Then we finally learned what Amigo is all about. Adsense for newsletters. Pretty simple, but one of those ideas that strike you as “hey, that’s pretty cool, hasn’t somebody done that already?” I’ll try to give it shot, especially now that we have over 1000 subscribers to our newsletter. Maybe this will be the motivation I need to actually send a newsletter consistently.

I’m no email newsletter expert. I’ve written a total of two so far for NetworthIQ , but I can tell you I’ve learned a lot from those two times and it’s really made me consider the newsletters I read and what makes them effective.

1) Opt in is the only way
This goes without saying, but if you offer a newsletter subscription as part of a site registration, make the newsletter optional and leave it unchecked by default.

2) Use a good tool or service
I’ve spent (wasted is maybe a better term) a good deal of time researching various newsletter products and services. I examined the following options:

• Listserv setup with host ISP. Low-cost approach, but there was no way to mass import subscribers.
• Open source. The best I could come up with was PHPList, which I tried unsuccessfully to get running on a WIMP host (Windows, IIS, MySql, PHP). I’m sure I could have got it to run, but I had spent too much time already, and from I saw it looked to be overly complex for what we needed. Interesting that with PHP scripts, it’s always so much easier to find something open source. I couldn’t find any open source .Net newsletter products out there (at least unless you wanted to use DotNetNuke).
• Commercial Packaged Applications. I didn’t look too far down this road, as my budget is limited, and if I was going to pay, I might as well go with a hosted solution so I don’t have to worry about installing anything.
• Google Groups. I saw this suggested by Nick Denton in his startup kit. It’s definitely the cheapest hosted solution, but I was concerned that the service sent confirmation emails when I tested adding subscribers. This seemed like it would be a little disconcerting to users that they were signed up for some Google service without knowing about it. So, I scratched that idea. I think they’d be great for cheap internal list management though.
• Build. I haven’t ruled out building something simple ourselves, especially so that I can store archives. But, at this point, I’d rather not take the time to learn the intricacies of sending bulk email, what with ISP support and CAN-SPAM regulations. I think this is something that’s better to buy than build, but I reserve the right to change my mind.
• Campaign Monitor. There is an endless list of outsourced email providers, but most of them were prohibitively expensive for us and our needs (monthly email to 500 subscribers and growing). I’ve used Campaign Monitor both times and have to say it was one of the best web application experiences I’ve ever had. It was so simple and the app provided valuable help and insight where needed. I felt it was reasonably priced.

3) Write an interesting subject line
This is rather obvious once you think about it, but I learned it the hard way and still see other newsletters with poor subject lines. Having “Company/Product Newsletter #1″ as the subject is not very effective. Give a good tease or lead-in, entice the user to open it. Otherwise they’ll go right on by it in their inbox.

My first newsletter subject was “NetworthIQ Newsletter #1,” and the response generated from it was so quiet, you could hear a pin drop. Now with newsletter #2, I had “NetworthIQ Newsletter – Net Worth Stats Released.” Newsletter #2 featured similar content as #1, but I highlighted the Net Worth Statistics we had just released in the subject. The response was overwhelmingly better. Referrers lit up with email clients.

4) Keep it short
There’s a lot of noise out there these days. Between reading blogs, emails, etc., people just don’t have time to read a bunch of copy. Include short snippets and link to your site to provide more detail. Provide as many calls to action in the fewest words you possibly can.

5) Stick with text, don’t bother with HTML
If you follow #4, there’s really no reason to have HTML. It just adds complexity. Most HTML newsletters utilize images extensively, but in case you haven’t noticed, Outlook 2003 and Google Mail both disable images by default. Why bother dealing with this? Need a link? Well, most email clients turn a textual URL into a link anyway. Keep it simple and keep it text. Besides, what are most blogs syndicated as? Text. I’d argue that’s what makes them successful since it cuts out the crap and gets right to the guts. Now in the event that you want to do some tracking and place a web bug, HTML is probably fine. Just stay away from images.

What do you think? What’s effective for your newsletters?

Additional tips you may find useful:

• http://www.campaignmonitor.com/blog/archives/2005/11/html_email_desi.html
• http://www.useit.com/alertbox/20020930.html