NO MATTER IF you're starting up a bricks-and-mortar retail store or a home-based business, crafting a quality email newsletter should be high on your list of priorities. But how do you make sure your newsletter doesn't land in your potential customers' spam folders?

Jennifer Tankersley, founder of ListPlanIt.com, a subscription site that offers hundreds of "to do" lists and planners, is taking some extra precautions. Last May, right after she launched her company, she began emailing her "L.I.S.T." newsletter (which contains tips for the organizationally challenged) as a way to boost her site's subscribers and advertising revenues.

When customers sign up for her newsletter, Tankersley makes sure they get an automatic note, reminding them to add her to their "safe senders" list. She makes sure her newsletters don't contain words (like "free" or "compare") that trigger antispam filters. And she includes either her name or her company's name in the subject line. "The more people I can get to come to the site, and the more people that sign up for my newsletter, the better," she says.

In recent years, more business owners like Tanskersley have turned to email newsletters as a cost-effective way to deliver their company's message and build relationships with readers. Indeed, from a marketing standpoint, "having a newsletter — provided you [deliver] value to your reader — is a great way to gently remind past or potential clients about your company, your services and your expertise," says Jennifer Shaheen, a technology consultant in White Plains, N.Y.

But doing anything via email these days can be cumbersome and, thanks to spam blockers, useless. "Everyone's having a problem with this," says Ronen Yaari, president of OpenMoves, a boutique email marketing firm in Huntington, N.Y. While it isn't precisely known what percentage of newsletters land in consumers' spam folders, he estimates that the average newsletter gets opened just 15% to 25% of the time.

Of course, some newsletters go unopened simply because recipients aren't interested or don't have the time to read them. But if you want to make sure your newsletter arrives safely in a potential customer's Inbox, follow these steps.

Getting Started

To develop spam-free newsletters, seek professional help from a company that specializes in email marketing, suggests Richard Rabins, co-chairman of Alpha Software, a Burlington, Mass., database software maker. In addition to OpenMoves, email marketing firms such as Constant Contact, Bronto and VerticalResponse take care of "back-end" mechanics, he says. That includes providing newsletter templates, tracking and antispam tools, which can reduce the likelihood that your newsletter ends up in customers' spam folders.

Marketing firms typically send your newsletters via proprietary Internet Protocol (IP) addresses or they’ll give you your own, Rabins adds. This is a positive feature as these companies regularly cleanse their networks of spammers or even risky senders. They also maintain close ties with Internet service providers such as MSN, AOL, Google and Yahoo, which use antispam filters to block bad IP addresses at will. "If the source of a newsletter is a respected known entity, it'll go through," he says.

While basic packages typically start at $15 or $25 a month, prices will vary with the level of service provided. More robust offerings typically include preview and testing capabilities. OpenMoves, for example, offers to show your newsletter to focus groups while Bronto provides its high-end clients with reports showing a customer's account usage and overall campaign performance. (You can also send emails to as many as 100 recipients each day for free via SendBlaster, a bulk email software.)

Tripping Up Spam

When writing your newsletter, make sure you know what words to avoid, says Shaheen, the consultant in White Plains. That's easier said than done, as the list of words that can be flagged as spam is "growing all the time," she says. "Words that you would not even think are triggers can put you in someone's junk email folder." For instance, phrases such as "stop snoring" and "search engine listings" and even words including "laws" and "business" can trigger antispam filters. To keep up with newly discovered spam words, she suggests typing the term "spam words" into your search engine and then steering clear of them in your newsletter.

Also, Rabins suggests running newsletter emails through spam checkers such as those provided by email marketing software provider Lyris, eDisplay's Mailing Check, or the Email Sender and Provider Coalition’s spam checker.

Be sure to also request that newsletter recipients add your address to their safe sender list, as Tankersley of ListPlanIt.com did. Also, make sure the code you use to create your newsletter is error-free and follows some widely accepted standards called W3C HTML guidelines. When you simply cut and paste a Microsoft Word document into an email and hit send, Yaari from OpenMoves says, the code may not translate cleanly, which can cause rendering issues. For example, instead of an apostrophe a reader might see a question mark. Bad code, he adds, can also trigger antispam filters. (Click here to validate a newsletter's HTML code.)

Focusing on Design

If you must use a term (such as "free") that's considered a spam word, it's a good idea to implant those words into the images that appear within a newsletter, Shaheen suggests. The reason? Antispam filters can't detect words that are inside of images. While you'll be able to get around the spam problem, the risk with sending image-infused newsletters is that people often have to literally open an image in order to see it in an email. If users have to click on anything — especially if they're not familiar with the sender — chances are they won't, says Shaheen.

A better idea, suggests Yaari, is to create newsletters that combine images and text. That way, he says, recipients who won't see the image will still be able to read the message. And, once they know what the newsletter is about, they may open up the image.

Including a table of contents near the top of your newsletter will also improve your newsletter's chance of being read, notes Yaari. Be sure to incorporate plenty of white space and use graphics sparingly. Also, include an unsubscribe option and plenty of links, which can help increase traffic back to your site and help you track popular content, he says.

Rabins recommends keeping your letters short — that is, 700 to 1,000 words — and making them as readable as possible. The text should be short and written in digestible chunks. Make sure your language is both punchy and pithy. Additionally, keep your subject matter as relevant to your readers as possible. "The more personalized [a newsletter] is, the more relevant it will be," says Rabins. "That uniqueness," he adds "is a factor that helps get emails opened."

Other recent Starting Up columns:

• Starting Up: Attracting Luxury Shoppers
• Starting Up: Teaming Up With Other Businesses

("Starting Up," a weekly column written by Diana Ransom for smSmallBiz.com, follows entrepreneurs through the early stages of launching a business. Write to her at dransom@smartmoney.com.)