1526 episodes
20VC: You Need $1BN To Do Seed Today: The Untold Truths of Venture | Who Wins and Who Loses in the Next Decade of VC | Why Margin and Price Matter Less in a World of AI with Sameer Dholakia, Bessemer
2026-10-19 | 1h 15 mins.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.
AGENDA:
04:55 Why This Is a Supercycle Like Never Before
07:40 Why We Backed Anthropic to Compete With the Hyperscalers
10:05 Why Anthropic Was One of Bessemer's Most Contentious Deals
11:05 Why Open Models Don't Destroy the Market for Closed Models
16:45 Does Price Matter in AI—and Which Metric Really Determines Value?
19:45 How Much Should Consumer Businesses Be Discounted for Their Revenue Quality?
20:20 Why Today's Gross Margins Matter Less Than You Think
23:00 Competition Hasn't Changed—but the Capital Behind It Has
24:00 Why Capital Is a Moat Today
25:55 Is "Triple, Triple, Double, Double" Dead?
28:00 Can You Still Succeed With a Small Seed Fund?
29:45 Who Wins and Who Loses in the Future of Venture Capital?
32:15 Why Founders Shouldn't Hate Being an "Option Bet"
34:35 Why Signalling Risk Doesn't Worry Me
51:55 Why Companies Will Stay Private Longer—and Why the IPO Window Could Reopen by 2028
56:00 How Should Retail Investors Participate in Venture Capital?
57:25 How Fireworks Could Become a $250 Billion Business
01:02:35 Why Bessemer Is Confident It Can Deliver 5x Returns on $5.75 Billion20VC: Horizontal vs Vertical Agents: Who Wins | Model Routing: Commodity or Increasing in Value | The Future of the Inference Market | Why Founders Should Take Discounts for Tier 1 Firms with Harrison Chase, LangChain
2026-10-18 | 1h 1 mins.Harrison Chase is the co-founder and CEO of LangChain, which helps developers build, test and deploy AI agents.
Backed by Sequoia Capital, Benchmark and IVP, LangChain has announced approximately $160 million in funding with the last round at a $1.25BN valuation. The company works with 35% of the Fortune 500, has surpassed one billion open-source downloads and processes over one billion events daily through LangSmith.
AGENDA:
04:10 Why Is It Still So Hard to Build AI Agents?
08:50 Will the Model Labs Eat the Agent Stack?
16:25 Is Model Routing a Real Business or a Commodity?
25:45 Why Has No One Solved AI Memory?
35:45 Why Are AI Bills Exploding as Tokens Get Cheaper?
43:25 Should Companies Be Afraid of Chinese AI Models?
46:20 Where Would Harrison Not Be Investing Today?
53:05 Should Founders Take a Discount for Benchmark and Sequoia?
57:35 OpenAI at $1.5T or Anthropic at $2T: Which Would You Buy?20VC: The Pro-Rata Battle: Valar Atomics Sues Day One Ventures | Meta Returns to the AI Frontier With Muse Wonder | NVIDIA Eyes $30B Reflection Deal & Jev Raises $870M at a $7.5B Valuation
2026-10-15 | 1h 13 mins.AGENDA:
04:00 Valar Atomics Sues Seed Investor Day One Ventures Over Pro Rata
17:00 Meta Returns to the AI Frontier With Muse Wonder
20:00 NVIDIA Eyes $30B Reflection Deal as Amazon Circles Decart
26:00 Jev Raises $870M at a $7.5B Valuation—Weeks After Launch
31:00 42 New Decacorns: The AI Boom Overtakes 2021's Record
36:00 Isomorphic Labs Eyes $50B Valuation in New Funding Talks
46:00 Anthropic Slashes Haiku Prices by 90% as AI Price War Intensifies
52:00 Bending Spoons Slashes Airtable's Team: What Do Founders Owe Employees?
57:00 Bumble to Go Private in $1.3B Deal: Can AI Transform Dating?
01:01:00 The SaaSpocalypse Deepens: Why $500M ARR May No Longer Be Enough
01:06:00 Flock Safety Cuts 270 Jobs Amid Privacy and Security Backlash20VC: Atlassian CEO on Why Agents Won't Replace Interfaces | Why Enterprises Won't Trust Chinese Models | Why The Jury Is Still Out On The Benefits of Specialised Models with Mike Cannon-Brookes
2026-10-12 | 55 mins.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.
AGENDA:
03:00 Do AI Agents Turn Traditional Software Into Just Databases?
16:00 Will Enterprises Ever Trust Chinese AI Models?
20:00 Is Building Your Own AI Model a Losing Bet?
24:00 Can AI Startups Survive When They Finally Have to Care About Costs?
30:00 What Happens When AI Gets Cheaper Than Anyone Expects?
35:00 Is Company Context the Real Moat in Enterprise AI?
41:00 What Happens When OpenAI and Anthropic Come for Your Customers?
44:00 Why Are Young Founders Cashing Out More Than Ever?
49:00 What Does Nobody Tell You About Getting Rich?20Sales: Inside Ramp's Sales Playbook: How to Build a Sales Machine with Max Freeman, SVP Sales @ Ramp
2026-10-10 | 1h 7 mins.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. Ramp's latest reported revenue exceeds $1.7BN, with a valuation of over $40BN.
AGENDA:
00:00 Inside Ramp's Sales Playbook
05:00 How Do You Find Exceptional Sellers—and Why Bankers Make the Best?
18:00 How Do You Build an Outbound Machine That Scales Beyond Your SDR Team?
24:00 How Do You Shorten Sales Cycles Without Slashing Your Price?
27:00 How Should You Pay Your First Reps—and Incentivise New Products?
34:00 How Do You Onboard Reps Who Can Actually Sell?
40:00 How High Should Quotas Be—and How Long Should Reps Get to Ramp?
44:00 How Do You Drive Customer Expansion and Forecast Revenue Accurately?
54:00 How Do You Grow as a Sales Leader Without Taking Over Every Important Deal?
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