This is it, you say to yourself. You’ve drafted a strong letter for your direct mail donor acquisition mailing. It’s clear. It’s compelling. It invites prospective donors to join the cause by making a gift today. And it’s ready for approval. So you take the letter to the head of your nonprofit—but you don’t get the green light. “It’s too repetitive,” you’re told, “Too simple. Too gimmicky. It needs more substance.” The letter is handed over to your organization’s prize-winning research fellows and programs department for an overhaul, and it comes back with more “substance” and fewer “gimmicks”: no more underlining, “red meat” copy, or bolded postscripts with suggested gift amounts. When the letter hits mailboxes, it’s dense with facts, figures, erudite historical reflections, and penetrating commentary on the wider culture—the kinds of insights that have made your organization a go-to resource for your cause. And it tanks. Your campaign winds up with a low response rate and sad average gift size, and you wonder what went wrong. The moral of the story is this: Fundraising writing is an art. And like any art, it must be studied. Anyone can do it—but it takes knowhow. Direct mail fundraising has its own body of knowledge, its own set of principles, and a litany of dos-and-don’ts derived from decades of personal experience and testing within the field. Let’s add a corollary to this: Expertise in research or program writing (or any other kind of writing) is no indication of expertise in fundraising writing. In fact, it can sometimes be detrimental. Why? Because at first glance, many principles of fundraising writing are counterintuitive, like the fact that good direct mail copy, especially prospecting copy, is gimmicky. This doesn’t mean good direct mail copy is deceptive or polemic. It does mean that good direct mail copy makes liberal use of certain rhetorical techniques to help win hearts, minds, and donations. A prospecting letter is a specific kind of persuasive vehicle. It uses the written word to inform and involve readers and move them to action: to make a gift, to complete a survey, to join a community. And it has a very small window of opportunity to accomplish this goal. Most prospecting letters are opened and skimmed by someone standing over a waste bin—so repetition and simplicity are essential. It’s worth reflecting on this point. It’s easy to see how the repetition of simple ideas can be condescending and irritating. When used artfully, however, repetition and simplicity are the two most important elements of persuasion. The ancient masters of rhetoric—the Sophists, Aristotle, and Cicero—codified many effective rhetorical figures of speech that rely on the repetition of simple ideas. Figures such as anaphora (the repetition of an opening word or phrase) and epistrophe (repetition of an ending word or phrase) are ubiquitous in politics and advertising today—because they work. For good or ill, studies show that just repeating your take on a topic makes it more likely that others will come around to your position. Repetition prompts a response from the listener or reader by making key ideas memorable and unavoidable. Think of Winston Churchill’s stirring use of anaphora in the conclusion of his speech to the House of Commons in 1940: “We shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills; we shall never surrender…” Quotes like this remind us that, when the right message finds the right audience, repetition is highly effective and even enjoyable. “Repetition, the re-experiencing of something identical, is clearly in itself a source of pleasure,” as Sigmund Freud observed. Most of us have favorite songs we listen to over and over again, or movies we like to re-watch, or stories we never tire of hearing. The bottom line is that the repetition of simple ideas is intrinsically persuasive and even pleasant, and it’s a technique you can martial for good. When doing direct mail, look at the values that unite your organization and its supporters—dedication to Constitutional ideals, commitment to the poor and marginalized in your community, etc.—and touch on these points of commonality again and again in your letter. Keep it simple and keep it concrete. The goal of a donor acquisition letter is to convince the reader to stand with your organization by making a generous gift. So you need to say that—again and again. Invite the reader to make a gift on the first page, ask for a gift multiple times throughout the letter, and use the postscript to remind them about making a gift. Of course, writing fundraising copy that is artfully repetitive and simple takes hard work and humility. It can be difficult to rein in your thoughts and submit to the direct mail fundraising framework when your organization has a great deal of insight to offer on an issue. (The temptation to completely forgo fundraising techniques and use prospecting letters to expound on research results and projects is especially strong for think tanks.) Yes, a prospecting piece needs substantial information about your organization’s values and activities. It must be remembered, however, that the primary goal of the letter is to persuade a prospective supporter to take some action (make a gift) which will bring the reader into the life of your organization. Everything in the letter should move towards this goal. That’s a difficult task—and why it often pays to prefer experienced copywriters over research fellows and program officers when it comes to direct mail donor acquisition. The basic formula, though, is straightforward: (1) Use short, simple words to create a vivid picture of a real problem/need your organization addresses. (2) Use short, simple words that show how the reader can really contribute. (3) Repeat steps 1-2. Again and again. Is it gimmicky? You bet. But it’s also honest, clear, and grounded in time-tested techniques and principles of classical rhetoric. Most importantly, understanding direct mail prospecting as a persuasive craft with its own set of rules and best practices (no matter how strange these may seem to the layman) will remind you to focus on the hearts and minds of the people who read your letters. For persuasion, the art of producing conviction through rational and emotional appeals, ultimately centers on the person—and so should your fundraising. Spencer Kashmanian helps purpose-driven organizations achieve their fundraising goals, craft clear and compelling communications, and achieve greater influence. He manages American Philanthropic's direct response group, which offers a simple, transparent model to nonprofits, making direct mail and digital fundraising easy and successful.  You can contact him with inquiries about fundraising at