20VC: The Venture Model is Broken | You Need to be Greedy and Selfish to Win Early Stage Investing | Why Margins Do Not Matter for Early-Stage Startups | The Growth Rate that is Required in a World of AI with Gili Raanan, Founder @ Cyberstarts
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.
AGENDA:
00:00 — Does the Venture Business Even Work Anymore?
05:58 — The Insane Rise of $150M Seed Rounds!
08:58 — Will Mega Funds Ever Actually Return Venture Economics?
11:13 — How Do You Value Companies Growing at Impossible Speeds?
14:50 — The Truth About Growth: Why Most Companies Eventually Plateau
18:50 — Do Margins Still Matter in the Age of AI?
24:32 — How To Make Mega Money in the World of Secondaries
28:11 — What Are Core Misalignments Between GPs and LPs That No One Discusses?
37:57 — Quick Fire: Best Investment, Most Memorable Founder, Investing Icon
VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143
Today’s show:
In this powerhouse VC roundtable, @Jason sits down with Sequoia’s Doug Leone and Cyberstarts’ Gili Raanan to share brutally honest insights on startup recruiting, evaluating second-time founders, and how to truly find product-market fit. They break down why big-tech résumés can be misleading, how to structure early teams, and what separates “missionary” talent from mercenaries. Plus, the myth of early ARR, the art of founder-board trust, and how AI is (and isn’t) reshaping startup velocity. Must-watch for founders, VCs, and anyone building from 0 to 1.
Timestamps:
(03:25) The origins of Wiz and how VCs know when to invest
(05:17) What qualities are investors looking for in founders and entrepreneurs?
(09:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups
(18:40) How to know when you’ve reached true Product Market Fit: the experts sound off
(19:20) Notion - Try it for free today at https://notion.com/twist
(25:39) The secrets of recruiting top talent
(29:54) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech
(39:38) Judging a startup’s revenue quality and “founder vs. salesman” deals
(53:38) Is venture capital kind of a SCAM?
(55:00) Seed Investing: “Pick them right and early”
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Thank you to our partners:
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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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Gili Raanan - Cybersecurity Investment Playbook - [Invest Like the Best, EP416]
My guest today is Gili Raanan. Gili is the founder of Cyberstarts, a VC firm focused on cybersecurity and the world’s first VC that is majorly backed by cyber entrepreneurs. Cyberstarts’ $50 million dollar first fund exploded to close to $2 billion in just three years. Gili describes cybersecurity today as "the perfect storm" where global conflicts and AI advancements are creating unprecedented threats. He talks about Cyberstarts' "Sunrise" methodology, which uniquely identifies customer pain points before building solutions. We discuss a focus on finding resilient talent, overcoming personal adversity, the evolution of the cybersecurity landscape, and Google's recent acquisition of Wiz, as Cyberstarts was one of Wiz's earliest investors. Please enjoy my discussion with Gili Raanan.
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For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).
Show Notes:
(00:00:00) Welcome to Invest Like the Best
(00:06:52) AI's Impact on Cybersecurity
(00:07:51) Offensive and Defensive Tactics
(00:09:32) The Future of Cybersecurity
(00:15:42) The First Fund: A Legendary Success
(00:17:36) Building a Successful Cybersecurity Company
(00:28:24) The Sunrise Methodology
(00:31:58) Reversing the Startup Process
(00:32:53) The Sunrise Methodology
(00:33:17) Identifying Market Pain Points
(00:34:57) The Importance of Customer Actions
(00:36:58) From Conversations to Software Development
(00:38:57) The Role of Simulations in Startup Success
(00:40:12) Fundraising and Valuation Strategies
(00:42:08) Pricing and Market Dynamics
(00:46:16) The Value of Superpowers in Founders
(00:50:10) Google’s Acquisition of Wiz
(01:07:24) Personal Resilience and Tragedy
(01:10:30) Future of Cybersecurity and AI
(01:12:25) The Kindest Thing Anyone Has Done For Gili
20VC: 19 Company Portfolio: 1 Decacorn, 7 Unicorns, 4 Acquisitions; One of the Best Seed Investors of All Time on How to Pick Generational Defining Founders, Why Nothing but the Founder Matters & Why the Best Investors are Never Happy w/ Gili Raanan
Gili Raanan is the Founder of Cyberstarts and one of the most successful seed investors ever. In his 19 company portfolio, Gili has invested in a decacorn (Wiz), seven unicorns and had three others acquired. Prior to Cyberstarts, Gili spent over 15 years as a General Partner @ Sequoia Capital investing in some of the world's best cyber security companies.
In Today's Episode with Gili Raanan We Discuss:
1. From Founder to World's Best Seed Investor:
How did Gili make the move into the world of venture with Sequoia?
How did Mike Moritz and Doug Leone recruit him? What was that process like?
What are 1-2 of Gili's biggest takeaways from working with Doug and Mike?
2. How to Find and Pick the Best Founders:
What did Mike Moritz teach Gili about getting to know founders?
Why does Gili look for the pain in the eyes of the founder? What questions does he ask?
What are the most common signals of truly exceptional founders, having backed 7 unicorns?
Why does Gili believe that both market and product is BS? Why are the founders all that matters?
Why does Gili believe that the founder does not have to be a domain expert in a market to create a massive company in that market?
3. What it Takes to be the Best Seed Investor:
Why does Gili believe that the best seed investors do not have theses?
How important does Gili feel the brand of the VC firm is? What were his biggest lessons on brand from spending 15 years as a General Partner @ Sequoia?
Why does Gili believe that the best investors are never happy? When you are happy, you lose.
4. 2021 is Back: Pricing, Uprounds and more
Why does Gili believe that the best companies are always expensive and will always be expensive at every round?
Why does Gili believe that 2021 pricing and funding is back?
Is this a good thing? How does Gili advise founders on how much to raise and what valuation to set with investors?
What does Gili believe are the single biggest sins from the zero interest rate environment?
