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"

Ron Gabrisko is the Chief Revenue Officer at Databricks, where he joined in 2016. Under his leadership, Databricks has scaled from $0 to over $4BN in annual 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

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?

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

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?

Agenda:

00:00 – Did Jason Just Kill Replit? 

03:45 – Why Claude Lies To You and Cannot Be Trusted

06:50 – You Cannot Trust Agents. Period.

10:20 – Why Windsurf Was Dead Without Claude

12:30 – Cursor vs. Lovable: What’s the Better Bet?

14:40 – Should You Still Invest in Cursor at $28B?

18:05 – Would You Bet on Anthropic at $100B or OpenAI at $300B?

24:15 – Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo

27:50 – Perplexity Just Crushed ChatGPT and Claude

32:15 – Will Cursor Build Their Own Models Before Anthropic Cuts Them Off?

33:20 – Figma’s IPO at $16B: Outrageous or Fair Game?

41:55 – 90% of Seed Funds Are Cooked—Is Rob Go Right?

52:15 – How Often Do You Meet a Founder Who Can Return the Fund?

1:08:00 – Which Seed Fund Would You Back Today?

Edwin Chen is the Founder and CEO of Surge. Founded in 2020, Surge has scaled to $1BN+ in revenue with zero external funding. At the same time, their competitor, Scale.ai raised over $1.3BN to reach $850M ARR. Today, Surge have the world’s largest model providers as customers and have just 120 employees. 

Agenda:

00:00 — “Everyone Else Is Just a Body Shop” — Edwin Calls Out the Whole Industry

01:05 — Why 90% of Big Tech Is Wasting Time on Useless Problems

03:45 — “I Don’t Do 1-on-1s” — How Surge Kills Meetings and Still Moves 10x Faster

05:55 — Will a Single Person Build a $1B Company? 

08:10 — 100x Engineers Are Real — Here’s How to Spot Them

12:10 — Why Most PhDs Are Useless in AI Training

14:20 — Built to a Billion With Zero VC — Edwin Explains How and Why

17:00 — “No Sales Team, No PR, No BS” — Why Surge Stays in the Shadows

21:15 — The Real Reason AGI Might Take Until 2040

24:45 — Will Synthetic Data Kill Human Labelling? 

29:00 — “Academic Benchmarks Are a Scam” 

31:05 — Why the Real Bottleneck in AI Isn’t Compute or Models — It’s THIS

33:00 — What Every AI Company Should Be Asking (But Isn’t)

35:15 — “No, I Wouldn’t Sell Surge for $100B” 

39:00 — Is the Application Layer Doomed? Edwin Predicts the Future of AI Startups

46:30 — Have the Leading Foundation Models Already Been Founded? 

48:10 — AGI Could Be Dangerous — And Most People Are Ignoring Why

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech | 

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin, the world’s first AI software engineer. On Friday last week they pulled off the acquisition of the year, acquiring Windsurf, following their licensing agreement with Google. Previously a world-class competitive programmer, he was a gold medalist at the International Olympiad in Informatics and a member of the U.S. Math and Physics Olympiad teams. Before Cognition, he was a founding engineer at Scale AI, helping shape the early AI infrastructure stack.

AGENDA:

00:00 – Why are founders walking away instead of going down with the ship?

01:05 – How did Cognition pull off the $220M Windsurf deal in just 72 hours?

04:45 – What really happened behind closed doors the weekend Windsurf was acquired?

07:15 – Did Google overlook a goldmine in the Windsurf team and IP?

09:00 – Who are the 100 people that secretly shape the future of AI?

12:30 – Can application startups ever gain leverage over foundation model giants like Anthropic?

14:15 – Is coding about to be replaced by simply describing what you want?

17:30 – 50% of new code is AI-written. Where does that go next?

20:45 – “We’ve gone from 0 to $80M ARR in 6 months. Quietly.”

25:00 – Are IDEs and agents just the training wheels for the real future of software engineering?

28:20 – If you could only back one—OpenAI or Anthropic—who’s the better bet?

30:00 – Why has Cognition kept its insane growth a secret… until now?

Agenda:

00:00 Windsurf was dead—then this deal changed everything

05:00 The Windsurf x Google x Cognition saga explained

09:00 The OpenAI deal collapsed—what really happened

15:00 FTC rules forced a brutal deal structure—who lost?

17:00 The investors’ returns: who actually made money?

21:30 Will Google’s corp dev team get fired over this?

23:00 Cognition’s genius $220M acquisition of Windsurf: Most brilliant Deal of the Year

26:00 The biggest recruiting flex in Silicon Valley this year

35:00 “Roll your own SaaS” is complete nonsense

38:00 Lovable vs Cursor vs Replit: who wins the coding war?

41:00 Why Lovable could be the ChatGPT of builders

44:00 Will these vibe-coded apps become durable businesses?

48:00 The shocking churn rates hidden inside AI SaaS

55:00 Are these $2B valuations actually... cheap?

56:30 Grok just destroyed GPT-4 in benchmarks—WTF?!

01:01:00 Why Grok might overtake OpenAI in the next 12 months

01:11:00 Meta just invested $3.5B in Ray-Bans—WTF?

01:12:30 Should every S&P 500 company buy Bitcoin now?

01:15:00 Will Meta kill open source? What happens to Llama 5?

Vlad Tenev is the Founder and CEO of Robinhood, the greatest story on Wall St of the last decade. In the previous 18 months, Robinhood has increased its net revenue by 58% to nearly $3B; a $500M loss in 2023 turned into a $1.1B profit in 2024. Robinhood’s stock is up roughly 4x, lifting their market cap to north of $80B. Today, Robinhood has nine lines of business that do over $100M in revenue. 

Agenda: 

00:00 – “Tokenization Is The Biggest Innovation in Finance”

03:28 – How Robinhood 4x’d Its Market Cap in 8 Months

06:40 – AI Writes 50% of All Net New Code at Robinhood

10:02 – Why Robinhood Built a Secret ChatGPT for Support

12:11 – The One Customer Type That Transformed the Business

15:29 – “CoreWeave Is Retail’s Way Into AI” — The Meme Stock Defense

18:05 – Inside Robinhood’s Tokenized Private Shares Product

21:23 – “Capital as a Service” — Vlad’s Wild Vision for Startup Fundraising

24:10 – The $100M Revenue Line Vlad Wishes He Could Kill

26:45 – Robinhood Is Building... Cash Delivery Trucks?!

29:55 – “We Were Shipping Nothing”: Vlad on the 2020–2022 Culture Crisis

33:20 – What Line of Business Will Be the Biggest For Vlad in 5 Years Time

35:11 – The One Competitor Vlad Actually Respects

36:55 – From Men’s Health to Japanese Toilets: Vlad’s Weirdest Quickfire Yet

38:40 – “I Was in the Dumps”: What 2022 Taught Vlad About Resilience

40:00 – Where Robinhood Is Headed: The Next Decade of Financial Infrastructure