"Do the Opposite" Newsletter

Feeling a bit down - lost my first and only subscriber today.

Trying to find more ways to monetize the newsletter and provide people with more value to make it worth to subscribe to the paid layer.

If you have any advice & recommendations on how to improve the newsletter (format, messaging, strategy, etc.) I would love to hear your feedback! 🙏

This has been a long journey! When I first started the newsletter, and for more than a year after, there was no option of payment there as I haven't considered it at the time.

Initially I was using TinyLetter platform that didn't allow payments. This year, I think around February I've switched to Substack that has an ability to configure a premium paid layer of subscriptions which I did.

I announced that now there's a way to financially support DTO in one of the letters I've sent out - and hoped to get at least 3-4 paid subscribers out of the 1000 or so I had at the time. Nobody upgraded their subscription at that time :)

For now I'm making a point that a paid layer being similar to Patreon - just a way to support the newsletter and I want to put the money received into promotion/advertising of the newsletter, maybe doing book giveaways on Twitter and such. Later I hope to add more benefits for paid subscribers to provide more reasons to upgrade.

This milestone took a while to hit but I'm very happy I got to this point! :)

Over time I've gotten much better at finding the right content and writing consistently, but I'm still very unsure of how to properly market the newsletter and let more people know about it!

Got to this first big milestone! It took me a while, but it was the greatest feeling to know that the stuff that I write is actually interesting and useful to people.

Knowing that gives me more motivation to continue writing! I hope the next milestones come faster as I get better at promoting the newsletter and just letting people know it exists!

I had ideas about writing a newsletter in this format going back to 2015. In fact I wrote one issue that year and sent it out!

Unfortunately at the time I didn't have enough self-discipline and motivation to commit to writing consistently. It would take me 4(!) more years to get to that point.

From this day on I've never skipped a newsletter and I always send it on time. When started, for more than a year it was a weekly newsletter, but this year (in 2020) I've changed it to be bi-weekly)