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
Episode
52 min
Read time
2 min
Topics
Productivity, Relationships, Investing
AI-Generated Summary
Key Takeaways
- ✓Venture market imbalance: In Israeli cybersecurity, representing roughly 40% of the global market, only one to two companies per 150 funded startups become unicorns annually. With seed entry prices rising from $15M post-money in 2012 to $100–150M today, the math structurally destroys returns for most investors. LPs allocating evenly across venture funds face serious capital destruction.
- ✓Growth velocity benchmark: Raanan's framework for exceptional companies targets 4x, 4x, 3x, 3x new ARR growth across the first five years of selling. Starting from $1M new ARR in year one, this trajectory compounds to $144M new ARR by year five. Wiz demonstrated this pattern in 2020, growing quarterly new ARR from $1M to $2M to $8M to $24M.
- ✓Gross margins at early stage: Founders should defer gross margin optimization entirely until later stages — Raanan explicitly tells early Cyberstarts portfolio companies to table the conversation until 2029. The priority is validating product-market fit and achieving a sales efficiency ratio where each dollar of sales and marketing spend generates at least $0.65–$0.80 of new ARR.
- ✓Employee liquidity as retention tool: Fully vested employees at high-growth private companies face structural pressure to leave for equity diversification. Cyberstarts created a recurring Employee Liquidity Fund that runs annual tender offers for portfolio company employees, replicating public market liquidity mechanics. The first program launched with Sierra, covering hundreds of employees across many millions of dollars.
- ✓Partner development framework: Building venture partnerships requires abandoning uniform operating playbooks. Rather than mapping each partner's gaps against a standard template and closing weaknesses, managers should identify each person's relative strengths and increase their exposure to those areas. Weakness improvement yields average-at-best results; strength amplification creates genuine competitive differentiation.
What It Covers
Gili Raanan, founder of Cyberstarts and seed investor in Wiz and seven other unicorns, examines why venture economics are breaking down as cybersecurity seed valuations reach $100–150M post-money, while unicorn creation rates remain at roughly one to two companies per 150 funded startups annually.
Key Questions Answered
- •Venture market imbalance: In Israeli cybersecurity, representing roughly 40% of the global market, only one to two companies per 150 funded startups become unicorns annually. With seed entry prices rising from $15M post-money in 2012 to $100–150M today, the math structurally destroys returns for most investors. LPs allocating evenly across venture funds face serious capital destruction.
- •Growth velocity benchmark: Raanan's framework for exceptional companies targets 4x, 4x, 3x, 3x new ARR growth across the first five years of selling. Starting from $1M new ARR in year one, this trajectory compounds to $144M new ARR by year five. Wiz demonstrated this pattern in 2020, growing quarterly new ARR from $1M to $2M to $8M to $24M.
- •Gross margins at early stage: Founders should defer gross margin optimization entirely until later stages — Raanan explicitly tells early Cyberstarts portfolio companies to table the conversation until 2029. The priority is validating product-market fit and achieving a sales efficiency ratio where each dollar of sales and marketing spend generates at least $0.65–$0.80 of new ARR.
- •Employee liquidity as retention tool: Fully vested employees at high-growth private companies face structural pressure to leave for equity diversification. Cyberstarts created a recurring Employee Liquidity Fund that runs annual tender offers for portfolio company employees, replicating public market liquidity mechanics. The first program launched with Sierra, covering hundreds of employees across many millions of dollars.
- •Partner development framework: Building venture partnerships requires abandoning uniform operating playbooks. Rather than mapping each partner's gaps against a standard template and closing weaknesses, managers should identify each person's relative strengths and increase their exposure to those areas. Weakness improvement yields average-at-best results; strength amplification creates genuine competitive differentiation.
Notable Moment
Raanan disclosed that he sold Cyberstarts' Wiz shares early to demonstrate liquidity to limited partners — a decision he now fully regrets. He acknowledges that holding those shares to today's valuation would have produced materially better LP returns, framing it as a lesson in prioritizing long-term conviction over early DPI signaling.
Episode Transcript
No, I don't think it's going to work. I I think it's going to end up, with some, serious, catastrophe for many of the players. The market is not balanced. A lot of that cash that's flowing into the market would be wasted. Venture is a game. You know, we know very little when we get into into investments. We need to be selfish and we need to be greedy. Those are good traits for an early stage investor. As an investor, you look at yourself and say, okay, I really fucked up. I'm not in a business of babysitting founders. This is 20 VC with me, Harry Stebbings. And what a guest we have in the hot seat for you today, Gili Ranan, founder of Cyberstoss and one of the most successful seed investors ever in his 19 company portfolio of fun one. Check this out. He invested in a decacorn, Wiz, seven unicorns and he had three other companies acquired. That is an insane hit rate. Prior to Cyber Stars, Geely spent over fifteen years as a general partner at Sequoia where he invested in some of the world's best cybersecurity companies. But before we dive into the show today, you know what's wild? It's 2026 and so so many product teams are still flying blind, buried in spreadsheets, chasing feedback across 10 different tools, trying to figure out what actually will move the needle. I've spoken with hundreds of product leaders, and the best teams all do one thing differently. They build a system to capture ideas, validate them with real data, and focus their roadmap on the right things. That's why product teams at Canva, Deliveroo, Toast, Decathlon use Jira product discovery. It pulls ideas and feedback into one place with built in tools to prioritize what will actually have the biggest impact. That's when a roadmap stops being an endless list of ideas and becomes a plan people actually believe in. Join more than 20,000 teams already using Jira product discovery. Head to atlassian.com/harry. Oh, I like it. I get my name in there. Atlassian.com/harry and start building the right thing today. After Atlassian helps your team build and ship great products, Intercom helps you support the customers using them. If you're looking for a way to transform your customer service, let me introduce you to Fin, baby. Fin is the number one AI agent for customer service resolving up to 93% of customer queries automatically. There is no other agent that can do that. Not 93% of customer queries. Okay? No other agent can do that. So why choose Fin? Fin is the best performing AI agent for CS. Fin doesn't just answer questions. It takes actions. It automates the most complex customer queries like refunds, transaction disputes, technical troubleshooting with speed and reliability. I wish my team was speedy and reliable. Beats every competitor in every head to head bake off. Completely configurable and code optional setup. My word. I mean, the benefits …
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