Aggressively Human

After nearly two years and a survey of 50+ members, Jessica’s Deeper Foundations membership had clearly outgrown its original container — and Jessica finally had the data to prove what was working, what was friction, and what needed to be rebuilt.

In this episode, Jessica walks Meg through the full arc: how the membership started as a 10-lesson video library for 20 superfans, grew to 150+ members with 2-3 weekly events, and what happened when she asked them what they needed now that the membership had grown. She shares the five member profiles she identified, the eight themes Claude surfaced from survey responses, and the new five foundations framework that now anchors the entire onboarding experience.

We talk about what it looks like to redesign something that isn’t broken but has gotten too unwieldy to navigate — and what it cost (including her back) to rebuild it in two weeks. Get a real look at what happens when you’ve been cobbling together gaps with your own presence for two years and then evolve the infrastructure to match.

* Why a membership built for 20 superfans doesn’t automatically work for 150 people who don’t already know your work

* Why the new design wouldn’t work on a smaller scale, and why community needs to evolve

* The five member profiles: Students, Coworkers, Community members, All-ins, and Drop-ins — and why welcoming all five changes how the experience is designed

* What members said about Sacred Sales Hour that Meg immediately called a sales page testimonial

* The eight themes surfaced from 40 survey responses and 10 intervies, and which ones were already suspected vs. actually surprising

* Why “content volume and navigation” is the top friction point — and how Jessica’s new Five Foundations framework addresses it

* Dunbar’s number, capping the membership at ~200, and why some things just shouldn’t scale

* Hiring from within the community — and why that matters when your methodology is the product

* How the Relationship Rhythms course complements and deepens the Membership’s foundations.

“This is copy from Claude, which I enjoy: Most business advice assumes you already know what kind of business you’re running and hands you the route — this content strategy, this sales script, this pricing model. Deeper Foundations starts earlier. The five foundations — business design, marketing, sales, operations, authority building, and planning — aren’t topics to pick from a library. They’re the terrain every sustainable business has to navigate, and this membership covers all five in sequence at the depth you’re at. It’s not proprietary secrets. It’s that Jessica organized the real fundamentals into a coherent system, and then shows up to help you apply it to whatever business you’re actually running and whatever level you’re at in each foundation.” -Jessica

Resources Mentioned

Deeper Foundations Membership

Relationship Rhythms Program (with live Q&A)

Josh Spector’s Clients from Content Membership (the original Membership Inspo!)

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Meg Casebolt

Jessica Lackey

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." — Joe

About our Guest

Joe Casabona Website | LinkedIn

Joe's 10-point checklist for coding with AI

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Jessica Lackey

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." -Jessica

Resources

TBM 417: Before You Fire All Your Glue People Because of AI

Matt Schumer “Something Big is Happening” Wikipedia page

Citrini’s 2028 Global Intelligence Crisis

The Panel with Justin Jackson and Brian Casel

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Meg Casebolt

Jessica Lackey

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 tense

A 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 Guests

Strange Birds

Mentioned Resources

Lauren Edwards Flying the Coop episode

Incorruptible by Eric Ries

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Meg Casebolt

Jessica Lackey

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 Wingert

About our Guest

Di AI

Coachvox

Website

Podcast

LinkedIn

OCEAN personality test

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Jessica 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." —Jessica

Programs We’re Referencing

Signal Mentorship

Define Your Foundations (cohort re-launching in September)

Deeper Foundations Membership (open every day!)

Providers Jessica uses

Jessica’s Launch Copywriter Courtney Fanning

Bev Feldman Kit Email Advisor

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Meg Casebolt

Jessica 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-Keeber

About our Guest

Nicole Lewis-Keeber

TikTok

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Jessica 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.” - Becky

About Our Guest

Becky Pierson Davidson

Resources Mentioned

Build with Becky Podcast (Becky’s micro podcast on community topics)

The Lab by Jay Clouse (where Jessica and Becky met)

Craft and Commerce Conference

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Jessica 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." -Meg

Resources

The Beacon Framework from Meg Casebolt

Why You Need a Named Framework from Meg Casebolt

Methodology as a Map from Jessica Lackey

The Iron Framework by Mel Deziel (from Creator Kitchen, with Jay Acunzo)

Blair Enns’ Four Conversations Framework

The Former Lawyer Framework by Sarah Cottrell

Curiosity and Why It Matters (book, mentioned by Jessica)

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Meg Casebolt

Jessica 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 conversation

About our Guest

Meighan O’Toole

Resources

Paul Graham’s “Maker’s Schedule, Manager’s Schedule”

Bullshit Jobs by David Graeber

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Meg Casebolt

Jessica 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