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