While AI still can’t fold your laundry, it can help you build a business that runs smarter—and a life that runs smoother. In this episode, Jessica and Meg talk with Mary Williams, the librarian-turned-tech director behind Sensible Woo and the new Sasquatch Media Grounds studio in Portland. From haunted recording spaces and tarot cards to spreadsheets and AI bots, Mary shows what it looks like to blend intuition with technology.

She shares how she built her “AI team”—including Remy, the snarky Gen Z assistant who filters her inbox and protects her calendar—and why she treats her chatbots like departments inside her business. They talk about how AI can help reduce emotional labor, from grocery budgets to health tracking, and what it means to build systems that keep the human at the center.

This conversation is filled with practical ways to make AI feel less robotic (and maybe a little more like a helpful intern who swears), while lightening your load with technology that actually serves you.

* Mary’s path from librarian and tarot reader to tech director and business coach

* How she organizes AI “staff” into departments—finance, operations, marketing, and more

* The surprising power of giving your bots names and personalities

* Why AI reveals more about your delegation habits than you think

* How to build an AI “board of advisors” with personas like Mark Cuban or Reese Witherspoon

* Emotional patterns people bring to technology (and what that says about leadership)

* Creative personal uses for AI—from meal-planning and purchasing decisions to health tracking

“I would argue if you had an intern, if you had a Gen Z Remy with you, you’d still fact check them because they’re young, they’re learning. I need to make sure that everything’s right. And in that sense, you’re still doing the same functions, you’re not doing less, you’re really not doing more. It’s just moving along faster.” - Mary

About our Guest

Mary Williams: Sensible Woo | Sasquatch Media Grounds

You, Me ChatGPT Workshop

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Meg Casebolt

Jessica Lackey

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