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?