In this episode, we discuss email marketing, focusing on how to avoid spam filters when sending emails. We often emphasize that email is gold, but if it gets caught in a spam filter and doesn’t reach your reader’s inbox, it’s ineffective.

We’ve frequently discussed the importance of email on this podcast. We’ve covered what to do, and now we’ll tell you what you should never do.

Are you a spammer?

Jim: Should people ask themselves, “Am I a spammer?” Some don’t think they are, but they might be.

Thomas: Most spammers don’t realize they’re spamming. Spam is in the eye of the beholder.

Every inbox has a “Mark as Spam” or “Mark as Junk” button. If someone clicks it, you’re labeled as spam. You might think, “What’s the big deal?” It’s a big deal for two reasons. First, it could be illegal, potentially landing you in trouble with the U.S. government. You don’t want jail time or fines just for promoting your book. The government already makes life challenging enough without breaking the law. Second, and perhaps worse, you could be punished by Google. If someone marks your email as spam in Gmail, you’re flagged as spam for all Gmail users. You might say, “That’s unfair!” But you sent the email that got marked.

It’s not always a one-to-one ratio. It might take two or three people marking you as spam, but it doesn’t take many. When someone clicks “Mark as Spam,” it’s not just a slap on the wrist; it’s a punch in the face. They’re telling their ISP, “This is spam for everyone,” not just themselves.

How does an ISP know an email is spam?

Think of an email as a paper envelope. The ISP first looks at the outside of the envelope, asking questions:

• Is the sender’s domain reputable?
• Do I trust the sender’s server IP address?
• Is the server in a “bad neighborhood”?

Jim: If you’re using cheap hosting, you might end up in a bad neighborhood. Even if you’ve done nothing wrong, if your server neighbors are spammers, the ISP might think, “Hmm, what’s this guy doing here?”

Thomas: There are three categories: known to be good, known to be bad, and bad neighborhoods. You want to stay out of bad neighborhoods. The ISP also checks if the recipient has opened or responded to emails from the sender before. Some people beg you to add them to your address book because they’ve been marked as spam and are trying to climb out of the spam folder.

The second thing the spam filter does is read the email itself to see if it “smells” like spam. It asks:

• Is the HTML clean?
• Is it one big image?
• Is there a plain-text version?
• Does it use words spammers typically use?

How can I avoid the spam filter?

Tip #1: Use Double Opt-In

Jim: The first tip is the double opt-in. We usually say don’t make readers jump through hoops, but this is an exception worth making. It’s like inviting someone to dinner: “Thomas, want to come over?” “Yes.” “You really want to come?”

Thomas: “Yes, I really want to come over.”

Jim: “Okay, then come on over!” You’re confirming they know what they’re signing up for. Even then, some people sign up for my newsletter via double opt-in and then unsubscribe, claiming they never signed up, which is impossible because of the double opt-in process.

Thomas: Double opt-in is critical for several reasons. Without it, someone could accidentally or maliciously subscribe to a list. For example, a prankster might sign someone up for thousands of newsletters. There’s a story about a professional spammer whose name got leaked online, and a community signed him up for 6,000 paper catalogs. Now, his mailbox is flooded daily with 30 pounds of catalogs. Robots can also auto-fill email forms with random addresses, or someone might mistype their email and accidentally subscribe you. In these cases, people might mark you as spam because they really didn’t sign up. Double opt-in prevents this 100%.

Another reason is that email marketing service providers keep a record of double opt-ins. If someone marks you as spam, you can show Google, “No, this was an accident, or they’re using spam as an unsubscribe.” This might earn you some leniency from the “Google gods.”

Tip #2: Include a One-Click Unsubscribe Option

Thomas: It takes one click to mark an email as spam, so if unsubscribing takes two clicks, people might choose the easier option, which is to mark you as spam.

I don’t like Constant Contact because unsubscribing requires typing your email address, which is tedious, especially with long names like Umstattd. I’m tempted to mark it as spam because Constant Contact will auto-unsubscribe me if Google reports it, but I know that hurts the sender, so I don’t. One-click unsubscribe is much better, and it’s as easy as marking spam.

You want people to unsubscribe.

First, you pay for subscribers. Every professional email tool charges you based on your subscriber count. If someone isn’t opening your emails, you’re wasting money. At Author Media, we periodically unsubscribe people who haven’t opened our emails in a year because we don’t want to pay for them. We want high open rates and engagement.

Second, if they don’t unsubscribe, they might mark you as spam, which is far worse. Make unsubscribing as easy as possible.

Tip #3: Email at Least Once Per Quarter

Jim: Once every six months isn’t enough. We’re not advocating daily newsletters, but anything less than quarterly is too infrequent.

Thomas: I had a client who was a popular speaker who filled arenas. For years, he collected email addresses in person but never sent emails to them.

When we finally sent an email via MailChimp, some recipients had forgotten him. They thought, “Who is this?” and marked it as spam. We got banned from MailChimp despite having handwritten sign-up forms. We appealed, but too many spam reports sent us to “exile.” It was awful.

You need to email frequently enough to stay familiar to your readers. If you release a book yearly, you might get away with an annual email, but at least send a Christmas or July 4th message. It can be something benign that’s unlikely to be marked as spam, but it will keep your name recognizable.

Tip #4: Write Intriguing, Non-spammy Subject Lines

Thomas: The subject is critical for open rates and is one of the first things spam filters check. Make it legitimate but compelling, as more opens increase your chances of landing in the inbox.

Tip #5 Avoid “Bad” Words

Jim: We’re not talking about curse words, but salesy terms like “100% satisfied,” “bargain,” or “free.” These trigger spam filters because they’re common in spam emails.

Thomas: There’s a list of about 100 trigger words that change over time. Search “spam trigger words” on Google for the latest list, or check your spam folder and avoid words in those subject lines. For example, “penny stocks” used to be a big spam topic, but trends have shifted. Stay away from words spammers are currently using.

Tip #6 Use a Trusted Sender

Thomas: Use a trusted sender with a good reputation that will ensure delivery to inboxes. (NOTE: Thomas no longer recommends MailChimp. Find out How to Pick the Right Email Service for You and what Thomas currently recommends.)

Never blind carbon copy (BCC) large groups from your personal email. This is a disaster. It flags your personal email as spam, potentially breaking it. Recipients can’t see the sender’s email or unsubscribe easily, so they mark it as spam, especially if they only met you once and feel awkward asking to unsubscribe. If you’re BCC’ing multiple batches of people in your contacts, stop immediately. There’s forgiveness. Just don’t do it again.

Tip #7 Avoid Using All Caps

Jim: All caps feels like shouting, and no one likes being shouted at. I was in a group email where one guy always used all caps, and everyone got tired of it.

Thomas: It’s worse when someone accidentally leaves caps lock on, not knowing it’s shouting. All lowercase letters are better but still unprofessional. Stick to standard capitalization.

If you follow these rules, you’ll stay out of spam folders, and your emails will be delivered. I still believe email is the most effective online tool for promoting your books.

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