The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

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

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Mar 18, 2024

In this engaging discussion, Gili Raanan, founder of Cyberstarts and a distinguished seed investor, shares insights from his impressive portfolio, including a decacorn and multiple unicorns. He reveals the critical traits he looks for in exceptional founders, arguing that the founder's passion trumps market conditions. Gili also discusses the importance of personal connections in venture capital, the role of brand reputation, and how a bit of strategic 'laziness' can enhance efficiency for startups. His journey from Sequoia Capital to seed investing is both inspiring and illuminating.

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ANECDOTE

Gili's Childhood

Gili Raanan was a bright student who never did homework, preferring to improvise.
His early encounter with a Commodore 64 sparked his interest in technology and efficiency.

INSIGHT

The Value of Laziness

Laziness, combined with intelligence, can be a strength, driving efficiency and focus.
It encourages finding complementary team members to fill individual skill gaps.

ADVICE

Choosing the Right VC

Founders should choose VCs who are company builders, not just good pickers.
Look for investors who will be your first call for important decisions.

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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?