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Sarah Haider, a former activist and podcaster, shares her eye-opening journey after trying ayahuasca. She reveals how this powerful psychedelic shifted her perspective on life and her podcasting career, leading her to reevaluate her engagement with online culture. The conversation also explores her transition from a Muslim upbringing to activism, the allure and risks of ayahuasca, and the emotional toll of societal outrage. Haider emphasizes the importance of meaningful conversations over sensationalism and the need for clarity in a chaotic digital world.

Alastair Gordon, a cultural historian and author of "Naked Airport," dives into the peculiar phenomenon of airport luggage stores. He explores the strange trend of shopping for luggage in places where travelers already have bags, revealing the cultural significance of these retail spaces. Gordon shares insights on the evolution of air travel and the transformation of airports into shopping destinations. He also discusses the quirky demographics of luggage buyers and the intriguing history of unclaimed baggage, uncovering surprising stories behind lost items.

Ryan Broderick, author of the Garbage Day newsletter and host of the Panic World podcast, dives into the curious world of jawmaxxing. He explores how an unconventional dental theory gained traction among young men online. The discussion touches on the influence of classic TV shows on masculinity and unpacks the rise of jaw-maxxing and mewing as social media trends. Ryan highlights the clash between self-improvement aspirations and the realities faced by today's youth navigating identity within fragmented internet culture.

A human caught in a bureaucratic nightmare navigates the chaos between the DMV and Carvana. They face absurd challenges while trying to purchase a car online during a major life change. The tale unfolds with a mix of personal stories, highlighting the emotional struggles of dealing with customer service and missing documents. Insights into Carvana’s ambitious plans to reshape the used car market are shared, alongside their regulatory battles and the inefficiencies of the DMV system. Amid the frustration, a slice of joy emerges with a wedding license story.

Loren J. Samons, a Greek history professor, delves into the fascinating rise and fall of Athenian democracy. He explores its complex structure and societal impacts, highlighting the paradox of Socrates' trial, where democracy both spared and condemned him. The conversation addresses how public service payments contributed to democratic decline and reflects on Thucydides' insights about human nature. Samons draws parallels to modern governance, prompting listeners to consider the lessons history offers for democracy's future.

Rev. angel Kyodo williams, an ordained Zen priest and author of Radical Dharma, shares insights on navigating anxiety through meditation. She discusses the challenges of finding stillness in a chaotic urban life, emphasizing the transformative power of quiet reflection. Rev. angel explores the emotional journey during meditation retreats, unveiling personal growth and empowerment. She champions the significance of embracing both joy and pain to cultivate a fulfilling existence, closing with an invitation to a transformative meditation event.

Tech reporter Casey Newton from Platformer dives into the intriguing evolution of OpenAI's leadership and its growing influence in the AI landscape. He discusses the recent reshuffling of the board and how Sam Altman has consolidated power, sparking debates about ethical concerns and organizational culture. The conversation touches on the alarming turnover rate at OpenAI, the implications of rapid technological advancements, and the societal fears surrounding AI's impact on jobs and democracy. It's a captivating look at the crossroads of innovation and responsibility.

Jesse Eisinger, a renowned investigative journalist at ProPublica, and Alison Schrager, a senior fellow at the Manhattan Institute, delve into the world of billionaire taxation. They reveal surprising strategies like 'buy, borrow, die' that let billionaires like Jeff Bezos pay less tax than average Americans. The conversation explores the ethical dilemmas faced by whistleblowers who expose such discrepancies and the ongoing debate over tax equity. Expect insights into proposed reforms and the challenging balance between wealth and responsibility in today's economy.

Jesse Eisinger, a Pulitzer Prize-winning journalist from ProPublica, and Molly Mitchell Moore, a history professor at Washington and Lee University, dive into the shocking revelation that billionaires can pay zero dollars in federal taxes. They discuss the complexities of tax reporting for the wealthy and how financial journalism plays a crucial role in exposing these issues. The conversation also explores the historical evolution of income tax in America, highlighting past struggles against wealth inequality and the challenges of reforming the current tax system.

Anna Sale, the host of "Death, Sex, and Money," dives deep into life’s intimate struggles alongside Jim Harris, an adventure athlete who overcame a spinal injury. They discuss the power of open dialogue about taboo subjects like death and sexuality. Jim shares his incredible journey of recovery through psychedelics and the healing effects of nature and music. They explore emotional challenges during rehabilitation, the transformative potential of community, and how experiences of loss can shape identity and self-discovery.