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

Most program pages tell you what you get — the calls, the modules, the bonuses. They almost never tell you why the thing is six weeks instead of six months, or why the schema markup lesson moved from week three to week six.
In this episode, we walk through our own fall programs: Meg’s Signal, a year-long mentorship focused on AI discoverability, and the seventh round of Jessica’s Define Your Foundations cohort. We’re not pitching them so much as taking them apart — what’s in each phase, what order things go in, what we changed after watching people get stuck, and what we’ve learned about how long it actually takes for work to sink in.
We talk about why Meg teaches live twice a year instead of going evergreen, why Jessica spread the “intellectual horsepower” decisions across six months instead of front-loading them, how the BEACON framework maps to positioning work, and where our two programs hand off to each other. We also get honest about who each program isn’t for.
* Why the length of a program should be dictated by what’s actually in it
Signal Details:
* Meg’s Signal: four three-month cycles, and why it’s a mentorship, not a membership
* Why “learn it twice” beats “learn it once” — and what happens between the training cycles
* Why Meg won’t make the program evergreen (spoiler: the material changes every six months)
* The BEACON framework: brand entity, expertise, authority, content infrastructure, omni-channel presence, narrative
Define Your Foundations Details:
* Jessica’s four phases in Define Your Foundations — and why phase one is setting down the shoulds
* “Business model Tetris”: how your client, offer, and price point change what marketing you actually need
* Why front-loading every big decision makes people feel behind
* Co-working and laser coaching vs. office hours — designing for people who don’t ask questions in groups
* The three things that separate cohort members who get results from those who don’t
Which Program Might Be Right for You:
* Where positioning work ends and discoverability work begins (and which one to do first)
* Who each program is not for
“There’s another business coach who does a six-week accelerator, and she goes through her six core systems, because she has six systems similarly. And I’m like, ‘that is like pouring a flood of water onto concrete.’ It’s so fast. Her whole thing is fast, and my philosophy is that if you try to learn six full business systems in six weeks, you’re not gonna retain any of it.
So my point of view is not just about what the systems are, but how it informs the offer itself and the client I’m serving. And if they want speed, awesome. My narrative has to connect to what I’m selling and why.” - Jessica

Resources
Signal — Meg’s year-long mentorship program
Define Your Foundations — Jessica’s six-month cohort
The Deeper Foundations Membership
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

[A note before you listen: This episode includes candid discussion of suicide, suicidal ideation, mental health crisis, psychiatric hospitalization, addiction, and chronic illness. Please take care of yourself — skip it, save it for later, or listen with someone.]
Failure is one of the only universal experiences in business, and it’s also the one we’re least willing to say out loud. Most of the time when failure does get talked about publicly, it’s been sanded down into a tidy redemption arc or it’s behind a paywall. Jess Manuszak decided to throw a party instead.
In this episode, we talk with Jess Manuszak, owner of the Denver copywriting studio Verve and Vigour and founder of The Failure Ball, a biannual black-tie event where people get on stage in gowns and crowns and tell the truth about how they failed. The Ball started in 2020 with a goal of 30 attendees, sold out at 78, and last year filled a Victorian mansion with 200 people. All profits go to To Write Love On Her Arms, because the connection between shame and suicide is exactly why the event exists. The next one is September 19, 2026 in Denver.
We talk about the difference between the failures we actually caused and the ones the online business world decided to call failures, why the format has to be in-person (and glamorous, and not under fluorescent lights), and how to know when your story belongs on a stage versus in your therapist’s office.
* Why shame festers when failure gets left in the dark
* The rule that a failure has to be one you actually caused
* Getting a job isn’t a business failure — but the industry treats it like one
* Why the format is a ball, not a summit, a conference, or a podcast
* The failure behind the failure: what speaker coaching actually uncovers
* “You don’t have to turn your trauma into content” — and how to know when you want to
* Knowing why you’re sharing: to feel less alone, to be witnessed, or to get input
* Where the line sits between authenticity as a human and your brand’s story
* Holding space for clients versus asking clients to hold space for you
* Why at least one Failure Ball speaker every year is actively failing, with no gold bow on it
“We know the psychology behind shame. We know that the antidotes to shame are community, non-judgment, sharing, and self-kindness. That’s really what we’re here for — drag your dark secrets into the light. You feel like they’re so dirty. Bring them into this room and you’ll see how squeaky clean they actually are, because I guarantee someone in this room relates. It’s the failure behind the failure. Everybody wants to be loved. If you’ve had a launch that failed, maybe everyone hasn’t lost a million dollars at launch, but everybody wants to try to have financial stability in their life. It’s those underlying threads that connect everyone and help heal that trauma — versus, for $27 in four installments, we will heal your shame for you.” — Jess Manuszak

Resources Referenced
The Failure Ball
Mike Ganino’s episode
Nicole Lewis-Keeber’s episode
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

We’re both getting pitched constantly by emails that clearly came from a bot that scraped our show notes, and the reason they don’t work isn’t the outreach itself.
It’s that there’s no distinct perspective behind it.
In this episode, we talk about the chicken-and-egg problem underneath developing a reputation and referrals: you need a point of view to get in the room, but you need to be in rooms with actual humans to sharpen a point of view. We get into why AI-workshopped positioning defaults to the average of what everyone else is already saying, what it actually takes to be referable, and how long it really takes for an angle to become something people seek you out to talk about.
We’re honest about the awkwardness of testing out your language with other humans and provide a “call me when” framework to help you sharpen your positioning for your network and for AI.
* The chicken-and-egg problem: needing a POV to get in the room, and needing the room to build a POV
* What it actually takes to be referable: category, persona, approach/angle
* The “Call Me When” exercise, and why specific scenarios are often clearer than results-based messaging
* Semantic vs. somatic: reading the face of the person you just pitched
* The “take your name off of your website” test
* Why “I could do that” is a trap, and how naming what you don’t do tightens your referrals
* The three-year timeline of turning a topic into inbound requests
* Being known for a feeling, not just a framework
* The linguistic throat-clearing AI adds, and how to cut 20–30% of it
“The perspective has to come first. The uniqueness, the differentiator has to come first. Because people are busy, inboxes are crowded, DMs are full of garbage, and if your pitch sounds like everyone else’s pitch, or if your website sounds like everyone else’s website, or if your email sounds like everyone else’s email, then I don’t care how many times you workshop it — I could take your name off of it and put someone else’s name on it, then I’m not gonna hire you. I’m not gonna bring you into my membership. I’m not gonna bring you on the podcast. You might be the nicest human alive, but if I don’t hear something different in your messaging, then I don’t know how to amplify your message.” - Meg

Resources Referenced
Angie Stegall - Coach
Sharon Wagner - Branding
Hillary Weiss Presswood - Campaigns
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

Most of us who work for ourselves aren’t one clean thing—we’re cartoonists who also teach, consultants who also write, coaches who also run the whole business. And after a couple decades of that, you can end up with an enormous body of work that almost nobody can actually see, least of all the AI tools now deciding who you are. To talk through what to do with a career’s worth of ideas, we’re bringing on Meg’s friend, colleague, and client, Jessica Abel.
Jessica is a cartoonist and author turned business coach for professional creatives, helping them finish the self-generated work that has no deadline and get paid well enough to actually have time for it. In this episode, she walks us through the very unglamorous process of taking 10-plus years of courses, newsletters, and frameworks, most of it locked behind paywalls or buried in podcast audio, and making it cohesive and legible for both people and AI. She and Meg get honest about why podcasting is great for ideas and terrible for discoverability, what it actually takes to update a Wikipedia page, and why The Guardian counts as proof but a marketing podcast doesn’t.
We talk about the difference between productivity and capacity, why “decide” and “reflect” are the phases everyone skips, and what it means to pay yourself first with your time instead of your leftover minutes. We get into cyclical burnout, idea debt, and the genuinely hard work of deciding what you’re not going to do—and being at peace with it.
* Why “multi-hyphenate” isn’t a bug of entrepreneurial life
* Cyclical burnout: what happens to someone who always has new ideas
* How Jessica consolidated a career-long body of work into something legible using a bottom-up, feedback-driven process (and Claude)
* Capacity as a lens—not just your time, but your neurological and emotional bandwidth—and why it fluctuates by the day and the season
* Grow work vs. build work, and the tension between expanding your audience and cementing a legacy
* What it actually takes to be legible online—AI discoverability, entity confusion, and why Jessica still shows up as a cartoonist first
* The Creative Engine’s four phases—collect, decide, act, reflect—and why decide and reflect get skipped even though they’re the shortest
* The “flexible container”: building a finishing structure with edges that can still absorb a sick kid or a health flare-up
"I actually hate the word productivity and try to not talk about myself as a productivity coach, because—I still have to use it a lot 'cause it's the word people know. But productivity literally means: how do you have the same amount of capacity and jam more stuff into it? How do you get more stuff out of whatever you have available? And of course you can look at it different ways, but that's literally what it means in the economic sphere. Which is just a point of view that doesn't work for humans, and especially creatives and people who have big ideas and are trying to do the self-generated stuff." —Jessica Abel

About our Guest
Jessica Abel
Out on the Wire
In the Weights
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

Aggressively Human went on hiatus for July, and we’re back to talk about what the break actually looked like!
In this episode, we catch up on what our month off actually looked like — Jessica’s West Coast “book tour” meeting Deeper Foundations members across four cities, and Meg’s glaucoma surgery and a quieter, more foundational summer of business work.
We talk about travel, illness, eye surgery, membership relaunches, and the discomfort of resting without immediately filling the space with something new — plus why a genuine pause turned out to be exactly what both the business and the podcast needed.
* Why Jessica took her book on an unofficial “tour” through Seattle, Portland, San Francisco, and LA
* The public transit challenge: one rideshare in twelve days across four major cities
* Meg’s glaucoma surgery, what a week without screen time actually looks like, and why she scheduled it for the slow season
* What it actually looks like to let go of “big, hairy, ferocious projects” for a season without the business falling apart
* Relaunching the Deeper Foundations membership without ever having done a formal launch sequence before
* The “collective pause”: a shared sense that clients, colleagues, and the industry at large all pulled back at the same time this summer
* Why reflection is the step that gets skipped in a weekly podcast cadence — and why that’s a problem worth solving
* The World Cup as a rare moment of monoculture in an increasingly fractured media landscape
* What “resting but not regenerating” feels like when travel and motion replace actual stillness
“I think sometimes when you’re in a production content creation process, you don’t have a chance for reflection. When it comes to podcasting, because of the weekly cadence, you’re always gathering ideas, lining up guests, and thinking about what you want to talk about. Then we have to get together, we have to record, we have to produce, we have to create the show notes — we have to do all these different things. And that fourth step, reflect, is the easiest one to miss, because the cadence has been determined, and we lose sight of what it is we’re trying to do here.” -Meg

Resources
Leaving the Casino
Just for the Summer by Abby Jimenez
Succubus Blues series by Richelle Mead
School of Moxie with Mary Williams
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