Revenue Rulebreaker is not even two years old yet and it's led many lives already.
Chalk it up to my personal flavor of mental illness, the force feeding of AI or just being an early stage publication, but we're altering our course to better serve you. Again.
I've been working with journalist and Legend James Cave on clarifying our editorial voice and focus. For at least the last year, the core theme of Revenue Rulebreaker has been how solopreneurs make money. That's still a broad scope though so allow me to define more clearly what we plan to cover this year.
I say "this year" because I know myself well enough to know nothing stays the same forever in my brain and I can't promise you much beyond the next few months. Especially until we try this on for size.
Revenue Rulebreaker (RRB) features the stories of struggle, vulnerability and triumph of building something that is uniquely yours. As our name suggests, our stories are nearly always about revenue and how you generate it. I am really starting to hate the "I made $200k in 5 minutes doing this one thing" format that's common in both the startup and small business world, so while I do want us to share real numbers, I don't want RRB to be gimmicky and out of reach.
Who writes Revenue Rulebreaker
I am still the primary writer behind Revenue Rulebreaker and I plan for that to remain the case even with the inclusion of guest contributors.
Last November, we started taking on guest contributors and, to date, we've had 22 guest writers share their work with us here. Accepting guest contributors has been a massive learning curve for me. When submissions are open, we get flooded with so much garbage, it's hard to spot anything worthwhile. I've had to pull a couple contributions last minute because the writer either misrepresented who they were or they couldn't come up with a publishable draft. On the flip side, we've had a couple super meaningful stories from guest writers that have changed the course of some of our businesses. I still very much believe in the value of us hearing from other entrepreneur-writers but we need both a more stable budget and a more consistent set of contributors. I am paving the way for that now by working on stabilizing subscription and sponsorship revenue and by crafting columns with some of these guest writers in mind.
I am hoping to be able to take guest writers again by end of this Summer (August 2026) but I will most likely recruit those writers myself. And yes, I know we need an editor. I fucking hate being the editor but I can't afford one yet. That's a big goal for next year.
What we cover
Last year, I wrote that I wanted to widen the revenue streams we're covering more regularly. I've changed my mind about that.
We are going to cover the following topics regularly:
- Growing your audience (Now That's What I call Growth)
- Finding your repeatable business model (Buried Treasure)
- Getting clients (Low Energy Leads)
- Building a membership or subscription (Recurring Revenue)
- Work and life styles of solopreneurs (Work Styles)
- Counter takes on the same old marketing bullshit we're all sick of (Thanks, I Hate It)
- Hot topics in the small business world and what we think about them (You Might Have Missed)
We are also experimenting with two new columns:
- Marketing and monetizing books (Page Earner)
- Ask The Legends for advice (Ask The Legends)
Books have become a surprisingly prevalent theme among Rulebreaker readers, hence prioritizing author marketing over something like digital products or sponsorships. We will still do some coverage of digital products, sponsorships and other ways we're making money, but our priority revenue streams are client services, recurring revenue models, and books. For now.
Ask The Legends just launched a few days ago and it is currently slated to end on June 9th but so far, I'm pretty impressed with the questions and answers coming in and think that this has legs as a standing column Legends contribute to via comments and then, are featured in the newsletter. I could also see a single Legend contributing as a paid guest writer a more longform answer to some of these questions.
You can still find topics beyond these on our Topics page and we will occasionally publish outside these bounds when it feels important or urgent to do so.
Newsletter businesses will be covered more by our sister publication paidnewsletterplaybook.com, which all paid subscribers have access to and which I still write myself.
How we cover it
The stories that get the most response, shares and new subscribers are always the most inflammatory ones. I wish it was different but that's just not the internet we are living under in 2026.
Revenue Rulebreaker will continue to be a service publication that offers stories you can act on but we will be pushing on the norms more frequently. You can expect Rulebreaker to get even more voicey, even more controversial and even more offensive. Never in a racist, misogynistic or homophobic way. More in a NSFW or a NSFC (not safe for conferences) way. I know a few of you were taken aback by my use of the phrase "whoring yourself out" in a business context recently. There's more where that came from. Brace yourselves.
As for contributors, I'm looking for this same boundary pushing. We're not trying to be brash for the sake of it, but we're spilling our guts like we would at hour 5 of a dinner party sitting next to people we really like and want to see succeed.
Where this is all heading
Like I said, we're heading towards our 2nd anniversary this October and I want us to keep being able to celebrate those milestones. The bigger we get, the less paid subscribers are here for the publication side and the more it becomes about the community features. I need to re-balance that.
I purposely chose for Revenue Rulebreaker to be community-centric but the publishing side should be at least be 50% of the value of being a paid subscriber. Otherwise, the publication has less investment and less reason to exist. Legends certainly could exist on its own and that's one possible future, but it's a future I'm personally a lot less excited about.
This new editorial direction should entice more investment and interest in the publication itself. That is my goal.
We are now at 355 Legends. By the end of 2026, we need to be at 500. I want to attract at least some of those people to join us with our stories.
How to give your input on our direction
I will be running a reader survey in June to get your input on this and other parts of this project, including events and Legends' perks. I will also be opening up another set of Legends 1:1 in a few months so we can talk more in depth.
Other than that, you can comment or reply to stories and let me know what resonated with you or you can share topics you hope we will cover. That's always a huge help to calibrate what we work on.
Thank you for joining me on this wild ride to birth and raise an independent small business publication at the worst possible time to do that. The fact that you're even still reading this post gives me hope that we can keep going.
Want insight into the health of the business side? Read our yearly and quarterly reports and join me for Quarterly Earnings Calls.
