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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode of the a16z podcast, Raghu Raghuram, VMware's former CEO and a16z's newest managing director, joins Ben Horowitz, Martin Casado, and David George for a deep dive into enterprise technology evolution. The conversation spans Raghu's journey from Netscape through VMware's transformation into a $13.5 billion company, including the strategic $1.3 billion acquisition of Nicira that generated over $2 billion in revenue. (00:54) The discussion explores the brutal browser wars with Microsoft, platform strategy execution, and how AI is creating the biggest infrastructure reset since virtualization emerged.
Former CEO of VMware and current managing director at a16z, Raghu scaled VMware from tens of millions to over $13 billion in revenue during his tenure. He led the successful $1.3 billion acquisition and integration of Nicira, which became a multi-billion dollar revenue stream for VMware. Previously, he worked at Netscape during the browser wars with Microsoft, where he gained early experience in enterprise software and product management under intense competitive pressure.
Co-founder of a16z and former VP of Product Management at Netscape, Ben led the transition from browser revenue to server products during Microsoft's competitive assault. He invested in and served on the board of Nicira, helping orchestrate its acquisition by VMware. Ben is author of several business books and known for systematizing organizational behavior, including writing the famous "Good PM, Bad PM" document.
General partner at a16z and co-founder of Nicira, Martin invented Software Defined Networking (SDN) and led the company that was acquired by VMware for $1.3 billion. His networking innovations became foundational to modern enterprise infrastructure and cloud computing. He continues to focus on infrastructure investments and has deep expertise in enterprise networking and security.
General partner at a16z focusing on enterprise and infrastructure investments. David brings extensive experience in evaluating and supporting companies building foundational technology platforms and has worked closely with portfolio companies navigating complex enterprise sales and partnership strategies.
The Nicira acquisition demonstrates how speed can be a critical competitive advantage against larger incumbents. (06:48) When VMware had to compete with Cisco for Nicira, they completed the deal over a weekend - the highest-priced acquisition at the time. This prevented Cisco from realizing the threat and bidding higher. The lesson for professionals is that when you identify a strategic opportunity, especially when facing larger competitors, moving with exceptional speed can be the difference between success and losing to better-resourced rivals. Speed also builds momentum and confidence in negotiations.
Successfully integrating acquired teams with internal teams requires acknowledging that both sides bring unique strengths. (09:37) At VMware, both the internal team and the Nicira team had built excellent technology, but in different areas. Rather than picking winners and losers, Raghu focused on identifying which elements from each team created the most customer value. This approach prevented the typical M&A failure mode where talented teams leave or become demoralized. For professionals managing integrations, the key is recognizing complementary strengths rather than competing ones.
Maintaining an independent sales team after acquisition allows better product development and customer connection. (10:55) Martin Casado noted that keeping Nicira's sales team was crucial advice from former VMware CEO Diane Greene. Independent sales teams provide direct customer feedback, better market understanding, and clearer product direction. This applies beyond M&A - professionals building new product lines or entering new markets should consider dedicated go-to-market resources rather than relying entirely on existing sales channels, especially when the product requires specialized knowledge or serves different customer needs.
AI's rapid growth means startups encounter complex enterprise challenges much faster than previous generations of companies. (23:01) Modern early-stage companies are managing $100 million GPU deals, complex cloud partnerships, and multinational expansion within their first year or two - challenges that used to emerge in years 10-15. This reality requires founders to develop sophisticated strategic thinking earlier and seek mentorship from executives who have navigated these complexities. Professionals should accelerate their learning in areas like partnership strategy, international expansion, and enterprise sales much earlier in their careers.
Building a sustainable platform means systematically expanding into adjacent markets rather than jumping to distant opportunities. (14:18) VMware's expansion from compute virtualization to management, networking, storage, and security followed a logical adjacency pattern. This approach allowed them to dominate the on-premises enterprise market even as cloud computing emerged. For professionals building products or companies, the lesson is to fully exploit adjacent opportunities before attempting large strategic leaps, as this builds sustainable competitive advantages and deeper customer relationships.