The Twenty Minute VCNavan Files to Go Public and Canva Pulls the Brakes: Why and What Happens?
Episode Details
EPISODE INFO
- Released
- June 26, 2025
- Duration
- 1h 16m
- 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 00:58 The Meta Acquisition Bombshell: Nat Friedman & Daniel Gross Join Facebook?! 09:33 Facebook’s $100 Billion Gamble: Can Zuck Buy the Future? 13:51 Is Loyalty Dead in Silicon Valley? The Great Talent Exodus 16:48 Harvey’s $5 Billion Valuation: Genius or Bubble? 22:08 The AI Gold Rush: Can Software Really Eat Human Labor? 25:19 The B2B Unicorn Dilemma: Are There Enough $100B Companies? 35:43 IPO Mania: Why Navan, Canva, and Circle Are Shaking Up the Markets 39:32 Meme Stocks & Market Madness: The Circle Rollercoaster 46:34 Canva’s Billion-Dollar Question: Why Stay Private? 49:56 Larry Ellison’s Power Play: How to Buy Back Your Own Empire 53:59 The Sales Tech Revolution: Why “Cheating” Tools Are the Next Big Thing 01:01:41 Slack Lockdown: Is B2B Software About to Get Ugly? 01:07:16 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 #sales #facebook #ipo #slack #canva #stockmemes
SPEAKERS
Rory O’Driscoll
guestVenture capitalist and panelist offering analysis on IPO timing, public vs. private markets, and AI/product dynamics.
Jason Lemkin
guestFounder of SaaStr (and former EchoSign CEO), discussing B2B SaaS, founder/VC incentives, and AI tooling/GTM strategy.
Harry Stebbings
hostHost of 20VC, moderating the panel and steering questions across IPOs, AI, and market dynamics.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Jason Lemkin, Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? explores aI talent wars, IPO timing, and B2B platform lock-in pressures rise Meta’s aggressive AI hiring/M&A is framed as “insurance” against losing user attention to AI super-assistants, not as a direct bid to monetize open-source models.
RELATED EPISODES
