How an Email Marketing Disaster Ended in Relationship-Building Brilliance

Got a massive kick out of this from reader Jason:

Subject: Auto-responder disaster and the kindness of friends

Hi Josh

I wanted to tell you about my brief, disastrous (and not so disastrous) foray into email auto-responders.

So I finally plucked up the courage to create my first list auto-responder welcome email series for new subscribers to my list. I create the emails. They look great. I fiddle with them a few times. Switch them on and off as I do. And … everyone in my list gets them. All my previous subscribers. Three times.

Now I’m sweating bullets. Terrified of a huge barrage of unsubscribes. Spam complaints. The end of the world. I send out an apology email. Beg for people’s patience.

And … I get a flood of emails back. More than I’ve ever received in response to an email campaign. People thanking me for the free book I included in the multiply sent welcome email. People saying that they love my work. That they support me. That it’s alright.

And now I’m scratching my head. Because I never get that sort of response usually. And it occurs to me that there’s something to be learned from all this. For one, I shouldn’t be so scared to send out emails more often. And second, I need to be more vulnerable in my emails. Because that apology email is what people responded to so well.


And while I thought about this, I thought about similar issues you’ve brought up before in your emails. So, thank you.

Keep well,

3 reasons I loved reading this email:

1. For starters, it’s just a fantastic story. And Jason does a great job of telling it.

Notice the lack of “throat-clearing.” He just jumps right into the story and tells what happened in plain, straightforward language.

I can *feel* his mortification at his mistake—I was cringing for him as I pictured myself making the same blunder.

And likewise I could feel his utter relief and astonishment at how his subscribers responded.

2. When I first started reading this, I wasn’t sure whether it was a personal email Jason wrote just for me…

Or whether this was a marketing email from some long-forgotten email list I’d signed up for.

That’s the effect you want to aim for in your emails.

Write like you’re writing for ONE person—because you are.

Eventually I deduced that Jason *was* writing just to me.

Still the fact that I couldn’t tell makes this pitch-perfect email worthy of your study.

3. A lot of entrepreneurs let the fear of making a mistake paralyze them—and they never send any emails at all.

Well guess what:

If you’re blasting out messages to thousands of people every week, you’re going to make some mistakes.

The good news is, when it comes to email marketing, mistakes are rarely fatal.

And in fact, if you’re just transparent with your list like Jason was, you can often turn an honest mistake into a net positive—a chance to deepen your relationship with your list.

Well done, Jason.

Now, it’s your turn.