• by Jonathan Blum , June 28, 2006

What does it take for a career gadget guy to get his weekly e-mail newsletter to a small group of people? Too much. I learned the hard way what many small businesses face when they try e-mail marketing. I recently launched Blumsday, an e-mail newsletter filled with my musings on the latest and greatest devices.

I quickly experienced a raft of problems. My graphics get abused. I can't send photos. Sometimes my mail gets through, sometimes not. The Web often can't tell my newsletter from Viagra ads. I run afoul of spam lists and get blacklisted.

"Most small businesses get that sort of deer-in-the-headlights thing when it comes to newsletters," says Gail Goodman, CEO at Constant Contact, an e-mail marketing firm in Waltham, Mass.

She's right. I can't seem to solve my problems with the e-letter. I have burned through three designers, three pr people, and likely a couple of clients. My copy editor works mostly for love of craft. And I am most definitely not alone.

"The problems you're experiencing are the same problems most marketers are having with e-mail," says Bill McCloskey, CEO, E-mail Data Source, a New York-based e-mail research firm.

Vastly more than 100,000 businesses and organizations use commercially marketed newsletters. So I assumed that a Microsoft Word document I write daily for my vendors and partners would be simple enough to distribute online.

Innocent, ignorant me.

Probably nothing is harder to send online than a Word file attached to a Microsoft Outlook e-mail. Microsoft embeds content in its e-mail, leading to clashes with rival companies' operating systems, e-mail programs, and word processors.

"It takes years of learning what can and can't be done with e-mail to know what will work," says Judah Wiedre, account manager at Sublit, a New York-based e-mail marketing and design firm.

Then there is the mailing. There are two big roadblocks to reliable sending. First, e-mail programs mistakenly identify messages, including mine, as junk; the programs then automatically send the messages to a junk e-mail box to die.

The second problem is that once an e-mail is marked as junk, the Internet service provider makes note of the sender and tells other ISPs, whose vast staffs and programs snag junk e-mail and stop spammers.

"It used to be you could be sneaky about your e-mail," says Steve Webster, president of iPost, a Novato, Calif.-based e-mail marketing company. "No more. Now all the big ISPs distribute real-time blacklists."

Voila! I'm on the unwanted e-mailers list. Contacts I've known for years can't get my newsletters. Some can't even get my personal e-mails.

As the e-mail marketing industry looks to the future, I must ask: Is it good that a sole proprietor like me cannot e-mail his friends and colleagues? Unclogging the Web sounds like good business in the short term. But in the long run, does the industry really win if the open Internet closes because of its own clutter?