Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens?

20VC

Jun 26, 2025

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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.

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.

In Today’s Episode We Discuss:


- The Meta Acquisition Bombshell: Nat Friedman & Daniel Gross Join Facebook?!

- Facebook’s $100 Billion Gamble: Can Zuck Buy the Future?

- The “Magic Room” Theory: Why Only Insiders Get Billion-Dollar Paydays

- Is Loyalty Dead in Silicon Valley? The Great Talent Exodus

- Harvey’s $5 Billion Valuation: Genius or Bubble?

- The AI Gold Rush: Can Software Really Eat Human Labor?

- The B2B Unicorn Dilemma: Are There Enough $100B Companies?

- IPO Mania: Why Navan, Canva, and Circle Are Shaking Up the Markets

- Meme Stocks & Market Madness: The Circle Rollercoaster

- Canva’s Billion-Dollar Question: Why Stay Private?

- Larry Ellison’s Power Play: How to Buy Back Your Own Empire

- The Sales Tech Revolution: Why “Cheating” Tools Are the Next Big Thing

- Slack Lockdown: Is B2B Software About to Get Ugly?

- The Ultimate Quickfire: Will Trump Launch a Smartphone? Will the US Seize AI?

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