Eric Glyman (CEO, Ramp) shared his operating playbook for leading one of the fastest-growing startups on his second appearance on the podcast. We also explored the unique ways Ramp leverages AI internally, strategies for startups to build moats in AI, and the concept of self-driving money. We concluded with one of the most profound and thoughtful discussions about hiring, motivations, and success I’ve ever had on the podcast. It was truly enjoyable to sit down with a seasoned portfolio founder.
00:00 Introduction and Episode Overview
01:03 Market Reflections and Ramp’s Growth
04:01 Artificial Intelligence in Business
10:09 Ramp’s AI Implementation: Toby the Slack Bot
16:49 AI’s Impact on Business Models and Hiring
31:15 The Future of Organizational Structure
31:36 The Evolution of Bookkeeping
33:49 The Impact of Automation on Bookkeeping Jobs
35:31 Streamlining Expense Management with Ramp
37:00 The Concept of Self-Driving Money
38:09 AI Integration in Ramp’s Services
39:38 Zero Touch AI and Customer Experience
40:54 Agentic AI and Practical Applications
49:15 Balancing Autonomy and Centralization in Organizations
56:09 Developing New Products at Ramp
01:04:01 Resource Allocation in Organizations
01:05:00 Creating Conditions for Success
01:08:37 Balancing Existing and New Products
01:11:02 Hiring for Curiosity
01:16:09 The Pursuit of Perfection
01:21:21 The Joy of the Process
01:24:37 Building a Timeless Product
01:33:15 Conclusion and Reflections
