Town vs Instinct vs GrokBot | Why the AI Assistant Market Is Not a Bubble
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.…
Podcast
20VC with Harry Stebbings podcast summaries.
Every full 20VC with Harry Stebbings episode we cover, summarized with verbatim, timestamped quotes: 36 episodes and 166 articles since April 2026. Hosted by Harry Stebbings. Part of our Business coverage. New summaries every Sunday.
36 episodescovered
166 articleswith timestamped quotes
166 articleswith timestamped quotes
Jensen Huang Declares AGI Has Arrived | Tesla Launches Cybercabs | Index Pulls Out of Town
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…
How to Build Your Own Data Center & Why Every Startup Should Do It
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 CEO: AI Margins Need to Improve | Revenue Concentration Should be a Concern
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…
NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
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…
Julien Bek on Lessons from Don Valentine, Doug Leone & Alfred Lin | What Sequoia Sees in Founders
Sequoia Capital partner Julien Bek breaks down how Sequoia operates behind closed doors, including its async Investment Committee process, hunter mentality, an…
Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
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…
The AI Bubble WILL Burst | Should we be fearful of Chinese Open-Source | Jerry Murdock
Insight Partners co-founder Jerry Murdock analyzes the structural vulnerabilities in the current AI boom, warning that debt-fueled hyperscaler expansion and fr…
How to Build a $100M Growth Engine: Lessons from Wispr Flow & Superhuman | Matt Swulinski
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…
Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
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…
The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
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…
Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
This episode features Harry Stebbings, Rory O'Driscoll, Jason Calacanis, and guest Nikash Arora, CEO of Palo Alto Networks. They discuss the implications of Ai…
Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
Anastasios, CEO of Arena, discusses the rapidly evolving AI landscape, from the commoditization of models driven by open-source advancements, particularly from…
The Best AI Companies Have Unique Data Acquisition Strategies | Simile Co-founder & CEO
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…
Mercor Head of Product on Revenue Concentration from Frontier Labs
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…
We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
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…
Why OpenAI and Anthropic Won't Win the App Layer | Glean Founder
Harry Stebbings interviews Arind, founder of Glean, discussing the competitive dynamics of the AI landscape. They cover the shift towards open-source models in…
Now is the Time for the App Layer | OpenAI & Anthropic Won't Win the App Layer | Mike Mignano, USV
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…
Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips
This episode delves into the evolving landscape of AI, examining the US government's increasing involvement through regulation and potential ownership stakes i…
Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need
Harry Stebbings interviews Clay Pavore, co-founder of Sierra, delving into critical AI industry topics. They discuss the dynamic competition between open and f…
Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups
Harry Stebbings, Rory O'Driscoll, and Jason Lanin discuss Coinbase's surprising AI spend reduction, Anthropic's IP theft claims against Chinese models, Microso…
How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong
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…
How Export Controls Helped Not Hurt China & Power is the Bottleneck to AI | Perplexity CEO
This episode features Harry Stebbings and Perplexity CEO Aravind Srinivas, who discusses Perplexity's transformative impact on Google's search interface, shift…
Flexport CEO: Why Revenge and Patriotism are the Best Founder Traits
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…
Nebius Co-Founder on AI Infrastructure Bubbles | How Price Elastic is Demand for Compute
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…
The Most Intense Workplace Culture in America | The Journey from $0 to $2.6BN Valuation
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…
The Five Year Desert to Product Market Fit and a $5.3BN Valuation | Shiv Rao, Founder @ Abridge
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…
Tobi Lütke on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada
In this wide-ranging discussion, Tobi Lütke, CEO of Shopify, shares his unconventional leadership philosophy, clarifies that current mass layoffs are due to ov…
Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down
This episode analyzes the latest Mag7 earnings, noting Google and Amazon's significant AI-driven growth contrasted with Meta and Microsoft's substantial capita…
Speechify CEO: What I Learned from MrBeast and 100 of the World’s Best CEOs | Cliff Weitzman
Cliff Weitzman, CEO of Speechify, shares his unconventional strategies for growth, hiring, and product-market fit, including insights gained from meeting 100 C…
Inside Clay's Sales Playbook | Becca Lindquist
Becca Lindquist, Head of Sales at Clay, provides a deep dive into modern sales strategies, leadership, and team building. She discusses critical insights into…
AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship
Harry Stebbings interviews AppLovin CEO Adam Foroughi, discussing his leadership philosophy and the company's journey through market volatility. Key themes inc…
Replit CEO: Why Coding Models are Plateauing & Why the SaaS Apocalypse is Justified | Amjad Masad
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…
Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead?
This episode delves into the groundbreaking acquisition of Cursor by XAI/SpaceX for $60BN, analyzing its strategic implications and the current landscape of hi…
Aaron Levie
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…
Demis Hassabis: Why AGI is Bigger than the Industrial Revolution & Where Are The Bottlenecks in AI
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…