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

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
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

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
Connect with Us
Listen on Spotify
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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
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 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
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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 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