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

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. aggressivelyhuman.substack.com (https://aggressivelyhuman.substack.com?utm_medium=podcast)

Publisher

Meg Casebolt & Jessica Lackey

Category

business · technology

Language

en

Explicit

Yes

First episode

24 Nov 2024

Latest episode

1 Oct 2026

Latest episodes

7 of 91 episodes have a transcript.

1. 

   1 Oct 2026

   “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 (https://indiecopystudio.com/). 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 (https://indiecopystudio.com/) Anarchy on the Blank Page (https://indiecopystudio.kit.com/blank-page-anarchy) Connect with Us Listen on Spotify (https://open.spotify.com/show/1889SeZ3oHLCdQ7Y796T0i?si=1ce2a79ee0c44e26) Listen on Apple Podcasts (https://podcasts.apple.com/us/podcast/aggressively-human-online-business-in-the-age-of/id1781558167) Meg Casebolt (https://loveatfirstsearch.com/) Jessica Lackey (https://www.deeperfoundations.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 (https://aggressivelyhuman.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

2. 

   24 Sept 2026

   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 (https://justinblackman.com/), creator of Voice Finder (https://justinblackman.com/voicefinder/) 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 (https://justinblackman.com/) Voice Finder (https://justinblackman.com/voicefinder/) Connect with Us Listen on Spotify (https://open.spotify.com/show/1889SeZ3oHLCdQ7Y796T0i?si=1ce2a79ee0c44e26) Listen on Apple Podcasts (https://podcasts.apple.com/us/podcast/aggressively-human-online-business-in-the-age-of/id1781558167) Meg Casebolt (https://loveatfirstsearch.com/) Jessica Lackey (https://www.deeperfoundations.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 (https://aggressivelyhuman.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

3. 

   17 Sept 2026

   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 (https://www.woodsoninsights.com/) 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 (https://www.woodsoninsights.com/), 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 (http://woodsoninsights.com) Connect with Us Listen on Spotify (https://open.spotify.com/show/1889SeZ3oHLCdQ7Y796T0i?si=1ce2a79ee0c44e26) Listen on Apple Podcasts (https://podcasts.apple.com/us/podcast/aggressively-human-online-business-in-the-age-of/id1781558167) Meg Casebolt (https://loveatfirstsearch.com/) Jessica Lackey (https://www.deeperfoundations.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 (https://aggressivelyhuman.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

Inside a recent episode

Trust is the New Currency: A Craft+Commerce conference debrief

Published 24 Jul 2025 · Transcript excerpt

[…] I had this conversation with them and you didn't have to consult your role at X or your note cards or your phone. You have that sort of mental role at X always rolling. Well, yes, but also, I connected with all these people on LinkedIn and I made it a point to engage with them throughout the year. So I didn't have to remember them from a year ago. I remember them from the post they made two weeks ago on LinkedIn, because I've been -I've made it an intentional point to not just like try to get engagement on my posts, but to actually be like, these are people who I'm in community with. Like, let me engage with them throughout the year so I don't have to remember, oh, we had this conversation last year. […]

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