In this week’s episode, I sat down with Derek Hughes from The Irresistible Writer to talk about how to turn your Substack into multiple streams of revenue (rather than relying on paid subscriptions alone).
In this value-packed episode, we covered:
How Derek lost 95% of his income overnight - and why that changed everything about his writing business (00:45)
Why he stopped building “perfect” digital products (04:34)
How to serve different types of buyers with the same knowledge (low-ticket → high-ticket) (06:44)
Why you should never build a big product before validating demand (and how Derek tests ideas fast) (12:37)
Why writing in a “saturated market” isn’t a bad thing (17:15)
Why paid Substack subscriptions should be an entry point, not the end goal (33:28)
How Derek prices his paid Substack to maximize retention (34:23)
And much, much more…
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Key Lessons From This Episode:
#1: Never Rely on a Single Revenue Stream
One of the clearest lessons from Derek’s journey is how fragile it is to depend on just one source of income.
When his Medium income dropped almost overnight, it forced a rethink - and ultimately led to a stronger, more resilient writing business.
The takeaway: diversification of your revenue streams isn’t optional.
Multiple income streams give you stability, flexibility, and peace of mind - even when one platform changes the rules.
#2: Solve Problems for Yourself, Then Productize Them
Derek doesn’t create products by guessing what the market wants.
He solves problems in his own writing and business first - then turns those solutions into products for his audience.
That’s why his courses, cohorts, and tools resonate: they’re road-tested, practical, and based on real experience.
If you’re unsure what to sell, start by asking: What have I already figured out that others are still struggling with?
#3: Use Low-Ticket Offers as Testing Grounds
Before building premium offers, Derek uses smaller products - like masterclasses or live workshops - to test demand.
When people are willing to pay even a small amount, that’s a strong signal you’re onto something.
Low-ticket offers reduce risk, provide fast feedback, and often reveal which ideas deserve deeper investment in cohorts, courses, or coaching.
#4: Cohorts and 1:1 Work Create Income & Fulfillment
While digital products scale well, Derek found that cohorts and 1:1 coaching brought something extra: higher pricing, deeper impact, and far more personal satisfaction.
Live interaction allows you to adapt in real time, see breakthroughs happen, and build genuine relationships with your customers, all while charging a premium for your time and experience.
#5: Paid Subscriptions Are The Start (Not The End)
Paid Substack subscriptions work best as a starting point, not the core of your business.
They’re great for turning free readers into first-time customers.
But the real monetization opportunity comes after that: courses, cohorts, coaching, tools, and higher-ticket offers.
When someone has bought from you once, they’re much more likely to buy from you again.
So, think of your Substack in terms of an ecosystem, don’t only focus on paid subscriptions for monetization.
