How to Write a Super-Sized Autoresponder Series

This is a guest post from Chris Guillebeau. If you enjoy this post, you may also like this interview about how he builds relationships via email marketing.

Here’s Chris! -Justin Premick

In April 2010, I launched the Empire Building Kit, a training course designed to help aspiring entrepreneurs build a business in one year by doing one thing every day. The course featured a ton of content, ranging from video interviews to PDF case studies of unconventional entrepreneurs who provided complete financial details on their business.

But the most popular feature of the course came about by accident.

When developing products, I always start with the end-goal in mind and work backwards. In this case, I liked the messaging concept of “build a business in one year by doing one thing every day” – but I wasn’t entirely sure how to implement that in the course.

I had been traveling overseas in the weeks prior to the launch, and I had a hard-and-fast deadline: the Empire Building Kit would launch on my birthday, while riding the Amtrak Empire Builder train from Chicago to Portland, Oregon. There was absolutely no room to push back the launch date, and tens of thousands of people were following the pre-launch story through my blog.

I originally imagined the “one step every day” would be a massive checklist, but when I started writing the list, I only got to step #42.


Forty-two isn’t the same thing as 365, so I had a problem.

That’s when I decided to write 365 emails with a lesson or tip in each one, every day for an entire year.

I’ve been familiar with Aweber’s great autoresponders feature for years, and have often used it to build sequences of up to 20 messages in length. Since the Empire Building Kit was naturally a “big” product, I decided we might as well go all out and publish a year’s worth of lessons, one per day without a break. Among other things, this strategy would give me time to figure out what came after step #42.

Great Idea, Right?

Well… business-wise, it’s worked out very well. The EBK quickly became my bestselling product, and a year later, it continues to sell every day with limited promotion.

Somewhat to my surprise, the follow up series is often identified by customers as the most popular feature of the whole product. Every day, dozens of people on the list reply to their daily message by sharing their own story, asking questions, or otherwise offering feedback.

The Challenge…

Writing 365 lessons was a much bigger project than I expected.

I envisioned working with a co-writer to draft many of the daily lessons, which seemed like a good idea in theory. Long story short, that didn’t work – I realized that it would be difficult to combine multiple writing styles at midpoint through the course, so I ended up doing them all myself.

Over the next nine months, I wrote well over 120,000 words for the series, or more than two thick books. Since I write other books, magazine articles, and regular blog posts as part of my ongoing work, this was a lot of writing.

I went on a 63-city book tour last fall, and every night after the gig I’d go back to my room and write Empire Building Kit mailings. The combination of activities was worth it in the end, but also tiring.

Getting It Done

How do you write an extremely long string of mostly-articulate and somewhat-helpful messages?

I learned a few tricks as I went along:

The Weekly Review

Every seventh message looks back on the lessons of the previous week. This serves as a good recap, helps to reinforce the overall arc and scope of the course, and also counts as an extra message if you’re trying to get to 365. Bonus!

Mix It Up

In a long series, you’ll almost certainly want to vary the style to keep the reader’s interest over time.

In my case, some messages were quite long (over 2,000 words), while others were very short. Some messages linked to a two-minute video. Some were part of an ongoing topic that required numerous messages, and others were one-offs.

Highlight Your Customers

Early on in the series, I shared a number of “Disaster and Recovery” stories of things I had done wrong, and how I had (eventually) created a success from the initial disaster.

These mailings were especially popular, so I asked for submissions of other stories from people on the list. This helped us create another fifteen messages over the course of the year, and brought a lot of attention to the people on the list as well.

One Tip or Strategy per Message

I learned to keep it light, basic, and easy: “In today’s mailing, you’ll learn about [topic x].

We won’t be discussing [topic y] or anything else.” There was always another day for another mailing, so I didn’t want to cram too much in.

Keep Plowing Along

When you write a long email series, not every message will be a masterpiece.

In my case, I tried to keep them as fun and actionable as possible. I showed my readers how to avoid PayPal fees, increase income through selling on different platforms, create a physical product from a digital one and so on.

Every day, another lesson – and another march toward the final mailing on day #365.

Looking Back

At first I was worried: would I really be able to keep this up? Thankfully, I found a rhythm, writing 2-3 messages on most days, and sometimes completing a whole week-long series while on a long flight to Asia. (Opinions may vary, but I tend to think that the messages got better as they rolled along – as with almost all creative work.)

When I finally finished writing the entire series (three months ahead of schedule!), I felt a huge sense of relief as I walked outside the coffee shop where I had queued up the final mailings. Looking back at the countless hours I had invested in the project, I had no regrets, but I was also fairly certain that I’d find a different way to do it next time.

Feel free to beat me by developing the world’s first 1,000-lesson follow up sequence. I’m out of the running!


Chris Guillebeau travels the world and writes for a small army of remarkable people at His new business,, mercifully involves only a five-message follow up sequence.