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

Meg Casebolt & Jessica Lackey
  • 5.0 (4)
  • TECHNOLOGY
  • UPDATED WEEKLY
Aggressively Human: Online Business in the Age of AI, Algorithms & Automations

In a world focused on more: more content, more followers, more marketing, more scale, more noise… we’re facing less trust, less contact, less reach. We’re drowning in AI-generated slop, being pitch-slapped by “personalized” email funnels that couldn’t be farther from authentic, and struggling to be seen by a pay-to-play algorithm. It’s never been easier to create and connect more cheaply and at more scale, with less trust and more skepticism. But for experts and service-based businesses? We’re seeing the pendulum swing back. The answer isn’t to play by these trends. It’s to be **aggressively human.** aggressivelyhuman.substack.com

  1. Depth as a Feature, Not a Bug: Winning clients through genuine care with Jeremy Enns

    2 DAYS AGO

    Depth as a Feature, Not a Bug: Winning clients through genuine care with Jeremy Enns

    In a sea of marketing advice and growth hacks, let’s address the elephant in the room. What if the product is the problem? 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

    46 min

  2. FEB 13

    Who gets human thoughts? The Fight for Trust in Content with Jessica Mehring

    “It's because even if you end up completely rewriting it, it starts out without the human soul. And it's really hard to add the human soul. But if you can start with even the messiest human written draft, and then use AI to make it better, it has human soul to begin with, and it just ends up a much more human and resonant piece of writing.” - Jessica M 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

    46 min

  3. FEB 6

    Software in Service: Simplicity over Systems with Nikki McKnight

    Who hasn’t set up a system (or hired someone else to do so) that seems to make your efficiency dreams come true... and that just didn't happen. Or worse? Broke your business. 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

    56 min

  4. JAN 30

    When a week feels like a year: January 2025 State of Play

    “So maybe we're leaving or maybe we're staying, but we're staying as a person versus as a business owner. But then everyone is scattering. As a business, how are we marketing to people when it's diffuse? And then as a person, it's like, well, where's everyone going now? And how can I be there with my friends?” - Jessica Every year, it feels like January is just the longest month ever. But this year has felt like a whiplash between the beginning of the year until recording on January 24, 2025. Meta policy changes, TikTok ban and un-ban and more. So we’ve broken from our schedule to cover a special “January 2025” state of play in the world of AI, algorithms, and automations. We don’t have answers, because nobody does. We just simply have questions, and thoughts about how we might navigate this season. But hopefully this conversation can give you some food for thought about the questions we’re asking, and how these changes might have long-term ramifications on your overall marketing strategy — and mental health. In today’s episode we discuss: - The shifting currency of power: why attention is the world’s most valuable resource - The cost of building your business on rented land, and what happens when the platform changes overnight - The thorny questions around staying or leaving social media platforms - What costs we might pay to leave the “free” platforms - How your potential client behavior factors into where you can connect with them, and how to operate when that’s not necessarily where you want to spend time - Why discernment is the word of the year when it comes to choosing where to put your time and attention Join the Convo on 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

    1h 1m

  5. JAN 23

    "PIVOT!!" How to navigate a changing business landscape with Lacy Boggs

    “AI cannot come up with new ideas. It can paste things together in new ways perhaps, but it's still it's still the monkeys on the typewriters, right? It's still the infinite monkey thing. It's just mashing together old ideas in new ways perhaps, but it can't come up with truly unique new ideas.” - Lacy Boggs This week, we’re talking with Lacy Boggs, founder of the Content Direction Agency but also has done every business model in the online entrepreneurship space. We talk pivots, thought leadership, and how to stand out in the age of more content than ever. In today’s episode we cover: - How Lacy has decided what she wants to be when she grows up (and why her eulogy won’t be “I wrote marketing copy”). - When should you pivot and descale and how that impacts your relationship to your body, your business, and marketing - Where the human element is non-negotiable in coming up with new thoughts - not just AI mashing together old ideas - The distinction between thought leadership and thought performance - and how to move beyond LinkedIn hot takes and selfies - What tools are in Lacy’s toolkit in order to curate, compost, and communicate new thoughts and ideas “I don't want AI to do my art and thinking - I want it to do my dishes and get my groceries, right? I want it to do the menial things so that I could do the art, and that's where I think we're probably going wrong.” - Lacy Boggs About Our Guest: Follow Lacy Boggs: https://lacyboggs.com/ Lacy’s Content Solution The Thought Leader Lab Resources Mentioned: Writing Down the Bones by Natalie Goldberg Braiding Sweetgrass by Robin Wall Kimmerer Black Oracle Goddess Within Oracle Deck Inoreader - Build Your Own News Feed Readwise 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

    49 min

  6. JAN 16

    "Where everybody knows your name": the power of community over commodity

    “I don't want to calculate my churn without knowing every single person who leaves.” - Meg For businesses like ours, community is the lifeblood of a strong business. And when we are talking about community, we’re not just talking about an online platform where you can post in a forum. We’re talking about, as Meg says, “people who give a sh*t about each other”. In today’s podcast, we dive into the Aggressively Human philosophy of Community > Commodity. - Why being part of a community where everybody knows your name is a business advantage, not just a feel-good moment. - The difference between real community and what most online businesses call "community" (hint: it’s not a forum or a membership site). - How reciprocity flips the script from one-off transactions to a gift economy that ripples and expands out farther than you can see. - Why community is so "hot" right now—and why it’s impossible to maintain if you’re only in it for the money. - How pools, hubs, and webs are more than just metaphors—they’re frameworks for how communities are shaped - The problem with treating your clients as commodities and what it really takes to create loyalty and trust. - How community creates shared values and language that lead to better retention, referrals, and results. Mentioned in the Episode: Getting Brand Communities Right (pools, hubs, webs metaphor) Expert Up Club - Dr. Michelle Mazur A Wild New Work Podcast - Megan Leatherman Referral Worthy Podcast - Dusti Arab Savvy Social School (now the Mindful Marketing Lab) - Andreá Jones Mighty Networks People Magic - Gina Bianchini Connect with Us: Comment on 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

    49 min

  7. JAN 9

    Real voices in your ears: Human-centered podcasting with Amelia Hruby

    The act of podcasting - recording it, editing it, and listening to it - is one of the most embodied acts in content creation. Because no matter how good the AI bots sound, there’s something simply human about listening to someone else’s authentic voice in your earbuds. Today’s interview is with amelia hruby, founder of Softer Sounds podcast production studio and host of the Off the Grid podcast. Amelia has some strong points of view about AI in the podcasting industry, and the power of a human-oriented podcast process. In today’s episode we dive into: - The power of podcasting to bring our ideas to life and build trust in a way that is distinct to writing - Why Softer Sounds leads with the voice in all aspects of the creation and production process (not just in the editing process) - What happens when you take your magical, unique, sparkly creations and run them through AI processing and show notes (hint - they become dull, generic, choppy, and overly polished). - How Amelia leads with her human-first and audio-first values - and how that is a powerful filter for the clients she works with - The less obvious way you market and sell a higher-touch - and higher-cost - level of service - The unexpected benefits from having multiple people on the other end of the podcast production process “I built a lighthouse in my business that isn't really about podcasting, but brings to me people who are willing to ask hard questions about how they're willing and want to show up in their business” - Amelia About Our Guest: Follow Amelia Softer Sounds Off the Grid Podcast All of Amelia’s Other Podcasts! Connect with Us: Subscribe to the Substack and get the full show notes: 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

    46 min

  8. JAN 2

    Stop yelling into the echo chamber: Engage in Dialogue over Monologue

    Dialogue over Monologue: Our next Aggressively Human pillar. AI and automations can make it easy to have “faux-dialogue”: where you’re sent tons and tons of “personalized” emails, or you think you’re having a conversation with someone but you’re really just talking to an AI agent or a bot. And dialogue comes with risk: when you open up your world for real conversations, you might hear “no” or get people disagreeing with you. In today's podcast we dive into: - Why we might shy away from dialogue, but why Meg and Jessica chose this as a core Aggressively Human philosophy - When you might actually choose automation over dialogue - How dialogue reduces the gap between your ideas and real feedback (and why shouting into the void won’t get you there) - Why we decided to co-host this podcast (and how we rely on each other and other colleagues in our work) - The power of real time listening in order to pivot to the market (and keep making sales) 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 Resources Josh Spector’s For the Interested newsletter 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

    49 min
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5
out of 5
4 Ratings

About

In a world focused on more: more content, more followers, more marketing, more scale, more noise… we’re facing less trust, less contact, less reach. We’re drowning in AI-generated slop, being pitch-slapped by “personalized” email funnels that couldn’t be farther from authentic, and struggling to be seen by a pay-to-play algorithm. It’s never been easier to create and connect more cheaply and at more scale, with less trust and more skepticism. But for experts and service-based businesses? We’re seeing the pendulum swing back. The answer isn’t to play by these trends. It’s to be **aggressively human.** aggressivelyhuman.substack.com

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