The Twenty Minute VCFigma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging”
Episode Details
EPISODE INFO
- Released
- July 3, 2025
- Duration
- 1h 15m
- Channel
- The Twenty Minute VC
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. 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. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 00:59 Figma's IPO: Rule of 80, $1.5B in cash, 40% margins 02:48 Adobe Screwed the Deal: Should They Have Just Bought Canva? 14:17 Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off? 19:01 How Index Is Returning $3.5B on 2 Deals 24:22 Melio’s $2.5B Exit: Insane Growth… So Why Did They Sell?! 33:08 Massive Penthouses and the Death of Focus: AI Founders Beware 40:14 Chime, Anthropic, Menlo & The Art of Selling LPs the Future 43:06 Couchbase Acquired: PE Buyers Are Back… Or Are They? 46:45 Why No One’s Buying These 9-Figure SaaS Zombies 52:02 If You Didn’t Grow from AI By June 30, You’re Already Dead 53:42 Superhuman vs The AI-Natives: Who Wins the Replatforming War? 58:52 Oracle's $30B AI Deal: Larry Did It Before You Even Started 01:01:01 Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody. 01:05:34 Asana CEO Move & the Great Founder Exodus of 2025 01:12:14 Kalshi Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #ai #figma #oracle #adobe #aistartup #melio
SPEAKERS
Jason Lemkin
guestRory O’Driscoll
guestHarry Stebbings
host
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Jason Lemkin and Rory O’Driscoll, Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” explores figma’s IPO, Melio’s sale, and AI’s brutal new venture math The episode dissects Figma’s S-1, arguing it’s a rare billion‑dollar ARR, rule‑of‑80 SaaS asset that validates Adobe’s aborted $20B acquisition and will strongly reward early investors like Index. They contrast this with Melio’s $2.5B sale to Xero, seeing it as strategically logical yet discouraging on a revenue multiple basis and a warning about late‑stage valuations and preferences. The conversation then widens into how AI, massive capex, and winner‑take‑most dynamics are reshaping venture: reserves, down rounds, PE exits, roll‑ups, founder secondaries, and why being “AI native” (or at least AI‑relevant by mid‑2024) is now existential. They close on the surge of CEO turnover, mega‑funds like Menlo’s, the hollowing out of mid‑tier outcomes, and examples like Oracle and Vlex showing who is actually making the AI transition versus who is getting left behind.
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