Uncapped with Jack Altman

Kevin Hartz, serial entrepreneur (Eventbrite, Xoom) and investor; Bennett Siegel, early-stage investor and A* partner. They discuss how AI is reshaping startup founding and venture capital. They cover younger and researcher-led founders, the influx of big funds into seed, AI rollups and their pitfalls, and the promise of robotics and hardware in the coming AI boom.

Tarek Mansour, co-founder and CEO of Kalshi and former Goldman/Citadel trader, tells the story behind building a regulated prediction-market exchange. He discusses the long regulatory fight, the landmark lawsuit for approval, and how event-based markets change hedging, pricing of risk, and market incentives.

Max Mullen, co-founder of Instacart and active investor, reflects on building a contrarian grocery marketplace into a $10B business. He shares stories about early scrappiness, winning retailer partnerships like Trader Joe’s, navigating the Amazon–Whole Foods shock, and scaling complex marketplace operations. The conversation also touches on what makes standout consumer founders and his approach to investing.

Brad Lightcap, OpenAI’s COO who runs operations, partnerships, and the OpenAI Startup Fund. He discusses the shift from chatbots to action-taking agents. They cover how agents are built and deployed. Codex’s role in changing how code and work get done. Practical impacts for startups, incumbents, and broader economic changes.

Ron Conway, founder of SV Angel and legendary early investor behind Google, Airbnb and OpenAI, reflects on decades of deals and advocacy. He recounts shifting from semiconductors to AI. He talks about being an "all in" partner, brokering relationships that compound, stepping in at inflection points like Airbnb, and fighting for founders in boardrooms and Washington.

Max Junestrand, Founder and CEO of Legora, an AI-native legal software builder; Chetan, a venture investor with legal software experience. They tell Legora's origin, why building AI-native mattered, and how product and integrations beat generic models. They cover winning law firm pilots, rapid global scale from Stockholm, and the playbook for making legal workflows AI-first.

Jared Friedman, Managing Partner at Y Combinator and Scribd co‑founder; Harj Taggar, Managing Partner and former founder of Triplebyte; Garry Tan, YC CEO and investor. They talk about how AI is changing who can build, why execution still wins, rising product expectations, capital for AI startups, and which business models stay durable. Fast, wide‑ranging conversation about YC’s evolving focus and the future of founders.

Bret Taylor, serial entrepreneur and AI leader who co-created Google Maps and the Like button and now runs Sierra, talks about AI agents reshaping enterprise software. Short takes cover the so-called SaaS-pocalypse, how agents shift value from apps to data, outcomes-based pricing, technical limits in support, and why productized agents may outlast generic builders.

Peter Fenton, veteran VC known for Twitter and Elastic; Eric Vishria, investor behind Confluent and Amplitude; Chetan Puttagunta, early-stage specialist with MuleSoft and Elastic wins; Ev Randle, recent partner with prior Kleiner Perkins and Founders Fund experience. They discuss why staying small matters, equal-partnership dynamics, founder-first decision making, candid board relationships, and why that model suits fast-changing AI-era startups.

Vinod Khosla, a tech pioneer and founder of Khosla Ventures, and Keith Rabois, a former PayPal exec and current Khosla partner, dive into the evolving landscape of venture investing. They discuss what defines exceptional founders, the importance of direct communication, and the shift in investor ethos from previous generations. The pair also explore AI’s rapid growth potential, emphasizing the need for innovative team structures and strategies. They share insights on identifying hidden gems like Airbnb and OpenAI, while highlighting the transformative role of AI in startups.