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Aggressively Human: Online Business in the Age of AI, Algorithms & Automations
Aggressively Human: Online Business in the Age of AI, Algorithms & Automations
Author: Meg Casebolt & Jessica Lackey
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© Meg Casebolt
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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
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
60 Episodes
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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
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 managementConnect 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 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
What if the most human decision in your business is your offer structure?In this episode, Jessica and Meg are joined by Nick Bennett and Erica Schneider, the duo behind Duo Consulting, for a conversation about business models, burnout, and what’s really behind scale. They trace their journey from the course boom and “productized” advice back toward deeply human, high-touch service work—and the freedom that came with doing less, but better.They talk about what happens when you stop selling one-time solutions and solve recurring problems, how to rethink retainers, and why “selling like a human” is still the most powerful business strategy. The group also digs into the false hierarchy between consulting, coaching, and implementation—and how being hands-on can actually create more impact, more fulfillment, and better outcomes for clients.Tired of the “retainers” vs. “courses” vs. “productized services” debates on LinkedIn about the best business model? Learn how we’re all building the kind of business that fits our energy, our brains, and our lives.* Nick and Erica’s evolution from solo operators to partners at Duo Consulting* Why they retired their successful course and community in favor of 1:1 work* Why most “passive income” models still require constant marketing* How to match recurring problems with recurring offers* The debate between retainers, projects, and sprints—and why none are one-size-fits-all* How to sell like a human instead of hiding behind funnels and scripts* Why client success—not volume—is the real measure of scale* The false hierarchy between coaching, consulting, and done-for-you work* How standardization, automation, and selective delegation create sustainable growthThe reason we’re so passionate about helping our clients move to solving an ongoing problem is that in that retainer model you get to drag your clients to glory. Because then you can say, “look at all of this awesome success that my clients have working with me”. I would rather my clients work with five people a year and have those five people be massively successful than work with 50 people a year and have no clue or help them achieve nothing.” - Nick BennettAbout our GuestsDuo ConsultingNick BennettErica SchneiderHow Solos ScaleThe Recognition GapConnect 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
After years of focusing on podcasts, teaching, and newsletters, Meg just released her first blog in three years. In this episode, Meg and Jessica talk about why it’s time to come (back) to blogging—and why it matters more than ever in a world of shifting platforms and AI-driven search results.They share the practical and philosophical reasons behind the shift: protecting your intellectual property, proving you got there first, and creating a timestamped body of work that can be found, cited, and built upon. It’s how you build a business on rock instead of the sand of social media and shifting algorithms. From domain authority and discoverability to Substack cross-posting and AI parsing, they look at what it means to write for durability, not trends. They also explore how written assets double as onboarding tools, teaching material, and long-lasting content that can be reused across your ecosystem—bricks in a foundation that lasts.(Plus, hear Meg sing a song that totally relates!).* Why Meg is returning to blogging after three years focused on other platforms* The “sandy land” metaphor and what it means to build your house on a rock* How blogging establishes topical authority and protects your IP* Why timestamps matter: AI can’t cite a TikTok, but it can cite a post with a publication date* The danger of building on rented land (Substack, LinkedIn, social media)* How written work creates a paper trail for your thought leadership* Blogging as both visibility strategy and proof of ownership* How AI and search engines reward structured, linked, human-written content* Turning blog posts into reusable assets for onboarding and education* Why a durable body of work outlasts any short-form content trend“If you build your house on sand, you’ll have to build it twice.” - MegResourcesLove at First Search BlogConnect 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 platforms we built our businesses on are breaking down—and not by accident. In this episode, Jessica and Meg take on ensh*ttification, the term coined by Cory Doctorow to describe how digital platforms inevitably decay over time. From Facebook and LinkedIn to Substack and AI, they discuss the predictable four-phase cycle that turns once-useful tools into algorithmic wastelands.Book released October 2025Jessica walks through what that cycle looks like for LinkedIn and Substack, while Meg connects it to the decay of creative platforms like Medium and Kindle publishing. Together, they explore what creators and experts can do when every channel feels rigged—and what it means to build on digital “rented land.”It’s part diagnosis, part “what now”: a conversation about recognizing when the rules have changed, when to adjust your strategy, and how to build resilient foundations that outlast the next platform crash.* The origin of the term “enshittification” and how Cory Doctorow describes the four-stage cycle* What Facebook, LinkedIn, Twitter, and Substack teach us about platform decay* How AI tools are repeating the same subsidized-growth pattern as social media* The false nostalgia for “when it worked” and how fast cycles now move* What to do when the strategy you learned in phase one stops working in phase three* How to spot market arbitrage opportunities before they close* Why foundations, relationships, and your body of work are the only real insurance* How to keep your business discoverable without chasing every new trendAdditional ResourcesPodcast | The Gray AreaWhy is the Internet bad now? | Evan Armstrong/The LeverageConnect 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
While AI still can’t fold your laundry, it can help you build a business that runs smarter—and a life that runs smoother. In this episode, Jessica and Meg talk with Mary Williams, the librarian-turned-tech director behind Sensible Woo and the new Sasquatch Media Grounds studio in Portland. From haunted recording spaces and tarot cards to spreadsheets and AI bots, Mary shows what it looks like to blend intuition with technology.She shares how she built her “AI team”—including Remy, the snarky Gen Z assistant who filters her inbox and protects her calendar—and why she treats her chatbots like departments inside her business. They talk about how AI can help reduce emotional labor, from grocery budgets to health tracking, and what it means to build systems that keep the human at the center.This conversation is filled with practical ways to make AI feel less robotic (and maybe a little more like a helpful intern who swears), while lightening your load with technology that actually serves you.* Mary’s path from librarian and tarot reader to tech director and business coach* How she organizes AI “staff” into departments—finance, operations, marketing, and more* The surprising power of giving your bots names and personalities* Why AI reveals more about your delegation habits than you think* How to build an AI “board of advisors” with personas like Mark Cuban or Reese Witherspoon* Emotional patterns people bring to technology (and what that says about leadership)* Creative personal uses for AI—from meal-planning and purchasing decisions to health tracking“I would argue if you had an intern, if you had a Gen Z Remy with you, you’d still fact check them because they’re young, they’re learning. I need to make sure that everything’s right. And in that sense, you’re still doing the same functions, you’re not doing less, you’re really not doing more. It’s just moving along faster.” - MaryAbout our GuestMary Williams: Sensible Woo | Sasquatch Media GroundsYou, Me ChatGPT WorkshopListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
What happens when every business book tells you what to think—but never explains what or how to do it?In this episode, Meg interviews Jessica about her new book, Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works. The conversation traces how the book came to life—from frustration with hollow business advice to the creation of a grounded, systems-based framework for experts who want to stay small, sustainable, and sovereign.Jessica shares how she read her way through the entire business section—books that were motivational but hollow, all premise and no practice. Some were thinly veiled sales funnels; others were memoirs pretending to be manuals. None answered the questions solo business owners actually ask: How do I make better decisions? What kind of business am I running? What’s enough? And how do I make this sustainable?They explore what’s missing from most business books, the trap of “CEO-energy” culture, and the myth that scaling is the only path forward. Jessica shares how years of client work, research, and teaching evolved into a practical field guide for soloists who want to build differently—without gambling their time or integrity.Get the details behind Leaving the Casino!* Why Jessica wrote Leaving the Casino after realizing most advice ignores context* How the online business world sells tactics that don’t fit most experts* Why many books are either memoirs or funnels to a paid program* How Jessica went from consulting to creating and publishing the book* The limits of frameworks like Profit First, Traction, and Essentialism* The risks of outsourcing sales, marketing, and finance too early* Responsibility, enoughness, and right-sized growth as operating principles* How privilege and life circumstances affect what “success” looks like* Why the book blends manifesto and textbook—both call-to-arms and manual* Jessica’s hope that it becomes a long-term reference for expert entrepreneursResourcesLeaving the Casino: Stop Betting on Tactics and Start Building a Business That WorksConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
What happens when our usual ways of dealing with conflict stop working (if they ever worked)?In this episode, Shivani Mehta Bhatia joins Aggressively Human to talk about the changing nature of conflict—especially in a world shaped by grief, uncertainty, and fraying trust.We explore how conflict has shifted post-2020, how our nervous systems are adapting (or not), and why repair feels harder than ever. We talk about Shivani’s approach of “conflict midwifery,” destructive versus generative conflict, and what it means to build and lead with more care in increasingly reactive times.Whether you’re navigating tension in your team, your audience, or your closest relationships, this conversation offers a more humane way through.* What conflict looks like now—and why it feels more brittle* The 5 parts of Shivani’s “prism of conflict”* What “conflict midwifery” means and how it changes the repair process* What ChatGPT says are the fixes of our current polycrisis* What it takes to repair when there’s no shared script* What’s the smallest possible actions we can take in conflict* Leading and relating in a time of collective dysregulation* How we can prepare—not avoid—hard conversationsAbout our GuestShivani Mehta BhatiaMonthly Conflict ClinicConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
What happens when your content calendar makes you want to set your business on fire?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 when and how to use data and systems to support you.This is a conversation about honoring your capacity without disappearing, how to say no to content you resent, and why creative rest is not a threat to your business—but often the reason you stay in it at all.* What it really means to have a “human-first” business (hint: it’s not about the right font)* The burnout that comes from forcing content for the algorithm* Navigating visibility after a performance hangover* When to blow up your content calendar for the thing you’re excited about — and when not to* Choosing the work that feels good, even when it doesn’t scale* The myth of “consistency” and what your audience actually needs from you* The identity whiplash of letting go of “known” offers to create something new* How Megan is reshaping what success looks like in her next chapterAbout our GuestMegan DowdConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
We often talk about launches as big, flashy events. But what happens behind the scenes when you’re not just releasing something new—but becoming someone new in the process?In this episode, Meg takes us inside the creation and launch of Findable Everywhere—not as a polished “launch debrief,” but as a real-time reflection on what it means to declare a new chapter in your work. We dig into the decisions along the way: how a paused summit talk became a test run, how she built a course that worked for beginners and advanced folks (and the complications that come with that), and how teaching this material sharpened her clarity and authority. Plus: the real numbers, the behind-the-scenes updates, and the emotional roller coaster of launching while also changing.But even more, Jessica and Meg get into the behind-the-scenes decisions, pivots, and identity upgrades that can only come from publicly claiming your voice—even if you’re still figuring out what it sounds like now.* Why this angle simmered for over a year before it became an offer* How a “focus group” (aka an old summit talk) helped clarify the direction* What shifted in Meg’s identity and voice as shifted from AI as separate to AI as integral to client results* Why Meg built Findable Everywhere for both beginners and seasoned marketers—and what that complicated* The emotional roller coaster of launching something that feels deeply personal* The real numbers, real process, and real moments of “do I even want to do this?”* Why launches aren’t just marketing events—they’re identity markers* How teaching the material shaped Meg’s own authority* The difference between planning a pivot and living one in real timeWant to get access to the challenge and a YEAR of implementation support?Join the Content Love Lab and be on your way to be Findable Everywhere.Live Trainings begin October 7, and you can get twice a month check-in on your content!Join the Content Love LabContent Love LabConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
Let’s be honest, we started this podcast as AI skeptics — skeptical of AI to write and sound like us without falling into language homogeny, AI pitch slaps in the DMs, and using AI to replace our thinking.But how are business owners using AI in creative ways that honor the voice of our businesses while being more effective?Enter Prerna Malik and Content Bistro. Prerna caught our eye with the Skeptic Buyer Bot—a tool that actually helps creators pressure-test their sales pages and offers through an AI-powered lens. (Yes, Jessica used it. Yes, she has thoughts.)We dig into how Prerna is using AI to amplify human work, not replace it. How her agency turns real voice-of-customer data into conversion gold. And why the best sales copy isn’t about cleverness—it’s about clarity, empathy, and making decisions easier for your buyer.* What makes a good AI tool (hint: it’s not a clone of you)* How Prerna uses the frameworks behind the Skeptic Buyer Bot to improve sales pages (because not every buyer is the same)* Why real customer data is your best copy asset* What makes a good voice-of-customer process (and what doesn’t)* Why AI should make your thinking better—not do it for you* When to not listen to best practices and trust your voice instead* Why thoughtful critique is one of the most valuable services you can sell“You need to remember, you are the superior brain. You need to look at the facts. You need to check everything. You just cannot ever take what. LLM chat, Claude or anyone else is giving you as the truth.” - PrernaAbout our GuestContent BistroSkeptic Buyer BotConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
What happens after you leave a business you built? How do you relate to work, money, systems, and your nervous system when your entire identity has changed?In Part 2 of our conversation with Erika Tebbens, we go deeper—into the murky middle of business ethics, entrepreneurship under capitalism, and how we’re operating in the political climate of 2025.We talk about the ethics of selling transformation, why systems don’t always equal support, and what Erika has learned about nervous system safety outside the online business bubble. This episode is full of those “I’ve been thinking this but no one’s saying it” moments, plus a little bit of righteous rage and some gentle reminders that you’re allowed to do things differently.Whether you’re reimagining your business, your systems, or your relationship to capitalism itself, this episode will give you plenty to think about—and maybe even a little relief.In this episode:* What happens to your identity after entrepreneurship* How to design systems that support your actual nervous system (not just your productivity)* The uncomfortable truth about selling transformation online* Why the ethics of business can’t be separated from capitalism* What real resourcing looks like—beyond time freedom or self-employment* Why Erika feels more supported working in an organization than she did soloAbout our GuestErika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-MakingConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
What does it take to walk away from something that’s “working”—even if it’s not working for you anymore?In this episode, Erika Tebbens joins us to talk about her career pivot out of entrepreneurship and into employment. After years of running a successful, values-driven consulting business, Erika realized that being her own boss no longer served her well. So she made a bold move: she got a job, at a dream company, in a field she deeply cares about. And how Erika’s move back into farming and farm systems so perfectly aligns with the Aggressively Human ethos.This isn’t your typical “how to change careers” episode. We talk about the real emotional rollercoaster of identity shifts, why online business doesn’t always deliver on its promises, and how to reimagine freedom when you're no longer selling yourself online.In this episode:* Why Erika walked away from her consulting business (even though it was “working”)* The grief and relief of leaving behind entrepreneurship* How she landed a job she loves in this economy (and it’s not about hundreds of applications to the LinkedIn black hole)* What it’s like to re-enter the workforce after 20 years of being the boss (and the feeling of only having one job, instead of having 15 jobs as a solopreneur doing it all)* How to tell the difference between real freedom and the illusion of controlAbout our GuestErika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-MakingConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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
When you're building something with a co-founder or even partners (like, say this podcast), it’s not just your business that needs tending—your relationship is the business.In this episode, we talk with psychologist and leadership coach Dr. Matthew Jones to talk about the often-overlooked emotional labor of working in partnership. We explore the dynamics that make co-founding relationships thrive (or fail), and what it looks like to prioritize care, communication, and clarity in a space that’s often full of pressure, ambition, and high stakes.We also talk about how to navigate conflict before it turns into resentment, how to separate identity from performance, and why leading with someone else requires emotional maturity—not just shared goals.Whether you’re co-leading a business, collaborating on a big project, or just trying to make it work with a fellow human in your orbit, this episode is a reminder: the relationship is the container.* Why your co-founder relationship is the most important “system” in your business* How to name the power dynamics that exist—and move through them with care* The three languages present in co-founder communication - and why overindexing on “goals” might be counterproductive* Building routines that strengthen the relationship, not just the company (think “date nights”, but for co-founders)* How we can (and can’t) use AI to help us communicate with our co-founder* Why emotional fluency is core to shared leadership* Matt’s journey of self-publishingAbout our GuestDr. Matthew JonesThe Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup SuccessMentioned ResourcesJohn and Julie GottmanImago TherapyNoam Wasserman’s The Founder’s DilemmaConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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




















