Pioneers of AI

Tanay Kothari, founder and CEO of Whisperflow and early voice-assistant pioneer, discusses a post-keyboard future where speaking becomes the main way we interact with computers. He explores how voice reduces cognitive friction, boosts accessibility, improves emotional tone in messages, and powers smarter, context-aware assistants. Includes a live speed-and-accuracy demo pitting voice against fast typing.

Evan Ratliff, journalist and former founder who built HurumoAI with AI co-founders, describes testing a one-human startup. He explains why he chose particular agent personas and the odd behaviors that emerged. He recounts agents’ memory limits, managing interruptions, and the emotional ups and downs of working with bot colleagues.

Susan Bennett, the voice actor whose recordings became the original Siri, recalls quirky recording sessions and career impacts. Adam Cheyer, Siri co-founder and AI entrepreneur, traces the assistant's origin, agentic design, business model gaps, and a bold AR prediction. They discuss voice tech evolution, transactions versus knowing, and compensation for voice contributors.

Rafael Lesitsa, CEO at Gottman Inc., brings relationship science into AI tools for therapists. Will Wu, former Match Group CTO, builds AI features that improve photos, matches, and coaching on dating apps. They discuss AI-powered matchmaking, photo selection, coaching, therapist-assist tools, remote relationship measurement, and the rise of AI companions and their ethical trade-offs.

Joelle Pineau, AI researcher and Chief AI Officer at Cohere, discusses the OpenClaw surge and why agentic AI feels like a turning point. She explores safety and privacy risks of powerful local agents. She talks about open-source tradeoffs, building enterprise-ready agents, and how diverse, sovereign approaches shape the next wave of foundation models.

Jennifer Heil, Olympic gold-medal freestyle skier turned entrepreneur and founder of Revel, brings elite sports teamwork to women’s health. She discusses AI in sport analytics and judging, pivoting from athletics to building a Stanford-born startup, and Revel’s approach of scaling expert care with multimodal data and digital twins while protecting privacy.

Caroline Dell, co-founder and CEO of GoodWord, builds an AI networking co-pilot that helps professionals manage and activate relationships. She discusses human memory limits and how relationship intelligence augments them. Hear how GoodWord captures conversations, surfaces who to reconnect with, protects privacy, and offers five practical tips for non-icky networking.

Raffaello D’Andrea, a visionary engineer and the founder of Kiva Systems, dives into the fascinating world of robotics and drones. He shares the transformative impact of Kiva on warehouse efficiency and discusses the challenges of creating effective robots. Raffaello elaborates on Verity’s autonomous drones, which enhance inventory management and safety. He contrasts traditional vision systems with innovative AI models and highlights the potential of tailored robots for specific tasks. The conversation also touches on the future of humanoid robots and the importance of human connections in an AI-driven world.

Aaron Levie, co-founder and CEO of Box, shares insights on how his 20-year-old SaaS company is adapting to the AI revolution. He discusses the strategic shift towards agentic workflows and emphasizes the importance of cloud architecture. Levie argues that AI enhances enterprise value rather than eliminating SaaS, and he details innovative pricing models combining per-seat and consumption metrics. Security, governance, and the potential of AI to automate labor also take center stage, showcasing a future where AI augments human capabilities.

Dr. Shiv Rao is a cardiologist and the CEO of Abridge, a $5.3 billion AI company focused on reducing clinician burnout. In this engaging conversation, he discusses the public health crisis of doctor burnout caused by clerical burdens and staffing shortages. Rao explains how Abridge’s AI automates medical note-taking, enhancing the patient-clinician experience. He also touches on the challenges of multilingual support in healthcare and asserts that AI enables clinicians to focus more on human connection, ultimately improving care.