Uploaded August 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
00:57 - NVIDIA’s $6BN Poolside Deal and the Capital Wall in AI
07:30 - Is a 15x Return Enough for Seed Investors?
13:17 - Why NVIDIA Is Investing in Mercor at $20BN
20:10 - How Big Can AI Data Companies Become?
25:29 - OpenAI Confirms Its 2027 IPO
29:20 - Has Anthropic Overtaken OpenAI?
36:00 - What Is OpenAI’s Differentiated Mission Today?
38:14 - Why Coding Became the Most Important AI Market
42:38 - Why Hugging Face Could Sell for $13BN
47:08 - Citadel Cashes Out of the Leopold AI Trade
51:58 - Is AI Permanently Inflating Silicon Valley?
54:52 - How Much Longer Can the AI Boom Last?
58:07 - Are Companies Becoming Addicted to AI Tokens?
01:02:05 - Will AI Spending Force Companies to Cut Headcount?
01:08:40 - Stripe Reaccelerates to 41% Growth
01:10:17 - Will AI Kill the Old Public Software Leaderboard?
01:13:07 - Why AI Agents Still Cannot Be Trusted
01:17:02 - Is Personal AI Productivity Overhyped?
01:19:51 - Which AI Categories Are the Biggest Bubbles?
01:21:43 - Are Humanoid Robots Overhyped?
01:23:15 - Why Customer Support Software Could Disappear
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Subscribe on Spotify:
https://open.spotify.com/show/3j2KMcZ...
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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
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Visit our Website:
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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 #nvidia #openai #anthropic #stripe
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
00:57 - NVIDIA’s $6BN Poolside Deal and the Capital Wall in AI
07:30 - Is a 15x Return Enough for Seed Investors?
13:17 - Why NVIDIA Is Investing in Mercor at $20BN
20:10 - How Big Can AI Data Companies Become?
25:29 - OpenAI Confirms Its 2027 IPO
29:20 - Has Anthropic Overtaken OpenAI?
36:00 - What Is OpenAI’s Differentiated Mission Today?
38:14 - Why Coding Became the Most Important AI Market
42:38 - Why Hugging Face Could Sell for $13BN
47:08 - Citadel Cashes Out of the Leopold AI Trade
51:58 - Is AI Permanently Inflating Silicon Valley?
54:52 - How Much Longer Can the AI Boom Last?
58:07 - Are Companies Becoming Addicted to AI Tokens?
01:02:05 - Will AI Spending Force Companies to Cut Headcount?
01:08:40 - Stripe Reaccelerates to 41% Growth
01:10:17 - Will AI Kill the Old Public Software Leaderboard?
01:13:07 - Why AI Agents Still Cannot Be Trusted
01:17:02 - Is Personal AI Productivity Overhyped?
01:19:51 - Which AI Categories Are the Biggest Bubbles?
01:21:43 - Are Humanoid Robots Overhyped?
01:23:15 - Why Customer Support Software Could Disappear
----------------------------------------------------------------------------------------------
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 #nvidia #openai #anthropic #stripe
