12 Lessons Generating $20M+ Selling Writing Courses Online

The Operational Moat

Operational complexity becomes your competitive advantage as your business grows beyond simple beginnings
Early-stage businesses are lean and straightforward, but scaling requires managing CRM systems, customer segmentation, paid ads tracking, and cross-referencing purchase histories
Most competitors cannot replicate the layers of complexity you've built, creating a defensive moat that protects your market position
The complexity itself prevents new entrants from easily copying your business model

Subjectivity doesn't scale when you need multiple team members performing the same functions
Small businesses rely on talented individuals making subjective decisions, but this creates inconsistency as you grow
Every action must become objective with clear standards—from response formats to message length to communication structure
Transform intuitive decisions into documented processes that anyone can follow consistently

Customers want valuable outcomes faster with less work, not more educational content
Adding more resources and information actually confuses customers by presenting too many paths forward
The winning strategy is removing tangential steps and focusing exclusively on the core outcome
Whittle your curriculum down to the essential 5-8 steps that directly lead to the desired result

Wanting to start something new signals you don't know how to improve what you already have
When you hit a plateau, the impulse is to create another product or service instead of scaling the original
Starting new things deprives you of learning how to improve your existing successful venture
Eventually you'll discover how to scale the original, but your focus will already be split across multiple initiatives

As an entrepreneur, you live in constant maximum risk, so minimize personal financial risk
Running a business is the riskiest thing you can do with your money—don't compound that by making speculative personal investments
The more risk inside your business, the more you should de-risk your personal life
Take money out of the business and invest it conservatively rather than chasing high-risk opportunities

Only pay commissions while salespeople remain on your team, not in perpetuity after they leave
This structure retains talent because closers with outstanding commissions won't want to forfeit them by leaving
Clean commission structures prevent paying former employees for months after their departure

Budget at least $1 million in "ignorance debt" when transitioning from organic to paid advertising
Paid ads require completely different skills than organic content marketing
Organic is easier but less controllable; paid ads are more predictable but riskier
Expect to spend significant money on failed experiments before discovering what works

Every new marketing initiative requires a full year learning curve before it becomes profitable
First attempts at new channels—webinars, paid challenges, low-ticket funnels—will likely fail
Expect to run 10-20 iterations before figuring out how to make a new channel work effectively
Most people quit too early, which is why persistence through the learning curve creates competitive advantage

What gets measured gets improved; what gets maintained atrophies—everything is either growing or dying
Set up dashboards for every new initiative to track success metrics
Create "dopamine channels" that send real-time notifications when customers purchase, creating immediate feedback loops
Nothing maintains itself—initiatives only succeed as long as you actively deploy effort behind them

When talented team members hit ceilings, create new roles or empower them as entrepreneurs
High-agency employees need growth paths that leverage their skills within your broader vision
Consider seed-funding talented team members to build their own verticals inside your portfolio
Ensure individual goals align with and fit inside your company's larger vision

Once you cross $3 million in annual revenue, invest heavily in video content for maximum leverage
Video creates high resonance with audiences—watching two hours of content dramatically increases purchase likelihood
Video serves as pillar content that teams can repurpose into shorts, threads, and social posts
Video acts as a forcing function to articulate and scale your knowledge effectively

When someone says a project will be "fast and easy," assume it will be slow, hard, and expensive
Translate optimistic estimates into realistic expectations: projects will take longer and cost 2-10x more than initially projected
This mental reframing prevents disappointment and helps you plan resources appropriately