It's crazy that anyone lets me run this business. It's both the best job I've ever had and the most uncertain venture I've ever pursued. Many days, this project feels like it's just floating along on soft clouds powered by your kind words. Fragile, volatile and beautiful at the same time.
This is why I'm ruthlessly blocking my haters on LinkedIn.
That said—Revenue Rulebreaker had a good first quarter. The business is getting stronger and I'm getting smarter about how I want to run it.
We had some notable successes like crossing 250 Legends (the halfway point to my ultimate goal) and launching The Legends Directory. And we had some big misses like when I asked you to pitch me parenting entrepreneurship stories, and then, readers said they actually weren't interested in that and all the pitches started to sound the same to me. I am sorry about this misguided ask. I really love publishing guest contributions and I am excruciatingly bad at it. LESSONS ARE BEING LEARNED.
Beyond the day to day, I want you to know where your money is going and where this project is heading. So I'm reporting back every quarter on how the business is doing. This is the first of those reports: Q1 of 2026. I am holding a live earnings call on Thursday, April 9th to walk you through this and take your feedback and questions about it. If you're reading this after April 9th, RSVP and it will send you the recording.
Q1 was pretty great. Q2 is shaping up to be rockier. Read on, Rulebreaker!
Sections
- Biggest lessons
- Q1 2026 Goal targets vs reality
- What we did together this quarter
- Community success stories
- Successful and failed projects
- Growth channels that worked
- Revenue and expenses
- What to expect in Q2
💡Biggest lessons
The subscription system is working. The sponsorship system is not. We had a good Q1 because I set us up for success in Q4 with sponsorships. Sponsorships are one of our two main revenue streams but we don't have any booked for Q2 (and we should). I pitched the wrong sponsors in January and February which highlighted a major flaw in my cross-channel campaign strategy. I can only really work with one partner at a time if I do full channel takeovers. That limits who I pitch because if I think something's coming in, I try to close it instead of pitching wider. You'll see below that my approach is changing because we have to get this back on track while we build up reader revenue. I get excellent results for sponsors. We should be fully booked.
My core audience is creative service providers and membership operators. After a two year detour into journalism, I'm back with my core audience of designers, marketers, operations and business consultants. The Rulebreaker appeal is somewhat wide but the people who come with me project to project, event to event, subscription to subscription, they are creatives and tech consultants not publishers or creators. As much as I enjoy the media revenue models and teaching it, it's a smaller segment within my bigger audience. I need to stay focused on the people who show up repeatedly and pay me and that's creative professionals. There's a tiny loophole here which is creatives who are becoming media entrepreneurs and I'm paying attention to how I can help them make that transition too.
Readers love Rulebreaker for its voicey stories that go against what others are practicing. I got a lot of feedback during my Legend one on ones that people love the more controversial pieces we published. I see this in analytics too. My post on how Substack steals your audience, the story on leaving social, Jamie's story on shutting down her creative collective and Kaitlyn's story on starting to paywall are by far the most trafficked stories of the last few months. The girlboss email I sent last week (which was actually just a promotion I ran for Tarzan Kay) got the most replies in months. I need to surface more of these stories that take a strong counter-perspective on well-worn business practices.
Legends value different things about their paid subscription. The kryptonite of this business is that everyone's here for a different reason. I did 21 chats with Legends during this season and I heard 21 different reasons Legends joined or stayed. Legends are prioritizing a wide range of things from launching a course to publishing a book to deciding between a potential new job and their business. I'm going to have to pick some lanes here about who we're serving best because trying to serve everyone serves no one. We need a tighter editorial and events strategy to grow this thing past where we are and that means narrowing the focus.
🥅 Q1 2026 Goal targets vs reality
Revenue Rulebreaker's core revenue streams are subscriptions and sponsorships. Here's how they performed in Q1.
Come along for the ride!
Revenue Rulebreaker is a member-supported publication. You wouldn't think a shitty writer like me could do that but turns out I can. Get in on this fun parade when you become a Legend.
Legends get:
- All access to everything I post
- Special invites and events
- Recognition on The List of Legends
Become a member
