Gili Raanan: One of the Best Seed Investor of All Time: 1 Decacon, 7 Unicorns, 4 Acquisitions| E1128

ℹ️ EPISODE INFO

Released

March 18, 2024

Duration

1h 9m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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 at Sequoia Capital investing in some of the world’s best cyber security companies. ----------------------------------------------- Timestamps: (0:00) Intro (00:50) Gili’s Background (05:28) Joining Sequoia (08:25) Lessons from Sequoia (27:23) Evaluating Founders & Ideas (31:00) Importance of Market Timing (35:43) Interaction with Founders (41:22) Getting Back Up After Failure (42:45) Learning from Losses (44:22) Focus on What Works (45:25) Challenges in Matchmaking Between Founders (46:06) Prepared Mind’s Movement (49:04) Role of Price Sensitivity in Deals (49:56) Right Amount to Raise & How Much to Raise For (51:38) Speed of Execution vs. Being First to Market (53:39) Cash as a Weapon & Importance of Liquidity (54:58) State of the Market (59:08) Distinction Between Seed Funds & Opportunity Funds (01:03:45) Quick-Fire Round ----------------------------------------------- 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?

1. 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?

1. 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.

1. 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? ----------------------------------------------- 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 Twitter: https://twitter.com/HarryStebbings Follow Gili Raanan on Twitter: 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 #venturecapital #founder #giliraanan #cyberstarts #hiring #startup #investmentstrategy #sequoia #growth #investing #dougleone #mikemoritz #seed

🎤 SPEAKERS

• Gili Raanan

  guest

• Harry Stebbings

  host

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Gili Raanan and Harry Stebbings, Gili Raanan: One of the Best Seed Investor of All Time: 1 Decacon, 7 Unicorns, 4 Acquisitions| E1128 explores inside Cyberstarts: Gili Raanan’s ruthless focus on people over products Gili Raanan, one of the most successful seed investors in cybersecurity, explains why he invests almost exclusively based on people rather than markets, products, or technology. Drawing on lessons from Sequoia, he emphasizes relentless hunger, brand power, and an obsession with understanding founders’ life stories, motivations, and hardships. He details Cyberstarts’ distinctive “Sunrise” process, a deeply customer-driven validation method that precedes building product and has yielded a decacorn, multiple unicorns, and several major exits. Raanan also discusses pricing, bull-market valuations, liquidity, the role of capital, and why he remains emotionally unsentimental about selling—even while being intensely emotionally invested in founders.

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