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 moreFrom 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 capitalPerfect 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 - Introduction01:29 - Why leave a $7B startup for VC?05:40 - Biggest mistakes technical founders make09:08 - What's hot in AI investing right now14:08 - Infrastructure vs. application layer investments19:00 - What VCs actually look for (not your deck!)25:27 - Overhyped vs. game-changing AI trends29:08 - Why cold emails have a 0% success rate35:12 - The Anthropic Fund and AI community40:07 - Risk, failure, and calculated bets42:13 - The $100M deal that got away (Lovable story)CONNECT WITH DEEDY DAS:Twitter/X: [Add handle]LinkedIn: [Add profile]Menlo Ventures: https://menlovc.comABOUT 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.

The conversation covers insights from the tech industry, the introduction to Workado, the concept of agentic orchestration and AI, the business impact of agentic orchestration, role transformation and industry trends, and the future of Workado and industry disruption.TakeawaysTech industry insights from a 25-year veteranUnderstanding agentic orchestration and its business impactChapters00:00 Tech Industry Insights05:31 Agentic Orchestration and AI13:20 Business Impact of Agentic Orchestration23:29 Role Transformation and Industry Trends29:13 Future of Workado and Industry Disruption

Is a college degree essential for a top-tier tech career? Google Distinguished Engineer and Kubernetes pioneer Kelsey Hightower shares his unconventional path to the top, which started by quitting college after only two weeks.In this episode of the Cloud Girl Podcast, Kelsey reveals why he found college unmotivating and instead chose to pursue an A+ IT certification. He details his incredible journey from working fast food jobs to landing a contract role with BellSouth, and eventually zig-zagging his way into open source and senior roles at Google.This interview is packed with invaluable career advice for software engineers, developers, and anyone in tech who feels the traditional path isn't for them. Learn why Kelsey believes his non-traditional path is more relatable than the Ivy League route and how you can define your own metrics for success.Topics covered:The exact moment Kelsey decided to drop out of college.How to build a successful career in tech without a degree.The critical difference between a "manager" and a "boss".Kelsey's surprising perspective on the current AI hype cycle.Why community is one of the most powerful tools for career growth.#KelseyHightower #TechCareer #NoDegree #SoftwareEngineer #Kubernetes #CareerAdvice #Google #Developer