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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