How I built my first digital product

What comes to mind when someone tells you that they’re launching a digital product? Is it the poorly designed WordPress pop-up begging for your email? Or the eBook that promises to answer life’s most vexing questions? Whether it’s an online course, a video series or package of “templates,” it can feel like there’s a special place in hell for digital products right alongside their Gen X sibling, the late night infomercial.

But four years of writing the RadReads email newsletter and blog left me with paltry amounts of digital income; the time had come for me to confront the scary “M” word: Monetization.

The M-word scares the bejesus for many reasons. For starters, monetizing digital content is very difficult for the simple reason that it requires huge audiences (well beyond the current 16k readership). Furthermore, any entrepreneur can attest to the awkward (and slimy) feeling that arises when you ask someone to pay for something.

Yet the most terrifying part about the M-word is that it risked jeopardizing the trust that I had spent years building with you, the RadReads community. Was it worth poisoning a collaborative relationship by introducing an economic transaction?

However, on the flip side – if executed correctly – a digital product might be the ultimate form of Internet manna: the elusive passive income that would continue to propel a growing lifestyle business.

TL;DR 104 hours of work for $9,325

I launched a one-time online course (aka workshop) called The Fulfilling Path to Financial Independence on May 2nd. The launch exceeded my expectations across many metrics: It took 104 hours (spanning 3 months) to create a 2-hour workshop attended by 114 RadReaders generating $9,325 of net revenue, of which 4% could qualify as passive.

This post will detail the tricky transition from creating value to capturing value and I’ll share with you my launch playbook, how I came up with the course idea, the required skills (and tech stack), the unit economics and, most importantly, the wild emotional ride.

The tl;dr is that is that an online course is a promising medium for RadReads but there are waaaaay easier ways to earn $9k. And the marketing demands will never make this “passive.”

A table with # of buyers, revenue (gross and net) representing 9,325 in total sales.
Cheers to a Quarter’s worth of work!

1. The “audience-first” strategy

Since I left my corporate job in 2015, I’ve become an avid digital content creator. Initially, creating content was motivated by the lack of a business idea. Financially, I had set aside a portion of our family savings (roughly 18 months worth) to try to figure out how I could ultimately work for myself.

What happened next is the byproduct of consistency and luck. I put in the hours (shown below) but got a few fantastic breaks, specifically when Bloomberg and CNN wrote about my RadReads journey.

1,240 hours of content creation
Via IG: @radreadsco

And in that process, I unintentionally built up an audience, years before ever collecting a dime (excluding Patreon donations) for my digital efforts. In his post Building a Startup: Build an audience, first Product Hunt founder Ryan Hoover lists the three advantages of this audience-first approach:

Recruiting ?: When you’re pre-product + pre-traction, it’s difficult to convince anyone (technical or not) to join.
User Acquisition ??: Acquisition is difficult pre AND post-product. Sooner you can de-risk this the better.
Research ??: Audience-building leads to customer development and a better understanding of who you’re building for.

Of the three, Research has been my competitive advantage. It’s helped me understand the questions RadReaders are looking to answer and hone in on the topics that matter to them: the tricky intersection of how you spend your time, how you earn your money, and how to live a meaningful life. Here are two places that capture this diligent focus on research: a Google doc of hundreds of RadReader Questions (left) and an AirTable of Story Ideas (right):

A Google doc of hundreds of RadReader Questions (left) and an AirTable of Story Ideas (right)
I hear you, I really do!

Creating Value vs. Capturing Value

My motivating principle for RadReads is to teach everything that I know. If there’s something I know that may be helpful to someone else, I feel a strong sense of duty to get it out to them. Creating value (for others) feels natural and aligned with how I want to live my life. Capturing Value does not. It feels slimy and transactional.

Aspiring solopreneurs always ask me “when’s the right time to quit your job?” And like parenthood, there’s never the right time but one thing’s certain: when you have a full-time job, you have the luxury of focusing on creating value. In Steph Smith’s post You don’t need to quit your job to become a creator she calls out the benefit of having “projects that aren’t influenced by the need to make cash immediately.” She adds:

More importantly, I can focus on expressing myself through projects I truly care about, instead of focusing on what may generate money, and through this process, I stay close to my values. In other words, I can focus on creating value, instead of specifically on capturing it.

My savings from my finance career provided the runway to spend a disproportionate amount of time creating value; 94%, to be specific. (And to be clear, I’m talking exclusively about digital revenue – I began consulting and coaching within a year of quitting BlackRock.)

The timeline below shows that range of activities that fell under creating value without the pressure of monetization. And during that 3.5 year period, I was able to plant seedlings of ideas and build up the “research” behind what RadReaders cared about.

The create vs. capture timeline to launching the RadReads online course.

Enter the Impostor Syndrome

Flipping the switch from creating to capturing left me rife with impostor syndrome and anxiety. In Working Not Working, Nada Alic interviewed 11 Creatives Working Through Impostor Syndrome and I identified with “Hyla’s” (a director) fear of mediocrity:

Constantly asking myself if I’m good enough as the person who is already doing the thing I want to do. I also fear being mediocre, I’d rather someone say something I make is shit than be like ‘meh’ about it. These thoughts play a big role in my procrastination. What’s the point of putting in the work if it’s just gonna be perceived as ¯\_(ツ)_/¯?

This was exacerbated by fears of social rejection. I would interpret a potential buyer’s question about the course as a critique. I nearly shat my pants when some bad-ass entrepreneurs signed up (fearing I’d let them down). And I couldn’t shake the feeling that RadReaders were saying to themselves: “This is it, he’s jumped the shark – time to move on.”

As if that wasn’t bad enough, the icing on the cake was my nagging scarcity mindset (which is ironic, given that this was a course topic) which said: if you fail at this, you’ve ruined your shot at entrepreneurship and you’ll probably end up dead and broke (and without insurance) in a ditch.

How to overcome Impostor Syndrome

Honestly, I don’t think you do. But a few things helped. I hired Taylor Pearson, an experienced coach who had been in my shoes before. This playbook is thanks to Taylor and equally important, he provided the affirmation that I was fully capable of doing this.

But more importantly, you don’t ever slay impostor syndrome, you simply renegotiate your relationship to it. And to me this renegotiation was simple. I gave myself the following mantra:

I’m going to dedicate my heart and soul to this course. It’s gonna be so damn good, thorough and honest, that you guys will leave saying to yourselves “Damn, that was worth 5x what I paid for it.”

And I topped it off with this gif to capture the raw emotion:

A hype man, excited and inspired to create

2. Identifying a course topic

I was repeatedly warned by fellow online course creators to avoid a common trap: spending months on a course only to realize that there was no demand for the thing you created. One of my go-to resources in the launch process was Brian Harris’ guide to launching an online course. Harris makes you take a hippocratic oath that you won’t build a digital product before validating the demand:

Thing #1: Raise your right hand.
Thing #2: Say this out loud…

Never to build a product.
Without first validating that people will actually pay me money for said product.

There’s a very unsexy way to de-risk a digital product idea: offer it as a service. In his essay Do Things that Don’t Scale, the venerable Paul Graham recommends this approach to B2B startups:

Take over-engagement to an extreme, and to pick a single user and act as if [you] were consultants building something just for that one user. The initial user serves as the form for your mold; keep tweaking till you fit their needs perfectly, and you’ll usually find you’ve made something other users want too.

Even if there aren’t many of them, there are probably adjacent territories that have more. As long as you can find just one user who really needs something and can act on that need, you’ve got a toehold in making something people want, and that’s as much as any startup needs initially.

Every single entrepreneur considering a digital product should run their ideas through the following waterfall:


  • What’s a question/topic I’m often asked about?
  • Do people want to regularly discuss this topic for free?
  • Does anyone want to pay me as a consultant for this expertise?
  • Would they consider a course on this topic?


The “funnel” I used to identify course ideas

Given my rich data set from years of interacting with the RadReads community, I was fortunate to have some clues. People often asked me for advice in the following domains:


  • Investing and personal finance
  • Career change
  • The psychology of money
  • How to become a solopreneur
  • Organizing your workflow
  • How to become a better professional


My Money Coaching practice satisfied most of the requirements in this framework: I had over twenty coaching clients at a high price point. Furthermore, I was also getting paid speaking gigs on the topic of the Psychology of Money. And while there were thousands of personal finance bloggers, the landscape for this sub-category felt nichey enough that I could cut through the noise.

A “digital workshop” as a Minimum Viable Product

Returning to Brian Harris’ Hippocratic Oath on validating demand, I still didn’t have the confidence to go balls-to-the-wall and build out a full-blown online course. So I asked myself: What would a low-cost, high value exchange of knowledge look like?

A digital workshop that mirrored my paid speaking gigs felt like the right balance. But thanks to a vibrant tech stack, I could enhance the experience with workbooks, a Slack channel, multiple Q&As and curated reading lists.

The sequencing of the product launch. Workshop -> Cohorts -> DIY

The longer-term vision was to increase the depth, production quality, and scaleability with each iteration – but without being married to a specific topic and with the ability to pivot quickly if the demand wasn’t there. This approach was reinforced by one of my mentors, Tiago Forte (creator of the magnificent course Building A Second Brain). On the Rad Awakenings podcast he captured the versatility of this approach:

One day you can run a workshop and then realize that it doesn’t work, so the next day do 1:1 consulting. It’s really easy to pivot. If all you have is a website describing your service, all you have to do is change the description on your website.

So armed with a topic – The Psychology of Money – we were off to the races. But there was just a little problem…

3. It’s all about marketing

Here’s a snap survey: When you wake up each morning, what are some of the first thoughts that cross your mind? I’m pretty sure that gut-checking your psychology of money is not one of them. Which leads me to my biggest surprise (by far) in launching a digital product: the importance of marketing.

Like, duh. But it’s one thing to intuitively know the importance of marketing; and another to spend tens of hours perfecting your sales copy and fine tuning messages that will be used across blog posts, Mailchimp campaigns and Tweets. And if you think it’s hard to build an audience – imagine how hard it is to get people to open their wallets, punch in their credit numbers and buy something from a semi-anonymous digital storefront.

Furthermore, think about buying any service online. Unlike a product purchase, you don’t interact much with anything other than words (and maybe a teaser video). These words could be a course outline, testimonials ore a super-compelling narrative to draw you in. The words matter. A lot. (Obviously, you have to deliver with your product.)

The “alarm clock test”

Let’s now return to your first thought in the morning. It could include “how can I make more money” or “how can I improve at my job” or “how can I feel better about myself?” Scott Norton, co-founder of Sir Kensington’s described marketing as offering “material solutions to emotional problems.” What emotional problem would the workshop solve?

My coach Taylor taught me a simple alarm clock test – a useful barometer for a prospective customer’s pain point. How could we create a course that crossed this threshold while being part of the zeitgeist? That’s where we landed on FIRE (aka Financial Independence, Retire Early).

Anyone who’s seen how our family spends our money and where we choose to live can quickly see that I’m not a FIRE devotee – yet I subscribe to many of FIRE principles (saving and investing aggressively, being resourceful about earning money). FIRE, or specifically Financial Independence provided that wedge to create a fresh take on this buzzy topic.

Creating a sales page

The foundation for our marketing campaign was a Sales Page. As a writer, you’d think that this would be an easy task. But it’s a tricky mix of copy writing, psychology and outright sales. In the template below you’ll see bizarre sections like:


  • Grab their attention (with a big promise headline)
  • Show the pain and cost of development (establish empathy and affinity)
  • Futurecast (explain how their life will improve)


This was a painful document to write as it required a completely different writing approach (that can make you feel like a snakeoil salesman). It took over 8 hours can see the iterations of the Sales Page in this Google Doc.

A 16-step template for a sales page

Being able to write good marketing copy is a high-impact lever to grow a digital product. Here are some tips for other creators looking to improve this skill:


  • Consider the true pain points of your audience and don’t be afraid to engage them
  • Collect stories that will deeply resonate with your audience about these pain points
  • Understand the basics of copy writing; it’s short, conversational and direct
  • Look around and you’ll realize everything is a sale (billboards, marketing emails, podcast ads) – pay attention to what resonates with you


Throw in a thirst trap for good measure

As I realized the importance of psychology (and personal aspiration) I said “F**k it” and threw in the following image. (At home, I rarely wear shirts but I tend to hide that in my public persona.)

Khe holding a surfboard with a sixpack.

The inclusion of this picture was very highly commented and while I have no way of attributing sales to it, I’m certain that it helped.

And yes, I like that pic 😉

A content marketing framework: Problem-Agitatation-Solution

Once the sales page was complete, I needed to “tie” my weekly blog posts to the course itself. Taylor introduced me to the Problem-Agitation-Solution framework for content-based marketing. The CopyHackers blog describes this formula as follows:


  • Problem – Present the problem your prospect feels
  • Agitation – Poke at that problem until it’s visceral
  • Solution – Present your solution to the agitated problem


I applied this sales sequence with the three blog posts leading up to the course launch:



These were very difficult posts to write and I think the first two landed and the last one flopped. Specifically, I agitated almost too well by drawing the vitriol of the FIRE community with this tweet:

Below is a summary of unique visitors, which (true to my approach) are surprisingly consistent:

Unique visitors using the PAS framework
Agitate and Solve both went mini-viral

4. What other launch skills are required?

In the early days of blogging, you’re not accountable to any customers. Yes, you may have a publishing schedule – but at the end of the day, you’re not beholden to it. The commitment ratchets up slightly with Patrons – but even then, the relationship is underpinned by gifts and generosity. Not commerce. With a digital product, you’ve entered into an economic relationship with your customer. The stakes instantly go up.

Launching your first digital product will test your ability to cobble together multiple tech platforms, be really good at email marketing, maintain a minimum threshold of good design, create and deliver a syllabus, and to remain unfazed by death by a thousand cuts. It’s the first time in my RadReads journey that I felt like I was running a small business.

Skill 1: Develop a “hacker mindset”

Technology has been so commoditized that a non-coder like me can piece together a business in the same way a chef can take discrete ingredients and mash them up into a delicious meal. But just because you don’t need to code, it still requires a strong intuition to put all the pieces together. Here’s the tech stack I used in creating the online course:


  • SiteGround: Host the blog
  • WordPress: Content management system (“CMS”) to manage all the posts
  • Thrive Leads: WordPress Plug-in to capture email addresses
  • Mailchimp: Send emails and manage subscriber list
  • Patreon: Collect donations (and give discounts to Patrons)
  • Sketch: Create logos and banners
  • Keynote: Create slide deck used in presentation
  • Stripe and Paypal: Payment processing engines
  • SendOwl: Payment front-end and order management system
  • Zoom: Video chat tool for actual course
  • QuickTime video: Video editing tool (for trimming) Zoom videos.
  • Notion: Digital notebook for creating syllabus and hosting workbooks
  • Zapier: Connecting the various platforms (like Patreon + Mailchimp)
  • Slack: Chat tool for course buyers
  • Teachable: Hosting platform for replay


None of these are particularly challenging to use in isolation – however, as Murphy’s Law would dictate, combining them exponentially ups the ante on complexity. Understanding the tech is not the most important skill, IMO – it’s being thorough in eliminating edge cases and persistent in debugging situations gone awry.

Skill 2: Be good at email

When you have customers, the primary medium of interaction will be email. And while I feel conversant using Mailchimp, sending a weekly newsletter is not the same thing as servicing prospects and clients. The latter requires heavy stratification (i.e. sub-groupings based on discounts or specific landing pages) of your audience, automated sequences (i.e. purchase confirmations and dial-in logins), and moving prospects through a funnel. I’m proud of the click rates below (and even prouder that it only generated 6 unsubscribes!)

Campaign and click metrics across cohorts.
Email click rate: 10%
Purchase/sale ratio: 5%
The Patrons were segmented to offer them a discount

This was exacerbated by my apprehension towards pissing off a loyal audience. I didn’t want to send too many emails and I definitely didn’t want to send emails to the wrong people. When you’re dealing with 16,000 subscribers, eyeballing the lists becomes impossible and it becomes hard to run quality control on what you’re sending. (I was particularly frustrated with Mailchimp’s confusing segmentation process, which may tempt me to switch to ConvertKit.)

If you’re thinking of launching a digital product, you can get ahead of these email issues by experimenting as follow:


  • Segment your audience: Even if you only send a weekly email, learn to group your audience by engagement/loyalty, acquisition channel (i.e. how they found you), and areas of interest (using mini-polls).
  • Understand automated sequences: You could set-up an “welcome” sequence for new subscribers or create an opt-in “email class.”
  • Develop templates: Users appreciate consistency and templates can keep you “on brand.”


3. Clean design matters

Take a look at these “buy” buttons:

A red "buy" button and purple one.

The one on the left is SendOwl’s default buy button and the one on the right is one I created as a replacement. Now, I don’t know jack about design – but I do know that a red button with a blurry font does not give me the feels (nor the confidence) to punch in my credit card number on the Internet. And since defaults are hard to change, making the replacement button took about two hours (and my new button still was a bit blurry, smh!).

Next, think about the difference between a Dell Laptop and a MacBook. They both pretty much do the same thing – but one leaves you feeling good, while the other leaves you meh. I’ve always maintained that good design communicates trust and hold myself to a reasonable (and DIY) standard. One place where this showed up was in the actual presentation itself. It was visual, clean and consistent with RadReads voice and aesthetic. Here are a few of my favorite slides:

Four keynote slides emphasizing design (and including spreadsheets)
I’ve quietly become a Keynote Ninja!

Don’t take this as a call to hire the best graphic designers or to learn Adobe Photoshop; instead, consider how to use the 80/20 rule to liven up your digital assets. It will get noticed.

4. Putting the course together

You might accuse me of burying the lede by talking about creating the course itself so late in the post. And at the end of the day, it did command the lion share (45 hours) of my efforts. (After all, those beautiful Keynote slides don’t create themselves!)

The approach I used for each of the eight modules was to lead with an anecdote, followed by research and analysis and concluding with a set of questions and action items. This was made easier by the fact that I typically structured my posts and talks in this manner and the most challenging part was stringing it all together into a cohesive narrative.

The 8 module course syllabus
The course syllabus

Given that this was a time-constrained (i.e. a 90 minute course) minimum viable product there’s a ton of room for improvement in the next iteration.

Your turn!

My first foray in digital product land exceeded expectations: sales, conversions, and initial customer responses (only two refund requests). Synthesizing the feedback and launching a cohort-based live class still feels daunting, but thankfully much of the infrastructure is already in place for Round Two.

Is it worth it? Well to be blunt, there are waaaaay easier ways to earn $9k. But as I mentioned in course, when something doesn’t feel like work and can simultaneously bring you financial independence – you’ve found a secret advantage!

Lebron James cluing you on a secret about digital products
Taken directly from the presentation

Are you ready to begin your journey on the Fulfilling Path to Financial Independence.

In summary:


  • Start by building an audience: By focusing on creating value, you can hone in on their needs and questions.
  • Identify a topic: Engage with your audience and ask them explicitly which problems they’re trying to solve. Start a 1:1 consulting business to test paid demand.
  • Learn how to market: This includes storytelling, copy writing, persuasion and the deep empathy.
  • Other launch skills: You’ll be running a small business which requires a “hacker sensibility,” responsiveness, and the ability to run good email campaigns
  • Have fun! Remember that this is your expertise and passion – make sure you capture that spirit in your product


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