Building an Email Marketing Strategy in the LISTSERV Era

In early 1999, “setting up email marketing” mostly meant one of two things: finding someone on staff who could run mailing list software like LISTSERV or Majordomo, or paying a young hosted service like Yesmail or Roving Software (the company that would later become Constant Contact) to handle the sending for you. There was no template library, no drag-and-drop editor and no dashboard showing open rates in real time. Building a strategy meant making a series of deliberate choices before you sent a single message.

Step 1: Decide who gets on the list

The instinct in 1999 was to buy or scrape as many addresses as possible, since lists were often sold outright by list brokers. Resist it. Seth Godin’s book “Permission Marketing,” published in May of that year, made the case that had already started proving out in practice: messages sent to people who asked for them got read, and messages sent to people who didn’t got deleted, reported or worse, got your domain blocked by an ISP. Start your list with people who filled out a form, replied to an email or handed you a business card and said yes.

Step 2: Pick your sending infrastructure

If you had technical staff, self-hosting a list on LISTSERV or Majordomo was cheap and gave you full control, but it meant managing your own mail server’s reputation, something almost nobody thought about yet. If you didn’t have that staff, a hosted provider cost real money but handled the plumbing. Either way, check what your recipients would see: most people in 1999 were reading mail through Eudora, Outlook Express or a free webmail account like Hotmail, and none of those clients handled HTML reliably. Plan for plain text first.

Step 3: Write for a skeptical, novice inbox

Most of your subscribers had only been using email for a year or two. Subject lines needed to say plainly what was inside, since curiosity-driven subject lines just looked like a scam to someone still new to the medium. Keep messages short, put your point in the first two lines and never assume a recipient would scroll.

Step 4: Set a cadence you can keep

A monthly or biweekly newsletter beats a promising weekly one you abandon after six weeks. Consistency mattered more in 1999 than clever timing, because your subscribers were forming their first opinions of what email from a business should feel like, and an erratic sender taught them to stop paying attention.

Step 5: Track what’s trackable

Open tracking via invisible pixels existed but was unreliable, since many mail clients didn’t load remote images automatically. What you could measure well was clicks: unique links per email, tied back to whatever offer or article you referenced. Use that as your real signal, not guesses about who opened what.

Step 6: Make leaving easy, even though no law says you have to

There was no federal law in 1999 requiring an unsubscribe option or a real postal address in your emails. Include both anyway. ISPs like AOL were already building spam complaint systems, and a subscriber who can’t find a way to leave will hit “report spam” instead, which does far more damage to your ability to reach an inbox than a clean unsubscribe list ever will.

Put together, none of these six steps require a big budget. They require patience and a refusal to treat your list as a shortcut around building something people want to hear from.