAS and big tech and a bunch of other. Stuff. And I find it highly engaging because I care about the state of the economy and I’m a business owner and this is stuff that I care about and either I’m highly engaged because I care about the subject. And I either agree with this take or I very much disagree with this take. And that’s a listening and emotion from me. So the so the question is, is the e-mail do people care? About the subject of the e-mail that you’re sending, would you care if you saw that e-mail in your inbox? Right. If you don’t, if you wouldn’t like if if you if you did not receive your e-mail and you wouldn’t care about it. Write a different e-mail. It’s like you can send it, but just don’t expect high engagement. UM. And so if you don’t know like, like, ask yourself, what do my ideal customers care about? If you don’t know who your ideal customer is, then there’s a bigger problem, right? And we have to deal with that. I don’t. Think we have time for that today, but. If you know your ideal customer, ask yourself what do they care about? If you don’t know, what do you care about? Because you should be your ideal customer and then you can write topics and subjects and content and send them to them that you care about right and people. Are typically. Able to recognize passion through the written word. Like when we when we read the great novels and the great books like they like that that wasn’t drivel that someone just spat out of Jat Jat T like we can recognize the passion and that’s why the great books have lasted for so long just because we can recognize that.

Of course.

Yes, yes.

  1. The second theme. Was that the outcome of that topic is consequential? Which is a little bit hard to to sort of put into words, but I tried and so and so. Basically. Either directly or indirectly. What happens as a result of the topic of the e-mail is going to affect me.


Right. If it’s Google policy changes, that is going to indirectly affect my business.

We have.

If it’s. Like we started being, like, very health conscious in our house, right? If I got an e-mail that’s like common household items that are leaching micro plastics into your water. That’s consequential. Right, like like I the the information within this matters in my day-to-day. And that was the 2nd theme of of all of the great emails that have read like that is consequential. Like, if I were to implement something or learn something from this, it is actively applicable. And you might be thinking, hey, like, you know, if I sent an offer to someone and they would implement our product, that would be consequential. But that’s too many steps to get there. Yeah, right. It needs to be immediately apparent. Like there has to be like immediate value there, OK. 3rd theme. It relates to my current situation. One of the I started writing a A Part 2 to my whole. I’m starting like a whole like e-mail is hard series where like I sort of just like. Blast thoughts in an. And send it out because I I as you can probably tell, I’m really passionate about this subject and I care, right. And I want other people to care because they should, because it matters to to being a good sender and practicing good sender habits. And one of the one of the things in in Part 2 that I’m writing is like. What we’re seeing is businesses, legacy businesses, they’ve been around for a long time, 15 plus years, they’ve been collecting people’s e-mail addresses and data for 15 years. They’ve never been regularly sending emails. And then, you know, they get into like the whole e-mail marketing, marketing, automation, spin and the like. Hey, listen, this is going to solve your. Problem right? You need to be emailing people right and need to be emailing people and then they upload their 15 year old list of people to Groundhog or whatever other CRM and sends that e-mail to that 15 year old list of people. 15 years is a long freaking time.

Tour tour.

It’s a long time. Peoples lives change. People move companies, people, situation change. People move. Countries like people start doing different things. People die.


Right, like 15 years is a long time. Six months is a long time in this industry.


And. If, if, if, if. You just plan on like sending an e-mail say ohh I have all these like high quality e-mail address that I collected at conferences and stuff is like no you don’t. That e-mail list is trash. I’m sorry it’s. This and what’s going to happen is you’re going to send an e-mail to a bunch of people whose live situations currently do not relate. To the knowledge offer value that you. Can provide them. And then what’s gonna happen is you’re gonna get blocked, Mark blocked to spam. You’re gonna. Get. Bad center of reputation. There’s just a whole bunch of bad stuff that’s going to happen, and so all the great emails that I’ve ever read actively related to my current life situations like, hey, listen, are you currently experiencing like a plateau in your business and you want to increase revenue? It’s like, that’s me. I would love to do that. That was a couple years. Ago, we’re good now, but it’s like. You you have to meet your people where they are. And if you’re just sending them stuff because you think you know where they are, that’s just, that’s just, that’s just not going to get you to. Where you want to go.


And it also has to be relatable. That’s the second part of sort of it relates to my current situation. You have to send stuff that’s relatable to their situation. And I have a couple of suggestions on how you can do that. You can use stories like if you have personal stories that you’ve been through like like. As an example, let’s say that you’re a business coach or something, which there’s a lot of. That’s cool. You’re a business coach and you’re trying to sell business coaching and you want to someone to sign up for business coaching and you’re going to say, well, here’s how I went from, you know, I my story started out like being homeless, like, that’s that’s actually a really common one that I see and someone.

Very much so much.

On your list might be at that point where they’re like I’m going to experience homelessness unless I can actually figure something out here and it’s like this is how I went from almost being homeless to, you know, being.


OK, right. And it’s like if someone’s currently in that situation, you can pretty much guarantee that they’re going to read that. And so obviously, all the stories that you have might not relate to everybody, but that’s OK we can talk about some hyper personalization stuff a little bit later about how you actually know where people are at. And so you can send them the right message at the right time. So you’re not just sending e-mail. To everybody, which is also not a good idea. UM and also like so much of the e-mail that we send is like so professional.


It’s very. Inoffensive. UM and pretty much everybody is sending professional, inoffensive e-mail. But. That ****, it just gets lost with like everybody else, right? If it all sounds the same, then none of it’s different.

And how do you stand you stand?

And. And and when it and and when we do that, we lose. Part of the language that the English language beholds on us is the ability to practice empathy.


Right. And and when we’re trying to. Relate to people. Right. Empathy is lost in the professionalization of the written word. And so whenever I write an e-mail, I just it. It comes from here onto paper. I don’t put it through ChatGPT. I don’t. The only thing. The only thing that happens is that my wife. Spell checks. It that’s literally the only thing that happens. And then and then it goes out because I want people to know. Who we are. Not who professional corporate brand is, because empathy is lost through that. Yeah. And it’s really hard to relate to people like corporate voices do not relate to to, to real people. People do business with people.


No question.

  1. The 4th theme, and there’s only one more. After this so we got we got two more. The 4th theme of every great e-mail that I’ve ever written has challenged a previously held belief or idea that I had. Being challenged immediately gets your gears turning and elicits an engagement response. That’s why subject lines like you’re doing e-mail wrong work because your brain will immediately respond. No, I don’t. I do even all good and I can prove it and I’m going to read to prove you wrong. Right. It’s like we like like the the, the, the, the mind is stimulated by confrontational questions. And ideas and belief systems, right. And so going back to like the business coaching example, right? It’s like that person who’s currently like, facing homeless. Their idea might be that that’s the only option. Right. It’s like it’s and and and the challenging belief might be that you can choose to do that or you can choose a better alternative, right? And they’re like, well, I don’t know, maybe that’s not. And it’s like and here’s how it’s like, well, OK, maybe maybe I’m wrong, like, but let’s find out, because they’re going to read to prove themselves.


Right. And then your job as the writer as the expert, as the person who’s value is to methodologically outline your case for why there is a better alternative.


Right, because people have their preconceptions, their notions, their ideas and and, and getting them to change is hard. And you have to, you have to do it in a. Methodical way. All right, so. You don’t always have to be so opaque, by the way. And like I said, like you’re doing e-mail wrong as like a subject like like, yes, it works maybe, but you don’t have to be so opaque all the time. You can be a little bit more subtle and some ways you can do that is just offer opposing effective. So like, let’s say you’re writing e-mail, you can include both sides of a different of a of a conflict like within that and then ask.


What do you agree with and then put some engagement stuff like maybe like a survey or link or whatever and ask people what they think, right people are. When you offer opposing expective perspectives like that, people are actually really like I want. I want this person to know. What I think. Right people. People love sharing their opinions, asking hard questions because the impulse is to answer them, right? That’s why, like like, you know, you know, like we did all the suggest allergy training back in the training business pros days like every, every like, 4th sentence was like a question. Because the questions engaged.

Of course.

Behind. Right. And then you have to make evidence like you can’t.


Just like spout. Stuff, right? You have to make evidence backed assertions that challenge whatever their previously held belief or notion or idea may. Be. Right. Or even the status quo. Like, if you have evidence to the contrary. Your responsibility is to share that with them for why they need X product or service or whatever, or why they just need to make a change that might not even require. Your product or service like my my through this I’m challenging the pre conception that e-mail is easy right which a lot of people they just load up their their newsletter and their latest post and they just send that out to get lost with all the other drivel that everybody else is sending out.


Yep. And I’m also making the assertion that what you’re sending out is probably drivel.

To first.

Right. And I don’t send out dribble, right. So you’re you’re like offended by that and then. But what’s gonna happen is you’re gonna. Analyze well if if people just stop sending or stop receiving my emails, would they even notice? Would they care? Yeah, right. You’re going to ask yourself that question, even if even if you don’t like the answer. Right. And so that’s what I’m sort of doing is like I am challenging your previously held ideas and beliefs about e-mail, not yours specifically, Rob, just like everybody.

Yeah, yeah, I know. It’s the royal yours. Yeah. Yeah.

Yeah, the royal you are right. The royal you are. Yeah. OK. Last one and then we can talk about some other stuff if you want or we can keep talking about this but. The the The the 5th theme of every great real e-mail that I’ve read is that it was entertaining.


Entertainment. Is a $2.53 trillion industry. That’s Hollywood video games. That’s YouTube. That’s podcast like that is the value of this industry. I didn’t make that number up. I got that from a very official website called Statista. I mean, you could just Google the value of the entertainment industry and that’s the number it will spit out, so. But that’s where I got that number and and and obviously, being entertaining is easier said than done. Right. It’s like e-mail is hard. It should be hard. And. So here, here are some suggestions that I have. To make your emails more entertaining. So. One of them is just. And and people are afraid to do this, understandably, but adding opinion. Into your e-mail.

Oh boy, yeah.

Ohh boy right, it’s like that’s very scary and I understand that.


Because you’re going to rub somebody the wrong way. Sooner or later.

So sooner or later, yeah.

In today’s world.

Yeah. Yeah. So I I sent out, but but so, so I all of this that I’m sharing with you. I sent out in an e-mail. And at the bottom of that e-mail I had a survey. It’s like love this e-mail. It was OK, hated this e-mail. Three buttons at the bottom. I had maybe. I I the the the ratio was 100 to 1. Yeah, but it did rub people the wrong way. Some one, some a couple people. Didn’t like it, which fair guess what? Those people are not my customer. That’s OK. You know if if, if if they’re not. If if if they’re if they’re not about it, they’re not about it. That’s OK.


Whatever I want to work with the people who loved this e-mail, because those are my people. Those are the people that are gonna get it, those. Are the people are gonna be easy to work with? Right. And if you’re just like corporate speak, that’s like flat lined appeals to everybody? It. Like like I get it like once you’re like a $10 million company, fine. If you’re like a solo operator or like a small business like be scrappy like you have, you can afford it because you don’t wanna work with everybody. You wanna work with. The. People. That get you that are on the same wavelength as you. That’s gonna make everything smoother and easier, right? And so if you like, there’s a reason that TV shows like the viewer still around. Right, because people engage with that well, love it or hate it like they they they engage. And your opinion doesn’t necessarily have to be like super controversial, like politics or something like that. Like maybe don’t. I don’t. I don’t inject politics into my emails. Oh my God, that’d be crazy, but. You can like add like I have opinion about e-mail and like I’m gonna put that in here because I think it’s hard and other people say it’s easy and I did. 3.

But the engagement factor is the big one. Like I can remember before your time, because you’re a little younger and I can say that there was a a sportscaster, but they named Howard Cosell E Sports cast for ABC did boxing. He did NFL football and there was a church in the states.


They used to auction off bricks and every time the cosal came on the. The the screen the person won the auction got so the brick and somebody asked Howard what they thought and he said I don’t care as long as they like me or hate me. Just watch me and engage with thing. I don’t care what they do. It’s that same old thing.

Yeah, yeah, it’s you got to be. You got to be. You can’t. You can’t. Did you watch Hamilton?


Right. What’s the guy’s name? It’s like, don’t tell them what you’re against or what you’re for.

Yeah, I forget his name, but yes.

What’s his name? The senator. I forget. Senator Barnes. Senator Burke. I don’t know. I forget. I forget, I forget. What? His name? I’m. I’m not an American. Right? I’m. Canadian so I don’t. But he’s like, he’s like, don’t tell people what you’re against or what you’re for so you can play both sides and on on the. On the flip side, Hamilton, the main character but and also like a real person.

I think.

Was like, well, I’m actually. I’m gonna stand up, and I’m gonna. I’m gonna stand for for what I believe in. I’m gonna let people know that. And he attracted people that were similar in his cause and in his thinking while the other guy who wanted to play both sides.


Fell into obscurity. Right. And it’s like. You know, plant your, stick it, plant your flag in the ground and say what you think.


Is is sort of my opinion on on the subject, OK.

So is my.

Language use language. We have this wonderful language with lots of different words that that we can use and then what we do is we put it through a corporate filter which removes all the fun language.


Yeah. And so the, the the subject line of of the e-mail of this e-mail that I sent out, which did fairly well, was e-mail is ******* hard.

Yeah, yeah.

That is not corporate.

No, not at all.


No, that is that’s that’s my voice. And that is what I shouted to myself in anger for after emails that I had previously written. Worked really, really, really hard on that didn’t perform well because they were filtered. And so I just removed the filter and I’m like, here’s what. Think you know ******* hard and people are going to look at that and they’re like they see corporate, corporate, corporate plane, like, like pared down inoffensive ******* hard. I’m like what? It’s like shock. And then, like, what? What what? It’s like, I haven’t seen that in a long time. Thing and then they they click into it and I’m like this is the state of it. Like, here’s what I think. And then like and I got a few responses. And like, this is so refreshing. Like, I like you had me until the end. Like, I was engaged like like I I feel how you feel about this subject. It’s like. But they needed to be shocked. Out of out of just their scan mode. Right. So we use the language now. You don’t have to swear all the time. There’s a lot of different words that you can choose from, but but consider being a little bit shocking in in in your delivery with the all the wonderful world words that we that we can use. Another way to be entertaining is to be unpredictable and and in my e-mail I say, predictably, predictability breeds boredom. Anyone who’s married knows that.


A little bit of humor, right? Which is suggestion #4 is be funny, which is, you know. Easier said than done again, but so many come like so many people are afraid to be fun. Because comedy is usually offensive. Like clean comedy is like doesn’t really cut it anymore. Like like like like I love Seinfeld. And that was pretty clean and like, that was a that was a pretty clean show. But if you’ve been to a comedy club in, like, the last five years, like, it’s not like that anymore. Right? Like, people people’s tastes have moved on from that.


No, not at all.

And so take take honestly, just take a risk. It would be my suggestion and you will probably offend somebody. And my opinion is that’s fine.

Yeah, yeah.

So what like so? What? What are they going to do? Like if they’re not a customer, right, like if they if if like if you’re sending emails out to leads and like they’re not paying you, there is absolutely 0 downside other than the fact that you might not be able to e-mail it again. But why would you want to cause they probably weren’t gonna work with you anyway. And if they weren’t, they probably would have been a great fit.

That’s right. That’s right.

So if you if if if you’re writing. E-mail and you think of something funny? Just take a risk. Put it. In and and the and the last. My last point. For the theme, which is be entertaining, is that if if you’re going to write an e-mail, it’s got to be energetic. Yeah, right. If you were to stand up and present the content of your e-mail with low energy, nobody would listen. So why would you write an e-mail with low energy?


Right. Say go drink a Red Bull and then write your e-mail or something, right? And that the your your energy is going to transfer into the content. It is amazing how people can perceive the tonality and the energy oozes out of something that gets sent over digital and they’re reading on their screen the the the. Our our ability to perceive that the sender is incredible and you should use that to your advantage like an like a corporate drivel is always going to lose to someone with.


Always. And you can stand out like that. So just to summarize. Uh, I just. I just to go back through it. #1 people gotta care. And if you don’t care, guess what? Other people don’t care. Straight up. The the subject, the topic, the outcome of that must be consequential. It has to affect them in some way and they have to understand that it has to be relatable and relate to their current situation.

Of course.

Has to challenge a previously held idea or belief, and it must be must be entertaining. And and and is it? It can include like if you just like get like three of those in an e-mail you have a really good e-mail. If you can get all five, you have a great e-mail. Yeah. And you will see the difference in the engagement of the people that you sent it to. Now it is one thing to write a great e-mail. It is another thing to send that e-mail to the right people.


So we can talk about that too. And if you’re thinking to yourself at this point that all this sounds very hard, that’s because it is. e-mail is hard, bad e-mail is easy, good e-mail is hard.

I don’t think. Hard.

And it should be.

Yeah. I think the biggest problem in e-mail marketing is people don’t send to the. Right, people, they. Don’t segment to us, they look at their list and they say. I’ve got a client who’s got a jewelry store and they like to send out their offers to everybody and I’ve been trying to train them to say no, no, no, no, no, don’t do that. If you know 10 people that came in and looked at gold necklaces, don’t send them a a diamond ring. Yeah, I’ll send them an e-mail on what to interest them, what they’re looking for, what they want. Because if you don’t tell them what they want, they’re not gonna open e-mail. To start with.

You’re absolutely correct. Send and and sending the right is. Is also about sending the right message to the right person at the right time.

Right. Hi. Hi.

The right time, the time aspect is more important than than people think. And so there, there, there, there, there are lots of ways to begin. Doing this. The. So. So I mean I I started earlier, it’s like a lot of businesses that have these lists of like 15 year old like they’re about 15 years old and they’re just sending an e-mail, the same e-mail to all those people with no segmentation. And then just it blows up in their face right that that’s just what happens.

I’m sorry.

The first thing that you should do is you should. You should remove anybody older than one year from that list and what you do with that, all that data you collected. I understand it cost you a lot of money, a lot of time, a lot of effort, but you cannot send anything to them. Just don’t even try what you can do is you can take that information and you can upload it. Google and you can upload it to Facebook and you can run remarketing campaigns and they will come back if they need your service. But their situation might have changed. They might have changed jobs. That e-mail address might go stale, and that’s actually a really big problem, like stale, Yahoo and Gmail addresses turned into spam traps.


And that’s not great for anybody, especially deliverability. And like if you do that, you’re going to get booted off your sending service, which is not great.


So just anything older than a year. Get rid of. It Every month we delete well, we don’t delete but we unsubscribe emails. That are not customers leads that have not engaged with our content in over a year either.

I have over 3000 like that, Adrian.

Yeah. And we we do that every month we we remove them if they haven’t been with us in, in over a year. If they haven’t opened an e-mail they haven’t clicked, they haven’t visited the website, they’ve just been inactive, they’ve just. Dropped off and we’re like well. We upload them to Facebook remarketing and if they come. Back they come back.


That’s that’s really all we can do, but continuing to waste resources on this person. Is not effective and it won’t be so that’s. That’s the first thing that anybody’s got to do. The second thing that people got to do.


Is for the people that are left, right, the people that you have, we have to collect some information on them. We have we have to do a little bit of digging. We have to do and and and if you haven’t been doing this from the start it might be very difficult to start to get that. Data from them. Depending on how invested or how they engaged they are, there’s a couple ways you can do that. You can send an e-mail with like a survey in it. It’s like which best describes you. I’m starting a business. My business is old my. Business is failing like whatever and then they. The button. And then you know something about. Right. And then you can just do that every once in a while and continue to build up your information. If you are, you know, doing lead Gen. right, if you’re collecting leads or people are signing up for stuff, it’s probably a good idea to get that information at that time. So maybe after you collect that e-mail address, you immediately dropped them on the page where it’s like, which best describes you and they they tell you. What their current situation is, and when they tell you what their current situation is, guess what you can do. You can send them something that immediately relates to their situation. Right. Like I we we have a we work with a few different types of businesses. We work with small businesses, we work with agencies and we work with nonprofits. Those are sort of like the. Three main verticals of of. Business that we work with, we do not send the same message to agencies, nonprofits and small businesses. Those are three different segments. We send them different messages that relates to their situation. An agency. Probably has different problems, which is why they’re communist than a nonprofit, right? Nonprofit are using nonprofit specific software. They’re poor. Usually they have some other growth pains, and then agencies, they’re coming. They’re flesh. They’re not poor, they’re fine. But they’re having problems with scalability. They’re having problems with those. So we’re going to tackle those different problems. Really.

Yeah, makes sense.

And so we when we collect that lead, it’s like we put them into that specific bucket, so. If if you’re doing car insurance right, a good question to ask might be do you already have your car? Are you in the market for a car? How old is your car? Right? Because you might have different, you know, packages or or offers or information for these different people. Like if someone says I don’t have a car yet, I’m just looking, then you might want to send them. A guide on how to pick the best car for you. Like that seems kind of obvious. That doesn’t immediately get you the business, but it does create a good feeling like. Well, I want to know how to get the best. Yep, right. So that person needs a different level of attention than someone who says I have a car and they need insurance now. Like, all right, well, then, get on the phone or something like that. That, that’s. That’s what we qualify as a hot lead. Like you might. You might want to do something. And if they have, like, an older car, well, there’s also. Like legus? Or there’s a classic car insurance and stuff like that, and that might be like a different person that might not even be your company, right. And you might save yourself a lot of work investing in the lead process only to discover that this person has a classic. Car that you’re not going to support.


Right. That’s called pre qualification.


And so once you like start collecting this data, you can segment your messaging and in the customer journey you can discover what is the right time. So for a hot lead, the right. Time is now. Yes, right. But for someone who hasn’t. Bought a car. Yet, right. What do you do in that situation? Right. Do you do you try to sell them insurance now? Probably not.

No treatment.

Like guess what? That’s wasted effort. They’re not going to buy and more and probably they’re like I don’t have a car. Why are you trying to sell me insurance like and that just that just turns them off and they’re gonna go somewhere else. Right. And so the art is to continue to send them education to the point where they get a car and then they come back and that is the point where you do a little bit of long term nurture. You do a little bit of follow up you know and you don’t and you’re not too pushy about it like you mentioned like you know you just got glasses and like every day and that might be a lot. Right. So it’s just like a little drop in like maybe once every like 3 weeks like hey, just checking in to see like how your car purchasing process is gone in the event that you want to to to start looking for insurance for a new purchase like you know just schedule a call with us here link to a booking calendar or whatever. Here’s a little bit of more information like here are the cars that are currently getting the best insurance rates right? So if you want to really, really great insurance, right. These are the cars that you should be buying, something like that, right? It’s like the the be targeted in your messaging. I cannot stress that enough if you’re just sending the same message to everybody, you’re it’s just.



It’s just not the best strategy in my opinion.

I think your opinions are real valid one and along along that wine. And I don’t know if you’re going to go there or not. One of the things I always say to people is never, never, never, never, never sent from a do not reply address whatever you do and big business loves to do that.


And you know what that screams of? Adrian, you don’t wanna engage with them.

Yeah, like. Big so, so, so, so the the the difference between me for example and let’s say HubSpot, right, yeah, there’s a little bit of a revenue discrepancy there. We’re working on it, but.


The one once you get to that level. It it, it stops being about relating to the customer and the lawyers and the accountants take over and it starts to become about liability.


Right, the do not reply address is a liability. Because if someone replies to that e-mail and and and and they have something to say and they’re expecting a response and they’re not going to get one, that is a bad customer experience.


And potentially A liability issue, depending on the subject.

Very bad.

And so and so the do not reply address is is a method to to to prevent that because. I I I can’t like HubSpot must e-mail millions of. People. Right. And Can you imagine the the number of responses to that so? To an extent, I appreciate what it’s for.


Like. But most people are not HubSpot. Like if, if if you’re supporting less than 10,000 cuz. Nurse, there is absolutely zero reason to have a do not. Reply e-mail. Right. Because the engagement that you’re gonna get from 10,000 people is just not going to be that much, right. And if it is, a lot guess what, you should probably just have someone to take care of that, like, assign it to your front desk, assign it to support, assign it to whoever to just reply because the customer, because businesses that engage do better than than businesses that don’t. And so. To a degree, I absolutely agree with you that the do not reply is a method to not engage, but for a for like huge organizations, you can understand why.

That’s a different moment.

It would. It’s a different ball game than than small business, but if you’re a small business. Do not. Have a do not reply. Yeah, just don’t do it. Just engage with people like all all the emails that I send, guess where they go. They go to my personal inbox because I love to read what people have to say and and I use that to to improve the messaging to improve the targeting to to like to to come up with content ideas. Guy in in this e-mail where I have like I hated this e-mail. It was fine. It was great. They go to a forum like what would you like to hear about in the future and people just give me ideas and guess what? That’s a highly relatable topic that somebody’s gonna care about. And if somebody cares about it, chances are more people will care about it.



So much so much so.

We’re just gonna let that sit for a. Second, with people.


I think I think the big word in there is there so.

Where do you want? To go from here.

It’s so hard with the days of AI right now to get good emails and it seems all these marketers are jumping on AI and I’m guilty of it too. And I’m sure you are at times too, right? Go to your favorite AI.

Ohh, we’re all guilty. Ohh super guilty for sure.

And you say spit me out an e-mail about this and it was funny. I was saying to somebody yesterday before saying I had this conversation coming up with you. And I said, do you know what bugs me? I got 15 SEO proposals in my inbox and I swear they all came out the same. AI every last one. And there’s no. Personalization in them, that’s a big deal. You know that and I. Know that right? And there’s no nothing, nothing. And it’s all we can help you. But did you do any research about what they do before you offered to help me and I and somebody probably took some keywords, dumped it in the chat GP and said here you go.

Yeah, I don’t. It must work, otherwise they wouldn’t do it. So I it must work. It must just be a numbers game. And they like, they latch on to an unsuspecting small business owner that they spun up a Wix site. Right. And they’re new and they don’t know any better. Right. And then that’s that’s just right.

Yeah, I know. Yeah. Know.

And and that’s why inboxes are are are locking down. That’s why they like all the new Google compliance stuff Apple Mail privacy protection. They’re just the there’s a constant tension between marketers and inboxes because the line.

No question.

Between marketer and spammer is very thin and very Gray.


Like so, we’ve been using the example of a 15 year old e-mail list with a few thousand people on it and someone up so that they just send an e-mail. Do you know what that person is? They have the best of intentions. They probably have a legit business. They probably do everything right and then all they do is they just upload the list that they worked very hard on and spend a lot of money to collect and then send an e-mail. And guess what that person is? It’s not a spammer.


Because they’re not practicing. Good e-mail sender habits, which is you should have stuff that relates to the person you’re practicing. COI confirmed. Often you are actively removing inactive people from your list, right? And and, but because people don’t know what they don’t know, but what you don’t know can hurt you. It can.


And so. My my message to anybody who’s who’s, who’s been on this, who’s who’s listened to this and like, Oh my God, that’s me. And I hope, I hope, I hope I challenged your your your previously held beliefs and ideas about e-mail a little bit and you’re like maybe I should make a change I I I I I invite you to do a lot more research into this topic. We’ll go learn about and we and and if you want to go to the Groundhog blog. To do that, we have all of that there, like all the Apple Mail privacy protection and all the good sender habits. What you should be doing, how to send good e-mail and how not to send bad e-mail, right. Because again, sending good e-mail is hard. Sending that e-mail is easy, and so if you see someone on Twitter, whatever sending, sending e-mail is easy. You know, I would, I would. I would immediately be skeptical. I mean, I’ve been into this industry for a long time. That’s my 2 bits. Those are my 2. Cents. Yeah, I and I and.

I agree with you know, it’s funny. People like to send cold emails occasionally, which I I question how much they’re worth. And the problem with cold emails. Forget the CRM. Right let’s. You talk about stripping. Is I don’t say to people if you’re gonna send a cold e-mail, do yourself a favor. Don’t send it from your domain where your e-mail list is coming from. Please and thank you. Thank you. Yeah. And the reason for that is. If those cold emails get marked as spam, then you don’t compromise your main domain. I know that sounds like an underhanded marketing marketing tip, but I wouldn’t do it any other way if I was going to. Now I don’t send out cold emails, so yeah. Think about that.

Marketers ruin everything.


You’ve heard that before. My like dad. My my dad says that all the time. Marketers, marketers ruin everything and.

Of course it is.


That’s why that’s why, because, like marketers are basically hackers and like the loosest sense. Because any way that they can exploit or find a loophole to deliver their message to a recipient, right, it’s like they’ll find one. And that’s why the inboxes are like clamping down on all this stuff, right. Again, the line between marketer and spammer is very Gray and very thin.

Yeah, fine.

Yeah, I I have. I have mixed thoughts on. Cold e-mail. Nathan Berry, you know who Nathan Berry is. Right.

Very much.

Yeah. So when when when he was starting with convert kit right, I have that right? Yeah I do.

That is 600.

Yeah. So when he was starting to convert kit, he went on and I and I read this Twitter thing because again, highly relatable because he started to see our own company. I started seeing company, right. It was entertaining. It was packed with value. It was consequential. Right. So I read the whole thing on Twitter. Back when it was Twitter and. He was like the way that like, like he was like convert kit was floundering and I didn’t know what to do. And so I just started cold emailing people.


And I was like, I will and he and. But but what he did was different than what most people do for cold e-mail. He went into his the the inbox and he researched people that he thought he could.


Yeah. And he didn’t just buy a list from built with or something, which some people do. He he identified people that he thought he could actually help that were on his list already. That might have been, like, tangentially related from conferences, whatever. And he went and he looked at their site and he made an offer. I mean, it’s like I I think we could really help you over here, convert it. We can reduce your bill by X amount and we’ll actually switch you with a free migration as the offer right, which is high effort for him. Right, that, that is that is a high level investment that he’s willing to make in their business, right. And all they really have to do is say. That’s right. And that’s a low effort for them, right? And that’s the difference between most between that kind of cold e-mail and most cold e-mail. It’s like it was highly personalized, right? It was. And it was actually coming from him. He wasn’t using like, a cold e-mail software. He was just uploading list and sending it out an e-mail blast. He was like.


Typing out each e-mail individually after doing research right, which most people don’t do, and you do that and that takes time. And guess what? That’s also hard, right? Sending good e-mail is hard.

No question.

Hi. Right.

It just is, but guess what? It’s also worth it. Things that are hard are usually worthwhile.


Right, nothing worthwhile is easy. Nothing. I want you to tell me one thing that’s worthwhile. That’s easy. It’s just not.

I always say the harder it is, the more worthwhile it is. At the end of the tunnel.

Yeah, it’s. Yeah. Yeah. So that’s so. So that’s if if if you’re doing your research and you’re you’re you’re making a a legitimately valuable offer.


That you can coherently explain in a few very short sentences in order to get someone’s attention right. That is high effort for you and low effort for the person on the receiving end. That might be might be a good example of a cold e-mail, but all these SEO audits. We all know that’s ********.

Yep, Yep.

We all know. Like what? What even is an SEO audit anymore? It’s like we have so many free tools like we have like so much knowledge on on on search engine optimization and guess what? None of it freaking matters anymore because the 4th organic search result is always Reddit right? So like it doesn’t even matter anymore.


Yep, Yep.

Create. Valuable content that people care about. And provide a valuable service. That is consequential. And that that is, that is the formula.

I agree. We’ve had John before. We’ve talked about Groundhog. What changes have you made to the product that make it easier for somebody to run an e-mail automated?

Well, keeping it, keeping it in sort of the the, the spirit of the subject so far, which is sending good e-mail. I’ll, I’ll. I’ll point out some of the ways that we empower small businesses to make it easier. It’s still hard, but easier to send good e-mail. Confirmed opt in. Stuff is is is immediately top of mind. There’s a lot of GPR, there’s a lot of castle canned spam like there’s all these different privacy regulations and we’re on the pulse. We’re on the bleeding edge where we have we have tools.

Is a Muslim.

That implements and automate the process of collecting that information and that consent, and we even like it’s even recommended now to start like collecting that consent on our regular basis, because if people consent and they’re keeping their sort of status fresh, you know that that is a high value person on your list and that you can continue to send good e-mail to that list, right.

Of course.

So we’re just making it easier for for people to to maintain a high value list and to to remove. Move. Leeches basically, to remove things that devalue the list. So we have lots of reports and lots of filters to remove inactive people from the list and to catch spam and to do all those things we have like integrations with like 0 bounce and stuff to like filter out emails and stuff do e-mail validation. In terms of the actual like. Design design process of emails by far the largest thing that we’ve done in in recently in November last year, we launched our our new drag and drop e-mail editor which is.


Chefs kiss. It’s phenomenal. It’s really good. I’m really happy with it, actually. We we’ve been working on this e-mail editor for three years. OK, so we started. We started off with with trying to do like a like a Gutenberg implementation of the e-mail editor and. And there’s a couple other people.


That are doing that like like newsletter glue. Does that and fluent CRM hazy Gutenberg e-mail editors? Well honestly we just got frustrated and gave up. Yeah, we’re like, screw this. We’re gonna build our own. And then we started building our own and then we weren’t happy with the way that we built it. And so we started. Again, and this most recent time that we started over, we actually ended up something that we’re very happy with. It’s very fast, it’s mobile responsive, it’s got all the style controls. You can honestly like if you go to like be free or stripe or any of those like sort of brand name, e-mail designers such that you export HTML templates. You can do all that within our e-mail editor, plus it’s got a bunch of like WordPress focus features like inserting posts automatically into newsletters and. It’s not. It’s got short code support. It’s got HTML blocks, it’s got it. You know it automatically pulls links from WordPress, so the links autocomplete when you’re writing, it’s just, it’s just phenomenal. It really is and.


The other thing that we do is we automatically convert. So if you’re writing your beautiful HTML e-mail with columns and font colors and all that fun stuff, you only have to write that e-mail once, and it also automatically converts it into a context rich markdown format. In plain text to send out the. Plain text version.


Of that e-mail, which is the best practice for deliverability, is if you’re sending HTML emails to also send a plain text version and it’s context rich, so it has like all the links and stuff in it, and it’s completely automated and it’s perfectly readable every single time, which is was super important because the way that we used to do that was just like. Rip all the HTML out and then. Send that and that’s just not great cause. Readable. But we took a lot of care with with developing a a beautiful conversion process, so you only have to write the e-mail once. You don’t have to write your own plain text version which you used to have to. Do if you wanted to be nicely readable. That’s probably the biggest thing is if you want to send that e-mail, it starts with being able to write and design good e-mail.


And our tool makes it easy to do that.

It does. How is what’s on the road map down the road. Can you share anything? You’re working.

Yeah. So we’re working on e-mail archives, so you can share a public link like MailChimp to see the emails that you’ve previously sent. So you can select a.

It’s successful.

Or add an e-mail to a campaign and they can share a link for that campaign and then it shows all the previous emails in that campaign, which is kind of. We’re working on updates to our calendar add on to make it much more beautiful team calendars or updates to our companies. Add on to make the directory more usable and to also make the search, filters and custom fields accessible as well to for companies. So we’re doing a lot we’re doing.


Doing a few fun stuff if anybody is interested in what we’re actually currently working on, you can go to Groundhog dot IO feature requests and all that information is there. We have it on the website, you can see what people have asked for, but we’re currently working on what’s planned, what’s in progress. So we’ll check it out.

What is your most requested feature at this point?

Well, well, it was a better e-mail editor, but. We solved that.

You saw that one? Yeah, that one was.

We solved that one, yeah.


That’s what it was. Probably the big ones now are related to calendar, which is what we’re currently working on.


Yeah, this has been a journey, Adrian for you. I mean, those who don’t know your background knows your dad’s company was an infusion soft partner. You were probably. And correct me if I’m wrong. Warren was in training business pros. The number one infusion soft reseller in. Ended at one time I believe.

We were, we absolutely were. I was. I was an infusion soft certified partner as well. I was doing form lift which was like a.

Yeah. And then you make.

Which is currently a form plugin for Infusionsoft that connects Infusionsoft to WordPress in a more beautiful way through forms.


Yeah, that’s so we started out there a long time ago. Like the first time we were talking the first time I spoke at a word camp was in like 20-17 and then I had started in WordPress developing WordPress plugins a couple of years before that. So I’ve I’ve been.


Doing this for a while.

Yeah, it’s been. It’s been your journey, an amazing journey. And coming out there, Canada and coming out of local, you’re pretty local to me. I would say no. And and there’s a lot to to be thankful for there. I think if somebody’s looking for good Sierra. Honestly, go check out Groundhog. Go talk to Adrian, send him a tweet ad. You do answer all your DM’s generally.

I answer most of them.


I try to answer as many as. I can I do?


Now what you need to do is get that little plush Groundhog in a merchandise store, and you’d be all set, you know.

That’s an in progress. We’re gonna have. We’re gonna have some plushies out.

I want one. I want one, yeah.


Yeah, I’ve been saying that for a while. I won’t let so you know, customer here. So there you go. If somebody wants to talk to you about Groundhog e-mail marketing. The best way to. Address a tweet or.

We we got, we got all the channels we got, we got Groundhog on Twitter, I’m on Twitter. Adrian. Toby, you just look me up. Groundhog dot IO is the website and you can e-mail me Adrian at Groundhog dot.


Well, if you look for us, you’ll find us. We have live chat on the website. We’re happy. We’re happy to chat. I’m happy. To chat with you.

Yeah, Adrian, as always, thanks so much. And we will see you soon. I’m sure. Have a wonderful day.

Alright, it’s been fun. Thanks for having me.

Appreciate it. Thanks

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