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
01:17 SpaceX’s $1.8T IPO: Genius Move or Disaster Waiting to Happen?
08:50 Day One vs Year One: Predicting SpaceX’s Future
15:51 OpenAI Files to Go Public — The Next Mega IPO?
18:27 Always-On AI: Is Persistent Memory the Future?
21:32 Apple Rebuilds Siri With Google AI — Smart or Surrender?
25:15 Uber Cuts 23% of HR
27:48 Robotaxis Are Back: Uber’s Autonomous Driving Bet
29:50 Revolut Hits $115B
31:29 Founder Fundraising Horror Stories & VC Grudges
39:47 Lovable & Cursor’s Explosive Growth: The New Startup Playbook
50:59 Did Elon Pull Off the Acquisition of the Year With Cursor?
53:25 Ramp’s $44B Valuation: Fintech’s Next Giant?
55:28 AI Music Startups Are Raising Massive Rounds — Why?
56:38 Where Is All This Money Coming From? The Risk-On Market Debate
59:33 The Surprising European Tech Success Story Nobody Saw Coming
01:04:48 Should Great Companies Even Go Public Anymore?
01:06:35 Data bricks, Mega Rounds & The Private Market Boom
01:08:58 Lightning Round: The Biggest Stories We Missed
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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:
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Visit our Website:
20vc.com
Subscribe to our Newsletter:
https://www.thetwentyminutevc.com/con...
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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 #spacex #ai #openai #startups
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
01:17 SpaceX’s $1.8T IPO: Genius Move or Disaster Waiting to Happen?
08:50 Day One vs Year One: Predicting SpaceX’s Future
15:51 OpenAI Files to Go Public — The Next Mega IPO?
18:27 Always-On AI: Is Persistent Memory the Future?
21:32 Apple Rebuilds Siri With Google AI — Smart or Surrender?
25:15 Uber Cuts 23% of HR
27:48 Robotaxis Are Back: Uber’s Autonomous Driving Bet
29:50 Revolut Hits $115B
31:29 Founder Fundraising Horror Stories & VC Grudges
39:47 Lovable & Cursor’s Explosive Growth: The New Startup Playbook
50:59 Did Elon Pull Off the Acquisition of the Year With Cursor?
53:25 Ramp’s $44B Valuation: Fintech’s Next Giant?
55:28 AI Music Startups Are Raising Massive Rounds — Why?
56:38 Where Is All This Money Coming From? The Risk-On Market Debate
59:33 The Surprising European Tech Success Story Nobody Saw Coming
01:04:48 Should Great Companies Even Go Public Anymore?
01:06:35 Data bricks, Mega Rounds & The Private Market Boom
01:08:58 Lightning Round: The Biggest Stories We Missed
----------------------------------------------------------------------------------------------
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 #spacex #ai #openai #startups
