How Frequently Should You Send Emails During Your ‘Onboarding’ Sequence?

The first few days with a new subscriber is such a critical time…

Those early emails are how they decide whether they LOVE you and want to read everything you send…

Or whether they mentally “mark as spam” every time your name pops up in their inbox.

Reader Lana is acutely aware of this. She asks:

If I typically send out a weekly email, how frequently would you send messages for the onboarding sequence. Afraid to overwhelm.

I have my own experiences with this—which I’m happy to rant at length about.

But instead I want to share a story I received a few days ago from loyal subscriber and JavaScript developer Meligy.

Meligy runs a meetup group of programmers in Sydney, Australia, and he’s been keeping me posted on his efforts to transform this free group into a profitable business.

He writes:

Hi Josh,

As you may remember, I have been considering monetising the crowd in my ng-sydney AngularJS usergroup, in a way that doesn’t change the group itself from being free and useful etc.

Recently I was asked to deliver a 1-on-1 workshop Angular over the couple of days of the weekend. I earned $1,800 before tax. It was amazing. I knew that this should be the way to make profit at much less cost than say a book or a course, especially that I get many newbies who want to learn the framework, and the usergroup is not the place to repeat the same beginner introduction over and over again.

I needed to sort some details like venue and proper cost, etc., so, I decided to focus on communication with the group in general, more than my mailing list, following a simple 80/20 concept.

Which leads us to the actual story…

I was sending a message to the group telling them about a special group event happening next week, and other special events happening in Sydney in the same week. I wanted to make sure I set a proper Reply-to address, and the horrible options in meetup.com got me to confuse a lot of things.

When I got something wrong, I decided to resend the same email. I didn’t even change the subject, hoping that many people would be less annoying this way given the short time window in between.

No matter how I checked the settings, I kept getting it wrong.

I ended up sending the group FOUR emails in half an hour time frame.

(I was hurrying to catch up with another thing I had to do that day, family and stuff. This is the first time I send this amount in over a year and half.)

I was worried that I’d get a lot of people unsubscribing from the group after that.

And indeed there were a few who left the group.

However, I found that all the ones who left, are members who have been in the group for a long time and either have not RSVP’d for any events, or only RSVP’d No for one or two.

They were the kind of people I wouldn’t rely on for coming to events, let alone speaking or engaging in other activities like workshops, etc.

They are people I’d rather not count in the total members number!

That’s actually net positive. I’m happy that they left, even though I won’t be trying to repeat this again in the future.

This obviously aligns with everything you said earlier in this regard.

People who care won’t be bothered.

People who are still “cold” (new members) also didn’t seem to be bothered!

You are amazing, and so full of wisdom!!

Definitely puts the lie to the myth that “sending more than 2 emails a month will cause my business to burst into flames,” doesn’t it?

My advice for Lana is:

Don’t worry too much about overwhelming your new subscribers.

In fact, your new subscribers will be MORE eager to hear from you than the ones that have been hanging around for a while.

You should kickstart the relationship by “frontloading” your communication so they hear from you more often while their interest is high (email courses are *excellent* for this).

Just make sure your emails are both educational and fun to read and your subscribers will be begging you for more.

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