Aggressively Human: For experts choosing expansion over extraction.

Meg Casebolt & Jessica Lackey
  • 4.9 (13)
  • Technology
  • Updated Weekly

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. aggressivelyhuman.substack.com

  1. 4d ago

    “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.” - 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 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. Sep 24

    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 Blackman About our Guest Justin Blackman Voice Finder 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

  3. Sep 17

    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 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

  4. Sep 10

    Cold outreach... as a human?!?

    Most of us have a very specific image of cold email: a stranger who never heard of us, selling something we never wanted, in language no human being would actually use. But “cold email” just means an email to someone who doesn’t know you yet—and the version most of us are reacting to is only one way to do it. 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 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

  5. Sep 3

    How we designed our fall programs (and who they're actually for)

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

  6. Aug 27

    Why We Need a Party for Our Failures with Jess Manuszak

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

  7. Aug 20

    The secret to becoming referable

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

  8. Aug 13

    Making a lifetime of work legible with Jessica Abel

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

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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. aggressivelyhuman.substack.com

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