In this week’s episode, I sat down with
, who is the creator of the NEW ECONOMIES publication (with over 75,000 subscribers), to discuss the best newsletter monetization strategies to earn your first $100,000 on Substack.In this value-packed episode, we cover:
What makes a paid tier irresistible - and how Ollie got his first 100 paid subscribers (03:11)
How to price your paid subscription so it feels like a “no-brainer” (08:39)
How small Substack publications can find potential newsletter sponsorships in their niche (19:22)
The 90-day growth blueprint to set your Substack up for a $100k year (24:11)
How Ollie added 33,000+ subscribers through the newsletter recommendations feature (27:00)
How to future-proof your newsletter in the age of AI (33:42)
Ollie’s advice on monetization - paid tier, sponsorships, digital products, and more (37:19)
And much, much more…
Watch On YouTube:
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Key Lessons From This Episode:
Lesson 1: Turn on Paid Subscriptions Early
Don’t wait for the “perfect time” to turn on paid.
Even if you only have a handful of readers, give people the option to support your work right away.
You’ll be surprised at how many are willing to pay if they love your content.
Start with a simple offer, keep the price reasonable, and refine it as you go.
Lesson 2: Make Your Paid Tier Unique
A paid tier works best when the value is obvious and different from your free content.
Instead of piling on perks that overwhelm readers, focus on a few core benefits they can’t get anywhere else.
Whether that’s getting access to exclusive data, private workshops, downloadable templates, or a members-only community.
Make your paid content stand out from your free content, and joining your paid tier becomes an easy yes.
Lesson 3: Use Newsletter Sponsorships to Diversify Revenue
Half of Ollie’s revenue now comes from newsletter sponsors.
But the key to landing these sponsors is to build relationships before you pitch.
Feature relevant companies in your content, reach out afterward, and explore potential partnerships.
This way, sponsorship feels like collaboration, not a cold transaction.
Lesson 4: Growth = Recommendations + Remarkable Content
45% of Ollie’s subscribers came through Substack’s recommendation feature. But recommendations only work if your content is worth recommending.
Focus on quality, branding, and consistency first, then leverage partnerships to escape “creating in the void.”
Lesson 5: Think Like a Founder, Not Just a Creator
If your goal is to monetize, you need to move beyond “writing what you enjoy.”
Approach your Substack like a startup: own a niche, build a strong brand identity, and understand what your audience wants.
Long-term, that mindset turns a newsletter into a real media company.
