Now that I've gotten started on a new thing, I was eager to start emailing my existing Gumroad customers, who purchased my Illustrator and InDesign Wireframing Kit, as well as my standard newsletter subscribers, in an attempt to spread the word.

In my zealousness, I did something that was not cool. I exported all of my Gumroad customer email addresses and imported them into my MailChimp list without their permission.

After doing so, I proceeded to send the email below to both my existing subscribers and my newly imported, not-really-subscribers.


So I’ve recently taken the plunge and bought some solid audio equipment for a new thing. That new thing is creating in-depth tutorials for Adobe Illustrator. My main focus to begin with, is to teach you how to get super fast and familiar with Illustrator and its tools, to use for your own projects, that will in turn make you money (possibly even a living), as my projects do for me.

I’m planning to create a very detailed series on using Illustrator for creating wireframes, specifically for a responsive e-commerce website. I’ll start with mobile designs, expand to desktop, and show you breakpoint variations in between, all while covering quick keys and tips and tricks.

I want to provide more value for you by creating an actual thing that you can use, as opposed to showing high-level tutorials with no real world applications.

Reply to this email and tell me your what you think about this approach. Will this help you?


-- Matt

After sending the above email I received quite a few unsubscribes. Rightly so. I also got a reply back from a very disgruntled recipient (make sure you see his reply below), confirming my initial hesitation and doubts about my tricky export/import maneuvers.

Fortunately, this was a single instance and every other reply was extremely positive and encouraging. However, that doesn't negate the fact that I overstepped my bounds.

So this morning, I segmented out the previously imported Gumroad customers within my MailChimp list and sent this email to only those people.

Hey there,

I'm sending you this email because you bought my "Wireframing with Illustrator and InDesign Kit" from Gumroad recently. Thanks for that! If you have any feedback at all, positive or negative, I'd love you hear from you.

Also, I want to extend to you an apology. You see, yesterday I decided to email my "mds subscribers" MailChimp list to let everyone know about a new thing I'm doing with Illustrator and some wireframing, plus future video tutorial products. Here is the email if you missed it.

Without much consideration for my existing Gumroad customers (i.e. YOU reading this right now), I exported all of your email addresses from Gumroad and into my MailChimp list. I assumed that if you bought my wireframing kit that surely you'd like to hear more about the same topic.

Perhaps this is true for you. I hope it is, but I also realize that some of you were probably thinking, "Why is this random guy emailing me and how did I even got on his list?"

Many people unsubscribed yesterday, which is totally understandable. One person went above and beyond to let me know exactly what he thought about my irresponsible email importing actions.

happy camper he is not

Here's the deal, to avoid further confusion, right now you are on my email list and I'll be sending emails to this list with design tips and tricks, specifically for Illustrator and possibly others in the future. I'm also working on creating a robust and in-depth product series that will be available for purchase later this year.

If you'd like to keep up with what's going on, do nothing (because you're already on the list) and just keep reading.

If you'd like to no longer receive these emails from me, please hit unsubscribe below.

Thanks so much,


I thought about removing the Gumroad customers completely from my list, but lots of them had already responded, saying that they're looking forward to the new content and excited to see what's next.

Removing existing customers from the list and emailing an apology and telling them to rejoin if they wanted, even though some of them were already onboard and excited, but telling them they had been subscribed and unsubscribed, and now they could resubscribe... well, that all just seemed too complicated, so I sent one last email (above) to apologize and try to clarify things.

Hopefully you can learn from my mistake if you decide to enter into the realm of consumer product creation and email marketing.

A Better Solution

A better solution to get my Gumroad customers willingly over to my MailChimp list would have been to message those customers directly about the product they purchased, through Gumroad. I could have used that as a channel to ask how the product worked out for them and answer any questions they had about using it.

Then, I could let them know I was doing something new with my email list on a similar topic and that they could subscribe if they'd like.

This method would have only converted a fraction of the existing customers to the newsletter, but that fraction would be a loyal fraction to build on.

Would you have handled things differently? What could I have done better? Let me know in the comments below.