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

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?

Jaksot(1419)

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20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX

20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX

AGENDA: 03:46 SpaceX's $800 Billion Valuation: A Deep Dive 09:18 IPO Market Predictions for 2026 18:18 Netflix's Bold Move: Acquiring Warner Brothers 27:43 Tiger's New Fund Strategy 33:02 Databricks' ...

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20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato

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Bending Spoons is the acquisition machine of the tech world. They have acquired the likes of Evernote, Vimeo, Eventbrite, Streamyard and more. However, they never open their gates to the secrets behin...

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20VC: Thrive & OpenAI Partnership | Eventbrite Acquired for $500M | Databricks Raising $5BN at $134BN Valuation: Cheap or Not? | Why SaaS is Like Japan and The TAM Trap in Software

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AGENDA: 04:20 Thrive and OpenAI Partnership  07:14 Databricks Raising $5BN at $134BN Valuation: Cheap or Not? 17:39 Eventbrite Acquired by Bending Spoons for $500M 21:39 Pagerduty's $1BN Market Cap, J...

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20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing

20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing

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John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies: PT...

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