Smarter Solopreneurs

Smarter Solopreneurs

Smarter Strategy

Start With You

Then meet the market.

Maya Say's avatar
Maya Say
Dec 01, 2025
∙ Paid

Many of you are great at attracting engaged readers, but monetizing your email list feels like root canal surgery.

(Or worse. At least you get anesthesia for that.)

Igor Kheifets started from absolute zero, but his highly engaged email list now makes him thousands per month — and when it first took off, his list wasn’t even big.

The blueprint he developed for monetizing even tiny email lists is currently just $3.99.

It’s hard to find even basic email marketing education at that price.

Learn more & get your copy of the Click, Send, Earn e-book here.


We’re starting today by remembering two key things about strategic solopreneurs:

  1. We can achieve our goals. If thousands of other people can, we can.

  2. It takes time and it should. All good things do.

Take a breath. High-five me for being here: the newsletter designed to make you smarter about monetization and help you find your way to monetize.

Today, we’ll talk about which way to go: towards what you want to do or towards what the market demands.

Let’s dive in.


“What to sell?”

“The only art I’ll ever make is the art that I care about.”—Austin Kleon

“What to sell?” is one of the questions I get most often.

I work (and have worked) with a lot of very smart solopreneurs who struggle with this.

And despite being a solopreneur for 11+ years, I still ask myself this question whenever I hit a bump.

In the past 90 days, my newsletter growth pretty much stopped.

So I asked myself — again — am I selling the right thing? Do people even care?

And to answer that question…


I did something I never thought I’d do.

I created a spreadsheet.

A spreadsheet. Of all things holy.

This matters to you because it helped me discover something I’d forgotten, and something too many solopreneurs never really learn.

Here’s a part of my spreadsheet of 200+ Substack posts with summaries of each, their topics, and their results (likes, comments, shares, free subs, paid subs).

I must say, you’ll rarely hear me recommend spreadsheets, but this was one of the most useful things I’ve done since I started my newsletter.

I’m using the data in multiple ways, but one of the first things I wanted to check was:
What were the posts that got me the most paid subscribers? (And what specific offers I had in those posts, if any.)

So I took my top 5 monetizers and gave them to AI to analyze. Not just the topics and headlines, but the writing itself.

And to tell you the truth, the results surprised me.


All those posts were… me.

If there’s one piece of advice I find deeply annoying, it’s “be you.”

But there was something about these posts.

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