The term ‘creator economy’ isn’t much without it. But you don’t start creating for money.

You start creating because you love it.

You don’t pick up a guitar for the first time and think about the music business. You just want to learn to play. You didn’t start shooting photos thinking about how you’d scale a photography business. You just wanted some pretty pictures.

Then one day you realize, “Wait, I could make real money doing this?”

I started writing a newsletter because I wanted to.

I never approached my newsletter (ie. creative passion) with business-oriented goals. I did that with a different passion project in 2019 and it went badly.

Instead, my only goal was to show up every week, write a newsletter about what I was interested in and what I thought would help you in your creator journey.

Then, after publishing for 6 months or so, I realized I could turn my love for writing a newsletter into a small business.

But — if I started over…

I’d reverse engineer a newsletter (or any content) for a quicker path to monetization. Instead of 6 months, I’d strategically build a media business.


Here are the most common:

  1. Advertising and/or sponsorships
  2. Paywalls or subscriptions
  3. Affiliate links/products

(This list isn’t exhaustive, but we’ll focus here.)

The most popular media business revenue play is still advertising. The Super Bowl is one long commercial with some football mixed in.

So building a media business in the form of a newsletter, YouTube channel, or podcast means keeping advertisers and sponsors in mind when creating content.

Reverse-engineering ads & sponsorships for content is simple — but it’s not easy.

Here’s one way to do it:

  1. Find a high-value/profitable customer segment (aka an audience that attracts advertisers like new moms or pug owners).
  2. Make a list of products or services those customers would be more likely to purchase.
  3. Curate & create relevant, high-quality content to grow your audience segment.
  4. As your audience grows, reach out to sponsors and advertisers with a media kit highlighting the demographic overlap in your audience & their customers. (Hint: you might already have a piece of content you can slip their product feature right into)

Something to keep in mind with this strategy: there’s a barbell effect with advertising.


  • A large audience with a wide-ranging demographic will attract advertisers as much as a highly-focused, niched down audience will.
  • Broad audiences need things like shampoo, food delivery, and banking apps; a highly-focused niche audience of pug owners will want things like Nose Butter and Wrinkle Paste (for the pugs, of course).
  • Here’s the key: while both might attract advertisers, one audience will need to be a lot bigger than the other to earn equal ad revenue (can you guess which one?)

Lenny Rachitsky has aced this strategy. His target market is mid-level product managers and it’s his expertise.

His paid newsletter drives subscriptions with gated content + a paid community. Lenny’s subscription works (over 95,000 subscribers — holy shit) because he…

  1. provides high-value content
  2. to a specific subset of professionals
  3. that will improve their careers.

Dan Shipper and Nathan Baschez started a paid newsletter bundle called Every. Where Lenny’s approach is targeted, Every aims to bundle a basket of well-written, high-quality paid newsletters — all at one monthly price.

Executing a paywall or subscription strategy without a near-expert level of subject matter knowledge — OR being wildly entertaining — is going to be hard.

People will pay to learn and they’ll pay to be entertained.

How you can reverse-engineer this:

  1. Research popular paywalled content and why people are paying for it.
  2. Choose a category you can execute on.
  3. Create the high-value content yourself — OR — curate it in the form of interviews, podcasts, or guest posts (think MasterClass).

TIP: If you can justify a business to pay for your subscription… 🤑

Another idea 💡: paywall an experiment where the process and results are valuable to a group of people.

This could be as simple as a new product launch strategy or software demo. You may have to start this with small, free experiments to build a groundswell.

Nick Loper at Side Hustle Nation has built a solid business on affiliate sales with his podcast, newsletter, and blog. He knows his audience is existing and future small business operators who’ll need things like accounting software, website hosting and freelance help.

Not-so-coincidentally, those are the types of products that sponsor his shows and he affiliates with.

These days, it’s rare to find a software tool that DOESN’T have an affiliate program. And SaaS isn’t your only affiliate option. More and more online courses and digital products offer affiliate options (see: Gumroad).

So how can you reverse-engineer your content for affiliates sales?

  1. Start creating (or curating) content for a focused audience interested in digital products, software and/or courses.
  2. Apply to become an affiliate for the courses and tools that make the most sense.


Now to really bolster your affiliate commissions, it helps if you actually know, understand and use the product or service. Get more sales with helpful webinars, testimonials, tutorials or demos of the product.

So many smaller SaaS companies are itching to get their products seen. Try reaching out to them asking them if you could do a joint demo or webinar.

If you’re too shy or don’t get a response, just create a tutorial. Marie Poulin became known for Notion because she dove into the product and created helpful tutorials on YouTube — for free — until Notion reached out to HER.

There is a lot more that goes into an affiliate strategy, as there are with all of these topics I’ve listed. But the crux of the strategy is simple: affiliate with products & services your know and use that would benefit 1,000 people like you — and share them genuinely!

Word of caution: if you affiliate and promote every product you can get your hands on, you will erode trust and credibility. Be selective, intentional, and strategic.


Creative pursuits are supposed to be about joy, passion, fulfillment and interest.

Figuring out a way to monetize them is an added bonus.

But making a business out of creating content? The strategies listed above are going to be a quicker path to income.