Cloud Girl
Former Google engineer and Glean founding team member Deedy Das shares unfiltered insights on AI startup investing, what VCs actually look for, and the $100M deal that got away. In this episode, Deedy reveals: ✅ Why 100% of cold emails to VCs fail (and what works instead) ✅ The 3 things investors actually evaluate (hint: not your pitch deck) ✅ Which AI trends are overhyped vs. game-changing in 2025 ✅ How to avoid the biggest mistakes technical founders make ✅ Why he passed on Lovable (now worth $100M+) and what he learned ✅ The truth about fundraising: traction, team, and domain expertise ✅ Current AI investment opportunities: voice AI, RL environments, and more From building a $7B company (Glean) to investing at Menlo Ventures and running the Anthropic Fund, Deedy breaks down: - How to get warm intros to VCs (and why cold emails don't work) - What makes Swedish engineers build better AI products - The commoditization of startups and how to stand out - Red flags VCs can spot in 30 seconds - Why operating experience matters in venture capital Perfect for: AI founders, technical entrepreneurs, startup operators, and anyone interested in venture capital insights from someone who's been on both sides. TIMESTAMPS: 00:00 - Introduction 01:29 - Why leave a $7B startup for VC? 05:40 - Biggest mistakes technical founders make 09:08 - What's hot in AI investing right now 14:08 - Infrastructure vs. application layer investments 19:00 - What VCs actually look for (not your deck!) 25:27 - Overhyped vs. game-changing AI trends 29:08 - Why cold emails have a 0% success rate 35:12 - The Anthropic Fund and AI community 40:07 - Risk, failure, and calculated bets 42:13 - The $100M deal that got away (Lovable story) CONNECT WITH DEEDY DAS: Twitter/X: [Add handle] LinkedIn: [Add profile] Menlo Ventures: https://menlovc.com [https://menlovc.com] ABOUT THE GUEST: Deedy Das is a Principal at Menlo Ventures investing in early-stage AI, infrastructure, and SaaS companies. He was on the founding team of Glean (now valued at $7B) and previously worked as an engineer at Google and Facebook. He also manages the Anthropic Fund, supporting AI startups building with Claude. RESOURCES MENTIONED: - Glean: Enterprise AI search - Lovable: AI-powered development platform - Anthropic: AI safety and research - Scale AI: Data labeling and annotation - Thinking Machines: RL-as-a-service #AIStartups #VenturCapital #TechPodcast #StartupFunding #AIInvesting #Entrepreneurship #TechnicalFounders #MenloVentures #GleanAI #StartupAdvice --- Subscribe for more insights from founders, investors, and operators building the future of AI and technology.
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