How do I send periodic email to a large number of people?

A personal email account is the wrong solution for this problem,
particularly if it’s Hotmail, and particularly if you actually want
your messages to be delivered.

There are several approaches to the general problem of sending large
numbers of emails periodically.

Do it yourself – direct: this is the approach
you’re trying. Basically, this means simply using an individual email
account to send the email.

As you’ve already encountered, there can be problems with this
approach. Because Hotmail has been abused so much by spammers, they’ve
instituted “rate limits” on the number of emails you can send at once,
and the number of emails you might send in a day. Many other ISPs also
have similar limits for similar reasons.

If what you’re doing is well under those limits, this might
be an appropriate approach, however I would throw out two additional
caveats:

• Don’t use free accounts like Hotmail – since these
  are what spammers tend to abuse the most, you’re more likely to be
  flagged as spam simply by virtue of having used these services. And
  using free email accounts looks less professional.

• Use BCC – send the email “To:” yourself, and then
  “BCC:” your recipients. This keeps the email cleaner, and doesn’t
  expose everyone’s email address to everyone else – an important privacy
  consideration.

Online Groups and Free Services: a surprisingly
effective solution for many folks are to use on-line discussion groups
like Yahoo Groups.

Yahoo Groups lets you set up a mailing list, optionally including
Yahoo Groups web features. You can define the group to be a
“discussion” group, where any member can post to your list, or a
“newsletter”, where only the owner – you in this case – can. Members
can choose to receive the messages on the web in their Yahoo account,
or by email to any email address they choose.

The “cost” is that the messages may have advertisements attached,
and your members will need to sign up with a Yahoo account. You may not
be able to directly import your list of members – you’ll need to send
them a one time message telling them to go join your group.

There are alternatives to Yahoo Groups, and there are also free
newsletter services, but I’ve no direct experience with them. If you do
intend to stay in the free services arena, Yahoo Groups would be the
direction I’d encourage, since it’s a known and popular service.

Do it yourself – mailing list software: I’m not
going to spend a lot of time on this, since it may require a little bit
of technical expertise to get going.

There are software packages available specifically to manage email
newsletters and discussion groups. The most common is a free open
source solution called mailman. This package is installed on a server, and gives
you direct access and control over as many mailing lists as you like.
It supports import/export, full user account management as well as the
ever important subscription confirmation that’s a big part of avoiding
being called a spammer.

Many inexpensive web hosting services will include mailman as part
of your web hosting package. This is a great way to get mailman
services pre-installed and ready to use.

Do it right – use a service: for the numbers you’re
discussing, I have to recommend that you use a email service provider.
ESPs are designed to solve exactly the problem you’re posing: getting
your email delivered to a large number of people on a regular
basis.

There are many providers, but I’m partial to AWeber – you can read
my recent review.

I’m not sure which ESP you found, but it doesn’t have to be nearly
as costly as you’ve described for the amount of mail you’re planning
on. There are many providers that will come in well under what you
found, including AWeber.

The advantage of going with a true ESP is management and
deliverability. You certainly won’t have to jump through all the hoops
you’ve described in piecemealing a Hotmail based solution, and a good
ESP will have a strong reputation and high deliverability. They may
force you to play by a few rules, but the result is that your email
list will be full of people who want to be there, who want your email,
and who are less likely to consider what you’re sending spam.

•

Rules?

Regardless of what solution you eventually take, there are some
important rules that you need to consider and follow when you start
mass mailing. Most of these are common sense, and are important ways to
avoid being called a spammer. Others are actually legal requirements,
at least in the U.S..

• Don’t add people to your list without their permission. This is the
  definition of spam. The best way to make sure that they
  actually do want to be on your list is to use a confirmed opt-in
  process. That’s the scenario that requires them to send some kind of
  confirmation email before they are actually added to your list.

• Send them what you promise to send, and nothing else. If people sign
  up, even using confirmed opt-in, for a newsletter, and then you start
  sending them other unrelated messages, that too is another definition
  of spam.

• Make it easy to leave your list. One-click unsubscribe might be
  required if your list is of a commercial nature. While it’s tempting to
  want to make it difficult to leave, so as to retain more subscribers,
  it increases the chances that they will start reporting your email as
  spam. And besides, do you really want to be pestering people who don’t
  want to hear from you?

• Be clear in each message who the message is from. If people don’t
  recognize the email, it is, once again, so much spam to them.

Sending bulk email, email newsletters, hosting discussion lists, and
anything that results in “messages to a lot of people at once” is
something that requires a lot of special consideration. I encourage you
to take the time to think it through and do it right.

Both you, and your recipients, will benefit.