The Twenty Minute VCIs a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell
Episode Details
EPISODE INFO
- Released
- November 6, 2025
- Duration
- 1h 18m
- Channel
- The Twenty Minute VC
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
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. ----------------------------------------------- Timestamps: 00:00 Intro 01:03 Navan's IPO: Winners, Losers and 20% Crater 20:53 Harvey Raises $150M at an $8BN Valuation 34:16 Was Sam Altman Wrong to Snap at Brad Gerstner 42:41 Why Google is a Buy and Amazon is a Short 50:30 Meta Down 10%, Buy or Sell? 52:21 If You Have Not Accelerated with AI, You Are Dead 01:10:05 Why Now is the Best Time for Series A and Worst for Seed ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: https://x.com/harrystebbings Follow Jason Lemkin on X: https://x.com/jasonlk Follow Rory O’Driscoll on X: https://x.com/rodriscoll Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #harvey #ai #vc #navan #samaltman #google #aws
SPEAKERS
Jason Lemkin
guestFounder of SaaStr and a longtime SaaS-focused investor/operator.
Harry Stebbings
hostFounder of The Twenty Minute VC (20VC) and venture capital investor/podcast host.
Rory O’Driscoll
guestVenture capitalist and tech investor providing market and fund-return analysis.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Jason Lemkin and Harry Stebbings, Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell explores vC reality check: IPO math, AI winners, board duty tensions Navan’s IPO is framed as a strong long-term outcome despite an early 20% drop, while highlighting how IPO lockups and multi-year distribution timelines make headline “returns” far less immediate than media implies.
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