Meet the new Revenue Rulebreaker

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Last updated: September 20, 2025

I can't believe I'm launching a blog in 2025.

Last year, I said blogs were dead. I thought newsletters killed them. But I was wrong.

Revenue Rulebreaker started because I shut down my membership and my podcast and was trying to figure out what was next. I knew I wanted to be a creator—meaning that I wanted to write, make tools and host events—but I couldn't see yet how I was gonna do that yet full time. So I started writing about what I was wrestling with in a newsletter that went to a few people I already knew.

And then, to my own surprise, I launched a new community to those people. What's now Legends.

Even more surprisingly, people said yes.

All the sudden, I had a new subscription business. My creator path became clear. Build an audience-backed media business. Maybe find a sponsor or two who sees the value in what we're doing here. Keep speaking and teaching as I go.

I was starting to see how these three revenue streams—subscriptions, sponsorships and speaking—could come together and provide enough income to do this full time.

The reason this website is called Revenue Rulebreaker is because people kept telling me I'm doing things the wrong way:

• You don't have a big enough audience to be audience supported.
• Audience subscriptions is never going to work full time.
• You're not going to get good rates from sponsors until you're bigger.
• No one cares what you're doing because you're too small.
• You can't make a creator career with less than 10,000 followers.

But I keep finding that none of this is true. You can do these things and people do care. So much of building an internet business is really up to you, and if you position things as valuable to the right people, they will join you for the ride.

So, what does the future for Revenue Rulebreaker look like?

This is morphing from a secret solo newsletter to a media company that produces stories and events about how people really make money online.

We talk a lot about how media is dying and collapsing and that's true of business media too. Forbes, Entrepreneur, Inc, Fast Company, TechCrunch and others are shells of their former selves. They've faced huge layoffs and, for at least Forbes and Entrepreneur, they want writers to pay them to publish work there. Who does that? Fancy business people who want backlinks to their company website.

It's a weird scene. And let's be honest. It never really included us anyway.

I've been an entrepreneur for 6 years and I've tried (nearly) every revenue stream and business model under the sun from memberships and digital products to services and sponsorships. But where can you find honest stories about that? Reliable information that helps you decide which path to pursue? Actual entrepreneurs who've been there and can tell you what they know?

You can't really!!! Because everything that's not pay to play is a funnel for getting sold the solution to all your problems.

Revenue Rulebreaker already covers:

• Memberships and subscriptions: How to run a recurring revenue business and what the difference is between subscription and membership
• Digital products: What it takes to sell digital info products and how to actually do it
• Newsletter businesses: How to grow and monetize an audience through email
• Sponsorships: Where to find sponsors and how to book them
• Finding clients: Where to find clients and how to book them
• The dirtbag lifestyle: My own chosen lifestyle and how work/life go together

I also want it to cover:

• Books and ebooks: Whether or not books can be a revenue stream and how to make them one
• Events and conferences: How to sell events and how to organize conferences
• Group programs: When to offer something at scale and how to deliver on a group experience
• Licensing your IP: Making money by licensing your work to others
• More tools: The tools that power any of the above revenue streams
• More lifestyles: Different ways to live your life and run a business

Right now, my vision for this is pretty broad. How do people make a living online, not as a software company? And I'm focused on people, not huge corporations. People like me. People like you. Maybe some of us have small teams but none of us is a 100 person operation. If you run one of those, this isn't your internet home.

I love experimenting with ways to make money and I love hearing how others are doing it too, but I steer clear of the "How I made $300k in an hour" type of people. I think those people are either outliers or full of shit and neither way is that interesting for us.

I like to cover people whose wins are hard won. They took an unexpected path or made a truly creative choice and it worked FOR THEM and there's something you could learn from their story too.

Here's a few of the stories that exemplify what this direction might look like:

• Why didn't anyone take me up on this!?
• How I got my first paid speaking gigs
• How I book partnerships now
• Why I changed my pricing (and went so much lower)
• Some of my audience growth channels, as someone bad at social media

I say "might" because I'm keen to bring in some contributors and expand how I'm thinking about what this place could be. I look forward to shaping it with you.

As I write this, most of RevenueRulebreaker.com is behind a paywall, but you can find the free stuff under the "free posts" tag.

Get on the newsletter if you want to keep up with what we're doing and if you want to meet the people who make this all possible, join us as a Legend. So far, 150+ people have trusted me enough to be part of this crazy dream and I build everything for them.

Overall, it seems to me that the signal is pretty damn good. So we're going to keep going.