Freelance Copywriter Mike Connolly With Dan Kennedy's Dean Martin Rolls Royce 600 x 300 Hi Res

I recently invested in two days with Dan Kennedy, learning about the business side of being a highly paid freelance copywriter.

In case you’re a stranger to “Planet Dan”, he’s known for his direct response copywriting and “millionaire-making” marketing strategies for small business.

He’s also one of the highest paid copywriters, earning seven figures consistently — part time.

To give you a tiny but quick glimpse into all he taught, read on for three (out of many) of his tips for becoming a highly paid freelance copywriter.

Note: If you’re just looking for copywriting tips or how to become a better copywriter, this post isn’t for you. It’s strictly about the business of copywriting.

That said, let’s dive in, shall we?

You Don’t Get What You “Deserve” — You Get What You Engineer

Being a successful freelance copywriter depends on getting paid enough to at least keep you in Ramen noodles once a day. But once you get good at proving value to your clients, there’s serious money to be made as a freelance copywriter. 

You need to be clear that getting paid well isn’t just about being a great copywriter. Them’s just table stakes.

As Dan Kennedy teaches, your compensation must be engineered

In other words, you cannot count on gratitude or goodwill for a job well done if you want to be paid well. These things are all good for business, but you can’t predict them.

If you want to enjoy a six or even seven figure income as a freelance copywriter, you must, to the extent you are able, take charge of what, when and how you get paid.

Let’s look at a few ways to do this.

Send a Quick Recap

Jot down details of every business conversation you have with a client and send them a copy.

Email is ideal for this. But don’t forget, you can also use regular mail, or even fax, as Dan Kennedy does. 

The key, especially for high ticket deals, is to keep a running record of conversations with your client. Small business CRM systems like Infusionsoft, Hubspot, Zoho, Insightly and others can be extremely helpful for this.

Get It In Writing

Put your agreements in writing, and get them authorized before moving forward. I know, duh, right? Still, a little extra clarity with your client could save you countless headaches, arguments, lost business and a less than stellar reputation.

When you’re the one putting all the details in writing, you can structure the agreement to make sure you’re getting paid the way you prefer. As long as it’s agreeable to your client, of course.

So being proactive in structuring the deal can put you in a good position to be paid well for your time. But it’s not the only way…

Weave Key Facts About How You Get Paid Into Your Content

You’re a copywriter, right? Write up your success stories and share them with your target audience in your blog, newsletter and/or their favorite social media sites.

And while you’re at it, you can mention cool details about the boodle your happy clients are paying you.

Of course, you’ll want to show why you’re worth it. And offer proof that your copywriting clients are more than happy to ante up. Then when it comes to having a conversation with you about price, there’s no question. Prospective clients will be predetermined to buy from you, knowing full well what it will cost.

Dan Kennedy is a master at this. You’ll find mentions of his initial consulting fee (just a tad under $20k as of this writing) in the newsletters, books and other media he writes. It’s all part of how he engineers his copywriting paydays.

Don’t Try This At Home (Unless You’re Willing to Take a Chance)

Now, here’s something you can do if you’re feeling plucky.

The late great direct response copywriter Gary Halbert was invited to speak at a conference in Las Vegas. The promoter offered Gary a speaker’s fee, which he turned down. 

Instead, as the story goes, he suggested, “I’ll come and speak without any obligation for a fee. When I’m done, you can send me a check for whatever you feel it was worth.” 

As it turned out, the check he received was several times bigger than what the original speaker’s fee would have been. 

Now, this is a really interesting way to set up a situation where you can carve out a nice chunk of change for yourself. But you better be good (Halbert was). And you better be good at creating perceived value. Halbert was both.

Obviously, there are some risks involved, but it could be well worth your while. 

So those are just a few of the MANY ways to engineer the compensation you receive. The point is, it’s up to you to make it happen.

It’s Far Easier to Keep Clients You’ve Got Than to Go Out and Get More

The more clients you work with, the more obvious this becomes.

In a moment, I’ll show you how to retain your best clients. But first, to remind you how crucial this is, here are six ways keeping a solid stable of lifetime clients will save you time, money and effort.

6 Big Reasons Why Client Retention Matters

1. Attraction

No matter your prospecting method, whether you grab a spear and go hunting, or cultivate prospects like a farmer… you have ad cost.

It takes some combination of time, money and effort to get the word out for prospects who have no idea who you are and to entice them into the top of your marketing funnel.

That alone should give you enough reason to consider instead investing those resources into retaining clients who you already have.

2. Conversion

Number two is the expense of converting cold leads into interested prospects.

If you were selling sticks of gum or some kind of impulse buy, that’d be one thing…

But as a copywriter, you need to go through a whole process of educating and informing potential clients about who you are.

The whole process of converting them from being aware into being interested in and engaged with you takes time and painstaking effort, robbing you of time better spent helping your current clients succeed.

3. Indoctrination

The third reason to focus on keeping the clients you already have is that once a new prospect has engaged with you and interested in what you can offer, you need to build a sense of trust.

You need to give him the feeling that you are a person who has what he needs. That you can be trusted. And you must prove you’re the best alternative he has.

Ideally, you want him to see you as a “category of one”. And that is not easy to do.

Indoctrination takes a lot of effort and expense. Add that in to the cost of advertising and converting clients. Right there, you’ve got reason enough to retain the clients you’ve got.

But we’re not through yet…

4. Onboarding

Consider the onboarding process.

Getting to know your clients takes time.

And there’s always the risk at this delicate stage that you’re unable to form the kind of bond you need with him in order to have a good working relationship.

It takes time, effort and commitment. And again, these costs mount up.

5. Referrals

Factor numero cinco is referrals.

A client isn’t likely to refer you unless he feels extremely confident that telling others about you and the service that you provide won’t come back to bite him.

The longer you work with a client, the more likely he is are to refer others to you.

And of course the beauty of referrals is that you can skip all the expense, time and effort of advertising, converting, indoctrinating new clients.

So referrals are a critical part of your marketing. And again, they rarely come from anyone but long term, happy clients.

6. Reputation

And then finally, comes number six, reputation.

How people feel about the service you provide is based on their experience with you.

If you are providing the kind of service that keeps clients with you, then it’s natural that they will provide comments and reviews and conversation with colleagues, friends, that will lead to a great reputation for you.

Those types of public proclamations don’t come from casual encounters. They come from clients who have worked with you and who can feel confident in putting their reputation on the line by saying good things about you.

3 Ways to Keep ‘Em Once You’ve Got ‘Em

Okay, so you’ve come to realize how mission critical it is for you as a freelance copywriter to keep clients coming back for more.

Here are three ways to do that.

Way #1: Become “Indispensable”

When asked what he felt was the key to success, comedian Steve Martin said, “Be so good they can’t ignore you.”

Same goes for keeping copywriting clients. But there’s a trap here you must avoid.

It’s less about being a great copywriter than it is about helping your client succeed in getting what he wants. Keep your eyes open for opportunities to make a simple tweak that can make a big difference in conversions.

You could save yourself a boatload of time trying to write a kick-butt long form article or sales page, when all that was needed was to tweak the headline with a word or two to double the conversion rate.

And, after all, what your client really wants from you is a conversion rate he can feel good about.

Way #2: Cross-Sell, Upsell and Downsell

Gurus may advise you to specialize in one media, channel or type of writing. The problem with this is, it forces your client to shop elsewhere if you can’t do it.

You’re doing yourself and your client a huge disservice by making him go to all that trouble.

Instead, become expert in all the types of copy your specific type of client needs copy for.

If you’re writing for attorneys, for example, you might become proficient in SEO, Pay-Per-Click, web pages, newsletters and email sequences — and sequencing them all together.

You win, your client wins.

And he’ll stick around for more.

Way #3: Keep ’em Fascinated With Fresh, Relevant and Interesting Content

Fact: You can’t bore people into sticking around. When the party gets dull, partygoers vanish.

Same with clients.

You keep him coming around by answering the ever-present question, “What’s new?”…

You can do that with a monthly newsletter, weekly or daily emails, social media content, articles and more.

Dan Kennedy regularly sends a special “Box o’ Stuff” including tear sheets, articles and items of special interest to his particular group of clients.

You also keep their interest by continually innovating and reinventing your business, creating new and exciting offers of particular interest to your clients.

All said, sticking with the one who brung you to the dance tends to pay off in the long run.

It’s Not WHAT You Sell… It’s Who You Are to Your Client

This third freelance copywriting business tip I got from Dan Kennedy is: Don’t confuse your deliverables with perceived value. Clients are acutely aware of who they hire, and what that person represents to them. They want good results, of course. But what they DON’T want is to look foolish. 

If you don’t hold a special place in your client’s mind, you’re at risk that clients will view you as just another copywriter. In which case, they’ll try to look smart by getting the lowest price they can from you.

Let’s break that down a little…

The more you get paid for who you are rather than simply the copy you write, the more you can charge. Your authority, credibility, certifications, social proof and track record demonstrate your value. In essence, it’s your brand. And if they can put their trust your brand, you become much more valuable. You want to be the copywriter your client sees as worth paying extra for.

Consider brands like Apple Computer, Nike, Rolex, Jaguar, and of course, Dan Kennedy himself. People pay a premium for brand. If all you compete on is your deliverables, you’re at risk of becoming the Walmart of copywriters.

So it’s your ability to enhance your deliverables with your name that’s going to determine the premium you can charge. Otherwise, you’re in a cutthroat race to the bottom, with razor thin profits. And we all know how that’s likely to turn out.

So how do you do that? Here are three ways to be able to magnify your influence. 

Media Choice

Way #1 is through media choice. For instance, in direct mail, you can be the only person speaking with your prospect. You’re out away from the din of social media and search marketing.

One powerful direct mail piece that Dan Kennedy is famous for, and that his acolytes call a “Shock & Awe Box” (or what I prefer to call a “Discovery Kit”), you can send to prospective clients who show interest. 

One of the reasons a Discovery Kit enhances your positioning is, nobody else is doing it. And that puts you in a “category of one”. You’re literally incomparable. And therein lies real pricing power. 

Rule Out All Options

Way #2 is to ethically and credibly discredit every alternative available to your ideal client. You show why and how your services are superior by proving that none of the alternatives stack up to hiring you.

Create Your Own Universe

Way #3 is you create your own client feeder system. Rather than depend solely on popular ad networks or word of mouth to bring in new business, create your own multi-media platform where qualified prospects find you, consume your content, and “gestate” until thoroughly predetermined to do business with you.


Now, the freelance copywriting business tips I’ve just shared with you aren’t for everyone. 

And that’s very good news for you. 

If you implement them well, they can help you become worth much more in the eyes of your ideal clients — even in tough markets and tough times. 

If you study the top copywriters in any niche, I believe you will see this underlying pattern. 

And now, one of those top copywriters could be you.

By the way, these three breakthrough business strategies are only a fraction of all that Dan Kennedy teaches. To learn more about Dan Kennedy, you can find his books on, and

And you’ll learn more about my favorite direct response copywriting and marketing strategies when join the hundreds of subscribers to my Strategic Marketing eLetter. I look forward to seeing you there!

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Mike Connolly
Mike Connolly

Dan Kennedy Certified Copywriter for Info-Marketers and Infusionsoft Certified Partner, Mike Connolly lives in Boulder, Colorado, builds marketing funnels that rock, and loves cycling (almost) all year round.