On Monetizing Community with Patreon Cofounder Sam Yam

Anish Acharya is joined by Garry Tan, President and CEO of Y Combinator, for a conversation about how AI is rewriting the startup playbook, why founders should be more ambitious than ever, and what two decades of Silicon Valley booms, busts, and missed opportunities have taught Garry about building what's next. Garry reflects on turning down an early opportunity to join Palantir, why chasing what's "hot" is often the wrong strategy, and why the best ideas tend to begin with people pursuing strange, earnest obsessions outside the mainstream. They also explore how AI changes the economics of company building, why traditional SaaS may be losing its advantage, and how tiny teams equipped with hundreds of agents can build businesses at a scale that once required entire organizations. The conversation goes deeper into agentic companies, taste and agency, why "a markdown file is an employee," and how AI could remove layers of bureaucracy that have historically limited organizations. Garry and Anish also discuss the future of consumer AI, the coming "harness wars," why AI adoption may take longer than Silicon Valley expects, and what the next generation of founders can build with intelligence that was unimaginable just a few years ago.

a16z's Joel De La Garza is joined by Emilio Escobar, Chief Information Security Officer at Datadog, to discuss what it takes to secure a company where nearly every employee is using AI and more than 4,000 engineers are working with coding agents. Rather than trying to block new tools, Emilio explains why Datadog chose to embrace AI early and build the security infrastructure needed to use it safely. They unpack how AI changes traditional assumptions around data permissions, credentials, developer access, and software supply chains. Emilio shares how Datadog uses role-based MCP servers and ephemeral credentials, as well as an AI "judge" built by his security team to evaluate the intent behind code and agent skills before they enter the environment. They also discuss why security teams can't afford to wait for commercial solutions to every new AI threat, how the relationship between developers and security teams needs to change, and why Emilio is less concerned about an AI "escaping" than he is about the sheer volume of vulnerabilities AI could uncover.

Angela Strange and Gabriel Vasquez are joined by Alejandro Maza Ayala, Chief Product & AI Officer at Kavak, to unpack how the Latin American used-car marketplace rebuilt itself around AI agents, with 96% of customer interactions and 95% of transactions now handled by agents. Alejandro explains why Kavak decided that simply giving employees AI tools wasn't enough, and instead redesigned the company's systems, teams, and customer experience around agents. They discuss why Kavak spends as much engineering effort on evals as it does building agents, how its AI sellers outperform its human teams, and an experiment where an AI "CEO" increased profits in one city by 50% in its first month. The conversation also explores what happens to organizational structure when agents do most of the work, why Kavak trains everyone from executives to mechanics to build with AI, and Alejandro's argument that companies looking for incremental AI adoption may be missing the larger opportunity: redesigning the organization itself.

Joel De La Garza is joined by Dylan Ayrey, co-founder and CEO of Truffle Security, and Feross Aboukhadijeh, founder and CEO of Socket, to discuss one of the biggest shifts happening in cybersecurity: AI models are no longer just finding vulnerabilities—they're exploiting them. As frontier models become increasingly capable of hacking, software security, supply chain attacks, and cyber defense are entering a fundamentally new era. The conversation explores AI-powered hacking, software supply chain attacks, leaked credentials, zero-day vulnerabilities, package manager security, and why the path of least resistance for increasingly autonomous AI systems may also be the most dangerous. They also discuss what enterprises, developers, and the open-source ecosystem need to do to adapt as the gap between vulnerability discovery and exploitation continues to shrink.

Elena Burger and Matt Bornstein are joined by Simon Mo, co-founder and CEO of Inferact, the open-source inference engine powering many of today's most advanced AI applications. Together, they explore how open-source AI evolved from a research project into critical infrastructure, why inference has become one of the most important layers of the AI stack, and what it takes to bring frontier intelligence to developers around the world. The conversation covers vLLM's origins, the rise of open-weight models, why companies increasingly want control over their AI infrastructure, and how open-source inference enables the next generation of AI applications. They also discuss model licensing, the economics of open-weight AI, Kimi K3, distillation, AI infrastructure, and why Simon believes the gap between open and closed models is rapidly disappearing.