What Million-Dollar Deals Closing Taught Me About Selling a Paid Newsletter
Everyone Talks About Writing Well — No One Teaches How to Sell. So I Did.

I negotiate million-dollar deals in my 9–5.
Boardroom. Suits. Pitches. Real money on the table. Big money.
I love my job.
But I still started a Substack.
Not to quit my job. But to share what no one else was talking about how the heck to actually sell your writing.
Because I saw most Substack advice skips that part entirely.
Most creators think if they just write well enough, the sales will roll in.
Or they copy other newsletters and hope that works.
But here’s the uncomfortable truth: They’re not skipping the sales part because it’s some secret. They’re skipping it because most of them simply don’t know how.
You’ll see them learning how to do it in public. Sharing their experience and that’s how they grow. When in reality it’s a trial and error.
They just simply don’t know how to sell.
I do.
Because I do it for a living.
And when I applied boardroom-tested sales psychology to my little corner of Substack? It worked.
I turned a newsletter into a real business with a 6% paid conversion rate.
(That’s double the platform average.)
And I did it without fancy funnels, upsells, or “engagement hacks.”
Just real offers, real trust, and yes: real sales conversations.
Here’s what they don’t tell you about selling on Substack:
Writing value isn’t enough. You need a conversion system. Answer those questions first: What are they buying? Why now? What changes for them if they don’t? Figure what are your audience’s struggles and build offers around that.
Most newsletters sound the same. Your paid offer must be polished: if it doesn’t stand out, it doesn’t sell. I always make fun of people who try to copy my ideas and present (and even sell) them as their own. It’s kind of flattering. But also sad…because I know they will fail. Your experience and who you are — that’s your edge. That’s what people can’t replicate.
Substack is not a blog.
It’s a relationship channel. If you treat it like Medium, you’ll get…
Medium results. Nobody’s subscribing because your post is “3000 words and research-backed.” They pay to feel seen, understood, and led. They pay you, not your newsletter. You’s content sells itself only when you design it to do so.
So what do I do differently?
Instead of writing at my readers, I sell for them. To help them solve their painful problems.
I use tested objection-handling tactics.
I treat every post like a boardroom negotiation table.
I don’t just build “value,” I build urgency and I stack reasons to buy.
The result?
A paid newsletter that didn’t just grow — it outperforms in conversion rates.
I don’t share fluff.
I share what works: from boardroom to inbox.
And if you want in?
You know where to find me.
Stay Unplugged!
Yana
P.S. If you’re curious about how to sell without selling, take a look at my Write2Sell column dedicated on solving this.
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