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

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
Connect with Us
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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

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
Connect with Us
Listen on Spotify
Listen on Apple Podcasts
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

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)
Connect with Us
Listen on Spotify
Listen on Apple Podcasts
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
Connect with Us
Listen on Spotify
Listen on Apple Podcasts
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

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 impact
The 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 Mattern

Register 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 Guest
Shannon Mattern
Free Business Course for Web Designers — raise your prices and stop undercharging
Connect with Us
Listen on Spotify
Listen on Apple Podcasts
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