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

(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.

After a three-year break, Meg returns to blogging, emphasizing the importance of creating timestamped, owned content to establish authority and protect intellectual property. They discuss how written assets can endure in a world dominated by fleeting social media trends, providing visibility and a lasting presence. Topics include the advantages of blogging over other platforms, the significance of discoverability through keywords and links, and using structured content as valuable onboarding tools. Ultimately, the conversation highlights the necessity of building your online presence on solid ground.

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