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

“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

Everyone has been in bad meetings—and for many of you, being trapped in terrible meetings is one reason you became an entrepreneur in the first place.But what if meetings, and workplace culture generally, didn’t have to be awful? What if we could bring energy and collaboration, like the kind we get from a well-facilitated workshop, into our day-to-day culture?In this episode, Alison Coward joins Aggressively Human to show what it really means to lead through a facilitative and collaborative lens—not just to make meetings more efficient, but to make collaboration more human. We explore the difference between participation and true engagement, and why a good facilitator doesn’t just run the meeting—they make space for decisions, disagreement, and trust.And we also confront the realities of AI in the workplace. Because AI can craft the agenda and synthesize the notes… but can it feel the charge of conversation? And what do we lose when we outsource the hard conversations to software that avoids conflict and resilience building?* What “workshop culture” really means—and why it’s not just for facilitators* Why great collaboration isn’t about airtime, it’s about alignment* How to lead across generations when work expectations aren’t the same* The role of facilitation in navigating polarized teams and hard topics* Why AI can’t replace the discomfort, nuance, and trust-building of real conversation* The hidden labor of designing meetings that actually lead to decisions* Why clarity isn’t always the goal—sometimes it’s about making space for complexity* How to tell when your team needs a better process (not another tool)“When we default to using those tools, we're robbing ourselves of the chance to build those very human skills that enable us to relate to each other more effectively. Conversations are difficult. They're meant to be, that's why they're called difficult conversations. And sometimes the process of going through that difficult conversation hones and smooths the edges off. It's almost like a process that we go through that doesn't feel uncomfortable when we get to the other side. We've learned something new and perhaps we've built a connection with someone else. And the thing is, is that those kinds of difficult conversations or those situations are the very thing that people are like, oh, AI can do that for me now because they wanna avoid that uncomfortable feeling.”About our GuestAlison Coward and NewsletterLinkedInWorkshop Culture: buy directly from www.practicalinspiration.com or indiepubs for US customers and use code WRKCULT30 for 30% discountConnect 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

Jessica goes to conferences a lot, especially more now that she’s not employed full time. This is her eighth creator conference (4 World Domination Summits, 2 Craft and Commerces, 1 Neurodiversion summit, The Lab Offline, and a number of small mastermind and coaching retreats).So today’s episode is both a debrief on going to conferences and also a recap of the 4 takeaways from Craft and Commerce that are informing our year ahead.We dig into conferences:* Why putting yourself in the position to meet people can help you meet your internet heroes… and can also help you sell more things. (Shoutout to former guest Jeremy Enns here).* How does one maintain relationships with people so that the next years of the conference just get better and better?* Why presentation-heavy conferences miss the point, especially for more seasoned attendees (and how to think about the composition of the audience).And then, we dig into the four takeaways from the conference itself.* We’re entering into an AI content doom loop.* What’s your “use and refuse” AI strategy?.* Storytelling reigns supreme.* There is no “overnight success”.“If they don't exist, they will in the next six months is a tool that if you list a number of the influencers you wanna follow and comment on their post… and so you just feed it into an AI tool and that AI tool will come up with an AI generated comment. So you don't even have to log into LinkedIn. If this doesn't exist, I guarantee it will in like the next six months. You wouldn't even have to log in to see what your favorite influencer posted and the AI comments on their stuff so that your stuff feeds goes into the feed.And, some AI tool is gonna go into your library of content that you've created already, and it's gonna snip out something, drop it on LinkedIn, some other bot is gonna comment on it, and then there's no human involved in some of that stuff, period.” - JessicaMentioned ResourcesPamela SlimJeremy Enns’s Content Strategy SchematicNeurodiversion ConferenceShe’s so Lucky with Les AlfredConnect 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

Partnerships are everywhere in small business: business partners, project collaborators, behind-the-scenes co-creators, podcast co-hosts (hear our origin story!). But we don’t talk enough about what makes them actually work. If managing yourself is hard, imagine navigating the commitment (and the scheduling tetris) of two people.Emma Whittard (mindset coach) and Karen Worthy (executive career transition coach) had their “business meet cute” in one of Jessica’s classes. What started as simple client referrals turned into collaborations, a shared offer, and even Emma supporting Karen’s business behind the scenes. From the first casual chat to co-creating paid offers, sharing clients, and navigating logistics (like money, time zones, and email volume), we talk about how they built trust without a contract, how they make decisions, and what it means to do good work together.We talk about the emotional labor of collaboration, the unspoken agreements, and what it takes to prioritize relationship over revenue in a world that teaches us to keep everything transactional.Before teaming up with someone, listen to the foundation of what makes this collaboration work.* How a casual class connection became a long-term collaboration* Why their “Base Camp” offer came after the referrals, not before* What they’ve learned about setting boundaries, expectations, and pricing* The value of emotional support, operational partnership, and sounding boards* Navigating logistics: scheduling, tech, shared values—and the messy middle* Why trust (not contracts) is what makes these kinds of partnerships work“We also both said upfront that our relationship was more important than the business together. So the relationship first. That means that hopefully we won't get into a situation where there's something icky happening and we can't address it, or it sort of ruins things. So again, it is back to values and priorities again.” - Emma WhittardAbout our GuestsEmma Whittard | LinkedInKaren Worthy | LinkedInBase Camp OfferConnect 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

In this episode, we dig into the realities of running a relationship-led business in a market that’s no longer in beginner mode. Michelle Warner joins us to talk about what’s changed (and what hasn’t) in a world where quick wins and easy opportunities are drying up, and why now more than ever, the boring stuff—fundamentals, relationships, offers that fit—really matters.We cover how to adapt to a maturing market, where the “growth hacks” of the past aren’t working like they used to. Michelle shares why most client issues aren’t massive strategy problems but small, foundational misalignments—and why fixing them starts with a return to the basics.This is an episode for anyone feeling like what used to work just… doesn’t anymore. And for those ready to stop chasing the next big trick and return to the very unsexy, very effective roots of sustainable business.* Why the market isn’t broken—it’s just finally maturing (and your tactics need to, too)* The real reason your sales aren’t working (hint: it’s not because you’re not posting enough)* The problem with marketing arbitrage plays (Substack, LinkedIn newsletters, bundles—you name it)* Why your offer math might be the real problem behind your revenue plateau* How AI is making everyone sound the same—and how to stand out by being specific* Why the boring fundamentals are the most effective thing you can do right now* What to do instead of panic-posting when leads slow down“That's the key to relationships. The specificity and the “because statements” allow you to also build sticky relationships. So a lot of times when we're networking a, we don't know why we're networking with people, so we end up just meeting people and then trying to force square pegs into round holes, and b. so then you get stuck in these small talk traps.” - Michelle WarnerAbout our GuestMichelle WarnerSequence over Strategy podcastConnect 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

This week, we're doing something a little different. Instead of our usual dialogue, we’re sharing two short solo segments originally recorded for the Evidence of Humanity audio summit, hosted by Michelle Pontvert. This means we get a break from recording and editing but you still get a fresh episode. While because as Meg says, “Jessica loves a cadence”, taking breaks and thoughtful repurposing of content lets us take breaks and be aggressively human!First, Jessica shares how running free monthly workshops—starting with just four people—has become one of the most grounding, trust-building practices in her business. Not because they’re optimized for conversion, but because they create real-time space to test ideas, teach generously, and build actual relationships.Then, Meg takes the mic to talk about the surprising overlap between SEO strategy and romance novels. Drawing from her writing practice and deep love of story, she maps the early stages of the hero’s journey onto the buyer journey—and shows how thoughtful content meets people where they are, not where your funnel wants them to be.Let us know: do you like some shorter, solo episodes in your feed?We’ll be back next week with more dialogue!Connect 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

How do we build businesses and community inside a broken system—without replicating that system in our own work?By leading through an intersectional, feminist, and collective lens.In this episode, we talk with Becky Mollenkamp about what it means to build and lead this way: grounded in shared power, mutual care, and collective growth. Becky shares how her work as a coach and podcaster has evolved over the years, why she’s no longer trying to “go it alone,” and how building in community has been the most liberating move of all. We also talk about what it really means to earn money ethically, challenge systems without burning out, and keep showing up (even in the chaos of summer).We also get into the behind-the-scenes of launching multiple podcasts, navigating Substack and social media with ethics intact, and the real tension of building a business when you care deeply about people and want to pay your bills without selling your soul.This is a conversation for anyone trying to build something different in a world that rewards “the one right way to build.”* How Becky’s proximity to the Ferguson uprising catalyzed a shift in her perspective* The real difference between commerce and capitalism (and why most pricing models get this wrong)* What it means to build a business rooted in mutuality, not hierarchy* What the hell to do with Substack, Meta, and other imperfect tools* The behind-the-scenes of stewarding multiple podcasts, and the choice to have a co-host or not* The problem with trying to do it all alone—and how Becky’s moving toward collective action over solo growth* Why podcasting might just be the most human way to have the conversations we actually want to have“Yeah, I can come up with lots of ideas, but they're always richer when it's done in collective with these other women who have different lived experiences than me. And then, yeah, I'll move the ball forward. I love moving the ball forward, but I'm more excited now. I'm moving the ball forward with these ideas that are so much more richer.” - BeckyAbout our GuestBecky MollenkampFeminist Podcasters CollectiveFeminist FoundersMessy LiberationAssigned ReadingMentioned ResourcesTema Okun’s EssaySacred Economics by Charles EisensteinThe Soul of Money by Lynne Twist“The Master’s Tools Will Never Dismantle the Master’s House” — Audre LordeConnect 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

Most business advice assumes you're wired like everyone else. What if you're not?In this episode, we sit down with Diann Wingert—former therapist, business coach, and host of the ADHD-ish podcast—to talk about what it really means to build a business that works with your brain, not against it.We unpack the myths around ADHD, how to radically accept your own wiring, and what happens when you finally stop trying to “fix” yourself and start designing systems that fit you.Jessica and Meg share their own neurodiverse workarounds (including why their assistants actually manage them), and Diann breaks down how she flipped her brand, rethought her support systems, and uses tools like Claude.ai as external executive function—not a replacement for her brain, but a co-pilot for organizing all the genius.This one’s for the quirky kids, the not-quite-diagnosed, and anyone who’s ever tried to follow business advice that wasn't designed for their brain. * Why Diann rebranded her podcast and business to center ADHD-ish, not as a niche but as a reality* How radical self-acceptance (not self-awareness) is the real first step to change* The business systems that work because they’re nontraditional (like letting your assistant be the boss)* Why “It depends” is the real ADHD business motto* How tools like Claude and Notion help organize brilliance without replacing your voice* Why standard business advice falls apart when your brain doesn't fit the mold* What Diann learned from neurodivergent-friendly spaces (hello, marching band at a conference) and how to bring that into your own business model* The role of AI in organizing, not empathizing—and why therapy still needs a human touch“Human beings, by and large, are damaged through relationships, abuse, neglect, trauma. Most of the things that bring people to a therapist happened as a result of some failure of human nature. And so the whole transformation of therapy is that it is using the professional use of self. We are harmed by humans. We are healed by humans. It’s one of the most intimate and powerful ways of working. And I loved it.” - DiannAbout Our GuestADHD-ish PodcastMastering Your Entrepreneurial ADHDDiann Wingert’s LinkedIn NewsletterConnect 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 really mean to “stay solo” in a world that won’t stop telling you to scale? That’s the question we explore with Maggie Patterson, whose new book Staying Solo challenges the endless drumbeat of “bigger is better.”In this episode, we dive into Maggie’s journey from agency owner to solo business advocate, the messy parts of writing (and marketing) a book without turning it into a performative launch, and the very real tension between wanting to build a sustainable business—while feeling pressure to do it in a way that exploits your time or other people’s labor. (Thanks, online business influencers).We also talk about typos in print books, sticker packs as marketing tools, and why self-publishing may outperform traditional publishing as a soloist. Whether you’re a solopreneur, a micro-agency owner, or just someone wondering if you have to scale to be legit, Maggie’s perspective offers a breath of fresh air—and a permission slip to do it your way.* Why Staying Solo matters—especially when the default advice is always to “scale”* The tension between running an agency and telling others not to build one* How Maggie’s book journey came out of years of blog posts and a poolside conversation* The ethics of pricing, paying others well, and not replicating exploitative business practices* The weird relief (and panic) of finding typos in a printed book you can’t easily fix* How to stay human while promoting a book (sticker packs, handwritten notes, book tours)* Book marketing vs. book selling—why Maggie chose self-publishing and what surprised her most* The privilege of staying solo—and how to be clear about who you want to serve* Most importantly, the 5 book names for Maggie’s book themed birdhouse.About our GuestMaggie PattersonStaying SoloConnect 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

In this riffy, delightfully unstructured episode, Jessica and Meg ditch the outlines, frameworks, and “polished” content in favor of a real-life check-in, some AI trivia, and a sneak peek at Jessica’s summer program, Relationship Rhythms.We talk about how building relationships is about more than just dropping into people’s inboxes—and how Relationship Rhythms is designed to bring playfulness (and prizes!) back into the process. Jessica shares why she’s finally running an asynchronous offer and how Relationship Rhythms is different from her usual programs, plus what happens when you go from dreaming to launching.We also get real about our own partnership: the messy business of joint ventures, what happens when your business is in a different gear than your friend’s, and how to talk about money and collaboration in a way that feels human.And because she couldn’t resist, Meg quizzes Jessica on AI trivia—highlighting the joys, the contradictions, and the occasional panic about what AI knows, what it doesn’t, and how we’re using (and refusing) it in our own businesses.If you’ve ever felt like your business friendships are an ever-evolving dance—or wondered how to balance AI curiosity with human connections—listen in. 🍊PS. If you made it to the end of this episode, drop our Easter Egg word on Substack as a comment to let us know you’re here for the rambles, not just the frameworks.* Jessica’s summer program, Relationship Rhythms, and how it’s ushering in a more experimental vibe.* How Relationship Rhythms uses gamified accountability (yes, with prizes) to make relationship building fun* Why Jessica and Meg decided not to monetize the Substack—yet—and the honest convo about splitting podcast revenue* The challenges of co-hosting a podcast when your businesses are in different seasons (and speeds)* The messy beauty of relationship building: why some outreach grows instantly while others marinate for months* Meg’s AI trivia quiz: from radiologists to Reddit, from ChatGPT’s energy usage to recipes with random ground beef* Why learning how to learn will still be a critical skill, no matter about AI’s capabilitiesBloom’s TaxonomyJoin Relationship RhythmsSign up for the waitlist or join the program (opens June 9).Connect 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