On the tech side, we start with Brex being acquired by Capital One and what that means for Ramp. Rabois argues that banks won’t build the “finance organization of the 21st century,” and frames Ramp’s ambition as building the CFO’s “eyes, ears, and actions” across a company. We also discuss Rippling’s strategy, investor responsibilities around integrity and ethics, and how he thinks about “barrels and ammunition” when companies try to do many things at once.
From there we get into AI investing and Rabois’s view that what matters is the end-customer value proposition and the durability of the advantage. He explains Rogo as an AI “copilot” for investment bankers and talks about workflow and data moats.
The episode also turns heavily to politics and current events: Trump, tech’s relationship with the administration, immigration (including H-1B and O-1 visas), free speech, and foreign policy debates (including China, Europe, and the Middle East). We also argue through a recent incident involving law enforcement and protest/obstruction, and close with Opendoor—where Rabois lays out his view of the company’s turnaround, retail investors, and the company’s weekly “accountability” metrics updates.
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Chapters:
00:00 Introduction: Keith Rabois
02:01 Brex Acquisition & Ramp's Future
06:02 Ramp vs Rippling Competition
10:09 AI Investments
12:23 What is Rogo?
16:01 PayPal Origins & Career Journey
20:25 Political Evolution & Reagan
22:00 Iran Policy & Middle East
27:22 Greenland & Territorial Expansion
29:56 Europe Relations & Jewish Safety
32:27 Free Speech & Stanford Review
35:20 Immigration Policy & H-1B Visas
42:34 Tech & Trump Administration
44:43 Trump Pardons & Corruption
47:56 China Policy & AI Chips
49:44 Alex Pretti Shooting Debate
55:57 Law Enforcement & Authority
1:02:00 Opendoor Turnaround Strategy
1:06:38 Midterm Elections & Future