Early last summer I joined Teachable’s “Creator Challenge.”
The premise was to research, create, and launch an online course over the next three months.
On top of that, Teachable provided expert support, a community of fellow instructors, and a little friendly competition.
People have been asking me about creating an online course for years — but since I tend to work better with a deadline, I jumped in on the challenge.
Why Online Courses?
First of all, it might make sense to explore the benefits and appeal of an online course.
For students, it’s a way to condense the information they need to achieve some transformation they want. The information is online, on-demand, and can be consumed at their convenience.
For instructors, there’s a beautiful simplicity in the online course model: serve more people than you ever could one-on-one, and create something once and sell it over and over again.
Why Hadn’t I Done a Course Already?
If courses are so great, why hadn’t I done one already?
Well, the truth is I had. Back in 2014-2015 I put out a couple different courses.
The second was a 30-Day Plan, Launch, Hustle Challenge, which I ran a couple times in the fall of 2015. While feedback was overwhelmingly positive, my students weren’t reaching the monetary goals they set in the course.
Maybe the 30-day timeline was too tight, maybe the instruction sucked, or maybe it was information overload. In any case, the results (or lack of student results) was depressing.
Because of that, I never launched the challenge to my full email list.
What to Create a Course About?
The first question to answer, after committing to the challenge, was what to teach.
During Teachable’s free webinar, they suggested these prompts to begin brainstorming:
- what are you good at or passionate about?
- what do people come to you for advice about?
- what have you overcome?
- what have you spoken about?
- what types of questions to people ask in comments/group?
- what’s the most popular content on your site?
Using these questions, I came up topics related to:
But the idea that most people come to me for advice on is finding a side hustle. And in my surveys of email subscribers, the dual pain points of “coming up with an idea” and “just getting started” always stand out.
In fact, the segment of survey takers who indicate they’re still looking for an idea is often the biggest slice of the pie.
So I decided to put together a course to address that.
(The other topics could wait for another day!)
What Makes a Good Course?
As I worked my way through Teachable University, the course the software platform provides to instructors, I took some more notes.
Just a heads up here, if you’re not familiar with Teachable. Teachable makes it super easy to set-up and sell an online course of your own. They handle the hosting, the sales pages, the payment processing, the student tracking, everything. They even have a free plan if you’re just starting out.
Provide a Transformation
The most important thing I took away from the training is that an online course needs to provide a transformation.
What’s the tangible outcome of your course?
This isn’t some university seminar someone is taking to fill in their class schedule and get graduation credits. They’re taking this on their own time out of their own interest. What’s going to be different in their lives after working through your material?
The transformation I came up with was going from no side hustle ideas to your first side hustle income.
Among Side Hustle Show friends and guests, other course transformations I’ve seen include:
- Feel confident running Facebook ads
- Learn to play modern songs on the Piano in 21 Days
- Start a virtual assistant business
- Bake awesome sourdough bread
- Love your wardrobe
Simplify the Steps
Yet some people still haven’t experienced the life-changing thrill of their first job-free dollars!
Why is that? How could I break it down into the smallest actionable steps?
That was my challenge in coming up with the material for the course — how to best distill the years of content into a step-by-step plan that works.
Narrow the Focus
With the topic of side hustling being hopelessly broad (something that honestly held me back from creating a course for years), I knew I had to narrow the scope right away.
So I decided to tackle the specific business model of starting a service business. Freelancing, consulting, coaching, and any number of other “just do it for me” types of services all fall under that umbrella.
Starting with service has the advantages of having:
- Very low or even zero startup costs
- The ability to quickly validate ideas
- A fast path to the “money milestone” — your first customers
It’s an area I’ve had some experience in, from painting houses to editing books, and think it’s a great way for people to begin side hustling.
On top of that, I found that more Side Hustle Show guests started with a service business than any other business model. Safety in numbers!
But First, a Quick Pre-Sale
I began outlining the course, but then remembered my notes from several podcast guests that sold courses. “Don’t build it and then sell it; sell it, and then build it,” they advised.
In other words, create a pre-sale.
So I decided to introduce the course to a small segment of my email list, with just a promise of what would be inside.
In exchange for them taking a risk on me, they got a special discount on the purchase price. ($99 instead of $199 later.)
To create this segment, I actually looked at the latest survey responses, and kind of manually filtered to those who:
- indicated they were still looking for an idea
- said their biggest goal was to just get started
- noted they were making $500/month or less from their side hustle efforts so far
Importantly, I also filtered out everyone who said they were most interested in starting an Amazon or e-commerce business, since that’s not what the course would be about.
My Pre-Launch Email Sequence
My pre-launch campaign ended up generating 20 sales, or about a 2.5% conversion rate:
It was enough validation to continue with the challenge. If I’m being honest, I was already doing the math in my head for a full press, full audience launch … 2.5% x 60,000 email subscribers x $199 = almost $300,000!
(Spoiler alert: that didn’t come anywhere close to happening!)
I sent 3 emails to this list:
- Introduction – basically, “Hey, I’m making this thing and thought you might be interested.”
- FAQs – An email based on questions I’d received/anticipated receiving.
- Last chance – basically, “The limited-time half-off pre-sale special ends tonight. Are you in?”
But before you can even do a pre-sale, you’ve got to do some work in Teachable…
Building Out a Sales Page
It was a little weird to create the sales page before the product was even finished, but such is the nature of a pre-sale.
Thankfully Teachable makes this easy. The Start My Side Hustle sales page definitely isn’t the best sales page in the world, but it’s functional. And I can go back in and edit it any time.
I actually bought a custom URL for, which is totally unnecessary, but thought it was good for branding or if I ever had occasion to mention it on a podcast: StartMySideHustle.com.
On your sales page, you’re trying to:
- identify your target audience
- empathize with their goals, interests, fears, beliefs, and challenges
- showcase your qualifications to help them
For testimonials, I used feedback from my 2015 challenge.
A note on Teachable’s pricing tiers. You have to do the math on what tier makes sense based on your expected enrollments and price point. I started at the $39/month plan, which charges a 5% fee on every purchase. Selling pre-sale enrollments at $100, I’d “breakeven” on the $60 upgrade to the $99/month plan after 12 students.
Expecting more than 12, I upgraded to avoid the 5% fee. You can adjust your plan at any time.
Creating the Curriculum
Getting back to the course itself…
As I thought about the transformation people told me they wanted most — pick an idea and get started — I began mapping a curriculum.
Working Backward to Create an Outline
For this, I actually found it helpful, as Teachable recommended, to start at the outcome and work backward.
I imagined a side hustler who just landed their first client. What was everything that had to happen to get them to that point?
From there I created a reverse outline that looked like this:
- Marketing and Sales
- Idea Selection and Validation
- Idea Generation
- Business Idea Basics
- The Entrepreneur’s Mindset
That last section (which became the first section of the course) was actually included based on a series of exploratory phone calls I did with members of the Side Hustle Nation community. I asked questions like:
- what’s holding you back from starting?
- what are your biggest fears related to your side hustle?
I was honestly surprised how often mindset-related issues came up. Imposter Syndrome. Fear of failure. Fear of Success. I didn’t know that was a thing!
While I knew I wouldn’t realistically cure decades of mindset issues in a few video lessons, I could at least start the process and provide some exercises that might help.
With the course outline now in hand, my next task was filling in the blanks with actual words and lessons.
For that, I actually scripted the whole thing out almost word by word. I wouldn’t necessarily recommend you do the same, but it helped me feel more confident.
In total, it was over 14,000 words, but I also wasn’t starting completely from scratch.
I had some content related to my outline in my archives and in various books I’d written, so that helped build out the material. It just had to be translated into video form.
(And if you’re creating a course on a topic you’ve covered from years, you won’t be starting from scratch either!)
Filming and Editing
I shot the course videos from my “cloffice” — my home office recording studio in my kids’ bedroom closet. It’s a pretty simple set-up.
- The Logitech c920 HD webcam
- My sweet Side Hustle Show banner to block the backlight from the window behind me. Mine is from HalfPriceBanners.com.
- My podcast recording mic; I switched to a fancy Heil PR-40 around episode 300, but the lower cost ATR-2100 works just fine.
- Some LED lights to try and brighten up the shot. The closet lighting is awful for video.
- Screencast-o-Matic for editing. I added some light text and image overlays to hopefully make things more visually interesting.
Most are me talking into the camera, but some are PowerPoint slides and others are screen recordings.
Workbook and Exercises
Of the courses I’ve taken, I found I assigned those with a companion workbook a higher perceived value. It was something I could print off (or use a tool like PDF Escape) and fill in the homework as I went.
For me, the workbooks took me from a passive student to an active (and action-taking) learner.
So naturally, Start My Side Hustle needed a workbook.
I started working on this myself in Word, but quickly grew frustrated with the formatting. A freelance virtual assistant ended up building out the workbook in Canva, which is much easier to work with for this sort of thing!
The workbook is around 20 pages and has lots of fill-in-the-blank sections related to different exercises from the course.
The final element of the course itself is a handful of surprise “Easter Eggs” I hid throughout.
These were just meant to be fun little bonuses for students to uncover as they went through the material. I’m thrilled whenever anyone finds one and sends me a note.
Uploading Content to Teachable
With the course complete, it was now time to upload the material to Teachable.
I found the interface fairly straightforward, and added written notes to each video lecture. Since I already had detailed video scripts, it didn’t take a ton of time to edit and format those.
Other Important Tech Stuff
Despite the perceived simplicity of the online course business model, I think you’re beginning to see there are a lot of moving parts that go into it.
Or at least by this point, I definitely was!
Adding a Facebook Group
Most courses I’m a student in have some sort of community element for peer support and instructor Q&A. So I created a private companion group for Start My Side Hustle students as well.
ActiveCampaign Tagging and Automation
What happens after someone enrolls?
In ActiveCampaign, I wanted to make sure that student was tagged as a course customer, and got a welcome/thank you email. I built out a short automation with some important links and next steps that only goes out to course buyers.
Again, not hard, but just another thing to think about.
Launch #2: The Idea-Seeker Segment
By the end of August, the Teachable Creator’s challenge was over. And I’d reached the finish line, having created and sold 20 pre-sale students in my course.
However, the real test was yet to come. Is this something the broader Side Hustle Nation audience would be interested in?
I decided to open the doors again, for a limited time. I don’t love the idea of open-and-shut enrollment for a digital product like this, but understand the importance of scarcity in helping people make a choice and take action.
This time, I created an ActiveCampaign segment of an audience who’d opted in for something related to side hustle ideas. In hindsight, this wasn’t the greatest targeting idea, but I didn’t think about that until later.
(For example, on my Side Hustle Ideas page, I have an opt-in for a PDF version of that post. Most people arrive on that post by Googling “side hustle ideas” or something similar. I feel like an audience of podcast listeners may have been more receptive.)
This gave me a launch list of around 6800 subscribers.
Of those, around 300 people were on the official course “interest list” — I’d started teasing the course creation process and had begun collecting sign-ups of people who wanted to be notified when it launched.
Staying true to my word to my pre-sale students, I increased the price this time around, to $199.
In this launch, I had a set deadline and noted I was capping enrollment at 50 students, whichever came first. My idea here was I wanted to be able to support those who enrolled, but also give a sense of scarcity.
I followed same 3-email sequence as I’d done with my pre-sale, but this time only 14 people bought.
Yeah … 14 out of 6800 is a pretty horrible conversion rate.
What about the 300 people who specifically asked to be notified when it was ready? That sub-segment had a fantastic open rate — over 70% — but only 4 enrolled.
What Went Wrong?
When I went to my mastermind group and asked what I was doing wrong, they asked about my pre-launch.
“You know,” they said. “Warming up your audience. Letting them know you’re going to be launching a product.”
Aside from the small group who’d opted in to be notified of the course, very few of these recipients probably had any idea such a product was coming. And here I was, jumping immediately into sales mode. I vowed to do a better “warm up” next time.
You Didn’t Enroll?
This was kind of an awkward email to send, but it was an important one. After the launch was over, I asked everyone who didn’t enroll why they didn’t enroll.
- The timing isn’t right for me.
- The price is too high (possibly an indicator I need to do a better job of communicating the value).
- The course material doesn’t interest me.
- I missed your email.
Perhaps the most important feedback that came out of this was to create a payment plan option, and to accept PayPal, which is an option on the $99/month Teachable plan.
The Waiting Game
Now it was the end of September. In total I had 34 students and had earned around $4500.
It wasn’t bad, but it wasn’t a home run success either.
Still, I had what felt like a valuable asset on my hands. Lots of other stuff I’d built didn’t take off right away either.
But I wasn’t sure what to do next. It felt like I was kind of in a holding pattern, waiting and hoping for testimonials, trying to support the occasional student who’d message me or comment in the Facebook group.
I was confident in the material and the impact it could have, but I didn’t yet have a “poster boy” (or girl) who’d come out the other side singing its praises.
In Teachable, you can see student activity, and very few people were actually going through the material. A few never even logged in! That was discouraging.
Maybe it was a numbers game. Maybe I just needed more students?
Launch #3: The Big Email Launch
I reasoned that I spent all the time and energy to create this thing, I might as well get it out there.
I knew it could help people, so I set out to do one more open-and-shut launch.
Only this time, I did a few things differently.
Determined not to make the same mistakes again, I studied a bunch of course launch case studies and best practices. The one I referred to the most was this one from Bryan Harris.
I also read up on Expert Secrets by Russell Brunson. Some of his stuff is too aggressive for my taste, but I was able to pick and choose what made the most sense for me.
One thing recommended in Expert Secrets is to create what Russell calls “the stack.” This is everything your buyer gets when they buy your thing, and the sticker price should be several times more than what you’re charging.
Here’s what I came up with:
I added this to the sales page.
Several would-be buyers from the last round requested an installment purchase option, so I created that in Teachable.
Now instead of just the one-off, $199 purchase, people could pay in two $100 installments.
36% of buyers took that option. The big risk there, I didn’t really think about it, is now there’s a chance for future payments to fail.
And sure enough, next month, I started to get notices that the attempted 2nd installment didn’t go through.
Some thoughts here…
- Some potential customers requested $25-50 installment plans. I don’t want to go that low because if your budget is already so tight, I’d rather you focus on the massive library of free resources first.
- Next time, I might add a 10-20% premium on the installment option to account for the failed future payments. Since the price was essentially the same whether or not people paid in full, it’s hard to say that the installment option customers were truly incremental sales.
I created a 10-minute “mini webinar” video. It walks through a Jeff Walker-style Problem / Agitate / Solve framework, and finishes by presenting “the stack.”
I was pretty happy with it and embedded it at the top of the sales page.
Instead of just coming out and announcing the course was for sale, I took my mastermind group’s advice and warmed up my audience a bit first.
This time, my launch segment was around 45,000 people and included just about the entire Side Hustle Nation email list except those explicitly interested in e-commerce.
Email 1: The “Problem” email — everyone says “just start” but it’s unclear “what” to start.
My subject line: “Just start” … but WHAT?
Email 2: The “Agitate” email — In addition to needing to know “what” or have an idea, you’re also facing time and money constraints. No solutions were presented.
I asked people to reply to this one with their biggest challenge and got nearly 200 responses. It seemed like this one really struck a nerve. I tried to reply to each of those.
My subject line: “Which is it, %FirstName%?”
Email 3: The “Solve” email — So what’s the answer? The answer, as demonstrated by 300+ Side Hustle Show guests, was to start with a service business. This email also announced that the cart was open.
My subject line: “Found this”
With the audience now primed and ready, I was ready for the sales to start rolling in. To support the launch, I had several more promotional emails go out over the next few days.
Along the way, I also gave people the option to opt-out of this specific promo, but stay subscribed to the broader newsletter.
Email 4: Course is now open: here’s what’s inside.
My subject line: “Now open: Start My Side Hustle 💡”
Email 5: FAQ email.
My subject line: “Is “Start My Side Hustle” right for me?”
Email 6: Logical appeals. This one only went out to subscribers who’d opened one or more of the previous messages. It mentioned that the course was closing tomorrow, and highlighted the benefits of following a proven plan instead of “figuring it out on your own.” It also mentioned the 30-day money-back guarantee as a risk reversal.
My subject line: “⏩ Is “Start My Side Hustle” worth it?”
Email 7: Last Day. This quick message only went out to those who’d clicked over to the sales page. In hindsight, maybe I should have sent it to everyone. It gave a quick overview of what was included in the course and invited people to join before the doors closed.
My subject line: “Are you in, %FirstName%?”
In total, 49 people bought, for close to $9700 in total sales for the launch. And now around $14,000 overall, including the first couple launches.
It wasn’t the kind of epic 6-figure launch you read about online. In fact, the conversion rate of 49/45,000 is almost laughably low.
Put another way, out of every 1000 people I emailed, 999 said “no thanks.” (Or more accurately, most said nothing at all.)
For addressing what I thought was the #1 pain point for my audience, I was surprised by the apparent disconnect.
But I got it out there.
In writing this re-cap, I think I did a lot of things right, but obviously have a ton of room for improvement as well.
Even though the results weren’t quite what I was hoping for, it was a fun project!
As of right now, Start My Side Hustle is open for enrollment.
My plan is to integrate some of the course sales messaging into my existing auto-responder sequences. I can add links from existing freelance-related content. I can promote it on the podcast.
I think my biggest fear is that without the sense of urgency a deadline brings, people won’t take action and enroll.
Still, I see other bloggers like Michelle Schroeder-Gardner doing just fine with evergreen course sales. Maybe I can crack the code.
And if not, maybe I just re-open a few times a year. That’s OK too. In any case, the asset is there and can continue to serve people (and me), given the attention.
All in all, I’m happy to have gone through the experiment of creating and selling the course. I’m excited to support students as they go through and begin to see results.
If you have any questions about the process or the course itself, definitely let me know!