Visual summary of operating lessons from Gili Raanan.

Lessons from Gili Raanan

Gili Raanan is the founder of Cyberstarts. Its Sunrise approach asks new teams to identify urgent cybersecurity pain points through a validation loop involving more than 60 CISO conversations before building a product. — Cyberstarts — Sunrise Approach.

Part 1: The Founder

  1. People before seed-stage ideas: Raanan says he selects seed-stage partners primarily by the people, since the initial market and product can change within weeks. — 20VC — Gili Raanan (2024).
  2. Look beyond the first pitch: He deliberately spends early founder meetings learning a person’s history rather than assessing a polished market thesis or product deck. — 20VC — Gili Raanan (2024).
  3. Look for intrinsic drive: He listens for a founder’s enthusiasm and energy about the problem, not simply whether the founder has an insider résumé. — 20VC — Gili Raanan (2024).
  4. Understand the person deeply: He asks why founders made consequential life choices, using the answers to understand motivation and how they may behave under pressure. — 20VC — Gili Raanan (2024).
  5. Test resilience before the code: Raanan looks for founders who have faced serious adversity and still excelled, treating that experience as one signal of resilience; it is his investing judgment, not a general predictor proved here. — Cyberstarts — Gili Raanan.
  6. Choose a real partner: At the seed stage he wants an open, transparent relationship before a company exists, comparing the investor relationship to an additional cofounder. — 20VC — Gili Raanan (2024).
  7. Ask why the founder chose this path: He says understanding what drives a founder helps him partner with the person better than reviewing a list of accomplishments. — 20VC — Gili Raanan (2024).
  8. Prioritize fit over sheer speed: For a young cybersecurity company, Raanan says discovering the pain point and a repeatable sales process matters more than simply being first to market. — 20VC — Gili Raanan (2024).

Part 2: The Sunrise Process and Validation

  1. Start Sunrise with buyer problems: Cyberstarts begins Sunrise with conversations with enterprise security leaders about important pain points before committing to a product. — 20VC — Gili Raanan (2024).
  2. Bring hard objections forward: Sunrise tests incumbent alternatives, pricing, channels and technical evaluation before the first line of code rather than waiting for sales objections later. — 20VC — Gili Raanan (2024).
  3. Return with a solution thesis: After the first pain-discovery round, Raanan describes a second set of 60–70 buyer conversations testing a proposed solution before building it. — 20VC — Gili Raanan (2024).
  4. Find pain with current budget: He asks prospective CISOs which single problem they would fund now, seeking present urgency rather than polite approval of a startup idea. — 20VC — Gili Raanan (2024).
  5. Review customer conversations together: Raanan says the founders run Sunrise interviews while Cyberstarts follows up, scores meetings and reviews learning weekly. — 20VC — Gili Raanan (2024).
  6. Move faster by resolving objections early: He attributes several portfolio companies’ early revenue to confronting buying and evaluation hurdles during Sunrise, a reported association rather than a guaranteed outcome. — 20VC — Gili Raanan (2024).
  7. Test the incumbent alternative: Before writing code, ask a prospective buyer why they would choose a new entrant instead of an established vendor such as Palo Alto Networks or Wiz. — 20VC — Gili Raanan (2024).
  8. Give founders direct buyer access: The Cyberstarts process connects new teams to dozens of enterprise CISOs for direct problem and solution feedback; that access is a process advantage, not proof of neutral purchasing. — Cyberstarts — Sunrise Approach.
  9. Disqualify weak ideas early: Raanan says Sunrise surfaces reasons prospects would not buy, allowing founders to reconsider ideas before committing years to a product. — 20VC — Gili Raanan (2024).
  10. Early revenue follows validation in his examples: Raanan points to several portfolio companies reaching significant ARR within their first 12–24 months after Sunrise; this is his account of selected companies, not a general promise. — 20VC — Gili Raanan (2024).

Part 3: Cybersecurity Fundamentals

  1. Cyber protection as a necessity: At a 2024 industry panel Raanan said he did not believe cybersecurity was a bubble, arguing that organizations needed protection amid real attacks. — CTech — Cybersecurity Panel.
  2. Geopolitics intensifies cyber risk: Raanan linked geopolitical conflict and recent attacks to rising demand for cybersecurity innovation; that is his market assessment, not a measured forecast. — CTech — Cybersecurity Panel.
  3. AI adds a second threat driver: In a 2025 interview he described global conflict and AI together as a “perfect storm” that could change the scale and sophistication of attacks. — Invest Like the Best — Cybersecurity Investment Playbook.
  4. New technologies create new security needs: He describes cybersecurity as following new technologies: cloud, mobile, IoT and AI each create distinct areas that need protection. — Invest Like the Best — Cybersecurity Investment Playbook.
  5. Changing threats leave room for entrants: Raanan expects evolving cyber risks to keep producing new opportunities, but emphasizes finding a real customer problem rather than assuming a feature will sell. — Invest Like the Best — Cybersecurity Investment Playbook.
  6. AI changes offense as well as defense: He argues that attackers can use the same AI advances as defenders, requiring security teams to reconsider how they respond at machine speed. — Invest Like the Best — Cybersecurity Investment Playbook.
  7. Sector focus is a deliberate bet: Raanan founded Cyberstarts in 2018 as an early-stage fund focused on cybersecurity, concentrating its work in that sector. — Cyberstarts — Gili Raanan.

Part 4: Sales and Go-To-Market

  1. Map four roles in a sale: Raanan separates the person with the problem, the budget owner, the decision-maker and the person who actually uses the product. — Invest Like the Best — Cybersecurity Investment Playbook.
  2. Prefer fewer buyer handoffs: In Wiz’s case, he says the CISO combined pain, budget, authority and ability to deploy, making early enterprise adoption easier. — Invest Like the Best — Cybersecurity Investment Playbook.
  3. Design distribution with the product: Raanan argues that category-defining startups think about user experience, sales and distribution from the first lines of code, not after building a technically good product. — Gili Raanan — The Long Game of Building Global Companies.
  4. Price against buyer value: Sunrise asks prospective customers how they would price and evaluate a proposed solution before code exists, tying the commercial model to the problem solved. — 20VC — Gili Raanan (2024).
  5. Test the buyer’s competitive choice: Sunrise asks why a buyer needs the startup rather than a familiar incumbent, which is a stronger test than simply hearing that the idea sounds good. — 20VC — Gili Raanan (2024).
  6. Generate demand, not just positioning: In 2024 Raanan said he had shifted his preferred first marketing hire from product marketing to demand generation because young software companies need more qualified opportunities. — 20VC — Gili Raanan (2024).

Part 5: Scale and Operations

  1. Control the operating pace: He warns that uncontrolled hiring or expansion can create managerial and technological complexity, so durable companies know when to slow down. — Gili Raanan — The Long Game of Building Global Companies.
  2. Defer margins, do not dismiss them: Raanan says healthy gross margins matter for a mature cybersecurity business, but he rarely makes them an immediate discussion with the youngest portfolio companies. — 20VC — Gili Raanan (2026).
  3. Hire engineers who love the craft: Discussing Wiz, he credits a highly motivated engineering team whose members enjoy writing code, while treating the productivity comparison as his own observation. — Invest Like the Best — Cybersecurity Investment Playbook.
  4. Brand can compound access: Raanan says a strong venture brand can attract founders, executives and follow-on investors, improving a firm’s ability to help its companies. — 20VC — Gili Raanan (2024).
  5. Concentrate on the chosen domain: He says Cyberstarts is a seed investor focused on cybersecurity teams and spends almost all its operating time on portfolio companies rather than broad market-thesis work. — 20VC — Gili Raanan (2024).
  6. Make the first user experience valuable: Raanan uses Wiz’s fast cloud integration and immediate insight during onboarding as an example of product design that also supports adoption. — Gili Raanan — The Long Game of Building Global Companies.

Part 6: Risk and Venture Strategy

  1. Underwrite rare venture outcomes: Raanan describes cyber venture returns as concentrated among a few winners rather than evenly distributed; this is his investing assessment. — 20VC — Gili Raanan (2026).
  2. Accept uncertainty at seed stage: He says early investors know little about a company’s ultimate market or product, so they must make judgments amid uncertainty. — 20VC — Gili Raanan (2026).
  3. Price and ownership matter to the investor: Raanan describes early-stage investing as a search for enough upside, calling investor greed and selfishness useful in that narrow context; he does not prescribe them as general founder behavior. — 20VC — Gili Raanan (2026).
  4. Size the seed round for the work: For early enterprise security software, he estimates roughly $5–6 million may be needed for a team, working product and a small go-to-market effort before Series A. — 20VC — Gili Raanan (2024).
  5. Use judgment without false certainty: In a discussion of changing venture benchmarks, he advises investors to learn from older frameworks but ultimately use their own judgment. — 20VC — Gili Raanan (2026).
  6. Spend attention on portfolio teams: Raanan says he devotes nearly all his work time to the companies Cyberstarts already backs rather than trying to win every possible cyber investment. — 20VC — Gili Raanan (2024).
  7. Back teams before metrics exist: He describes investing when founders may not yet have a company or product, judging the people and then helping them find a meaningful problem. — 20VC — Gili Raanan (2024).
  8. Treat seed price as a tradeoff: In 2026 Raanan said he had become more skeptical of inflated seed valuations, while still weighing price alongside the team and other factors. — 20VC — Gili Raanan (2026).

Part 7: Technology and Engineering

  1. Operator experience informs investing: Cyberstarts describes Raanan’s Unit 8200 service, CAPTCHA and early web-application-firewall work, two acquired software companies, and later venture career. — Cyberstarts — Gili Raanan.
  2. A useful invention still needs a business model: Raanan recounts building an early CAPTCHA prototype but failing to find its commercial model, which led him toward a customer-problem-first approach. — Invest Like the Best — Cybersecurity Investment Playbook.
  3. Sequence complex software work: Reflecting on The Mythical Man-Month and a large Unit 8200 migration, Raanan highlights team sizing, communication overhead and sequencing rather than an unsupported aphorism about architecture. — Gili Raanan — Myth of Product Version 1.0.
  4. AI security requires architectural change: In the 2025 interview he says defending against autonomous AI attacks is not merely an add-on feature; security products may need re-architecting. — Invest Like the Best — Cybersecurity Investment Playbook.
  5. Make hard technology usable: Raanan says Sunrise should lead to a solution ordinary customers can use, not just an ingenious technical invention lacking adoption. — Invest Like the Best — Cybersecurity Investment Playbook.
  6. Cloud adoption reset a security problem: He recalls customer conversations steering the Adallom team from on-premise Microsoft application security toward cloud security; market change redirected the product. — 20VC — Gili Raanan (2024).
  7. Technical invention needs customer value: His CAPTCHA story shows that widely used technology can still lack a viable business model; he argues for starting with a funded problem. — Invest Like the Best — Cybersecurity Investment Playbook.
  8. Balance feedback with product vision: Raanan warns that a single large client’s requests can turn a startup into bespoke consulting; listen to buyers while protecting a scalable product vision. — Gili Raanan — The Long Game of Building Global Companies.

Part 8: Lessons from Hypergrowth

  1. Wiz illustrates a people-first bet: Raanan backed the founders’ earlier Adallom team and later Wiz, citing the team’s experience alongside urgent customer pain and product-market fit. — Invest Like the Best — Cybersecurity Investment Playbook.
  2. Experienced teams can move decisively: He attributes part of Wiz’s execution to a founding team that had already built and scaled a cloud-security business at Microsoft before starting Wiz. — Invest Like the Best — Cybersecurity Investment Playbook.
  3. Wiz is a large historical outcome, not a formula: In his signed essay, Raanan describes Google’s $32 billion Wiz acquisition as a benchmark for building a company that can shape a global market, not a formula guaranteeing similar results. — Gili Raanan — The Long Game of Building Global Companies.
  4. Show real value in the buyer environment: Raanan says Wiz could demonstrate cloud-security findings in a prospect’s own environment early in the sales process, helping the product’s value become tangible. — Invest Like the Best — Cybersecurity Investment Playbook.
  5. Capital supports expensive enterprise building: He argues that an enterprise security company needs meaningful seed capital for product, team and initial go-to-market work, and later financing for scale. — 20VC — Gili Raanan (2024).
  6. Be a first-call board partner: Raanan says a strong early board member should be someone the CEO calls for important decisions, not merely a passive investor. — 20VC — Gili Raanan (2024).
  7. Target systemic problems, not narrow features: In his signed essay, Raanan argues that category-defining companies address a broad architectural problem, rather than becoming a feature or bespoke client project. — Gili Raanan — The Long Game of Building Global Companies.