How Not To Promote Yourself on EmailS

Two years ago, internet entrepreneur Jason Calacanis quit blogging to escape angry commenters. Instead, he would publish only by email. He's since become a case study in how not to use the medium.

As a communications channel, email certainly has its uses. It's great for arranging meetings, sending compliments, and maybe even the occasional coldhearted breakup.

As a publishing medium, though, email leaves a lot to be desired. There's no way to revise a piece of information once you hit "send." It's hard to tell how many people actually read what you wrote. And getting your message past spam filters gets ever more complex and time consuming as your subscriber list grows.

Then there's the ever-present possibility of exploding your recipients' inboxes, as Calacanis just did. Last week the Mahalo CEO was complaining, ironically enough, about how Facebook had become "a waste of time for me." But his email, titled "I'm deleting my Facebook page," itself became a waste of time for his 23,000+ subscribers when some members of the list replied to the list, and when Calacanis' misconfigured software let them through. Dozens of replies piled up under the original missive from Calacanis.

How Not To Promote Yourself on EmailS

The upshot: 800 people unsubscribed, and inundated Calacanis with messages like, "Get me the F-ck off your list," according to the entrepreneur's latest mass email.

I can't tell you how bad I feel about this, and I want you to know we take these things seriously. I've never had a mistake like this since I started using email lists back in 1996 with the Silicon Alley Reporter.

I am very, very sorry and will do everything I can to make sure it doesn't happen again. Additionally, I will put a LOT of extra effort into the email list to make sure that every email has massive value for you.

Or Calacanis could just return to publishing on the Web, the communications medium actually designed to do what he's trying to do. Not that we expected the bullheaded businessman to do so, two years after he stormed off the Web in a huff. Calacanis insistence on plowing forward with Mahalo—still unprofitable, three years after it was started—after all. But at least his woes will server as a warning to the surprising number of prominent bloggers, including revered tech essayist Joel Spolsky, who have been thinking about following in Calacanis' old-school footsteps.

[Top photo of Calacanis by Joi Ito]