The Twenty Minute VCOpendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This
Episode Details
EPISODE INFO
- Released
- September 18, 2025
- Duration
- 1h 32m
- 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. Kaz Nejatian is the CEO at Opendoor (OPEN) and former COO & VP Product at Shopify; earlier he led payments at Facebook and founded the payments startup Kash (acquired in 2017). ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 01:36 Why Did Kaz Leave $300M on the Table to Join Opendoor 03:24 Why Does Kaz Believe OPEN Can Be a Good Business When the Market Doesn’t 04:28 How does Kaz Feel About OPEN Becoming a Meme Stock? 17:56 Kaz’s $0 Salary but $1BN Stock Based Compensation 25:06 Oracle and OpenAI Partnership: WTF is Going On? 33:14 Investor Diligence: Growth Over Margins 43:23 Microsoft's Investment in OpenAI: A Financial Perspective & Who Has the Power 47:35 How Anthropic’s Revenue Could Go to Zero Overnight? 53:50 Replit Raises $250M at $3BN Valuation and Higgsfield Raises $50M at $50M ARR 01:04:53 Why Adobe Have Failed in an Age of AI and What Incumbents Have To Do? 01:15:03 IPO Insights: Figure, Gemini, and Via All Go Public 01:23:09 Kalshi Quick-Fire Round: Adobe Up or Down by EOY? What Price Will OPEN Be EOY? ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow Kaz Nejatian on X: / CanadaKaz Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #kaznejatian #opendoor #shopify #ceo #microsoft #openai #memestock #orcale
SPEAKERS
Kaz Nejatian
guestCEO of Opendoor and former senior leader at Shopify.
Harry Stebbings
hostFounder and host of 20VC (The Twenty Minute VC).
Rory O’Driscoll
guestVenture capitalist and General Partner at Scale Venture Partners.
EPISODE SUMMARY
In this episode of The Twenty Minute VC, featuring Kaz Nejatian and Harry Stebbings, Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This explores opendoor’s mission bet meets frothy AI finance and market cycles Kaz Nejatian explains why he left Shopify compensation to lead Opendoor, framing home transactions as a mission-driven, software-leveraged platform with future services attached beyond the initial sale.
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