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Paul Jarvis

The three most powerful MailChimp automations

MailChimp automations don’t have to be scary.

It can actually become the most important part of your business, since it helps you connect with new leads, turn them into customers, then into fans—no nerdiness, coding or tech skills required. It can even happen while you’re sleeping (or eating vegan burritos). No matter what type of business you run, from an online course website to a vegan burrito delivery service, email automations are a powerful way to connect with folks interested in what you’re doing.

(Note: Even if you don’t use MailChimp, you can set the following automations up in any newsletter service.)

In fact, you probably already use it without realizing, since you’ve got a welcome message when someone signs up for your list (MailChimp automatically sends one, unless you turn it off or use a customized welcome automation instead).

Unlike campaigns in MailChimp, which are one-offs, automations happen every time specific people meet specific criteria, like buying a product or signing up for a demo. And once an automation is running, you can segment people out. For example, if you’re pitching your product and someone buys on the 2nd email, you don’t want them to get the 3rd pitch. By tracking who buys what from you, you can take your automations to a whole ‘nother level. You can learn how to do this in Chimp Essentials.

This is the whole point of mail automation–sending the right emails to the right people at the right time. It’s as simple as that. So let’s look at three of the most helpful automations, beyond the welcome email.

Turning leads into customers with MailChimp automations

You know how sometimes you go to Costco and there’s stations set up with delicious free samples (sometimes even vegan burrito samples, although the frozen ones aren’t ever as good as the ones made fresh)? That’s because people want to try (or taste!) before they buy.

The same is true with digital products, like ebooks, online courses and  software. Which is why automation sequences that help give people a taste of what you’re offering can be so helpful—and by helpful, I mean profitable.

My highest converting MailChimp automations sequences are the ones that do a few things really well:

  1. They educate. If I’m selling an online course on the business of freelancing, I’m going to offer an automation sequence that teaches people some valuable lessons about the business of freelancing first. I’m going to let folks sign up for this free series on the homepage of course, and I’m going to drip out daily lessons to them to really give them as much education as possible. The best lessons won’t be held back or hidden behind a paywall either. I’m going to lead with solid gold. Showing these subscribers how useful the course can be helps build trust.

  2. They self-select. For myself and many other people who sell things online, I’d rather make sure someone is a great fit for my product first, before money is involved, then take their money only to give them a refund later. Automations  triggered before any purchase is made allows people to get a taste of my teaching style, my language and exactly what they’re going to get with my offering. That way, if they come to realize what I’m offering isn’t for them, they can unsubscribe and not have to ask for a refund.

  3. They share and build relationships. The best way I’ve found to sell is to tell other people’s stories. All the automation sequences dispatched (get it?!) before I ask for a sale involve sharing how other customers have used what I sell to do better or profit more. I share case studies, success stories, videos of people who’ve been customers for ages and short testimonials. Such tangible data helps build even more trust, because it’s not just you saying how awesome your product is. It’s other people saying it

  4. Then, they ask for the sale. Once I’ve educated subscribers, shown them exactly what they’ll get and shared other people’s stories about what I’m selling, I can ask them if they want to buy. Here’s where things get fun: I only want to ask if they didn’t buy yet. Sometimes folks sign up for a free sample which has 10 days of automations but they buy on day 2. Or day 9. I don’t want to pitch to people who’ve bought already because it makes me look silly. Imagine you buy a freelancing course, then a few days later get an email telling you how amazing the course is and that you should buy it today! Preposterous. MailChimp lets you be smarter than that. Coupled with what you learn in Chimp Essentials, you can automatically segment out people who’ve already purchased your product from your automations. That way they can still get the educational emails (if they want), but won’t see pitches for any products they already own.

Within each email in a MailChimp automation sequence, you have the ability to create segment conditions. If you’re using Fixtail (or something like Shopify or WooCommerce) to send purchase information about subscribers to MailChimp, then you can segment people out if they’ve purchased a specific product. This is how the right email is sent (or not!) to the right person at the right time.

Turning customers into fans with MailChimp automations

Too often businesses don’t pay enough attention to their most important people—their customers. They work so hard at making the sale but then put almost no time into what happens after the sale.

Which is too bad, since that’s the best time to connect with your new customers, right after they buy. Once you add purchase and order information to subscriber details, so you can set up automation sequences that trigger the second they become customers.

Here are a few things post-sale automations can do to really benefit your business:

  1. They say thanks. Call me a polite Canadian, but I like to say thank you when someone does something for me, whether it’s holding the elevator or buying something I sell. I like to let folks know that, even though it’s an automation that’s being sent, I noticed their purchase and was appreciative of it. You can even get fancy, by creating personal video thank you messages in a pretty neat app called Bonjoro. The first email in a post-purchase automation can simply thank a person for buying and maybe ask if they have any initial feedback. Never be a jerk.

  2. They give a reminder about access details and important URLs. Typically, if you’re selling something digital, after a purchase people are taken right to the thing they just bought: a course, an ebook, a piece of software. But, after they use it a bit, they get distracted (probably by cat videos), they might forget how to log in, where their downloads are, or other important information. The second automated email I send in a post-purchase sequence is a reminder email that gives all the details they need to keep handy.

  3. They show customers how to get the most out of what they bought. Just because someone bought from you doesn’t mean the education should end. Indeed, if you want your customers to become fans of what you do, the education can’t stop. Sometimes people don’t know how to properly use what they’ve purchased—like software—or don’t know how to get the most out of it—like a course. By teaching them all the ins and outs of what they bought, they’ll be more likely to use it. And if they’re using it, they’ll like it more and tell others. For bigger items, I tend to drip education out in 4-8 emails, with each email covering one important topic.

  4. They help ensure customers are using what they bought. A post-purchase sequence can help your customers actually use what they bought from you. Are they watching the lessons in your course? Have they started using your software? Reading your ebook? If they aren’t, you can ask why or offer to help. If they are, and they’re digging it, you can give them a way to review their purchase (on Amazon, on the App Store, wherever).

  5. They take their pulse. After I’ve thanked, reminded, educated and made sure someone is using what they bought, I like to ask them how likely they’d be to recommend the purchase to others. This is done with a simple survey or poll in MailChimp. Basically, “would you recommend this to others?” If they respond yes then I trigger a follow-up email that gives them a way to share it and join an affiliate program, if there is one. If they say they wouldn’t recommend it, I reach out to find out why. Either way, the feedback is invaluable.

By engaging with customers after the sale, you can take them from simply buyers of what you’re selling to fans of you and your company. Fans are much better than customers too. Fans are a part of your sales team. They’ll tell everyone they know about what you’re doing and selling. So treat them well.

Turning fans into repeat offenders with MailChimp automations

Whoa, kudos for making it to the final step! You’ve turned subscribers into customers, and customers into fans. Now you’re ready for the final step: turning those fans into repeat offenders. And I’m not talking about stealing vegan burritos for a living (burrito bandits, if you will). I’m talking about doing what it takes to make folks want to buy from you… again.

If you know exactly what someone bought and when, you can do some powerful stuff with MailChimp automations. You can turn a $20 one-time purchaser into a long-term fan who spends thousands of dollars on your products/services over the course of years (or even decades). Let’s look at some of the most useful MailChimp automations to get your fans to come back for more:

  1. They offer replenishment. This doesn’t just apply if you’re selling subscription-based foods, like Soylent. Replenishment emails also work if you sell software that uses credits or you sell subscription based digital products that are close to the renewal date. I’ve seen them work really well for charity organizations that offer virtual animal adoptions (I may virtually adopt a lot of animals…) to let folks know what another yearly donation can mean for their adopted friend. By reminding folks what they’ll lose out on if they don’t renew or replenish, you give your business the best chance to keep them as customers for longer. You can even offer deals or discounts for returning customers to make them even more eager to buy more.

  2. They pitch additional products. What I’ve noticed with my own customers is that getting them to buy the first time is the hardest part. It takes the longest, it requires more work on my end (which is totally fine, I like working) and it’s the most trepidatious a person will be, since they don’t know your business that well yet. On the other hand, once someone becomes a customer of mine, they’re more likely to buy more of my stuff. And not just a bit more likely either, a whole lot more likely. Most of my customers have bought more than one thing from me. That’s why having an automation sequence that triggers if someone buys one thing, but hasn’t bought another is super useful.

  3. They reward your biggest fans. Since I sell several things: courses, software, and the occasional random product, I like to know which subscribers are the biggest financial supporters of what I create. That’s why I like to reward the people who’ve spent the most money with my business and do something special for them. I like to ask for their mailing address if they spend more than a certain threshold, so I can send them something fun in the mail. This gesture helps create a better connection with the people who are the most supportive. And hopefully, it helps keep them stoked to buy from me in the future.

To sum it up

Hopefully now you can see that MailChimp automation isn’t so scary. In fact, it’s super useful to any business that sells online.

  1. Make sure your leads get to know you before you try and sell them stuff. Educate them, show them why what you’re selling is valuable, show them there’s more than just you talking about your products.

  2. Make sure your customers know how to, then use what they’ve just bought. Teach them the ins and outs or little tricks. Show them what they bought is valuable and how they apply that value to their own lives or businesses.

  3. Make sure you keep them coming back for more. Give them a reason to. And then treat them like super stars when they do.

This is why I teach Chimp Essentials—so you can learn how to setup MailChimp automations like the ones I listed above. Because when you know how to do things like that that, you can get pretty smart with how you set up and segment your MailChimp automations.

The best part is you can set these MailChimp automations up and almost-forget about them. You do need to check in on them from time to time to make sure they’re converting well, helping a lot and being read. But that said, they’ll still work for your business whether or not you’re sleeping or eating those delicious vegan burritos!

How to make money from your mailing list

I have to start with this disclaimer about how to make money writing newsletters …

I hesitate to write articles that include phrases like “how to make money” because a) money’s a crappy goal in and of itself and b) I don’t want my writing to get lumped in with thought-leader marketing bullshit.

Seriously, Google “how to make money from [insert any activity]…” and total crap fills the results.

Hopefully this will be a shining beacon of honesty for Google. Or at least, for you.

Disclaimers aside, most folks who make a living online including me, do so by revenue generated from mailing lists.

“The money is in the list” and all that.

In fact, year over year, more and more of my income is a direct result of my newsletter (90%+ now). I typically see, for $1 I spend on MailChimp’s services (the email service provider I use and that’s an affiliate link), $120 in revenue.

That kind of ROI doesn’t happen from ads (at least not for me, I’ve tried) or from posting on social media (luckily that’s free to use, mostly, because I make very little revenue from it).

Email marketing consistently outperforms every other channel, by a metric ton.

But, and there’s always a but…

How do you make money from your mailing list?!

Let’s dive into the specifics and examples of how paying for an email service provider translates into this magical money being deposited into your account.

Money is made writing newsletters indirectly

It’s not enough to have a big list, you have to people on it that click your links, and then buy what you’re selling.

For example, if you have a list of 100,000 seasoned, professional Rails developers and you tell them you’re selling a basic training for how to learn Rails, you’ll generate zero revenue. (They already know Rails.)

Or you try to sell eco-friendly dog beauty products to a list of people interested in surfing in South Africa. (Ok, there might be a little cross-over between dogs and water sports).

The beauty of mailing lists is that you have direct access to the people on it. As in, you can email them. You can get to know them. You can find out who they are, what they want to know and what sorts of things they’d be interested in buying.

  1. Having a list is great.
  2. Having a list that’s full of people with the same interests, desires and needs is better.
  3. Having a list that’s full of people with the same interests, desires and needs that you speak to on a regular basis is the top rung of the email marketing money ladder.

Breaking that last bullet down a bit:

In order for people to click and then buy from the emails you send them, they need to trust you completely. This trust is built by communicating with them regularly. And it’s built because you’re giving them content even when you have nothing to sell.

I email my own list once a week, every Sunday morning. I never miss a Sunday and except for 2-3 times a year, I have nothing for sale in those emails – I’m just sharing an article I wrote.

So list subscribers don’t convert to buyers when/if you only blast them sales pitches. You’ve got to give them value, through regular content, and them pitch them.

You don’t need a big list to make great money writing newsletters


I only had a list of a few hundred people during my first year, when I was just doing web design. I generated 6-figures from it because I only needed 12 clients a year.

My list was focused on answering questions that the type of people who hired web designers wanted to know. And after each article I wrote, specifically for those types of people, I mentioned my current schedule.

For example: “I’m currently booked 3 months out and have room for 1 more client as of then. If you’d like to be that client, get in touch now, as I can only lock in projects when I have a downpayment and a signed contract.”

That was all I needed to create enough revenue to live off of. A few hundred people and 12 sales a year.

I only worked at growing my list to tens of thousands when I started selling products which cost a lot less than my services.

My favourite newsletter only goes out to a few dozen locals, because it’s from the farm down the road that has a tiny market on Saturdays. That one email, once a week, to 20 or 30 people, generates enough revenue for them to work their farm (and has led to connections to sell their produce elsewhere too).

Figure out how you’ll make money from your newsletter

If there was a one-sized-fits-all solution to making money from a mailing list, then you wouldn’t need this article because you’d already know the answer.

There’s no easy answers when it comes to making money – otherwise we’d all be rich and having money fights on our private yachts.

There are however several general ways to generate income:

  1. Selling your own products. Making products is fun (I’ve done it for years). If people are on your list, you hopefully know enough about them and have been helpful to them that they’re asking you for something. Make that. Sell it to them. Since I primarily create courses, I spend most weeks writing free articles that relate to a course subject, and then once or twice a year, I give a pitch to buy it.
  2. Selling other people’s products. Affiliates take more work on the sales side, probably because you don’t create them yourself – you just link to them. Hence, it’s even more important that you provide a clear reason to your subscribers as to why you’re pitching them on these products. It’s also important (i.e. required by law) to disclose an affiliate link as an affiliate link. Like this: I use FlyWheel (affiliate link) as my web hosting company because they are reliable, secure and have friendly, human support.
  3. Selling sponsorships. Just like a podcast, your list, if it’s big enough and/or targeted enough, can have a sponsor. They get a link and possibly a small write up in your newsletter, seen by lots of people, and you get paid. My own podcast sponsor FreshBooks is also my mailing list sponsor (since they’re basically the same content in different formats).
  4. Selling patronage. If you want sponsors for your list but don’t want to go the sponsorship route, you can ask your audience to be micro-sponsors and kick in a bit of money. BrainPickings does this well (asking for $3-25/month for amazing content).

Those are the four main ways you can make money from your list, and they each have their own pros and cons.

There are also wrong ways to make money from your newsletter

Very, very wrong ways.

Like Darth Vader cutting off his own fucking son’s hand wrong.(Sorry if that’s a spoiler!).

That’s the dark side of the email marketing force. There’s also a side that’s not plain evil but just ineffective.

It’s hard or harder to make money from your mailing list if:

To summarize how to make money writing newsletters

It’s possible to make a decent amount of money from your mailing list – if you put in the work and do it properly and with some personalization. There’s no gravy-train that takes you to BagsofMoneyVille station. (Also, can you tell me where BagsofMoneyVille is on Google Maps please?)

But if you build a list of people that have similar interests and needs, become a trustworthy and regular source of value for them, they’ll reward you with purchases.

No rocket science, no magic fairy dust, you just need to keep things above board and make your mailing list a priority in your business. I’ve done just that and that’s why I see a 120x return on my newsletter investment.

Which is better, ConvertKit or MailChimp?

There are a lot of articles out there about ConvertKit vs MailChimp and why ConvertKit is better. And while healthy competition is awesome, those articles are completely wrong in their portrayal of MailChimp.

In the effort of fairness, let me present to you an accurate description of what MailChimp can do, in comparison to ConvertKit.

I use MailChimp  to run my entire company. More than 90% of my revenue is generated directly from my newsletter – three courses, four books, two software products, two digital products, a weekly article newsletter and two podcasts. All fully automated, segmented and running on MailChimp.

I end up making 120x what I spend on MailChimp’s service selling those products, so although the cost of their software is my biggest monthly expense, it’s obviously very worth it for me.


Paying double for the same subscriber

This is the biggest gripe I hear about MailChimp — if the same person is on several of your mailing lists, you pay for them twice. So if you have 1,000 people on 5 of your lists, you’re paying 5x more each month.

While this is absolutely true, it doesn’t have to be. If you employ proper list management, you can run one list where subscribers are never duplicated. You just have to know how to properly segment and group them together (similar to how ConvertKit tags subscribers).

For my own list, I group people by what they’ve purchased, what they’ve not purchased, which automations they’ve already received, what pages they’ve visited (or not visited), where they signed up from, if they signed up for a webinar or content upgrade or anything else, and more.

One list – tons of data about each subscriber. That’s pretty much how ConvertKit sets up lists too. I can even “update” subscribers if they’re already on my list but sign up for a content upgrade or a webinar or something new. All done via MailChimp and a single plugin for my WordPress site.

I never pay for the same subscriber to be on multiple lists unless I want to -there are a few occasions when that’s the case, like when I want  a separate list for a monthly paid product. I want that to be a separate list because if someone doesn’t want my weekly emails and unsubscribes, they aren’t dropped from the monthly paid list too.

What’s more, MailChimp lets you create links where subscribers can change the type of emails they get (based on leaving automations, using simple polls baked into MailChimp and other tools). ConvertKit doesn’t let subscribers update their profiles, they’re either IN or OUT.


You can’t tag in MailChimp

This is another complaint I often see. Yet tagging in MailChimp is just called something else: groups and merge fields. I use both heavily to make sure I know as much about each subscriber on my list as I can.

If someone buys something from me, they’re placed in a group on MailChimp. If someone signups for a webinar or workshop, they’re placed in a group. When someone signs up for my list, the page they signed up is the value in a hidden merge field on my list.

So you can tag in MailChimp, it’s just called something different.

MailChimp can actually store more user data than ConvertKit when it comes to eCommerce as well. ConvertKit is great for bloggers, but MailChimp is great for people that make money from their list. MailChimp’s eCommerce360 lets me store a metric shit-ton of data on transactions – like what product someone bought, for how much, what coupon they used, the transaction ID, the total number of purchases and the total revenue too.

The main feature-killer that MailChimp has which ConvertKit does not is the ability to track the return on investment of each campaign. Meaning, after I send out a pitch email to my list, I know exactly how well it converted and how much revenue it brought in. I can see how many sales, the total revenue and the conversion rate for each email.

For my software companies I also use MailChimp’s transactional service called Mandrill. I also plugin Mandrill into every WordPress site I have that sends emails to users – like online courses. The reason I do this is because I can verify and authenticate the email domain in Mandrill so emails sent from WordPress are more likely to reach inboxes. There’s no comparable service with ConvertKit for this need.



The second biggest gripe I hear from people about MailChimp is that their automations are subpar. Which is interesting because when everyone someone tells me this directly, I probe a little further and find out they never actually tried automations with MailChimp, or they tried them 5 years ago (when, granted, automations weren’t awesome).

I do some pretty neat things with automations in MailChimp that let me run a very complicated business with several products without the need for staff or virtual assistants. It’s just me.

Here are some of automations I do with MailChimp:

  1. If someone’s interested in a product, they can sign up for a sample, which is delivered and then they receive a series of teaching and pitches. My automation sequences automagically remove people who buy during an automation, so they’re aren’t ever pitched something they already own.
  2. If someone’s in an automation sequence and want out but want to stay on the list, I always include a link for that, which happens automatically.
  3. If someone buys something from me, they receive a series of educational emails aimed to teach them how to get most out of the product. A few weeks in, they’re asked if they like the product they bought (it’s a simple YES or NO set of links). If they answer yes, and I have an affiliate program, the next email they get is telling them about the affiliate program. That email is only sent if they like the product.
  4. If someone’s on my list and I pitch them a product, MailChimp (through Goals) can tell if they’ve visited the checkout page but not purchased. If that’s the case, and they almost checked out but didn’t finish, I send them an automated cart abandon email. ConvertKit can’t do this – there’s no way to track a subscriber that goes to your website with their software.
  5. If someone signs up for a webinar or a content upgrade, even if they’re on my list already, they receive that, and then continue to get my weekly emails.
  6. If someone’s currently in an automation sequence (like free lessons for a course), they don’t get my weekly email until they’re finished with that sequence, so I don’t overload them with emails.

There are lots of bloggers who say that MailChimp doesn’t allow content upgrades or updates to subscribers who are already on your list, but that’s simply not the case. A simple plugin (any will work, I personally like MC4WP) will allow you to do this. Yes, it doesn’t work out of the box, but with a simple 1-minute install of a plugin, it does.

That’s just a handful of targeted automations I use in MailChimp to run my business (even when I’m sleeping or out for vegan tacos). It’s as powerful as any other system I’ve tried, and is more than enough for 90% of people who use targeted email marketing.


Affiliate programs

The first thing I have to mention is that ConvertKit has an amazing affiliate program — they pay out 30% commissions, for everyone you refer, forever. This is absolutely amazing, and it’s why people like Pat Flynn (and many others) are earning more than $20,000/mo in affiliate commissions from ConvertKit.

ConvertKit’s own signup page for the affiliate program lists “write an article comparing ConvertKit to X” with an affiliate link as the main way to convert others. It’s 100% smart, and I give them credit for building a strong network of affiliates.

MailChimp’s affiliate program is awful. You get $30, once, for every person you refer to their service (and they get $30 too). There’s no way to ever earn $20,000/mo from that. If you’re looking for newsletter software that will pay you the most for referring others, and that’s your main goal, then ConvertKit is absolutely better than MailChimp.

One other note, while we’re talking about affiliates – a lot of folks will tell you that MailChimp doesn’t allow you to even use affiliate links in your newsletters. This is simply not true (I use affiliate links all the time, I have for years). They just won’t let you use blacklisted scam affiliate URLs, which is a good for both you and your customers.


I can A/B test a lot of things in MailChimp. From subject lines to “from” names to send times to content – MailChimp lets me enter in 2-3 variants with each test.

A/B testing lets you figure out the best option for getting your list to open and click links. That’s how you make money with your list. ConvertKit doesn’t (currently) have this feature available.

ConvertKit does excel with form stats. You can see the conversion rate of each form right in ConvertKit. MailChimp doesn’t have that feature, so I use Google Analytics to track this (but it does mean switching screens to see these stats).



MailChimp lets you easily create pretty templates with their drag and drop feature. I’ve been a designer and programmer for 20 years, and I still use their drag and drop templates because they’re faster and easier than coding something myself, and I know they look stellar across all email clients.

That said, plaintext emails (which ConvertKit really pushes) tend to convert better in terms of clicks and reads to the bottom of each email. But how I do I know this? Because I can split test full design vs. plain-text in MailChimp for my list (otherwise I wouldn’t know this for a fact) – something you can’t do in ConvertKit.



While cheaper isn’t always better, there is a free plan with MailChimp where you can test out and grow your list to 2,000 subscribers, with limited features. ConvertKit doesn’t offer a free plan and their pricing is more expensive.

To have a similar plan on ConvertKit would cost me $100/mo more. That said, they do offer free migration services to move your list to them, and MailChimp doesn’t. I chalk that up as a smart move for a newcomer software service (MailChimp has been around since 2001).



I will mention that both companies are run by champs. I’m friends with a lot of folks at both companies, and I hear from lots of people that customer support from both places is top-notch.

I don’t think there’s bad a choice here – pick the newsletter company that best fits how you work and how closely their setup matches your own business. For the majority of people, it comes down to which features mentioned above are the most important to you.

Every article I’ve found so far comparing the two services is just plain wrong and has wrong information in it. So pay attention to what other people are telling you, and why they’re suggesting what they’re suggesting.

My favourite newsletter is one you’ve never heard of

The best mailing list I know of isn’t even a mailing list at all. That’s because it’s a BCC list. It’s from my local farm and gets sent to 20 people who live in the area. It doesn’t even use mailing list software like MailChimp (gasp) or have automations.

There’s no on-exit modal, conversion-oriented landing page, or 154-page PDF bonus on their WIX website.

In fact, you can’t even sign up for it online. You have to be at the farm, pay for your veggies and then fill in the piece of paper attached to a clipboard. And then, within a week (or three), you’ll maybe start to get the emails (if they remember to BCC you).

All that said, I love this mailing list so freaking much.

It’s an example of perfection in email marketing. The woman who writes it isn’t a best-selling author, isn’t a marketer, and probably spends very little time online because she’s busy being a full-time farmer. But still, even though writing newsletters isn’t her “job” she makes sure it happens consistently every week—even though the list consists of only 20 people. And here’s why I love it:

  1. It’s 100% useful. I get this mailing list the day before the farm has its Saturday market. So I know exactly what they’ll be selling and I can decide if I want to go, or how early I’ll line up (if they mention some veggies are in short supply… and there’s always a line-up). I get the email when I need it, eager to know what’s in store for the market the next day.

  2. It’s 100% consistent. I get it every Friday night during the selling season. No excuses, no exceptions. One time the lady who writes it was away so the other farmer wrote it—and it was just as good.

  3. It’s 100% hilarious. I laugh out loud every time I read it. You’d think selling organic, heirloom veggies and homemade pastries could be somewhat boring or monotonous, but they tell a great story every single time. Everything from saving cows to mobster zucchinis. It’s the only mailing list I stop whatever I’m doing to read start-to-finish. It just goes to show you can put your personality into and create interest in anything.

  4. It’s 100% to the point. There’s no fancy mailing list software, no images, just plain-text with a story followed by a list of the produce that’s available. All bells and whistles have been stripped out (or never added in the first place). I get exactly what I need when I need it.

Let’s look at some excerpts from it, so you can see what I mean:

“Fall is all about crops you can depend on for the long haul: the sturdy rutabaga, the cantankerous carrot, the starchy, stable potato. They are like bulky sweaters for your bellies, comfortable and filling, these vegetables will be sure to hold you over all winter long.

“Josie wants to apologize. It was a dirty trick she played on some of you last Saturday. Honestly Josie, who doesn’t put sugar in a rhubarb galette? And the added lemon juice, how cruel. I’m sure she just forgot folks…sure. It must have been the early morning last Saturday. She’s out of practice and maybe a little vindictive after I left her on her own. She’s trying to make me look bad. But never fear, those who have been wronged will have justice. With your best pucker face, let her know how you feel and she’ll get you a new and shiny galette on the house.

“A calf fell down a well this last weekend. For hours, it must have struggled in the murky water until finally discovered at nightfall. With its head submerged, it had finally stopped struggling and began to sink. Mr. Benson dove in the well after it, pushing its nose up, breaking the water’s surface. With his trusty excavator close by and his friends to the rescue, tediously, they brought the calf on to solid ground. Exhausted, but alive, the calf and its cowboys live to fight another day.

“These zucchini are getting too big for their stripes and outgrowing their egos. These vegetable mobsters have been taking liberties in the garden, pushing around (and over) our fragile fresh bean crop. Yes, the only common ground these two share…is…well…just that, common ground. This prickled menace will stop at nothing to get under your skin. In retaliation, we’ve taken some of the biggest most vile offenders and made a fresh batch of our famous relish. But, these guys won’t take this lying down (well, they just might). But be warned. Lock up your cars tomorrow, or you just might find a few zucchini thugs lurking in your backseat!

So you see, cultivating an eager mailing list and a captive audience isn’t all about software, funnels, fancy tips and tricks. It’s about sending interesting and useful content to the people that need it, with consistency. You don’t have to wait until your audience is massive, or until you have something to sell. You just have to engage with people in a way that benefits both you and them, with a little bit of your personal flare.

Now excuse me while I wait for another Friday and another email from my favourite farmer.

This is the exact opposite of every “grow your list” article

There are SO MANY articles about how to grow your email list, and really, they just spew the same tired crap about “more subscribers = more profit” and using “All The Popups”.

These subscribers at all costs articles are horribly short-sighted, and worse, require a tremendous amount of growth because there’s inevitably so much churn (in the form of unsubscribes).

What happened to the good old days of building your list? Before growth-hackers and content marketers got their grubby little hands on newsletters?

I’ve tried basically everything with email marketing—both as a consultant working with other people’s lists and as a person who needed to grow his own list audience and build product revenue.

Modals, free email courses, on-exit intents, sticky-bars, slide-ups, content-upgrades, home gates, landing pages, takeovers, freebies, I’ve done it all. (Even a few things I shouldn’t have, in the name of science and experiments, of course.)

What I’ve learned is that what folks fail to write about email marketing is:

  1. Why you want to have a mailing list (i.e. your purpose) in the first place matters. It matters a lot.
  2. How you feel about your marketing efforts matters. A lot too.
  3. How other people feel (and specifically, the type of people you want in your audience) about your marketing efforts also matters. You guessed it, it matters a lot.

But Paul, you might say, feelings and purpose have no place in analyzing data, metrics or growth! YOU HIPPIE BASTARD. This is business, not a spiritual retreat in the woods with some guy who calls himself Spirit Wolf.

Your purpose

Even if you’re a pragmatist at heart, your purpose should be a guiding factor in how you approach newsletters. Why? Because it’s basically the lens through which you filter all your list decisions, from tiny to massive.

If your purpose is simply to make money or make a living from your list, it’s good to know this from the start. Or, if the reason you need a list is to build awareness of your brand, that’s important to know too. While money or fame seem like great motivators, most people aren’t solely motivated by those things. A purpose is typically a bit (or a lot) deeper.

Figuring out your purpose determines what you’ll be willing to do (or not do) to achieve your goals. And your purpose isn’t always some quick-and-easy decision either. It can require actual reflection or business strategy. But once you figure it out, it becomes your guide in everything you do.

There isn’t a single way to dig up what your purpose for your list might be. But here are some helpful questions you can start asking yourself:

Defining your purpose has more to do with your personal values, morals and ethics than business plans or marketing strategies. You can’t fake your purpose. Your gut simply won’t let you. And really, why would you want to? You’ll get so much more enjoyment and satisfaction from running your business in alignment with your purpose.

Your marketing style

With your purpose in mind, you can start to think about the scary act of actually promoting your mailing list to the people you’d like to have on it.

In order for anyone to sign up for your list, you have to ask them. Most people will say no (i.e. they won’t sign up). That’s ok. This is actually a good thing, since most people aren’t a good fit for your list anyway (i.e. they’d never buy anything from you, support your business or even get what you’re saying).

This is where most folks go wrong, start to feel icky, then abandon ship like it just hit an iceberg.

You tried pop-ups, freebies, take-overs, all of the things some expert online said to do! And maybe some worked a little. But they didn’t feel like you. That’s because a strategy that doesn’t align with your real purpose never feels good. And most people give up on promotion because things don’t align.

You can’t just blindly apply advice on growing your list or you’ll end up with this. Which would be more hilarious if it wasn’t the sad state of email marketing currently. You can’t just add a ton of sign-up forms to your site and hope for the best.

There has to be an intermediate step: does this marketing tactic actually feel like me? Does it match my brand/personality? Do I feel good doing it? Will my audience feel good seeing it? My own signup as a fun thank you page, because that feels like me.

To back up slightly, being afraid of something is a shitty reason not to do something. We all feel like impostors or like no one will like what we’re promoting sometimes. That’s not the same as “this feels wrong” or “this doesn’t feel like how I want to show up in the world”.

Your marketing style is both difficult and easy to find. It’s easy, because it’s just you. The real you. You market by being a human being (congrats, you’ve achieved/unlocked this goal)! People sign-up and then buy from you because they know you’re a person, just like they are, not some marketing robot or super-profesh internet-superstar. We’re all just humans, separated by screens.

It’s difficult in that it’s sometimes hard to express who you are. In writing, that can take work, mostly involving writing a lot, seeing what sounds like your real, authentic voice and scrapping the rest.

This is the main way that you stand out, in any industry. If you’re a yoga teacher, your unique style is what makes you different from other teachers (maybe you swear a lot or relate yoga sutras to 8 types of Harley motorcycles). If you’re a life coach, you teach similar things to other life coaches, but maybe your style is that you used to be a musician, so everything that comes from you holds some punk-rock flare. Style makes people notice you for you.

Your marketing style applies to everything about your list. How you promote it, what you say to get people to want to sign up, what they see when they do actually sign up. Not to mention, how you keep them engaged for weeks, months, years, once they’re on your list. If you’ve got a pop-up, your style dictates what that pop-up says. If you’ve got a freebie or content upgrade or landing page for your list, those things describe your style.

Your marketing style also lets you break the “marketing rules” if the rule doesn’t align with your purpose. That’s why I don’t have a freebie for my list (the only incentive is “get my writing” because that’s what my list’s purpose is, to share my ideas freely to inspire action or critical thought).

Play with your style to see what fits and what doesn’t, because sometimes the only way to know if something is right or wrong for your list or it’s purpose is to try it and experiment with it.

Your audience (and how they feel)

Most people shouldn’t be on your list. You actually don’t want most people on your list. That’d be bad even if the vanity metric of “X SUBSCRIBERS” looks and feels legit.

But I get it. You want a bigger list. You want to reach more eyeballs than you do now because that unlocks more revenue or more industry standing. All this talk about purpose and style is great, but… GIMME MOOAAAAAR.

More happens in a seemingly counter-intuitive way. That’s because more happens when you focus on the audience you’ve already got. And more specifically, when you focus on how your current audience feels about who you are and what you do.

Your current audience already pays attention to you (regardless of if it’s 1 one person or 100,000 people). If you’re engaged with your list, what you’re sending them is helpful or useful or actionable or entertaining. You want to make sure you’re paying attention to them, what they’re talking about, what they’re asking, what’s resonating (or not resonating) with them. You need to get to know these people in order to find more of them (See? There’s the more!).

More happens when your audience shares what you do with their own audience. This only happens if they feel like what you’re emailing them is awesome.

In order for someone to want to share you with their own people, think about why you would share someone else’s work. Chances are it’s because they said something smart, interesting, entertaining or useful. You feel good about learning from them, you align with their purpose, their style hits home in a unique way, so you want to tell others (and you do). Now you’re helping them grow their audience.

People will do the same for you. But only if you make them feel like they need to share. You can’t just talk to them when you want something from them, i.e. when you have a product to sell. You’ve got to make them feel like you’re constantly giving them valuable and generous information. This can’t be faked (people have great bullshit sensors).

Your audience is a group of individuals who share a common idea, feeling, motivation or pain. Each one is more unique than they are similar. It’s easy to overlook the humanity when staring at numbers on a screen, but there are people on the other end of each of those numbers. People, each with their own lives, struggles and satisfactions.

Solely looking for growth is not enough, and frankly, it’s a horrible goal. You can’t just wish it into being. You need to take lots and lots of small steps towards it: test ideas, analyze results and adapt/change as necessary. And all along the way, you’ve got to make sure that what you’re putting out there is making your audience feel like they want to share it with their own audience.

To sum up and bring it back from the theoretical

  1. If your list is important to your business, and the purpose of your business, make it the most important thing on your website. A sales page or article may only get one single chance to convert, whereas a list gets a chance every time you send out an email.
  2. Give your list a dedicated page on your site, where the only information on it is why someone should sign up, a bit of social proof and one big-ass sign up form. Like Tobias’ (it helps that his newsletter is awesome too).
  3. Before you interrupt a visitor with pop-ups, sliders, scroll-downs and all the things… make sure it feels like you and provides some sort of value to them. If you’re going to interrupt someone, make sure there’s a good reason to do it.
  4. Your homepage should focus on your mailing list. Make sure it’s one of the first things folks see.
  5. If you’ve got a free incentive, make sure it’s useful to the specific audience you’re trying to build and easy to consume (i.e. not a 1,386 page ebook or 6-hour video).
  6. Test all your ideas. The wording, the placement, the design. Then test again. Then continue to test. Test not just what works or doesn’t, but how each idea or hypothesis makes you feel.
  7. Make sure every road leads back to your list. Your Twitter bio URL. Your Facebook page. Your Google+ profile (just kidding, no one cares about Google+).
  8. Rally your list around a common goal, task or action.
  9. Make sure your unique voice and style come through in everything from the sign-up wording to the first messages folks see if they subscribe.
  10. Writing emails people want to share is a lot different than giving people lots of ways to share (i.e. all the social share buttons).

So, how do you grow your list? One person at a time. One right person at a time using your own style. And then you start communicating with them, like a human being, and hopefully creating something they want to share with the human beings that they know.

Behind the scenes of a timed online course launch

I’ve used MailChimp for a long time (watch my MailChimp tutorial here). At first, it was to help other folks use newsletters to drive revenue (when I was doing client work and web design). More recently, it’s what I’ve used to communicate and make a living.

So I approached creating a MailChimp course with both of those frames of reference in mind: using newsletter creation/management as a service you sell to others and using a newsletter for your own business. Both cases involve the same thing: using a newsletter to make money.

The setup

Similar to Chimp Essentials runs entirely on WordPress. Unlike Creative Class, this time I used RestrictContentPro to handle payment and memberships.

  1. WordPress – what the site uses for its CMS.
  2. RestrictContentPro (aff link) – creates accounts, sends payments to Stripe and shows the right content to the right people based on their account.
  3. Stripe – processes the money and puts said money into my bank account.
  4. MailChimp (aff link) – obviously, the software I use for the mailing list.
  5. WPComplete – the plugin I built with Zack Gilbert to let students mark lessons as complete.

I go further into the complete setup of a WordPress course here.


As usual, I used WordPress because it’s what I know. And, as usual, I created a totally custom theme for it (more on the style later).

My main concern while building Chimp Essentials was to make sure it was clear that a few things were happening:

  1. That the course was only available Mar 1 – Mar 31, 2016. The homepage took the form of 3 states: the first was prior to Mar 1 when I was promoting that it was coming soon, the second was during the period it was available and the final was after the registration closed.
  2. It was also important to differentiate between normal website viewers, students that had free lessons only and students that had access to the full lessons. So the site changes based on those 3 states: the navigation bar changes, the buttons on the homepage change and links change, depending on what type of user is seeing the site.
  3. That the course illustrated both its fun nature and that it is technical learning geared towards non-technical folks. Which is why there are lots of jokes (I couldn’t help myself) and fairly clear details about what is and is not included.

I wanted to move from Memberful (due to billing issues) and spent far too long looking for a membership alternative that plugged into WordPress. Most were either not feature-packed enough or so bloated with features that they were hard to use.

I chose RCP because it does exactly what I want—it lets me hack what I don’t want to use (using PHP + HTML + CSS lets me customize every public-facing template RCP has) and their support team are top-notch. Seriously, I’ve had 31 support requests/questions that have been answered quickly and thoroughly. Pippin and his team have done well for a reason in the premium plugin market and I’d use RCP again for future courses.

I wish I could have a US-based USD Stripe account (to make receiving money faster and easier), but alas, unless I had a US-based USD bank account—it’s never going to happen (not for a lack of effort on my part, I spent days trying to get a bank account in the US).

All that said, I like Stripe because it just works. It takes money easily and lets me access that money easily.

One caveat is that for Chimp Essentials, I’ve been getting a high number of failed charges. I’ve not yet figured this out, but I did implement some automation, so if a charge fails, that person immediately gets an email with information on how to pay via PayPal.

Since this is a course about MailChimp, the reason for using it is obvious, but I’d have used the software regardless of the topic.

My MailChimp list separates users into a few buckets (though I do not support literally putting users into buckets, that’s just cruel):

  1. People on the waiting list for when the course registration opens or opens again.
  2. People who want the free lessons—and then receive an automation sequence + access. They are kicked off this sequence if they purchase at any time (since it’s 5 emails spread over 5 days).
  3. People who bought the course—and then receive a post-purchase automation sequence + access (mostly checking in to see how the course is going, 4 emails spread over 2 months).
  4. People who bought the course and clicked that they’d recommend the course to friends—and then receive a short affiliate automation sequence.

Too many folks don’t realize that MailChimp’s automation sequences can contain some pretty nifty logic and segmentation (which is partly why I created this course)that helps not only pitch automated emails at folks who already bought but also to only pitch things like affiliate programs to those interested in telling other people.

I’ll also note that I’m still hosting the course on FlyWheel (aff link). They continue to be awesome and the site continues to run smoothly even when I do crazy things like send 30,000 people to it from my email list at exactly the same time.


This was my first foray into a timed launch (meaning the course registration is only open for a fixed time). It makes sense for Chimp Essentials since it’s technical training based on someone else’s software.

MailChimp, and even WordPress, SquareSpace, Zapier and Google Analytics all have new features and interface updates fairly regularly. I wanted to keep the lessons up to date when they were being sold, so I set the registration to close after 4 weeks. And I’m glad I did because Zapier already changed their interface (it’s WAY better now too, so good work on that Zapier folks!).

I was also curious if a timed launch would impact or affect sales in any way. At first, it was just like any regular launch I’ve done, weighted heavily during the first few days and trailing off to slower but steady sales thereafter.

I also think sales spiked right at the start because on Mar 1 I already had 1,000+ people on the waiting list and that day I launched to over 30,000 people on my PJRVS and Creative Class lists (who I had been telling about the course for months). So I launched to a group of folks who a) already knew what it was about and that it was coming out, b) had expressed interest in it and c) had tested the shit out of it (see my note on beta testers further down).

True to what I’ve read and was expecting, sales also had a spike during the last few days. But that sales spike pretty much mirrored a multiple launch situation that I’ve done with Creative Class several times. Meaning, I don’t think an evergreen course is better or worse than a timed launch course (which is contrary to what loads of marketing folks tell you). I just think that you have to be smart about how you run each option.

Since this was a course about newsletters and the power of a list to generate revenue, I kept almost all my launch efforts to my own lists. The only exceptions included spending $650 to advertise in two other newsletters I thought were a great fit and my affiliates (more on both later).

As I’ve noticed over the past few years, all sales spikes happened when I sent out emails to my list telling them about a launch, a discount or the registration closing. True to form, the ROI I get from my own mailing list is insanely awesome (at about 12,000% or, for every $1 I spend on MailChimp, I make $120).

As with Creative Class, I beta-tested the crap out of this course. I had almost 50 folks go through onboarding, payment and the course itself. I asked them to make sure the lessons made sense, were paced well and covered the necessary topics. They all paid for access, although at a massive discount. This took about 20 hours of work on my part and was time well spent since I made a lot of tweaks based on their feedback.


Here’s the basic rundown of timeline and events for the course:

  1. Dec 2015: Planned out and researched the course.
  2. Jan 2016: Recorded all the lessons and wrote all automation sequences (pre-launch, free lessons, paid lessons).
  3. Jan 25-29: Added the course content and videos to the WordPress site.
  4. Feb 1: Released beta spots at a huge discount for folks to test payment and the lessons.
  5. Feb 2-26: Updated and tweaked the lessons, the payment, the site and had the automation sequences copyedited.
  6. Feb 27: Loaded all automation sequences and segment logic into MailChimp. Sent myself 109343 (or so) test emails.
  7. Feb 27 (late): Updated the code on the homepage to show the buy button (instead of the pre-register button) and added a countdown timer for the month of March.
  8. Feb 28: Told the Chimp Essentials and PJRVS lists that the course is now available at a discount for 48 hours.
  9. Feb 29: Hosted a live webinar to answer any/all email marketing questions.
  10. Feb 29: Posted Chimp Essentials on ProductHunt (it did well that day!).
  11. Mar 1: Told the Creative Class list about the new course.
  12. Mar 1: Released an episode of The Freelancer that was simply a pitch for the course.
  13. Mar 2: Let my affiliates know about selling the course and gave them a goodie pack.
  14. Mar: Wrote 11 articles about emails, newsletters, email marketing and sent some to my lists, some on my sites, some on other people’s sites and some to business publications.
  15. Mar 29: Sent a “3 days left to buy” email to the Chimp Essentials list (segmenting out folks who already bought).
  16. Mar 31: Sent a “12 hours left!” email to the Chimp Essentials list (segmenting out folks who already bought).
  17. Apr 1: Slept. Just kidding, I worked in my garden.

Payment + startup costs

The only transaction fee I pay is Stripe’s 2.9% + 30¢. Past that my costs are fixed.

  1. MailChimp runs me just under $250/month for my PJRVS, Creative Class and Chimp Essentials lists. Currently the Chimp Essentials list is slightly under 4,000 people spread across interested, free lessons, paid accounts and affiliates. So if I was tracking just that list’s cost, it’d be $50/month.
  2. FlyWheel is $25/month ($15 for hosting, $10 for SSL).
  3. I spent $9 on an SSL certificate from NameCheap (NOTE: Flywheel offers free SSL now).
  4. I spent $13 on a domain from Hover (who I’ve moved all my domains over to recently).
  5. I bought two stock photos for $50 from Stocksy of monkeys doing funny things for images in my tweets and grams.
  6. I purchased a few WordPress plugins to make the site work. MC4WP to push emails from WordPress to MailChimp for $49. RestrictContentPro was $42. AffiliateWP was $199.
  7. I spent $50 on the music that’s at the start and finish of every lesson (and it’s AWESOME) from PremiumBeat.
  8. I spent $650 to advertise in two newsletters.

So in total, my starting costs were $1,137 for the setup and first month. I wanted to stay around $1,000 to create this course, so I was pretty close.

Ongoing, I’m spending $75/month on MailChimp and hosting. If I open registration twice a year, or 2 months a year, that means I’m spending $750 on the 10 months it’s not for sale.

I’m spending $4.56/user on Stripe. This isn’t bad since I’m getting $147/user. So a single sale covers my monthly costs and 8 sales covered my startup costs. 5 sales cover the 10 non-revenue months. Outside of time and research (which is obviously a massive investment), that’s a lot less than a hosted course platform or a platform that takes a large percentage of each sale.

I didn’t track this, but it took me about 3 weeks to record, edit and master all the lessons, working a few hours a day on it. It took me about a month to put together the lesson plan, go through each lesson a few times as dry runs (so it came easier/more naturally when it was being recorded) and even learn a few things I wasn’t aware of. I wanted to make sure I was the most “experting” expert that every expressed expertise about MailChimp ever. I even contacted their support a few times to ensure I was correct in what I was saying. I also got vetted and approved as a real MailChimp expert.

I don’t take teaching anything lightly, and I want to maintain the trust my existing audience puts in my products, so it took a while to get everything where I wanted it to be in terms of the knowledge doled out. I also spent a lot of time beta testing and self testing everything.

I’d guess the course was about 100 hours invested in learning and teaching the lessons and 30 hours invested in designing the site, programming it and setting up the functionality it needed to run.


I still don’t know that much about affiliate programs. For Chimp Essentials, I tried one (with the best plugin there is for affiliates in WordPress) and could granularly track each affiliate’s clicks, leads and even successful paid referrals. I also created a digital goodie pack with videos, images, text and ideas for sharing.

9% of sales came from affiliates. This might be awful or the norm, I don’t know and honestly, I don’t care. The folks who signed up to be affiliates were pleased with how it all worked and everything worked the way it was supposed to for tracking. So regardless of metrics, I’m happy that an extra 9% of revenue was created and shared equally between the affiliates and myself.

I’d do it again and perhaps offer even more in terms of ideas, files and information. I’d also spend some time talking to the best affiliates about what I can do better or help with more.

Styling + setup

The site
Since I’ve been a designer/coder for so long (since I invented the internet), I wanted to build the course’s design and theme myself. Yes, this made things take longer, but still, it’s my course and I have the skills, so why not flex them a little?

I don’t recommend designing and programming your own custom WordPress theme unless that’s what you do. If it’s not, buy a theme or sell your course in a place that styles things easily for you. It’s faster, easier and smarter than learning how to do all that yourself. And no, the theme I created for Chimp Essentials is not for sale (answering this now because I get a few emails a week asking if folks can buy my course themes).

The style had to be both quirky and fun. I am pretty bored with the web design industry as a whole, since it’s so derivative. I went so far left of centre with the design of the Chimp Essentials brand that I was actually worried before launch if it was going to hit the mark. I used a very unpopular typeface (Sentinel), a rainbow logo and an almost-non-existent interface design. I took inspiration mostly from 1970s architecture magazines (which makes me sound like a hipster, but that’s just what was on hand).

Luckily, being a podcaster, I already have an amazing mic, the Rode Podcaster. So all I needed to do was record myself talking into it while I moved through screens on my computer.

I used Quicktime to record all the videos. Laugh if you want, but it’s the easiest and cheapest (since it’s free on a Mac) way to record screencasts. I edited the audio in Garageband and the videos in iMovie, neither of which are “professional” grade software, but they do the job and do it quickly.

Most videos took a few takes and a few cuts. I also tried hard (unsuccessfully at times) to go slowly, which I always have a problem with since I talk and click around things too quickly. So I required several takes in some places. I bookended each video with some simple text and my silly $5 theme song for the course.

Sales + numbers

This is what you’ve all been waiting for, right? How much the course made? GIMME THE NUMBERS PAUL. Ok, fine.

Well, currently there are 560 paying students which have generated $55,062 in gross revenue. The mathematically astute of you will notice that the revenue per student is less than the $147 regular price, and that’s because there were several discounts early on and a few discounts offered to affiliates as well for their people.

Transaction fees were approximately $1,500, the setup plus first month cost me $1,137 and $5,071 went to affiliates. So of the $55,062 gross, I received $48.899 (not including the ridiculous amount of taxes I’ll pay both personally and corporately, nor the costs of my bookkeeper, lawyer, copyeditor and accountant). Still, for 3 months of work, (2 for creating, 1 for launching) that’s not bad. I took one of the four launch weeks off too, so I could probably have done even better.

I didn’t have a revenue goal when I launched this. I tend not to set goals as they either disappoint or become irrelevant. I wanted to make a course that I enjoyed creating (check!) and that folks got a metric shit-ton of value from (based on feedback, that’s also a definite check!).

As I mentioned earlier, pretty much all of the sales came from email (which is good, since that’s what I teach in the course) – either from my own list, my Creative Class list, the Chimp Essentials notification list or the free lessons list. Those free lessons converted nicely.

Outside of hosting one “just me talking” webinar (which generated 21 sales) and releasing an episode of The Freelancer about the course (which generated 7 sales), email marketing was all I focused on. I sent the occasional tweet, but those never do much in terms of direct conversions. I also didn’t run any social or search ads, but I spent $650 to sponsor a few newsletters (which netted less than $300 in revenue or rather, two sales, so not worth it).

Most importantly, not one paying student complained about the course, not a single person asked for a refund and the only people who had negative things to say about the course were folks on social media who a) have never signed up for my mailing list, b) never signed up for the free lessons and c) obviously never bought the paid course. Haters gonna hate, potatoes gonna potate…

To summarize

For this course, I don’t think there’s anything I’d do differently. Although it’s currently nowhere near the sales figures of Creative Class, it’s done well out of the gate and there weren’t any major setbacks or screw-ups on my part.

I was happy making it, and although launching it was full of self-imposed stress and anxiety, feedback has been great. As per usual, just before launch I figured that everyone would hate it, no one would buy it and everyone on my current lists would leave. Obviously none of those things happened, since they never do, but still – those feels never go away for me. I just push forward regardless.

I stuck to around $1,000 to create the whole thing, which goes to show that you don’t need to spend a ton of money to create a great course. I also didn’t hire anyone to help, outside of my copyeditor to look over the text in the automation sequences.

I already have a ton of ideas for new lessons, updates and improvements to the course and structure, so I plan to relaunch this fall, after updating the lessons that need updating based on feature and interface tweaks to the software.

Want to make a great course that delights both the people who take it and your bank account? Find a topic people are willing to pay to learn about. How? Listen to what people are asking you for, then ask for their money in exchange for teaching them what they asked for. Test your assumptions and ideas with beta testers. Launch smartly and quickly to people who are expecting the course and segment your lists to send the right emails to the right people at the right time. Focus on the benefits of learning the information, not just the details about what’s included.

And make decisions quickly, since they don’t really matter. Getting stuck on any one decision you need to make means progress and every single future decision has totally stalled out. Decide to move forward and don’t bother trying to figure out what the “best” or “most right” decision is. You’ll learn that later, either because you made the wrong decision and need to change something or because you chose correctly.

People get so hung up on software, payment processors, how many lessons to have, how long they should be, what the course should cost, what to A/B test… when really it’s best to just pick something, move forward and launch the thing. You can change your mind later, based on data from paying customers.

Keep in mind that the notion of passive income is really just a disjoint between effort and revenue. Although I’m sure some nights I made thousands while I slept or watched season 2 of DareDevil, that’s only because I did around 150 hours of work prior to making a penny on the course. You can’t make money without doing a lot of work. Products separate effort from money and also separate fixed hours resulting in fixed revenue (since you can potentially generate a lot more money than hours worked).

So if you’re thinking about launching an online course, know that it’s not a magical gravy train ride where leprechauns in suits dump money at you from the caboose. But you can do this. Cheaply and fairly easily too. You just have to commit to a constant forward momentum and not let any single decision derail it.

Dear FNAME, newsletter personalization isn’t what you think it is

Email easily has more lives than the luckiest cat. It’s been declared dead so many times in the last few years that I’ve lost count of funerals held in its honour.

The truth is, from my own business and every business I know that does email well, it’s still (by far) the best way to reach a captive audience. Better than ads, better than social and far better than funeral announcements in the classifieds.

My theory about the “sorry, email died” camp is that they simply aren’t taking advantage of the way email now works, because it’s changed dramatically in the last few years.

In the beginning, email marketing was done in basically the same way that junk mail in your physical mailbox is done: you get a massive list of people with varying interests and just blast the crap out of them with special offers and deals. Email blasts were sent with about as much precision as using a firehose to water a tiny seedling, hoping no other plants or assorted shrubbery would perish in the torrent of water.

These days, emailing a newsletter can be as exact as a surgeon using one of those science-looking droppers to give a seedling the exact amount of water it needs, based on data, at exactly the right time.

So how do you go from out of control fire hose to science-dropper? By personalizing the why, who and when of your mailing.

Good personalization combines all three of the above – subscribers get emails from you because of something specific they did, bought or showed an interested in at the exact time it makes sense.

Effective personalization is the result of smartly segmenting your list, so you’re able to send emails based on why, who and when. By segmenting your list into groups of people with similar traits, interests, purchase histories, etc – you can get much better results with your email marketing. Not just higher revenue, but higher engagement, trust and enjoyment when you start sending emails that are specifically relevant to each reader.

Segmentation logic and reasoning

To start, you can use MailChimp to split your list into two segments: active and inactive.

You do this by creating a segment – go to your list, then MANAGE SUBSCRIBERS, then SEGMENTS – and setting two basic conditions:

If one of your subscribers received the last 20 campaigns but didn’t open any of them, they’re probably inactive. This means that every month you’re paying to keep these people on your list, but they don’t care to be on it.

But this is just the tip of the personalization iceberg. Where personalization really hits its stride is when you start to segment based on:

How do you find this information? You push user data from your ecommerce system or website to MailChimp. This is done through hidden merge fields or integration with your ecommerce system.

(You can learn more about setting up merge fields by taking my Chimp Essentials course.)

When you do this your list goes from “everyone gets everything” to “certain people get relevant things, when they need them”. The latter sounds a lot better, yes?

In MailChimp’s research, they sampled campaigns sent to 9 million subscribers. Then, they compared the results between segmented campaigns and non-segmented campaigns and found that segmented ones had almost 15% more opens, and almost 60% more clicks per campaign.

Ways to segment your list that make your WHY, WHO and WHEN work for your list and its subscribers

The following tips are a few things you can do to personalize your campaign a little more and get it into the inboxes of the right segments of your audience.

Sometimes it’s not you, it’s them. People routinely sign up for lists they aren’t right for or never wanted to engage with in the first place. But you’re paying for those people, every month, to take up space on your list.

Now you’ve got a few options. You can delete all those people from that inactive segment and call it a day—saving money and increasing your open/click rate in the future. Or, you can try a re-engagement campaign, since inactive subscribers can still be about a third as useful as active ones according to a recent study by MailChimp.

If none of the re-engagement campaigns work, remove those people from your list and count the extra money you’ll save each month moving forward without them. Or keep them, since inactive subscribers can be worth around 33% as much as active ones, in terms of revenue—sometimes.

Purchasers and non-purchasers
A great way to reward people who’ve bought something from you is to give them something a little extra or unexpected. Whether it’s a free bonus that relates to what they’ve bought or a great discount on a related product, people like to be treated like their spending matters to you.

Since you can segment purchasers, you can also segment and personalize emails to people on your list who have not purchased something. This works great when you’re having a sale or deal on a product, since you don’t want to let people who’ve already bought that product (possibly at full price) know that it’s now cheaper than what they paid for it.

Page source
By creating a single hidden merge field on your signup forms, and populating it with the page title or page URL, you can easily segment or even automate campaigns based on where people signed up.

If subscribers sign up from your “About” page, that’s not that big of a deal or useful for personalization. But say you have a podcast page, or a page for a specific webinar, then hey now! That’s where page source segments get fun and useful. You can use those segments to create specific welcome emails or even automation sequences (for example: pre and post webinar).

Star rating
Without having to set up or create anything, MailChimp rates your subscribers based on activity. They take into account open rates, clicking activity and several other variables to give each person a rating of 1 to 5 stars.

With a segment of 4+ stars, you can offer your best subscribers (since they’re the ones who open, click and engage with your list the most) special deals, exclusive offers or even early access to what you create.

Total revenue
If you sell multiple products or even single products with multiple tiers, it can make a lot of sense to send different emails to different groups, based on how much they spend.

For example, you may want to try to upsell people who’ve only bought a small amount from you with bigger and better products. Or, you might want to treat your big spenders to early access or big discounts on future products.

You can either track revenue by using MailChimp’s eCommerce360 or push data into your list from your ecommerce system using Zapier.

Finished automation
Automation sequences are great, but you don’t want to have subscribers finish one, and then leave them out to dry without any further personalization. MailChimp lets you add a “post sending list action” which allows you to update a merge field, remove someone from a group or even delete them off your list.

Maybe they loved your automation sequence pitching your paid product but the time wasn’t right for them to buy. Maybe in finishing the automation sequence you want to add them to another sequence (segmented based on a merge field the post-sending action would add them to). The sky’s the limit.

Personalization is everything

While personalizing campaigns with segmentation can be super powerful, they’re also not guaranteed to work for everyone, all of the time. The best way to see what works (or doesn’t) is to start using your segments and testing your results against non-segmented campaigns.

Then you’ll be able to properly see what’s best for your business, your subscribers and your list.

Personalization is more than just adding “Hello FNAME” to the start of your emails. It’s about figuring out the reason why you’re sending something, who should specifically receive it and when those emails should be delivered. You’ve got to take into account where and how they signed up, what they’ve purchased (or not purchased), their geographic location, there activity in your app or on your site and several other factors. Use your data to target specific people, instead of a firehose approach of “let’s just send EVERYTHING to EVERYONE!”

From there you’ll never declare email has died again (unless it gets caught up in a zombie apocalypse, but if that happens, you’ve got more pressing things to worry about).

Make automation great again

Have you ever had to call a large company (like your internet provider, credit card company or even (possibly the worst of them all), Paypal)?

  1. You’re welcomed by a friendly but fake voice that tells you how important you are to their business.
  2. They ask you to state your problem and you respond, “I’m having trouble connecting to the internet”, at which point they repeat back, “Sorry, ‘half the treble of the comet internet’ is not a valid phrase”.
  3. You press 0 a few times, which is apparently invalid. You try * a few times and the friendly, fake voice tells you that that’s also not a valid option.
  4. You say, now in a haggard voice, “I want to talk to a human!”
  5. The fake voice says, “I’m sorry, ‘team of Cubans’ is not a valid option.”
  6. You contemplate cancelling your service with this company, but fear you’ll be subjected to an even worse game of telephone on the telephone (get it?!) and think better of it.
  7. Defeated, you Google your problem instead (from your phone), or just complain about it on social media.

This kind of experience is what most folks think about when they think of “automating” part of their business. Soulless, machine absurdity that enrages paying customers.

The thing is that the above example is only an illustration of how to do automation completely and utterly wrong (unless your goal is comic relief or HULK SMASHING anger, in which case I’d suggest you do exactly that).

In fact, I automate most of my business. I have to. I’m one person, running a freelance company, 4 courses, 2 podcasts, a few mailing lists and more – without any help.

However, unlike touch tone call prompts, I automate my business in a way that doesn’t consciously register, let alone register negatively people.

When you signed up for this mailing list, for instance, you were greeted with an email expressing my gratitude in the form of a new tattoo of your name. You realized (since you’re smart like that) that I didn’t write and send that email specifically to you. But you were also (hopefully) not pissed off that I automated the message either.

According to research, 75% of folks actually expect a welcome message when they subscribe to a newsletter. To put on my marketer hat for a second (I’ll switch back to my normal toque right after), welcome emails also generate 320% more revenue than any other promotional email.

As Vero says, “Welcome emails are the Daryl Dixon of lifecycle email marketing. Soft-spoken, sometimes overlooked yet always kicking ass.”

(Apologies for those of you who don’t watch Walking Dead.)

A welcome message for a mailing list is a type of automation that most folks do without realizing they’re in the “automation game”. And, if it’s done right, on brand, and in a way that surprises + delights the person on the other end, you can chalk up your first automation win. Go you!

In this way, automation acts as an extension of you and your business. As such, it should be in your own style and in your own voice (not the PayPal, “You are important to us, please continue to hold for 230,943 minutes until someone can read you canned and unhelpful responses.”). Automation can be interesting as well, like a silly story about tattoos, or something else that might amuse the person reading it.

I automated almost my entire onboarding process for new web design clients. This saved me hours of work a week and didn’t even slightly decrease the average number of leads that turned into paying clients.

With tools like Zapier, you can get really smart with automation, without having to do any programming. I use their service to automatically send an email whenever a credit card charge fails for my courses. This happens a few times a week, mostly (I think) because I’m in a non-US country and credit card companies don’t trust dirty, socialist foreigners. But if I did nothing about failed transactions, I’d lose all those sales.

So instead of letting those transactions fail and hope the person tries again, I use Zapier to send them an email letting them know that it probably wasn’t their fault along with instructions that explain how to pay via another method.

That email is sent within seconds of the failed charge. It comes from my email account and is written the same way I write personal emails (no capital letters, bad humour and my normal email signature). They don’t have to contact me for help. They don’t have to wait for me to get up (if they’re trying to pay at 3am PST). They are immediately contacted with a friendly email with simple steps to solve their problem. Perhaps unsurprisingly, that email has a 96% success rate.

I also use my mailing list to automate every aspect of the courses I sell. This setup enables me to run a few different courses with lots of students and still just be a single person running everything.

Most of my courses have a free or “try before you buy” option. So if you’re interested, you can snag a few free lessons by giving me your email address. With MailChimp’s automation sequences, I start sending lessons or emails right away – so you get what you signed up for immediately. And then, one per day, where each one shares a little more information, samples or content with you.

And here’s where it gets interesting… I also use MailChimp to immediately segment off paid students from any free automations. Meaning if you buy the course during the free automation sequence (Hooray! You’re the absolute best.), you will stop getting those emails right away. You just bought the course, after all, so there’s no need to continue sending you the free stuff!

Then, you are added to a post-purchase sequence. I’ve found these work really well to a) show someone how to use the course b) how to access all the features/lessons and c) how to get the most out of the course material. With a few automated emails explaining those points, I only get about one email a week (out of ~4000 active students across all of my courses) for support requests.

Most of my post-purchase automation sequences also include some feedback loops, to see what people think of the course they bought, to make sure they’re doing the work and to check in with them later on to see what positive outcomes they’ve seen from the course (which is a great way to mine for testimonials and success stories). Feedback can also be tied into its own automation by using tools like Typeform to ask and collect answers.

The possibilities for automating your mailing list and your business are endless. And if you do it correctly, your audience or even your customers will be happy to be taken care of with your personal, albeit automated touch.

Leave the internet comets and teams of Cubans to big companies who suck at taking care of their customers. You can use automation to be an extension of your own unique and personal style and for the actual benefit of those coming in contact with you (even if it’s at 3am, when you’re sound asleep).

Behind the scenes of The Sunday Dispatches

I want to take you on a behind-the-scenes look at this list. Transparency and all that.


The Sunday Dispatches has been my weekly newsletter since November of 2013. The goal has never been growth, sales, or some sort of world domination scheme involving robots (or to a lesser extent, aliens). My focus has always been telling stories to the folks that might enjoy them, and hearing their stories, too.

I do a lot of research, listening, and communicating with this list because I like to know what you’re all working on, thinking about, and even struggling with. It informs the topics I write about, and sometimes even the products I create.

MailChimp is what runs this list. It has always been what runs this list. I get lots of emails about why I choose MailChimp over Infusionsoft, Aweber, Campaign Monitor, robotic carrier pigeons, etc. For me it comes down to three things: it’s easy to use and maintain each week, it looks gorgeous to work with, and the company has my back.


This list is my biggest “service” expense for running my company. More than my licence to Adobe’s Creative Cloud ($420/yr), and much more than hosting (which is around $350/yr). And technically, it doesn’t generate any direct revenue because it’s completely free to join.

What this list does do, and why I continue to spend money on it, is promote my work in a way that I feel comfortable with. Curious about my writing but don’t want to buy a book or course? Read my list for a while to get a taste. Aren’t sure about if a $400 consult with me is right for you? Get a sense of my style, focus, and knowledge for free. Don’t know who won the Super Bowl? Well, for that this list probably can’t help…

Sure, once or twice a year I have something available for sale here, but mostly I focus on telling a new story every week. The footer always links to what I’m working on and that drives enough sales to cover the costs.

Now onto the nitty-gritty of expenses per year. These are approximates since some costs change due to list size and some aren’t always constant (like illustrations).

That doesn’t include my time either, which if I billed out at my normal rate of $150/hr would be around $15,000 (two hours a week for writing at minimum). And that doesn’t include conversations and replies to subscribers, which is typically two hours a week (because I get 60+ emails a week from subscribers).

Growth & numbers

The number of people I’ve deleted from my list is 6,487. That’s about half what my list is currently. Every few months I run a report to see who hasn’t opened the last 10 emails and I delete them. Sure, I could keep them to pad my numbers, but I pay for each subscriber, so I’m not going to pay for people that aren’t paying attention.

I also delete people who are mean or rude. On average I get 3–4 nasty/mean unsubscribes a week and typically one person complaining about how awful of a writer or person I am. Or how I’m a narcissistic robot/alien who’s mean to carrier pigeons. I need them on my list as much as a fish needs a bicycle.

Top subscription sources

Oddly, the best place for me to gain new subscribers is when I send out newsletters. This is because people share links to those newsletters, and I’ve got a bit of writing that only non-subscribers see at the top and bottom of each newsletter asking them to sign up .

In my consulting and design business, I’m a huge advocate of a dedicated page for a newsletter sign-up for all my clients. That’s because I see it work so well for myself and my clients who do it. We use that link in our social media profiles, in bylines for articles we write for other publications, and even in our email signatures.

I know, I know, everyone hates pop-ups. That’s fine, I get it. But they work. I wish they didn’t, but they work so well it’s scary. Mine only fires off once per person and only when you move your mouse to close the window or tab. It uses this script called OuiBounce. It also has some humour, “No thanks, I hate creativity,” because if you don’t get my silly sense of humour, this list is probably not for you. People who sign up through the pop-up are no less likely to unsubscribe and sometimes (because I track where people sign up from) they go on to be the folks who share my newsletters the most.

Top list building tools

In the beginning, the biggest bumps in signups came from writing articles for other publications. The first piece I published in Fast Company got me close to 500 signups. My first piece for Smashing Magazine got around 300. What I’ve noticed is that the first time you write for a new publication is the best chance to gain signups. After that, their audience has already heard of you and signed up if they were interested.

Anytime I write, get interviewed, or create a profile somewhere, I always put my URL as (the dedicated signup page). I get as many page views on that as I do my homepage. I’d much rather people test the waters with my style before buying something, so I promote my list more than my paid products on my own website.

I’ve kept a pretty hard line about incentives and my own mailing list. I always figured the only reason I want someone on this list is because they want to read my writing and not just get some ephemeral PDF download they may not even read. That said, I have tried two incentives that did drive a lot of signups (but then, as I figured, a lot of unsubscribes as well).


Most people forget that they can customize the messaging a new subscriber sees. The form, the confirmation email, the thank you page and the final welcome email are all editable for both design and content in most newsletter systems. I’ve spent hours and hours tweaking how people are onboarded to my list because I want it to reflect the list and my personality.

My welcome message (if you’ve forgot or signed up in the first few months before I had it) talks about me being so pleased you joined the list I went out and got your name tattooed on my inner, left arm. It’s more fun than “Welcome to my list!” I also like it more than, “You’ve got 5 minutes to buy my products at a tiny discount, STARTING… NOW!!”

Sure, I have an offer to get my books at 50% off (pro tip: that link never expires) and a few PDFs, but the main focus of the first email is to show people that while this might be a list about working for yourself, creativity, and freelancing, I’m still going to have fun with it.

Closing thoughts

Out of all the products I’ve launched over the years, this list has been my favourite. It’s also the only one I come back to week after week to build on.

I enjoy writing new articles each week because it helps me be a better writer. I don’t know how else to do that except to write more, and write publicly. It also helps me connect directly with you—the type of folks I enjoy connecting with.

We’ve all heard that mailing lists drive revenue and all that, but for me it’s a little more. I feel like after years of searching, I’ve somehow managed to gather up all my rat people in one place.

How to run your mailing list like a total jerk

Everybody (myself included) is always going on and on about how important it is to have a mailing list for your business. It’s the easiest way to keep in touch with your audience and it nets the highest conversions when you’re selling things. The draw to build your list’s subscribers is heard far and wide.

When someone subscribes to your email list, they’ve just given you a sacred bit of permission.

Your subscribers let you appear somewhere they spend a lot of time (their inbox) and in turn, you promise not to abuse your newfound power.

Too often though, I see people taking their subscribers for granted, or worse, treating them like shit.

Stuff like this:

Automatically putting someone on your mailing list just because they bought something you sell

An ecommerce transaction isn’t the same as subscribing to a mailing list that sends out frequent emails. If they’ve already bought something from you, include your mailing list as a link in the receipt or as an opt-in at checkout. At most, email them ONCE to remind them if they bought something from you, they may also be interested in your main list.

Adding someone to your mailing list just because you subscribed to theirs

This happens a few times a week to me. I get an email from a mailing list I didn’t subscribe to, only to see that they subscribed to my list the week before. Not only is this a jerk move, it’s also stupid—it’s fairly obvious the first email I get that you added me without my permission, and I’m immediately going to report it as spam.

Adding someone to your list because they emailed you once

This is also a different type of transaction. Emailing you once isn’t the same as giving you permission to add them to your mailing list. Unless my email starts “I DON’T WANT ANYTHING EXCEPT TO BE ADDED TO YOUR MAILING LIST”. Otherwise, don’t do it.

Adding someone to your list because you have their business card

See points #2 and #3. This is a separate and different transaction. Total dick move.

Adding someone to your list because they attended/are attending your event

If you have event-related emails, like a venue, date, time, speaker change, that’s exactly what you’ve got my email address for. If you want to sell or give my email to your event sponsors, that’s not cool at all. If you want to email me after the event with product announcements, blatantly trying to sell me things that are totally unrelated to the event I attended? Definitely not cool.

Unsubscription confirmation

I know I unsubscribed. I don’t need to be reminded how much I didn’t want to be on your list. You’re not going to win me back with one final plea. We broke up. Move on.

Excessive goal-based reminders

If your list uses goals to track subscriber activity, you don’t need to remind me every few days that I haven’t done what you wanted me to do. You can’t control me – you’re not my mother!

Adding subscribers to multiple lists

I signed up for one list, not ALL of your lists.

Not being able to unsubscribe / not accepting unsubscribes

If there’s no clear and visible link to unsubscribe, you’re violating lots of email rules and etiquette. Worse is having a link to unsubscribe but not taking people that click it off your list. There are several lists that I’ve been added to and every week I click “unsubscribe” and the following week I still get emails. Make damn sure your unsubscribe link works. Otherwise, look out for emails from me that start with excessive cursing.

Collecting email addresses from social media

If we connect on social media and it’s on a network that shows my email address, our online friendship doesn’t give you permission to put me on your list. If you do, P.S.: our friendship is over.

Look, I get it. I do.

You want to grow your mailing list. You want to have 1,000s of people salivating for your next email, with their fingers hovering over the buy button (wallets in hand).

Spoiler alert: The only way to do this is by being a real and decent person about it. No jerk moves. No shady tactics. Just provide so much value that people actually want to sign up for your list.

Even if you find success using the methods above, it won’t last. And, you aren’t a jerk. Plus, people will think you’re a total jerk. And when was the last time you bought something from a total jerk?

The Sunday Dispatches newsletter, weekly articles since 2012—written by Paul Jarvis and read by 30k+ subscribers.