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URGENT: Bussiness moneys for you Dear, sir!! A Reformed Spam Writer Helps You Stay Out of the Junk Folder

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Confession: I used to get paid to write spam.

It was about 10 years ago, before we all knew that an email from "Your friend Sally" is probably not your friend Sally, but some dude in a Nairobi Internet café trying to scam you out of your hard-earned money. Or, as the case may be, a 26-year-old woman in a cubicle at a Boston company that is now out of business.

I know I'm not supposed to admit this, but I loved this job to distraction—even though I hated myself at the end of every day. I was just so good at it: The emails I wrote always got huge response rates.

I even heard from the sales team that one particular email moved a customer to tears. It was my "true life story" of meeting my granddaughter for the first time. (I was trying to sell a knitting magazine. I knew my demographic.)

In my defense, masquerading as "Your friend Sally" to get you to buy subscriptions to Needlepoint Now, Bird Talk, or the other hundreds of magazines we peddled was a step up from my previous job: writing telemarketing scripts for a product called Brain Gum. (I promise I'll write a blog post about that job soon.)

Those days are gone. I now run a respectable company with my respectable business partner and have a stable of respectable clients.

And though I sometimes miss my life on the dark side, I know I got out just in time. If you know anything about email marketing, you know it's a tough business these days—even when you're selling a legit product or service. Why? We're all just so savvy now. And we have really smart spam-filtering software that helps us if we're not.

Spam filters in most email software programs comb incoming emails for signs of spam and assign points when they see such red flags. The points get totaled. And if the point total is high enough, the suspect email bypasses the recipient's inbox and goes straight to the junk folder.

How good is this software? A little too good: According to Mail Chimp, about 10%-20% of all emails you send—even to people who requested them—will get accidentally routed to the junk/spam folder. What about that other 80%-90%? Those emails may not be spam, but they will have definitely broken some of these rules:

  1. Always spell-check. Just like your high school English teacher, spam filters penalize messages for poor spelling and grammar. Poor formatting gets flagged, too.
  2. Use exclamation marks with caution—and never in the subject line! One is OK, but several? Wow, are you in trouble!!!!!!!! SAME GOES FOR ALL CAPS.
  3. Avoid spam trigger words/phrases. According to Spam Assassin—a popular spam filter with the most awesome name ever—here are a few to avoid: "CLICK HERE!," "FREE!," "BUY NOW," "WHY PAY MORE?," "URGENT MATTER," "MONEY BACK GUARANTEE," and, interestingly, anything that looks like a mortgage pitch. (You can see more here.)
  4. Don't use colored or oversized font. "What do you mean, you didn't get my email, Grammy?"
  5. Avoid salesy or nonspecific subject lines. This is going to sound totally radical, but your subject line should—surprise!—actually tell the recipient what the subject of your email is. Try to be too clever, and the email will get flagged.
  6. Don't use anything but words in the subject line. This means no quotation marks, toll-free numbers, dollar signs, percent signs, or (as we have already learned) exclamation marks.

Finally, if you don't want to be flagged as a spammer, then don't send spam. Or at least don't make it sound like spam. The above tips will help.

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Anna Goldsmith is a partner at the Boston-based copywriting agency The Hired Pens ( Reach her via and 617-359-8133.

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  • by Amy Hausman Tue Aug 10, 2010 via web

    Great reminder article to review what and how you write for your everyday emails and mass-mailed marketing emails. It's amazing how many times you call someone or someone calls you and asks, "Didn't you get my email?" and it turns out it's in the spam folder....

    We're sharing your article with our blog readers (real estate professionals at whose business depends upon emails getting directly into inboxes.

  • by Wayne Patterson Wed Aug 11, 2010 via web

    Our sales personnel don't sent emails unless someone requests a reply. However we find that most of our emails are unanswered which begs the question, are they receiving them?

    Our emails tend to have attachments, also our profiles on LinkedIn, Facebook, Twitter as well. Does that make a difference?

  • by Amanda Brandon Wed Aug 11, 2010 via web

    This was so entertaining. And, great lessons on how to stay out of the SPAM folder. Thanks for sharing.

    To Wayne's point of whether to have attachments or not - do you mean PDFs or images for tracking purposes? I think unless you have an established relationship - attachments are off limits. It's safer to send a link in the email. Plus, you can track more if it's a link versus an attachment.

    Also, I'm intrigued with your email method - are you using emails to generate leads or just as a reply mechanism?

  • by Carolynn Tue Aug 17, 2010 via web

    Please don't get me started on spam emails. Some of them are so ridiculous I just have to laugh. Does anyone really, seriously read and believe a message sent to them from Dr. Amsawyah Alababbi, the Chief High Priest from the Kingdom of Osweto? Rife with misspellings and bizarre convolutions of syntax? Sometimes when I'm really really bored I will actually look at one of these absurdities and fall on the floor at the blatant, alternative-universe message it contains, and try my best to fathom how anyone with even a pea-sized brain could embrace this as a bona fide email from a real person. That's what I was hoping to read here--I already knew all the stuff about no exclamation points and the list of forbidden words and weird subject lines. This is actually quite an intriguing topic and Anna, I encourage you to do the intended blog post you mentioned. And the one about Brain Gum also sounds like a blog worth writing. Brain Gum? Really?

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