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

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Sam Dewees and JR Bohannon

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.