20VC with Harry Stebbings

Instinct Worth 30BN? | Microsoft Cuts 27,000 Jobs While Meta Taps Equity Markets for $95B CapEx

18K views · 1d ago · 1:00:17

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.

Topics: Anthropic Files S1 · Why Anthropic May Still Be Underestimated · The Scariest Metric in Anthropic’s S1 · Is AI Debt Financing Starting to Break? · Why Equity Markets Could Keep the AI Spending Boom Alive · Will Anthropic Have a Monster IPO?

Satya Nadella on Open vs Closed Models: Who Wins | Why Companies Need to Own Their Own Intelligence

66K views · 4d ago · 23:49

Satya Nadella is the CEO of Microsoft and one of the greatest CEOs of our time. Satya has been at the company for an astonishing 34 years. When he joined, Microsoft had a market cap of $23.5BN. 22 years later, the company was worth $300BN. At this point, Satya took the reins as CEO. Under his leadership, he has taken it from $300BN to $3.9TRN.

Topics: Why Satya Says We Should Assume AI Models Are Compromised · Why AI Needs a “Zero Trust” Architecture · Why Chain of Thought Is Not Reliable · Will Open-Weight Models Win Because They’re More Transparent? · Open vs Closed Models: Where Will AI Traffic Go? · Why Every Company Needs to Own Its Own Intelligence

Inference Will Be $10TRN Market: What No One Sees | Software Investors are F***ed | Naveen Rao

69K views · 6d ago · 1:13:26

Guest: Naveen Rao

Naveen Rao is the Founder and CEO of Unconventional AI, an AI hardware startup focused on rethinking how AI systems are built and powered. A serial entrepreneur, Naveen previously founded Nervana Systems, acquired by Intel, and co-founded MosaicML, acquired by Databricks for $1.3 billion. He later served as VP of AI at Databricks before launching Unconventional AI.

Topics: Why Energy Will Be the Biggest Bottleneck for AI · Why the US Could Run Out of Excess Power Capacity · What Compute Investors Still Get Wrong About Efficiency · Why AI Hardware Needs to Be Co-Designed With the Model · Does Chip Specialization Threaten Nvidia? · Why AI Chips Will Not Become Commoditized

The New VC Game | CoreWeave Sell-Off Creates Panic | Revenue Multiples Out of Control

34K views · 1w ago · 59:41

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.

Topics: Is Venture Broken for Great Companies Outside the AI Hype Cycle? · Why VCs Only Want Trillion-Dollar Outcomes · Why Mega-Funds Need Billion-Dollar Positions · Is Seed Investing Now Harder Than Growth Investing? · Is CoreWeave the First Crack in the AI Trade? · Anthropic’s Growth Slows: Is a $1.5TN IPO Still Cheap?

Who Wins in the Next Decade of VC | Margin and Price Matter Less in a World of AI | Sameer Dholakia

17K views · 1w ago · 1:19:51

Guest: Sameer Dholakia

Sameer Dholakia is a Partner @ Bessemer, the first that has just raised $5.75BN across a $1.75BN seed fund and $4BN growth fund. Sameer has led investments into the likes of Anthropic, Fireworks and Legora to name a few. Prior to venture, Sameer was the CEO of SendGrid, taking it from $30M in ARR to over $200M.

Topics: Why AI Is a Bigger Supercycle Than Cloud and the Internet · How Bessemer Underwrote Anthropic at a $15BN Valuation · Why Anthropic Was Bessemer’s Lowest-Voted Deal · Do Open Models Threaten Frontier Labs? · Will Enterprises Use Chinese Open-Source Models? · Is There Actually a Bear Case for Frontier Models?

Horizontal vs Vertical Agents: Who Wins? | Model Routing: Commodity or Increasing in Value?

30K views · 1w ago · 1:03:06

Topics: What Is LangChain and Why Are Agents Still So Hard to Build? · Why Better Models Force LangChain to Delete Parts of Its Product · Why Neutral Agent Harnesses Still Matter · Why Harrison Is Massively Bullish on Vertical Agents · Are Companies Really Building Their Own AI Models? · Do Specialized Models Actually Beat Frontier Models?

Valar Atomics Sues Day One Ventures | Meta's Back to the AI Frontier | NVIDIA's $30B Reflection Deal

28K views · 2w ago · 1:17:10

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.

Topics: Valar Atomics vs Day One Ventures: Is Pro Rata Broken? · Should Seed Investors Give Up Their Pro Rata Rights? · Meta Returns to the AI Frontier With Muse Wonder · Could Meta Have a Monster AI Product on Its Hands? · NVIDIA Eyes a $30BN Deal for Reflection · Does NVIDIA’s AI Push Make Thinking Machines Less Attractive?

Atlassian CEO: Why Agents Won't Replace Interfaces | Why Enterprises Won't Trust Chinese Models

23K views · 2w ago · 58:55

Guest: Atlassian CEO

Mike Cannon-Brookes is the Co-Founder and CEO of Atlassian, the company behind Jira, Confluence, Trello and Loom. Atlassian generated $6.5BN in ARR in 2026, and serves more than 350,000 customers, including over 85% of the Fortune 500. Today, Mike is leading its expansion into enterprise AI through Rovo and the Teamwork Graph, connecting company knowledge with AI agents.

Topics: Do AI Agents Turn Traditional Software Into Just Databases? · Why “Headless” Software Is a Brainless Bet · Why Design Becomes More Important in the AI Era · Is Company Context the Real Moat in Enterprise AI? · The Biggest Unsolved Design Problems With AI Agents · Will We Stop Caring Whether Content Is AI-Generated?

How to Build a Sales Machine | Max Freeman, Ramp

27K views · 2w ago · 1:12:07

Max Freeman is SVP of Sales at Ramp. He joined the company as its first sales hire. By 2025, he was leading more than 300 salespeople, helping build Ramp's sales organisation from the ground up.

Topics: Why Ramp Hires Investment Bankers Into Sales · How to Hire Great Salespeople · How to Tell a Great Seller From an Order Taker · What Salespeople Should Look for When Joining a Startup · Why Sales Is Really an Engineering Problem · When Should You Verticalize Your Sales Team?