The Cave Project™️

A podcast exploring the tensions of tech, culture, and life as they collide.

A detailed drawing of prisoners with chains on their necks kneeling in a cave, watching a puppet show with figures, animals, and mythological characters projected on the cave wall, inspired by Plato's Allegory of the Cave.

Plato’s Allegory of the Cave is a story about people who have spent their entire lives chained inside a cave, able to see only shadows projected on the wall in front of them. Because the shadows are all they know, they mistake them for reality.

When one prisoner escapes and sees the outside world, he realizes the shadows were only illusions and that a fuller, brighter truth exists beyond the cave. But when he returns to tell the others, they reject him because the truth is uncomfortable and unfamiliar.

The allegory is about knowledge, perception, education, and the difficulty of helping people see beyond the limits of what they have always believed.

Our Story

The Cave Project™️ is a podcast and digital space created by Jenny and Greg Swan to explore the weird, funny, uncomfortable, and deeply human ways technology shapes our culture, work, families, relationships, identities, and everyday lives.

Inspired by Plato’s Allegory of the Cave, we’re interested in the shadows on the wall: the things we accept as reality because the platforms, algorithms, dashboards, and devices told us so.

We talk about marketers chasing innovation while forgetting people, parents raising kids in a pixelated world, the psychological circus of being Extremely Online, the emotional whiplash of going viral, and what it means to connect, grieve, grow, and belong in digital-first spaces.

The Cave Project™️ is for anyone trying to make sense of modern life without pretending the smart fridge, the TikTok algorithm, or the group chat has all the answers.

This project is an extension of the dinner table conversations we've been having together for decades. And we're inviting you to the discussion, because we want to make this table bigger. And better. And more complete.

Thanks for being here.

Close-up of a woman with long brown hair, wearing glasses and a red shirt, smiling with eyes closed, sitting outdoors with a brick wall in the background.

Jenny Swan

With one bachelor’s degree in psychology and another in accounting, Jenny has a unique perspective on digital culture. She brings curiosity, humor, heart, and a healthy dose of skepticism to every conversation—from parenting in the influencer age to the ethics of AI. 

From her work as an accountant in the business world to volunteering on mental health advisory boards and civic groups, AND as a parent of three kids, Jenny keeps things real, relatable, and just the right amount of irreverent.

Jenny Swan is always keeping an eye toward keeping humans and empathy top of mind when approaching emerging technology. 

A man with glasses, wearing a navy cap, a white shirt with dark speckles, standing against a red brick wall, smiling and gesturing with his right hand.

Greg Swan

Greg is a senior marketing leader who has been hanging out on the tech-forward side of the communication and marketing spaces for a long time, doing things like sending beef jerky to space, sending faxes from Google Glass, and creating games where you have to hold down the right arrow on your keyboard for 4 hours to earn a free fast food sandwich.

He likes to take tech and push the limits of “what’s next” at work and play. And that shows up in the home life, too — whether that’s wiring up the entire house with automations, being the first to buy the latest tech gadget, or taking all three kids on a family field trip to see the robots at the local Amazon warehouse.

Greg Swan is always thinking about “what’s next,” while being open to considering change isn’t always great for the humans involved.

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