Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Prior to Khosla Ventures, Keith was General Partner at Founders Fund, where he led investments for Ramp, Trade Republic, and Aven.

Eric Glyman is the Co-Founder and CEO of Ramp, America's fastest growing corporate card and finance automation platform. Under Eric’s leadership, Ramp has raised more than $1 billion in financing, with a valuation of $8.1 billion. Prior to Ramp, Eric co-founded Paribus, a price-tracking app to help consumers save money (acquired by Capital One). Ramp recently raised another $150 million series D round co-led by Founders Fund and Khosla Ventures, with a post-money valuation of $7.65 billion.
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Timestamps:

(00:00) Intro
(00:54) Founders Fund & Khosla Deals
(03:09) Ramp's Secret Ingredients for Future Finance
(05:28) Eric's Strengths & Weaknesses
(07:51) Keith’s World Class Brilliance
(09:10) Eric’s Inputs & Outputs
(12:13) Essential Advice for Founders on Speed Execution
(15:53) Top Challenges Ahead in Growth
(24:08) What Defines a Great CEO
(29:17) Direction for Today's Entrepreneurs
(31:52) Identifying Market Potential
(34:07) Product to Platform Challenges
(38:38) Quick-Fire Round
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In Today’s Episode with Eric Glyman and Keith Rabois We Discuss:

1. Behind Ramp’s Partnership with Founders Fund & Khosla Ventures:
How did the first Founders Fund deal come to be? How was the first meeting?
What does Keith mean when he says Ramp has the “secret sauce” to be successful?
What are 1-2 things Keith thinks Eric is world class at? What are 1-2 things Eric thinks Keith is world class at?
How did the latest Khosla deal come to happen?

2. Ramp: The Fastest Executing Company on the Planet:
How is Eric so good at executing at Ramp? What is his biggest advice to founders on speed of execution?
What are Eric’s biggest challenges in the next 12 months at Ramp?
Why does Keith believe momentum is crucial for early stage startups? What are some easy ways founders can build momentum?
How does Eric think AI will accelerate Ramp and the world of finance?

3. Leadership Lessons From the Best Founders:
What are Keith’s biggest lessons from Brian Chesky @ Airbnb?
What did Keith learn from Jack Dorsey @ Square about leadership?
What does Eric think founders today should build? What should they not build?
What did Eric learn from Keith on how founders should measure time & progress?

4. Hiring & Team Management:
How did Ramp build a solid talent team? What did they do differently?
Does Keith & Eric believe it is better to hire externally or promote internally? What is the right balance?
Does Keith agree founders should hire & get out the way or micromanage?
How many direct reports does Keith think is enough?
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