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

What happens when your content calendar makes you want to set your business on fire?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 chapterAbout our GuestMegan DowdConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

We often talk about launches as big, flashy events. But what happens behind the scenes when you’re not just releasing something new—but becoming someone new in the process?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 timeWant 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 LabContent Love LabConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

Let’s be honest, we started this podcast as AI skeptics — skeptical of AI to write and sound like us without falling into language homogeny, AI pitch slaps in the DMs, and using AI to replace our thinking.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.” - PrernaAbout our GuestContent BistroSkeptic Buyer BotConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

What happens after you leave a business you built? How do you relate to work, money, systems, and your nervous system when your entire identity has changed?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 soloAbout our GuestErika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-MakingConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

What does it take to walk away from something that’s “working”—even if it’s not working for you anymore?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 controlAbout our GuestErika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-MakingConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

When you're building something with a co-founder or even partners (like, say this podcast), it’s not just your business that needs tending—your relationship is the business.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-publishingAbout our GuestDr. Matthew JonesThe Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup SuccessMentioned ResourcesJohn and Julie GottmanImago TherapyNoam Wasserman’s The Founder’s DilemmaConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

Dive into the raw realities of online business as the hosts share their summer experiences, discussing the challenges of running Facebook ads and the nuances of retainer work. Discover how one co-host transformed a summer program from nine prompts into a vast resource library. They explore the harsh business model truth: success in selling and delivery rarely comes easy. With a new challenge on the horizon, find out how SEO and AI strategies are evolving to keep online visibility sharp. Their candid reflections offer a refreshing take on entrepreneurship.

“It's not, you know, oh, ‘I was working with these clients and then I was in the shower and while I was washing my hair, I had this great idea and I made a website.’ Like it's never that way, but that's how it looks on the outside.” - MegWe 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.” - SamanthaAbout our GuestSamantha Pollack - and join the “Get the Mixtape” newsletterThe Craft small group writing workshopSubstack: https://substack.com/@indiecopystudioConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

Entrepreneurship is hard. And it’s even harder when your nervous system is stuck in a mode that’s not serving you.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.” - ShulamitAbout our GuestShulamit Ber LevtovConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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

“Do you want to show up in those AI search results? Because AI is searching the internet now. AI is a search engine and it's looking at all those same things that Google is. So if you're not doing the [content] work, then you're being left out of that search.” - MegWhat 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.” - JessicaResources Mentioned:Diann Wingert: https://www.diannwingertcoaching.com/adhd-ish-podcastRyan Trahan’s 50 states in 50 days video: https://youtu.be/KTYbvU-aSf4?si=fCaJ3rZogru3hifUConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg 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