Welcome to issue #7 of Side Hustle Stories. Each week, I share honest lessons from building a creator-led business while balancing a FT job and family life. No fluff. Just stories, frameworks, and behind-the-scenes decisions from someone doing the work in real-time. If you're building your own thing on the side—or want to—you'll feel right at home here.
Two years ago, I launched my first self-paced course. Made about $20K over six months. It represented my first “passive income” as a creator, and I was thrilled.
Except most people never made it past chapter two.
I kept telling myself it was because people are busy. That's what everyone says about self-serve courses anyway—"nobody finishes them because life gets in the way."
But after coaching over 100 people through my live Impromptu Speakers Academy program, I realized something: The problem wasn't that people were too busy. The problem was that I built a bad course.
The Self-Serve Course Hate is Real (And Mostly Deserved)
Let's be honest about why self-serve courses get roasted:
"Everything's free on YouTube anyway." "They're just overpriced info dumps." "Nobody actually completes them."
Most of the time? They're right. I've bought plenty of courses that felt like watching someone's unedited brain dump for hours.
But then there's Justin Welsh's Content OS. Under $200 USD. I've gone back to it dozens of times over the past year. It's become the foundation of how I create content. Short, specific, actionable. No fluff.
That course proved something to me: The format isn't broken. Most courses are just engineered poorly.
So I'm Taking the Challenge
Instead of giving up on self-serve courses, I'm doubling down. I'm turning The ISA into a self-paced program—but this time, I'm taking a different approach.
Here's what I learned from my first failure and four cohorts of live coaching that I'm building into version 2.0:
1. Specific Knowledge Beats General Advice
My original course was too broad. "How to be a better speaker" could mean anything.
The new, do-it-yourself ISA is laser-focused: Help busy professionals organize their thoughts and speak clearly when put on the spot. That's it.
This specificity comes from real experience. I've now coached 70+ people in group settings and 40+ in one-on-ones over the past 2 years. I practice the methods I teach as the Head of Business Development at Lucid — my day job. I know exactly which frameworks work when someone's mind goes blank in a meeting. I know which exercises build confidence fastest.
When I launched my first self-serve course 2 years ago, I hadn’t worked with enough students. If I’m honest with myself, I didn’t have as much confidence in the curriculum as I do now.
Naval Ravikant talks about specific knowledge. It’s knowledge from deliberate study or experience that’s narrow in scope but profound in depth. It compounds over time through learing and experience. It’s highly specialized and acts as a form of leverage.
Now I’m not saying that people taking my course can “acquire” this specific knowledge that I have, to the level of depth that I have, when it comes to impromptu speaking. However, I do believe that creators who obsess over their crafts will build unique courses that help their students get ahead. The rest trying to make a quick buck off passive income will fail their students. I’ve taken way too many of these generic courses, only to leave disappointed.
You can't get that knowledge from theory. You have to earn it.
2. Make the Time Investment Obvious
"Become a better speaker" is vague and overwhelming.
"Spend 20 minutes a day for 20 straight days to speak clearly without scripts" is concrete and doable.
I learned this from watching people succeed in my live cohorts. The ones who improved fastest weren't the ones who studied the most—they were the ones who practiced consistently in small chunks.
Make the time commitment to transformation short. And make the end outcome specific and concrete.
3. Application Beats Information
This was my biggest mistake the first time around. I gave people great frameworks, then basically said "go practice somewhere."
No prompt bank. No structure. No easy way to actually do the work.
The transformation doesn't happen from watching videos. It happens from speaking. So I built a simple web app that guides people through daily practice sessions. They log in, get a prompt, record themselves, and move on. You can see a quick demo of the prototype above.
The theory matters, but the reps are everything.
Why I Still Believe Self-Serve Will Win
Yes, live coaching is powerful. I love working with people in real-time, and some will always prefer that experience.
But not everyone needs it. Some people prefer their own pace. Others can't make the live calls. Many don't want to spend $1,000+ for a group program.
The demand is there—that's why people buy courses in the first place. The motivation exists. We just haven't built the right experience yet.
Most creators dump content into a portal and hope for the best. Then when people don't finish, they blame the format instead of their design.
What's Coming Next
I'm launching the new self-serve ISA in the next few weeks. Same frameworks that worked in my live cohorts, but engineered for people who want to learn on their own schedule.
And honestly? I think this is just the beginning.
AI is going to change everything about self-paced learning. Soon, every coach will be able to build personalized feedback into their courses. Imagine practicing a presentation and getting specific notes on your delivery—from an AI trained on your instructor's teaching style.
That's the future I want to build for The ISA, assuming this launch goes well.
The "self-serve courses are dead" crowd is looking at the wrong problem. The format isn't broken. We just need to build better courses.
Want to be among the first to try the new ISA when it launches? Join the waitlist here and I'll let you know as soon as it's ready. Plus, you'll get early access pricing when we go live.
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