Episode #8 – Jon McCulloch and His ‘In-Your-Face’ Strategy To Making More Sales With Email

by John McIntyre

Jon McCulloch has spent the last 6 years enjoying the fruits of an “email business”.

In other words, send emails.. make money.

In episode 8 of the Email Marketing Podcast, Jon shares what he has learned. He’s a bit of a cowboy when it comes to email. I’m on his list and I’m shocked if his daily email doesn’t have at least 3 f-bombs in it.

So yah. Jon has email chops. Listen to this episode and find out how he does it, much to the chagrin of the chaps he pisses off (inevitable, so Jon says).


In this episode, you’ll discover:

  • What he’s learned from 6 years in the email marketing biz (counter-intuitive truths about what it really takes to sell with email)
  • Jon’s “Fuck You” strategy to selling with email (and why he tries to piss people off with every email he sends)
  • How to use boring daily events to make more sales via email (nothing bad ever happens to an email marketer)
  • Edgy and in-your-face techniques for trimming the fat and eliminating bad prospects from your funnel (I LOVE this part of the interview)
  • Jon’s aggressive strategies for discovering his audience’s problems

Email Marketing Podcast Episode 1


Intro and outro backing music: Forever More by CREO

Raw transcript:

John: I’m very careful about whom I let it. My bullshit [inaudible 00:00:10] is very, very strong.
Hey, podcast listener. You’re about to discover insider tips, tricks and secrets to making more sales and converting more prospects into customers within our marketing. For more information about email marketing podcast or autoresponding guide, go to drop dead copy dot com slash podcast.

Hey everybody, it’s John McIntyre here, The Autoresponder Guy. It’s time for episode eight of the email marketing podcast where we talk about top tips, tricks and secrets for making more sales and growing your revenue with email marketing.

Today, I’ll be talking to Jon McCulloch about what he’s learned from six years in the email marketing business including his f-u strategy to selling with email and why he tries to piss people off with every email he sends. To get the [inaudible 00:01:01] for this episode of the email marketing podcast, go to drop dead copy dot com slash e-p-8. The email marketing podcast has another five-star review.

Matt from the United States says, “John is bringing in top guests with actionable content. He pulls the top tips and tricks and secrets from each guest and makes sure that each podcast gives you value and help you increase conversions. Great listen.” Thanks for the review, Matt. I really appreciate all the reviews, guys. Remember, if you want to leave a review, go to drop dead copy dot com slash podcast.

Before I talk to Jon, I got one more thing I want to tell you about. It’s about an email mastermind. Instead of hiring me to write your emails, what about getting me to coach you? Imagine joining me and 10 other people in an email mastermind. Some of the benefits include, since you’re writing your emails, they’ll be in your voice. You’re learn how to write emails from me, someone who writes emails for a living. You’ll network with other business owners who have similar challenges and it has the power to transform your business.

Here’s what I’m thinking. Ten people, one or two weekly calls, a forum for discussion and weekly homework. The idea would simply be to make more sales via email. If you’re interested in something like this, go to drop dead copy dot com and sign up to the email list. I’ll be showing more about the mastermind and opening the doors in the next few weeks. If you have any ideas from the mastermind, send me an email at john at drop dead copy dot com.

Now, let’s go to talk Jon McCulloch.

John: John McIntyre here, I’m here with Jon McCulloch. Jon’s another email marketing guy. How are you doing today, Jon?

Jon: I’m fine, thank you, John.

John: Good to hear that. The idea here, I’ve just been talking about is to talk about email marketing and to drill down to the specifics of what each person does. We’re going to talk about what Jon does specifically with his list to make sales to do those kinds of things. As you find out in a minute, he gets pretty edgy with the some of the stuff he does.

To begin with, let’s just start something real quick. What do you like about email marketing, Jon?

Jon: To me, it’s quick and it’s easy and it’s cheap. Those are the advantages. When I say it’s cheap and quick and easy, I don’t want people to think that that is a major selling point in the sense that they are just the icing in the cake. To me, what’s really powerful about email is it’s personal and it’s immediate. If I could do that, if I could make it personal and immediate and it was expensive, I would still do it because marketing and advertising it [inaudible 00:03:00] cost as an investment. As long as you’re getting positive ROI, you should be prepared to spend money on it.

I don’t want people thinking that email marketing being cheap is really good reason for doing it. If it didn’t work, like social media marketing for instance, is cheap and doesn’t really work very well for most people. [Inaudible 00:03:55] something cheap and easy for what we’re doing, but that’s what I’ve observed.

What I really like about it is it’s immediate, it’s very personal and of course, it works as well. It means you can have ongoing dialogue with people from day to day and as you know, you get my emails, I’ve got an ongoing story for instance going on in my past about my puppy Jack Russell in the racks that I’ve got in the barnyard, things like that. It’s ongoing dialogue, quick and easy and immediate, very personal.

John: You’ve been doing this for a long time, right?

Jon: Yes, probably with a break of about maybe nine months to a year, I’ve probably been doing it for six years or so.

John: It’s consistently writing emails, doing emails business and that’s been the primary thing. You’re one of this, the hallowed email business where you send emails every day.

Jon: Yes, pretty much. The thing is with lead generation, I will do direct mail and pay per click and Facebook advertising and all the other things, but once people get into my list, the two main ways I sell to them are via email which is by far and away the most popular way for me selling stuff. Also, when people do and buy stuff from me, I have a physical address for them then I get direct mail as well, not as much as I should because I’m lazy. I should do more direct mail, but email marketing is too much fun.

John: I know you do daily emails, Ben Settle does this too but you were saying a moment ago you that you do this a bit differently. Let’s start off and tell me, why daily emails? Everyone I know would be, “That’s going to piss people off. I don’t want to write that many emails.” What’s the big deal about daily?

Jon: The thing is, you are going to piss some people off. Of course you are. What I do is I make it very clear up front that when people join my list is, “You are going to email daily. If you don’t like it, fuck off,” it’s simple as that. I also put things about my politics and my complete, utter not dislike religion, but utter disdain for it. I’m very upfront of what they’re getting into. I tell them, “If you really don’t like that, you really don’t want to be on my list, so get off it.” Very few people leave immediately. Some will leave quite quickly because they realize that this guy actually is what he says he is.

Otherwise, I’ll play it very close to the knuckle. I do it daily and there’s ongoing stories and I keep it current with current events and it’s an ongoing dialogue. If I send out an email and I get responses, I will then follow those responses into the email the next day or a couple of days later.

I would in a short period of time, say a month, people will start to get a picture of me as a human being, as a person. I put my personality in there and they know me. One of the things I think I’ve written is in 52 series emails, my 52 days email, when people meet me in the flesh in events, say or when I’m helping out one of my clients in an event presenting or things, one of the most common things that people say to me is, “It’s just like I know you already because I’ve been reading your emails.” People tell me that totally I know that I’m doing something right.

John: How do you come up with these daily emails? I’ve wondered about this before it’s like, how do you have enough information to continue sending emails every single day, day after day after day?

Jon: I knew you were going to ask me this. I don’t know, sometimes I ask myself and I don’t know. There’s always something going on. There’s a saying that Ben and I, because Ben and I are buddies, Ben Settle, and there’s something we both say, “There’s nothing bad ever happens to an email marketer.” I think that probably comes from my theory originally.

Anything happens in my day, for instance, tomorrow’s email or was it today I don’t remember, it was today’s email that went out this morning from here, was about I got 38 pens saving in the local supermarket [inaudible 00:07:57]. The woman was telling me if I should be really, “Great, 38 pens.” I was lamenting that there are actually people out there who would give a shit about saving 38 pens.

Then, at the same time or not long afterwards, I passed two [inaudible 00:08:18] of , overweight, smoking [inaudible 00:08:17]. They were complaining at [inaudible 00:08:20] income. That’s just two incidents that allow me to weave in my own fairly offensive politics in saying, “People can smoke and [inaudible 00:08:29] on benefits. They’re being paid too much anyway, I mean, they shouldn’t get any.” I know that that’s going to offend some people, which is great. I don’t care about that because I got about a dozen emails this morning saying, “Yes, rock on John. I like that.” They are the people I care about.

That’s just one idea that just came from [inaudible 00:08:45] into my day. Another one probably tomorrow early next week, sorry, likely this week we’re on Tuesday, aren’t we, I spent a brief time this morning at my ex-wife’s picking up the kids and send them to school and reminded me I why I was so glad to be divorced, to be quite frank. That will be woven into a story about if you don’t like the situation you’re in, you can do something to change it.

That’s how easy it is to me. The last couple of weeks I’ve been traveling, been out of town. When a [inaudible 00:09:22] hung in my office in Ireland, I got on my bike cycling every day for an hour or two hours depending where I’m working out. I do a lot of thinking on my bike. My bike is actually owned by the company and I write it off it as a tax deductible. I would argue this with the Revenue because to me, my bicycle is an extension of my office. There’s enough evidence in my daily emails about what I was thinking about when I was out on my bike today and there’s enough evidence in my daily emails for me to present to the Revenue in case and say, “Look, here’s the evidence. I actually do this. I’m not just saying I own this bike but the company for a tax dodge. I work when I’m on my bike.”

If I get ideas in the shower, people just say things to me, I’ve got little post it notes stuck everywhere, just single sentences that people say bring out their ideas. The thing that I think matters, is if you don’t understand your subject, all the ideas in the world or opportunities for ideas in the world like walking past the [inaudible 00:10:33] or the north of it, might not register with you. If you understand your topic like I do marketing to small businesses, everything can be turned into an opportunity to send an email.

I don’t know if I’ve answered your question or not. It’s a little bit like maybe saying to a fish, “How do you swim?” [Inaudible 00:10:47] in asking the fish, he’s always done it.

John: I think the one thing that people need to take away is that there’s no magic secrets, though. You sit down and write and you come up with stories and you just sell them on the benefits or whatever you’re trying to sell and grab them with your stories and there’s stories every single day.

Jon: Another source of ideas that I get, I use these quite a lot as you’ve probably noticed and the [inaudible 00:11:] one because I’ve just had a nice one come in. When people in my inner circle have a success, I will use that as an email and say to people, “Look, if you don’t look in the inside, this is what you’re missing in your business. The only way to get this kind of result for your business for many is to join me in the inner circle.” I’ll probably get a couple of those, maybe one a week, couple of weeks, something like that. There’s always something to do, there’s always something to write about.

John: You were talking a moment ago like soft information versus hard information. I’ve just been reading some of Ben’s material and he does a lot of the soft stuff where he tells you what to do but not how to do it, but you to things differently. You give them more hard, actionable information. Why do you do that?

Jon: That’s a good question. I don’t agree with Ben in everything and that’s one area I don’t always agree with Ben, particularly as to how much to give away. Some people, there’s a truth thing there. They want to know you can do what you say you can do. A great way to get someone believing, if you like, is to give them the tools to do it themselves. That’s probably a [inaudible 00:12:04] but there’s some really powerful things I write from time to time.

Here’s a good one I’m give it to people now. Listen to this, “If you’ve got no business, but you’ve got X customers, one thing you can do is pick up the phone and ring them all and just say to them, ‘What do you need that you’re not getting,’ and listen to them, or alternative question is, ‘What’s your biggest problem in your business right now?’ Just listen to the answer, don’t try and sell anything.” Then, call them back a couple of days later and say, “Hi Fred. I was thinking about that phone conversation the other day and I’ve thought of three ways that are probably going to help you solve that problem you told me about,” or “Three ways that can give what you told me you’re not getting.”

I know people who’ve done that. It costs nothing. Every single person who’s ever done that has gotten business straightaway. I’ll often throw that tip and people do it and think, “Jesus, this works and if he’s just giving this away what else does he have under his little boat head that he could do that I could pay for?” Ben and I have got different views on that, that’s fine. We don’t have to agree on everything, we’re not married or anything.

John: That makes sense. You do five days a week on your newsletter. Should some people be doing seven days?

Jon: Yes, as interesting that is, my general rule of thumb is if you are selling B to C, you’re probably one of those seven days a week. If you’re selling B to B, might be five. That said, literally just this way because talking to a client of mine, a very big shot in the UK in the small business marketing area, and he says he’s been having really good responses with satellite emails to his business to business list.

From this week and this is another tip for everyone kind of walk to walk, I’m an implementer, so from this week this Saturday coming, I’m going to be emailing six days a week and I’ll see what happens. The theory is that on a Saturday, often people often are pissed off, “This is Saturday and I hate my job and I’ve got two days off.” If you give them something that’s going to make their lives better, they’re in a very receptive frame of mind.

John: You do this [inaudible 00:14:21] because I’ve seen people and I’ve done this before when I’ve written for people. I might write ten-email autoresponder that goes out for a month every three days or something. It sounds like what you’re suggesting is that you just never stop emailing people, you’re always sending them something.

Jon: Yes. What I do though, on this [inaudible 00:14:48] technical thing down to deliverability, I’ve got a rolling process, 30-day sequence or process. Anyone in my list, if you’ve not replied to an email or clicked on a link or opened it that can be registered by the system I prefer a link click and there is some [inaudible 00:14:55] in there, if you’ve not shown me or my system that you are reading my emails or responding to them in some way or interacting in them in some way, you get my email saying, “Hey, you’ve not responded,” or “You’ve not acted on something in 30 days, if you don’t do it in the next 10 days, I’m going to kick you off.”

Ten days later, if they have not clicked the link or replied or responded in any way, they get removed. Most people won’t have the balls to do that because it’s like, “This is my list. I can’t be mean to my list.” It’s not that many, “If you’re not listening to me, I don’t want you on my list because you’re just dead weight. You don’t open your emails.”

If I’ve got a thousand people on Google and my Gmail address is and Gmail says, “Hey, this guy is sending all these people in our email system with his emails, but they’re not opening them, he must be a spammer.” It’s not a case that dead weight in your email is just harmless, it’s actually telling those people in the Gmail, Hotmail or Outlook, all those people that tells their system, “This guy is sending stuff that no one is interested in, I’m giving a him lower rating of importance.” It’s a good thing to take off the dead wood from your email list even though it’s counterintuitive. You may have paid for people to be there via paid advertising.

John: I was shocked when I had an email from Mind Valley, that was about two months ago and I was in one of their autoresponders, but I stopped opening the emails and they sent me an email just saying, “You’ve been unsubscribed.” I was blown away.

Jon: It’s great positioning as well.

John: Yes, it makes you seem so exclusive, so selective.

Jon: There have been various things that I’m experimenting with in the next year or so. One of them is actually having an email list, maybe secondary to my free one that you pay to be on, not one bit a lot of money, might only be $5 a month or something, but I’m just going to give that a go.

John: I think you might have success with that because once someone’s given you $5, they’re more likely to give you money for whatever other products you have to sell them.

Jon: Yes. A buyer is a buyer is a buyer. I’ve got a group in my list who’ve been with me for at least seven years if not longer. My buyers buy everything I do. I could probably [inaudible 00:17:01] for that buyer. They might not buy anything else after that, but they would buy that.

John: Everyone’s probably picked up by now that you use a lot of bad language, dropping F bombs here and there. Obviously, you don’t really care about these subscribers you piss off and make them unsubscribe, but do you ever worry that you’re losing sales from these or it literally doesn’t bother you at all?

Jon: It doesn’t bother me at all. It really doesn’t. The thing is I suppose if I sat down, I could check the stats and I could probably draw a graph with two lines and where they intersect is the sweet spot. That would give an indication of how many F bombs I can drop and how critically direct I can be, but I don’t care. I just do not care. I make plenty of money and I don’t care if I make an extra 20% because I stopped swearing so much. It just doesn’t worry me.

The other thing is this. It really started when I had taken on a copywriting class. I found it hard work. I went to [inaudible 00:10:08] on all the networking stuff with the local chamber, where I was being nice to people, being kind of [inaudible 00:18:14] commerce professional. It hurt it and it didn’t get me any business.

I thought, “I’m poor anyway so I might as well be poor and happy and be obnoxious.” I started being obnoxious, then just being me. I always figured that at some point, anyone I work with is going to find out the kind of guy I am. I’m basically libertarian, not politically correct, everything else. At that point, if they really object to it, it’s going to become difficult working with them.

That actually happened before with a bunch of moments, so I thought if people know what I’m like upfront, I’ll never get that problem. No one gets close to me, but I’m talking about business now, nobody gets close to me in business without knowing exactly who they’re dealing with. If they don’t like that, they won’t go any further and I won’t play willy-nilly. That’s all great, that’s fine, more power to them.

It means the people I do work with including my inner circle are, I love it and they love me. The thing is, it pays off because my retention rights … look, in my kind of thing [inaudible 00:19:19]newsletter thing so there’s a paper newsletter, CD, telecoaching call and a discussion forum online and for that kind of membership, similar kind of prices, for that kind of membership, in my industry, the average retention rate is 50% over two months. People come along and two months later, half of them are gone.

For me, I keep people on average who are at least 85% will stay for a year or more. My results are [inaudible 00:19:45] and I think that’s for two reasons. One, because of the way I run the group. Two, because I’m very careful about whom I let in, my bullshit [inaudible 00:1953] is very, very strong. Nobody joins if they’re wilting flowers, shrinking violets or the rest of it, they just won’t. Great, I don’t want them there.

My sign-up rates are good. They’ve been like 8 1/2 % of people who join my list go on to join my inner circle. It’s not like I’ve got a very small number of people who stay on time, my opt-in rate is high too. Even the opt in pages on my Web site, I’m immediately positioning myself as someone of a certain kind, but I only want certain kinds of people on my mailing list. That’s why my opt in page is 2,000 words long. I’ll immediately start the positioning process. I’m not trying to catch everybody and hope that some of them will stay. I don’t want certain people on my list because I just can’t have a problem dealing with them.

John: All of the Internet, it’s all about trying to optimize, optimize, optimize to get as many opt ins as possible, but like you’re saying, is that it can be far more effective to polarize and only get the people that are actually going to care about what you’re offering and that’s it and forget about the rest entirely.

Jon: Definitely. You can’t sell to everyone anyway. You’re not going to want to, to be honest.

John: We’re just about coming through about that time. To summarize all these, we got daily emails that which you should be sending them. Number two is be real, polarize people, so swear, be yourself whatever that ends up meaning depending on the person, don’t be too extreme though and tell stories and then last one was, just don’t try to get everybody. Do you have anything to add to that?

Jon: Yes, I can, actually. That’s another reason to be yourself. You cannot please everyone. You can only please everyone some of the time. No matter what you do, someone’s going to hate you for it. You might as well make sure that at least one person’s happy and that is, please yourself. Here’s a interesting thing to leave people with. I have both men and women on my list, I mean on my inner circle. I cannot recall a single instance of a woman complaining about my bad language or being offensive in any other way, it’s always the men.

John: That’s very interesting. I would think it would be the complete opposite.

Jon: The women love it.

John: That’s really cool. All right, man, thank you for this. Thank Steve for your time. Before we go, tell people where they can find you and then we’ll say goodbye.

Jon: The easiest thing to do is to get to my Web site which is Jon Mcculloch dot com which is spelled, j-o-n-m-c-c-u-l-l-o-c-h dot com. Read the opt in page, 2,000 words and then just leave the details at the bottom. If you want to get on my daily email [inaudible 00:22:26] as opposed to the pre-written 52-idea sequence, they can just reply to the first email and say, “Please put me on your daily list” and I’ll do that.

John: Awesome. We’ll have those links in the sharing notes so you can find them there. Thanks again, Jon and see you soon.

Jon: Thanks, John. Bye.

John: Hey, everybody. Thanks for listening. If you want to discover more insider tips, tricks and secrets about driving sales in email marketing, sign up for daily email tips from Autoresponder Guy. Go to drop dead copy dot come slash podcast. Sign up and put your email address and I’ll send you daily emails on how to improve your email marketing and make more sales via email. You’ll find out why open rates don’t matter and the seven-letter word that underlies all effective marketing and much more.

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