I asked Gemini to clean up the transcript: 

Marketing Mentor Podcast: Ann Handley on the Art of the "Letter"

Introduction

Today I’m bringing back one of my favorite conversations from the archives — my interview with the brilliant Ann Handley about how to write ridiculously good email newsletters.

No wonder it’s one of my most popular episodes. 

Ann is the one who said my very favorite thing about newsletters – that it should be more letter than news. And she practices what she preaches, through her own fortnightly newsletter. (Mine is also fortnightly, which is the perfect frequency, if only because we get to use the word fortnightly!)

And even though this conversation was recorded several years ago, it’s more relevant than ever in 2026. In a world of algorithms and AI, your email newsletter is still one of the best ways to stay in touch with your people and build real relationships.

Don’t ever forget: your creative business is a relationship business.

In this episode, Ann shares simple, practical ideas for writing newsletters people actually want to read — how to find your voice, what to include, and how to make your emails feel human instead of promotional.

So if you’ve been meaning to start a newsletter — or revive a dormant one — this episode is for you. I do hope it will give you the inspiration you need to get it going again. And feel free to put me on your list.

Anyway, you’re in for a treat – so listen and learn.

Welcome to the Marketing Mentor podcast with Ilise Benun, founder of marketing-mentor.com and author of seven books, including The Creative Professional’s Guide to Money. Since 2008, Ilise has been interviewing her clients and successful professional creatives who are doing what it takes to stop the "feast or famine" syndrome, get better clients, and command the fees they deserve.

Ilise Benun: If you’ve been following me lately, it’s hard to miss my ranting about email newsletters. They are the single most effective marketing tool I use. If you do nothing else to market your business, I implore you: please send out an email newsletter to everyone who knows you.

All this ranting was triggered by Ann Handley’s compelling opening keynote at the AWAI copywriting boot camp. That’s when I heard her say: "Email newsletters are not about the news; they’re about the letter."

The proverbial light bulb went off. I was so jealous! Of course, it’s about the letter. Why didn’t I think of that? Today, I am thrilled to have Ann on the podcast. We bonded over our mutual obsession with email newsletters. We talked about how to write ridiculously good content—the subject of Ann's bestselling book, Everybody Writes—and the art of curating content for those who insist they can’t write.

Hello, Ann. Welcome to the podcast.

Ann Handley: I am so delighted to be here, Ilise. Thanks for having me.

Ilise: Please introduce yourself.

Ann: I’m Ann Handley. I am an author and speaker. I am the world’s first Chief Content Officer, and I am obsessed with email newsletters.

Ilise: That’s exactly why we’re talking. I’ve been wanting to call "newsletters" something else lately because I find the words themselves are an obstacle. How do you define an email newsletter?

Ann: A lot of people and brands think of the email newsletter as a distribution strategy. They focus on the "news" piece because they have something they want to tell their audience. It feels very one-way.

I think the real opportunity is in the second part of that word: the letter. You should reframe the idea. It’s not something you broadcast; it’s a letter you write directly to one person on your email list. Your inbox is an inherently personal place. You don’t want to feel like what you’re reading was broadcast to a crowd; you want to feel like it’s to you.

Ilise: Most of what is in my inbox does not feel like it’s to me. When I do see something personal, it feels rare. Do you find that too?

Ann: For sure. This started for me about a year and a half ago. A subscriber told me, "I only got four posts from you last year." I tried to wave him off, saying I was busy, but he said, "Why aren't you using this platform? I want to know what you’re doing and what you think."

He hit on a fundamental truth I didn't want to hear. I asked myself: why an email newsletter? In the age of Facebook Live and podcasts, does it have to be a newsletter? My thinking evolved to this: the email newsletter is the only place where people, not algorithms, are in control. It's where individuals decide, "Yes, I want to hear from this person."

Ilise: My newsletter is also my most effective tool. But most people ask, "Why would anyone want to read my newsletter?" or "What do I have to say?" How do you respond to those obstacles?

Ann: Your audience doesn't necessarily want to hear about you; they want to hear about how your business can help them. People are inherently focused on their own lives. If you make your communication useful and valuable to them, they will care.

The reframing I went through is asking: What does my audience need? If I missed a Sunday, would people write to me and ask if I was okay? That’s the bar I use. We want to be so valuable that we would be missed.

Ilise: How do people find out what is important to their audience?

Ann: There are many ways. When someone signs up for my newsletter at AnnHandley.com, they get an auto-responder that asks: "Why did you sign up? What do you hope to learn here?" About 20% to 30% of people actually hit reply and tell me their struggles. I put those responses in a spreadsheet. When I sit down to write, I riff through that to see what's on their minds.

Ilise: You also do "shout-outs" and share resources. Even if that’s all someone did—curation—that could be enough, right?

Ann: Absolutely. But there’s an art to curation. It’s not just dumping links. Each of my newsletters has a theme or a "through line." I don't just say, "Here is an article about blog posts." I say, "Here is why this is valuable to you in 2019." Adding the "why" and your own voice is what makes curation valuable.

Ilise: Let's talk about the idea that Everybody Writes. For people who think they can’t write, what is the core idea there?

Ann: I wrote the book because so many people have "writing trauma" from childhood. My fundamental belief is that everyone is a writer now. If you write emails, social posts, or blogs, you are sharing your story through text.

If you're an "adult-onset writer" who is uncomfortable, don't sit down in front of a blank page. Open a recording app and just talk. Get it transcribed (I use Rev.com), and then sit down a second time to edit it for clarity.

Writing, at its root, is just clear communication. Don't think about it as "Writing" with a capital W; think about it as communicating with someone you have something important to tell.

Ilise: Your newsletter is called Total Anarchy, and you send it early Sunday mornings. Why?

Ann: Email is a place where people have opted in to hear from you. If the goal is deeper engagement, I think you should send it at "off times." On Sunday mornings, I picture my readers lounging on the couch with a coffee, opening their phones, and having a few moments with me. I want to create an experience they can relax into.

Ilise: Beautiful. Thank you so much, Ann.

Closing

If you want more from Ann, sign up for her newsletter, Total Anarchy, at AnnHandley.com/newsletter. And if you don't already get my Quick Tips, you can sign up at marketing-mentortips.com. I’ll be back soon with more conversations on how to overcome the feast or famine syndrome.