The Anatomy of a Six-Figure Email Course

Every online entrepreneur is looking for that “fly-wheel,” a predictable way of spending money and getting more in return. But rarely do we find it. Instead, we hop from random tactic to random tactic. We try Facebook ads and webinars and try and try and try.

I searched for my own El Dorado, my golden fly-wheel two years ago. And after a lot of trial-and-error, I’m now at the point where I can spend about $2.50 on a Facebook ad opt-in and get back $55.80, or about a 22x ROI.

Customer value can increase 22x with an effective email course.

My goal with this guide isn’t to bait you into thinking that there’s “one secret trick” you can use to 22x your acquisition costs in less than a month.

Instead, I’m going to share the thought process that went into me thinking, “I want to put money in and get money out reliably,” and what I ended up trying — complete with examples and results. I’ll tell you about what worked and what didn’t and show you all the juicy statistics I’ve accumulated along the way. This is a story of the messy path to building the business one wants.

But first, it helps to remember the basics of an online business. I see each one composed of “assets.” Some assets pay you in cash, others with the email address of a potential customer. Most of the online business is creating these assets, tweaking them, and getting them to run to perfection.

For this post, we will focus on one of the assets that “pay” you with a potential customer’s email address: a free email course. Why? A rock-solid email course is accessible to the customer but still provides them with tremendous value and prepares them to be the perfect buyer. You must take “free” assets (like an email course) as seriously as your “paid” assets (like a paid course).

Ideal structure: Great content to email course to paid course

Put bluntly, you need to know how your free assets, like email courses, are performing before you can even think about being successful. You must know your KPIs, like acquisition costs or average subscriber values. You also must constantly measure how your subscribers are reacting to the material and be constantly updating it. I won’t sugarcoat it: It’s a ton of work. So my goal here is to tell you everything you need to know to develop a super-profitable email course into your own paid course business.

And the best part?

This email course will be infinitely scalable and repeatable. Meaning: it will work on your behalf each and every week to sell your products or services and won’t require any ongoing input from your end. It will, quite literally, be a money-making machine. But contrary to what we often read, these machines take years to build. (Mine took me two years to get to six figures.)

But before I get to how I built the machine, it’s important to know how I got there and how what seems from the outside like an overnight result was instead several YEARS of trial and error. And if you want to skip around, use the table of contents below:

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Table of Contents

Preface: Drive-bys Don’t Buy

I used to run a web agency. As our team and expenses grew, I needed to create more reliable ways of getting clients. More costs required more revenue. It was the golden fly-wheel but in reverse. We didn’t have any recurring revenue (which I’d fix if I could go back in time), so I had to think of ways to maintain enough lead flow to keep us in business.

So, first up, I tried ads…And (brace yourself) they didn’t work.

Well, they “worked” in getting clicks to our website and putting charges from Google and Facebook on my credit card. But people weren’t buying. Frustrated, we ditched the whole paid ads thing and started working on our local networking strategy. For all of the targeting power of the internet, maybe some old-fashioned networking was in order.

This led to hosting our own networking events in our hometown, which led to us teaching free business seminars to the business community (on topics like building web applications, starting a startup, and so on). And this started to pay off — we ended up with a multi-month pipeline of signed work, primarily sourced from seminar attendees or referrals from attendees. Progress!

Lesson learned: Teach people stuff, and they’re more likely to buy.

Fast forward a few years, and I sold that agency to launch a software company, Planscope. It was a project management app that was made for freelancers and agencies. My job changed from getting clients to selling software.

Rarely did someone actively go out in search of project management software. Few people, I realized, thought they had a project management problem. I had to bridge that knowledge gap with content and thought leadership to sell more software.

So I started to write content for the site’s blog that would target the kind of people who could benefit from Planscope. I’d write about pricing, getting clients, networking, and all the other topics that appealed to the type of person I built the app for.

Like any good content marketer, I had call-to-actions on the blog that linked over to Planscope. But once again, no one was buying. Argh! I was doing all the right tactics. It was the ad effort all over again. But instead of just paying with my money, I paid with hours and hours of writing. But, alas, organic search to the blog post to call-to-action… no results.

It wasn’t until I tried to actually put myself in the shoes of someone who found a blog article of mine that it all started to really make sense:

“I’m frustrated because I think I’m undercharging and keep getting BS clients. I’m going to go to Google to voice my frustration. ‘Hey Google, how do I charge more?’ Now I’m on some website that has a… really interesting… and in-depth article on raising your rates. Stellar! This was great. I think I know what to do now. Oh, wait, there’s more? …Project management software? Hrm. Thanks, but no thanks.”

What I failed to see was that people who were viewing my site didn’t really think they had an issue with project management. They didn’t correlate the way they were being mistreated by their clients with their process for managing projects. They saw them as separate issues, but I knew they were one and the same. It took me over a year to realize that my positioning was all off.

I had to create more relevant call-to-actions and lead people toward becoming the right customers for Planscope. I had to get them to where I was.

With my agency, we had to host seminars to show case studies and examples of how redesigning your website could lead to more sales before the value of what we were offering started to click. The business owners who sat through our seminars started to see us as an authority in creating websites that increase sales and revenue.

It was exactly the same lesson I learned when running my web agency. We couldn’t just cold approach business owners and say, “We build websites! Hire us!” That rarely worked. It was a lesson so subtle that I had to learn it twice.

The same soon became true with those who ended up on the Planscope blog. I couldn’t invite them to the same room, but I could do the next best thing. I created the digital equivalent: an email course that showed people why client projects go wrong, and what to do about it. The course sent a series of five emails, sent one day at a time. Throughout the course, I gave people a recipe for managing their clients better, and at the end introduced Planscope as a done-for-you tool to help make that better.

Lesson learned: Meet people at where they are now, and lead them to where you need them to be to become a customer. And realize that what you’re selling isn’t always what people are buying.

I started hearing from customers that they wanted to hear more than just the random article about how I grew my agency. One recurring theme was pricing: How can I value-price my work?

Around that time, I learned that people weren’t looking for project management software. They just wanted better clients, which was terrible for my Planscope business because we made project management software.

Even though I thought this didn’t really fit within the scope of a business that sold project management software, I decided to write a short ebook that was titled Double Your Freelancing Rate. It was an attempt to meet people where they were and maybe make some extra leads for Planscope. It worked. Too well, actually.

People bought. And I created more content, products, and courses — all about finding better clients. More customers and subscribers started showing up, most of them not knowing that I even ran a software company. The content marketing for my company was more successful than the company. This side project was born from an observation from my main job was becoming its own animal.

So I decided to sell Planscope and go all-in on the new training business I named after my book by removing “rate.” Thus Double Your Freelancing became the company that published the Double Your Freelancing Rate eBook, and eventually, made the Double Your Freelancing Rate course (and hopefully more products to come!).

The remainder of this guide is about how I implemented the lessons learned from growing my agency and software business to largely automate sales in my current business.

Build the Business You Want to Build

I learned a lesson from the stressful nature of running a web agency: If you’re going through the trouble of building a business, make it one that helps you live the life you want to live.

That’s why, unlike my agency with its $100,000-plus monthly payroll or my software product that had me scrambling to figure out ways to turn $24/month subscriptions into actual profit, I had a few ground rules for how I’d keep this new business based around Double Your Freelancing Rate afloat:

  • It had to be minimal. I didn’t want to deal with another staff I had to manage. I wanted low overhead.
  • It had to be automated. I was ready to cash-in on some much needed R&R. I didn’t want to do any big launches or stuff that stressed me out. I needed fully automated launches that ran independently and were only promoted to those who were ready to buy.
  • It needed to be reliable. I wanted to write free content, pay for ads, get people in front of this automated system, and then let everything else down-funnel just work.

I soon created a full-fledged course around the book. So now it was time to create an email course to attract more buyers. That was what my El Dorado had to look like, my mythical city of gold.

Now let’s look at how I found it:

Version 1.0: The Email Course

If you want to sell a product online, you need to create trust between the prospective buyer and you.

To create this trust, many businesses — especially training businesses — employ education-based marketing. They give away a lot of content for free, and in this content they demonstrate their ability to deliver value. The businesses know that if they can get someone to say, “I’ve learned a lot from this business, and they’ve already made my life much better,” that person is much more likely to buy from them.

The simplest way to do this is to start a newsletter. Create free content, and at the end of each piece of content (or as a pop-up, or in the sidebar, …) add an opt-in form that says, “Join our newsletter!”

As people join, you’re then on the hook for sending out broadcast newsletters to your subscribers. Typically these newsletters will include new content, promotions, or product announcements.

The idea is that if someone becomes a regular reader (or listener) of your content, when you create and sell a product there will be sufficient trust to get them to buy.

But joining a newsletter isn’t very compelling. After all, who wants to get even more email?

So more advanced marketers will create lead magnets or “carrots,” like reports, checklists, or white papers, that offer something for free immediately. Once downloaded, the reader is then added to the newsletter and starts getting new content, promotion, and product announcements.

And then there are email courses, a special kind of lead magnet that are daily lessons delivered over email, as opposed to downloaded immediately.

Based on my principles of being automated, minimal, and reliable, I chose to create an email course that I could offer throughout my website. Drawing on my experience having created an email course for Planscope, this email course would promote my ebook-turned-paid-course Double Your Freelancing Rate, which was quickly becoming my best-selling product.

One reason I decided to create an email course was because I knew that just sending random email newsletters would violate my automation principle: I didn’t want to be on a hamster wheel, needing to churn out content continuously in order to keep the business afloat.

The other was that I wanted to prepare people to buy Double Your Freelancing Rate.

Let’s imagine that you’re going to start promoting a new product to your list tomorrow. Everyone is going to be on the receiving end of that promotion, no matter if they joined your list last year or yesterday.

Those who joined a year ago are probably sufficiently conditioned to buy. They trust you (otherwise they would have unsubscribed), they know what you think about whatever it is you teach on, and know you’re capable of delivering value.

Someone who joined your list yesterday? Not so much.

So if I could create a free email course that creates trust over time by teaching somebody the ins-and-outs of pricing theory (and why most freelancers are clueless when it comes to pricing), they’d be much more likely to buy my paid course.

There are two schools of thought around how to sell online courses or ebooks using educational email courses:

  1. Go deep. Find one subject you teach in the course, and cover it exhaustively. This will demonstrate the quality of the content you teach, and leave people wanting to learn from the full program.
  2. Go broad. Give people a basic overview of what you teach and have them finish your email course equipped to achieve the outcome your course promises on their own. But then present your course as the shortcut that gets them to the end goal (launching their first product, raising their prices, and so on) as quickly and effortlessly as possible.

I went with the latter option.

Technically, setting up the first version of the email course was relatively straightforward:

  • Sign up for email marketing software that supports dripping out content over time. I use Drip.
  • Create a campaign that includes a series of emails, spaced a day (or more) apart.
  • Set up a form and tie it to that campaign so new leads automatically get the course.
  • Create the landing page and call-to-actions that get people to opt-in to the form.

My email course was titled Charge What You’re Worth, and I genuinely wanted people who went through the course to be able to understand why they’re undercharging and how they can charge more.

My email course was called Charge What You're Worth

I also didn’t want to cannibalize my paid course, so I presented my paid course as having the specific framework that they could follow to reliably charge more. It included recorded case studies, contract and proposal templates, and scripts they could follow.

The free course covered the high-level theory; the paid gave specifics.

Could people use just the free course? Absolutely. And many do. But it would be like offering someone just a map to the treasure. Why take just the map when you can get all the tools you need, along with an experienced miner to show you the way? I was okay giving some away to attract the people who really wanted the deeper, fun stuff.

I also had to make sure the course content met people at where they are now. This means that I had to target self-identified freelancers (even though my eventual not-so-subtle goal was to get them to start looking at themselves as consultants).

It also required me to first break down a few walls before I could erect a better mental model of how they should look at the value they provide their clients.

Here’s the lesson plan I came up with for Charge What You’re Worth:

  • Lesson 1: Why there’s no such thing as a “market rate.”
  • Lesson 2: The real reason most freelancers are underpaid.
  • Lesson 3: How to avoid being seen as a cheap commodity.
  • Lesson 4: What are your clients really looking for?
  • Lesson 5: How to use Socratic questioning to figure out what your client needs.
  • Lesson 6: How to quantify the value you bring to your clients.
  • Lesson 7: Why anchoring your proposals can double your closing rates.
  • Lesson 8: How to tie it all together with a killer proposal.
  • Lesson 9: How to double your rate without scaring off your clients.

I started the course by thinking about where somebody joining is right now. They’re a freelancer who’s struggling to get paid what they’re worth. They likely did what most do: they quit their job, found a first client, and scrambled to figure out what the “market rate” is of whatever it is they do.

The course started by smashing the idea that there’s such a thing as a market rate. It then leads the subscriber into thinking about why their clients hire them — why is someone willing to pay for something like a new website?

In the third lesson, before I’ve actually taught any tactics or strategies, I posit what life could be like. I teach the subscriber about why they don’t need to race-to-the-bottom. I show them that there’s a better alternative.

Before creating this course, I asked a lot of my paid customers what brought them to buy my course. I learned that most of my customers ended up going down this same path on their own. They saw that others were charging a premium and they saw that it wasn’t because they were any better technically than they were. Independently, they all realized that by positioning themselves as a commoditized developer, designer, writer, etc. that they were setting themselves up to be paid a commodity rate.

And then they came across my course and they bought.

So I had to proactively think about how I could lead somebody to that same realization. Before I could teach somebody a better way, I had to get them to realize that they were on the wrong path.

Once I get the subscriber to understand that it doesn’t need to be the way it is now (this culminates in lesson four), I then show them what to do about it. I launch into a series of hard-hitting micro lessons that focus on a few of the big tactics I cover in the paid course: how to learn about the problem behind a project, how to quantify the value of a project, and how to pitch the client.

What I don’t do is share all the actual questions you should ask your clients, the exact process I use for quantifying valuations, the proposal template I recommend that incorporates everything the course conceptually teaches, and more.

I leave that for the paid course, and every student of the email course knows that.

In the first version of this email course, a few days after the ninth lesson was delivered I jumped into a soft pitch for the paid course.

“Hey, if you’d like to go further, I have this for you.”

It worked. It just didn’t work as well as I needed it to.

I’d occasionally reach out to those who had gone through the course and ask people why they didn’t buy. The most common response was, “I will. It looks great. But I’m busy.” The theory was resonating, but not enough to get people to take action. (And we all know what happens when people tell themselves, “This looks great, but I’m busy and will come back to it later.” They rarely do.)

I realized I needed something that was a little more urgent. The send educational emails, pitch product does a good enough job at introducing a product and drumming up some sales, but I wasn’t getting launch-style results.

I needed urgency. I needed to get people to better engage with the course.

Result: Sales were weak, but people really liked the course. Only about 0.5% of people who joined the email course ended up converting. The average value of a customer is $377, so each new subscriber was valued at around $1.89. Not quite the 20x acquisition costs.

Version 2.0: The Personalized Pitch, The Bridge, and Interactivity

I wasn’t very happy with how well the first version of the course was doing. It was converting, but it wasn’t converting well. The issue, I soon realized, was that my pitch was weak. I was casually mentioning my paid course, and didn’t have any actual reason in place for anyone to buy now. I was being a bit too timid about it all.

I didn’t scrap it. Instead, I painstakingly tested ideas and iterated quickly. Here’s what I added to the course, which I’ll now describe in more detail:

  • A personalized, fully automated pitch that puts up the course for sale every Monday and closes the promotion the following Thursday.
  • A “bridge” sequence that logically connects the email course with the paid product.
  • Interactive worksheets that better engage subscribers and allow them to advance through the lessons at their own pace.

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The Personalized Pitch

I’ve done plenty of launches, and they’ve all done well at generating a lot of sales at once.

That’s because launches almost always include some sort of urgency, and there are three tactics you can use to create urgency:

  1. Limited quantity or availability. Businesses that launch the same course a few times a year use this urgency tactic to drive sales.
  2. Discounts. A limited time coupon that delivers the product at a discount (Think: Black Friday sales).
  3. Bundling. Rather than discounting, you can offer extras.

Enough sales of the paid course come in outside of the email course, so I didn’t want to make it only available after going through the free email course (so I couldn’t use Tactic #1). And I didn’t really have something compelling that I could bundle in with the paid course (Tactic #3).

So I decided to discount.

But this led to a problem: When you usually create a discount code, you might set it up in your e-commerce software, email the discount code to your entire list, and then set it to deactivate after a certain date. But how could I do the same with a fully automated email course that needs to chug along without my continued involvement? Remember: One of my business principles was automation.

People could join the email course at any time. This meant that if I had a four-day discount window, someone would always be eligible for a discount, thus not resulting in scarcity.

How could I automate this? How could I use a drip email sequence to generate coupon codes, drive people to a sales page, and show countdown timers and all the other bells-and-whistles that get people to buy?

My email marketing tool of choice, Drip, allows for storing custom information against my subscribers. And I could write this information as a part of the launch sequence — and they use a templating language called Liquid that lets me run some pretty complex operations:

The code I use to set up my email course operations.

The above step runs every Monday at 10 a.m. local time for those who have gone through the email course. Since it’s always run at the same time, I could tell it to advance to next Friday at midnight (which is close enough to Thursday 11:59 p.m.) and store that timestamp in the subscriber’s profile.


This allowed me to create individualized emails and sales pages for every subscriber of my email course:

Offer to sell paid course
Email course participants see a countdown clock.

No matter if you’re in New York City or Jakarta, the discount window I offer on my paid course opens at 10 a.m. the Monday after you complete the email course and expires Thursday at 11:59pm.

And this happens every week, entirely on autopilot.

The emails I included in this sequence are the same structure that you’d find in any sort of list-wide launch:

  1. Announcing the sale
  2. Present a bonus
  3. Overcome self-limiting beliefs
  4. Sale ends tonight and F.A.Q.
  5. Sale ends in 4 hours

Since the product price is only $297 (or $207 when bought during the launch sequence), I don’t really need to have a super-long launch sequence. More premium products would want to open up the cart for longer and send out more emails.

And because the email course subscriber’s information is synced with the paid product’s sales page, I’m able to automatically disable the coupon and visually remove everything promoting it (the countdown timer, discount language, etc.) when the subscriber’s pitch window expires.

What this means is that if my email course discount window ended yesterday, if I viewed the premium product’s sales page it would show the full retail price. But if you view the same page at the same time and you’re currently going through the pitch, you’ll see discounted pricing and a countdown timer personalized to you.

The Bridge

Another common theme from those Version 1.0 customers I surveyed is that I was presenting my paid course without any warning and then expecting them to buy.

So I decided to have a gap between the lessons and the pitch. And during this gap, I’d summarize what they learned (and give them a downloadable checklist) and help them overcome any self-doubts that they might have about actually implementing what I teach. So the email structure became:

  1. The nine-lesson email course
  2. Two-email “bridge” sequence
  3. Six-email “pitch” sequence

The not-so-secret goal of the bridge was to let them know that I’d be opening up a launch window the following Monday and to ease them into the sale in a less jarring way.

I sent two emails, one on Tuesday and the other on Thursday:

Preparing the subscriber to buy.


Tuesday’s email
The last email before offering the paid course.


Thursday’s email

As you can see, I’m preparing the subscriber to buy.

Rather than doing what I was doing before, and what I’ve seen people do in the past, I’m not just going straight from the lessons to surprise announcing a product.

The first bridge sequence I added was relatively unsophisticated: just two emails queued up to go out the Tuesday and Thursday after wrapping up the lessons.

Interactive Worksheets

I also wanted to make the email course more engaging.

One of the best improvements I made to my paid course was to add more interaction. Rather than just asking people to go through and learn, I encouraged them to act. And I created interactive worksheets that allowed them to apply what I was teaching to their unique business.

So I took this concept and applied it to the email course. Instead of just sending out text-heavy lessons, I included a worksheet link at the end of each email. I knew that if I could get the subscriber to actually apply the content I was sending them, they were more likely to be successful.

And if they’re more successful as a result of going through my free email course? They’re more likely to buy the premium course.

I went through each lesson in the course and asked myself, “How can I get someone to do something with this?”

It’s easy to read. It’s easy to learn. It’s easy to get inspired. But acting? Actually doing something? That’s the hard part. But it’s our job as teachers to do everything in our power to help our students take action.

What I came up with were eight simple worksheets that accompanied the first eight lessons. Each worksheet takes just a few minutes to complete, and after submitting a worksheet the student gets a copy… and I get a copy. (Don’t worry: I make it clear that I also send myself a copy of each worksheet. This encourages students to reach out for help within a worksheet answer, and I make it clear that either myself or someone from my team combs through the responses and reaches out when we can.)

Over the last two years, I’ve collected over 12,000 worksheet submissions:

Worksheets from the paid email course.

What I’ve learned from these responses has helped me create a stronger, more successful email course. It’s instant feedback, valuable customer research data, and is a useful exercise in their learning process. Win-win.

For example, in the first worksheet, I ask people what they’re hoping to get out of this course. This has helped me ensure that what I’m selling (for free) on the course opt-in page matches what they’re getting. I’ve been able to slowly align expectation with reality.

The last worksheet includes a text area where the subscriber can include a mini-testimonial about what they’ve learned in the course and their next steps, along with whether or not they still have any questions about what I taught.

These answers are all qualitative. They’re free-form text, which means acting on this data requires me to look over hundreds of submissions a week and try to normalize out any common themes.

But I also included quantitative questions, like dropdowns and checkboxes, that allow me to collect demographic data (like how long they’ve been freelancing or what they typically charge now). This information gets stored on their subscriber record and I’m able to run reports on it.

For example, here’s a report (using current funnel data) showing the average revenue per subscriber of someone who joins the email course and tells me what kind of work they do (this is a newer question, so I don’t have as much data as I’d like on this yet):

Average revenue per user for my email course.

I also decided to try making it so that as soon as you fill out a worksheet, you’re sent the next lesson immediately while you’re engaged. And if you don’t fill out a worksheet, the system will wait a day and then send the next lesson.

So it’s a bit like a hybrid drip and at-your-own-pace email sequence. Some subscribers go through the entire course in one sitting. Others might get the lessons dripped out a day at a time.

Fortunately, Drip makes this simple to set up:The user flow for my email course.

This improvement has resulted in a lot of positive feedback from subscribers. If someone’s highly engaged with what you’re teaching — why hold them back from moving through the course? And if they’re not as engaged, dripping out lessons on a daily basis is a good way to keep yourself front-and-center in their inbox.

But I wasn’t done with improving my course.

I decided to make my most ambitious change yet to the email course and make it highly personal.

Result: We were getting there! About 6.2% of subscribers were now ultimately buying, or about 10x more than in the first version. Value per subscriber spiked from $1.89 to $23.37.

Version 3.0: Personalization and Scoring

I wasn’t done yet. The geek in me wanted to see how much further I could optimize the funnel. To be completely honest with you, I was on Cloud Nine: “I get $23.37 every time someone fills out this form? WOW!”

In the third (and current) version of the sequence, I decided to try to make the email course hyper-personalized to the subscriber:

  • I’d personalize the content of the course and the sales page depending on who’s going through it. I’d use answers to the questions I ask within the worksheets and at the point of opt-in to tailor the messaging to be specific to the subscriber. For example, if you’re a web designer, all the examples I include in the email course and the language I use to describe your business is specific to web designers.
  • I’d score people’s engagement in the course and alter the bridge sequence to be shorter for those who were highly engaged and longer for those who weren’t very engaged. Again: give engaged customers what they want.


Everyone wants products built specifically for them. That’s why niching does so well. Without any need for testing, I know an email course on pricing for web designers would work better for web designers than a general course on pricing.

Since I’m already using my opt-in forms, on-site survey widgets, and backend progressive profiling code for collecting information about who someone is, what they need out of the course, how long they’ve been consulting, whether they’re solo or work with a team… why can’t I incorporate all of that into my messaging?

Drop down asking for field.
The sign up drop down asking for field.

Here’s what I ended up doing:

  • Variable phrases: Any instance of “freelancer” would be replaced with the relevant title in both the emails I send and on the sales page. For example, a design agency owner would see “design agencies” and a solo developer would see “freelance developer.”
  • Variable examples: When I use examples in my lessons, they’d be specific to the type of work someone did. A writer would see me use an example about a copy project for a client; a marketer might see an example for a paid acquisition project.
  • Variable case studies: During the bridge, I reference success stories of people who have gone through my content and benefited from it. You’ll now see examples from people like you.
  • Variable positioning: When I introduce the paid course, I look at what you told me about why you need this course (Are you starting out and need general pricing advice? Are you experienced but want to learn how to value-price? Are you struggling to close your proposals?), and using that data I position the paid course against that need.
  • Variable everything: The sales page’s headline, copy, testimonials, and offering are personalized based off of what you’ve told me, either explicitly or behaviorally.

This ended up requiring a lot of custom code, and I’ve ended up receiving a lot of interest in helping make website personalization more accessible. I’m working on a new software product that does exactly this. If you’d like to follow along, you can join our early access list.

Tweet, customers are worth $41.82 after personalization.

Then, I ran the numbers.

I looked at people who had submitted enough data to trigger personalizations (specifically, the type of business they ran) and who have viewed the sales page for my paid course. I compared their average revenue per subscriber against revenue pre-personalization.

Almost across the board, the sales increased at least 50% — just by tweaking some copy. And course engagement scores went up, with about 20% more people finishing the course than before.

Collecting this data has also given me a superpower: I know the value of key demographics who move through this funnel.

When filtered by job listing, some email course subscribers are worth even more.

Notice: all of these are higher than the $23.37 from version 2.

A developer who enters this funnel is valued at $62.48, but a designer is worth just $36.45. Marketers are worth $66.43, and writers are $40.02. The non-developer numbers used to be horrendously low (I’m a developer myself, so a lot of my early examples and terminology appealed to developers), but personalization has helped me increase valuation across the board.

Here’s my superpower:

  • I can now explicitly target high-value demographics, like developers.
  • I can focus on increasing the subscriber valuation of low-value demographics, like designers.

Because I have this information and can track it over time, I can definitively see how the work I’m doing personalizing directly affects subscriber valuation. No more “well, I hope this works!” and no more random tactics. And the metric I care the most about is the average value of subscriber (which is just the total number of subscribers divided by the revenue generated).

Now I know that if I can get developers through the funnel for under $62.48, I’ll be profitable. Many businesses throw money at acquisition but think they’re paying too much or aren’t sure if it’s working or not. When you can track the performance of a funnel like this and actively market it (on channels like Facebook), you can confidently invest in paid acquisition.

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Intent Scoring

I was also struggling to figure out how to not be as sales-y to those who weren’t ready to buy.

I had the bridge, but that just gave a week of buffer time prior to opening up the pitch sequence. The conversations I’ve had with non-buyers were showing that the second biggest objection to buying (next to “I don’t have the time”) was that they just didn’t trust me enough yet.

The solution was to take the evergreen newsletter sequence I’d set up, a six-month long weekly drip of content that includes personalized call-to-actions and P.S. blocks, and push it to unengaged subscribers. Once they’ve read a handful of articles, I’d then take them out of that sequence, put them in the pitch sequence, and then put them back into the evergreen newsletter.

The complete funnel.

To do this, I had to figure out how to lead score subscribers. Lead scoring is important because not every lead is created equal. A subscriber who isn’t engaged and isn’t filling out any worksheets is unlikely to buy, while a highly engaged subscriber who is reading all of my emails and completing the worksheets is a prime candidate to take what they’re learning to the next level.

The most straightforward way to do this has been to just give them a point for each worksheet they fill out. Since there is a total of eight worksheets, each subscriber can get up to eight points.

If they fill out six or more worksheets, I push them into the old two-email bridge sequence and then they move directly into the pitch. They were ready and engaged.

If they fill out between three and five worksheets, I push them into the evergreen newsletter sequence and wait for them to read two articles. This means that there’s a minimum of two weeks of emails that will go out before they’re then eligible for the pitch. That group needed a little more love.

And if they’ve filled out less than three worksheets, I’m looking to have them read four articles first. Again, this means that they’re not going to be pitched for at least a month.

While this extends how long it takes to potentially capture revenue from a subscriber, it allows me to really wait until someone is fully ready to buy before pitching them. And again, this happens automatically.

Early results are extremely promising so far, but I don’t have enough statistical data to be conclusive.

This Email Course is One of my Most Valuable Assets

I treat this email course, Charge What You’re Worth, like a first-class product, like something that a customer pays thousands of dollars for.

It’s something I’m able to track: I pipe everything people do within this sequence into tools like Mixpanel, and I can break success down by any data point I want — where someone came from (e.g. a Facebook ad), what type of business they run, the lead score I assign to them, and more.

I also have built-in feedback loops, namely through the worksheets I offer, that help me make sure that I’m on point and addressing the goals new subscribers have. If I messed up somewhere along the process, I can quickly remedy the problem.

At the end of the day, I know exactly what someone entering my funnel is worth.

This makes running ads, approaching partners for joint ventures, and more super simple. I know exactly what I’m willing to pay to get a new lead into the funnel, and I can associate lead values with individual ad campaigns, business types, the blog post they initially found me on, and so on. I use Mixpanel, and I have it synced with all of the data I store about each subscriber in Drip. With just a few clicks, I can run reports on just about anything. (Development agency owners who have completed my email course? $419.12 per subscriber. Subscribers who first showed up from my friend Bryan’s website and identify as a marketer? $90.64.)

Having a marketable funnel is probably the most valuable thing you can do for your business right now. It allows you to create trust, deliver value, and sell your products when it’s right for your subscriber. It’s reliable, 100% automatic, and scales indefinitely.

Your Turn: Creating a Highly Effective Email Course of your Own

In overviewing the evolution of my email course, I’ve covered a lot.

You’ve seen how I’ve gone from a more traditional drip email sequence to a highly personalized and fluid sales sequence.

While I don’t expect you to build anything this advanced immediately, there are a few bare minimums that I think you should take away from this guide:

#1: Start at the End

What is the purpose of this course? What will it be selling? How can this course complement, rather than cannibalize, what you’re ultimately going to pitch? And most importantly, how will getting something like this in place positively impact your business and your life? Be brutally honest with what you’re after.

#2: How Will it Prepare People to Become Customers?

We don’t usually think about what leads someone down the path to becoming a customer.

Like I learned when running Planscope, people didn’t know they had a project management problem. How can you meet people where they are now and lead them to realizing the need for a product or service like yours?

#3: How Can You Measure Success?

What can you incorporate into the course that will help you really guarantee that your students are benefiting from it? How can you passively learn about their needs and goals, and use that data to strengthen your sequence? (And maybe even personalize the content based on what someone’s telling you.)

#4: Present Your Product as the Shortcut

A great email course is going to leave someone with two options:

  • The long road. They now know the direction they should be moving in, but they aren’t quite sure exactly how to get there. To figure out their way, they’ll need to go through a lot of trial-and-error and will likely scrape their knees a few times in the process.
  • The shortcut. This is your product. The quickest and surest path to the goal your course describes.

#5: Start Small

I encourage you not to think you need to do everything I’m doing in order to be successful. All of my customizations may feel overwhelming but it was the result of one tiny step at a time over the span of two years.

My first email course wasn’t very sophisticated, but it worked. It provided me a starting point.

Over time, I’ve made the course more sophisticated and more profitable. Over the last year, this email course alone generated $138,205.20 in revenue. And that’s just initial revenue. Many of these subscribers end up buying other products of mine and 10x their value over time…completely on autopilot.

And each week, this email course generates a few thousand in additional revenue.

New subscribers in, money out. It’s a fly-wheel that’s becoming more valuable with each new experiment I run. It’s my El Dorado.

But a “low-tech,” straightforward course that preps people to become your customers is much better than nothing, and can be improved upon over time.

Want to check out the email course I’ve described in this guide? Here it is.

And if you’re interested in doing any of the sort of advanced automation or personalization work I’ve done, I’ve (of course) created a course on this.

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