What happens when a startup becomes a giant—and then has to reinvent itself all over again?

In this episode, Martin Casado sits down with Raghu Raghuram (former CEO of VMware) and Jeetu Patel (President and CPO at Cisco) for a deep, tactical conversation on scaling, disruption, and navigating transformation from the inside. They share hard-won lessons from leading two of the most iconic infrastructure companies in tech—through waves like virtualization, cloud, containers, and now AI.

They cover:

How to keep innovation alive inside large companies
Why the best companies operate with a founder’s mindset, even without founders
The difference between selling to buyers vs. practitioners
Why the story is the strategy, and how to tell it at scale
How Cisco is rebuilding its startup DNA in the age of AI

If you're building or leading through a major tech wave, this episode is a playbook.

Timecodes:

0:00 Introduction

2:02 Weapons of Mass Disruption: Abstractions, Business Models, and Cloud

5:57 Cisco’s Missed Cloud Wave & Resetting for Innovation

6:39 Operating Like a Startup: Speed, Scale, and Leadership

10:00 Go-to-Market Challenges: Fencing Off Innovation

11:04 Organic vs. Inorganic Growth: Lessons from VMware

12:04 The 10x Rule and Competing with Incumbents

14:39 Structuring for Disruption: Two-Pizza Teams and Ideal Customer Profiles

18:43 Storytelling as Strategy: Galvanizing Large Organizations

19:42 The AI Wave: Consumerization and Infrastructure Demands

25:34 Founders vs. Operators: Leading Transformations

31:47 Product-Led Organizations: From Sales to Product Focus

34:35 The Future of Infrastructure: AI, Market Size, and Vertical Integration

39:34 Timing, Market, Team, Product, Brand, and Scale

41:19 Authenticity, Opportunity, and Final Thoughts

Resources:

Find Martin on X: https://x.com/martin_casado

Find Raghu on X: https://x.com/raghuraghuram

Find Jeetu on X: https://x.com/jpatel41

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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.

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