Uploaded August 2025 | Updated September 2026, 1 day ago
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.
Please rate this episode 5 stars wherever you stream your podcasts!
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 - linkedin.com/in/gigilevy
Follow Gigi on X - https://x.com/gigilevy
Subscribe to Invested here: https://content.aleph.vc/invested
Learn more about Aleph: aleph.vc
Sign up for Aleph’s monthly email newsletter: https://newsletter.aleph.vc/
Subscribe to our YouTube channel: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: twitter.com/mikeeisenberg
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: instagram.com/aleph.vc
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
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.
Please rate this episode 5 stars wherever you stream your podcasts!
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 - linkedin.com/in/gigilevy
Follow Gigi on X - https://x.com/gigilevy
Subscribe to Invested here: https://content.aleph.vc/invested
Learn more about Aleph: aleph.vc
Sign up for Aleph’s monthly email newsletter: https://newsletter.aleph.vc/
Subscribe to our YouTube channel: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: twitter.com/mikeeisenberg
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: instagram.com/aleph.vc
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
