Salesforce, Slack and Dropbox Falling Behind: Are Incumbents Losing Ground?

20VC

Jun 19, 2025

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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.

Agenda:

• Meta’s $14.8B Deal for Scale: The Analysis

• Will Scale Lose Their $800M ARR? Will All Customers Leave?

• Who is the Winner from All Scale Customers Leaving?

• Who Made the Most Money From Scale?

• LPs Just Got $14B Back. Are They Reinvesting?

• Chime IPO: The Breakdown

• Ramp Hits $16B Valuation: Are We Back in 2021?

• Ramp vs Brex vs Mercury: Who’s the Real Winner?

• Gusto Going Public with $900M in ARR???

• Dropbox vs Glean: Can the Old Guard Survive the AI Wave?

• Is Slack Dead as a Platform? Salesforce Shutdown Slack API?

• Will China Dominate AI? The Bets Are In

• S&P Prediction, iPhone Assembly in the US, and Rory’s Rants

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