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Aggressively Human: Online Business in the Age of AI, Algorithms & Automations: Daily Summaries Delivered
by Meg Casebolt & Jessica Lackey
Aggressively Human is a podcast about building expert-led businesses around expansion, not extraction.Hosted by Meg Casebolt and Jessica Lackey, the show explores what happens when conventional business advice meets the reality of the people who actually have to live with its consequences.We talk about sustainable growth and business models, marketing and algorithms, AI and automation, expertise and authority, mental health and capacity, relationships, and the choices underneath all of it: What are you optimizing for? What do you gain? What does it cost? And does the tradeoff make sense for the actual humans involved?We’re not here to prescribe a new set of rules for running your business. We’re interested in helping independent experts make thoughtful decisions about what to grow, what to automate, what to protect, and what they want their businesses to make possible.Because your business should support your life. Not the other way around. <a href="https://aggressivelyhu
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- 2 days ago18 min
Bonus: AI Changed What Search Rewards [from Love At First Search podcast]
Today’s episode is a little different.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 jobhow AI search evaluates sources and expertise differently from traditional searchwhy clear, explicit expertise matters more than simply publishing more contentwhat zero-click search changes about how we measure visibilitywhy being recognized by AI is not the same thing as being recommendedwhich SEO fundamentals still matter even as the search experience changesIf 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 housekeepingAggressively 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/ 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
- 1 weeks ago48 min
The week we almost ended Aggressively Human
There’s a so-called “best practice” for most business podcasts: release every week, book guests for about half your episodes, and don’t break the algorithm. This fall, keeping up with those rules nearly ended this show, so we stopped and asked what version of the podcast makes sense for us two years in. 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.” - MegConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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
- 2 weeks ago1h 3m
Running a community like a house party with Darnell Brown
Is your community a quiet library? Or a lively house party? And how do you design and market a community designed for the goals of you and your members?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.” - DarnellAbout our GuestDarnell BrownForgeConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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
- 3 weeks ago52 min
The role of a website with Eleanor Mayrhofer
Anyone can spin up a website with AI now. But for experts who built their careers offline, the hard part was never the tool. It’s knowing what to publish, where, and why.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.” - EleanorAbout our GuestEleanor MayrhoferConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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
- Oct 8, 202656 min
Our fall launches: What worked, what didn't, and what changed mid-launch
Spoiler Alert: Neither of us “sold out” our fall launches. But looking at who joined and why, we don’t think that’s the whole story.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.” - JessicaProgramsDeeper Foundations MembershipSignal MentorshipConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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
- Oct 1, 202655 min
“How do I know what I sound like” with Samantha Pollack
Most of the conversation about AI and writing is stuck on whether it can write well. Samantha Pollack thinks that’s the wrong question. The one that matters for your business is whether it can write like you, and whether you’d recognize your own voice if you saw it.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.” - SamAbout our GuestIndie Copy StudioAnarchy on the Blank PageConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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
- Sep 24, 202654 min
Brand Voice vs. AI Voice with Justin Blackman
Most of us can spot AI-written copy now, even if we can’t say exactly why. With tools like Pangram scanning content for it, sounding like the default has real consequences, and a clearly defined brand voice is one of the best ways to sound like a specific person again.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 BlackmanAbout our GuestJustin BlackmanVoice Finder Connect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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
- Sep 17, 202657 min
Humanizing Data (and Strengthening Sales) with Tanisha Tate Woodson
Most research gets done to communities: someone extracts the data, publishes the paper, and is never heard from again. Tanisha Tate Woodson built a firm on the opposite premise — and then did the less glamorous thing, which was turn that premise into an actual codified method.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 WoodsonAbout our GuestWoodson InsightsConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica 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
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About Aggressively Human: Online Business in the Age of AI, Algorithms & Automations
Aggressively Human is a podcast about building expert-led businesses around expansion, not extraction.Hosted by Meg Casebolt and Jessica Lackey, the show explores what happens when conventional business advice meets the reality of the people who actually have to live with its consequences.We talk about sustainable growth and business models, marketing and algorithms, AI and automation, expertise and authority, mental health and capacity, relationships, and the choices underneath all of it: What are you optimizing for? What do you gain? What does it cost? And does the tradeoff make sense for the actual humans involved?We’re not here to prescribe a new set of rules for running your business. We’re interested in helping independent experts make thoughtful decisions about what to grow, what to automate, what to protect, and what they want their businesses to make possible.Because your business should support your life. Not the other way around. <a href="https://aggressivelyhu
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