What happens when AI collides with salesmanship, streaming-era sports, and healthcare? In this episode, Erik Torenberg is joined by Mark Cuban, entrepreneur, Dallas Mavericks co-owner, and founder of Cost Plus Drugs. Topics include fiery group chats and how dissent sharpens thinking, the sales playbook of modern politics, and concrete fixes for U.S. healthcare like ending PBM opacity, publishing real prices, and government-backed patient financing. Mark also explains how AI is pushing media from “social” to algorithmic, why he expects millions of models, and why ESOPs are an underrated wealth engine. He shares what he’d build today and weighs in on NBA economics under the new collective bargaining agreement. Timecodes: 00:00 Introduction 01:00 Independent Thinking & Political Identity 03:18 The Impact of AI on Media & Society 06:26 The Future of Social Platforms 08:50 Lessons from the SEC & Privacy 09:20 Political Messaging: Democrats vs. Republicans 12:30 Economic Inequality & Employee Ownership 14:17 Populism, Policy, and Political Strategy 16:00 The Role of Technology in Government 17:03 AI’s Impact on Education 18:49 AI and the Future of Healthcare 21:55 Insurance, PBMs, and Healthcare Reform 29:46 Entrepreneurship & AI-Native Careers 33:54 Business Success, Investing, and the NBA 40:05 Luka Trade, Cooper Flagg, and the New CBA 42:40 Max Deals, Second Stars, and Apron Math 51:05 Family Time and an Unconventional Investing Style 56:24 Making AI Popular and Closing Notes Resources: Find Mark on X: https://x.com/mcuban Stay Updated: Let us know what you think: https://ratethispodcast.com/a16z Find a16z on Twitter: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Subscribe on your favorite podcast app: https://a16z.simplecast.com/ Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.