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How do you tell the difference between an AI bubble and a long-term reset of how the world runs? Rajiv Menon, Managing Director at Cisco Investments and a 20-year veteran of the company, joins us to unpack how AI is actually showing up in enterprise technology—well beyond the headline frenzy. They explore what Cisco’s vantage point reveals about how the AI stack is evolving and why Southeast Asia remains a quietly powerful node in the global enterprise map. Unfair Advantage explores how the people building, funding, and transforming Southeast Asia’s next wave of enterprise technology create—and sustain—their edge. Each episode brings clarity to what drives growth across the region’s fast-evolving innovation economy. Hosted by Murli Ravi, Co-Founder and Managing Partner of Tin Men Capital, a Singapore-based VC firm focused on Series A B2B tech startups across Southeast Asia. Have a question you’d like our guest to answer on the show? Submit it here: https://forms.gle/qsv93zWPMvG2L6zd8 Connect with Rajiv and Cisco Investments: Website: https://www.ciscoinvestments.com/ Email: [email protected] (Rajiv) / [email protected] (Sherine) About Tin Men Capital: https://www.tinmen.asia/ 00:00 Welcome to Unfair Advantage 00:33 Rajiv’s introduction 00:52 Long-term impact of AI on work, life and cyber risk 02:08 Overhyped vs underhyped parts of the AI stack 04:30 Rajiv’s role and Cisco’s global M&A and investments team 06:54 From founder in Hong Kong to 20 years inside Cisco 08:18 Cisco’s US$1B AI fund and five AI pillars 11:23 Why IoT went from hype to real, scaled businesses 13:29 Connectivity management, connected cars and pervasive IoT 15:45 Why Rajiv is based in Singapore and why Southeast Asia matters 18:01 China, India, SEA and ANZ – enterprise vs consumer VC dollars 22:00 Where enterprise startups are emerging within Southeast Asia 27:17 Why being a founder is the hardest business job 29:27 The real challenge of scaling from 20 to 500 people 33:17 Peer roundtables, founder vulnerability and shared learning 37:05 Inversion, failure modes and fundraising as a daily discipline 41:07 How SEA startups and VCs can collaborate with Europe and North America 42:47 Getting personal: Rajiv as a competitive polo player 43:26 What makes Cisco Investments different as a combined VC + M&A team 45:57 Handling signaling risk when your investor can also be an acquirer 50:58 Culture fit with investors and when Tin Men walks away 52:41 How to reach Rajiv and the Cisco Investments team 53:08 How to stay connected to Tin Men