I’m self-taught as a marketer. No marketing degree (I have an accounting degree instead) and no formal copywriting education.
So I’ve read quite a few marketing, copywriting, and business books in my day.
A lot of them are “good enough,” but either too niche/specific or derivative (in the positive sense) of previous works.
Maybe I took something new from them, but they just don’t quite hold up to the 7 on this list.
Some of these are CONSTANTLY recommended in copywriting circles, and I can see why. Others are a bit more under the radar, offering hidden gems to those who read them.
Either way, you’ll learn a bit about each book and a key takeaway or two that have stuck with me from each long after reading.
Let’s start with one of my all-time favorite copywriting-specific books…
1. The Adweek Copywriting Handbook by Joe Sugarman
If you’re going to read one copywriting book, start here.
Sugarman is a copywriter first and a teacher second, so the book reads the way good copy reads:
Clear, logical, easy to follow.
He walks you through the process from initial research all the way to the finished edit in Section 1 before covering some tactics in Section 2.
Then, Sugarman takes you through a dozen real-world ad examples to demonstrate the lessons in action. Toward the end, you learn how to apply these concepts across different media.
Sugarman included a few appendices summarizing the book, building on certain concepts covered early on, and recommending further reading.
Two concepts from this book stuck with me more than anything else…
1. The Slippery Slide
The idea is simple:
Every line of copy exists to get the reader to read the next line.
Once you understand that, you start reading every sentence you write differently — does this earn the next one, or does it slow things down?
Seems obvious. But newbie copywriters often add flair that, while well-intentioned, backfires by distracting the reader and diluting the message.
2. Selling a Cure, Not a Prevention
Every time I get sick (especially with a sore throat), I beg and plead to get healthy, promising to never take health for granted again.
And then when I’m healthy, I toss that out and live my merry life, forgetting I was ever sick.
I know I’m not the only one. That’s because people have limited attention and care. They don’t care about preventing a theoretical problem as much as curing a real pain they have right this minute.
Yet another way your offer determines your success.
Selling an NSAID pain reliever is easier than selling a multivitamin that prevents the cold you need the NSAID for, for example.
However, a clever marketer can turn “preventative” products — whether that’s a multivitamin, an insurance policy, a lawyer on retainer, or something else — into a “cure” through adjusting the copy or targeting a different market.
For example, a tax lawyer selling “protection from future IRS audits” won’t do as well as a tax lawyer selling to people who just got that dreaded letter in the mail.
Grab The Adweek Copywriting Handbook here
2. Ca$hvertising by Drew Eric Whitman
This was the first copywriting book I ever read. I remember reading a few pages out on the bench during lunch at my first (and only) “real job.” I was 22 and figuring out what copywriting really was.
I’ll be honest:
I don’t remember much of it in granular detail. When you read a book that early, with that little context, a lot of it doesn’t “click.”
7 years and several copywriting and psychology books later, a lot of what I learned from Ca$hvertising has blended into a broader foundation I can’t always trace back to a specific source.
What I do remember is that it’s not a “learn the fundamentals of copywriting” book.
Where Sugarman (and some other copywriting authors) gives you a framework and walks you through the logic, Whitman gives you a compilation of specific tactics grounded in consumer psychology research.
Things like:
- The 8 basic human desires that drive nearly all buying decisions
- How to connect with readers on a deep emotional level
- What a good ad should “feel” and read like
- A quick pass/fail test to see if your headline hits hard
- Where to put your biggest benefit
With that in mind…
I wouldn’t recommend reading this first. It’s not that difficult of a read… but the contents aren’t helpful without a grasp of the broader structure of sales arguments.
Read something that gives you that before you dive into a “tactics collection” book.
The Adweek Copywriting Handbook, Influence, or Scientific Advertising (covered later in this article) serve as better starting points.
Ca$hvertising makes more sense and offers more value once you have that foundation underneath it.
3. Positioning by Al Ries and Jack Trout
Positioning, according to Ries and Trout, is about the customer’s mind rather than your product.
Specifically, what slot your brand occupies in it relative to everything else.
The core argument is simple:
The first brand to occupy a position in the customer’s mind has an enormous advantage over everyone who comes after. Examples:
- Hertz owns “car rental” in most people’s minds
- Coke owns “cola” to the point that many colas are called “Coke” colloquially… and, in the American South, “Coke” is a stand-in for soft drinks (even non-cola ones, like Sprite)
- Kleenex owns “facial tissue” so completely that people use the brand name as a generic word.
And yet these market-dominant brands often make a huge mistake.
They get a little bit of corporate FOMO and want to expand into new products/categories (they call it “line extension” in the book, as in “product line”).
Brands that try to expand into new categories by leveraging an existing brand name often fail — even if the product is amazing — because the customer’s mind already has a fixed idea of what that brand means.
If Kleenex launches toilet paper, they’re fighting Charmin on Charmin’s turf. The brand name that was an asset in one category becomes a liability in another.
Similarly, if Charmin tried to launch facial tissue products, people would skip ‘em most of the time for Kleenex. Even people that BUY Charmin facial tissues might call them “Kleenex” or “Charmin Kleenex.”
This brings us to the other big takeaway:
If you’re not first, you have to find another way in. You can’t just show up and claim to be better than whoever already owns the position. No one will listen.
You have to reframe the conversation entirely, or own a different, more specific position.
The Avis “We Try Harder” campaign is the classic example.
They couldn’t beat Hertz at being the biggest in the rental car business. So they made second place a virtue — a reason to believe they’d work harder for your business. They owned the “underdog who earns it” position instead.
This happens to be an example of “making the skeleton dance,” one of my favorite copywriting techniques. Apply it to your brand positioning, and you could capture a good chunk of the market like Avis did.
Anyone who writes copy NEEDS to know these things. It helps you shape the messaging around your product properly and carve out/reinforce your unique positioning in the customer’s mind.
Yet I discovered this book by accident while looking for something else.
Read this, and you’ll have an edge as a copywriter, marketer, or business owner.
4. Influence: The Psychology of Persuasion by Robert Cialdini
This is one of the most cited books in copywriting circles, and for good reason.
Cialdini spent 3.5 decades studying the science of persuasion, and Influence is the result:
6 core principles (now 7, with the addition of Unity in later editions) that explain why people say yes.
Here is each:
- Reciprocation
- Commitment and Consistency
- Social Proof
- Liking
- Authority
- Scarcity
- Unity
Research and practitioner observation both back these principles.
It’s not a “copywriting book,” as it doesn’t cover “copywriting.” But the psychological principles within underpin the copy.
I use Social Proof, Authority, Scarcity, and Unity (identity/being part of a group) ALL THE TIME in my copy. If you’ve followed/subscribed to me for a while, you know I mention these a ton.
But the principle that stuck with me most was Commitment and Consistency.
Once someone takes a small action, they feel internal pressure to remain consistent with it. They’ve signaled to themselves and to others that they’re the kind of person who does this thing.
The next step feels like a natural extension rather than a new decision.
Put another way, it uses the concept of “cognitive dissonance” in a rather innocent way by ensuring customers feel said dissonance for not staying consistent.
For example, in my own life:
My church asks me to fill out a donation pledge card every year. I write down that I’ll donate a certain amount by the end of December and turn it in.
That small act of writing it down makes me far more likely to follow through than if I’d just had the intention. I’ve committed. Walking it back would feel inconsistent with who I am.
Funny enough, my priest HOUNDS us (in a friendly and joking manner, he’s a fantastic guy) about “just donating isn’t enough” if you don’t pledge, and he’s partly right for the reasons laid out here.
I’ve used this recently for a client, too. We’re growing their SMS list by offering early access to new drops in exchange for SMS signup.
All the customer does is type in their number. But now, they have to perform our desired behavior — buying — to stay consistent.
Boom.
Interestingly…
Effective propaganda and psychological/influence (*ba dum tssss*) operations uses a version of this concept.
Good propagandists rarely ask you to accept a radical worldview upfront. Think of
Pre-Suasion, Cialdini’s “sequel,” is a good read, too.
It covers various techniques for priming your customer to buy, reframing how customers think about things before you sell them something, etc.
But it’s not as good or as fundamental as Influence. If you can only read one, read Influence.
5. Scientific Advertising by Claude Hopkins
This book was written in 1923 but still holds up. In it, Hopkins made an argument that was radical at the time and is still underappreciated today:
Advertising is a science. “Creativity” may be involved, but only insofar as “creativity” entails thinking of the best possible angles.
Seems obvious….
But remember this is one of the earliest copywriting books. Everyone who talks about the scientific aspect of advertising draws from Hopkins. Anyone who runs an A/B test in Klaviyo… yeah, thank Hopkins for that.
He’s the one who created the framework around testing and measurement.
All that said, this idea resonated with me plenty.
I have an accounting background and a numbers brain. There’s something inherently satisfying about isolating variables and testing one thing against another to see what works.
But the thing I remember most vividly from this book is the Schlitz beer story.
In 1907, Hopkins was brought in to help Schlitz, which was struggling despite being a quality product.
He toured the brewery and asked questions about the process. They told him about the cold filtration, the steam-cleaned pipes, the way each bottle was tested before it left the facility.
Hopkins was fascinated. He said, “Why don’t you advertise this?“
They said, “Everyone does it that way.“
He fired back with, “But no one has said so.“
After some persuasion (what do you expect, he was a marketer), Hopkins built the campaign around the process.
He detailed the behind-the-scenes reality of how Schlitz beer was made and tied that to why it’s the best beer and worth buying.
Schlitz went from an also-ran to market leader in mere months, setting the stage for a meteoric rise and strong industry position that lasted over half a century.
You can draw a LOT from this story:
- The curse of knowledge: Sometimes, you need an external perspective to see what’s remarkable about your brand, products, etc because when you’re in the business, things that feel mundane might be fascinating and compelling to customers. If you’re not sure what I’m getting at here, think about how you stop feeling/noticing clothes a few seconds after putting them on (sensory adaptation). Same thing — you don’t see problems, good angles, etc. when knee-deep in the work.
- Positioning: Think back to Positioning a couple sections back in this article. Now look at what Hopkins did… he positioned Schlitz based on the process. It became known for that even though everyone else did the same thing. Doesn’t matter. Schlitz was THAT brand.
- Market sophistication: The market had heard claims about “the purest beer” a zillion times. That angle fatigued. If everyone says it, it’s meaningless. So the market becomes more “sophisticated”. Hopkins realized he needed to differentiate the brand after this market evolution by providing proof of the “purest beer” claim.
I will admit Hopkins is not the most thrilling writer. His writing style is curt and serious, if I recall correctly.
But there’s no fluff. It’s no more than 80-100 pages, depending on the version. Read it over a weekend and take some notes.
Grab Scientific Advertising here
6. The MOAT by Chris Orzechowski
Chris is a friend, client, and sorta mentor I’ve learned a lot from over the years. The MOAT is, in my opinion, the best of his 3 (4?) books.
He called it The MOAT after Warren Buffett’s concept of a “moat” — a distinct structural advantage that insulates its long-term market share and profits from potential competition.
But the “MOAT” stands for something:
- Mission: Who you are, what makes you different, and who you’re selling to
- Offers: What you’re selling on the front end (and on the back end)
- Acquisition: How you’re getting people to those offers
- Traction: How you’re keeping those customers around and getting them to buy again
(His MOAT here inspired my AREA² framework, which you can learn more about here.)
There’s more detail in the book, but those are the 4 big pieces that make a successful eCom business.
But it’s much more strategic. Not much on copywriting… much more on business and marketing.
The overarching theme is “essentialism,” which, in simple terms, is “do less, but better” so you can focus more time and resources on what works.
Don’t move to the next level of complexity until you’ve exhausted every reasonable opportunity at your current level.
For example, before you launch a new product, list a hundred ways you could improve your existing funnel.
Or before you hire an agency, ask whether you’ve truly maxed out what one focused person or small team can do.
Before you add complexity, make sure complexity is actually the bottleneck.
It’s a bit similar to what Eliyahu Goldratt lays out in The Goal: A Process of Ongoing Improvement. Find and fix what’s slowing things down, then move to the next.
On a related note, another takeaway from the book is that you as the founder/operator are a capital allocator. Your job is to find the projects/initiatives that’ll turn $1 into as many more $$$ as possible.
Chris, being a copywriter, wrote this in plain English with his signature style. It’s about 145 pages, but the text is big so it’s a quicker read than it looks.
This is one of two books I keep by me as a reference resource. The other is next…
7. Breakthrough Advertising by Eugene Schwartz
Full disclosure: I’ve only read the first couple sections of this book. I don’t know what the rest covers (although you could probably look that up).
But those sections alone are worth the price of admission.
This is where Eugene (Gene, for short) introduced the world to two critical concepts:
- Market awareness
- Market sophistication
Market Awareness
Market awareness describes where your prospect is in relation to your product before they ever see your copy. There are 5:
- Completely Unaware: They don’t even know they have the problem yet
- Problem Aware: They know they have a problem but don’t know there’s a solution
- Solution Aware: They know the result they want but don’t know your product can deliver it
- Product Aware: They know your product exists but aren’t convinced yet
- Most Aware: They know your product and just need a reason to buy
Where your prospect sits on this spectrum determines everything about how you open your copy and what kinds of angles you take.
The goal is to move them up the stages to nab the sale.
Market Sophistication
Market Sophistication describes how saturated the market is with similar claims. Again, there are 5:
- Stage 1: The market is new. You can lead with the bold, direct claim. “Lose 30 pounds in 30 days.” No one has said it before so it lands.
- Stage 2: Competitors have made the same claim. You have to make it bigger, bolder, more specific. “Lose 30 pounds in 30 days, guaranteed or your money back.“
- Stage 3: The claims have been made and amplified to the point of skepticism. Now you need a unique mechanism. HOW do they lose weight?. “The 3-phase metabolic reset that burns fat while you sleep.“
- Stage 4: Even the mechanisms are getting crowded. Now you need to elaborate on the mechanism, make it more specific, more credible, more detailed than competitors.
- Stage 5: The market is completely saturated and deeply skeptical. Direct claims and mechanisms no longer work. Now you lead with identification, identity, and the person — the products and claims are there, but more so as mundane features, in some sense.
An early market where no one has made your promise before lets you lead with the bold claim directly. A sophisticated market that has seen every version of that promise needs you to come in with a new mechanism, a new angle, or a new level of specificity — because the reader has heard it all before.
Think back to the Schlitz beer example from Scientific Advertising that I covered.
Everyone claimed pure beer, so the market moved up to Stage 3 (perhaps skipping Stage 2 since it’s beer). Hopkins spoke at that level by highlighting the process.
Positioning touches on similar ideas.
Market sophistication is essentially what happens over time as more competitors pile into the same position. The claim gets crowded, and late entrants have to find an entirely different position or a new mechanism to stand out.
See a throughline here?
Many of these books circle the same deep truth about marketing:
What you say and how you say it depends entirely on what the reader already knows, believes, and has been told before.
Now, this book isn’t cheap. Gene passed away in 1995 (a year before I was born), and Brian Kurtz (a friend of Gene and a top marketer himself) was handed the rights (via his company, Titans Marketing) alongside Gene’s widow, Barbara.
Since he has been entrusted with the rights, and not some giant company… well, it’s more resource-intensive to produce the book.
So the link below is NOT an affiliate link. I could send you to the $399 copy on Amazon and earn ~$18 in Amazon commissions, but I’d rather you buy it at the regular price of $125 + tax and shipping.
Still pricey? Sure. But less than half the cost, and it won’t be used.
(Psst: This is not tax advice, but it could potentially be a tax writeoff if buying for business purposes. Ask your accountant.)
Grab Breakthrough Advertising here
BONUS: Simple Email Sequences That Sell
These 7 books represent the foundation of how I think about copy, marketing, and persuasion.
Plenty of other good ones exist. I own and have read several not on this list. But we’d be here forever if I listed every last book.
Not to mention, you don’t need to read 100 copywriting/marketing books before you start writing. I’d say 3 maximum will get you mostly the way there. Any books beyond that may help reinforce concepts, but 2-3 will get you the fundamentals.
True learning after that entails hand-copying classic sales letters and writing real copy for yourself or clients.
If I had to rank them by impact, Ca$hvertising and Breakthrough Advertising would probably sit at the bottom simply because I read one too early and haven’t finished the other. Still worthy books, though.
The remaining five I’d recommend to almost anyone trying to get serious about copy and marketing. I’d start with something broader (like Sugarman and Cialdini), then tackle things like The MOAT or Positioning.
Now, there’s one more book I’d love you to have for free.
It’s called Simple Email Sequences That Sell, and I wrote it earlier this year.
It contains 10 email sequences that can boost your revenue 10-15% every month on autopilot.
Short and sweet. You could knock it out in an afternoon (and keep it as a reference guide for later).
It’s called Simple Email Sequences That Sell, and it covers 10 email automations that can unlock an extra 10-15% in revenue for your store.
Subscribe below and I’ll send it straight to your inbox.
And one more thing…
What books did I miss? What’s on your list that isn’t on mine? Let me know in the comments below.
What To Do Next
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