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

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.

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

Maggie Patterson, author of Staying Solo and creator of BS Free Business, discusses her journey from agency owner to solo business advocate. She challenges the scaling mentality in the online business world, emphasizing sustainable practices and ethical pricing. Maggie shares insights on self-publishing, the messy reality of writing a book, and the joy of using human-centered marketing tactics. Her refreshing perspective encourages solopreneurs to embrace their individuality while navigating the pressures of the business landscape.