What happens when every business book tells you what to think—but never explains what or how to do it?

In this episode, Meg interviews Jessica about her new book, Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works. The conversation traces how the book came to life—from frustration with hollow business advice to the creation of a grounded, systems-based framework for experts who want to stay small, sustainable, and sovereign.

Jessica shares how she read her way through the entire business section—books that were motivational but hollow, all premise and no practice. Some were thinly veiled sales funnels; others were memoirs pretending to be manuals. None answered the questions solo business owners actually ask: How do I make better decisions? What kind of business am I running? What’s enough? And how do I make this sustainable?

They explore what’s missing from most business books, the trap of “CEO-energy” culture, and the myth that scaling is the only path forward. Jessica shares how years of client work, research, and teaching evolved into a practical field guide for soloists who want to build differently—without gambling their time or integrity.

Get the details behind Leaving the Casino!

* Why Jessica wrote Leaving the Casino after realizing most advice ignores context

* How the online business world sells tactics that don’t fit most experts

* Why many books are either memoirs or funnels to a paid program

* How Jessica went from consulting to creating and publishing the book

* The limits of frameworks like Profit First, Traction, and Essentialism

* The risks of outsourcing sales, marketing, and finance too early

* Responsibility, enoughness, and right-sized growth as operating principles

* How privilege and life circumstances affect what “success” looks like

* Why the book blends manifesto and textbook—both call-to-arms and manual

* Jessica’s hope that it becomes a long-term reference for expert entrepreneurs

Resources

Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works

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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 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 conversations

About our Guest

Shivani Mehta Bhatia

Monthly Conflict Clinic

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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 chapter

About our Guest

Megan Dowd

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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 time

Want 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 Lab

Content Love Lab

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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.” - Prerna

About our Guest

Content Bistro

Skeptic Buyer Bot

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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 solo

About our Guest

Erika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-Making

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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 control

About our Guest

Erika Tebbens | Book — You've Got This: A Counterintuitive Guide to Powerful Inevitable Change-Making

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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-publishing

About our Guest

Dr. Matthew Jones

The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup Success

Mentioned Resources

John and Julie Gottman

Imago Therapy

Noam Wasserman’s The Founder’s Dilemma

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Instead of the polished Meta ads and the seamless email sequences, get the real behind the scenes of our businesses over the summer: the good, the hard, and the realities of summers in our businesses.

* Why Jessica is running Meta ads and why she feels she’s doing it wrong

* How Meg has leaned into retainer work this summer and it’s been exactly what she needed

* The soothing activities of repeatable, even some kind of boring work

* Confronting business model realities (“it can be easy to sell or easy to deliver but it cannot be both”)

* Meg’s fall challenge: Findable Everywhere (because even though how we search might be changing, the fundamentals of showing up in AI and SEO are even more critical).

* Jessica’s summer program debrief, and how it went from 9 prompts to 6 videos, 30+ prompts, and 10 detailed resources.

* Jessica’s fall, including the Define Your Foundations business building cohort and the book launch.

Join us this Fall:

* Findable Everywhere: A 5-Day Challenge to Show Up on Google, ChatGPT, And Wherever Your Dream Clients are Searching

* Define Your Foundations: Escape the “Tactics Trap” and start building real business foundations.

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“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.” - Meg

We 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.” - Samantha

About our Guest

Samantha Pollack - and join the “Get the Mixtape” newsletter

The Craft small group writing workshop

Substack: https://substack.com/@indiecopystudio

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