Uploaded July 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
02:13 - Apple vs OpenAI: The Lawsuit That Could Change AI
08:00 - Is OpenAI's Hardware Dream Already Dead?
11:03 - Zuckerberg Returns to X to Take on OpenAI
16:57 - The AI Pricing War Is Just Beginning
19:17 - AI Is Burning Through Token Budgets
23:49 - Will AI Replace Designers and Figma?
30:50 - The Hidden Cost of AI for Every Business
36:35 - The $26.5 Billion AI Chip IPO Explained
41:22 - Has Venture Capital Changed Forever?
47:50 - Why the AI Secondary Market Is Booming
58:09 - Why AI Startups Are Worth Billions So Quickly
01:05:41 - Can Big Tech Keep Spending at This Pace?
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Try Plaud at plaud.ai/20VC and use code "20VC" for 10% off.
----------------------------------------------------------------------------------------------
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.
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#20vc #harrystebbings #roryodriscoll #jasonlemkin #openai #apple #zuckerberg #ai #meta
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
02:13 - Apple vs OpenAI: The Lawsuit That Could Change AI
08:00 - Is OpenAI's Hardware Dream Already Dead?
11:03 - Zuckerberg Returns to X to Take on OpenAI
16:57 - The AI Pricing War Is Just Beginning
19:17 - AI Is Burning Through Token Budgets
23:49 - Will AI Replace Designers and Figma?
30:50 - The Hidden Cost of AI for Every Business
36:35 - The $26.5 Billion AI Chip IPO Explained
41:22 - Has Venture Capital Changed Forever?
47:50 - Why the AI Secondary Market Is Booming
58:09 - Why AI Startups Are Worth Billions So Quickly
01:05:41 - Can Big Tech Keep Spending at This Pace?
----------------------------------------------------------------------------------------------
Try Plaud at plaud.ai/20VC and use code "20VC" for 10% off.
----------------------------------------------------------------------------------------------
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 #openai #apple #zuckerberg #ai #meta
