Aggressively Human: Online Business in the Age of AI, Algorithms & Automations

Lately, a lot of well-known course creators have closed their flagship programs or shut down their podcasts. Other online course creators who will “never again sell live training”…. well, they’re back with live training.
Is the course bubble over? Will AI shut down courses? Or is this just an industry hot take to get clicks and views?
In this episode, we talk about what’s actually happening with courses right now—and what’s not. We look at why self-guided, evergreen courses worked for so long, why they’re struggling to convert and retain attention now, and how AI has sped up changes that were already underway. We talk about how this has shown up in the various evolutions of our own businesses. We also talk about where courses still make sense, where they don’t, and why people are increasingly unwilling to pay for information without context, support, or application. (A multimedia interactive experience as Jessica called it in corporate-speak).
This isn’t a declaration that courses are dead. It’s a conversation about saturation, economics, attention, and what people actually want help with in 2026.
* Why course closures are becoming more common
* The difference between a bubble bursting and a market maturing
* What made evergreen courses work in the first place
* How rising ad costs and shrinking arbitrage changed the math
* Why beginner-level education scaled—and why it hit a ceiling
* What AI replaced almost instantly (templates, boilerplate, generic content)
* How Meg and Jessica have both surfed the wave of courses, both as leaders and as students
* What people still pay for (and what they won’t)
* The problem with “lifetime access” promises
* Courses as one piece of a broader ecosystem, not the whole business
“If you have a giant course where you promise to do everything, then you can’t do all of it well. And I think people are getting a little bit tired of like the survey courses, like the freshman 101 course of everything, or maybe those still exist. And I’m just out of the world view where I’m paying attention to them. But anytime that you have an all in one solution, whether that’s a course or a piece of software, or a coach who says that they can help you with everything, that breadth is going to prevent depth.
And if you want to learn something deeply from a person who understands it and can answer your questions when things go wrong, then that’s when you want to find an expert who teaches one thing really well instead of 10 things mediocre.” - Meg

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Meg Casebolt
Jessica Lackey


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

In this episode, we talk with Lex Roman, founder of Revenue Rulebreaker, about why solopreneurs and micro-business owners are almost invisible in mainstream business media—and what happens when someone actually builds a platform for them. Lex shares how Revenue Rulebreaker grew out of a personal experiment in becoming a full-time creator and turned into an independent media publication focused on indie businesses, real revenue experiments, and work that doesn’t fit the venture-scale mold.
We spend a lot of time on what’s broken in business media: pay-to-play outlets, thought leadership that’s really just a sales funnel, and the absence of honest stories about what it’s like to run a small, durable business. Lex explains why journalists aren’t filling that gap, why solo businesses have a hard time surfacing interesting angles, and why so much valuable knowledge stays trapped in private conversations instead of becoming public learning.
The conversation also gets practical. We talk about subscriptions versus memberships, why Revenue Rulebreaker is a media brand and what does that mean, and how sponsorships, subscriptions, and community-adjacent networks can coexist with (or sit alongside) client work. Underneath it all is a bigger question: what would business culture look like if we treated podcasts, newsletters, and blogs as media—not just marketing?
* How Revenue Rulebreaker started as a personal experiment and became an indie media publication
* Why solopreneurs and micro-business owners are ignored by mainstream business media
* The collapse of traditional journalism and what it means for business coverage
* Why pay-to-play outlets distort whose voices get amplified
* Why having an “angle” is how stories get platformed
* The difference between thought leadership, marketing content, and media
* The problem with content that always has to sell something
* Subscriptions vs. memberships—and why Lex is intentionally avoiding a membership model
* How sponsorships and subscriptions actually fund indie media
* Why private experiments inside small businesses are some of the most valuable stories we never see
* The role of community, networks, and stewarded spaces in a post-algorithm internet
“Journalists previously who would have been sourcing those stories don’t know a lot of business owners, but they know the woman who started Spanx.
So they’re just not that working that hard to find stories. So if they don’t know any business owners, and you don’t pitch them a compelling story, that story’s not getting told. I think also business owners have a really hard time understanding what’s cool and interesting about their own business.
Like, you know, they’re like, “I’d like to have my business platformed.” Of course you would, but you don’t have an angle? What’s your perspective? Why are you doing this interesting thing? You have to really dig at them to find those interesting things.” - Lex Roman

About our Guest
Revenue Rulebreaker
Become a Legend
Lex Roman on LinkedIn
Mentioned Resources
Cal Newport - Can Substack Save Journalism?
Antimemetics
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Meg Casebolt
Jessica Lackey



This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

The longer you’ve been doing your work, the harder it can be to explain it.
In this episode, we talk about what we’re calling the expert’s paradox: why people with real experience often struggle to publish clearly, while less-experienced voices seem perfectly comfortable shipping simple advice. We see the seven-part blog post that will take 21 hours to write, and know we can’t stop with the simple AI-generated “5 simple tips” framework. We look at how this shows up in content, marketing, and tool recommendations—and why experts tend to freeze once they can see all the nuance at the same time.
We talk about the Dunning–Kruger effect, the difference between tutorials and diagnostic thinking, and how to deal with the pressure to finish the entire framework before saying anything publicly. We also talk about what helps: publishing before things feel complete, letting ideas change in public, and using content as a working asset rather than a polished performance.
And hear Jessica use the question “what’s the best CRM” to map out a content strategy in real-time, and Meg and Jessica compare chemistry (we think?) to your content organization philosophy.
* Why having more experience often makes it harder to say anything short, clean, or publishable
* How we can use our content for reinforcement, not repurposing
* A Clarion Call for Expertise with “Zippie Nickie and Gnarled Bart” from Corey Wilks, Psy.D.
* Why experts feel pressure to finish the whole framework before sharing anything
* Why tutorials are easy to ship and diagnostics are slow (and why that matters)
* How publishing your work and getting your language out there changes what people search for
* Why clarity wins out over volume in 2026
* How you can use blogs and long-form content as living, updateable assets
* Content architecture: collections, pillars, and making old work findable again
* Our voice choice and how does that influence your authority
“If you have something interesting to say that you feel is different from what else is happening in your industry, that is not a sign that you are outside of the norm; that is a sign that you see something that the beginners don’t. But you cannot be cited, credited, claimed, unless you put it out into the public sphere for indexing, for retrieval, for somebody else reading it. And you can’t change the discourse if you’re not part of the discourse.” - Meg

The Expert’s Paradox by Meg Casebolt
A Clarion Call for Expertise by Corey Wilks
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Meg Casebolt
Jessica Lackey


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

It’s New Year, New You Time - which means it’s time for goal setting! (Cue the cheers and the groans).
But we have thoughts on traditional goal setting. In this conversation, we talk about how outcome based goals are often ineffective (and the fast path to burnout), and instead focusing on what’s in our locus of control.
We talk about the difference between “bottoms up” and “top down goals”, and how your stage of business and business model informs what matters. You’ll get to hear Jessica get on her soapbox about “10x is easier than 2x” goal setting, and hear us talk about how physics informs our approach to goals.
Plus hear OUR goals for 2026 — and most importantly, what we’re not doing this year.
* Why we both hate most New Year’s goal setting advice
* Outcome goals vs. output goals—and why the difference matters
* How goals fail when they ignore where you’re starting from
* Why revenue goals aren’t fully within your locus of control
* The problem with “just do more” as a strategy
* Force, leverage, and friction: three ways to change results
* How vanity metrics create performative productivity
* Saying no as an essential part of goal setting
* What we’re each choosing to focus on—and what we’re actively letting go of this year
Resources
Jessica’s 4 Part Planning Series
Meg’s Consistency Beats Virality (even When You Go Viral)
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Meg Casebolt
Jessica Lackey


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

(FYI - the last 10 minutes has more f bombs than usual if you’ve got kiddos with you).
Who doesn’t want to fit in to their local entrepreneurial communities—but how many communities miss the mark, especially for solopreneurs and expert-led businesses? We’re joined by Raven O’Neal, co-founder of Startup Women NC and founder of Savvy Gal Media, to talk about what actually keeps a community alive once the initial excitement wears off.
We talk about what Raven has learned building a local community: how most ecosystems are designed for scalable startups, not people selling expertise; why solopreneurs often don’t fit anywhere cleanly; and why “more members” often makes things worse, not better. What surprised Raven most wasn’t a lack of resources—it was how fragmented they are, how little they talk to each other, and how much invisible labor it takes to hold people together.
This conversation also names the uncomfortable truth underneath community-building, both IRL and online: it’s real work, often unpaid, and frequently taken for granted. We talk about the politics of funding, the myth that collaboration is easy, and why intimacy, continuity, and clear leadership matter more than growth.
* Why most “community” spaces collapse once they try to grow
* How startup ecosystems quietly exclude solopreneurs and expert-led businesses
* What Raven learned building Startup Women NC—and what surprised her most
* The difference between social mixers and real, sustaining community
* Why fragmentation (not scarcity) is the real problem in local ecosystems
* The unpaid labor required to organize, host, and maintain community spaces
* How Raven’s work on Hacking the Patriarchy informs her approach to power, labor, and voice
* Raven’s word of the year and how that’s informing her building plans (PS - It contains a lot of cursing)
We actually had a meeting where we asked what does growth look like for this group? And a lot of our members said, one thing I love is how small it is. Like how much smaller it is and how intimate our meetings are and how much attention they get and how they’ve gotten to know each other.

About our Guest
LinkedIn
Savvy Gal Media
Hacking the Patriarchy Podcast
Fem Led News
Connect with Us
Listen on Spotify
Listen on Apple Podcasts
Meg Casebolt
Jessica Lackey



This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com