Deeper Business

Build your business - and your business-building intuition with foundational frameworks and practical application.

Oct 12 • 4 min read

Why I (accidentally) became a Double Lifetime Legend


Business media right now is a mess.

Forbes is pay-to-play. So is Entrepreneur Magazine. TechCrunch, Inc, Fast Company. Most of what you're reading isn't journalism; it's a sales funnel dressed up as advice.

And when platforms like Substack—a "writer's platform" at first glance—start rolling out policies that undercut the very creators they claim to support, who's going to call it out? Not the people who depend on staying in Substack's good graces. Not the people selling you courses on "Substack growth hacks."

Enter: Lex Roman and Revenue Rulebreaker.

Lex is a newsletter writer and Revenue Rulebreaker is the product: some of my favorite analysis of what works in indie businesses.

Not to harp too much on Substack, but while everyone else was praising Substack as the answer for independent media voices, Lex broke down why it's a bad fit and what tools support better monetization strategies instead. And I love Lex's behind-the-scenes breakdowns of what it takes to grow a business on subscription and sponsorship revenue—not the fantasy version, the real numbers and real work.

Revenue Rulebreaker is fun, but it's also deeply practical. Stories from entrepreneurs doing the kinds of things you want to be doing. "How to" guides you can actually follow.

I'm such a believer that I accidentally became a "Double Lifetime Legend" (I bought lifetime access to Revenue Rulebreaker then bought it again when the membership expanded). You know how much I value thinkers who challenge me and tell the truth—Lex is one of them.

Here's what you get with Revenue Rulebreaker:

  • Real talk on the ups and downs of business ownership
  • How specific revenue streams work (not theory—reality)
  • Revenue breakdowns that give you enough information to make good decisions about your own direction
  • A network of creators who value substance over algorithms (aka the Legends)

The newsletter is free, but the most valuable stuff—the guides and breakdowns you can follow, the mixers and connections—is behind the paywall for Legends at $9/month or $99/year.

And it works. Readers have booked clients, sold classes, won over paid subscribers, and booked sponsorships just from applying what's in the posts behind the paywall.

The reality about unbiased media and independent creators

Independence only exists when we pay for it directly. The minute media depends on ads, platform payouts, or large sponsors, it stops serving you and starts serving whoever's writing the checks. That's how business media became disguised marketing. That's why social media platforms are becoming wastelands of AI slop and rage bait—they're optimizing for advertisers, not for us.

If you want analysis that's useful, if you want content curated by a human who cares, if you want to connect with other people who value deeper analysis and connection—you have to support it with your wallet. When we fund the voices we believe in, we shape a more honest, human internet.

Start with the free newsletter, then upgrade when you see what (and who!) is behind the paywall.

Leaving the Casino Update!

Speaking of supporting independent creators, all existing orders of Leaving the Casino have now been shipped. You can order your books, immediately get a downloadable PDF, and (in the US), the physical copies will ship out to you in 1-2 business days!

NEW EPISODES

How to navigate the cycles of creativity without blowing up your business with Megan Dowd

In this episode, Megan Dowd joins Aggressively Human to talk about what it actually looks like to build a business that respects your creative cycles—and what happens when you don’t. From the pressure to always be visible to the collapse that can follow, we explore what it’s like to build a business while also being a human with a nervous system.

We talk about the performance trap of “consistent content,” what to do when you’re no longer interested in your own work, and how to use data and systems to support you.

UPCOMING EVENTS

Each month we'll discuss a chapter in my upcoming book, Leaving the Casino: Stop betting on tactics and start building a business that works.

Each dialogue is 12-1pm ET.

Get your book to read the accompanying chapter.

October 22: The Responsibility You Carry

November 19: What is Enough?

(No Dialogue in December)

Community and Reads

Big companies can test hundreds of subject lines a week.

Small creative business owners? We’ve got each other. 💛

That’s why I’m so excited to be part of The Great Subject Line Experiment of 2025!

Nicole Cloutier brought together 28 creators to share real data from our email lists (282 subject lines total) to see what’s actually getting opened right now.

The results are fascinating: patterns across tone, structure, curiosity, even emoji use. But what I love most is how collaborative it feels — a collective experiment to help all of us write more openable emails before the holiday season hits (when it’ll be extra important to stand out in the inbox).

Swipe these subject lines 👀


The Last Days of Social Media

Scroll further and recycled TikTok clips with “original audio” bleed into Reels on Facebook and Instagram; AI‑stitched football highlights showcase players’ limbs bending like marionettes. Refresh once more, and the woman who enjoys your snaps of sushi rolls has seemingly spawned five clones.
Whatever remains of genuine, human content is increasingly sidelined by algorithmic prioritization, receiving fewer interactions than the engineered content and AI slop optimized solely for clicks.
These are the last days of social media as we know it.

Jessica Lackey

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Build your business - and your business-building intuition with foundational frameworks and practical application.


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