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

While AI still can’t fold your laundry, it can help you build a business that runs smarter—and a life that runs smoother. In this episode, Jessica and Meg talk with Mary Williams, the librarian-turned-tech director behind Sensible Woo and the new Sasquatch Media Grounds studio in Portland. From haunted recording spaces and tarot cards to spreadsheets and AI bots, Mary shows what it looks like to blend intuition with technology.She shares how she built her “AI team”—including Remy, the snarky Gen Z assistant who filters her inbox and protects her calendar—and why she treats her chatbots like departments inside her business. They talk about how AI can help reduce emotional labor, from grocery budgets to health tracking, and what it means to build systems that keep the human at the center.This conversation is filled with practical ways to make AI feel less robotic (and maybe a little more like a helpful intern who swears), while lightening your load with technology that actually serves you.* Mary’s path from librarian and tarot reader to tech director and business coach* How she organizes AI “staff” into departments—finance, operations, marketing, and more* The surprising power of giving your bots names and personalities* Why AI reveals more about your delegation habits than you think* How to build an AI “board of advisors” with personas like Mark Cuban or Reese Witherspoon* Emotional patterns people bring to technology (and what that says about leadership)* Creative personal uses for AI—from meal-planning and purchasing decisions to health tracking“I would argue if you had an intern, if you had a Gen Z Remy with you, you’d still fact check them because they’re young, they’re learning. I need to make sure that everything’s right. And in that sense, you’re still doing the same functions, you’re not doing less, you’re really not doing more. It’s just moving along faster.” - MaryAbout our GuestMary Williams: Sensible Woo | Sasquatch Media GroundsYou, Me ChatGPT WorkshopListen 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

Jessica Lackey, author and consultant, shares her insights on practical business strategies for solo and small business owners. Frustrated with empty motivational advice, she created a systems-based framework in her book, emphasizing context over cookie-cutter tactics. The conversation highlights the pitfalls of popular business books, the myth of scaling as the only path, and the importance of ethical pricing. Jessica's goal is to provide actionable guidance that respects the unique challenges faced by individual entrepreneurs.

What happens when our usual ways of dealing with conflict stop working (if they ever worked)?In this episode, Shivani Mehta Bhatia joins Aggressively Human to talk about the changing nature of conflict—especially in a world shaped by grief, uncertainty, and fraying trust.We explore how conflict has shifted post-2020, how our nervous systems are adapting (or not), and why repair feels harder than ever. We talk about Shivani’s approach of “conflict midwifery,” destructive versus generative conflict, and what it means to build and lead with more care in increasingly reactive times.Whether you’re navigating tension in your team, your audience, or your closest relationships, this conversation offers a more humane way through.* What conflict looks like now—and why it feels more brittle* The 5 parts of Shivani’s “prism of conflict”* What “conflict midwifery” means and how it changes the repair process* What ChatGPT says are the fixes of our current polycrisis* What it takes to repair when there’s no shared script* What’s the smallest possible actions we can take in conflict* Leading and relating in a time of collective dysregulation* How we can prepare—not avoid—hard conversationsAbout our GuestShivani Mehta BhatiaMonthly Conflict ClinicConnect 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 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.