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

Most email marketing advice gets written for one audience: other online business owners. The cadences, the launch sequences, the “reply and let me know what you think” CTAs — they all assume the person on the other end is in the same world you are. They’re not, if you’re a therapist or a financial advisor or a lactation consultant. Your clients may not reply to your emails with “loved this!”, don’t expect launches, and aren’t waiting for your next email.
In this episode, we’re joined by returning guest Bev Feldman, email marketing strategist for credentialed professionals at Your Personal Tech Fairy. Bev recently repositioned her business to focus on credentialed service providers — and she’s having her best revenue months ever doing it. We talk with her about has changed in her business marketing, including the shift from “marketing” to “marketing AND sales,” replacing her freebie with a gated Services Guide, and the quarterly check-in email that’s converting her smaller, plateaued list better than it ever did when it was growing.
We talk about why most credentialed pros either email too rarely (out of spam fear) or too often (copying content-creator cadences), why “top-of-mind selling” works better than launch selling for service providers, and the difference between a newsletter (selling ideas) and email marketing (selling products and services) — and why that distinction matters when everyone is being herded onto Substack. We also get into welcome sequences, the Expert’s Paradox, the Gmail open-rate drop, and what happens to a sales call when a Services Guide does the qualifying for you.
* Why the online business email playbook doesn’t translate when your audience is consumers, not other online business owners
* The two extremes Bev sees credentialed pros make — emailing too rarely vs. copying daily content-creator cadences
* Reframing email as a sales tool, not just a marketing tool (with full credit to Kendall Cherry)
* “Top-of-mind for triggering events” — what selling actually looks like for therapists, financial advisors, and other service providers
* The Expert’s Paradox: why experts default to DIY tutorial content and why AI just commoditized that
* Replacing the freebie with a Services Guide that pre-qualifies leads before they ever book a call
* Why Bev’s list has plateaued — and why that’s a feature, not a bug
* Different welcome sequences for different entry points (Services Guide subscribers vs. newsletter subscribers)
* The quarterly “I have openings — want to work together?” check-in email
* Newsletter vs. email marketing: why Substack and Beehiiv are the wrong tool if you’re trying to sell services
* Why unsubscribes are good news, and the recent Gmail change that dropped open rates across the board
"Email marketing is not just a marketing tool, it is very much a sales tool. But you can do that in a way that's not just, 'Let me hammer you over the head with my offers,' but invite people into that sales process with you when the time is right for them. Think about how you are doing that person a disservice by not showing up. They came to you because they're looking for support or help with a very specific problem, and you could be the person to solve that problem for them. If someone has given you permission to show up in their inbox, you are not spamming them. You are doing exactly what you said you would do." -Bev

About our Guest
Bev Feldman
Kendall Cherry for the Services Guide inspiration
Heart Centered Email Marketing (Previous Episode)
Bev’s Services Guide
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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

Getting ripped off online used to feel like the worst-case scenario for putting your ideas out there. Now it’s a near-certainty — your work has already been scraped, ingested, and trained on, whether you wanted it to be or not. But, on the other hand, if you don’t claim your expertise early and often… you can’t be the one cited and known for your work.
In this episode, we talk about the tension between wanting to be found and being afraid of being stolen from — and why the answer isn’t to publish less. We get into what AI models actually train on, what it means to claim your semantic territory, and why naming your frameworks matters more than ever in an era of linguistic convergence.
We talk about real examples of being ripped off, the myth-busting around AI policies, and why information itself is a leaky moat: what’s worth protecting, what’s worth releasing, and why your discernment — not your information — is what people are actually paying for.
* The first time Jessica was beat-for-beat plagiarized — and why she made the stolen idea a cornerstone of her book anyway
* Why you can’t copyright a concept (only the specific words)
* The myth that AI trains on your private workshops and client conversations
* What an AI policy actually does — and doesn’t — protect
* Claiming your semantic territory vs. resetting your authority every time you post a Reel
* Why naming things (Sacred Sales Hour, Building Blocks, the Beacon Framework) creates findable entities tied back to you
* Linguistic convergence: why everyone in your industry sounds similar, and what to do about it
* Information is a leaky moat — what people are actually buying when they hire you
* Why gatekeeping “the secret” behind an hour-long presentation burns goodwill
* The difference between compounding authority and constantly starting from zero
“I think there’s this tension between I want to be found, in order to be found I must be public, but I want to be credited. And more importantly, I don’t want to be stolen from. And when I say I don’t want to be stolen from, what I mean is I don’t want someone to put their name on my stuff and sell it as their own. But I do want to be found. I do want to be cited. I think I’ve just decided that I can’t do anything about [people taking it] now. The more I put it out there in the world, the more likely it is that someone’s gonna stumble across something I wrote, but I want them to know it came from me. That’s why you need unique terminology, unique nomenclature — that’s hard to replicate, hard to rip off.” — Jessica

Resources
Jessica’s What Business Model are you Running?
Nathan Barry’s The Ladders of Wealth
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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

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!)
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

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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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

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
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