In this episode, we talk about a concept Jessica has been calling reputation harvesting, which as defined by Meg: Reputation harvesting is when you are reliant on previous work in order to have your current work be successful, without additional marketing activities to grow your list, expand your network, or evolve your way of thinking.

We walk through three scenarios where it shows up: businesses that sell one-time or beginner-level offers, businesses whose audience stays loyal but stops growing, and businesses that keep putting the same content in front of the same people for years.

We get into why discovery isn't free anymore, how your referral partners' business seasons affect yours, and how long you can realistically coast before the pipeline dries up.

• Three ways reputation harvesting shows up, and why each one needs a different fix
• Why one-time offers (websites, "start your business" programs) eventually saturate any network
• Distribution is either algorithmic or relational, but it isn't business as usual anymore
• Why mediocre, generic content gets lost in an AI-saturated feed
• How long you can coast depends on your business model: launch-based, referral-based, or leveraged offers
• When your whole referral cohort hits the same burnout season at the same time
• The difference between replaying, reinforcement, and actually evolving your thinking
• What "evidence of thinking" looks like: an architected blog, case studies, and a state-of-the-market update every six months
• You don't have to do everything at once: seasons for new thinking, new networks, and composting old work
• Meg's definition of reputation harvesting, and Jessica's metaphor of a reservoir with a drain at the bottom

"Your reputation is like a pool of water with a drain at the bottom. It can go down, but you have to bring it back up. But if it goes down too critically and it goes under the threshold of being able to pump water out, it gets harder. You can get by for a couple of seasons, but at some point it becomes too low to be operable. And then because it's so low, it's actually much harder to get that back up." - Jessica

Resources

• Relationship Rhythms
• Signal

Connect with Us

Meg Casebolt

Jessica Lackey

Meg recently revived her old solo podcast feed as Love At First Search, a show about how experts become easier to find, understand, trust, and recommend across search and AI.

Since those questions overlap with a lot of what we talk about on Aggressively Human — especially visibility, expertise, marketing, and building a business without endlessly feeding the content machine — we’re dropping the first episode into this feed as a little cross-pollination.

In “AI Discoverability for Experts: What Modern Search Rewards in 2026,” Meg breaks down what’s actually changed about search as AI-generated answers become a larger part of how people find information and choose who to trust.

The big shift: search is no longer only evaluating individual pages and deciding which one should rank highest. Increasingly, AI systems are trying to understand sources, expertise, ideas, and relationships across a larger body of work so they can synthesize an answer.

That changes what “being findable” means for experts.

In this episode, Meg covers:

• why ranking a webpage is no longer the whole job
• how AI search evaluates sources and expertise differently from traditional search
• why clear, explicit expertise matters more than simply publishing more content
• what zero-click search changes about how we measure visibility
• why being recognized by AI is not the same thing as being recommended
• which SEO fundamentals still matter even as the search experience changes

If this is your kind of nerdy rabbit hole, you can find more episodes of Love At First Search on Apple Podcasts, Spotify, or wherever you listen to podcasts.

Listen to the original episode + show notes:

https://loveatfirstsearch.com/love-at-first-search-podcast/search-changed/

Love At First Search / AI Findability Library:

https://loveatfirstsearch.com/ai-library/

And if you’re here for Aggressively Human, don’t worry — Meg and Jessica will be back next week with a new episode about audience growth, stagnant marketing, and how often you actually need to change what you’re doing.

Aggressively Human housekeeping

Aggressively Human has also moved podcast hosts.

If you were following through Substack, the existing feed should continue working, but the safest way to make sure new episodes reach you is to follow Aggressively Human directly in Apple Podcasts or Spotify.

You can always find the newest episodes and show notes at:

https://aggressivelyhumanpodcast.com/

In this episode, we tell the story of how Aggressively Human almost wrapped up. Jessica ran her own Committed Capacity Calculator, realized there was no room left for the creative projects she wanted to pursue next, and sent Meg a hard email right before Labor Day weekend. After the weekend (leaving Jessica in limbo!), Meg took her dog for a long walk, worked out what would actually be lost if the show ended, and came back with a counteroffer over a late-night Voxer exchange that felt like a high-stakes negotiation.

We talk about why we’re switching to a biweekly cadence with fewer guests, what Meg found when she ran two years of our transcripts through a research process, and why predictability still matters even when you slow down.

• How a capacity calculator turned into a “something’s gotta give” moment
• Writing (and receiving) the hard email: giving each other space to process instead of reacting
• “What would be lost?” — why the guest interviews weren’t the irreplaceable part, but our conversations were
• Thought partnership in public, and why it’s different from content made to sell
• What 920,000 words of transcripts showed about our intellectual fingerprints, and how our guest ratio shifted from about 60% to 30–40%
• Moving from “business in the age of AI” to what we’re actually building toward
• Why Jessica is a bad cold interviewer, and why fewer, deeper guest conversations make sense
• “I don’t care about the algorithm. I don’t want to break the habit.” — predictability as a form of trust
• What’s next: every other Thursday, a dedicated recording slot, and both of our new solo podcasts (Meg’s is here at Love at First Search on the platforms, Jessica’s is coming in 2027).

“What’s the gold? What do we already have that we want to do more of, instead of following someone else’s rule book that says, ‘Here’s how it’s supposed to go’? And the aggressively human way to podcast is to slow down, to do less, to rely on what we’ve already created, and to sharpen up our way of thinking so that it’s unique to us and that it’s valuable to both of us without it being extractive.” - Meg

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

In this episode, we talk with Darnell Brown, a self-described creative polymath, brand strategist, and copywriter, and the founder of Forge, a virtual community for multi-passionate entrepreneurs built on the idea that everyone in the room is a co-equal expert. Darnell has been an entrepreneur since 2008, and now that Forge is three years in, he’s learned a lot about what it takes to keep a community going.

We compare notes on how our three communities actually run, including Forge’s expansive, experiment-everything approach versus Jessica’s more focused, curriculum-driven membership. We dig into onboarding, celebrating wins (and bad weeks), and the part almost nobody plans for: how people leave.

* How Darnell went from drawing superheroes at age five to graphic design, brand strategy, and storytelling

* Why “creative polymath” is a clear position without a known category

* Expansive communities vs. focusing communities

* Treating community like a perpetual housewarming party: meet people at the door, take their coat, and let them choose which room to explore

* Low-friction onboarding: interactive standards, a little gamification, and paths based on how often people plan to show up

* The host’s dilemma: when you’re always watching the door, you never get the deep conversation (and why the founder doesn’t have to be the host)

* Building a culture of celebration, including weekly wins and the “inverse highlight reel”

* Leading with translucency: sharing what didn’t work without giving up your authority

* Why off-boarding deserves as much attention as onboarding, and how to make peace with members who ghost

* A positive exit makes people more likely to come back (30% of Meg’s first launch after her pivot were returning clients)

“A community experience for adults should feel a lot like a perpetual housewarming party. And the thing that I’m thinking all of the time when a new member comes in is: if this was in the real world and I was welcoming them into this mansion, how would I treat them? I’m trying to do the virtual version of meeting you at the door, asking ‘Can I take your jacket?’ and walking you to the most popular room in the house, which is usually gonna be the kitchen or the living room, ‘cause that’s where the conversation’s already happening. But I also want to show you the rest of the house and the different layers. And you might not be interested in that, depending on your personality. You may not even have come for that part of things.” - Darnell

About our Guest

Darnell Brown

Forge

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

In this episode, we talk with Eleanor Mayrhofer, a digital strategist and web designer who helps people and organizations that regularly publish ideas consolidate, streamline, and showcase their work online. Eleanor came up through design school and the Web 1.0 boom, spent more than a decade in UX and global methodology work at Publicis Sapient in Munich, and now works with executives, academics, novelists, and think tanks who are great at what they do and have no interest in learning Claude Code.

We get into why the website is usually just the presenting symptom, how Eleanor matches a distribution plan to someone’s temperament, and why she still builds on Squarespace while getting excited about Claude Design for mockups. We also talk about AI copy flattening niche expertise, what book design teaches you about websites, and the two domains everyone should buy today.

* Why “I need a website” is often the presenting symptom of a bigger digital strategy problem

* Matching the platform to the person: a blog for the contemplative exec, philosophy talk radio for the professor, a Substack for one specific think tank project

* Eleanor’s six-ingredient recipe: goal, positioning, brand, platform, content, and distribution network

* “Posting my head off on LinkedIn and nothing’s happening,” and what to build instead

* Squarespace, WordPress, and vibe-coded sites: which ones your clients can actually maintain

* How AI copy struggles with niche jargon, contested terms, and human stories

* AI raising the floor on design while squashing the ceiling, and what book design teaches about structure and hierarchy

* Buy your name. Buy your book title. (Or Meg will, just to mess with you.)

“If you have this think tank, you need to build it out as a website. It’s like you need to showcase what you can do, and then you need to find bigger publications and point them to that body of work, and then write for those publications. “I’m posting my head off on LinkedIn, and nothing’s happening.” It’s like, well, nothing is gonna keep happening. You need to just have this infrastructure to show to the right people and be able to point to those.” - Eleanor

About our Guest

Eleanor Mayrhofer

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

In this episode, we look back at our fall launches. Last month we walked through what we planned to launch, and both of us ended up pivoting partway through. Jessica walks through a membership price increase, about 60 welcome calls, a cohort that filled 15 of 20 seats, and the realization mid-launch that the membership—not the cohort—had become the place to actually define your foundations. Meg shares why her Signal launch came in at 11 people instead of 15 to 20, what she’d change about her small group workshops, and why she’s moved away from low-cost public challenges.

We talk about readiness, longer decision timelines, hand-selling, and why the best-fit buyers this time came from people who’d been engaging with our work for months.

* “Which launch?” Juggling a membership price raise, a member cap, and a public and private cohort at the same time

* When your product suite changes on you in the middle of a launch

* Why almost everyone in Jessica’s cohort had already read the book, joined the membership, or taken a course

* Meg’s small group workshops, and how benchmarking can feel like “now I know what to do”

* Why low-cost, high-volume public challenges stopped feeling good

* Readiness over budget: why buyers are fewer, slower, and more discerning

* Follow-up matters more than the sales sequence, and what personal outreach looks like at this stage

* Selling integration and discernment, not just information

* The staggered launch: why the people buying now first heard from you six months ago

“It used to be that the conventional launch strategy was get people on your newsletter six to eight weeks before the launch, have some webinar content, and then sell. And I think what you and I are both discovering is that they need to engage with you and your work six months in advance. They need to understand your way of thinking, not just through newsletters, but through live content, through engaging with your work for a substantially longer period of time. So your launch is really a staggered launch. The people who are joining now, you actually launched to them six months ago in the spring.” - Jessica

Programs

Deeper Foundations Membership

Signal Mentorship

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

For the second episode in our series on voice, we welcome back developmental editor and writing coach Samantha Pollack. Sam runs Indie Copy Studio and works with business owners, authors, and academics who share a healthy side-eye for anything artificial, and she explains what developmental editing looks like when it’s applied to sales pages and emails instead of manuscripts. Her answer to “how do I know what I sound like?” is refreshingly unglamorous: you have to write a lot before you can hear it.

We talk about why writing to format is how the internet got so much slop long before AI showed up, and the difference between writing to get something from your reader and writing to give them something. Sam also makes the case that reading fiction, and even Hamlet, might be the most useful homework a business owner can take on.

* Why “is AI good at writing?” is the wrong question, and what to ask instead

* What a developmental editor actually does, and how that applies to a sales page

* Why you can’t find your voice before you’ve written enough to see it

* Spotting a writer’s signature quirks, and knowing when they tip over into a gimmick

* Writing as craft vs. writing to format: how LinkedIn templates and 2016-era copywriting formulas gave us slop long before AI

* Free-writing prompts that get you out of outcome mode (starting with “tell me the story of an object on your desk”)

* Writing to get vs. writing to give, and the “empathy switch” that keeps flipping mid-draft

* Why reading outside the business bubble, especially fiction, makes you a better business writer

* Why “I only use AI to edit” is riskier than it sounds if you don’t know how to edit

“There are people who will be like, ‘I don’t use AI to write, I just use it to edit.’ And that makes my little editor heart cry, because if you don’t understand how to edit writing, you’re not gonna be able to discern whether or not AI did a good job. And in your mind you’ll be like, ‘Oh, this looks fine,’ because objectively it will look fine. It will be grammatically correct, it will have some kind of varied rhythm. It’s just gonna feel flat and hollow because it isn’t basing anything on a feeling. When you read writing, it creates a feeling. And that’s why AI writing sounds like AI writing, because you don’t feel anything when you read it.” - Sam

About our Guest

Indie Copy Studio

Anarchy on the Blank Page

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

In this episode, we talk with brand voice expert Justin Blackman, creator of Voice Finder and the Verbatim tool, about what brand voice actually is and how to find yours. Justin breaks it down into three things you can measure: vocabulary, cadence, and tone. He explains why AI copy drifts toward the average of every human on the planet, and how he pushes clients to defend each word they use to describe themselves until it earns its keep.

We get into Latinate versus Germanic words, why AI and copywriters both write shorter sentences than most people, and what separates optimistic from confident on the page. We also compare what ChatGPT and Claude say our own brand voices are, and hear about the GIF that took Justin an hour to choose.

* The phrases that give AI away: “where the center holds,” “load-bearing,” closing the gap, “it’s not X, it’s Y”

* Justin’s three measurable parts of brand voice: vocabulary, cadence, and tone

* Why jargon and insider language can be a feature when they attract the right people and repel the wrong ones

* “Friendly, human, and casual” as the trifecta of nothingness

* Latinate vs. Germanic words, and why “prickly” lands differently than “deflating”

* Building a vocabulary theme from your background, from roots-to-fruits and broadcast signals to Indiana Jones

* Why AI sentences run shorter than most human writing, and how that’s changing the way all of us write

* Why a book written like an email is so hard to get lost in

* Optimistic, hopeful, or confident? How each one changes the words you put on the page

* What your GIF choices reveal about your brand voice

“If you ask most people, and just about damn near every brand on the planet, what they sound like, they’re gonna default to the same thing. They’re gonna say friendly, human, and casual. It’s the trifecta of nothingness. It’s in damn near every brand voice guide I’ve ever seen. Friendly is more of a personality. It’s the way that you show up. It’s what you do for people. It doesn’t define how you talk.” - Justin Blackman

About our Guest

Justin Blackman

Voice Finder

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

In this episode, we talk with Tanisha Tate Woodson, who runs Woodson Insights Research and Evaluation, working with nonprofits, government agencies, and funders to humanize data and show the impact of their work. She walks us through her approach: four dimensions that get dialed up or down for every engagement, culturally responsive methods that let people tell their stories the way they actually want to, and a sense-making session at the end so the report doesn’t die on a shelf.

Then we get into what having a method has done for the business. Tanisha’s RFP win rate is around 50% in a field where 15-20% is normal, because she’s bidding on one or two instead of five and can answer a proposal from a process she’s already written down. She built an AI skill that knows her red flags and tells her when to pass. And she’s growing on referrals and community relationships with limited social media presence. This is a meta episode — premise, method, methodology in action.

* Storytelling as data: why observation and conversation are data, not just spreadsheets

* Why funders and the nonprofits they fund are speaking two different languages

* Research done to communities vs. research done with them — and the harm history behind the suspicion

* Why every engagement ends with a two-to-three-hour sense-making session, not a report on a shelf

* The through line from a promise made to a community to an artifact that actually goes back to them

* The four dimensions that get dialed up or down for every client — and the myth that community-engaged work is less rigorous

* Culturally responsive method in practice: PhotoVoice, video, and a focus group built on Chutes and Ladders

* Building the Black Data Pulse panel so recruitment stops eating clients’ budgets

* Why a codified process doubled her RFP win rate — and how she decides what not to bid on

* Using AI as a trained junior team member, not a proposal generator

* Growing a business on relationships and referrals with no Instagram account

* What “know yourself first” has to do with whether your AI output sounds like you

“There’s a huge myth in the field that when you’re close to the communities, when you’re doing community engagement work, it’s no longer rigorous, and that’s not true. It’s more rigorous because now we’re embedding community perspectives into their work. We’re not only embedding them into the work, but we’re also articulating the cultural relevance of the work that we’re doing.

Are people telling the stories in a way in which they wanna be told? So if, for instance, if you wanna hear from students, do students wanna take a survey? No. So we think about the culturally responsive methods as also thinking about who you wanna hear from and how do they want their stories to be told.” - Tanisha Tate Woodson

About our Guest

Woodson Insights

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 with Laura Lopuch, who helps online service providers start conversations with high-quality leads through cold outreach. She built the WARM framework and the Warm Client Method, and her whole argument is that the leads you want are already out there leaving public signals about the problems they have—you just have to do the research before you hit send.

We talk about what qualifying someone actually looks like from the outside, how to name a prospect’s blind spot without insulting them, why “are you interested?” is a better ask than “book a call,” and where the follow-ups fit. We discuss the reality of dealing with inbox overwhelm, how to stand out from the volume of terrible cold outreach, and why outreach isn’t just for prospecting.

* What a cold email actually is—and why the transactional “buy my stuff” version is a myth

* Gap signals: reading the public evidence that someone has the problem you solve

* How to infer budget, team size, and urgency before you ever send an email

* Naming a blind spot without negging—using outside research instead of “your brand is bad”

* Consent-based outreach and why “are you interested?” is the right-sized ask

* Micro-yeses in the email vs. escalating-commitment persuasion tactics (they’re not the same thing)

* Fast burn vs. slow burn: sales emails, podcast pitches, collaborations, workshops, JVs, sponsorships

* Whether this works for B2C and coaching, not just B2B services

* Laura’s actual numbers—reply rate, conversion rate, and why the wins live in the follow-ups

* Why the low bar in everyone’s inbox is good news for anyone willing to sound like a person

“A lot of people get confused when I say relevant, and they're like, 'Yeah, first name, company.' And it's not actually that. That's personalization. That's icing on the cake. The relevancy is the deeper method of tapping into what is this person's existing goal? What are they working towards? Are they working to sell their agency in five years? If so, they need a controllable source of getting new clients in the door, one that doesn't depend on algorithms.” - Laura Lopuch

About our Guest

Laura Lopuch

The WARM Client Method

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

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

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

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

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

In this episode, we get into what’s behind our summer sabbatical: the planning required to step away (turns out you have to prep in advance), why listenership naturally dips in the summer, and why we decided against reposting old episodes under a “best of” label. Meg talks about her seasonal rhythm—short summers in a cold climate, kids’ camp schedules, less desire to sit at a microphone—and Jessica walks through a stretch of heavy travel, a meaningful family transition, and finally having the room to take a real beat.

We talk about the difference between maintaining and growing, why a body of work keeps earning for you even when you slow down, and the case for “mental composting” as actual business strategy. We also get into relationship marketing that doesn’t look like marketing, and why taking time off doesn’t mean you’re bad at your business. Plus a live tarot pull that may or may not predict another book.

* Why we’re taking all of July off—and why it’s a sabbatical, not just a slowdown

* The prep it actually takes to step away (hint: start two to three months out)

* How summer listenership shifts when everyone’s out living their lives

* Meg’s seasonal rhythm: cold-climate summers, camp schedules, and working less on purpose

* Jessica’s summer of travel, a family transition, and finally taking a beat after years of building

* Why a “body of work” keeps working for you when you stop pushing

* Mental composting and the case for creative downtime (see: Lin-Manuel Miranda in an airport)

* Maintaining vs. growing—and why you don’t always have to be in growth mode

"Taking time off doesn't mean you're bad at your business. But it does mean that if we're going to take time, we need to prepare for that two to three months in advance. Otherwise it's that vacation-y feeling where you cram.

I don't have a whole bunch of curriculum that I'm creating. I'm not writing and launching the book. I'm at a place where I can take a beat, so I'm gonna take it. Past Jessica did a good job, present Jessica is gonna take advantage of that, and future Jessica already knows what she's doing in August and September. There's more launches coming. They're just not happening in July." -Jessica

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

In this episode, we talk with Nikki McKnight—Meg’s romance-podcast co-host, operations expert, and newly minted Certified Customer Experience Professional—about why she niched her business down into customer experience and launched a new business podcast called Would Recommend. Nikki walks us through how she went from “I can do everything” operations work to building a practice around a single belief: that for founder-led businesses, customer experience is the best marketing and retention strategy there is.

We dig into the difference between customer experience and customer journey, why emotions are what actually drive referrals, and how matching your brand promise to your real experience builds (or breaks) trust. There are frameworks—Nikki cannot help herself, and neither can we—but mostly it’s a conversation about the gap between what we say we deliver and what it actually feels like to be on the receiving end of it.

* Why Nikki niched down in belief rather than service or audience—and why that’s easier to sell and refer

* The customer experience pyramid: satisfaction → ease → enjoyment—and why advocacy only lives at the top

* Customer experience vs. customer journey: “the journey is a lane, the experience is the whole highway system”

* Why emotions create memories, memories create perception, and perception is the only thing that drives behavior

* Brand promise as an operational standard (not a mission statement)—and why you can control your promise and experience but never your customer’s perception

* The Mr. Rogers writing rule that changed how Nikki thinks about every email, sales page, and support reply

* Category expectations: how to spot what customers already assume about you—and deliberately disrupt it

* Giving your customers the language to refer you (because “you just need Nikki, go” doesn’t convert)

* When great delivery meets AI-generated marketing—and why a mismatch quietly destroys trust

* Principles vs. methodology, and why lead magnets built on tactics expire the moment the platform changes

* CX train wrecks (yes, QuickBooks and Canva, we’re looking at you) and reporting “from the scar, not the wound”

“Your whole job is to create memories. Because if you can elicit an emotion in someone, emotions are what create memory. When someone creates a memory, then they have a perception of something, and it’s perception that drives behavioral change. You can’t just jump straight to a behavioral change.

And customer experience is not just what starts when someone pays you. It’s not the customer journey. The journey is a lane. The experience is the whole highway system.” - Nikki McKnight

About our Guest

Would Recommend (Nikki's new podcast)

Unreasonable Hospitality by Will Guidara

CCXP – Certified Customer Experience Professional designation

Acceleration Strategy Inc. (12-week customer experience program, Toronto)

Fixable with Frances Frei and Anne Morriss (the Southwest episode)

Derek Thompson's podcast: the NBA / Adam Silver episode

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

In this episode, Meg breaks down entity-focused search and discoverability: the shift from optimizing the domain versus optimizing the entity and the person. She explains what an entity actually is (think of it as a star in a constellation, or a suspect on a murder board with red strings connecting everything back to you), and why so many of us have fragmented, disconnected, or missing entity signals without realizing it. This is the same material that opens her Signal mentorship, compressed into one conversation.

We talk about why your full name needs to be on your website, what schema markup does and why it’s suddenly mattering again, and the difference between work you control (your own pages and copy) and the third-party validation you can’t fully control but absolutely need. This is the first step of the slow, compounding, multi-month play—and why the work pays off even if the AI citations take their sweet time to show up.

* Why “it’s not just Google anymore” changes everything about how you get found

* What an entity actually is—person, book, program, company—and how they connect like a constellation

* The three most common problems: missing entities, disconnected entities, and entity fragmentation

* Why Meg’s own podcast and business weren’t connected in the AI knowledge map (and how she fixed it)

* The copywriting habit that’s quietly hurting you: all client-facing language, no expertise or “who I am”

* Schema markup explained in plain English—and the “Same As” code that ties your whole body of work together

* How to narrate a pivot so AI (and humans) know you’re the same person who changed

* Why you can build a perfect entity and still not get recognized without external validation

* The referral guide idea: a “call me when” doc for both the humans and the machines

* How long this really takes—and why Perplexity shows changes before ChatGPT ever will

“We get to signal that we would like things to be entities, but we do not get to decide which are the entities that are recognized. So, Jessica Lackey already exists in the knowledge map. We know that because if you go to ChatGPT or Claude or Google and say, ‘Who is Jessica Lackey?’ there’s an answer there.

But unless you are super clear about this is what I want you to do, AI can pull from anywhere. So if you wanna be more in control of how you’re represented and the language that it’s using about you, then you need to be clearer about how you want to be defined.” -Meg

Resources

Signal Mentorship

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Meg Casebolt

Jessica Lackey

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

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 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

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 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 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

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

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

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 is a Pricing Strategist and the creator of the Package Matrix™. She is the founder of Web Designer Academy, where she spent a decade helping women web designers move from undercharging to premium pricing - and where she developed the Package Matrix™ framework now used by service providers across industries. Learn more about the full framework at https://shannonmattern.com/package-matrix

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, Amelia shares what led her to a significant decision at the end of 2025: scaling back her podcast studio Softer Sounds dramatically and putting herself on a six-month sabbatical for that side of her business while investing in the creator-style side of Off the Grid. We dive into the idea of self-employment as a spectrum, the many forms it can take across a career, and why moving along that spectrum is a feature, not a flaw.

Hear from all three of us how we cobbled work together to build the income we needed across the years — the bridge jobs, the clients who weren’t the dream but paid the bills, and the years of audience-building that often preceded any real traction. This isn’t a conversation about how to build a six-figure business. It’s about what self-employment actually looks like at different stages, and what we’d do differently if the goal is to simply stay self-employed.

* What Amelia’s six-month sabbatical actually looks like — and why she chose a third option instead of hustling harder or closing the studio

* Self-employment as a spectrum: from side contracts and bridge jobs all the way to full-time business ownership (and back again)

* How Meg, Jessica, and Amelia each cobbled things together to get started — and what cobbling it together still looks like for established businesses

* The role of bridge work in creating the time and mental space to build what you actually want long-term

* Why Amelia chose to focus on Off the Grid and The Interweb instead of doubling down on Softer Sounds

* What publishing books (Amelia’s and Jessica’s came out within a week of each other in October 2025) has to do with long-term business strategy

* Hitting your capacity ceiling — and the different forms it takes at every stage of growth

* Authority building: why showing up consistently before a trend breaks is what actually creates leverage when the trend arrives

* The privilege question: how partner income, healthcare access, and life stage shape what risks you can realistically take

* When and why to go back “in-house”

“The only consistent business models you can count on are being a CPA or owning a funeral home. Otherwise it’s gonna change all the time. If you wanna be self-employed long-term, you have to love the ride of it. You have to love that it changes all the time. Do you enjoy every moment of it? No, I do not relish in the fact that AI perhaps stole half my business. I don’t have to love that. But I have to love dusting myself off and doing something new again.” - Amelia

About our Guest

Your Attention is Sacred Except on Social Media

Off the Grid

Self-Employment is a Spectrum

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 the difference between being tired of something in your business and being done with it. We dig into the natural cycles of building — preparing, planting, harvesting, and resting — and why the reinforcement phase (the one that actually creates momentum) is the hardest to stay motivated through. Jessica shares what it’s like to be in the “hardening the cement” stage while wanting to chase something new, and Meg talks about her experience running Social Slowdown for 100 episodes and knowing when it was time to hand off the torch.

This isn’t a pep talk about pushing through or a permission slip to quit. It’s a conversation about learning to read the signals your energy is sending you.

* Why the repetition phase of your business feels boring but is where the real traction happens

* The seasonal cycles of energy and creativity (and why Meg doesn’t launch anything in February)

* Jessica’s harvest-to-reinforcement arc — and the tension between solidifying old work and chasing new ideas

* The green light / yellow light / red light framework for deciding when to push, pause, or stop

* Why your audience hears your message differently every time, even when you’re saying the same thing

* How Meg knew it was time to retire Social Slowdown after 100 episodes and a book

* The difference between reinforcing, repurposing, remixing, and just regurgitating your content

* What to do when you still need to market but have nothing new to say

* Why your best referral partners being in the same slump at the same time is a real business risk

How relationships and referral networks carry your message when you can’t

"Reinforcing is going back in and putting more infrastructure in place to make it stronger. Repurposing is, or rehashing for that example is taking the same information and pushing it out in a different place. Remixing could be finding new ways to explain something." — Meg

Mentioned

Amelia Hruby/Off the Grid

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 explore the difference between hosting a podcast and leading a movement. We talk about the three types of motivations for a platform: the desire for fame, the intentional choice to lead with a platform, and the moral imperative—when you have something to say that no one else is saying.

This is a conversation about the reluctant responsibility that comes with showing up consistently, having strong points of view that shapes the discourse, and being willing to change your mind as you learn more.

* The three motivations for creating a platform: fame, leadership with a platform, and moral imperative

* What we can learn from Hamilton and Burr, especially why “I want to be in the room where it happens” is different from creating the authority to create the room.

* Creating into the void—the lag time between creating content and seeing its impact

* What changes when people start quoting your work back to you

* Why reluctance to lead (because you want to get it right) is an act of integrity

* The responsibility of being a standard bearer when people you looked up to aren’t active in the space anymore

* How compounding authority works over time

* The difference between selling services directly vs. articulating a point of view

* Why having strong points of view while staying open to changing your mind is so hard

“I think that when you’re a movement leader, you have to be willing to walk on the ledge more publicly for much longer. With less feedback than you anticipate.” - Jessica

Resources Mentioned

Antimemetics

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’re talking about what’s actually happening on social platforms in 2026, especially for expertise-led businesses that don’t want to become full-time media companies.

We talk about the TikTok effect, discovery-driven algorithms, and why entertainment now beats education on most feeds. Andréa shares how she thinks about social media today, how she uses it in her own business, and where it fits alongside other channels like podcasts, newsletters, websites, and SEO. We also talk about why viral content often fails to translate into clients, and how people really decide who to hire.

This episode is an honest discussion at where social media sits now in a broader marketing mix—and what expectations make sense to have if you’re still showing up there.

* Why social media feels louder, faster, and less useful than it used to

* The “TikTok effect” and how it changed every platform

* Discovery algorithms vs. follower-based feeds

* Why entertainment content outperforms educational content

* How engagement has declined across most platforms (and what that means)

* Why viral posts often don’t translate into revenue

* What Andrea puts in place before social media matters

* The role of podcasts, newsletters, websites, and SEO

* Local vs. national businesses and how discovery actually works

* Why repetition builds trust (for humans and AI)

“It takes a lot more effort for someone to leave that video or leave that post and go somewhere else to then do something else, like sign up for a newsletter or purchase something. So that sales cycle has gotten astronomically longer.

And so I'm not saying social media isn't important. Especially for me, it's a great networking tool. However, it's not, and as far as the hierarchy goes, it's just not as important as other marketing assets. And so I had to shift the way that I think about that.” -Andréa

About our Guest

Website

OnlineDrea on Instagram

Mindful Marketing Podcast

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

Is the course bubble over? Will AI shut down courses? Or is this just an industry hot take to get clicks and views?

In this episode, we talk about what’s actually happening with courses right now—and what’s not. We look at why self-guided, evergreen courses worked for so long, why they’re struggling to convert and retain attention now, and how AI has sped up changes that were already underway. We talk about how this has shown up in the various evolutions of our own businesses. We also talk about where courses still make sense, where they don’t, and why people are increasingly unwilling to pay for information without context, support, or application. (A multimedia interactive experience as Jessica called it in corporate-speak).

This isn’t a declaration that courses are dead. It’s a conversation about saturation, economics, attention, and what people actually want help with in 2026.

* Why course closures are becoming more common

* The difference between a bubble bursting and a market maturing

* What made evergreen courses work in the first place

* How rising ad costs and shrinking arbitrage changed the math

* Why beginner-level education scaled—and why it hit a ceiling

* What AI replaced almost instantly (templates, boilerplate, generic content)

* How Meg and Jessica have both surfed the wave of courses, both as leaders and as students

* What people still pay for (and what they won’t)

* The problem with “lifetime access” promises

* Courses as one piece of a broader ecosystem, not the whole business

“If you have a giant course where you promise to do everything, then you can’t do all of it well. And I think people are getting a little bit tired of like the survey courses, like the freshman 101 course of everything, or maybe those still exist. And I’m just out of the world view where I’m paying attention to them. But anytime that you have an all in one solution, whether that’s a course or a piece of software, or a coach who says that they can help you with everything, that breadth is going to prevent depth.

And if you want to learn something deeply from a person who understands it and can answer your questions when things go wrong, then that’s when you want to find an expert who teaches one thing really well instead of 10 things mediocre.” - Meg

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 spend a lot of time on what’s broken in business media: pay-to-play outlets, thought leadership that’s really just a sales funnel, and the absence of honest stories about what it’s like to run a small, durable business. Lex explains why journalists aren’t filling that gap, why solo businesses have a hard time surfacing interesting angles, and why so much valuable knowledge stays trapped in private conversations instead of becoming public learning.

The conversation also gets practical. We talk about subscriptions versus memberships, why Revenue Rulebreaker is a media brand and what does that mean, and how sponsorships, subscriptions, and community-adjacent networks can coexist with (or sit alongside) client work. Underneath it all is a bigger question: what would business culture look like if we treated podcasts, newsletters, and blogs as media—not just marketing?

* How Revenue Rulebreaker started as a personal experiment and became an indie media publication

* Why solopreneurs and micro-business owners are ignored by mainstream business media

* The collapse of traditional journalism and what it means for business coverage

* Why pay-to-play outlets distort whose voices get amplified

* Why having an “angle” is how stories get platformed

* The difference between thought leadership, marketing content, and media

* The problem with content that always has to sell something

* Subscriptions vs. memberships—and why Lex is intentionally avoiding a membership model

* How sponsorships and subscriptions actually fund indie media

* Why private experiments inside small businesses are some of the most valuable stories we never see

* The role of community, networks, and stewarded spaces in a post-algorithm internet

“Journalists previously who would have been sourcing those stories don’t know a lot of business owners, but they know the woman who started Spanx.

So they’re just not that working that hard to find stories. So if they don’t know any business owners, and you don’t pitch them a compelling story, that story’s not getting told. I think also business owners have a really hard time understanding what’s cool and interesting about their own business.

Like, you know, they’re like, “I’d like to have my business platformed.” Of course you would, but you don’t have an angle? What’s your perspective? Why are you doing this interesting thing? You have to really dig at them to find those interesting things.” - Lex Roman

About our Guest

Revenue Rulebreaker

Become a Legend

Lex Roman on LinkedIn

Mentioned Resources

Cal Newport - Can Substack Save Journalism?

Antimemetics

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 what we’re calling the expert’s paradox: why people with real experience often struggle to publish clearly, while less-experienced voices seem perfectly comfortable shipping simple advice. We see the seven-part blog post that will take 21 hours to write, and know we can’t stop with the simple AI-generated “5 simple tips” framework. We look at how this shows up in content, marketing, and tool recommendations—and why experts tend to freeze once they can see all the nuance at the same time.

We talk about the Dunning–Kruger effect, the difference between tutorials and diagnostic thinking, and how to deal with the pressure to finish the entire framework before saying anything publicly. We also talk about what helps: publishing before things feel complete, letting ideas change in public, and using content as a working asset rather than a polished performance.

And hear Jessica use the question “what’s the best CRM” to map out a content strategy in real-time, and Meg and Jessica compare chemistry (we think?) to your content organization philosophy.

* Why having more experience often makes it harder to say anything short, clean, or publishable

* How we can use our content for reinforcement, not repurposing

* A Clarion Call for Expertise with “Zippie Nickie and Gnarled Bart” from Corey Wilks, Psy.D.

* Why experts feel pressure to finish the whole framework before sharing anything

* Why tutorials are easy to ship and diagnostics are slow (and why that matters)

* How publishing your work and getting your language out there changes what people search for

* Why clarity wins out over volume in 2026

* How you can use blogs and long-form content as living, updateable assets

* Content architecture: collections, pillars, and making old work findable again

* Our voice choice and how does that influence your authority

“If you have something interesting to say that you feel is different from what else is happening in your industry, that is not a sign that you are outside of the norm; that is a sign that you see something that the beginners don’t. But you cannot be cited, credited, claimed, unless you put it out into the public sphere for indexing, for retrieval, for somebody else reading it. And you can’t change the discourse if you’re not part of the discourse.” - Meg

The Expert’s Paradox by Meg Casebolt

A Clarion Call for Expertise by Corey Wilks

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

But we have thoughts on traditional goal setting. In this conversation, we talk about how outcome based goals are often ineffective (and the fast path to burnout), and instead focusing on what’s in our locus of control.

We talk about the difference between “bottoms up” and “top down goals”, and how your stage of business and business model informs what matters. You’ll get to hear Jessica get on her soapbox about “10x is easier than 2x” goal setting, and hear us talk about how physics informs our approach to goals.

Plus hear OUR goals for 2026 — and most importantly, what we’re not doing this year.

* Why we both hate most New Year’s goal setting advice

* Outcome goals vs. output goals—and why the difference matters

* How goals fail when they ignore where you’re starting from

* Why revenue goals aren’t fully within your locus of control

* The problem with “just do more” as a strategy

* Force, leverage, and friction: three ways to change results

* How vanity metrics create performative productivity

* Saying no as an essential part of goal setting

* What we’re each choosing to focus on—and what we’re actively letting go of this year

Resources

Jessica’s 4 Part Planning Series

Meg’s Consistency Beats Virality (even When You Go Viral)

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

Who doesn’t want to fit in to their local entrepreneurial communities—but how many communities miss the mark, especially for solopreneurs and expert-led businesses? We’re joined by Raven O’Neal, co-founder of Startup Women NC and founder of Savvy Gal Media, to talk about what actually keeps a community alive once the initial excitement wears off.

We talk about what Raven has learned building a local community: how most ecosystems are designed for scalable startups, not people selling expertise; why solopreneurs often don’t fit anywhere cleanly; and why “more members” often makes things worse, not better. What surprised Raven most wasn’t a lack of resources—it was how fragmented they are, how little they talk to each other, and how much invisible labor it takes to hold people together.

This conversation also names the uncomfortable truth underneath community-building, both IRL and online: it’s real work, often unpaid, and frequently taken for granted. We talk about the politics of funding, the myth that collaboration is easy, and why intimacy, continuity, and clear leadership matter more than growth.

* Why most “community” spaces collapse once they try to grow

* How startup ecosystems quietly exclude solopreneurs and expert-led businesses

* What Raven learned building Startup Women NC—and what surprised her most

* The difference between social mixers and real, sustaining community

* Why fragmentation (not scarcity) is the real problem in local ecosystems

* The unpaid labor required to organize, host, and maintain community spaces

* How Raven’s work on Hacking the Patriarchy informs her approach to power, labor, and voice

* Raven’s word of the year and how that’s informing her building plans (PS - It contains a lot of cursing)

We actually had a meeting where we asked what does growth look like for this group? And a lot of our members said, one thing I love is how small it is. Like how much smaller it is and how intimate our meetings are and how much attention they get and how they’ve gotten to know each other.

About our Guest

LinkedIn

Savvy Gal Media

Hacking the Patriarchy Podcast

Fem Led News

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

For our first episode of 2026, we’re sharing the behind the scenes of two milestones from 2025. This episode originally appeared on the Off the Grid Clubhouse for paid subscribers, so we’re thrilled Amelia Hruby, PhD has shared this episode with us, so we could share it with you!

Go behind the scenes of two book launches: Amelia’s Your Attention is Sacred Except on Social Media and Jessica’s Leaving the Casino.

You’ll get two behind-the-scenes views into self-publishing, including super transparent numbers on our audience sizes and book sales. 👀 Amelia and Jessica had two different launch strategies (for two different types of books), so enjoy the contrasting approaches.

We also get into pricing strategies, long-term marketing, and the messy feelings that come up when you can see who exactly has bought your book (and who has not). 😵‍💫

* 📖 BUY JESSICA’S BOOK: deeperfoundations.com/casino (or on Amazon, where the Kindle and Paperback edition came early!)

* 📖 BUY AMELIA’S BOOK: offthegrid.fun/attention

* Join the Interweb: https://offthegrid.fun/interweb

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 spend time on the gray areas that don’t get talked about much: how to tell the difference between resistance and a real boundary, why not every hard thing is misalignment, and how we can navigate through uncomfortable stretches in our business. We get clear about scope of practice and why she didn’t turn somatics into a product.

There’s also some aggressively human moments for Meg and mini-coaching for Jessica about how her body showed up to help make a decision about postponing a launch.

* Helen’s evolution from copywriter to regenerative business designer

* What somatic experiencing actually means

* The difference between scope of practice, staying in our lane, and showing up as your whole self

* Why not every discomfort is misalignment—and not every “no” is avoidance

* How entrepreneurs confuse resistance, fear, and true boundaries

* Why scope of practice matters when working with trauma-adjacent material

* What it looks like to design a business that accounts for real bodies and real lives

* How values, identity, and lived experience shape copy and marketing

* Why “alignment” culture can quietly reproduce hustle and self-blame

* The role of witnessing, mirroring, and permission in business decisions

“You still need to to do lead gen, showing up and doing the thing. And, so if not LinkedIn, then what? So let’s say we find out that LinkedIn is not the good place for you. That’s okay. I may push it depending upon what your business is and who your people are and may push it and say, okay, let’s explore that.

But let’s also explore other alternatives that feel less “Ugh.” So if you have this idea that LinkedIn is the way to go, but LinkedIn is so hard and therefore you’re not doing any marketing, let’s get you into posting somewhere else.” - Helen

About our Guest

Helen Tremethick

Mentioned Episodes

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, the two of us talk honestly about something we see over and over again—in our clients, in our businesses, and sometimes in ourselves: the difference between having a strategy and having the support to actually do the work. We both love a good plan, but we’ve watched plenty of perfectly sound strategies fall apart the moment they hit a real calendar, a real workload, or a real human with limited energy.

Our conversation explores what strategy really gives you (direction, priorities, a sense of sequence) and what implementation requires (the skills to actually execute, time, and accountability). We compare strategy to a map: it shows where you want to go and the possible routes to get there. And we talk about the gap, when you need turn-by-turn directions, the recalculating voice when they get off track, and sometimes, the driver who can help get them moving again. The conversation ranges from client experiences with “strategy-only” offers to what it means to truly support implementation—through deadlines, accountability, and a bit of hands-on help when needed.

* Why “strategy-only” offers often fail to create results

* Jessica’s 28-point SEO plan story—and what it revealed about capacity vs. desire

* How clients need different kinds of support: the map, the GPS, or the person doing the work

* The “recalculating” role—why to choose a provider who will help you get back on course after a detour

* Why overwhelm happens when the plan outpaces your emotional or practical capacity

* Jessica’s existential “do I go hands on or not” dilemma

* How deadlines, feedback, and accountability turn theory into momentum

* Why AI can’t be your driver—it doesn’t check if you actually did the thing

* The truth: strategy doesn’t scale without implementation rhythms and time management

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 talk about what makes co-hosting work: shared accountability, complementary energy cycles, and overlapping but distinct guest networks. We talk about how the Aggressively Human podcast served our business goals that we set out for a year ago. We share the behind-the-scenes lessons of running a human-centered podcast—everything from scheduling and editing to scouting guests and showing up with curiosity and authenticity.

The conversation also explores how both of our businesses have evolved over the past year—Jessica closing out her first five-year arc with Leaving the Casino and Meg deepening her work in AIO, and how we’re thinking about AI, automations, and algorithms today in 2025.

* What makes a co-hosted podcast sustainable for a full year

* How mutual accountability keeps the rhythm (even when energy dips)

* The hidden work behind guest curation, editing, and show notes

* Why we feel more energized after an hour podcast than a 15 minute YouTube

* Why we avoid “pitch-me” guests and only invite people they know or admire

* What we’ve learned about informal promotion, reciprocity, and trust

* How podcasting has strengthened our friendship and creative shorthand

* What’s changed in both of our businesses since the show began

* How automation and AI can serve memory, not replace humanity

* What year two will explore: ethics, curiosity, and using the tools without being used by them

“Now that we know what the tools are, we’re seeing what’s starting to be possible, how are we looking at curious ways to bring it into our business models to use these tools, not at arm’s length, but to say, these have a place in the tool belt.” - 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

And while many podcasts are paused today, we wanted to bring some Aggressively Human to you while you’re cooking, carving, or just getting out of the house in between football games.

We want to say thank you to our listeners. Thank you to anyone that has rated the podcast on your preferred podcast player!

Thank you to our commenters, the ones who tell us what they loved or have questions about in the episodes.

Thank you to our guests, who make time to come hang with us and showcase what’s aggressively human in your lives and businesses.

And, from Jessica and Meg to each other, hear us say thank you to our co-host.

It’s so much more fun with friends.

Plus, hear a fun fact about when each of us met our husbands!

Ok - now go back and finish eating pie, if that’s on the to-do list for today.

(P.S. - my favorite is pecan, I am from the mid-atlantic. Meg’s favorite is pumpkin).

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, Jessica and Meg are joined by Nick Bennett and Erica Schneider, the duo behind Duo Consulting, for a conversation about business models, burnout, and what’s really behind scale. They trace their journey from the course boom and “productized” advice back toward deeply human, high-touch service work—and the freedom that came with doing less, but better.

They talk about what happens when you stop selling one-time solutions and solve recurring problems, how to rethink retainers, and why “selling like a human” is still the most powerful business strategy. The group also digs into the false hierarchy between consulting, coaching, and implementation—and how being hands-on can actually create more impact, more fulfillment, and better outcomes for clients.

Tired of the “retainers” vs. “courses” vs. “productized services” debates on LinkedIn about the best business model? Learn how we’re all building the kind of business that fits our energy, our brains, and our lives.

* Nick and Erica’s evolution from solo operators to partners at Duo Consulting

* Why they retired their successful course and community in favor of 1:1 work

* Why most “passive income” models still require constant marketing

* How to match recurring problems with recurring offers

* The debate between retainers, projects, and sprints—and why none are one-size-fits-all

* How to sell like a human instead of hiding behind funnels and scripts

* Why client success—not volume—is the real measure of scale

* The false hierarchy between coaching, consulting, and done-for-you work

* How standardization, automation, and selective delegation create sustainable growth

The reason we’re so passionate about helping our clients move to solving an ongoing problem is that in that retainer model you get to drag your clients to glory. Because then you can say, “look at all of this awesome success that my clients have working with me”. I would rather my clients work with five people a year and have those five people be massively successful than work with 50 people a year and have no clue or help them achieve nothing.” - Nick Bennett

About our Guests

Duo Consulting

Nick Bennett

Erica Schneider

How Solos Scale

The Recognition Gap

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

They share the practical and philosophical reasons behind the shift: protecting your intellectual property, proving you got there first, and creating a timestamped body of work that can be found, cited, and built upon. It’s how you build a business on rock instead of the sand of social media and shifting algorithms.

From domain authority and discoverability to Substack cross-posting and AI parsing, they look at what it means to write for durability, not trends. They also explore how written assets double as onboarding tools, teaching material, and long-lasting content that can be reused across your ecosystem—bricks in a foundation that lasts.

(Plus, hear Meg sing a song that totally relates!).

* Why Meg is returning to blogging after three years focused on other platforms

* The “sandy land” metaphor and what it means to build your house on a rock

* How blogging establishes topical authority and protects your IP

* Why timestamps matter: AI can’t cite a TikTok, but it can cite a post with a publication date

* The danger of building on rented land (Substack, LinkedIn, social media)

* How written work creates a paper trail for your thought leadership

* Blogging as both visibility strategy and proof of ownership

* How AI and search engines reward structured, linked, human-written content

* Turning blog posts into reusable assets for onboarding and education

* Why a durable body of work outlasts any short-form content trend

“If you build your house on sand, you’ll have to build it twice.” - Meg

Resources

Love at First Search Blog

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

Book released October 2025

Jessica walks through what that cycle looks like for LinkedIn and Substack, while Meg connects it to the decay of creative platforms like Medium and Kindle publishing. Together, they explore what creators and experts can do when every channel feels rigged—and what it means to build on digital “rented land.”

It’s part diagnosis, part “what now”: a conversation about recognizing when the rules have changed, when to adjust your strategy, and how to build resilient foundations that outlast the next platform crash.

* The origin of the term “enshittification” and how Cory Doctorow describes the four-stage cycle

* What Facebook, LinkedIn, Twitter, and Substack teach us about platform decay

* How AI tools are repeating the same subsidized-growth pattern as social media

* The false nostalgia for “when it worked” and how fast cycles now move

* What to do when the strategy you learned in phase one stops working in phase three

* How to spot market arbitrage opportunities before they close

* Why foundations, relationships, and your body of work are the only real insurance

* How to keep your business discoverable without chasing every new trend

Additional Resources

Podcast | The Gray Area

Why is the Internet bad now? | Evan Armstrong/The Leverage

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

She shares how she built her “AI team”—including Remy, the snarky Gen Z assistant who filters her inbox and protects her calendar—and why she treats her chatbots like departments inside her business. They talk about how AI can help reduce emotional labor, from grocery budgets to health tracking, and what it means to build systems that keep the human at the center.

This conversation is filled with practical ways to make AI feel less robotic (and maybe a little more like a helpful intern who swears), while lightening your load with technology that actually serves you.

* Mary’s path from librarian and tarot reader to tech director and business coach

* How she organizes AI “staff” into departments—finance, operations, marketing, and more

* The surprising power of giving your bots names and personalities

* Why AI reveals more about your delegation habits than you think

* How to build an AI “board of advisors” with personas like Mark Cuban or Reese Witherspoon

* Emotional patterns people bring to technology (and what that says about leadership)

* Creative personal uses for AI—from meal-planning and purchasing decisions to health tracking

“I would argue if you had an intern, if you had a Gen Z Remy with you, you’d still fact check them because they’re young, they’re learning. I need to make sure that everything’s right. And in that sense, you’re still doing the same functions, you’re not doing less, you’re really not doing more. It’s just moving along faster.” - Mary

About our Guest

Mary Williams: Sensible Woo | Sasquatch Media Grounds

You, Me ChatGPT Workshop

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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, Meg interviews Jessica about her new book, Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works. The conversation traces how the book came to life—from frustration with hollow business advice to the creation of a grounded, systems-based framework for experts who want to stay small, sustainable, and sovereign.

Jessica shares how she read her way through the entire business section—books that were motivational but hollow, all premise and no practice. Some were thinly veiled sales funnels; others were memoirs pretending to be manuals. None answered the questions solo business owners actually ask: How do I make better decisions? What kind of business am I running? What’s enough? And how do I make this sustainable?

They explore what’s missing from most business books, the trap of “CEO-energy” culture, and the myth that scaling is the only path forward. Jessica shares how years of client work, research, and teaching evolved into a practical field guide for soloists who want to build differently—without gambling their time or integrity.

Get the details behind Leaving the Casino!

* Why Jessica wrote Leaving the Casino after realizing most advice ignores context

* How the online business world sells tactics that don’t fit most experts

* Why many books are either memoirs or funnels to a paid program

* How Jessica went from consulting to creating and publishing the book

* The limits of frameworks like Profit First, Traction, and Essentialism

* The risks of outsourcing sales, marketing, and finance too early

* Responsibility, enoughness, and right-sized growth as operating principles

* How privilege and life circumstances affect what “success” looks like

* Why the book blends manifesto and textbook—both call-to-arms and manual

* Jessica’s hope that it becomes a long-term reference for expert entrepreneurs

Resources

Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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, Shivani Mehta Bhatia joins Aggressively Human to talk about the changing nature of conflict—especially in a world shaped by grief, uncertainty, and fraying trust.

We explore how conflict has shifted post-2020, how our nervous systems are adapting (or not), and why repair feels harder than ever. We talk about Shivani’s approach of “conflict midwifery,” destructive versus generative conflict, and what it means to build and lead with more care in increasingly reactive times.

Whether you’re navigating tension in your team, your audience, or your closest relationships, this conversation offers a more humane way through.

* What conflict looks like now—and why it feels more brittle

* The 5 parts of Shivani’s “prism of conflict”

* What “conflict midwifery” means and how it changes the repair process

* What ChatGPT says are the fixes of our current polycrisis

* What it takes to repair when there’s no shared script

* What’s the smallest possible actions we can take in conflict

* Leading and relating in a time of collective dysregulation

* How we can prepare—not avoid—hard conversations

About our Guest

Shivani Mehta Bhatia

Monthly Conflict Clinic

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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, Megan Dowd joins Aggressively Human to talk about what it actually looks like to build a business that respects your creative cycles—and what happens when you don’t. From the pressure to always be visible to the collapse that can follow, we explore what it’s like to build a business while also being a human with a nervous system.

We talk about the performance trap of “consistent content,” what to do when you’re no longer interested in your own work, and when and how to use data and systems to support you.

This is a conversation about honoring your capacity without disappearing, how to say no to content you resent, and why creative rest is not a threat to your business—but often the reason you stay in it at all.

* What it really means to have a “human-first” business (hint: it’s not about the right font)

* The burnout that comes from forcing content for the algorithm

* Navigating visibility after a performance hangover

* When to blow up your content calendar for the thing you’re excited about — and when not to

* Choosing the work that feels good, even when it doesn’t scale

* The myth of “consistency” and what your audience actually needs from you

* The identity whiplash of letting go of “known” offers to create something new

* How Megan is reshaping what success looks like in her next chapter

About our Guest

Megan Dowd

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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, Meg takes us inside the creation and launch of Findable Everywhere—not as a polished “launch debrief,” but as a real-time reflection on what it means to declare a new chapter in your work. We dig into the decisions along the way: how a paused summit talk became a test run, how she built a course that worked for beginners and advanced folks (and the complications that come with that), and how teaching this material sharpened her clarity and authority. Plus: the real numbers, the behind-the-scenes updates, and the emotional roller coaster of launching while also changing.

But even more, Jessica and Meg get into the behind-the-scenes decisions, pivots, and identity upgrades that can only come from publicly claiming your voice—even if you’re still figuring out what it sounds like now.

* Why this angle simmered for over a year before it became an offer

* How a “focus group” (aka an old summit talk) helped clarify the direction

* What shifted in Meg’s identity and voice as shifted from AI as separate to AI as integral to client results

* Why Meg built Findable Everywhere for both beginners and seasoned marketers—and what that complicated

* The emotional roller coaster of launching something that feels deeply personal

* The real numbers, real process, and real moments of “do I even want to do this?”

* Why launches aren’t just marketing events—they’re identity markers

* How teaching the material shaped Meg’s own authority

* The difference between planning a pivot and living one in real time

Want to get access to the challenge and a YEAR of implementation support?

Join the Content Love Lab and be on your way to be Findable Everywhere.

Live Trainings begin October 7, and you can get twice a month check-in on your content!

Join the Content Love Lab

Content Love Lab

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

But how are business owners using AI in creative ways that honor the voice of our businesses while being more effective?

Enter Prerna Malik and Content Bistro. Prerna caught our eye with the Skeptic Buyer Bot—a tool that actually helps creators pressure-test their sales pages and offers through an AI-powered lens. (Yes, Jessica used it. Yes, she has thoughts.)

We dig into how Prerna is using AI to amplify human work, not replace it. How her agency turns real voice-of-customer data into conversion gold. And why the best sales copy isn’t about cleverness—it’s about clarity, empathy, and making decisions easier for your buyer.

* What makes a good AI tool (hint: it’s not a clone of you)

* How Prerna uses the frameworks behind the Skeptic Buyer Bot to improve sales pages (because not every buyer is the same)

* Why real customer data is your best copy asset

* What makes a good voice-of-customer process (and what doesn’t)

* Why AI should make your thinking better—not do it for you

* When to not listen to best practices and trust your voice instead

* Why thoughtful critique is one of the most valuable services you can sell

“You need to remember, you are the superior brain. You need to look at the facts. You need to check everything. You just cannot ever take what. LLM chat, Claude or anyone else is giving you as the truth.” - Prerna

About our Guest

Content Bistro

Skeptic Buyer Bot

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 Part 2 of our conversation with Erika Tebbens, we go deeper—into the murky middle of business ethics, entrepreneurship under capitalism, and how we’re operating in the political climate of 2025.

We talk about the ethics of selling transformation, why systems don’t always equal support, and what Erika has learned about nervous system safety outside the online business bubble. This episode is full of those “I’ve been thinking this but no one’s saying it” moments, plus a little bit of righteous rage and some gentle reminders that you’re allowed to do things differently.

Whether you’re reimagining your business, your systems, or your relationship to capitalism itself, this episode will give you plenty to think about—and maybe even a little relief.

In this episode:

* What happens to your identity after entrepreneurship

* How to design systems that support your actual nervous system (not just your productivity)

* The uncomfortable truth about selling transformation online

* Why the ethics of business can’t be separated from capitalism

* What real resourcing looks like—beyond time freedom or self-employment

* Why Erika feels more supported working in an organization than she did solo

About our Guest

Erika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-Making

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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, Erika Tebbens joins us to talk about her career pivot out of entrepreneurship and into employment. After years of running a successful, values-driven consulting business, Erika realized that being her own boss no longer served her well. So she made a bold move: she got a job, at a dream company, in a field she deeply cares about. And how Erika’s move back into farming and farm systems so perfectly aligns with the Aggressively Human ethos.

This isn’t your typical “how to change careers” episode. We talk about the real emotional rollercoaster of identity shifts, why online business doesn’t always deliver on its promises, and how to reimagine freedom when you're no longer selling yourself online.

In this episode:

* Why Erika walked away from her consulting business (even though it was “working”)

* The grief and relief of leaving behind entrepreneurship

* How she landed a job she loves in this economy (and it’s not about hundreds of applications to the LinkedIn black hole)

* What it’s like to re-enter the workforce after 20 years of being the boss (and the feeling of only having one job, instead of having 15 jobs as a solopreneur doing it all)

* How to tell the difference between real freedom and the illusion of control

About our Guest

Erika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-Making

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 with psychologist and leadership coach Dr. Matthew Jones to talk about the often-overlooked emotional labor of working in partnership. We explore the dynamics that make co-founding relationships thrive (or fail), and what it looks like to prioritize care, communication, and clarity in a space that’s often full of pressure, ambition, and high stakes.

We also talk about how to navigate conflict before it turns into resentment, how to separate identity from performance, and why leading with someone else requires emotional maturity—not just shared goals.

Whether you’re co-leading a business, collaborating on a big project, or just trying to make it work with a fellow human in your orbit, this episode is a reminder: the relationship is the container.

* Why your co-founder relationship is the most important “system” in your business

* How to name the power dynamics that exist—and move through them with care

* The three languages present in co-founder communication - and why overindexing on “goals” might be counterproductive

* Building routines that strengthen the relationship, not just the company (think “date nights”, but for co-founders)

* How we can (and can’t) use AI to help us communicate with our co-founder

* Why emotional fluency is core to shared leadership

* Matt’s journey of self-publishing

About our Guest

Dr. Matthew Jones

The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup Success

Mentioned Resources

John and Julie Gottman

Imago Therapy

Noam Wasserman’s The Founder’s Dilemma

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

* Why Jessica is running Meta ads and why she feels she’s doing it wrong

* How Meg has leaned into retainer work this summer and it’s been exactly what she needed

* The soothing activities of repeatable, even some kind of boring work

* Confronting business model realities (“it can be easy to sell or easy to deliver but it cannot be both”)

* Meg’s fall challenge: Findable Everywhere (because even though how we search might be changing, the fundamentals of showing up in AI and SEO are even more critical).

* Jessica’s summer program debrief, and how it went from 9 prompts to 6 videos, 30+ prompts, and 10 detailed resources.

* Jessica’s fall, including the Define Your Foundations business building cohort and the book launch.

Join us this Fall:

* Findable Everywhere: A 5-Day Challenge to Show Up on Google, ChatGPT, And Wherever Your Dream Clients are Searching

* Define Your Foundations: Escape the “Tactics Trap” and start building real business foundations.

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 always see the polished outcome of change.

The business owner who goes on sabbatical… to emerge with newly-refined offers and a perfect website.

The offer idea that emerged in the shower… and is immediately birthed into a pristine sales page (with seemingly no revisions needed!).

But what happens in the middle? And why does so much of the work happen after the first draft of any change in the editing and remixing process?

We talk with Samantha K Pollack from Indie Copy Studio about what it means to remix your business through her journey from a launch copywriter behind-the-scenes of big brands to her new business model. We talk about the slow, murky, and very real process of business change: how shifts actually unfold, how you know something’s no longer aligned, and how hard it can be to hold the tension while you figure out what’s next.

And we talk about editing: the power of an editor, why learning the craft of editing and writing is so important, when you need a copywriter (and when you don’t), and why editing is for your business, not just your writing.

* The honest, behind-the-scenes look at a business in transition

* The specific kind of stuckness that shows up when you're evolving

* Why actually doing the work you want to do comes before the website, not afterwards

* How Sam approaches editing as a craft, and why it matters

* Why you need to learn your own rhythms to avoid sounding like generic AI (and why editing is safe from this generation of generative AI)

* Why learning to edit your own copy helps you make better business decisions

* The awkward truth that your website will never fully keep up

“And when you look at someone else's writing and you're like, ‘this really spoke to me, like I really loved this little line right here. And then here's a place where I felt like I didn't really understand what you were talking about anymore.’ You're developing your own critical eye for writing and then you can apply that to your own writing.” - Samantha

About our Guest

Samantha Pollack - and join the “Get the Mixtape” newsletter

The Craft small group writing workshop

Substack: https://substack.com/@indiecopystudio

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 sit down with The Entrepreneurs’s Therapist Shulamit Ber Levtov to talk about the nervous system realities of entrepreneurship—especially for those who didn’t become entrepreneurs by opportunity but by necessity.

We talk about what it means to choose our nervous system activities, how to understand what’s in (and out of) our control, and the unique paradox of entrepreneurship: you get freedom… and also you’re the one holding the whole thing together.

As Shula says, “Entrepreneurship and mental health are inseparable. We write business plans, marketing plans, financial forecasts, but where’s the mental health plan?”

Whether you’re burned out or just bracing for what’s next, this episode offers frameworks and honest permission to put real nervous system management at the center of your business.

* Why your nervous system is a business asset

* How to distinguish between societal pressures, industry pressures, and our own decisions impacting our nervous systems

* The paradox of entrepreneurship: control and uncertainty at the same time

* Why some of us didn’t “choose” entrepreneurship—and why that matters

* The role of locus of control and how it helps you manage business stress

* When to phone a friend versus make a business decision in the moment

* How to build a personalized nervous system toolkit (without another productivity checklist)

“And then there's the very basic individual nervous system reaction to response running your own business. Business success equals survival. Intellectually, I'm not gonna starve and die if my business fails. I mean, it's gonna be stressful, it's gonna be hard. I may have very heightened circumstances. I may lose my house. A lot of really bad sh*t can happen, but it's survivable stuff if your business fails. But this is intellectual knowledge, not nervous system level stuff.” - Shulamit

About our Guest

Shulamit Ber Levtov

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 role does content play in our businesses? And how does that shift over time?

We may not have consciously chosen this as a duo, but Meg and Jessica are moving in two different directions in their business.

Jessica, being just 5 years in, is moving from less content (and a few longer-term, higher-touch clients) to even more content and leveraged offers, and Meg, farther along on her business timeline, is moving in the opposite direction.

But in both of our businesses, content (and the act of creating content) is still very important in our businesses, but in different ways. From content as teaching assets, to being found in AI, to helping us define our signature linguistic styles, we explore how we create content, why we create content, and how we use it throughout the entire customer journey. Hear why Meg produces detailed content for her community, why Jessica’s McKinsey training has made her slide presentations wildly too dense, and what we’re working on doing with our content during an AI-slop onslaught.

* How our businesses have shifted since we started the podcast

* The stages of building a foundational body of work

* How the role content shifts when your business moves from broadcast and higher-volume to inbound and lower-volume

* How can you be found in AI searches (and why the principles of SEO and good content matters even more now)

* Proactive versus reactive content development, and the power of content that’s not meant for wide distribution

* Why creating intellectual property is different than feeding an algorithm

* What going more broad with your content does to your nervous system

* How we think about lead magnets, content libraries, and reusing what still works

* The questions we’re asking before we create anything new

“But I think also creating content is a way to develop your signature phrases, the things that you're known for, the words that you use on the regular, what your client's parrot back to you and every time I've asked AI it comes up with snappy phrases, but it doesn't come up with my phrases.

But I think the only way I can come up with my phrases and my shapes and my symbols and things like that is by creating the content myself.” - Jessica

Resources Mentioned:

Diann Wingert: https://www.diannwingertcoaching.com/adhd-ish-podcast

Ryan Trahan’s 50 states in 50 days video: https://youtu.be/KTYbvU-aSf4?si=fCaJ3rZogru3hifU

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

But what if meetings, and workplace culture generally, didn’t have to be awful? What if we could bring energy and collaboration, like the kind we get from a well-facilitated workshop, into our day-to-day culture?

In this episode, Alison Coward joins Aggressively Human to show what it really means to lead through a facilitative and collaborative lens—not just to make meetings more efficient, but to make collaboration more human. We explore the difference between participation and true engagement, and why a good facilitator doesn’t just run the meeting—they make space for decisions, disagreement, and trust.

And we also confront the realities of AI in the workplace. Because AI can craft the agenda and synthesize the notes… but can it feel the charge of conversation? And what do we lose when we outsource the hard conversations to software that avoids conflict and resilience building?

* What “workshop culture” really means—and why it’s not just for facilitators

* Why great collaboration isn’t about airtime, it’s about alignment

* How to lead across generations when work expectations aren’t the same

* The role of facilitation in navigating polarized teams and hard topics

* Why AI can’t replace the discomfort, nuance, and trust-building of real conversation

* The hidden labor of designing meetings that actually lead to decisions

* Why clarity isn’t always the goal—sometimes it’s about making space for complexity

* How to tell when your team needs a better process (not another tool)

“When we default to using those tools, we're robbing ourselves of the chance to build those very human skills that enable us to relate to each other more effectively. Conversations are difficult. They're meant to be, that's why they're called difficult conversations. And sometimes the process of going through that difficult conversation hones and smooths the edges off. It's almost like a process that we go through that doesn't feel uncomfortable when we get to the other side. We've learned something new and perhaps we've built a connection with someone else. And the thing is, is that those kinds of difficult conversations or those situations are the very thing that people are like, oh, AI can do that for me now because they wanna avoid that uncomfortable feeling.”

About our Guest

Alison Coward and Newsletter

LinkedIn

Workshop Culture: buy directly from www.practicalinspiration.com or indiepubs for US customers and use code WRKCULT30 for 30% discount

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

So today’s episode is both a debrief on going to conferences and also a recap of the 4 takeaways from Craft and Commerce that are informing our year ahead.

We dig into conferences:

* Why putting yourself in the position to meet people can help you meet your internet heroes… and can also help you sell more things. (Shoutout to former guest Jeremy Enns here).

* How does one maintain relationships with people so that the next years of the conference just get better and better?

* Why presentation-heavy conferences miss the point, especially for more seasoned attendees (and how to think about the composition of the audience).

And then, we dig into the four takeaways from the conference itself.

* We’re entering into an AI content doom loop.

* What’s your “use and refuse” AI strategy?.

* Storytelling reigns supreme.

* There is no “overnight success”.

“If they don't exist, they will in the next six months is a tool that if you list a number of the influencers you wanna follow and comment on their post… and so you just feed it into an AI tool and that AI tool will come up with an AI generated comment. So you don't even have to log into LinkedIn. If this doesn't exist, I guarantee it will in like the next six months. You wouldn't even have to log in to see what your favorite influencer posted and the AI comments on their stuff so that your stuff feeds goes into the feed.

And, some AI tool is gonna go into your library of content that you've created already, and it's gonna snip out something, drop it on LinkedIn, some other bot is gonna comment on it, and then there's no human involved in some of that stuff, period.” - Jessica

Mentioned Resources

Pamela Slim

Jeremy Enns’s Content Strategy Schematic

Neurodiversion Conference

She’s so Lucky with Les Alfred

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

Emma Whittard (mindset coach) and Karen Worthy (executive career transition coach) had their “business meet cute” in one of Jessica’s classes. What started as simple client referrals turned into collaborations, a shared offer, and even Emma supporting Karen’s business behind the scenes. From the first casual chat to co-creating paid offers, sharing clients, and navigating logistics (like money, time zones, and email volume), we talk about how they built trust without a contract, how they make decisions, and what it means to do good work together.

We talk about the emotional labor of collaboration, the unspoken agreements, and what it takes to prioritize relationship over revenue in a world that teaches us to keep everything transactional.

Before teaming up with someone, listen to the foundation of what makes this collaboration work.

* How a casual class connection became a long-term collaboration

* Why their “Base Camp” offer came after the referrals, not before

* What they’ve learned about setting boundaries, expectations, and pricing

* The value of emotional support, operational partnership, and sounding boards

* Navigating logistics: scheduling, tech, shared values—and the messy middle

* Why trust (not contracts) is what makes these kinds of partnerships work

“We also both said upfront that our relationship was more important than the business together. So the relationship first. That means that hopefully we won't get into a situation where there's something icky happening and we can't address it, or it sort of ruins things. So again, it is back to values and priorities again.” - Emma Whittard

About our Guests

Emma Whittard | LinkedIn

Karen Worthy | LinkedIn

Base Camp Offer

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 cover how to adapt to a maturing market, where the “growth hacks” of the past aren’t working like they used to. Michelle shares why most client issues aren’t massive strategy problems but small, foundational misalignments—and why fixing them starts with a return to the basics.

This is an episode for anyone feeling like what used to work just… doesn’t anymore. And for those ready to stop chasing the next big trick and return to the very unsexy, very effective roots of sustainable business.

* Why the market isn’t broken—it’s just finally maturing (and your tactics need to, too)

* The real reason your sales aren’t working (hint: it’s not because you’re not posting enough)

* The problem with marketing arbitrage plays (Substack, LinkedIn newsletters, bundles—you name it)

* Why your offer math might be the real problem behind your revenue plateau

* How AI is making everyone sound the same—and how to stand out by being specific

* Why the boring fundamentals are the most effective thing you can do right now

* What to do instead of panic-posting when leads slow down

“That's the key to relationships. The specificity and the “because statements” allow you to also build sticky relationships. So a lot of times when we're networking a, we don't know why we're networking with people, so we end up just meeting people and then trying to force square pegs into round holes, and b. so then you get stuck in these small talk traps.” - Michelle Warner

About our Guest

Michelle Warner

Sequence over Strategy podcast

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

First, Jessica shares how running free monthly workshops—starting with just four people—has become one of the most grounding, trust-building practices in her business. Not because they’re optimized for conversion, but because they create real-time space to test ideas, teach generously, and build actual relationships.

Then, Meg takes the mic to talk about the surprising overlap between SEO strategy and romance novels. Drawing from her writing practice and deep love of story, she maps the early stages of the hero’s journey onto the buyer journey—and shows how thoughtful content meets people where they are, not where your funnel wants them to be.

Let us know: do you like some shorter, solo episodes in your feed?

We’ll be back next week with more dialogue!

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

By leading through an intersectional, feminist, and collective lens.

In this episode, we talk with Becky Mollenkamp about what it means to build and lead this way: grounded in shared power, mutual care, and collective growth. Becky shares how her work as a coach and podcaster has evolved over the years, why she’s no longer trying to “go it alone,” and how building in community has been the most liberating move of all. We also talk about what it really means to earn money ethically, challenge systems without burning out, and keep showing up (even in the chaos of summer).

We also get into the behind-the-scenes of launching multiple podcasts, navigating Substack and social media with ethics intact, and the real tension of building a business when you care deeply about people and want to pay your bills without selling your soul.

This is a conversation for anyone trying to build something different in a world that rewards “the one right way to build.”

* How Becky’s proximity to the Ferguson uprising catalyzed a shift in her perspective

* The real difference between commerce and capitalism (and why most pricing models get this wrong)

* What it means to build a business rooted in mutuality, not hierarchy

* What the hell to do with Substack, Meta, and other imperfect tools

* The behind-the-scenes of stewarding multiple podcasts, and the choice to have a co-host or not

* The problem with trying to do it all alone—and how Becky’s moving toward collective action over solo growth

* Why podcasting might just be the most human way to have the conversations we actually want to have

“Yeah, I can come up with lots of ideas, but they're always richer when it's done in collective with these other women who have different lived experiences than me. And then, yeah, I'll move the ball forward. I love moving the ball forward, but I'm more excited now. I'm moving the ball forward with these ideas that are so much more richer.” - Becky

About our Guest

Becky Mollenkamp

Feminist Podcasters Collective

Feminist Founders

Messy Liberation

Assigned Reading

Mentioned Resources

Tema Okun’s Essay

Sacred Economics by Charles Eisenstein

The Soul of Money by Lynne Twist

“The Master’s Tools Will Never Dismantle the Master’s House” — Audre Lorde

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 sit down with Diann Wingert—former therapist, business coach, and host of the ADHD-ish podcast—to talk about what it really means to build a business that works with your brain, not against it.

We unpack the myths around ADHD, how to radically accept your own wiring, and what happens when you finally stop trying to “fix” yourself and start designing systems that fit you.

Jessica and Meg share their own neurodiverse workarounds (including why their assistants actually manage them), and Diann breaks down how she flipped her brand, rethought her support systems, and uses tools like Claude.ai as external executive function—not a replacement for her brain, but a co-pilot for organizing all the genius.

This one’s for the quirky kids, the not-quite-diagnosed, and anyone who’s ever tried to follow business advice that wasn't designed for their brain.

* Why Diann rebranded her podcast and business to center ADHD-ish, not as a niche but as a reality

* How radical self-acceptance (not self-awareness) is the real first step to change

* The business systems that work because they’re nontraditional (like letting your assistant be the boss)

* Why “It depends” is the real ADHD business motto

* How tools like Claude and Notion help organize brilliance without replacing your voice

* Why standard business advice falls apart when your brain doesn't fit the mold

* What Diann learned from neurodivergent-friendly spaces (hello, marching band at a conference) and how to bring that into your own business model

* The role of AI in organizing, not empathizing—and why therapy still needs a human touch

“Human beings, by and large, are damaged through relationships, abuse, neglect, trauma. Most of the things that bring people to a therapist happened as a result of some failure of human nature. And so the whole transformation of therapy is that it is using the professional use of self. We are harmed by humans. We are healed by humans. It’s one of the most intimate and powerful ways of working. And I loved it.” - Diann

About Our Guest

ADHD-ish Podcast

Mastering Your Entrepreneurial ADHD

Diann Wingert’s LinkedIn Newsletter

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 dive into Maggie’s journey from agency owner to solo business advocate, the messy parts of writing (and marketing) a book without turning it into a performative launch, and the very real tension between wanting to build a sustainable business—while feeling pressure to do it in a way that exploits your time or other people’s labor. (Thanks, online business influencers).

We also talk about typos in print books, sticker packs as marketing tools, and why self-publishing may outperform traditional publishing as a soloist. Whether you’re a solopreneur, a micro-agency owner, or just someone wondering if you have to scale to be legit, Maggie’s perspective offers a breath of fresh air—and a permission slip to do it your way.

* Why Staying Solo matters—especially when the default advice is always to “scale”

* The tension between running an agency and telling others not to build one

* How Maggie’s book journey came out of years of blog posts and a poolside conversation

* The ethics of pricing, paying others well, and not replicating exploitative business practices

* The weird relief (and panic) of finding typos in a printed book you can’t easily fix

* How to stay human while promoting a book (sticker packs, handwritten notes, book tours)

* Book marketing vs. book selling—why Maggie chose self-publishing and what surprised her most

* The privilege of staying solo—and how to be clear about who you want to serve

* Most importantly, the 5 book names for Maggie’s book themed birdhouse.

About our Guest

Maggie Patterson

Staying Solo

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 talk about how building relationships is about more than just dropping into people’s inboxes—and how Relationship Rhythms is designed to bring playfulness (and prizes!) back into the process. Jessica shares why she’s finally running an asynchronous offer and how Relationship Rhythms is different from her usual programs, plus what happens when you go from dreaming to launching.

We also get real about our own partnership: the messy business of joint ventures, what happens when your business is in a different gear than your friend’s, and how to talk about money and collaboration in a way that feels human.

And because she couldn’t resist, Meg quizzes Jessica on AI trivia—highlighting the joys, the contradictions, and the occasional panic about what AI knows, what it doesn’t, and how we’re using (and refusing) it in our own businesses.

If you’ve ever felt like your business friendships are an ever-evolving dance—or wondered how to balance AI curiosity with human connections—listen in. 🍊

PS. If you made it to the end of this episode, drop our Easter Egg word on Substack as a comment to let us know you’re here for the rambles, not just the frameworks.

* Jessica’s summer program, Relationship Rhythms, and how it’s ushering in a more experimental vibe.

* How Relationship Rhythms uses gamified accountability (yes, with prizes) to make relationship building fun

* Why Jessica and Meg decided not to monetize the Substack—yet—and the honest convo about splitting podcast revenue

* The challenges of co-hosting a podcast when your businesses are in different seasons (and speeds)

* The messy beauty of relationship building: why some outreach grows instantly while others marinate for months

* Meg’s AI trivia quiz: from radiologists to Reddit, from ChatGPT’s energy usage to recipes with random ground beef

* Why learning how to learn will still be a critical skill, no matter about AI’s capabilities

Bloom’s Taxonomy

Join Relationship Rhythms

Sign up for the waitlist or join the program (opens June 9).

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

Have you ever struggled to consider yourself “interesting” when you haven’t gone to space or climbed a mountain?

Most importantly, how can you tell a story that AI cannot replace?

Story coach and speaker whisperer Mike Ganino joins us to talk about how to actually connect with other humans through storytelling, public speaking, and intentional presence. We talk about what’s missing when AI writes your copy, how to make your keynote more than just a case study, and why the most aggressively human thing you can do is show up—with your voice, your weirdness, and your body and breath. We talk about what job AI can’t do, why “tell your story” is often the worst advice, and how the most impactful stories usually come from Tuesdays, not TED Talks.

* How to pull stories from your actual life (even if they happened on a random Tuesday)

* What ChatGPT can and can’t do—and why public speaking is still a human-only activity

* Breaking free from the drip of consumption and embracing the interiority within us and around us.

* How to find your “inner interesting”, and how to transform extraordinary tales into relatable, personable stories.

* Why “tell your story” is terrible advice—and what to do instead

* How book marketing breaks your nervous system and what our favorite GIFs reveal about us

About our Guest:

Mike Ganino

Make A Scene: Storytelling, Stage Presence, and The Art of Being Unforgettable in Every Spotlight

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

Or is it actually that scheduling with busy calendars is hard. Prioritization is hard. Saying no to things so that you can say yes to the things you actually want to say yes to is hard. Those things are hard. But those things aren't friendship and those things are a part of every other part of life as well.” - Kat

Friendship doesn’t happen by accident in adulthood. And despite what the internet says, it’s not just about “finding your people.” You have to actually do something—and that can feel impossibly hard when your calendar is full and your energy’s shot.

In this episode, Jessica and Meg talk with Kat Vellos—UX designer turned friendship expert—about how adult friendships form, why they fizzle, and what gets in the way. We talk about courage (yes, it still matters), frequency, and how friendship isn’t a productivity project—it’s a relationship. We also touch on the uncomfortable truth: as AI creeps further into our inboxes and interactions, it’s easier than ever to think we’re connected—without actually having any real closeness at all.

If you’ve ever said, “I want more friends, but…”—this one’s for you.

* Why building adult friendship isn’t harder—it just requires different skills

* The four foundations of real friendship: compatibility, proximity, frequency, and commitment

* What’s actually hard about making friends (spoiler: it’s courage, not conversation)

* The social cost of optimizing everything—including how we spend time with people

* Why “being too busy” is often a boundary issue in disguise

* How Jessica tries to find local friends who want to talk about cold outreach (and the real dilemma of niche interests + neighborhood proximity)

* The difference between a friendship activity and a productivity checklist

* How to start small, go first, and create connection without waiting for an invite

About our Guest

Kat Vellos is the go-to source for guidance about cultivating meaningful friendships and community. She’s author of the book, We Should Get Together: The Secret to Cultivating Better Friendships. Kat’s writing is read in over 100 countries, and she’s been interviewed by The New York Times, NPR, and many more.

What if friendship is easier than you think?

The Togetherness Thing

Make yourself a Friendship Joy Train

How to find real friendships online via the algorithm

Product: BFF Builder Bundle

Course: Unbusy Camp

Course: Platonic Action Lab

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

But the quickest way to make a sale though is to get to that sales conversation as soon as you can and to make sure that it's as qualified as possible."

Most of us have been on the receiving end of a terrible cold pitch. Maybe it was a LinkedIn DM pretending to be friendly. Maybe it was an email that made you feel like a number. No surprise—cold outreach has earned its bad reputation.

But the truth is: cold outreach isn’t inherently bad. It’s just rarely done well.

In this episode of Aggressively Human, we’re joined by sales strategist Jessica Lorimer, who got her start in the kind of sales that makes people sweat: actual phone calls, to actual humans, in actual corporate offices. We talk about what it looks like to sell in a way that’s clear, kind, and effective—without relying on funnels, fake rapport, or endless social media content. She breaks down what still works, what definitely doesn’t, and how to sell in a way that’s honest, respectful, and doesn’t make you feel like a spammer.

This episode is part strategy, part sales therapy, and part reminder that you’re allowed to enjoy sales.

* Jessica’s origin story: how she sold her way into a boardroom (without a formal invite)

* How “being good at sales” actually made Jess feel in the early days of running an online business, and why she shifted from B2C to B2B sales

* Why Jess and Meg have both gotten rid of their funnels

* The five-step B2B sales framework Jess uses with her corporate clients (and why it works for soloists too)

* Why “I sent 10 emails and no one replied” isn’t a valid reason to give up

* What you actually need in a cold message (spoiler: not a fake compliment or a pitch)

* Why it’s not about “convincing” someone to buy—it’s about showing them it’s worth a conversation

* And why selling isn’t about tricking anyone—it’s about being clear, useful, and brave enough to go first

About our Guest

Jess Lorimer | LinkedIn

Selling to Corporate Podcast - a bi-weekly favorite of Jessica Lackey’s!

From Cold to Closed - open through May 18!

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

Hear us riff on the power of play and personality in our lives and businesses. We explore our different expressions of play as children and how it impacts our businesses today (hint: Meg was a dancer and playwright and Jessica loved to tinker with her Erector sets and handwoven crafts. Totally on brand for both of us). We talk we both experiment in our businesses (once we have the foundations in place), including our plans for the summer. We look at play as a regenerative act: one that requires energy and action, but that gives it back to us.

And most importantly, you get:

* To hear Jessica’s play theme music (at 55:00)

* To let us know if you want a Center Stage watch along (because as a millennial creative woman I’m shocked Meg hasn’t seen this seminal film of my 20s!)

* To see Jessica literally dancing on a hillside in Switzerland in 2007, because the hills were alive with the sound of music. (only on Substack, so come hang with us there)

In today’s episode

* Why play isn’t about escape—it’s about energy, iteration, and identity

* How we infuse our personal styles into our personal brands

* All of the things Meg has learned from the Museum of Play

* What our personal play styles reveal about how we lead, build, and rest

* Why we don’t play enough in our businesses

* Jessica and Meg’s various types of play (and even what we consider play)

* Center Stage and what it gets right about discipline, talent, and letting go

* How we’re experimenting in public: podcast shifts, newsletter redesigns, and more

* Why constraint is the secret to playful business design

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

You’ve been sold a load of garbage about what it takes to grow a business today. And in this episode of Aggressively Human, we’re getting back to the truth about sales.

Max Traylor—agency churn physician and LinkedIn truth-teller—joins us to break down why so much of what passes for “sales strategy” today was never actually working. (It just didn’t matter when money was cheap.)

We talk about how most of us have never learned (or needed to learn) real sales skills, why AI and automation are actually doing you a favor by making real humans stand out, and why your best sales strategy is still a damn phone call.

We also dive into what real client expansion looks like, how to expand your existing relationships (hint: the word you’ll stop using is “done”), and how agency owners and soloists can rebuild around human relationships instead of implementing software and tools that take us farther away from connections in search of "scale".

* The sales myths we’ve been sold by venture-backed tech startups

* The difference between "participating in a buying process" and actually selling

* The missed opportunity of existing clients and why client expansion is the sales strategy no one talks about

* How to start expanding your engagement from day one

* Why quarterly business reviews aren’t admin—they're about getting invited to the adult table

* How bad automation is making it easier for real humans to stand out

* Why we need to become indispensable partners—and how do we do that

* The sales "crisis" that was never new—it just used to be easier to hide bad sales processes when the market was hot

* Max’s philosophy on LinkedIn: do it for yourself, not for the likes—and why IP creation > audience chasing

About our Guest

Max Traylor: LinkedIn, Website

1,000 Routes with Nick Bennett Podcast Appearance

Resources Mentioned

Becoming an Indispensable Partner featuring Steve Lishansky (Beers with Max podcast)

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

“Nickelback had the last big rock song of our generation because songs just aren't counted the same way. So I feel like this is actually a fairly good example of: what is popular is Nickelback, but it's not the best music. It's not the critically acclaimed music. This is what gets played on the radio because it can be played while you're barbecuing and it's non-offensive.

And that's what AI-curated content is, it's the Nickelback of content.” - Meg

There’s a lot of pressure in online business to be original. To create something new. To be the thought leader with the freshest take. But much of what passes for “thought leadership” online is just recycled content, AI regurgitation, or the same tired takes with slightly different branding.

In this philosophy episode of Aggressively Human, we make the case for starting with curation, not creation, to avoid flat, forgettable content where we’re simply competing through the volume of our ideas (h/t Jay Acunzo).

We explore what it really means to be a thoughtful curator, how building taste builds your expertise, and why citing your sources doesn’t make you less of a thought leader but actually strengthens your positioning. We talk about what it actually means to curate well, why human curiosity is the root of all curation, the messy process of composting ideas, and how to make time—and intention—for escaping the algorithmically-driven echo chamber of ideas.

Plus hear us develop (in real time!) the five-step framework for becoming a trusted creator, why your “whisper of discontent” might be your next learning quest, and what it looks like to embrace your expertise without pretending to know it all.

If you’re tired of thought leaders who have more LinkedIn carousels than actual ideas, this episode is an invitation to reconsider curation as an integral pillar.

* Why consumption must come before curation—and why curiosity comes before both

* How to develop taste by reading, listening, and observing widely

* Our 5-stage content development process

* The difference between AI curation and human curation (and why AI flattens nuance)

* How “whispers of discontent” can guide your next learning quest

* Why citation is essential to expert thought leadership

* Curation as care: how to refer, recommend, and connect as a value-add to your ecosystem

* Why your best business moves might come from knowing the right referrals—not from knowing it all yourself

There's value in saying, “Here's a list of the different software that I've tried, but here's the best project management tool for this circumstance and for this circumstance and for this circumstance.” And there's an expertise in being able to help people strategize what the best choice is for them based on.

Your lived experience, your client experience: don't work with this person, work with this person. Don't read this book, read this book. I think that that's a huge part of what you and I do, especially in group coaching programs where we're able to say in real time, “Oh, because you are running this type of business, you should be running this type of marketing strategy, or you should have this sort of accounting practice in place.” - Meg

Prior Episodes Mentioned:

Resources:

* James Clear – cited the Helsinki Bus Theory (not the Stockholm Bus Theory!)

* Jay Acunzo – idea of “don’t be the best, be their favorite”

* Ira Glass – inspiration for early content creation and taste development

* Rob Harvilla – host of 60 Songs That Explain the '90s, used as a curation example

* Chris Guillebeau – founder of World Domination Summit, mentioned by Jessica

* Dani Gardner – coined “whisper of discontent,” mentioned from her book Quiet Marketing

* Lacy Boggs – mentioned for her conversation on what defines thought leadership

* Malcolm Gladwell – concept of “mavens” from The Tipping Point

* Kate Raworth – author of Doughnut Economics

* Rebecca Henderson - Reimagining Capitalism in a World on Fire

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

How do you protect what you’ve created when so much of what you’re creating lives online?

In this episode of Aggressively Human, we’re joined by Erin Austin, founder of Think Beyond IP, to dig into what intellectual property really is, what you can protect, and how to turn your expertise into an asset—not just a deliverable.

If you’ve been asking, “How do I protect my ideas?”—this is the episode for you.

* What counts as intellectual property under U.S. law (and what doesn’t)

* The difference between copyright, trademark, patent, and trade secret

* “But what if someone steals my stuff?”

* The moment a copyright becomes enforceable (and how to register it)

* What happens when you use AI to write, create, or ideate (and what that means for copyright)

* Why most service providers accidentally give away their IP in contracts, and how to fix it

* When and how to cite your sources ethically (even when it’s not legally required)

* How IP turns your expertise into leverage, whether you're licensing, scaling, or stepping out of the room

About our Guest

Erin Austin, LinkedIn

Think Beyond IP AI Workshop

Want to be the first to know when the next Masterclass cohort opens? Join the Priority Access List to receive early notifications and secure your spot before public enrollment opens. The paid masterclass is a three-session live training designed for experts with corporate clients who want to harness AI confidently—without legal headaches. Space is limited to ensure a premium, high-value, small-group experience so you get in depth, practical tools and expert legal guidance.

Other Resources

The Rookie Song

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

But what if you don’t want a million-dollar business? What if you want a smaller business that’s satisfying?

In this episode, co-host Jessica shares her framework for the “Zone of Enoughness”—a way to reimagine business growth not as endless expansion, but as aligned sustainability. Jessica and Meg talk about letting go of business models that don't fit, the very real trade-offs of growth, and why sufficiency might be more radical than abundance.

* Why “abundance” is still about chasing more—and how “sufficiency” offers a different way to feel at peace with your business.

* Jessica’s four-part Enoughness framework: money, time, flexibility, and creative autonomy.

* Why your business might look successful but still feel misaligned.

* The internal (and household-level) work of defining your minimums and maximums.

* Why responsibilities to your clients, team, and community shape your Enoughness Zone.

* How Jessica’s corporate background shaped her hustle—and how she’s learning to unwind it.

* What happens when your business hits its revenue high point and you still feel burned out.

* Why “seasonal” Enoughness matters: how your priorities shift over time (and why that’s OK).

* The emotional and energetic costs of infinite growth—and why rest is critical.

Resources Mentioned

Kate Holly’s The Space Beyond Scarce

Robin Wall Kimmerer: Braiding Sweetgrass, The Serviceberry

Staying Solo by Maggie Patterson

Connect with Us

Comment on Substack

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

Leaving social media has been an increasingly popular choice in the past few years. But is leaving always the most impactful choice?

In this episode, we sit down with Illana Burk, business coach and advocate for human-first business, to talk about the messy middle of visibility, values, and doing business inside systems you didn’t build.

Illana shares why she’s choosing to stay on social media; not because she’s ignoring the harm, but because of how social media is an important place our voices can be heard.

We unpack the compromises and contradictions that come with trying to do business ethically in a digital world—where every platform is flawed, no choice is pure, and the desire to get it “right” can quietly become a trap. Illana offers a grounded, generous perspective on what it means to market with integrity and show up with care.

* Why “just leaving” social media isn’t always the impactful move (and who wins if we do)

* The difference between marketing, community, connection, and consumption—and how social media serves each differently

* Why nuance, dialogue, and moral compromise are necessary parts of human business

* Why being ethical in business doesn't mean doing it perfectly, and what that actually looks like in practice

* Why presence—not performance—might be the best use of platforms in 2025

* The value of showing up in systems you don’t fully endorse, and how to do so with intention

About our Guest

Illana Burk

Illana Has Thoughts

Bread and Butter

The Good Business Podcast

https://illanaburk.substack.com/p/i-dont-really-love-social-media-but

Resources Mentioned

Re-imagining Online Business | Brooke Monaghan & Tristan Katz

The Digital Watercooler is Gone | Amanda Natividad

Lizzy Goddard

Connect with Us

Join us on Substack

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

This week, we go behind the scenes of a real launch with Dusti Arab, founder of Referral Worthy and longtime marketing strategist, to talk about what happens when a launch starts strong—and then doesn’t go to plan. Dusti walks us through what she planned for her latest launch, what actually happened, and how she adapted in real time by listening to her audience, adjusting her messaging, and staying rooted in what actually matters: relationships and referrals.

* Why Dusti built Referral Worthy for small business owners stuck in the feast-or-famine cycle

* What worked—and what didn’t—in her recent launch (plus what she’d do differently next time)

* How she used affiliate marketing to fill her challenge (and why it outperformed social)

* The realities of evergreen offers and how to make them successful

* The tradeoffs of free vs. paid launch events—and how to pick the right one for your goals

* How to serve different tiers of clients without burning out or diluting your offers

* Why thought leadership needs to come before a big launch

* The difference between a launch that flops and a launch that feeds your business in other ways

About our Guest

Dusti Arab

Referral Worthy

Resources Mentioned

Behind the Launch

Mike Ganino

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Substack: https://aggressivelyhuman.substack.com/

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

April MacLean joins Aggressively Human to break down what real community building looks like in 2025.

* Why most business communities fail (and why just starting a Facebook group won’t cut it).

* What must be present in a business before trying to build community.

* The three essential conditions that define a real community.

* The difference between a support forum and a true community (and why most businesses confuse the two).

* What happens when community managers abdicate leadership instead of shaping the space.

* Why exclusivity creates stronger connections—and how to keep your community from turning into a ghost town.

* The importance of rituals and rhythms that keep members engaged over time.

If you’ve been struggling to make your community thrive—or wondering if you should even start one—this episode is a must-listen.

About our Guest

April MacLean

How to People Newsletter: Where sharp eyes meet sharp wit: A weekly look at customer experience through a very human lens.

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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 there was another way to grow your newsletter, without relying on social media or paying high rates for ads to Meta, Google, or Microsoft/LinkedIn? What if you could put that money into the hands of fellow creators - and end up with a more aligned audience?

Dylan Redekop joins Aggressively Human to break down sustainable, ethical, and cost-effective ways to grow your newsletter—without handing money to Big Tech.

Dylan, a newsletter strategist and creator of Growth Currency, shares how he grew his newsletter, landed sponsorship deals, and helps other newsletter operators grow (in concert with Chenell Basilio) without relying on social media. We dive into cross-promotions, creator sponsorships, paid recommendations, and other overlooked strategies that help you grow an engaged audience by directly connecting with and investing in other creators.

If you’ve been struggling to expand your newsletter without relying on algorithms or expensive ads, today’s episode is a must-listen.

* Why newsletters and email marketing are not the same thing (and why it matters for your strategy).

* How to grow your newsletter without social media or Meta ads (including free and paid tactics).

* The right way to collaborate with other creators through cross-promotions, guest features, and swaps.

* The "hidden" world of creator sponsorships—how to sell and buy newsletter sponsorships the smart way.

* What not to do when growing a newsletter (and why some cross-promos kill audience trust).

* The truth about paid recommendations (how they work, who gets paid, and whether they’re worth it).

* How to use AI and automation to enhance your newsletter without losing your voice.

“This is the most meta thing. So you're having to do marketing to get your paid recommendation placed on other people's recommendations widget. Instead, this could be how it works: “Hey, I like you and I have the same audience. I will pay you if you put me as your paid widget.” - Jessica

Missed our last episode about consent- and agency-based newsletter practices?

Listen to our last episode about Email Automation with Heart with Bev Feldman:

About our Guest

Dylan Redekop, LinkedIn

Chenell Basilio’s Growth in Reverse Newsletter

Growth in Reverse YouTube, co-hosted by Chenell and Dylan

Growth in Reverse Community (say hi, Jessica is there!)

Post: How To Grow Your Newsletter without Social Media

Resources Mentioned

Josh Spector

Craft and Commerce (Kit Conference, Boise ID)

Jordan Gill - Systems Saved Me podcast

Justin Moore - Sponsor Magnet book

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

There are the illegal “no-nos”: the most egregious email practices that make us want to throw away our phones or hit the spam button. There are the morally gray areas of more manipulative email marketing, or just even a sub-par experience.

But in an aggressively human fashion, we can actually not just maintain but enhance our relationship with subscribers by incorporating consent-based practices like landing page customization, email customization, opt-outs, pauses, and segmentation.

In today’s episode, we explore the ways automation with heart can improve the relationship with your email list:

* The 7 deadly sins of email marketing (and why they’re costing you trust and engagement).

* How to define what email marketing tactics are aligned with your values.

* Why clear expectations in your welcome sequence are so important to set the tone with new subscribers, especially if they are joining from summits, bundles, or recommendations.

* How giving subscribers more choice actually makes your emails more effective.

* The consent-based practices that engage your subscribers in a deeper conversation.

* Why your best content is getting lost—and how to make sure new subscribers see it.

* How to use auto-responders to set boundaries, protect your time, and even generate revenue.

Missed our episode with Jeremy about his welcome sequence?

Get that here: https://aggressivelyhuman.substack.com/p/13-depth-as-a-feature-not-a-bug

“I am really big on being intentional and values aligned with how we do things. So, whereas I might have certain ways that I want to show up and certain tactics I don't feel good doing, that's not to say that they're wrong, off the table, and you shouldn't do them.

But if something doesn't feel good to you as a recipient, just because it's “best practices” doesn't mean that you should do it in spite of what your gut is telling you. I think really follow what feels good or doesn't feel good to you.” - Bev Feldman

About our Guest

Bev Feldman

Automate with Heart Newsletter

Additional Resources

Tad Hargrave’s Marketing for Hippies

Connect with Us

https://aggressivelyhuman.substack.com/

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

Operating at 150% capacity might feel like the norm, but that’s only because we’re operating with what Susan Boles calls “default decisions.” Instead, what if we focused on building businesses with margin. Yes financial margins, but going beyond those margins to include emotional and energetic margins?

“When you broaden your definition of margins, it gives your business a lot of expansiveness.” - Susan

Susan Boles, founder of Beyond Margins, helps business owners create sustainable, human-centered businesses that prioritize calm over chaos. Susan’s approach isn’t about sacrificing profit for peace—it’s about designing a business that works for you, not the other way around. She believes businesses should function at 50% capacity, so when the inevitable chaos hits, you’ve got the space to handle it.

In today’s episode, Susan shares how to create breathing room in your business, build systems that serve humans first, and let go of default decisions that lead to burnout. We talk about how Susan had to unlearn urgency, build in rest, and operate at odds of the default expectations of building a business.

In today’s episode, hear us dive into a calmer business:

* Why building margin into your business is essential and how it helps you weather inevitable chaos.

* The "puppy dog" approach to building your business network (and why curiosity and friendliness go further than you think).

* The difference between financial, emotional, and energetic margin, and how to build all three.

* How Susan’s “potato or tornado” work style inspired a business model that respects her capacity.

* Why default decisions are running your business (and how to make them intentional instead).

* How standardizing your services first makes automation more effective (and less of a mess).

Missed our episode about Simplicity over Systems? You can listen to that here: https://aggressivelyhuman.substack.com/p/11-simplicity-over-systems

About Our Guest:

Connect with Susan Boles

Listen to the Beyond Margins Podcast

Download the Services Swipe File

Connect with Us:

View the Full Show notes on our Substack: https://aggressivelyhuman.substack.com/

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

If your product - your podcast, your service, your course - isn’t good enough, no amount of marketing is going to make that product grow. And yet, most courses, cohorts, or even higher-priced coaching programs don’t get into the actual experience of your work. Many providers are just not in the business of experiencing your business and your product (because it’s not as scalable).

And so podcast strategist Jeremy Enns has changed his business model to address that core issue. Instead of zigging, focusing on growth through courses and membership - which, as a purchaser, are truly outstanding - Jeremy’s zagging. Instead, Jeremy is embracing depth, obsession over the product, and care.

Jeremy is the founder of Podcast Marketing Academy where he helps underdog creators and challenger brands punch above their weight by engineering scrappy, yet sophisticated podcast growth & revenue generation strategies and step-by-step marketing schematics. He’s originally from the cold, barren Canadian Prairies but now lives in sunny Barcelona.

In today’s episode, hear how Jeremy’s depth-first approach is changing his business and client results:

* Why no marketing strategy can save a product no one wants - and what to do about it.

* The ‘aggressively human’ way Jessica and Jeremy met way before Jessica had a business, and how that impacted our relationship.

* Jeremy’s evolution from a highly-scaled business model to a high-touch service: why he did it and what it’s unlocking for his clients AND for his revenue

* When obsessing over your work is a differentiating factor in your marketing and delivery (and why your clients will thank you for it).

* How caring (yes, really) is Jeremy’s most effective marketing strategy, including what Jeremy cares about (and what he doesn’t care about).

* The automations that keep Jeremy in touch with his audience without being on the content hamster wheel.

About Our Guest:

Follow Jeremy Enns

LinkedIn

Scrappy Podcasting Newsletter: https://podcastmarketingacademy.com/scrappy-podcasting-newsletter/

Podcast Marketing Trends Explained Podcast: https://podcastmarketingacademy.com/podcast-marketing-trends-explained

Podcast Marketing Academy YouTube: https://www.youtube.com/@podcastmarketingacademy

Resources Mentioned:

* The Do Lectures

* https://hiutdenim.co.uk/

* NeuroDiversion 2025 (the conference from the World Domination Summit creators)

Connect with Us:

View the Full Show notes on our Substack: https://aggressivelyhuman.substack.com/

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

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

You’ve probably noticed it—the emails that don’t sound quite right, the sales pages full of word salad, the content that feels like it was written by a robot. Because it probably was.

This week we’re talking with Jessica Mehring, founder of Horizon Peak Consulting, specializing in conversion-focused editorial content, campaign copy and content strategy for B2B tech companies. She is also an author, speaker, and university lecturer, and she coaches leaders and their teams how to grow trust with their own writing. Where should AI fit into the writing process - or should it at all? How is AI impacting our communication and creativity - and how we can use it for the better?

In today’s episode:

- How the mixing of AI and human communication is eroding trust, starting way before ChatGPT came on to the scene.

- Why everything that comes out of GPT sounds oddly similar (introducing Jessica L’s new favorite term language homogeny)

- The right ways to use AI to be a tool in your content without removing the soul of your writing or introducing bias.

- Why one moment of friction in communication can cause us to question our trust in a company.

- If you have to use AI because you’re in an firm with a mandate to do so, where and how you might use AI (and where to avoid).

- How women (and other underrepresented voices) are mobilizing for seats at the AI development table.

“We go check out the social media and it's just this robotic slop. I look at that and I see a minuscule moment of friction in the customer experience, but that moment of friction is all it takes for a customer to question. ‘Do I believe everything else I've read? Can I trust this company? Should I give them my money?’ One moment of friction in the customer experience across the spectrum of content is enough for customers to question their purchase. And you never want customers to question their purchase.” - Jessica M

About our Guest

Jessica’s Thought Leadership and Teaching

Trust Fall: The Communication Connection

Horizon Peak Consulting

Resources Mentioned

The Perception Gap: When is it okay to use AI in content, and when is it not?

Real Voices in your Ears

Connect with Us:

Subscribe to the Substack:

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

The alternative? Embracing Simplicity over Systems. Embracing Simplicity over Systems, another core Aggressively Human pillar. How can we be thoughtful about where and how we use systems to be in service, instead of just buying systems as a service.

And who better to bring in our episode is fellow Ops brain Nikki McKnight. Nikki McKnight (she/her) is an operations and systems strategist for creatives who want to develop operations & systems that create industry-leading experiences for their clients. And yes, she’s also Meg’s co-host on the romance podcast First Dates and Soulmates - because successful millennials need hobbies too, right?

In today’s episode, hear our discussion about the role of systems in an “aggressively human” business

- The definition of “systems” you hear 99% of the time and why that’s one of the biggest myths we’re busting

- Why a fully automated customer journey might be the worst thing for your business

- The systems investments we regret and the tools we couldn’t run our businesses without (including Nikki’s Ninja Dashboard)

- Why all three of us embrace a “tool agnostic” approach in how we talk about systems and automations with our clients (and why that helps both our clients and us!).

- How to avoid giving away power - in all its definitions - to software, contractors, or algorithms and keep agency over your business decisions.

- Ways to use automations to prevent (or in some cases add) friction to improve your client experience… but only if you know where and why that’s happening

“A system is … a vehicle for everybody involved in the ecosystem to make a decision. Whether that is me as a business owner, whether that is a member of my team, whether that is a client that I am working with, whether it is a member of my audience that is not yet a client or may not ever be, the whole goal here is how do we make decisions? That's it. Full stop.” - Nikki

About our Guest

Nikki McKnight: http://www.theopsshop.biz/

LinkedIn: https://www.linkedin.com/in/nikkimcknight/

Subscribe to FAFO: the systems newsletter for creatives who hate 'em: https://theopsshop.biz/fafo/

Resources Mentioned:

Donella Meadows - Thinking in Systems

Connect with Meg and Jessica

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