Whiteboard Confessional: The Time I Almost Built My Own Email Marketing Service

About Corey Quinn

Over the course of my career, I’ve worn many different hats in the tech world: systems administrator, systems engineer, director of technical operations, and director of DevOps, to name a few. Today, I’m a cloud economist at The Duckbill Group, the author of the weekly Last Week in AWS newsletter, and the host of two podcasts: Screaming in the Cloud and, you guessed it, AWS Morning Brief, which you’re about to listen to.

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Transcript
Corey: Welcome to AWS Morning Brief: Whiteboard Confessional. I’m Cloud Economist Corey Quinn. This weekly show exposes the semi-polite lie that is whiteboard architecture diagrams. You see, a child can draw a whiteboard architecture, but the real world is a mess. We discuss the hilariously bad decisions that make it into shipping products, the unfortunate hacks the real-world forces us to build, and that the best to call your staging environment is “theory”. Because invariably whatever you’ve built works in the theory, but not in production. Let’s get to it.

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Welcome once again to the AWS Morning Brief: Whiteboard Confessional. Today I want to talk about, once again, an aspect of writing my Last Week in AWS newsletter. This goes back to before I was sending it out twice a week, instead of just once, and my needs weren't that complex. I would gather a bunch of links throughout the week: I would make fun of them and I had already built this absolutely ridiculous system that would render all of my sarcasm from its ridiculous database where it lived down into something that would work to generate out HTML. And I've talked about that system previously, I'm sure I will again. That's not really the point of the story. 

Instead, what I want to talk about is what happened after I had that nicely generated HTML. Now, I've gone through several iterations of how I sent out my newsletter. The first version was through a service known as Drip, that's D-R-I-P. And they were great because they were aimed at effectively non-technical folks, by and large, where it’s, “Oh, you want to use a newsletter. Go ahead.” 

I looked at a few different vendors. MailChimp is the one that a lot of folks go with for things like this. At the time I was doing that selection, they were having a serious spam problem. People were able to somehow bypass their MFA. Basically, their reputation was in the toilet and given my weird position on email spam, namely, I don't like it, I figured this is probably not the best time to build something on top of that platform, so that was out. 

Drip was interesting, in that they offered a lot of useful things, and they provided something far more than I needed at the time. They would give me ways to say, “Okay, when someone clicks on this link, I can put them in different groups, etcetera, etcetera.” You know, the typical email, crappy tracking thing that squicks people out. Similarly to the idea of, “Hey, I noticed you left something in your cart. Do you want to go back and buy it?” Those emails that everyone finds vaguely disquieting? Yeah, that sort of thing. So, 90 percent of what they were doing, I didn't need, but it worked well enough, and I got out the door and use them for a while. 

Then they got acquired, and it seemed like they got progressively worse month after month, as far as not responding to user needs, doing a hellacious redesign that was retina searingly bad, being incredibly condescending toward customer complaints, subtweeting my co-founder on a podcast, and other delightful things. So, the time came to leave Drip. So, what do I do next? Well, my answer was to go to SendGrid. And SendGrid was pretty good at these things. They are terrific at email deliverability—in other words, getting email, from when I hit send on my system into your inbox, bypassing the spam folder, because presumably, you've opted in to receive this and confirmed that you have opted in—so that wasn't going to be a problem. 

And they still are top-of-class for that problem, but I needed something more than that. I didn't want to maintain my own database of who was on the newsletter or not. I didn't want to have to handle all the moving parts of this. So, fortunately, they wound up coming out with a tool called Marketing Campaigns, which is more or less designed for kind of newsletter-ish style things if you squint at it long enough. And I went down that path and it was, to be very honest with you, abysmal. 

It was pretty clear that SendGrid was envisioning two different user personas. You had the full-on developer who was going to be talking to them via API for the sending of transactional email, and that's great. Then you had marketing campaign folks who were going to be sending out these newsletter equivalents or mass broadcast campaigns, and there was no API to speak of for these things. It was very poorly done. I'm smack dab between this, where I want to be able to invoke these things via API, but I want to also be able to edit it in a web interface, and I don't want to have to handle all the moving parts myself. So, I sat down and had a long conversation with Mike, my business partner. And well, before I get into what we did, let's stop here. 

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So, we looked at ConvertKit, which does a lot of things right, but there are a few things wrong. There's still no broadcast API, you have to click things to make it go. So, I have an email background, Mike has an engineering background. And we sat there and we've decided we're going to build something ourselves to solve this problem. And we started drawing on a whiteboard in my office. This thing is four feet by six feet, it is bolted to the wall by a professional because I have the good sense to not tear my own wall down, instead hiring someone else to do it for me. 

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