Email marketing is a powerful tool in the hands of an online entrepreneur. It's a way to stay top-of-mind with customers and prospects, drive sales, generate leads, build your brand and so much more. But like any other marketing tactic it requires some knowhow to be effective.
Our guest Chris Orzechowski is known for his high-converting copy writing for emails. Tune in as he and James break down email lists, how to write an email that sells, how often you should email subscribers, and more.
In the interview:
This episode has guest Chris Orzechowski from New Jersey, and it came about in a funny way.
James recently helped someone with a promotion, for which they got very, very good conversions, and James commended this person on how good their email was. Next thing he knew, he got an email from someone else in the industry saying, Hey, buddy, you should know this email is very heavily modeled from a friend of mine.
This friend was Chris, which kind of makes sense, said James, as Chris’s website is theemailcopywriter.com. It would be logical for someone wanting to send a good email to follow an email copywriter and be inspired by them.
James was somewhat mortified by the incident, as he had never copy pasted any piece of copy writing in his life. These days, if someone provides him material for a promo, he rewrites it to where it’s sure to pass a plagiarism check.
But James did think it would be great to have Chris on the show and explain just why his email worked so well, and offer some insights too about email marketing in general.
The elements of a standout email
The reason this email converted so well, Chris thinks, is because it referenced a frustration from his own life, in terms of spending on ads, starting to scale, and then seeing things go awry, whether through single-channel dependency, getting accounts shut down, or CPA shooting through the roof just when things were going well.
“Email marketing is about entering the conversation in people’s minds.”
In short, it was a real problem, not some contrived hook. His readers were actually experiencing it. Email copy is about entering the conversation in your reader’s mind. And if you’ve been through a problem that you know they have, those often make the best emails.
Negative versus positive situational content
James wonders, what if you’re writing about something positive? He’d had a really successful promotion recently, where he talked about a real-life positive situation that happened to him.
Someone had emailed him wanting to buy something of his, an asset he’d built up for some time. And that had been his goal from day one, to make it so valuable that someone would want to pay good money for it.
James shared the story with his audience, and then had great success promoting a product that teaches people to do just what he did. So can a positive outcome work just as well as a negative?
“People are going to put themselves in the shoes of the person in the story.”
Chris thinks it can be either or. And the way he looks at it is, people are going to put themselves in the shoes of the person in the story, whether it’s the hypothetical you you’re talking to, your hypothetical prospect, or if it’s a story you went through in your own life.
When you can fuse that little bit of storytelling and that little bit of personality, it’s powerful. Look at where all the attention is in society, says Chris. It’s on social media, on influencers. People’s screen times are reported as six hours a day. And they spend it watching other people live their life in real time through an Instagram story, through a TikTok, through whatever it is.
Drawing on life to fuel daily emails
Chris send out emails daily, sometimes twice a day. And for the most part he talks about what happens in his life.
His view of email is of people trying to climb a mountain. They’re at point A, wanting to reach the summit, and in between are a number of basecamps. With his emails, Chris tries to move people from basecamp to basecamp, milestone to milestone.
What Chris tries to do is say, I’m a practitioner, I have my agency, we work with clients, we do some more consulting and coaching, we’re starting to roll out those kind of things. But most of it’s done-for-you services.
As much as he can, he’s trying to show his work, and say, Here’s the things we’re doing, here’s the things we’re testing, here’s something that worked, here’s something we noticed, here’s a frustration from the client we heard… and tell those stories. He doesn’t do it with every email. Sometimes he’ll tell slice of life stories just to build up that resonance.
But most of the time, says Chris, it’s demonstration after demonstration. Because if you show up and do that every day, people will say, when it’s time to make the buying decision, Wow! That dude knows his stuff. He talks about it every single day. He can’t shut up about it. That’s the framing he tries to take.
How many emails a day is overkill?
Now some people say there’s no way they’d send an email every day. Their customers would unsubscribe. What does Chris have to say about that?
Chris has been under the hood of hundreds of businesses, and he’s never seen that happen. Yes, you’ll get some unsubscribes, he says, but people unsubscribe no matter what you do.
The reason you’re sending the emails is for yourself, because if you can generate cash flow for your business, for your brand, you can grow it. You can grow your organization, you can provide yourself a better life. And that is what’s going to give you the motivation to continue to grow.
So instead of focusing on the one disgruntled individual who unsubscribed, think about the customers who are giving you money, whose lives you’re changing with your product. That’s how he puts it, he says, and people get it.
James thinks there’s often a mismatch between personal tolerance and the marketers who are sending a lot. There’s one marketer he thinks of who’s relentless with his offers. It’s like a pitch fest on a launch, which he does a lot of. He might send five or six emails on the last day of the launch. And his stats will show that he makes more sales, but James would coin the word obnoxious for that.
When James himself does a promotion, he says, he’ll send two or three emails. Does Chris think there’s a line that sometimes gets crossed? Or does an email marketer say, Well, there’s no such thing as obnoxious? It’s just the wrong people on the list?
It’s one of the great contradictions, says Chris, and he actually doesn’t know the answer. He has thoughts on it, but he doesn’t know what is the objective definitive truth, because he sees examples on both sides of the spectrum.
“People don’t read ads, they read what interests them. Sometimes it’s an ad.”
Is it good content? Is it helping them? Because if so, who’s going to say no to more help? If it’s just a pitch, pitch, pitch, Hey, buy this thing, buy this thing, buy this thing….
The cool thing about email, Chris says, is your email marketing system is a filter for your list. And eventually if you bombard people long enough, the people you’ll be left with are going to be the headache problem buyers who just float from product to product and who only respond to the hard pitches.
You kind of get what you deserve after a while. People who resonate with your stuff and who like it will stick around, and there’s definitely demographic, psychographic characteristics that will emerge like common trends and patterns.
Chris says some clothing brand lists like Lululemon and Brooks Brothers will email you six times in the day. Part of him can’t believe they’re doing that. But the other part of him thinks, okay, it’s a billion dollar brand, right? Maybe you don’t get to that size unless you are willing to crank the dial up.
“Not everyone wants to build a billion dollar company.”
Of course, not everyone wants to build a billion dollar company. Most people will establish a rhythm that they feel good about.
Best practices for email segmentation
A problem James sees in online marketing is that many companies don’t separate transactional emails from promotional emails. So if he buys someone’s information product, he’ll now receive their whole next wave of launches. He can’t just get product information about an upgrade to the product he bought.
In his business, people are placed on a different segmented list. And should they go to unsubscribe, they’ll see several different campaigns they can choose from. They can stay a member but not receive a promotional campaign email.
Does Chris have segmentation best practice he would talk to clients about?
If your email software, say Active Campaign or Ontraport, has the capability, Chris recommends the kind of segmented opt-out that James describes. It gives people the opportunity to choose their own adventure or how they want to interact with your brand.
That’s likely, he says, why James has a seven-figure business with a four-figure list. Everyone wants the big list. But what percentage of that list is buyers? What percentage of those people are engaged? What percentage of them actually want to be there?
Chris currently sends all his transactional emails from Kajabi and all the marketing emails from ConvertKit.
How do you actually get people onto your list?
How people get into your database in the first place is important, says James. There are various ways to chase vanity metrics, but James wants to know what Chris recommends to build quality email lists.
Chris has a little magic trick that he’s done, adding hundreds of subscribers in a single afternoon. It’s four sentences long, and it’s how he started and grew his list to critical mass.
You make a post on Facebook or Twitter. His first was titled, he says, The Seven Laws of Email Copy Writing. That was one of his first lead magnets. He said, Hey, I’m putting together this thing. It’s called The Seven Laws of Email Copy Writing, we’ll be documenting all the things that I do whenever I write email sequence. If you’re interested, comment below, write email on the post.
People will comment. It will create an avalanche, a snowball effect, of social proof as people in your organic warm audience start to comment on it. Other people will comment because they’re seeing people comment.
And then you message every one of those people and say, Hey, thanks so much. I want to send you my thing, give me your email address. I’ll add you to my list.
Chris likes to put in the post, If you’re interested in this, I will add you to my list and send you this thing when it’s ready. That way they know what’s going on. Then he private messages every one of them. It could take a couple of hours. But doing that, he went from 55 subscribers to 110 and then to 300, and so on.
It takes some sweat equity, but when you’ve built your list you can start making money by serving people and by having that leverage that a list gives.
A great strategy, says James. The sort of people who join the list after that activity have already been following you. They’re interested in what you’ve got to say. You’re just moving them from one medium to another. He calls this a list guarantee. You want people to subscribe on Apple, on YouTube, on your Facebook page, so that you can reach them in ways that aren’t obnoxious.
Maintaining the quality of email lists
Something we might assume, says James, is that our client is seeing everything we produce on every platform. The reality is, even if you have a really hot open rate, he would suggest maybe most people don’t get more than 25 or 30 percent open rates on a house list of generic emails.
Some of those really big lists, he says, are not very powerful. They’re watered down, not getting the opens or the traction.
What does Chris think of strategies like whitelisting? James was told a good technique is to ask people to reply to you on one of the early emails they get. Then you can float them into the correct part of their inbox next time you send an email, because they’ve proven they’re interacting with you. But also, it’s a really good point to get feedback or data to start that relationship on a deeper level. Does Chris like that technique?
Chris has done it himself for years. And as his list has grown, his list health has stayed the same in terms of opens, clicks, engagement in general.
In the very first email, he asks people to reply if they received it. Not everyone does, and that’s fine. But the people who are “hot leads”, who are really interested in his stuff, are like, Oh, my god, yeah, I can engage in dialogue.
Chris is a big fan of Dean Jackson‘s conversational approach, where you might ask what business someone’s in, etc. He’s gotten people to tell him how they want to become a copywriter, or are in ecommerce and unsure about their email.
That’s where Chris can start prescribing solutions – a blog, a podcast, a program. And those people typically continue to interact over the life cycle.
What’s insanity, says James, is the people who spend to get a customer, and then email them from a no-reply address.
Chris has worked with some brands who said they weren’t set up to handle the replies they’d get. Why not hire someone, he’d say? There’s money in those replies. And it’s a win-win – the company’s getting paid, and the customer gets helped.
Giving the behind-the-scenes look
What is Chris’s thing, asks James? What is he known for or what would be the go-to Chris thing that needs to get out there?
Chris is still workshopping it, but it’s kind of like, show people what’s going on at the factory floor. Take people behind the scenes of HQ of what’s going on in your business. They use this strategy all the time.
Most of Chris’s clients are in the ecommerce space, but he does it with his own list, like, five out of his seven emails every week. The factory floor for him is them in the writing room, them in the Google document.
For e-commerce, it’s like, Hey, what’s happening? Oh, you guys make fire pits. Tell us about the new one you’re designing. Tell us about the craftsmanship. Don’t create emails, just document what you’re doing. Talk about the work that you’re doing, talk about the pursuit of excellence that you’re on.
It’s like Tim Ferris’s open the kimono, says James. Like Gary Vee says, document the journey even if you don’t have anything significant yet. Someone like Dean Jackson would come up with a really cool name for that process, James is sure.
It’s all about the narrative story
People love narrative. It’s just what people watch, what people pay attention to, says Chris. Even the news (not that he watches it). It’s all just story, story, narrative story.
It’s a universal truth about how our brains work, he says. People don’t even watch movies anymore. They watch these long, episodic series. And Andre Chaperon, he could see into the future. His stock has just gone up and up, ever since the soap opera sequence came out. He was very early on that, understanding that.
A framework to simplify storytelling
Does Chris use a framework for storytelling, asks James?
Before he got into copywriting, says Chris, he was a school teacher, teaching special education, elementary school, language arts. He had kids who couldn’t write a full sentence, and his job was to get them to write a page or two story. It was very hard.
That’s when he learned about frameworks. And one he discovered was:
As long as you nail those five parts, he said, that is a more compact version of the hero’s journey. But it’s something so simple that a third grader can grasp it.
Somebody, wanted, but, so, then. So somebody, they wanted something, but there was this obstacle in the way. So then they did this, and then this happened.
That’s perfect, says James. The gold in this episode.
Why you should email your list at least weekly
One more point James thinks is important. He has it from an email delivery expert that if you don’t email your list at least once a week, you will get throttled by the email delivery providers. Your deliverability will start to suffer because they won’t take the risk on sending stale emails through their good quality supply.
How often would Chris say is the longest you would want to leave your audience without emailing them?
One week is the absolute longest, says Chris. Time moves so fast, and we’re surrounded by media. Our sense of time is so warped that any longer than a week and people will start to forget who you are.
If you’d like to know more about email copywriting, Chris Orzechowski is the man. You can find him at theemailcopywriter.com.
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