Uploaded June 2026 | Updated September 2026, 2 weeks ago
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.
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Timestamps:
00:00 Intro
01:24 Anthropic Files to Go Public
07:27 The "Billion-Dollar Position" Era: VCs Reset Their Expectations
18:15 The Trillion-Dollar Cash Grab: Google, SpaceX, and OpenAI Rush the Queue
21:37 Is the SaaS Apocalypse Over?
30:02 Cognition Raises $1 Billion at a $26 Billion Valuation
32:46 Token Budgeting Panic Hits Corporate America
01:00:36 Big Law Flex: Kirkland & Ellis Pledges $500 Million to Build In-House AI
01:12:41 Robinhood's AI Move: Automating Financial Planning vs Beating the Market
01:21:05 Apollo Warns PE Software Returns Are About to Be Disastrous
01:30:27 The 996 Work Ethic: Performative Theatre or Startup Reality?
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Follow Harry Stebbings on X:
https://x.com/harrystebbings
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https://x.com/jasonlk
Follow Rory O’Driscoll on X:
https://x.com/rodriscoll
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Legal Disclaimer:
The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates.
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#20vc #harrystebbings #roryodriscoll #jasonlemkin #anthropicipo #ai #cognition #token #996
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
01:24 Anthropic Files to Go Public
07:27 The "Billion-Dollar Position" Era: VCs Reset Their Expectations
18:15 The Trillion-Dollar Cash Grab: Google, SpaceX, and OpenAI Rush the Queue
21:37 Is the SaaS Apocalypse Over?
30:02 Cognition Raises $1 Billion at a $26 Billion Valuation
32:46 Token Budgeting Panic Hits Corporate America
01:00:36 Big Law Flex: Kirkland & Ellis Pledges $500 Million to Build In-House AI
01:12:41 Robinhood's AI Move: Automating Financial Planning vs Beating the Market
01:21:05 Apollo Warns PE Software Returns Are About to Be Disastrous
01:30:27 The 996 Work Ethic: Performative Theatre or Startup Reality?
----------------------------------------------------------------------------------------------
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:
instagram.com/20vchq
Follow 20VC on TikTok:
tiktok.com/@20vc_tok
Visit our Website:
20vc.com
Subscribe to our Newsletter:
https://www.thetwentyminutevc.com/con...
-----------------------------------------------
Legal Disclaimer:
The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates.
-----------------------------------------------
#20vc #harrystebbings #roryodriscoll #jasonlemkin #anthropicipo #ai #cognition #token #996
