20VC with Harry Stebbings

Dr. Andrew Ng joins 20VC for a deep, candid conversation on the state of AI, the bottlenecks holding the industry back, and how LLMs are becoming tools of enormous geopolitical power. In this episode, Andrew breaks down the constraints around compute, data, and infrastructure, and why the *application layer* is where the most exciting breakthroughs are emerging. The discussion dives into how LLMs might be used as geopolitical weapons, what governments get right and wrong about AI, and why global competition is accelerating innovation. Andrew shares contrarian views on talent compensation, defensibility in an AI-native world, and whether margins still matter when software is built on top of trillion-parameter models. The episode also explores the economic shifts ahead — from workforce evolution to whether AI can drive Masa Son’s projected 5% global GDP uplift. Recorded for the 20VC Podcast, this conversation captures the intersection of technology, economics, and global power — and how AI is reshaping every dimension of society.

Sequoia Capital’s leadership transition, a surprising $100M raise for Gamma at a $2B valuation, and the question everyone in tech is debating today — does defensibility still matter when AI makes copying effortless? In this episode, Harry Stebbings sits down with iconic SaaS investors Jason Lemkin and Rory O’Driscoll to break down the biggest stories shaping the venture world right now. They dive into Sequoia’s evolving strategy and what its leadership change signals for the industry, Michael Burry’s unexpected short positions on Nvidia and Palantir, and whether today’s AI-driven markets reward speed more than moats. The conversation explores the shifting meaning of product defensibility, why some funds may need to rethink concentration vs. diversification, and how founders can run more effective fundraising processes in a volatile market. Lemkin and O’Driscoll also analyze recent earnings surprises — from Datadog’s surge to Duolingo’s drop — drawing lessons on performance, expectations, and founder storytelling. Recorded for 20VC, this episode is a fast, honest look at how venture, SaaS, and AI markets are being rewritten in real time.

Ev Randle, General Partner at Benchmark, joins Harry Stebbings on 20VC to unpack how AI is reshaping the economics of venture capital. In this conversation, Ev explains why traditional margin metrics matter less in the age of AI, why mega funds are unlikely to generate strong returns going forward, and how Benchmark continues to identify outlier founders in a rapidly changing landscape. He shares lessons from investing alongside icons like Peter Thiel, Mary Meeker, and Mamoon Hamid, and discusses how Benchmark’s approach to founder partnerships differs from other top-tier firms. The discussion also explores OpenAI’s trillion-dollar potential, the threat AI labs pose to app companies, and why gross dollars per customer are becoming a more meaningful measure than margins. Recorded for 20VC, this episode dives deep into the future of venture capital, AI investing, and what it really takes to stay exceptional in a world flooded with capital and competition.

In this episode of 20VC, host Harry Stebbings is joined by legendary investors Jason Lemkin and Rory O’Driscoll to unpack a packed week in tech and venture capital. They start with Navan’s IPO—who the real winners and losers are, and what caused the stock to crater 20% on debut. Then they dive into Harvey’s $150M fundraise at an $8B valuation, exploring what this means for AI enterprise software and how such valuations are being justified in today’s market. The conversation then shifts to a broader look at Big Tech, with a spirited debate on why Google remains a buy while Amazon may be heading for a rough patch. They also touch on Sam Altman’s recent exchange with Brad Gerstner, Meta’s 10% drop, and the critical importance of AI acceleration for startups in 2025. Finally, the trio discuss why now might be the best time for Series A founders but the toughest environment for seed-stage entrepreneurs. An unfiltered, insightful discussion capturing the pulse of today’s venture ecosystem and the future of AI-driven markets.

Joelle Pineau, Chief Scientist at Cohere and Professor at McGill University, joins Harry Stebbings on 20VC to explore the evolving frontiers of AI research and deployment. In this conversation, Joelle reflects on her journey from Meta to Cohere, what she learned leading Meta AI’s Montreal Lab, and how those lessons shape her philosophy on scaling laws and practical AI systems today. They dive deep into topics including reinforcement learning breakthroughs, data efficiency, capital allocation in AI, enterprise adoption, and the rising cost of high-quality data. Joelle also discusses the promise and pitfalls of synthetic data, model degradation, and why she believes scaling laws will continue to define AI progress. The discussion touches on security concerns with AI agents, how enterprises can adopt AI responsibly, and what the next generation of researchers should focus on. Recorded for The Twenty Minute VC, this episode offers a rare window into how one of AI’s leading minds sees the balance between science, engineering, and responsibility in building the future of intelligent systems.

Andreessen Horowitz (a16z) has raised $10 billion in new funds, marking one of the largest fundraising rounds in venture capital history. In this episode of 20VC, host Harry Stebbings is joined by Jason Lemkin, Founder of SaaStr, and Rory O’Driscoll, General Partner at Scale Venture Partners, to discuss what this means for the venture ecosystem and where capital allocation is headed next. The conversation dives into the details of a16z’s latest raise, the strategic implications for early- and late-stage founders, and how the venture landscape is evolving amid shifts in AI, infrastructure, and global capital flows. They also explore Mercor’s $350M raise at a $10B valuation—how the company scaled so rapidly, what differentiates it in the AI talent marketplace, and what this signals for startups blending automation, freelancing, and AI-driven labor models. Later in the episode, the guests analyze patterns behind 'spray and pray' investing, the role of option checks in venture capital, and why IRR might be an overrated metric in evaluating fund performance. This conversation captures the pulse of modern venture capital—from mega-funds to micro-checks—and how top investors think about risk, scale, and the next decade of innovation.

David Cahn is a Partner at Sequoia Capital and one of the world’s leading AI investors. At Sequoia David has led investments in Clay, Juicebox, Sesame, Kela, Stark, etc.. Before Sequoia, David was a General Partner at Coatue where he led investments in Notion and Hugging Face.

20VC’s Harry Stebbings hosts Jason Lemkin (SaaStr) & Rory O’Driscoll (Scale VP) on Vertical SaaS, AI investing, Revolut $75B, OpenAI cloud play & TAM myth.