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

Framework-Free Zone: Life Updates, AI, and A Little Fun


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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 capabilities

Bloom’s Taxonomy

Join Relationship Rhythms

Sign up for the waitlist or join the program (opens June 9).

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Connect with Meg and Jessica

Meg Casebolt

Jessica 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
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Aggressively Human: Online Business in the Age of AI, Algorithms & AutomationsBy Meg Casebolt & Jessica Lackey

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