On this episode of Invested, Michael sits down with Gigi Levy-Weiss, a former Israeli attack helicopter pilot turned entrepreneur, investor, and co-founder of the seed fund NFX. Gigi reflects on his journey from combat missions to leading companies like 888 and Playtika, highlighting lessons in leadership, military-style debrief culture, and the value of “good failures.” He shares his founder-first philosophy as a VC, his cautious stance on replacing CEOs, and his thoughts on the ethical complexities of tech - from online gambling to AI. Amid Israel’s political and security upheavals, Gigi also discusses civic responsibility and the vital role of grassroots leadership.

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KEY TOPICS

00:00 – Intro

02:00 – Why My Name is Gigi: A Personal and National Story

03:10 – From Helicopter Pilot to CEO: Gigi’s Unconventional Career Path

05:05 – The Israeli Air Force Method of Failure

09:30 – Teaching Civilian Teams to Debrief Like Fighter Pilots

11:45 – How to Build a Culture That Embraces (Good) Failure

14:25 – Celebrating Failure at Playtika

16:50 – Experience vs. Fresh Eyes: Who Should Lead After Failure?

20:10 – Why Gigi Rarely Replaces Founders, Even When They Fail

23:59 – Gigi Selling His First Company and Learning What Not to Do

26:45 – 888 and the Crash: From Private Jet Dreams to Crisis Mode

35:30 – Gigi’s Biggest Lessons from Running 888

38:55 – Hire for Talent Over Experience

40:00 – Building Playtika and Accidentally Creating Slotomania

46:50 – Wrestling with the Ethics of Online Gambling

52:20 – Facebook, Games, and Losing Faith in Tech’s “Goodness”

54:10 – If Gigi Were the AI Ethics Czar, He Would…

56:00 – The AGI Arms Race and the Collapse of Trust in Truth

59:20 – Are the Ultra-Orthodox Ahead or Behind?

01:01:00 – Founding NFX: From Angel Investor to Seed VC

01:06:00 – The Startups Gigi is Most Proud of

01:08:50 – Building Line Five: A Response to October 7th

01:10:55 – Why Gigi Took a Public Role in the Judicial Reform Protests

01:13:30 – Israel’s Founders Agreement Problem

01:16:30 – October 7th and the Rise of Civilian Emergency Networks

01:19:25 – Feature or Bug? When Citizens Replace Government

01:20:10 – The Next Generation of VCs That Give Gigi Hope

01:21:53 – Reflections on Responsibility, Legacy, and Leadership

RESOURCES

Follow Gigi on LinkedIn - https://www.linkedin.com/in/gigilevy/

Follow Gigi on X - https://x.com/gigilevy

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CREDITS

Executive Producer: Erica Marom

Producer: Myron Shneider

Video and Editing: Ron Baranov

Music and Creative Direction: Uri Ar

Content and Editorial: Kira Goldring

Design: Rony Karadi