Monetizing a newsletter is hard.

That’s not a secret.

I sent my newsletter for nearly two years and 100+ editions before making a single dollar from it.

I was quickly sold out of ad inventory for months at a time. This sounds great, right?

Wrong (kind of).

I was capped at $1,000 - $2,000 per month from primary ad revenue simply based on the size of my audience and reasonable CPM that I could charge.

After re-acquiring Workspaces and trying to get the sponsorship flywheel humming again, I realized two things.

1) The newsletter was now ~12,000 subscribers and I had never experimented with “classified ads”

2) The website itself was receiving anywhere from 50,000 - 75,000 pageviews per month — a potential revenue stream that I had overlooked

So on October 24, 2024 I decided to try a quick experiment.

I would introduce a new “Supporter Tier” that would tackle both of the points above. I would introduce a classified ad tier while also attempting to monetize the website in a way that felt natural to what I had built over the last 4 years (no Google Adsense 🙅‍♂️).

If it flopped I could simply delete the tweet and move on.

Instead, these slots sold out in 11 minutes and had $1,000 added to the super official Workspaces, LLC bank account.

Replies and DMs were still rolling in with interested people and brands so I quickly stated a waitlist that immediately grew to 16 more people.

An additional revenue stream was officially rolling thanks to these four sponsors.

Throughout the month they would receive >2,000 clicks.

The Supporter Tier was working!

Since this kicked off, Supporters have now seen nearly 7,000 clicks come their way.

And yes… I did raise the prices for the next batch of supporters.

And now to state the obvious… while this single tweet did technically lead to $1,000 in ad sales in just 11 minutes, the ability to do this actually took 4+ years and thousands of tweets to build the following that made this possible.

There were no shortcuts.

Interested in seeing your logo as a Supporter? Just hit reply and let me know!

Whenever I’m asked how long it takes to run a newsletter like Workspaces I always respond with “I don’t know probably an hour or two each week?”

This week I’m going to time every single thing Workspaces-related so that I have a real answer.

I’ll share the breakdown next Sunday.

Stick around.

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