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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