20Sales: $0-$3.7BN: The Databricks CRO’s Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko
Ron Gabrisko is the Chief Revenue Officer at Databricks, where he joined in 2016. Under his leadership, Databricks has scaled from $0 to $3.7BN annualized revenue. He has grown the sales team from 0 to over 1,000 globally, leading expansion into enterprise, government, and international markets. Ron previously held senior sales roles at Cloudera and IBM, bringing deep experience in data and AI infrastructure. His tenure at Databricks has been defined by hypergrowth, multi-product adoption, and world-class GTM execution. Agenda for Today: 00:04 – The Databricks Origin Story: Ali, Ben Horowitz & 7 PhDs 00:08 – Ali vs JPMorgan: Turning Down $10M to Stay Cloud-First 00:13 – Prospecting Day: How Ron Scaled the GTM Culture 00:16 – Why Databricks’ Pricing Model Was Its Secret Weapon 00:19 – Enterprise vs SMB: The Risky Bet That Paid Off 00:23 – From $2M to $13M ARR: How Ron Built the First Sales Engine 00:29 – Can AI Replace Salespeople? Ron’s Brutally Honest Take 00:36 – How to Get Your First Million-Dollar Rep (and Keep Them) 00:42 – The Culture Secret Behind Scaling to 5,000 Sales Reps 00:45 – Why Databricks Waited Until $500M ARR to Go International 00:52 – What Makes a Great Sales Meeting? Ron’s Gold Standard 00:58 – The Snowflake Wars: Why Ron Says Databricks Is 5 Years Ahead
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1:15:36
20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach
Miles Dieffenbach is Managing Director of Investments at Carnegie Mellon University, where he helps oversee a $4 billion endowment with a focus on venture capital, private equity, and alternative investments. Under his leadership, CMU’s private book has remained self-funding during some of the toughest years for liquidity. Agenda for Today: 00:04 – "I Had Cancer at 26 – It Changed Everything" 07:00 – Inside the $4BN Carnegie Mellon Endowment: The Investment Blueprint 10:45 – Are LPs Getting Screwed in Venture? 13:30 – 90% of LPs Shouldn’t Be in Venture – Here’s Why 16:00 – Seed Funds Are a Trap (And No One Wants to Admit It) 20:00 – The $140BN Problem with Multi-Stage Funds 24:00 – "Index Is the Best in the Game – Here's Why They Win" 29:30 – "The Dirty Secret of LPs: Brand Over Performance" 34:30 – "When Founder-Friendly Goes Too Far" 38:00 – "The OpenAI Bubble – Will It All Go to Zero?" 44:00 – "Ping Pong Diligence & Wildest Fundraising Stories"
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20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?
Agenda: 00:00 - Why Benchmark Is Bleeding Partners (and Why That’s the New Normal) 04:57 - “I Wouldn’t Leave Benchmark… Unless I Had THIS” — Jason on Brand vs Autonomy 09:01 - The Rise of the Solo GP & The Death of LP Conventional Wisdom 13:50 - The Unstoppable Force of Elad Gil & The Myth of LP Discipline 18:45 - Is Vibe Coding the New SaaS? Jason’s $10K/Month Spend Reveal 26:57 - Cursor’s Growth Is Insane—But Is It Sustainable? 31:44 - Will Microsoft, Google, or Amazon Win the AI Infra War? 37:42 - Is GitHub Copilot the Biggest Miss in Microsoft’s History? 44:15 - Are Big Tech Incumbents Now Too Powerful to Fail? 48:00 - Apple’s AI Problem: Is It Time for a Management Overhaul? 52:30 - Figma’s IPO: $30B Return, Zero Hype. What Happened? 1:06:00 - Final Bets: Cursor to $4B ARR, Lovable to $400M ARR, OpenAI to $800BN?
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1:21:26
20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China
Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Before joining a16z, he co-founded Nicira, acquired by VMware for $1.26B. At VMware, he served as CTO of Networking. Widely regarded as a visionary in enterprise infrastructure, Martin has helped shape the modern cloud computing stack. Agenda: 00:00 – Analysis of Current AI Investment Landscape 04:45 – Will Anthropic Kill the AI App Layer? 09:20 – “The Oligopoly Is Coming—Just Like Cloud” 12:50 – Are AI Models Actually Terrible Venture Investments? 15:40 – Why it is BS to Put Down AI Apps for Having Temporary Revenue 21:30 – “Open Source Is a National Security Weapon—And We're Losing” 26:40 – “Have the Foundation Models of the Future All Been Founded Already” 34:30 – Why it is BS to Denigrate AI Apps for Having Low Margins 38:40 – Does AI Make 1x Engineers 10x or 10x Becomes 100x 44:10 – “We’re All Dead Wrong About AI and Job Loss” 50:30 – “The Only Sin in Venture: Backing the Wrong Winner” 55:10 – What People Think They Know About Wealth But Do Not
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20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product
Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America's most valuable startups. Today, Fernando is the CPO @ Property Finder; one of the biggest breakout unicorns from MENA. Agenda: 00:00 – Is “having a vision” actually killing great product teams? 03:15 – Why do most products suck—and what separates the great ones? 07:20 – Should we kill the PM role entirely? Fernando says maybe. 11:45 – Is Monzo’s obsession with trust more powerful than speed? 16:10 – What’s the #1 reason internal tools will never replace SaaS? 21:00 – Will AI wipe out the need for designers and PMs? 26:30 – Is it arrogant for product teams to protect users from “bad” choices? 32:15 – What’s the future of product when OpenAI controls the whole stack? 37:40 – What Monzo product blew up—and why no one saw it coming? 42:55 – Can a bank built on principles really become a $100B company?
About The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman.
If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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