I recently completed an intensive 10-week accelerator for online courses called Email Boss. 

The program was one of the greatest educational experiences I’ve ever had. I learned more about online marketing and persuasive psychology in 10 weeks than in the previous 6 years of trial and error in online marketing combined.

In this article, I want to share the most valuable lessons I learned. I hope to save other content and course creators some of the pain and frustration I’ve experienced trying to figure it all out by myself. 

I believe the knowledge of how to sell online courses is THE linchpin in making online education effective, profitable, and impactful. There are so many people in the world with priceless knowledge to share, and many of them write blog posts, record videos, or even publish courses. But just because you build it, doesn’t mean they will come. There is an entire industry dedicated to selling information products online. We need to start by learning the best of what has come before us.

The program is called Email Boss, and is taught by online course marketing expert Billy Broas. It is open only to established course creators, and delivered live to small cohorts that meet twice per week.

I found out about Billy from a blog post featured by the online course platform I use, Teachable. His company Linchpin Media is the only “Teachable Expert” recommended for sales and marketing consulting. Billy has an extensive 10-year track record of selling his own courses and working with clients in over 30 niches to sell theirs.

Here is what I learned in Email Boss.

The pitfalls of “hard teaching”

The first thing I discovered, like a splash of cold water in the face, is that I’ve spent years doing what Billy calls “hard teaching.”

By analogy to “hard selling,” hard teaching is the classic mistake made by content creators. They find early success making and selling things online, and so they double down. They create more and more tutorials, walkthroughs, templates, videos, blog posts, and ebooks. They give it all away for free, hoping and praying that if they give away enough, then people will purchase their paid course.

How is this similar to hard selling? Because it doesn’t actually solve their prospects’ problems. 

Your readers ask for simpler, easier solutions, and you give them yet another 2-hour tutorial to watch. They ask for a step-by-step approach they can implement today, and you give them yet another 5,000-word blog post to read. 

This “content” isn’t the solution they need – your course is! They need the structure and accountability that come with joining a program with a clear beginning, middle, and end. When you send them another round of “free stuff,” that just puts more barriers in front of them. Of course they’re going to want to consume this free stuff before moving on to the paid stuff. But the free stuff never ends!

The power of parable-based marketing

In contrast, we learned a very different approach to marketing, called “Parable-based marketing.” It draws on the marketing strategy of the best-selling information product of all time – the Bible. 

The Bible doesn’t provide a lot of instructions and checklists to follow. It teaches through stories. The stories are simple and immediately engaging, connecting the reader to universal aspects of the human experience. Each parable packages up a small insight or “aha” moment, giving the listener both entertainment and a useful life lesson.

This is the same approach taught in the Email Boss program: email your subscribers very frequently with small stories that each deliver a morsel of insight or small shift in perspective. But these emails don’t deliver more to do’s or sales pitches to people’s inboxes. They give them a lightbulb moment in their day, slowly reinforcing your reputation as a source of wisdom on this topic.

Taking an email-centric approach

Email is the central focus of the program, for many reasons:

  • It is the only form of online communication that delivers a message straight to a person’s private inbox
  • It is one-to-many, yet allows for a personal connection, like a letter
  • People have to opt in to your email list, which means they are already predisposed to your message
  • You can easily track detailed analytics for how often they open emails and click links
  • With the press of a button, they can send a direct response telling you what they want and what they don’t

The single most important metric in our course business, Billy told us, is revenue-per-email-subscriber. Email subscriptions are the most meaningful metric that shows that someone wants to hear from us, and revenue is what keeps the lights on. So connecting the two metrics yields a powerful overall picture of the business in one number.

Why is it so important to email them frequently?

We returned again and again to the adage that “80% of success is just showing up.” Instead of only emailing unsuspecting subscribers every few months when YOU have a promotion or need a sale, you remain a constant, trusted presence in their lives. When they decide to take action in this area, who is the first person they will think of? You.

Toward the end of each email, after you’ve delivered a little “knowledge bomb” that makes them happy to have opened it, you mention your product. You “back in” to the product from the story you’ve just told, presenting it as a natural next step for anyone who wants more. This is how you can sell without selling, pitch without pitching. Subscribers will actually be happy to hear what you have to offer.

There’s another benefit of frequent email-centric marketing: you can test different ways of positioning the product. Every argument, benefit, or framing appeals to different kinds of people. Accountants might be attracted by the predictability and structure of your course, while artists might like the opportunity to explore different approaches (these are stereotypes but you get the idea). 

Depending on the audience and venue, you might want to use different messaging and positioning. Emails give you the chance to test them in a cheap, frictionless, low-risk way. Billy told us that, most of the time, there is one positioning angle that blows the others out of the water. Finding and doubling down on it is what makes your business explode. 

Email-centric marketing strikes to the very heart of what is most important to content and course creators: quality of life. We started these businesses to have more freedom and self-expression in our work and lives. And yet constantly cranking out hard-core, massive videos and essays can leave us feeling drained and exhausted. 

Instead, email-centric marketing has us telling brief stories, communicating directly with our audience, reusing and recycling existing content, and refining our core messaging. All this while leaving the frustrations and anxiety of social media by the wayside. 

Relationships are everything

Underlying the marketing tactics and strategies, Email Boss advocated for a fundamental relationship with the customer as the very cornerstone of our business.

Instead of immediately going for the sale every time, we should cultivate a long-term relationship with the people who generously subscribe. Instead of constantly launching and pitching new promotions, we educate them so that they are set up for success on day one of the course. Instead of viewing the transaction as the end-all, be-all, we nurture a community that actually cares about us and each other.

Billy shared with us the analogy of golf balls on a golfing range. Each prospect is like a golf ball slowly making its way down the fairway with each swing. A few go from beginning to end in one miraculous hole-in-one. But that is rare. 

For most prospects, it takes multiple “touches” before they are informed and ready to make a purchase (sometimes referred to as the Rule of 7). There is a real limit to how much you can speed up that process. And every time you launch a new product or promotion, all the golf balls go back to the beginning. This is the vicious cycle that so many course creators find themselves trapped in. 

We learned a number of other strategies for helping prospects through the stages they naturally go through in their journey. For example:

  • Trusted Advisor: positioning yourself as a trusted advisor in their decision-making process
  • Infotainment: teaching and entertaining at the same time as you are selling
  • Superhero Character: creating a heightened version of your true self that they can look to as a role model
  • Mentor Story: telling the story of how you had a mentor to get where you are, and that therefore they should have a mentor, which is you
  • Signature System: a proprietary name or term that sets your system apart from generic ones

But all these tactics rest on the foundation of a trusted relationship between you and your subscribers. Tactics don’t work on uninformed buyers. They only work when they already know about and value what you’re offering. It is 7–10 times easier to convert an existing customer versus a new one. Which means you should invest in a long-term relationship with every person who signs up to your list.

Discovering the Chain of Beliefs

This concept was one of the most powerful things I learned in Email Boss. It is at the very heart of the education and relationship that matters most when it comes to people trusting you with their learning.

The “Chain of Beliefs” refers to the beliefs that a prospect needs to believe, realize, and agree to in advance before they can accept the product being sold. Without these beliefs in place, nothing you offer in terms of features, benefits, bonuses, or special deals is going to have an impact. But if these beliefs are in place, then purchasing your course will be the obvious and natural decision for them to make.

Here is an example of just a small selection of beliefs that are in the “chain” for my Building a Second Brain course:

  • Your brain is for having ideas, not holding them
  • You are already creative and do creative work
  • Your thoughts and ideas are valuable and worth saving and revisiting
  • You are already doing most of the work required
  • You can get and stay organized quickly and easily
  • If you don’t make an intentional effort to preserve your thinking, it will be lost

Do you see how each of these beliefs is absolutely necessary for someone to even consider buying my course? They can believe the course is the best thing in the world, but if they don’t believe that “My brain is for having ideas, not holding them,” then what I’m offering won’t make sense. They can think having a Second Brain is the niftiest idea they’ve ever heard, but it will remain only a “nice to have” unless they believe that “If I don’t make an intentional effort to preserve my thinking, it will be lost.”

These beliefs can be quite mundane. For example, “I have the time and energy to benefit from this course.” They might be the perfect customer in every sense, but if they believe they don’t have the time, then you’re not going to make the sale. Luckily, these beliefs can be systematically cultivated in your audience. And finally we arrive at an answer to the question, “What kind of free content should I create?” The answer: content that supports the Chain of Beliefs. 

For example, if you want them to believe that “I have the time and energy to benefit from this course,” publish a blog post with a recommended schedule showing how little time is necessary to successfully complete the course. If you want them to believe that “People like me can benefit from this course,” publish a few case studies with different kinds of people and how they’ve benefitted. For my course, if I want them to believe that “I am already doing most of the work required to build a Second Brain,” I can create content with statistics on how much time people already spend reading, listening, and watching media on their devices.

What you are actually doing with your Chain of Beliefs content is pre-educating your customer. Ask yourself, “What do they need to learn, do, prepare, think about, or have ready before benefitting from my course?” Which “early wins” can you produce for them right now, so that they show up on Day 1 of your course eager to learn more? 

The Chain of Beliefs is actually infinite – there is no limit to how many beliefs can disqualify someone from considering your course. This means that you have to be like a detective, constantly listening for and investigating new beliefs that you can add to your list, and begin influencing via your emails. Every time you find and add in a new supporting belief, it will show up in your results.

Crossing the Bridge of Transformation

I had heard many times the online course mantra of “People aren’t buying your course – they are buying a personal transformation.” I knew intellectually that you have to take students on a complete journey where they change not just what they do, but who they are.

But learning about the Bridge of Transformation in this program gave me a much deeper understanding of how critical this journey is. And that it doesn’t happen by accident. It takes a concerted effort that starts with marketing and goes all the way through to the end of the course and beyond.

Let’s start with the “Before” side of the Bridge. We spent a lot of time “diagnosing” the current problems of our customers. What do they worry about? What do they fear? What do they want? What pains do they feel? I had always shied away from talking about these things too directly, because I didn’t want people to think I was exaggerating their pain in order to make my solution look more attractive.

But Billy told me something that served as a wake up call: unless you can accurately describe the problem people are facing, they won’t trust you to provide the solution. It makes perfect sense. Would you trust a tennis coach who couldn’t seem to understand why your backhand was so challenging? Would you trust a doctor who couldn’t seem to come up with a proper diagnosis?

We were taught to pinpoint specific symptoms that people clearly experience, rather than abstract problems that may or may not be the cause and that they might not even know about. For example, instead of “Everything is disorganized” (which may or may not be true), we want to point to “Piles of paper everywhere.” We want to highlight recurring questions, familiar frustrations, basic emotions, and internal dialogues that they will feel at a visceral level. 

For example:

  • Late for an appointment again?
  • Wife mad at you again?
  • Slamming or throwing the keyboard
  • Another check bounced?
  • Are your employees applying for a job at your competitor?
  • Tons of clicks, but no sales?
  • Writer’s block staring at a blank page
  • Did she never call you back?

Decision-making is inherently emotional. If they feel nothing in response to the course you are offering, they might not consciously reject it, but they also won’t feel moved to take action and purchase.

On the other end of the Bridge, we create “possibility content” that shows what life will be like after they cross it. What will they be able to have, feel, do, and be after completing your course? What will be possible? What will be within reach? What will their daily experience of life be like?

The gap between those Before and After states is the promise of your course. That is the chasm you will help them cross. What they are willing to invest in your course depends on how quickly, reliably, painlessly, and easily you can help them cross it.

The secret weapon of sales letters

Most of the above lessons have to do with understanding the basic psychology of your customer. It takes real work and testing. And there is no substitute for that process.

Once you have a good understanding of that psychology, and an ongoing, trusted relationship with your email list, you’re ready to generate sales. But how do you actually make your pitch and close the sale? You follow a time-honored tradition among marketers, going all the way back to telephone and direct mail marketing: the sales letter.

The modern incarnation of the sales letter is the “sales page” – a dedicated webpage that presents your course and persuades people to purchase it. We learned that most course creators make the mistake of having this page do everything – educate the customer, collect an email address, and make the sale. This usually leads to multiple, conflicting objectives that all interfere with each other. 

Instead, the sales letter has just one purpose: turn a visitor into a customer. Every aspect of the page has to serve this purpose: just enough education without creating an obstacle, no links to outside sites, no distracting graphics or videos, headings that pull people into reading each section, proof for every claim, strong arguments that defeat objections, and ultimately, an inexorable pull toward that giant “Buy” button.

The sales letter is the linchpin of your sales funnel – the series of stages through which a new visitor moves on their journey to becoming a customer:

It isn’t designed primarily to convert cold traffic (people who have never heard of you) into customers – that is the job of your traffic sources (on the far left of the graphic) like your website, blog, affiliate partnerships, YouTube channel, Facebook page, etc.

It isn’t designed to collect an email address – that is the job of a “squeeze page” (the second step from the left) which usually offers a freebie such as a webinar, PDF, or template in exchange for an email address. 

It isn’t designed to build and nurture a relationship with your customers – that is the job of your email list and parable-based emails (in blue).

The sales page is the final step in a long process of creating your perfect customer, educating them step by step until they are ready to fully benefit from your program. 

There are no magic bullets

I would say this was the big takeaway from this entire program – there is absolutely no magic bullet to selling online courses. They are a business like any other, requiring a long-term dedicated effort and systematic improvement.

I’ve been a big advocate over the years for more people to create online courses. It is truly wonderful work to do, combining the satisfaction of helping people change their lives with the flexibility of location independence with the profitability of near-zero marginal costs with the scale of online distribution.

But what I’ve seen time and again is that it is much easier to create an online course than to sell one. The tools of content creation get easier every year. Almost anyone can now outline a curriculum, film some videos, design some decent-looking graphics, and post about their launch all over social media. 

But paradoxically, the knowledge and practice of online marketing is as scarce as ever. Not because it is a big secret. All the advice you find for free on blogs, YouTube, and webinars has a lot of truth to it. It is scarce because it requires deliberate practice. Every single course has a different kind of customer, with a different psychology, requiring different beliefs, supported by different kinds of content. That customer has to be researched, explored, experimented with, and deeply understood for the course to find “course-student fit.” 

For this process to succeed in a reasonable timeframe, course creators simply must have coaching and accountability. There’s way too much to figure out on your own. Way too many ways to get stuck and lose momentum. 

Luckily, there is an existing industry that has been around for decades with proven best practices – the direct response marketing industry. Unlike brand marketing, direct response marketing can be measured. Which makes it the best choice for small businesses that can’t spend millions on Super Bowl ads. Once again, these methods are not a secret. But everyone needs help in applying and adapting these best practices to their niche. Everyone needs a mentor who has walked the path before. 

This is why I am determined to do everything I can to promote the growth of a consulting, coaching, and training industry around online course marketing. The world needs people to teach what they know, but those people need advisors and mentors who can show them the path to sustainability. The very best way to master something difficult is to find someone who has done it before, and follow their advice. 

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