10+ hours of podcasts, in 5 minutes.
Every full 20VC with Harry Stebbings episode we cover, summarized with verbatim, timestamped quotes: 51 episodes and 243 articles since April 2026. Hosted by Harry Stebbings. Part of our Business coverage. New summaries every Sunday.
Microsoft CEO Satya Nadella joins Harry Stebbings to discuss why organizations must assume AI models are compromised and how to design an engineered zero-trust…
Naveen Rao, Founder and CEO of Unconventional AI and former co-founder of MosaicML and Nervana Systems, discusses why power constraints and the end of physical…
Bessemer Partner Sameer Dholakia discusses the firm's $5.75 billion fundraise and why artificial intelligence represents a larger supercycle than the internet…
Harry Stebbings, Jason Lemkin, and Rory O'Driscoll debate the structural shifts reshaping venture capital, including why mega-funds ignore profitable non-AI Sa…
LangChain co-founder and CEO Harrison Chase joins Harry Stebbings to unpack the engineering challenges of building reliable AI agents and managing enterprise a…
Harry Stebbings, Jason Lemkin, and Rory O'Driscoll debate the legal feud between Valar Atomics and Day One Ventures over pro rata rights, analyze NVIDIA's rumo…
Atlassian co-founder and CEO Mike Cannon-Brookes joins Harry Stebbings to analyze how AI agents are transforming enterprise software, arguing that headless arc…
Venky Ganesan, Partner at Menlo Ventures, joins Harry Stebbings to dissect the evolving venture landscape in the age of artificial intelligence. They discuss f…
Harry Stebbings, Dev Ittycheria, Jason Lemkin, and Rory O'Driscoll analyze OpenAI's reported $70 billion run rate and massive quarter-over-quarter acceleration…
Max Freeman, SVP of Sales at Ramp, joins Harry Stebbings to dissect the operational blueprint behind scaling one of tech's fastest-growing sales machines. Free…
Higgsfield founder and CEO Alex Mashrabov joins Harry Stebbings to discuss reaching $1 billion in annualized run-rate revenue in just 18 months. Mashrabov shar…
Chase Lochmiller, Co-founder and CEO of Crusoe, discusses the infrastructure, energy, and hardware economics powering the AI revolution following their $3.9 bi…
Harry Stebbings, Jack Altman, Jason Lemkin, and Rory O'Driscoll analyze major AI market moves including Anthropic's leaked S-1 draft, Instinct's $1 billion Ser…
Parallel Co-Founder and CEO Parag Agrawal joins Harry Stebbings to discuss building web search infrastructure purpose-built for AI agents rather than humans. H…
Matteo Franceschetti, co-founder and CEO of Eight Sleep, discusses how Eight Sleep leverages AI agents to replace traditional engineering and marketing teams w…
Town co-founder and CEO Jean-Denis Grèze joins Harry Stebbings to discuss the emergence of agentic AI assistants and the battle between startups and Big Tech.…
Harry Stebbings, Jason Lemkin, and Rory O'Driscoll analyze the accelerating AI landscape, debating whether Jensen Huang is right that AGI has arrived with Open…
Cliff Weitzman, founder and CEO of Speechify, joins Harry Stebbings to discuss the financial and operational reality of buying tens of millions of dollars in N…
ClickHouse Co-Founder and CEO Aaron Katz discusses scaling real-time analytics infrastructure to over $350 million in ARR and the technical demands created by…
Harry Stebbings, Jason Lemkin, and Rory O'Driscoll break down NVIDIA's monster quarter and acquisition of Hugging Face, analyze OpenAI's decision to cut off Cu…
Sequoia Capital partner Julien Bek breaks down how Sequoia operates behind closed doors, including its async Investment Committee process, hunter mentality, an…
Andrew Macdonald, Uber's President and COO, discusses his 14+ years at the company, including the early days of autonomous vehicle investment and the tumultuou…
Insight Partners co-founder Jerry Murdock analyzes the structural vulnerabilities in the current AI boom, warning that debt-fueled hyperscaler expansion and fr…
In this episode, Matt Swulinski, a growth master from Superhuman, Whisperflow, and Victor.com, shares his philosophy of applying the e-commerce playbook to Saa…
This episode delved into major tech shifts, beginning with Canva's growth slowdown due to soaring AI costs and a broad discussion on AI's impact on existing so…
Harry Stebbings and David Frankel delve into the complexities of seed-stage venture capital, discussing the current AI boom's impact, the challenges of fund sc…
This episode features Harry Stebbings, Rory O'Driscoll, Jason Lemkin, and guest Nikesh Arora, CEO of Palo Alto Networks. They discuss the implications of AirTa…
Anastasios, CEO of Arena, discusses the rapidly evolving AI landscape, from the commoditization of models driven by open-source advancements, particularly from…
Jun Song Park, co-founder and CEO of Simily, discusses how their company creates a foundation model of human behavior through simulations. He explains Simily's…
In this episode, Oswald Nitski, CPO at Mercor, discusses the complex relationship between open-source models and data providers, arguing that open AI raises th…
Fred Turner, CEO of Curative, shares the incredible journey of scaling a COVID testing business to $5 billion in revenue before pivoting to health insurance, n…
Harry Stebbings interviews Arind, founder of Glean, discussing the competitive dynamics of the AI landscape. They cover the shift towards open-source models in…
Harry Stebbings speaks with Mike Mignano, a new General Partner at USV, about the evolving landscape of AI. They discuss USV's thesis-driven investment approac…
This episode delves into the evolving landscape of AI, examining the US government's increasing involvement through regulation and potential ownership stakes i…
Harry Stebbings interviews Clay Pavore, co-founder of Sierra, delving into critical AI industry topics. They discuss the dynamic competition between open and f…
Harry Stebbings, Rory O'Driscoll, and Jason Lanin discuss Coinbase's surprising AI spend reduction, Anthropic's IP theft claims against Chinese models, Microso…
Paul Erlang, co-founder and CEO of FOMO, discusses their unconventional approach to building a trading app, from giving non-founders significant equity to a da…
This episode features Harry Stebbings and Perplexity CEO Aravind Srinivas, who discusses Perplexity's transformative impact on Google's search interface, shift…
Harry Stebbings hosts Ryan Peterson, CEO of Flexport, for a candid discussion on a wide range of topics. They cover Peterson's controversial views on remote wo…
Roman Chernin, co-founder of Nebius, discusses the state of AI infrastructure, dismissing the idea of an AI bubble and asserting that the industry is in its ea…
Harry Stebbings interviews Nico, the co-founder and CEO of Corgi, a $2.5 billion valued insurance company, about his extreme workplace culture. Nico discusses…
Harry Stebbings interviews Shiv Rao, founder and CEO of Abridge, about the company's journey from a five-year "wilderness" to a $5.3BN valuation in vertical AI…
In this wide-ranging discussion, Tobi Lütke, CEO of Shopify, shares his unconventional leadership philosophy, clarifies that current mass layoffs are due to ov…
This episode analyzes the latest Mag7 earnings, noting Google and Amazon's significant AI-driven growth contrasted with Meta and Microsoft's substantial capita…
Cliff Weitzman, CEO of Speechify, shares his unconventional strategies for growth, hiring, and product-market fit, including insights gained from meeting 100 C…
Becca Lindquist, Head of Sales at Clay, provides a deep dive into modern sales strategies, leadership, and team building. She discusses critical insights into…
Harry Stebbings interviews AppLovin CEO Adam Foroughi, discussing his leadership philosophy and the company's journey through market volatility. Key themes inc…
Harry Stebbings speaks with Amjad Masad, CEO of Replit, about the evolution of programming, the impact of agentic AI, and Replit's role in empowering a billion…
This episode delves into the groundbreaking acquisition of Cursor by XAI/SpaceX for $60BN, analyzing its strategic implications and the current landscape of hi…
Harry Stebbings speaks with Aaron Levie, CEO of Box, about the transformative impact of AI on large enterprises. They discuss the future of work, the evolution…
Harry Stebbings speaks with Demis Hassabis, CEO of DeepMind, about the future of AI. They discuss AGI's definition and timeline, current bottlenecks in AI deve…
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