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

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 RomanAbout our GuestRevenue RulebreakerBecome a LegendLex Roman on LinkedInMentioned ResourcesCal Newport - Can Substack Save Journalism?AntimemeticsConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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.” - MegThe Expert’s Paradox by Meg CaseboltA Clarion Call for Expertise by Corey WilksConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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 yearResourcesJessica’s 4 Part Planning SeriesMeg’s Consistency Beats Virality (even When You Go Viral)Connect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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 GuestLinkedInSavvy Gal MediaHacking the Patriarchy PodcastFem Led NewsConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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

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/interwebConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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 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.” - HelenAbout our GuestHelen TremethickMentioned EpisodesConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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

Many believe they struggle with strategy when, in fact, it's implementation that's the issue. A well-crafted plan can flop without the right support. The hosts share insights on why solely handing over strategies often leads to frustration. They draw an analogy between strategies and maps, emphasizing the need for GPS-like guidance. Check-ins, hands-on assistance, and tailored implementations are crucial for success. They also highlight the limitations of AI in execution and the importance of managing time to avoid overwhelm.

It’s the one-year anniversary of Aggressively Human! In this milestone episode, we look back at the first fifty-two episodes of the show—what surprised us, how the podcast has performed (and what does performance even mean?), and how podcasting has shaped both our friendship and our businesses.We talk about what makes co-hosting work: shared accountability, complementary energy cycles, and overlapping but distinct guest networks. We talk about how the Aggressively Human podcast served our business goals that we set out for a year ago. We share the behind-the-scenes lessons of running a human-centered podcast—everything from scheduling and editing to scouting guests and showing up with curiosity and authenticity.The conversation also explores how both of our businesses have evolved over the past year—Jessica closing out her first five-year arc with Leaving the Casino and Meg deepening her work in AIO, and how we’re thinking about AI, automations, and algorithms today in 2025.* What makes a co-hosted podcast sustainable for a full year* How mutual accountability keeps the rhythm (even when energy dips)* The hidden work behind guest curation, editing, and show notes* Why we feel more energized after an hour podcast than a 15 minute YouTube* Why we avoid “pitch-me” guests and only invite people they know or admire* What we’ve learned about informal promotion, reciprocity, and trust* How podcasting has strengthened our friendship and creative shorthand* What’s changed in both of our businesses since the show began* How automation and AI can serve memory, not replace humanity* What year two will explore: ethics, curiosity, and using the tools without being used by them“Now that we know what the tools are, we’re seeing what’s starting to be possible, how are we looking at curious ways to bring it into our business models to use these tools, not at arm’s length, but to say, these have a place in the tool belt.” - JessicaConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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 our first US Thanksgiving episode!And while many podcasts are paused today, we wanted to bring some Aggressively Human to you while you’re cooking, carving, or just getting out of the house in between football games.We want to say thank you to our listeners. Thank you to anyone that has rated the podcast on your preferred podcast player! Thank you to our commenters, the ones who tell us what they loved or have questions about in the episodes. Thank you to our guests, who make time to come hang with us and showcase what’s aggressively human in your lives and businesses.And, from Jessica and Meg to each other, hear us say thank you to our co-host.It’s so much more fun with friends.Plus, hear a fun fact about when each of us met our husbands!Ok - now go back and finish eating pie, if that’s on the to-do list for today.(P.S. - my favorite is pecan, I am from the mid-atlantic. Meg’s favorite is pumpkin).Connect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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

Nick Bennett and Erica Schneider, co-founders of Duo Consulting, share their journey from course creators to advocates for high-touch service models. They discuss the importance of tailoring offers to recurring client problems, contrasting retainers and one-off projects. The duo emphasizes 'selling like a human' by avoiding cookie-cutter sales tactics. They dive into the myth that services can't scale and argue that burnout stems from low-impact tasks rather than workloads. Their compelling insights reframe how we think about client success and sustainable business practices.