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This $100+ Million Copywriter Will Teach You To Re-Engage Your Email List (An Interview With Chris Orzechowski)

Back in 2018, my business partner Mike Yanda and I were getting ready for our first-ever product launch, and we needed a copywriter who could spin up a high-converting sales page and emails. Mike met a guy named Chris Orzechowski through a Facebook entrepreneurship group and thought he’d be a good fit.

There was something about Chris. Not only was he a former teacher like me, but he’s also super direct with an irreverent sense of humor. You’ll know that about Chris if you follow him on Twitter. He also laid out a strategy that both Mike and I liked, and it did better than we expected: $136,000 for our very first product launch.

Since then, I’ve gotten to work with Chris a little more and watched him go from freelance copywriter to email marketing agency owner known for his “Orzy” writing style. I even recently hired him again to help with another new product launch, and I’m stoked about where he will take us.

It’s been ten years since Chris started, and he’s worked with over 200 clients, generated over $100 million in revenue, and helped over 4,000 students start their copywriting careers. Because it’s clear that Chris knows what he’s doing — and I have firsthand experience in his very capable hands — I wanted to spend some time talking with him about what business owners, new business owners especially, need to know about email marketing.

This is a must-read interview if you’ve been neglecting your email list or haven’t implemented any kind of email strategy.

Hey, Chris. Looking forward to talking with you, but before we get started, I want to ask about a recent feature article about you that said you made $974,000 in top-line revenue last year. The kicker is that you only work four to five hours a day, with less than ten years of experience as a paid copywriter.

I am sure there are some people wondering what’s the catch or scam, and what would you say to anyone questioning the legitimacy of those numbers?

Sure, it might sound crazy. But for the past seven years, I’ve been building up my email list and creating scalable offers that help me “clone myself” and work with clients and students in more leveraged ways. I have 21,000+ email subscribers and well over 4,000 students who have bought products from me over the years.

I make a lot of money from doing client services on a one-on-one basis. My project fees start at $10,000 per project.

I also do consulting, coaching, and team training, and I work as a fractional Chief Marketing Officer (fCMO) for two brands.

On top of that, I sell books, a $149/month print newsletter (with 200+ subscribers around the world), digital courses, and group coaching programs.

Plus, I have affiliate income coming in from different services, tools, and software that I promote from time to time.

So, in reality… it’s not crazy at all.

I’ve found ways to sell “Chris Orzechowski” to many different segments of the market at different price points.

I’ve heard a lot of business owners say one of the biggest mistakes they made when they started was neglecting their email list, either not starting one or not nurturing it. Can you talk about why it’s so important from day one?

The truth is, an email list is one of the only assets you can truly own in an online business setting.

You don’t own your Instagram following. Instagram owns it.

You don’t own your Twitter account. Twitter owns it.

You don’t own your YouTube channel. YouTube owns it.

YOU own your email list. That database is where the money is. If you lost all your social media accounts, you’d still be able to make money as long as you had your list.

Plus, email has an insane ROI compared to the effort you put in.

There’s a reason why every social media personality, influencer, or marketer eventually funnels you back to an email list.

The email inbox is intimate. It’s something people check multiple times a day. It’s where all of your important documents and receipts are delivered. The bigger and better quality list you build, the easier it is to make sales.

You’ve said that email has an insane ROI, and I’ve read that the return on every $1 you spend is about $36. Does that sound right to you? Or is there another way you like to look at the ROI of the time and money newbie business owners put into their lists?

I’ve seen that statistic thrown around, but I have no idea where it comes from or what it refers to. I don’t know how people arrive at that figure.

Return on what? What you pay for your email software?

There’s no acquisition cost to send an email, like there is for something like a Facebook ad.

If that number is calculated based on what you pay for your email software, my business had a 697:1 return on investment last year.

I think a more useful statistic for business owners to pay attention to is “revenue per subscriber.” You divide your monthly revenue by the number of subscribers.

This metric gives you an overall look into the general health and performance of your email program. It’s simple math, but it’s influenced by your sending frequency, list size, deliverability, strategy, opens, clicks, conversions, and more.

If your RPS is too low, you know you’re leaving profit on the table.

As long as your RPS is trending in the right direction, you’re in good shape.

That metric makes a lot more sense to me, and that’s how we like to check the health of our list too.

Now, I’m sure there’s going to be someone reading this feeling like they’re missing out because they haven’t been focusing on their email list. So for those business owners, can you outline the most basic and actionable steps to getting started? What should they do first?

So if you haven’t emailed your subscribers in a while, the first thing to do is send a re-engagement campaign. This is typically 1-2 emails long that essentially “reintroduce” yourself to the subscribers.

It’s a good idea to remind them how and why they got onto your list in the first place. Then, let them know you’re going to start emailing regularly again. And then give them the option to opt out.

It’s also good to tease some of the content/topics you’ll be covering in the coming weeks to hook people’s interest. You can also use this as an opportunity to direct them to any new products or offers you have.

From there, what are some simple best practices for nurturing your list?

Once you’ve run your list through a re-engagement campaign, you now have an “active segment” that you can start mailing to.

The best way to nurture this segment is by sending at least one email a week.

I like doing a “Behind the Scenes of HQ” style email. You simply tell a story from inside the business. Tease some new products you’re working on. Talk about the work you’re doing and how you’re building the brand.

People like this.

They like an inside look.

It also builds a strong bond with your subscribers. They feel like true insiders.

If you start doing that once a week, you can add an additional weekly email (on a different day) with a more straightforward product pitch.

It’s also a good idea to plan at least 1-2 deadline-driven promos each quarter. These are periods of more aggressive promotion with some kind of consequence for not buying. It could be a bundle deal, a discount, a gift with purchase, or maybe a limited run of a certain collection.

As you’re doing all of this, you should be building some lifecycle automations each week to generate more automated revenue. Examples of these are things like welcome sequences, abandoned cart sequences, and post-purchase sequences.

Rome wasn’t built in a day.

Build your infrastructure one email at a time.

For anyone who is ready for the steps beyond that re-engagement campaign, how should they prioritize their email efforts?

The highest value thing you can do is build automated sequences that sell while you sleep, so you can then scale while you sleep (which happens to be the title of the book I wrote on e-commerce email marketing automation).

If you already have a full suite of lifecycle automations that are selling and cross-selling products to your customers, you’re in great shape.

The next best use of your time and energy is to find ways to grow your list, so you can feed the machine.

And now, for a really long-term look, when should you start outsourcing your copywriting responsibilities to a professional like you or someone who’s gone through your coaching program?

My philosophy is the same for any role.

When you are at a point where you can get a greater return on your time elsewhere in the business, then it’s time to outsource.

Most top copywriters aren’t going to work with brands that are doing less than seven-figures unless you have some other X-factor to offer (a network, unique experience/access, performance incentives, etc.).

Do not even think about approaching a copywriter unless you have product market fit… and have at least one solid traffic source.

Copywriters aren’t magicians.

They can’t multiply zeros.

If you can’t achieve success without hiring a copywriter, you need to go back to the drawing board and improve your offer.

That’s all really great advice. As we wrap up, is there any other advice, wisdom, or guidance you’d like to share?

I have two pieces of advice. One is from Napoleon, and one is from Charlie Munger.

Napoleon said to “Never interrupt your enemy when he’s making a mistake.”

Don’t worry about what your competitors are doing. Don’t dunk on them if they’re doing something stupid or detrimental. Don’t blindly copy them, because you have no idea what’s behind the curtain of their business.

Focus on you, yourself, and what you can control. At the end of the day, that’s all that matters.

Secondly, “The first rule of compounding is to never interrupt it unnecessarily.”

It took me five years to get to 5,000 email subscribers. That’s five years of posting blog articles each week, appearing on podcasts, giving private trainings to different groups and memberships, and writing an email to my list every single day.

It took me two years to double that and go from 5,000 subscribers to 10,000 subscribers.

Thirty days later, my list doubled again and went from ~10,800 subscribers to 21,000+.

Consistency is the name of the game.

People who achieve overnight success typically become overnight failures.

Hold the line.

Stay in the game.

Keep your head down.

Outwork everyone.

To the victor goes the spoils.

Chris, this has been awesome. Thank you so much.

If you want to learn more about Chris, his agency, and his books and other products, you can find him at The Email Copywriter.



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