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Chime IPO: Are IPOs Hotter Than Ever?

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 • 00:41Meta’s $14.8B Deal for Scale: The Analysis • 08:01 Will Scale Lose Their $800M ARR? Will All Customers Leave? • 11:13 Is Alex Wand Better than Bret Taylor? • 15:57 LPs Just Got $14B Back. Are They Reinvesting? • 22:37 Jason @ Discord Being Removed • 30:25 Ramp Hits $16B Valuation: Are We Back in 2021? • 35:53 Ramp vs Brex vs Mercury: Who’s the Real Winner? • 44:44 Chime IPO • 50:32 Gusto Going Public with $900M in ARR??? • 55:27 Dropbox vs Glean: Can the Old Guard Survive the AI Wave? • 59:29 Is Slack Dead as a Platform? Salesforce Shutdown Slack API? • 01:02:07 S&P Prediction, iPhone Assembly in the US, and Rory’s Rants ---------------------------------------------------------------------------------------------- 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 #elonmusk #trump #ai #saas #stripe #foundersfund #circle

Jason LemkinguestRory O’DriscollguestHarry Stebbingshost
Jun 19, 20251h 9mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

AI deal chaos, IPO comeback, and power shifts in tech markets

  1. Meta’s $14B, 49% non-voting investment in Scale AI is framed as a talent-and-messaging play that likely triggers major customer spend reallocation away from Scale due to competitive conflicts.
  2. The panel argues liquidity is finally returning via IPOs and unusual cash distributions, but LP re-commitment will lag until real cash is received rather than merely “marked-up” public holdings.
  3. Chime’s strong IPO pop is presented as part of a window-opening pattern where attractive pricing and early aftermarket gains rebuild investor appetite after the 2021–2022 hangover.
  4. Discussion on founder/CEO removals (Discord rumor) emphasizes that violent founder replacement is “open-heart surgery,” usually value-destructive, and should never surprise the CEO if governance is competent.
  5. They debate whether incumbents (e.g., Dropbox/Slack/Salesforce) can compete with fast AI-native entrants (e.g., Glean), concluding systems-of-record advantage matters more than shipping parity features.

IDEAS WORTH REMEMBERING

5 ideas

Scale’s deal is best understood as messaging plus talent, not assets.

The group sees Meta’s purchase as economically irrational on Scale’s standalone fundamentals (cash largely paid out as dividend; revenue likely declines), but rational as a “relevance” move for public markets plus acquisition of key people and know-how.

Supplier neutrality becomes existential in frontier AI supply chains.

If a critical vendor is partly controlled by a direct competitor, labs may immediately reallocate spend to avoid leakage of roadmap signals embedded in training/eval workflows—creating overnight demand shocks for alternative providers.

In human-data businesses, “audience access” is the durable moat.

Garrett argues quality, volume, and speed drive procurement, but only access to a large, activatable expert network is defensible—especially as tasks shift to PhD-level domains, tools/agents, audio, and trajectory data.

Fast, cash distributions are psychologically powerful—but small versus total NAV.

Scale’s near-immediate dividend payout is unusually liquid and may help sentiment, yet Rory notes that even ~$20B is ~1% against trillions of private-market NAV; Jason adds LPs usually wait for cash-in-hand over 36-month IPO distribution cycles.

IPO windows reopen through underpricing and positive feedback loops.

Rory argues pops are effectively a ‘bribe’ to reset investor behavior after prior losses; strong aftermarket performance (e.g., Chime/Circle) changes the narrative and increases willingness to buy subsequent IPOs.

WORDS WORTH SAVING

5 quotes

No, I mean, I lo- I love you, but it's a dead man walking instantly. There's no way that Scale can recover from losing its founder.

Jason Lemkin

Facebook's market cap is $1.7 trillion, and their free cash flow for a quarter is $15 billion. Even if it's a total write-off, he literally goes away, Mr. Zuckerberg goes away, and in 90 days come back and said, "Whoops, that was an error, but we earned it back. Keep moving here, people."

Rory O’Driscoll

If you walk in and fire a founder or any CEO and they're surprised, you have massively failed as a board member, 'cause you didn't have the guts to tell him in advance you're worried.

Rory O’Driscoll

I always tell people, "This is open heart surgery. Even if the founding CEO wants to make the change, this is open heart surgery, and you got a one in three chance of dying."

Rory O’Driscoll

I'm starting to lose confidence in the old guard.

Jason Lemkin

Scale AI–Meta transaction structure and incentivesHuman data/training market reallocation dynamicsLiquidity, LP behavior, and IPO window reopeningChime/Circle IPO pops and IPO pricing conservatismFounder replacement governance and fiduciary dutyFintech private valuations: Ramp vs Brex vs MercuryIncumbents vs AI-native challengers (Glean, Dropbox, Slack)Microsoft–OpenAI leverage and the AGI clause ambiguity

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