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

The AI adoption conversation in early 2026 is loud, fast, and full of warnings that you’ll be left behind if you don’t move now. But for most of us, the real question isn’t how fast you can adopt every new tool—it’s whether the tool or use case is right for your business.In this episode, Jessica shares her own journey from existential AI FOMO in January (OpenClaw! ClaudeCode! Opus! Oh my!) to a more grounded relationship with which tools actually serve her business. Meg brings her framework on early adopter cycles, the system stress that follows loud hype, and why the people yelling the loudest about a technology are usually trying to prove something—to themselves or to you.We talk about what friction is actually telling you, the work AI is currently best poised to eliminate, and how to stay informed enough to make good decisions without getting sucked into the daily noise. * Jessica’s emotional arc from existential AI FOMO in January 2026 to a calmer, more grounded approach—and what actually changed* Why early adopters yelling about a technology often signals the window of advantage is already closing* The “friction as signal” reframe: how slowing down through manual processes reveals whether you should be doing something at all* What AI will realistically eliminate—repetitive, clerical, execution tasks—versus what stays irreplaceable (strategy, point of view, and looking someone in the eye)* The “glue jobs” problem: roles that hold organizations together without driving revenue directly, and the risk of automating them away before you understand what they do* How to tell the difference between adopting a tool because you genuinely need it versus keeping up* Why understanding how a system breaks is more valuable than just using it to generate output—and how building things yourself teaches you that* How to stay aware enough to make smart decisions without falling into constant FOMO-checking as a business strategy"The friction slows me down enough to be like, 'This was a poor choice, Jessica. Strategically, I'm asking, am I dragging my feet because it's taking a long time? Or am I dragging my feet because this is not the right move? If you don't drag your feet, you never ask those questions. And I was partway through building out Five Foundations as a suite of courses and I stopped and said, wait—is this actually what I want to do? And the answer was no. The friction gave me the time to figure that out." -JessicaResourcesTBM 417: Before You Fire All Your Glue People Because of AIMatt Schumer “Something Big is Happening” Wikipedia pageCitrini’s 2028 Global Intelligence CrisisThe Panel with Justin Jackson and Brian CaselConnect 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

Business governance — LLC, C-Corp, Co-Op…. sounds boring as hell. But is it?Instead of setting up a traditional partnership or agency, Anna and Janel of Strange Birds did something different — they spent a year building out the governance structure of a worker-owned cooperative.Anna has been running Strange Birds, an idea specialist consultancy for over six years; Janel joined two and a half years ago after leaving Meta — and instead of just adding a second name to the partnership agreement, they restructured the whole business as a worker-owned co-op.We dig into what a cooperative actually is and why it’s meaningfully different from a standard partnership, what the business case actually looks like (the survival stats are genuinely wild), and how going through the process forced them to have all the money, roles, and “what if someone stops pulling their weight” conversations that most business partners quietly avoid.* What a worker-owned cooperative actually is — and how it’s legally different from a regular partnership or LLC* Why 90%+ of co-ops outlast the 10-year mark while most traditional businesses fail within five* The personal case for co-ops: why the creative services agency model is broken and what a democratic ownership structure actually fixes* Equal pay, dependents, and the specific messy money conversation they had to have before finalizing their bylaws* Why the cooperative legal structure took them a year to formalize — and why that’s a feature, not a bug* How defining clear roles replaced the “we should all be interchangeable” model and made both partners more confident and effective* What “humans first” looks like in practice when a kidney infection takes someone out for a month* The structural safety nets they built into their bylaws for future members* How practicing difficult internal conversations has made them better communicators with clients* Keeping a 20-year friendship intact when you’re also co-running a business together — and the early warning sign when things start to feel tenseA cooperative model helps make sure we're all not just quote unquote horizontal — which, for people who have worked in horizontal business models, be real: was it actually horizontal? It was not. There was always a boss. Always a boss. There's always someone saying no. This is actually democratic. We all own it. We're all invested in it, and we all get paid equally regardless of if one person's services are bringing in more money — because a rising tide lifts truly all ships in a cooperative."About our GuestsStrange BirdsMentioned ResourcesLauren Edwards Flying the Coop episodeIncorruptible by Eric RiesConnect 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

Diann Wingert, former psychotherapist turned ADHD business coach and ADHDish podcast host, launched Di AI — a CoachVox-built digital coaching clone based on her frameworks. She discusses why she finally cloned herself, careful curation of training data, months of fine-tuning, legal and privacy work, strict therapy boundaries, and why the beta is aimed at current and past clients rather than mass market.

We’re both mid-launch as we record—and neither of us is following the big launch playbook. In this episode, we turn the mic on our own businesses as we’re launching while life-ing. Meg renamed her core program from a membership to a mentorship—the Signal Mentorship—and is figuring out how to re-sell something she’s already sold many times over when the positioning has changed. Jessica sold her six-month cohort almost entirely through personal emails, membership upgrades, and alumni re-enrollments, and is calling it what it is: a cozy launch. (Meg has to remind Jessica that that still counts as a launch!)We get into the behind-the-scenes logistics—pre-scheduling emails before vacation, hiring a copywriter if you’ll never actually write launch emails yourself, when and why to use paid workshops, and the feeling of “enoughness” in a launch.* Meg’s rebrand from the Content Love Lab to the Signal Mentorship—and why “membership” wasn’t the right word anymore* Pre-scheduling launch emails around vacation, jury duty, and client deadlines that don’t pause for you* Jessica sent 50+ personalized emails instead of a launch sequence—and why she felt like it “didn’t count” as a launch* The difference between “cozy launching” and “lazy launching” (hint: cozy launching is still a lot of work)* Why Jessica doesn’t use bump offers, fast-action bonuses, or urgency deadlines* How we invite discernment in our launches* What happens when you’ve launched the same program seven times and your people already know the rhythm* Meg’s paid challenge experiment that went sideways when people came back a month late demanding access* The power of low-lift launches over time* How authority compounds when you stop resetting and start building slowly over years"I had a cozy launch, as [former guest] would say. And this episode is all about cozy launching. But it's because I have been launching the same program with the same time spots for three years now. March and September. It also really helps when you have something that people can re-up and enroll again, because I'm never starting from zero. I'm starting from that one person who said, yes, I'd like to do this again with you." —JessicaPrograms We’re ReferencingSignal MentorshipDefine Your Foundations (cohort re-launching in September)Deeper Foundations Membership (open every day!)Providers Jessica usesJessica’s Launch Copywriter Courtney FanningBev Feldman Kit Email AdvisorConnect 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

Nicole Lewis-Keeber, licensed clinical social worker turned coach who helps entrepreneurs spot childhood trauma in their decision-making. She talks about how inner‑child parts shape sales, visibility, pricing, and platform choices. Short, practical takes on urgency as a trauma response, pausing before reacting, and reframing outreach as kindness.

In 2026, “community” is the new trend. The barrier to entry to launch a membership or community is lower than ever, which means the bar for making one worth staying in has never been higher.In this episode, we talk with Becky Pierson Davidson, founder of Affinity Collective, a boutique agency and the digital product partners behind memberships and apps that actually work. Becky spent a year as head of product at BossBabe managing thousands of members, decreased refund rates, and came out with a clear-eyed framework for what makes community sticky. She now works with 6, 7, and 8-figure founders to build community-driven products — and has just launched her own membership, the Affinity Collective, for community builders who are ready to scale. (Jessica is enrolled!)We talk about the most common mistakes community builders make in 2026, why overwhelm is the number one reason people leave, and how to think about designing a member journey that actually holds people — whether you’re running a community of practice, a transformational program, or something in between. We also hear about Becky’s Seven Figure Connected Community Model: Architect, Activate, and Amplify. (Ed Notes: Being documented in show notes is one way frameworks get found in search!!)* Why overwhelm — not lack of engagement — is the #1 reason people leave communities in 2026* What “meaningful engagement” actually looks like — and why forum activity is the wrong metric* The difference between a community of practice and a transformational community (and why they need different engagement designs)* Why AI is both the competitor and the opportunity for community builders right now* Becky’s framework for choosing between a bootcamp, a program, and a membership based on how long transformation actually takes* How to design for the 30–40% of members who are lurkers — and why that’s completely normal* The power of onboarding and a shared starting point* Why the commitment of a community might be the most human act in your business“People kind of are scared of building community because of the commitment of it. They think in order to do this they have to be super extroverted or they have to show up forever. But there’s lots of ways to build this into your business without having to be a front stage performer. Whenever we’re working on a community strategy for somebody, we’re thinking through, ‘What’s your business vision, how you do you want to show up, what’s your zone of genius?’. We ask those questions so that we build not only an experience that works for members, but also an experience that works for you as a business owner. Because human connection — like when you have low months and you have rough chapters — it’s your community that gets you through.” - BeckyAbout Our GuestBecky Pierson DavidsonResources MentionedBuild with Becky Podcast (Becky’s micro podcast on community topics) The Lab by Jay Clouse (where Jessica and Becky met) Craft and Commerce ConferenceConnect 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 about frameworks — what they actually are, why they matter more than ever for getting found in AI search, how they set your work apart, and how they work as a sales tool without turning your discovery call into a free consulting session.Search has changed — and with it, that means how we approach our content has changed. Five years ago, a broad range of posts and decent keyword density was enough to get found. Now Google and AI tools are matching intent, not just words… so what do you do when you need to go beyond keywords? We bring in frameworks. We get into the mechanics: the difference between architectural, transformational, and diagnostic frameworks; how a named framework becomes its own node in an AI knowledge graph; and why a framework does at least 15 times the work of a piece of content that’s just “everywhere.” This isn’t about having the perfect, finished methodology. It’s about why staking your intellectual territory now — even imperfectly — is the move.* Why AI-mediated search rewards frameworks and how that’s different from the old keyword-matching era* How the Aggressively Human philosophy would have evolved over time* What it actually means for a framework to “become an entity” and live independently of you* How to build a pillar page and content clusters around your named framework* Using a framework on a sales call to show your approach without doing the work for free* Why a process framework can give confidence on your skill as a guide — including the hard parts, the identity crisis, the plateau* The difference between architectural frameworks (here are the pieces) and transformational ones (here’s the journey)* Frameworks as content engines: how six pillars becomes six newsletters, six webinars, and six entry-point offers* Why “it’s still jello” is okay — start claiming your semantic territory before the framework is fully formed* How omnichannel reinforcement (podcasts, guest appearances, newsletters) amplifies a framework’s reach"Frameworks showcase ‘Here's how I'm different.’ It's not just I have this offer, I have a group coaching program. We meet every two weeks. That's a feature, that's not a methodology. But if you can explain your way of thinking, then AI can parse out what you do that's different. There were two other entities in that recommendation from AI and it differentiated between all of you. Not because you called yourself something different, but because it could parse out your way of thinking and how that client's experience would be different based on who she hired. And that's not something that could have been parsed or understood or recommended five years ago in the old system." -MegResourcesThe Beacon Framework from Meg CaseboltWhy You Need a Named Framework from Meg CaseboltMethodology as a Map from Jessica LackeyThe Iron Framework by Mel Deziel (from Creator Kitchen, with Jay Acunzo)Blair Enns’ Four Conversations FrameworkThe Former Lawyer Framework by Sarah CottrellCuriosity and Why It Matters (book, mentioned by Jessica)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

Many conversations about AI in the entrepreneur space default to content generation — blog posts, social captions, first drafts. But that’s only one layer of what AI can do, and for a lot of people, it’s not even the most useful one.In this episode, we’re joined by Meighan O’Toole of Ops+Bots, a Notion architect and workflow specialist who helps small teams build scalable systems they’ll actually use. Meighan has been using Notion since 2019, is a Notion Ambassador, and brings a perspective shaped by ADHD and navigating long COVID — including nearly a full year where they couldn’t work. That lived experience completely changed how Meighan thinks about what AI is actually for.We talk about the real difference between LLMs, chatbots, and agents; where Notion AI genuinely shines (and where it doesn’t); and why the tools that reduce administrative burden can be a genuine lifeline for people managing chronic illness, ADHD, or financial constraints.* The difference between LLMs, chatbots, and agents — and why understanding it changes how you use AI tools* What Notion AI actually does (and why it’s not about generating content)* How agents handle meeting notes, statements of work, and client updates — and what that’s worth to a solo operator* Where agents can support the admin work that many of us (especially with ADHD) don’t have the inclination or capacity to do* Long COVID, chronic illness, and the part of the AI conversation that’s often missing in entrepreneur spaces* “Human in the loop” — why AI works best as a co-pilot, not on autopilot* Privacy, security, and copyright concerns — which are real, which are amplified, and which were already there before AI* Why class and marginalization belong in the AI conversationAbout our GuestMeighan O’TooleResourcesPaul Graham’s “Maker’s Schedule, Manager’s Schedule”Bullshit Jobs by David GraeberConnect 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 answer to growing your business wasn’t building a funnel or crazy AI workflows, but being human, and building discernment and relationships? In this episode, we talk with Shannon Mattern, founder of the Web Designer Academy, where she teaches web designers how to package, price, position, and sell their services. She came up through freelance web design herself—undercharging, over-delivering, treating clients like bosses—before closing that side of her business and pivoting to teach others what she had to learn the hard way.We talk about what’s actually driving undercharging, how AI is a repositioning opportunity when seen strategically, and why the real value of a web designer has never really been the design itself.* Why web designers undercharge—and why the root cause runs deeper than mindset or confidence* The codependency cycle: from people-pleasing freelancer to the same patterns showing up in her own business* Building a business through referrals and word of mouth instead of paid ads and growth hacks* Why hiring people different from yourself actually improves the business (even when it's uncomfortable)* Why competing on price is a trap, and what to position on instead* Why AI tools like Wix and Squarespace aren’t the threat most designers think they are* Repositioning from “I make websites” to “I’m a business strategist and growth partner”* How AI is actually a reason to charge more—not less—if you reposition around strategy and business impactThe truth is, designers hear me when I say this or anybody doing anything where like [00:30:00] part of your business relies on a piece of software that your expertise is not knowing how to manipulate that piece of software to. build the thing. It's the fact that you can even translate what a client's needs are something that's going to them the outcomes and results that they want.” - Shannon MatternRegister for the Simply Profitable Designer Summit, March 16 - 20, 2026.The way people find and use websites has changed. Learn how to design for conversion in the AI search era.About our GuestShannon Mattern is a Pricing Strategist and the creator of the Package Matrix™. She is the founder of Web Designer Academy, where she spent a decade helping women web designers move from undercharging to premium pricing - and where she developed the Package Matrix™ framework now used by service providers across industries. Learn more about the full framework at https://shannonmattern.com/package-matrixConnect 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

Amelia Hruby, founder of Softer Sounds and author of Your Attention Is Sacred, is a creator and podcast producer who reimagines self-employment as a flexible spectrum. She discusses pausing her studio for a six-month sabbatical and shifting focus to creator-led projects. Short takes cover cobbling together income with bridge work, scaling limits, and why moving along the spectrum is normal.