Gili Raanan is the Founder of Cyberstarts, one of the best performing venture funds of the last decade. He is famed for being the seed investor in Wiz, Island and Cyera, leading to multiple 10x+ funds. He has the only remaining monopoly in venture; cyber security in Israel. If it is good, Gili sees it, it is that simple.
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Timestamps:
00:00 Intro
01:27 Does the Venture Business Even Work Anymore?
08:27 Are We Just Being Boomers? The Counter-Argument on Outcome Sizes
10:38 Will Mega Funds Be Able to Return Venture Economics?
12:48 How to Tell If a Company’s Growth Is Real or Engineered
16:11 Wiz vs Sierra: What Fast Growth Actually Looks Like
19:40 Does Market Size Determine Whether a Company Plateaus?
21:46 Island – Building a Market That Didn’t Exist
21:36 Does Too Much Money Defocus Great Founders?
26:36 Do Gross Margins Still Matter in the AI Era?
32:05 Why Public Markets Are Crushing Software Multiples Right Now
34:11 Is the Extension of Private Markets Fundamentally Good?
35:34 Using Secondaries to Retain Talent & Return Capital to LPs
41:06 Did Gili Sell Wiz Too Early & What Did He Learn?
42:30 GP/LP Misalignment: The Hidden Problem Nobody Talks About
44:21 How Gili Has Changed as an Investor
51:09 How to Build a Great Venture Partnership
53:39 Quick-Fire Round
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