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Why Margins Don't Matter for Early-Stage Startups | Gili Raanan

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, Islands 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. ----------------------------------------------- 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 ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Gili Raanan on X: https://twitter.com/giliraanan Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #giliraanan #cyberstarts #investing #venturecapital

Gili RaananguestHarry Stebbingshost
Mar 27, 202658mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Gili Raanan on venture realities: pricing, growth, margins, and liquidity

  1. Raanan argues venture returns are structurally concentrated in a tiny set of firms, and today’s rising entry prices make the overall market increasingly imbalanced and prone to disappointing outcomes for many managers and LPs.
  2. He frames venture as a probabilistic game where investors know little early on, so the key is recognizing genuine high-velocity growth and distinguishing it from growth that is “engineered” through inefficient spending.
  3. Using Wiz, Cyera, Noname, and Island, he shows how exceptional companies can compound growth, but also how companies can plateau when the “market” is actually a narrow niche or requires painful reinvention to expand.
  4. He contends early-stage teams shouldn’t optimize for gross margin too early (even if margins ultimately matter), and he’s largely unconcerned that “too much money” will defocus strong founders if the underlying sales efficiency is sound.
  5. Raanan views IPOs primarily as branding events rather than liquidity events and advocates structured secondaries—especially employee liquidity programs—as a practical response to longer private-company timelines and talent retention needs.

IDEAS WORTH REMEMBERING

5 ideas

Assume venture won’t “work” for most players—underwrite concentration.

Raanan’s core claim is that venture outcomes are not evenly distributed; only a small group of firms reliably capture outsized returns, so LPs should avoid overly broad, equal-weighted VC allocations.

Higher entry prices break the math unless outcomes expand enough—and most won’t.

He cites cybersecurity’s low annual unicorn formation versus the steady influx of funded startups; when seed prices inflate while success rates stay low, more capital is likely to be wasted.

Treat early-stage investing as a game of imperfect information and shifting plans.

Because products and markets can change within weeks, early diligence often evaluates “smoke”; the practical implication is to focus on signals that persist through pivots—team quality, urgency of pain, and pace of adoption.

Velocity is the strongest health signal—then verify it’s organic, not manufactured.

He sees fast growth as a predictor that becomes cultural “DNA,” but warns it can be engineered through poor-yield spend; watching unit economics indicators (e.g., magic number / sales efficiency) helps separate durable growth from temporary acceleration.

Market definition matters: niches plateau; category creation can compound.

Noname’s slowdown illustrates how a narrowly scoped segment (API security as a niche) can cap growth without reinvention, while Island shows that creating a new category (enterprise browser) can unlock a growing market even against “free” incumbents.

WORDS WORTH SAVING

5 quotes

“The venture business as a whole doesn’t work. It doesn’t work. It shouldn’t work.”

Gili Raanan

“Venture is a game. We know very little when we get into investments.”

Gili Raanan

“We need to be selfish, and we need to be greedy. Those are good traits for an early-stage investor.”

Gili Raanan

“Whenever you see a company… growing super fast year over year, it becomes part of their DNA.”

Gili Raanan

“Going public is not a financial event. It’s a branding event.”

Gili Raanan

Venture returns concentration and market imbalanceRising seed entry prices and outcome probabilitiesMega funds and venture economicsOrganic vs engineered growth; sales efficiency signalsWiz and Cyera growth trajectoriesMarket size, niches, and plateau risk (Noname vs Island)Gross margins in cybersecurity vs AI; timing of optimizationPublic-market multiple compression and growth expectationsIPOs as branding events; private-market extensionSecondaries for employee retention and LP distributionsSelling too early (Wiz) and GP/LP incentivesBuilding strong venture partnerships; playing to strengthsFounder chemistry as an investing filter

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