👋 Hi Reader,

There is one question I keep hearing from new newsletter operators I talk to, across the globe.

When do I start monetizing?

And I never had a crisper answer, than what Tom Alder put in his post on LinkedIn recently.

I admire Tom’s consistency in building Strategy Breakdowns and I follow his journey closely. I also devoured the entire onboarding breakdown about Strategy Breakdowns (I know, very meta) that Chenell Basilio from Growth In Reverse had published a while ago.

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But one line from his LinkedIn post helped me articulate what I have always been struggling to put succinctly.

This statement coupled with Tom’s post on X on his journey about making money online makes sense, when you look at them together over what he has achieved over a protracted period of time. Why? Because Tom never skipped the value step while publishing Strategy Breakdowns.

Tom Alder @tomaldertweets i made $42,441 in march 2026 ✏️ sponsorships - $40k 📚 digital products - $2.4k + hired a weapon part-timer to ship more automations / ai + crushed 3 campaigns → closed renewals for all 3 but... - my assistant of 2 years resigned, so looking for her replacement - aug-dec '25 11:42 AM • Apr 1, 2026 0 Retweets 37 Likes Read 14 replies

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And that brings me back to last week's issue

When Gmail starts summarizing your newsletter before your reader ever sees it, your open rate can tank (not that you should be looking at open rates in the first place anyway in 2026)

But here’s what does not tank (yet): the attention of a reader who finds your newsletter essential to their way of life.

If your content is delivering enough value that your subscriber feels the summary is not enough, that they have to read the original to get the full picture, that’s when you realize you have valuable content to share, which might be worth monetizing.

From that point onward, you do not need to wait for a magic subscriber number to add sponsors or collaborators.

If I were in your shoes and thinking about the monetization question, the 3-step approach would be: Build value publicly. Let attention accumulate. Then monetization becomes a natural progression, rather than a forced one.

Need a sounding board in understanding the right point for monetizing your newsletter? I would love to talk to you.

Let me know by hitting ‘Reply’ on this email, or send a note to marketing@letterstack.co.

This newsletter is sponsored by The Alien Design

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Cheers,

Renga from LetterStack

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