Lars Doucet, author of "Land is a Big Deal" and a property tax expert, joins the conversation to unravel the complexities of property assessment. He explains how cities value properties and the political dynamics behind tax rates. The discussion covers the challenges of maintaining equity in assessments, especially with discrepancies between neighbors. Doucet shares insights on how technological tools like GIS are reshaping the landscape of property valuation and the potential benefits of predictive analytics in creating fair tax policies.

Patrick McKenzie dives into the intriguing balance between fraud prevention and customer experience. He examines how businesses and governments accept some level of fraud as a cost of doing business, using examples from payment systems and pandemic policies. The discussion highlights the ethical dilemmas in retail security and the complexities of navigating fraud in government benefit programs. Listeners will discover why reducing fraud to zero could stifle legitimate commerce and how different sectors calibrate their tolerance for fraud based on their unique challenges.

Max Chiswick, a former professional poker player and AI educator, discusses the fascinating intersection of poker and decision-making. He highlights how the online poker boom provided rich data sets for studying human choices. The conversation delves into how poker functions as a testing ground for AI while revealing the ethical dilemmas within both poker and AI development. Additionally, Max shares insights into the evolution of AI in the game, enhancing strategies and teaching through innovative online tools.

Byrne Hobart, author of "Boom: Bubbles and the End of Stagnation," dives into the interplay between economic bubbles and innovation. He discusses how irrational market enthusiasm, like the 1990s fiber optic boom, can lead to technological advancements that benefit society long-term. The conversation highlights historical examples, from Bell Labs to today's AI investments and energy infrastructure, illustrating how even painful market crashes can drive genuine progress. Byrne reflects on the cyclical nature of tech and finance, revealing hidden patterns of innovation amid speculation.

Erik Torenberg, founder of Turpentine and an expert in banking systems, joins the discussion on the complexities of money movement. They explore how banks use correspondent accounts and clearinghouses to facilitate transactions. The conversation shifts from the historical gold standard to the modern implications of stablecoins. Erik explains the different models of stablecoins, their potential for revolutionizing finance, and the challenges of regulation and compliance in the evolving financial landscape.

In this discussion, Ross Rheingans-Yoo, an expert in drug development, delves into the complexities of drug approval processes, revealing systemic inefficiencies and the evolving landscape of clinical trials. He reflects on historical events like the thalidomide crisis and how they shaped FDA policy, while also highlighting the impact of the AIDS epidemic and COVID-19 on accelerated approvals. Ross shares his innovative work in rescuing abandoned drugs and emphasizes the need for integrating technology into medicine to enhance patient care and streamline drug development.

Jetson Leder-Luis, an economist and fraud expert at Boston University, dives into the complexities of government program fraud. He exposes shocking healthcare fraud tactics, from hospice manipulations to ambulance service schemes. The conversation reveals how systemic flaws and poor policy designs enable these abuses. They discuss the economic fallout of fraudulent claims, the ROI on anti-fraud measures, and the ethics of vaccine distribution during COVID-19. Jetson advocates for innovative solutions to enhance regulatory frameworks and deter fraud.

Moses Kagan, co-founder of Adaptive Realty and an expert in real estate investment, shares rich insights into the intricate world of property management. He discusses the challenges landlords face, from financing to tenant dynamics, and highlights the profound impact of the Internet on capital raising. Kagan compares real estate markets across major cities, dives into the significance of cap rates, and explores how societal perceptions of landlords shape the rental landscape. His perspectives illuminate the complexities of rental dynamics and the immigrant contributions to the sector.

Erik Torenberg, an investor and media entrepreneur behind Turpentine, dives into the intricate dance between tech journalism and the tech industry. He discusses how storytelling in films like 'The Social Network' shapes perceptions of entrepreneurship. The conversation highlights the decline in quality journalism as talent shifts to tech roles, and how social media dynamics lead to groupthink among journalists. Torenberg urges a nuanced understanding of media's influence on tech, moving beyond simplistic narratives.

Jim McKenzie, a seasoned expert in commercial real estate development, joins his son Patrick for a compelling discussion. They reveal the intricacies of urban development, including the quirks of curb cuts and local politics. Jim shares captivating stories, like converting day-old bread stores into banks and the importance of historical telegrams in property law. The conversation also explores the balance between strategic location selection and customer patterns, providing a rare insight into the world of real estate and its hidden complexities.