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

Meg Casebolt & Jessica Lackey
  • 4.9 (9)
  • TECHNOLOGY
  • UPDATED WEEKLY

In a world focused on more: more content, more followers, more marketing, more scale, more noise… we’re facing less trust, less contact, less reach. We’re drowning in AI-generated slop, being pitch-slapped by “personalized” email funnels that couldn’t be farther from authentic, and struggling to be seen by a pay-to-play algorithm. It’s never been easier to create and connect more cheaply and at more scale, with less trust and more skepticism. But for experts and service-based businesses? We’re seeing the pendulum swing back. The answer isn’t to play by these trends. It’s to be **aggressively human.** aggressivelyhuman.substack.com

  1. Has the "online course bubble" popped?

    6H AGO

    Has the "online course bubble" popped?

    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 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

    50 min
  2. The stories that get shared: Community-Forward Media with Lex Roman

    JAN 29

    The stories that get shared: Community-Forward Media with Lex Roman

    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 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

    52 min
  3. The expert's paradox

    JAN 22

    The expert's paradox

    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 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

    1 hr
  4. Goal-Setting: An Aggressively Human POV

    JAN 15

    Goal-Setting: An Aggressively Human POV

    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) 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

    54 min
  5. What makes communities work in real life with Raven O'Neal

    JAN 8

    What makes communities work in real life with Raven O'Neal

    (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

    50 min
  6. A tale of two book launches: Behind the Scenes with Amelia Hruby

    JAN 1

    A tale of two book launches: Behind the Scenes with Amelia Hruby

    Happy new year! For our first episode of 2026, we’re sharing the behind the scenes of two milestones from 2025. This episode originally appeared on the Off the Grid Clubhouse for paid subscribers, so we’re thrilled Amelia Hruby, PhD has shared this episode with us, so we could share it with you! Go behind the scenes of two book launches: Amelia’s Your Attention is Sacred Except on Social Media and Jessica’s Leaving the Casino. You’ll get two behind-the-scenes views into self-publishing, including super transparent numbers on our audience sizes and book sales. 👀 Amelia and Jessica had two different launch strategies (for two different types of books), so enjoy the contrasting approaches. We also get into pricing strategies, long-term marketing, and the messy feelings that come up when you can see who exactly has bought your book (and who has not). 😵‍💫 * 📖 BUY JESSICA’S BOOK: deeperfoundations.com/casino (or on Amazon, where the Kindle and Paperback edition came early!) * 📖 BUY AMELIA’S BOOK: offthegrid.fun/attention * Join the Interweb: https://offthegrid.fun/interweb 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

    46 min

  7. 12/18/2025

    What our bodies are actually telling us with Helen Tremethick

    In this episode, we talk with Helen Tremethick about the somatic experience of building and running a business. Helen shares how her work shifted from copywriting into regenerative business design, and how somatic education changed the way she thinks about change, responsibility, and client work. We spend time on the gray areas that don’t get talked about much: how to tell the difference between resistance and a real boundary, why not every hard thing is misalignment, and how we can navigate through uncomfortable stretches in our business. We get clear about scope of practice and why she didn’t turn somatics into a product. There’s also some aggressively human moments for Meg and mini-coaching for Jessica about how her body showed up to help make a decision about postponing a launch. * Helen’s evolution from copywriter to regenerative business designer * What somatic experiencing actually means * The difference between scope of practice, staying in our lane, and showing up as your whole self * Why not every discomfort is misalignment—and not every “no” is avoidance * How entrepreneurs confuse resistance, fear, and true boundaries * Why scope of practice matters when working with trauma-adjacent material * What it looks like to design a business that accounts for real bodies and real lives * How values, identity, and lived experience shape copy and marketing * Why “alignment” culture can quietly reproduce hustle and self-blame * The role of witnessing, mirroring, and permission in business decisions “You still need to to do lead gen, showing up and doing the thing. And, so if not LinkedIn, then what? So let’s say we find out that LinkedIn is not the good place for you. That’s okay. I may push it depending upon what your business is and who your people are and may push it and say, okay, let’s explore that. But let’s also explore other alternatives that feel less “Ugh.” So if you have this idea that LinkedIn is the way to go, but LinkedIn is so hard and therefore you’re not doing any marketing, let’s get you into posting somewhere else.” - Helen About our Guest Helen Tremethick Mentioned Episodes 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

    54 min

  8. 12/11/2025

    Do you *need* more strategy? Strategy versus Implementation

    Most people think they have a strategy problem. What they actually have is an implementation problem. In this episode, the two of us talk honestly about something we see over and over again—in our clients, in our businesses, and sometimes in ourselves: the difference between having a strategy and having the support to actually do the work. We both love a good plan, but we’ve watched plenty of perfectly sound strategies fall apart the moment they hit a real calendar, a real workload, or a real human with limited energy. Our conversation explores what strategy really gives you (direction, priorities, a sense of sequence) and what implementation requires (the skills to actually execute, time, and accountability). We compare strategy to a map: it shows where you want to go and the possible routes to get there. And we talk about the gap, when you need turn-by-turn directions, the recalculating voice when they get off track, and sometimes, the driver who can help get them moving again. The conversation ranges from client experiences with “strategy-only” offers to what it means to truly support implementation—through deadlines, accountability, and a bit of hands-on help when needed. * Why “strategy-only” offers often fail to create results * Jessica’s 28-point SEO plan story—and what it revealed about capacity vs. desire * How clients need different kinds of support: the map, the GPS, or the person doing the work * The “recalculating” role—why to choose a provider who will help you get back on course after a detour * Why overwhelm happens when the plan outpaces your emotional or practical capacity * Jessica’s existential “do I go hands on or not” dilemma * How deadlines, feedback, and accountability turn theory into momentum * Why AI can’t be your driver—it doesn’t check if you actually did the thing * The truth: strategy doesn’t scale without implementation rhythms and time management 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

    56 min
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In a world focused on more: more content, more followers, more marketing, more scale, more noise… we’re facing less trust, less contact, less reach. We’re drowning in AI-generated slop, being pitch-slapped by “personalized” email funnels that couldn’t be farther from authentic, and struggling to be seen by a pay-to-play algorithm. It’s never been easier to create and connect more cheaply and at more scale, with less trust and more skepticism. But for experts and service-based businesses? We’re seeing the pendulum swing back. The answer isn’t to play by these trends. It’s to be **aggressively human.** aggressivelyhuman.substack.com

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