20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC

Finance, Venturecapital, Tech News, News, Siliconvalley, Technology, Investing, Startups, Business

4.4 • 637 Ratings

🗓️ 3 July 2025

⏱️ 71 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

AGENDA:

00:00 – $400B in AI CapEx: Rational Investment or Madness?

05:00 – Figma's IPO: Rule of 80, $1.5B in cash, 40% margins. Unreal.

08:00 – Adobe Screwed the Deal—Should They Have Just Bought Canva?

16:00 – Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off?

21:30 – How Index Is Returning $3.5B on 2 Deals

24:00 – Melio’s $2.5B Exit: Insane Growth… So Why Did They Sell?!

35:00 – Massive Penthouses and the Death of Focus: AI Founders Beware

39:00 – Chime, Anthropic, Menlo & The Art of Selling LPs the Future

41:00 – Couchbase Acquired: PE Buyers Are Back… Or Are They?

44:00 – Why No One’s Buying These 9-Figure SaaS Zombies

48:00 – If You Didn’t Grow from AI By June 30, You’re Already Dead

53:00 – Superhuman vs The AI-Natives: Who Wins the Replatforming War?

54:30 – Oracle's $30B AI Deal: Larry Did It Before You Even Started

56:00 – Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody.

01:01:00 – Asana CEO Move & the Great Founder Exodus of 2025

01:06:00 – Will Cluely’s Founder Be a Billionaire by 2029? Place Your Bets

Transcript

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0:00.0	The amount of money we're investing in AI right now at $300 to $400 billion a year in
0:05.1	CAPX.
0:05.7	Will you get the nearer in ROI?
0:07.3	Will it be an economically rational decision when you look back two, three years from now?
0:11.6	I don't know.
0:12.2	My rule is if you haven't grown because of AI, you failed.
0:15.5	I think venture is just going to rip.
0:17.2	You're getting a lot of money back as an LP, right?
0:19.4	Just massive amounts of cash coming back.
0:21.3	This is 20VC and it's my favorite show of the week. This is the holiday edition of Jason
0:26.2	Lemkin, Roryo Driscoll, and me shooting the shit. Now today, we cover some incredible stories.
0:31.9	We cover Figma dropping their S1. We cover the two and a half billion dollar milieu acquisition.
0:37.3	We cover P being the saving gross for venture, or is it?
0:41.9	We cover the incredible tale of index, and they're returning $3.5 billion in a matter of
0:47.8	months to their LPs.
0:49.4	This is an incredible discussion.
0:51.4	Roy's in Italy.
0:52.5	I'm in Essex.
0:53.6	It's a great holiday show.
0:55.7	But before we dive in today, here are two fun facts about our newest brand sponsor,
1:00.2	Kajabi. First, their customers just crossed a collective $8 billion in total revenue. Wow.
1:06.9	Second, Kajabi's users keep 100% of their earnings, with the average Kajabi creator bringing
	...

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