Newcomer Pod

Vinod Khosla, founder of Khosla Ventures and longtime Silicon Valley investor, shares bold ideas about AI, capitalism, and a future without survival jobs. He discusses AI multiplying resources, a guaranteed base lifestyle with preserved incentives, AI-driven healthcare and education, micro-entrepreneurship, and the geopolitical and policy stakes of rapid AI progress.

Katie Jacobs Stanton, former Twitter exec, Obama White House alum, and founder of Moxxie Ventures, joins to unpack Silicon Valley's silence and shifting power. She discusses changes at Twitter/X, why new social platforms have not replaced it, the AI cycle’s dot-com parallels, tech’s political reticence around ICE, and investing in health, energy, and AI tools.

Amanda Askell, a philosopher-turned AI researcher at Anthropic who helped shape Claude's character and values. They explore whether advanced models could be conscious and what moral weight that carries. Conversation covers how Claude learns time and rest, building a constitution to guide behavior, risks of misaligned power, and designing personas for predictable, safe AI.

Kara Swisher, veteran tech journalist and CNN contributor known for calling out Silicon Valley, joins to debate AI governance, tech narcissism, and the OpenAI board drama. She critiques longevity mania, provocation as persona, industry lobbying, and argues for democratic oversight over tech power. Short, sharp takes on Sam Altman, Elon Musk, and who should decide AI rules.

Jim Lanzone, an internet executive who revived Ask.com, Tinder, and now leads Yahoo. He explains Yahoo's AI search push, why they walked away from a $44B Microsoft sale, and how Scout and MyScout aim to reconnect users with publishers. He also discusses AI chatbots’ UI problems, publisher revenue concerns, and what 700 million users look like in 2026.

Han Wang, CEO of Mintlify — builder of AI-readable docs and self-updating knowledge for companies like Anthropic. Jesse Zang, CEO of Decagon — maker of AI agents for contact centers and voice/chat CX. They discuss doc-driven agents, a traffic-crashing OpenClaw crawl that revealed agent behavior, voice vs chat in customer experience, safety and memory for personalized conversations, and the infrastructure needs for scalable AI-driven support.

Matt Mahan, Mayor of San Jose and gubernatorial candidate focused on pragmatic city reforms. He breaks down California’s stalled high-speed rail as a sign of governance collapse. He discusses cutting homelessness through smart spending, using AI and performance management in city services, trade-offs in regulation and energy, and why competence-first politics matters for California’s future.

Shardul Shah, Partner at Index Ventures and early investor in Datadog and Wiz, shares stories of wiring seed money on conviction and a decade-long relationship with founders. He recounts why Google bought Wiz, how in-person chemistry shapes bets, why mid-size acquisitions often fail, and the people-first AI and cloud security opportunities he’s hunting now.

Barry McArdle, CEO and co-founder of Hex and former Palantir forward-deployed engineer, explains Palantir’s pragmatic data-integration playbook and why copying it fails. He contrasts field-driven engineering with product-scale approaches. He also explores how AI agents are reshaping data workflows, the future of business intelligence, and the trade-offs of model choices and enterprise pricing.

Rick Heitzmann, venture capitalist and FirstMark co-founder behind early bets like Airbnb and Pinterest. He talks about the AI investment boom, why massive private capital may push a fresh wave of IPOs, how data and AI infrastructure shape winners, and which megacaps might need public funding soon.