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SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR

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: 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... ----------------------------------------------- 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

Rory O’DriscollguestJason LemkinguestHarry Stebbingshost
Jun 11, 20261h 15mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
June 11, 2026
Duration
1h 15m
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 01:17 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: 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... ----------------------------------------------- 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

SPEAKERS

  • Rory O’Driscoll

    guest

    Venture capitalist and growth investor offering analysis on IPO dynamics, VC fund strategy, and market psychology.

  • Jason Lemkin

    guest

    SaaS-focused founder and investor sharing operator and boardroom perspectives on scaling, fundraising, and go-to-market.

  • Harry Stebbings

    host

    Founder and host of The Twenty Minute VC, interviewing leading investors and founders on tech and venture capital.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Jason Lemkin, SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR explores mega IPOs, always-on AI, lean startups reshape tech markets now SpaceX’s planned ~$75B IPO at roughly $1.8T valuation is framed as both historic and unusually risky because Elon pre-sets price, reducing traditional banker-led price discovery and increasing the odds of a weak initial trade.

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