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

AI coding tools have made it possible for anyone to build an app by just describing what they want. And solopreneurs are doing exactly that—from quiz tools to iOS apps to full CRMs. However, there’s a lot more to this conversation. In this episode, we’re joined by Joe Casabona of the Streamlined Solopreneur. Joe has a master’s in software engineering and spent 20+ years as a developer before pivoting to help solopreneurs build systems that let them actually take time off. He’s been deep in the vibe coding world—building iOS apps, beta reader tools, and more—and has strong opinions about what’s worth your time and what isn’t.We get into what vibe coding actually is, which tools people are using, and how code goes from running in a sandbox to something real people can access. This isn’t a “vibe coding is the future” episode. It’s an honest look at the tradeoffs—security, cost, opportunity cost, and the sneaky way tinkering can start to parade as productivity.* What vibe coding actually is, and which tools solopreneurs are talking about most (Lovable, Claude Code, Cursor, Codex, Replit)* How code goes from a thing running on your computer to something actual humans can access and use* The types of projects that are good candidates for vibe coding—and the ones you should probably leave alone* What happens when vibe coding gets you to 80% but can’t get you the rest of the way* Security risks that are easy to miss: exposed API keys, plain text credentials, and more* HIPAA, PCI compliance, and other reasons to think carefully before vibe coding certain apps—no matter how cool they sound* The “procrastination parades as productivity” trap, and how to tell if your tinkering is actually serving your business* Why token costs matter more than most people are factoring in right now* Joe’s lawnmower test: when just paying for the tool is the smarter move* The 10-point framework Joe uses before starting any vibe coded project"When you vibe code something and something goes wrong, it is a very helpless feeling if the AI can't fix it, because now you are taking something that you didn't write that you may not be familiar with. With my iOS app, it was like, 'There's something wrong with P list.' And I'm like, 'What is P list? Like, I don't know what that is. Can you just fix it?' And it's like, no. At some point you will hit this plateau where you can't take the app any further or something is broken. And you either just have to shrug or actually hire a developer to fix it." — JoeAbout our GuestJoe Casabona Website | LinkedInJoe's 10-point checklist for coding with AI 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

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

AI clones and GPTs are increasingly common, which brings forth so many questions! But the “aggressively human” question we’re exploring today is how much care, curation, and legal scrutiny goes in before you release it to real people.In this episode, we talk with return guest Diann Wingert, ADHD business coach and host of the ADHDish podcast, about Di AI — her newly launched digital coaching clone. Diann is a former psychotherapist turned business coach who works exclusively 1:1, and she just released a Coachvox-built AI version of herself in beta to current and previous clients.We get into the technical, client experience, and ethical questions of cloning a coach. We cover what Diann chose to include (and exclude) in the training data, the months of fine-tuning behind the scenes, the legal work she did before launch, and why she’s not trying to turn this into a passive income stream.* Why Diann has been wanting to “clone herself” since Dolly the sheep — and what finally made it possible* Choosing Coachvox over other clone platforms (and why support and training mattered more than the tech)* Why guest episodes and client success stories were excluded from the training data* The painstaking fine-tuning process: ~100 questions per framework, batched over months* Removing language she’d never use — like “ADHD is a superpower” and “work with your brain, not against it”* The legal work behind the launch: hiring an AI-savvy attorney to rewrite her privacy policy and terms of use* How she’s drawing the line between coaching and therapy inside the bot* Why she’s giving Di AI away in beta — and what data she’s actually trying to gather* The OCEAN personality score and how it’s reshaping how Diann talks about her ideal client* Risk tolerance, exit strategy, and what it looks like to run an experiment in public“I don’t want somebody going to the internet or to Gemini or Perplexity or Claude or ChatGPT when they’re running a business and they have an ADHD brain. I would much rather they go to something that is just my information. Not because I know everything about running a business with ADHD — ‘cause nobody knows everything — but because the information has already been filtered through 30 years of experience, multiple frameworks and models. And they can’t get an opinion at this point from Di AI that is not entirely consistent with that.” — Diann WingertAbout our GuestDi AICoachvoxWebsitePodcastLinkedInOCEAN personality testConnect 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

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

Which version of you is running your business right now? It might be your inner 16-year-old who thinks networking is stupid, or your inner 6-year-old who learned the only way to be seen was to prove how smart she was. Your nervous system doesn’t really care whether you call it mindset or trauma — it’s going to do what it’s going to do.In this episode, we talk with Nicole Lewis-Keeber, MSW, licensed clinical social worker, ICF-credentialed coach, and certified Dare to Lead facilitator, about how childhood trauma and nervous system responses show up in the way we run our businesses. Nicole spent 18 years as a therapist before launching her own business 12 years ago, and she’s been carving out space for this conversation ever since — even when therapists told her she couldn’t talk about trauma outside the therapy room and coaches told her to stop using the word entirely.We get into how our inner children influence everything from sales to visibility to pricing, why urgency is usually a trauma response, and what it looks like to pause and figure out who’s actually making the decisions in your business. This is a practical, honest conversation about what’s underneath the discomfort and what to do about it.* How childhood trauma shows up in business decisions we don’t even realize we’re making* The inner stories impacting Nicole and Jessica’s experiences* The difference between a nervous system response and a strategic business decision* Why urgency in your business is almost always a trauma response worth pausing on* Visibility was hard before digital culture — now it’s a whole different animal* Reframing sales outreach as a kindness when everyone’s nervous system is overwhelmed* The trap of trying to fix an entire broken system through your one small business* Black-and-white thinking about platforms, AI, and marketing as a trauma pattern* Taking pauses away from the dopamine drip of the 2026 information landscape* Getting clear on what you actually want from a platform before you let it into your nervous system“Your nervous system doesn’t give a shit what you call it. It’s just gonna do what it’s gonna do. Many people are walking around with traumatized nervous systems that don’t really realize what they experienced was actually trauma. It doesn’t have to be a big catastrophic thing. It can be smaller — like micro moments that add up. If you want to do something in your life that feels scary, which starting a business feels scary, those adaptations and patterns are probably going to show up. So let’s figure that out.” — Nicole Lewis-KeeberAbout our GuestNicole Lewis-KeeberTikTokConnect 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 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

The narrative surrounding self-employment is often binary: you’re either running a full-time business or you’re not. But is that the reality? What would be possible if we treated self-employment as a spectrum? And what do we face as we move across the spectrum in terms of time, money, and momentum? For this discussion, we’re welcoming back Softer Sounds founder, Off the Grid host, and author Amelia Hruby.In this episode, Amelia shares what led her to a significant decision at the end of 2025: scaling back her podcast studio Softer Sounds dramatically and putting herself on a six-month sabbatical for that side of her business while investing in the creator-style side of Off the Grid. We dive into the idea of self-employment as a spectrum, the many forms it can take across a career, and why moving along that spectrum is a feature, not a flaw.Hear from all three of us how we cobbled work together to build the income we needed across the years — the bridge jobs, the clients who weren’t the dream but paid the bills, and the years of audience-building that often preceded any real traction. This isn’t a conversation about how to build a six-figure business. It’s about what self-employment actually looks like at different stages, and what we’d do differently if the goal is to simply stay self-employed. * What Amelia’s six-month sabbatical actually looks like — and why she chose a third option instead of hustling harder or closing the studio* Self-employment as a spectrum: from side contracts and bridge jobs all the way to full-time business ownership (and back again)* How Meg, Jessica, and Amelia each cobbled things together to get started — and what cobbling it together still looks like for established businesses* The role of bridge work in creating the time and mental space to build what you actually want long-term* Why Amelia chose to focus on Off the Grid and The Interweb instead of doubling down on Softer Sounds* What publishing books (Amelia’s and Jessica’s came out within a week of each other in October 2025) has to do with long-term business strategy* Hitting your capacity ceiling — and the different forms it takes at every stage of growth* Authority building: why showing up consistently before a trend breaks is what actually creates leverage when the trend arrives* The privilege question: how partner income, healthcare access, and life stage shape what risks you can realistically take* When and why to go back “in-house”“The only consistent business models you can count on are being a CPA or owning a funeral home. Otherwise it’s gonna change all the time. If you wanna be self-employed long-term, you have to love the ride of it. You have to love that it changes all the time. Do you enjoy every moment of it? No, I do not relish in the fact that AI perhaps stole half my business. I don’t have to love that. But I have to love dusting myself off and doing something new again.” - AmeliaAbout our GuestYour Attention is Sacred Except on Social MediaOff the GridSelf-Employment is a SpectrumConnect 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

Every business owner hits that point where the thing that used to light them up now feels like a slog — and it usually happens right when the work matters most. Whether it’s February fatigue, launch number seven, or the creeping suspicion that you’ve said everything you have to say, the impulse to burn it down and start fresh is real. But is it burnout, boredom, or just a season?In this episode, we talk about the difference between being tired of something in your business and being done with it. We dig into the natural cycles of building — preparing, planting, harvesting, and resting — and why the reinforcement phase (the one that actually creates momentum) is the hardest to stay motivated through. Jessica shares what it’s like to be in the “hardening the cement” stage while wanting to chase something new, and Meg talks about her experience running Social Slowdown for 100 episodes and knowing when it was time to hand off the torch.This isn’t a pep talk about pushing through or a permission slip to quit. It’s a conversation about learning to read the signals your energy is sending you.* Why the repetition phase of your business feels boring but is where the real traction happens* The seasonal cycles of energy and creativity (and why Meg doesn’t launch anything in February)* Jessica’s harvest-to-reinforcement arc — and the tension between solidifying old work and chasing new ideas* The green light / yellow light / red light framework for deciding when to push, pause, or stop* Why your audience hears your message differently every time, even when you’re saying the same thing* How Meg knew it was time to retire Social Slowdown after 100 episodes and a book* The difference between reinforcing, repurposing, remixing, and just regurgitating your content* What to do when you still need to market but have nothing new to say* Why your best referral partners being in the same slump at the same time is a real business riskHow relationships and referral networks carry your message when you can’t"Reinforcing is going back in and putting more infrastructure in place to make it stronger. Repurposing is, or rehashing for that example is taking the same information and pushing it out in a different place. Remixing could be finding new ways to explain something." — MegMentionedAmelia Hruby/Off the GridConnect 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 podcasts don’t make it past episode 10. But somewhere around the year mark, something shifts—what started as exploring ideas and meeting people can quietly become something bigger, with more weight and more responsibility than you signed up for.In this episode, we explore the difference between hosting a podcast and leading a movement. We talk about the three types of motivations for a platform: the desire for fame, the intentional choice to lead with a platform, and the moral imperative—when you have something to say that no one else is saying.This is a conversation about the reluctant responsibility that comes with showing up consistently, having strong points of view that shapes the discourse, and being willing to change your mind as you learn more.* The three motivations for creating a platform: fame, leadership with a platform, and moral imperative* What we can learn from Hamilton and Burr, especially why “I want to be in the room where it happens” is different from creating the authority to create the room.* Creating into the void—the lag time between creating content and seeing its impact* What changes when people start quoting your work back to you* Why reluctance to lead (because you want to get it right) is an act of integrity* The responsibility of being a standard bearer when people you looked up to aren’t active in the space anymore* How compounding authority works over time* The difference between selling services directly vs. articulating a point of view* Why having strong points of view while staying open to changing your mind is so hard“I think that when you’re a movement leader, you have to be willing to walk on the ledge more publicly for much longer. With less feedback than you anticipate.” - JessicaResources MentionedAntimemeticsConnect 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

Social media in 2026 is definitely not the same as before 2020—and not even the same as it was last year. And for our “Aggressively Human” take on how social fits in your marketing stack, we’re bringing on our favorite Mindful Marketing mentor and return guest Andréa Jones.In this episode, we’re talking about what’s actually happening on social platforms in 2026, especially for expertise-led businesses that don’t want to become full-time media companies.We talk about the TikTok effect, discovery-driven algorithms, and why entertainment now beats education on most feeds. Andréa shares how she thinks about social media today, how she uses it in her own business, and where it fits alongside other channels like podcasts, newsletters, websites, and SEO. We also talk about why viral content often fails to translate into clients, and how people really decide who to hire.This episode is an honest discussion at where social media sits now in a broader marketing mix—and what expectations make sense to have if you’re still showing up there.* Why social media feels louder, faster, and less useful than it used to* The “TikTok effect” and how it changed every platform* Discovery algorithms vs. follower-based feeds* Why entertainment content outperforms educational content* How engagement has declined across most platforms (and what that means)* Why viral posts often don’t translate into revenue* What Andrea puts in place before social media matters* The role of podcasts, newsletters, websites, and SEO* Local vs. national businesses and how discovery actually works* Why repetition builds trust (for humans and AI)“It takes a lot more effort for someone to leave that video or leave that post and go somewhere else to then do something else, like sign up for a newsletter or purchase something. So that sales cycle has gotten astronomically longer. And so I'm not saying social media isn't important. Especially for me, it's a great networking tool. However, it's not, and as far as the hierarchy goes, it's just not as important as other marketing assets. And so I had to shift the way that I think about that.” -AndréaAbout our GuestWebsiteOnlineDrea on InstagramMindful Marketing PodcastConnect 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

Lately, a lot of well-known course creators have closed their flagship programs or shut down their podcasts. Other online course creators who will “never again sell live training”…. well, they’re back with live training.Is the course bubble over? Will AI shut down courses? Or is this just an industry hot take to get clicks and views? In this episode, we talk about what’s actually happening with courses right now—and what’s not. We look at why self-guided, evergreen courses worked for so long, why they’re struggling to convert and retain attention now, and how AI has sped up changes that were already underway. We talk about how this has shown up in the various evolutions of our own businesses. We also talk about where courses still make sense, where they don’t, and why people are increasingly unwilling to pay for information without context, support, or application. (A multimedia interactive experience as Jessica called it in corporate-speak).This isn’t a declaration that courses are dead. It’s a conversation about saturation, economics, attention, and what people actually want help with in 2026.* Why course closures are becoming more common* The difference between a bubble bursting and a market maturing* What made evergreen courses work in the first place* How rising ad costs and shrinking arbitrage changed the math* Why beginner-level education scaled—and why it hit a ceiling* What AI replaced almost instantly (templates, boilerplate, generic content)* How Meg and Jessica have both surfed the wave of courses, both as leaders and as students* What people still pay for (and what they won’t)* The problem with “lifetime access” promises* Courses as one piece of a broader ecosystem, not the whole business“If you have a giant course where you promise to do everything, then you can’t do all of it well. And I think people are getting a little bit tired of like the survey courses, like the freshman 101 course of everything, or maybe those still exist. And I’m just out of the world view where I’m paying attention to them. But anytime that you have an all in one solution, whether that’s a course or a piece of software, or a coach who says that they can help you with everything, that breadth is going to prevent depth.And if you want to learn something deeply from a person who understands it and can answer your questions when things go wrong, then that’s when you want to find an expert who teaches one thing really well instead of 10 things mediocre.” - MegConnect 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 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

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

Instead of the polished Meta ads and the seamless email sequences, get the real behind the scenes of our businesses over the summer: the good, the hard, and the realities of summers in our businesses.* Why Jessica is running Meta ads and why she feels she’s doing it wrong* How Meg has leaned into retainer work this summer and it’s been exactly what she needed* The soothing activities of repeatable, even some kind of boring work* Confronting business model realities (“it can be easy to sell or easy to deliver but it cannot be both”)* Meg’s fall challenge: Findable Everywhere (because even though how we search might be changing, the fundamentals of showing up in AI and SEO are even more critical). * Jessica’s summer program debrief, and how it went from 9 prompts to 6 videos, 30+ prompts, and 10 detailed resources.* Jessica’s fall, including the Define Your Foundations business building cohort and the book launch.Join us this Fall:* Findable Everywhere: A 5-Day Challenge to Show Up on Google, ChatGPT, And Wherever Your Dream Clients are Searching* Define Your Foundations: Escape the “Tactics Trap” and start building real business foundations.Connect 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

“It's not, you know, oh, ‘I was working with these clients and then I was in the shower and while I was washing my hair, I had this great idea and I made a website.’ Like it's never that way, but that's how it looks on the outside.” - MegWe always see the polished outcome of change.The business owner who goes on sabbatical… to emerge with newly-refined offers and a perfect website.The offer idea that emerged in the shower… and is immediately birthed into a pristine sales page (with seemingly no revisions needed!).But what happens in the middle? And why does so much of the work happen after the first draft of any change in the editing and remixing process?We talk with Samantha K Pollack from Indie Copy Studio about what it means to remix your business through her journey from a launch copywriter behind-the-scenes of big brands to her new business model. We talk about the slow, murky, and very real process of business change: how shifts actually unfold, how you know something’s no longer aligned, and how hard it can be to hold the tension while you figure out what’s next.And we talk about editing: the power of an editor, why learning the craft of editing and writing is so important, when you need a copywriter (and when you don’t), and why editing is for your business, not just your writing.* The honest, behind-the-scenes look at a business in transition* The specific kind of stuckness that shows up when you're evolving* Why actually doing the work you want to do comes before the website, not afterwards* How Sam approaches editing as a craft, and why it matters* Why you need to learn your own rhythms to avoid sounding like generic AI (and why editing is safe from this generation of generative AI)* Why learning to edit your own copy helps you make better business decisions* The awkward truth that your website will never fully keep up“And when you look at someone else's writing and you're like, ‘this really spoke to me, like I really loved this little line right here. And then here's a place where I felt like I didn't really understand what you were talking about anymore.’ You're developing your own critical eye for writing and then you can apply that to your own writing.” - SamanthaAbout our GuestSamantha Pollack - and join the “Get the Mixtape” newsletterThe Craft small group writing workshopSubstack: https://substack.com/@indiecopystudioConnect 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

Entrepreneurship is hard. And it’s even harder when your nervous system is stuck in a mode that’s not serving you.In this episode, we sit down with The Entrepreneurs’s Therapist Shulamit Ber Levtov to talk about the nervous system realities of entrepreneurship—especially for those who didn’t become entrepreneurs by opportunity but by necessity.We talk about what it means to choose our nervous system activities, how to understand what’s in (and out of) our control, and the unique paradox of entrepreneurship: you get freedom… and also you’re the one holding the whole thing together.As Shula says, “Entrepreneurship and mental health are inseparable. We write business plans, marketing plans, financial forecasts, but where’s the mental health plan?”Whether you’re burned out or just bracing for what’s next, this episode offers frameworks and honest permission to put real nervous system management at the center of your business.* Why your nervous system is a business asset* How to distinguish between societal pressures, industry pressures, and our own decisions impacting our nervous systems* The paradox of entrepreneurship: control and uncertainty at the same time* Why some of us didn’t “choose” entrepreneurship—and why that matters* The role of locus of control and how it helps you manage business stress* When to phone a friend versus make a business decision in the moment* How to build a personalized nervous system toolkit (without another productivity checklist)“And then there's the very basic individual nervous system reaction to response running your own business. Business success equals survival. Intellectually, I'm not gonna starve and die if my business fails. I mean, it's gonna be stressful, it's gonna be hard. I may have very heightened circumstances. I may lose my house. A lot of really bad sh*t can happen, but it's survivable stuff if your business fails. But this is intellectual knowledge, not nervous system level stuff.” - ShulamitAbout our GuestShulamit Ber LevtovConnect 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

“Do you want to show up in those AI search results? Because AI is searching the internet now. AI is a search engine and it's looking at all those same things that Google is. So if you're not doing the [content] work, then you're being left out of that search.” - MegWhat role does content play in our businesses? And how does that shift over time?We may not have consciously chosen this as a duo, but Meg and Jessica are moving in two different directions in their business.Jessica, being just 5 years in, is moving from less content (and a few longer-term, higher-touch clients) to even more content and leveraged offers, and Meg, farther along on her business timeline, is moving in the opposite direction.But in both of our businesses, content (and the act of creating content) is still very important in our businesses, but in different ways. From content as teaching assets, to being found in AI, to helping us define our signature linguistic styles, we explore how we create content, why we create content, and how we use it throughout the entire customer journey. Hear why Meg produces detailed content for her community, why Jessica’s McKinsey training has made her slide presentations wildly too dense, and what we’re working on doing with our content during an AI-slop onslaught.* How our businesses have shifted since we started the podcast* The stages of building a foundational body of work* How the role content shifts when your business moves from broadcast and higher-volume to inbound and lower-volume* How can you be found in AI searches (and why the principles of SEO and good content matters even more now)* Proactive versus reactive content development, and the power of content that’s not meant for wide distribution* Why creating intellectual property is different than feeding an algorithm* What going more broad with your content does to your nervous system* How we think about lead magnets, content libraries, and reusing what still works* The questions we’re asking before we create anything new“But I think also creating content is a way to develop your signature phrases, the things that you're known for, the words that you use on the regular, what your client's parrot back to you and every time I've asked AI it comes up with snappy phrases, but it doesn't come up with my phrases.But I think the only way I can come up with my phrases and my shapes and my symbols and things like that is by creating the content myself.” - JessicaResources Mentioned:Diann Wingert: https://www.diannwingertcoaching.com/adhd-ish-podcastRyan Trahan’s 50 states in 50 days video: https://youtu.be/KTYbvU-aSf4?si=fCaJ3rZogru3hifUConnect 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

Everyone has been in bad meetings—and for many of you, being trapped in terrible meetings is one reason you became an entrepreneur in the first place.But what if meetings, and workplace culture generally, didn’t have to be awful? What if we could bring energy and collaboration, like the kind we get from a well-facilitated workshop, into our day-to-day culture?In this episode, Alison Coward joins Aggressively Human to show what it really means to lead through a facilitative and collaborative lens—not just to make meetings more efficient, but to make collaboration more human. We explore the difference between participation and true engagement, and why a good facilitator doesn’t just run the meeting—they make space for decisions, disagreement, and trust.And we also confront the realities of AI in the workplace. Because AI can craft the agenda and synthesize the notes… but can it feel the charge of conversation? And what do we lose when we outsource the hard conversations to software that avoids conflict and resilience building?* What “workshop culture” really means—and why it’s not just for facilitators* Why great collaboration isn’t about airtime, it’s about alignment* How to lead across generations when work expectations aren’t the same* The role of facilitation in navigating polarized teams and hard topics* Why AI can’t replace the discomfort, nuance, and trust-building of real conversation* The hidden labor of designing meetings that actually lead to decisions* Why clarity isn’t always the goal—sometimes it’s about making space for complexity* How to tell when your team needs a better process (not another tool)“When we default to using those tools, we're robbing ourselves of the chance to build those very human skills that enable us to relate to each other more effectively. Conversations are difficult. They're meant to be, that's why they're called difficult conversations. And sometimes the process of going through that difficult conversation hones and smooths the edges off. It's almost like a process that we go through that doesn't feel uncomfortable when we get to the other side. We've learned something new and perhaps we've built a connection with someone else. And the thing is, is that those kinds of difficult conversations or those situations are the very thing that people are like, oh, AI can do that for me now because they wanna avoid that uncomfortable feeling.”About our GuestAlison Coward and NewsletterLinkedInWorkshop Culture: buy directly from www.practicalinspiration.com or indiepubs for US customers and use code WRKCULT30 for 30% discountConnect 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

Jessica goes to conferences a lot, especially more now that she’s not employed full time. This is her eighth creator conference (4 World Domination Summits, 2 Craft and Commerces, 1 Neurodiversion summit, The Lab Offline, and a number of small mastermind and coaching retreats).So today’s episode is both a debrief on going to conferences and also a recap of the 4 takeaways from Craft and Commerce that are informing our year ahead.We dig into conferences:* Why putting yourself in the position to meet people can help you meet your internet heroes… and can also help you sell more things. (Shoutout to former guest Jeremy Enns here).* How does one maintain relationships with people so that the next years of the conference just get better and better?* Why presentation-heavy conferences miss the point, especially for more seasoned attendees (and how to think about the composition of the audience).And then, we dig into the four takeaways from the conference itself.* We’re entering into an AI content doom loop.* What’s your “use and refuse” AI strategy?.* Storytelling reigns supreme.* There is no “overnight success”.“If they don't exist, they will in the next six months is a tool that if you list a number of the influencers you wanna follow and comment on their post… and so you just feed it into an AI tool and that AI tool will come up with an AI generated comment. So you don't even have to log into LinkedIn. If this doesn't exist, I guarantee it will in like the next six months. You wouldn't even have to log in to see what your favorite influencer posted and the AI comments on their stuff so that your stuff feeds goes into the feed.And, some AI tool is gonna go into your library of content that you've created already, and it's gonna snip out something, drop it on LinkedIn, some other bot is gonna comment on it, and then there's no human involved in some of that stuff, period.” - JessicaMentioned ResourcesPamela SlimJeremy Enns’s Content Strategy SchematicNeurodiversion ConferenceShe’s so Lucky with Les AlfredConnect 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

Partnerships are everywhere in small business: business partners, project collaborators, behind-the-scenes co-creators, podcast co-hosts (hear our origin story!). But we don’t talk enough about what makes them actually work. If managing yourself is hard, imagine navigating the commitment (and the scheduling tetris) of two people.Emma Whittard (mindset coach) and Karen Worthy (executive career transition coach) had their “business meet cute” in one of Jessica’s classes. What started as simple client referrals turned into collaborations, a shared offer, and even Emma supporting Karen’s business behind the scenes. From the first casual chat to co-creating paid offers, sharing clients, and navigating logistics (like money, time zones, and email volume), we talk about how they built trust without a contract, how they make decisions, and what it means to do good work together.We talk about the emotional labor of collaboration, the unspoken agreements, and what it takes to prioritize relationship over revenue in a world that teaches us to keep everything transactional.Before teaming up with someone, listen to the foundation of what makes this collaboration work.* How a casual class connection became a long-term collaboration* Why their “Base Camp” offer came after the referrals, not before* What they’ve learned about setting boundaries, expectations, and pricing* The value of emotional support, operational partnership, and sounding boards* Navigating logistics: scheduling, tech, shared values—and the messy middle* Why trust (not contracts) is what makes these kinds of partnerships work“We also both said upfront that our relationship was more important than the business together. So the relationship first. That means that hopefully we won't get into a situation where there's something icky happening and we can't address it, or it sort of ruins things. So again, it is back to values and priorities again.” - Emma WhittardAbout our GuestsEmma Whittard | LinkedInKaren Worthy | LinkedInBase Camp OfferConnect 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

In this episode, we dig into the realities of running a relationship-led business in a market that’s no longer in beginner mode. Michelle Warner joins us to talk about what’s changed (and what hasn’t) in a world where quick wins and easy opportunities are drying up, and why now more than ever, the boring stuff—fundamentals, relationships, offers that fit—really matters.We cover how to adapt to a maturing market, where the “growth hacks” of the past aren’t working like they used to. Michelle shares why most client issues aren’t massive strategy problems but small, foundational misalignments—and why fixing them starts with a return to the basics.This is an episode for anyone feeling like what used to work just… doesn’t anymore. And for those ready to stop chasing the next big trick and return to the very unsexy, very effective roots of sustainable business.* Why the market isn’t broken—it’s just finally maturing (and your tactics need to, too)* The real reason your sales aren’t working (hint: it’s not because you’re not posting enough)* The problem with marketing arbitrage plays (Substack, LinkedIn newsletters, bundles—you name it)* Why your offer math might be the real problem behind your revenue plateau* How AI is making everyone sound the same—and how to stand out by being specific* Why the boring fundamentals are the most effective thing you can do right now* What to do instead of panic-posting when leads slow down“That's the key to relationships. The specificity and the “because statements” allow you to also build sticky relationships. So a lot of times when we're networking a, we don't know why we're networking with people, so we end up just meeting people and then trying to force square pegs into round holes, and b. so then you get stuck in these small talk traps.” - Michelle WarnerAbout our GuestMichelle WarnerSequence over Strategy podcastConnect 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

This week, we're doing something a little different. Instead of our usual dialogue, we’re sharing two short solo segments originally recorded for the Evidence of Humanity audio summit, hosted by Michelle Pontvert. This means we get a break from recording and editing but you still get a fresh episode. While because as Meg says, “Jessica loves a cadence”, taking breaks and thoughtful repurposing of content lets us take breaks and be aggressively human!First, Jessica shares how running free monthly workshops—starting with just four people—has become one of the most grounding, trust-building practices in her business. Not because they’re optimized for conversion, but because they create real-time space to test ideas, teach generously, and build actual relationships.Then, Meg takes the mic to talk about the surprising overlap between SEO strategy and romance novels. Drawing from her writing practice and deep love of story, she maps the early stages of the hero’s journey onto the buyer journey—and shows how thoughtful content meets people where they are, not where your funnel wants them to be.Let us know: do you like some shorter, solo episodes in your feed?We’ll be back next week with more dialogue!Connect 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

How do we build businesses and community inside a broken system—without replicating that system in our own work?By leading through an intersectional, feminist, and collective lens.In this episode, we talk with Becky Mollenkamp about what it means to build and lead this way: grounded in shared power, mutual care, and collective growth. Becky shares how her work as a coach and podcaster has evolved over the years, why she’s no longer trying to “go it alone,” and how building in community has been the most liberating move of all. We also talk about what it really means to earn money ethically, challenge systems without burning out, and keep showing up (even in the chaos of summer).We also get into the behind-the-scenes of launching multiple podcasts, navigating Substack and social media with ethics intact, and the real tension of building a business when you care deeply about people and want to pay your bills without selling your soul.This is a conversation for anyone trying to build something different in a world that rewards “the one right way to build.”* How Becky’s proximity to the Ferguson uprising catalyzed a shift in her perspective* The real difference between commerce and capitalism (and why most pricing models get this wrong)* What it means to build a business rooted in mutuality, not hierarchy* What the hell to do with Substack, Meta, and other imperfect tools* The behind-the-scenes of stewarding multiple podcasts, and the choice to have a co-host or not* The problem with trying to do it all alone—and how Becky’s moving toward collective action over solo growth* Why podcasting might just be the most human way to have the conversations we actually want to have“Yeah, I can come up with lots of ideas, but they're always richer when it's done in collective with these other women who have different lived experiences than me. And then, yeah, I'll move the ball forward. I love moving the ball forward, but I'm more excited now. I'm moving the ball forward with these ideas that are so much more richer.” - BeckyAbout our GuestBecky MollenkampFeminist Podcasters CollectiveFeminist FoundersMessy LiberationAssigned ReadingMentioned ResourcesTema Okun’s EssaySacred Economics by Charles EisensteinThe Soul of Money by Lynne Twist“The Master’s Tools Will Never Dismantle the Master’s House” — Audre LordeConnect 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

Most business advice assumes you're wired like everyone else. What if you're not?In this episode, we sit down with Diann Wingert—former therapist, business coach, and host of the ADHD-ish podcast—to talk about what it really means to build a business that works with your brain, not against it.We unpack the myths around ADHD, how to radically accept your own wiring, and what happens when you finally stop trying to “fix” yourself and start designing systems that fit you.Jessica and Meg share their own neurodiverse workarounds (including why their assistants actually manage them), and Diann breaks down how she flipped her brand, rethought her support systems, and uses tools like Claude.ai as external executive function—not a replacement for her brain, but a co-pilot for organizing all the genius.This one’s for the quirky kids, the not-quite-diagnosed, and anyone who’s ever tried to follow business advice that wasn't designed for their brain. * Why Diann rebranded her podcast and business to center ADHD-ish, not as a niche but as a reality* How radical self-acceptance (not self-awareness) is the real first step to change* The business systems that work because they’re nontraditional (like letting your assistant be the boss)* Why “It depends” is the real ADHD business motto* How tools like Claude and Notion help organize brilliance without replacing your voice* Why standard business advice falls apart when your brain doesn't fit the mold* What Diann learned from neurodivergent-friendly spaces (hello, marching band at a conference) and how to bring that into your own business model* The role of AI in organizing, not empathizing—and why therapy still needs a human touch“Human beings, by and large, are damaged through relationships, abuse, neglect, trauma. Most of the things that bring people to a therapist happened as a result of some failure of human nature. And so the whole transformation of therapy is that it is using the professional use of self. We are harmed by humans. We are healed by humans. It’s one of the most intimate and powerful ways of working. And I loved it.” - DiannAbout Our GuestADHD-ish PodcastMastering Your Entrepreneurial ADHDDiann Wingert’s LinkedIn NewsletterConnect 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 really mean to “stay solo” in a world that won’t stop telling you to scale? That’s the question we explore with Maggie Patterson, whose new book Staying Solo challenges the endless drumbeat of “bigger is better.”In this episode, we dive into Maggie’s journey from agency owner to solo business advocate, the messy parts of writing (and marketing) a book without turning it into a performative launch, and the very real tension between wanting to build a sustainable business—while feeling pressure to do it in a way that exploits your time or other people’s labor. (Thanks, online business influencers).We also talk about typos in print books, sticker packs as marketing tools, and why self-publishing may outperform traditional publishing as a soloist. Whether you’re a solopreneur, a micro-agency owner, or just someone wondering if you have to scale to be legit, Maggie’s perspective offers a breath of fresh air—and a permission slip to do it your way.* Why Staying Solo matters—especially when the default advice is always to “scale”* The tension between running an agency and telling others not to build one* How Maggie’s book journey came out of years of blog posts and a poolside conversation* The ethics of pricing, paying others well, and not replicating exploitative business practices* The weird relief (and panic) of finding typos in a printed book you can’t easily fix* How to stay human while promoting a book (sticker packs, handwritten notes, book tours)* Book marketing vs. book selling—why Maggie chose self-publishing and what surprised her most* The privilege of staying solo—and how to be clear about who you want to serve* Most importantly, the 5 book names for Maggie’s book themed birdhouse.About our GuestMaggie PattersonStaying SoloConnect 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

In this riffy, delightfully unstructured episode, Jessica and Meg ditch the outlines, frameworks, and “polished” content in favor of a real-life check-in, some AI trivia, and a sneak peek at Jessica’s summer program, Relationship Rhythms.We talk about how building relationships is about more than just dropping into people’s inboxes—and how Relationship Rhythms is designed to bring playfulness (and prizes!) back into the process. Jessica shares why she’s finally running an asynchronous offer and how Relationship Rhythms is different from her usual programs, plus what happens when you go from dreaming to launching.We also get real about our own partnership: the messy business of joint ventures, what happens when your business is in a different gear than your friend’s, and how to talk about money and collaboration in a way that feels human.And because she couldn’t resist, Meg quizzes Jessica on AI trivia—highlighting the joys, the contradictions, and the occasional panic about what AI knows, what it doesn’t, and how we’re using (and refusing) it in our own businesses.If you’ve ever felt like your business friendships are an ever-evolving dance—or wondered how to balance AI curiosity with human connections—listen in. 🍊PS. If you made it to the end of this episode, drop our Easter Egg word on Substack as a comment to let us know you’re here for the rambles, not just the frameworks.* Jessica’s summer program, Relationship Rhythms, and how it’s ushering in a more experimental vibe.* How Relationship Rhythms uses gamified accountability (yes, with prizes) to make relationship building fun* Why Jessica and Meg decided not to monetize the Substack—yet—and the honest convo about splitting podcast revenue* The challenges of co-hosting a podcast when your businesses are in different seasons (and speeds)* The messy beauty of relationship building: why some outreach grows instantly while others marinate for months* Meg’s AI trivia quiz: from radiologists to Reddit, from ChatGPT’s energy usage to recipes with random ground beef* Why learning how to learn will still be a critical skill, no matter about AI’s capabilitiesBloom’s TaxonomyJoin Relationship RhythmsSign up for the waitlist or join the program (opens June 9).Connect 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

Have you ever sat through a slide deck that felt like death-by-bullet-point? Or tried to sound like a LinkedIn thought leader only to bore yourself?Have you ever struggled to consider yourself “interesting” when you haven’t gone to space or climbed a mountain?Most importantly, how can you tell a story that AI cannot replace?Story coach and speaker whisperer Mike Ganino joins us to talk about how to actually connect with other humans through storytelling, public speaking, and intentional presence. We talk about what’s missing when AI writes your copy, how to make your keynote more than just a case study, and why the most aggressively human thing you can do is show up—with your voice, your weirdness, and your body and breath. We talk about what job AI can’t do, why “tell your story” is often the worst advice, and how the most impactful stories usually come from Tuesdays, not TED Talks.* How to pull stories from your actual life (even if they happened on a random Tuesday)* What ChatGPT can and can’t do—and why public speaking is still a human-only activity* Breaking free from the drip of consumption and embracing the interiority within us and around us.* How to find your “inner interesting”, and how to transform extraordinary tales into relatable, personable stories.* Why “tell your story” is terrible advice—and what to do instead* How book marketing breaks your nervous system and what our favorite GIFs reveal about usAbout our Guest:Mike GaninoMake A Scene: Storytelling, Stage Presence, and The Art of Being Unforgettable in Every SpotlightConnect 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