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

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

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

Dive into insights from a recent creator conference, where in-person connections outshine keynotes. Discover the challenges of AI content and explore the importance of raw, imperfect storytelling. Learn about practical AI strategies, including the 'use and refuse' approach, and the significance of maintaining relationships for long-term success. Get reminded that what seems like overnight success is often the result of years of effort and engineered luck. Perfect for creatives looking to thrive in an AI-driven world!

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

Michelle Warner, a business designer and strategist, emphasizes the essentiality of relationship marketing and solid fundamentals in today's maturing market. She explains why quick fixes don’t work anymore and shares insights on how many client issues stem from foundational misalignments rather than complex strategies. The conversation touches on the pitfalls of marketing arbitrage and how AI risks homogenizing messaging. Michelle encourages a return to basics, focusing on specificity and strong connections to thrive amidst growing competition.