Wickedly Smart and Woefully Stupid Episode 5 - Teddy Roosevelt's Legacy

Wickedly Smart and Woefully Stupid Episode 9 - Mike Long - The Evolution of Democracy

What Does Democracy Actually Feel Like From the Inside? Most conversations about democracy right now feel like arguments — volleys of talking points launched from entrenched positions, designed to win rather than illuminate. This episode is something different. This week, Wendy sits down with her partner, Mike Long, a lifelong student of history and human psychology, and, together with Harvey, the three of them do something that feels almost radical in 2026: they just... think out loud together. About where we came from, what we might be losing, and whether the thing we call democracy has ever actually delivered on its promise — and for whom. Mike brings 2,000 years of context to a moment that desperately needs it. Harvey brings the psychological reckoning. Wendy brings the land, the women, the wolves, and the uncomfortable questions that refuse to stay politely in the margins. What emerges isn’t a debate or a lecture — it’s the kind of conversation that used to happen in forums and on front porches and at dinner tables before we all retreated into our separate information ecosystems. There’s grief in this episode, and there’s also genuine hope — not the performative kind, but the kind that comes from actually knowing history well enough to recognize that we’ve pulled ourselves back from the brink before. Come think with us. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wickedlysmartwoefullystupid.substack.com [https://wickedlysmartwoefullystupid.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Wickedly Smart and Woefully Stupid Episode 8 - Gary Salyer - Attachment Styles

What if the way you love was shaped before you could even speak — and what if that same pattern is running our institutions, our politics, our planet? In this episode, Wendy and Harvey sit down with transformational relationship mentor Dr. Gary Salyer to explore the hidden architecture of attachment — the early patterns that wire us for connection, conflict, or shutdown long before we have words for any of it. But this conversation doesn't stop at the personal. Anxious clinging, avoidant walls, the compulsive need to dominate or disappear — these aren't just relationship dynamics. They're the operating system behind our most intractable social fractures. What does a society organized around insecure attachment actually look like? (Spoiler: look around.) Dr. Salyer makes the case that interdependence — real, secure, practiced interdependence — isn't just a relationship goal. It might be the missing variable in every system we're trying to fix. Wickedly Smart: The neuroscience and attachment theory behind why we love, fight, and organize the way we do. Woefully Stupid: That we keep trying to solve collective problems without ever examining the relational wiring underneath them. The personal isn't just political. It's ecological, institutional, and civilizational. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wickedlysmartwoefullystupid.substack.com [https://wickedlysmartwoefullystupid.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Wickedly Smart and Woefully Stupid Episode 7 - Nature As Board Member

What if nature had a seat at the table — not as a resource to be managed, but as a voice to be heard? In this episode, Wendy and Harvey dig into Alexandra Pimor's Nature on Board movement — a radical, quietly spreading idea that nature deserves representation in the very boardrooms and decision-making bodies shaping its future. From Ecuador writing the rights of Pachamama into its constitution, to New Zealand granting legal personhood to a forest and a river, to Patagonia transferring its ownership entirely to the earth — something is shifting. The question is whether it's shifting fast enough, and whether it can reach the places that matter most: corporate boards, legislative chambers, and the governance structures that set the rules everyone else follows. Wendy knows what it's like to stand inside a real ecosystem and speak for it. Harvey knows what it costs when no one does. Together, they ask the uncomfortable question: how many catastrophically expensive, planet-damaging mistakes could we have avoided if nature had simply had someone in the room? Wickedly Smart: Nature-conscious governance — from legal personhood for rivers to nature proxies on corporate boards. Woefully Stupid: That we gave corporations personhood centuries ago and are only now thinking to extend the same courtesy to the living world. The FY2026 EPA budget is $8.8B. Cumulatively (1970-2025), it's estimated budget is $350.6B. Imagine what else we could have achieved if we'd just had Nature at the center of our institutions. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wickedlysmartwoefullystupid.substack.com [https://wickedlysmartwoefullystupid.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Wickedly Smart and Woefully Stupid Episode 6 - Erin Dayl - Regenerative Business

The soil beneath your feet is a living system. So why do we treat it like dirt? In this episode, Wendy and Harvey sit down with sustainability pioneer and transdisciplinary systems thinker Erin Dayl — a woman who has spent 25 years at the intersection of clean energy, regenerative agriculture, social justice, and the kind of organizational thinking that actually moves things forward. From breaking a 50-year energy contract in rural New Mexico, to building tribal energy sovereignty, to designing what a truly regenerative company might look like from the ground up — Erin is someone who doesn’t just study transformation. She architects it. The conversation ranges wide: why solar is cheap but political, what precision agriculture can and can’t fix, how a farm worker should be able to talk to a CFO without fear, and what it actually means to scale something without losing its soul. Spoiler: it looks a lot less like owning more and a lot more like sharing well. Wickedly Smart: Regenerative agriculture as a systems solution — for soil health, water savings, food nutrition, and community resilience. Woefully Stupid: That we keep applying industrial-scale thinking to problems that require relational, place-based ones. We are in a Buckminster Fuller moment, Erin says. People have found their line in the sand — and they’re building the world they want on the other side of it. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wickedlysmartwoefullystupid.substack.com [https://wickedlysmartwoefullystupid.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Wickedly Smart and Woefully Stupid Episode 5 - Teddy Roosevelt's Legacy

What would Teddy Roosevelt think of today's world — and what would you do if you were president? Wendy and Harvey kick off with a powerful (if possibly misappropriated) Roosevelt quote about leaving the land better for future generations, then trace the arc from his bold conservation legacy to today's dismantling of public lands and the silencing of climate from mainstream discourse. Along the way, they wrestle with “conventional wisdom,” the politics of natural resources, $15 bags of grapes, and whether a Thomas Paine-style catalytic moment could still shift the cultural narrative. They end up somewhere unexpected: a shared presidential platform, a tag-team ticket, and a genuine question — what would it take to make stewardship, equity, and connection to the land the default values of society again? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wickedlysmartwoefullystupid.substack.com [https://wickedlysmartwoefullystupid.substack.com?utm_medium=podcast&utm_campaign=CTA_1]