On this episode of Invested, Michael sits down with Oren Zeev, a one-man VC with $2.7 billion AUM.

Over the last three decades, Oren has quietly built one of the most remarkable track records in venture capital, backing category-defining companies including Audible, Chegg, TripActions/Navan, Tipalti, Houzz, Riverside, and more. Operating without a traditional partnership or even an office, Oren runs Zeev Ventures largely from Café Venetia in Palo Alto — relying on speed, conviction, and founder relationships to make investments that others often miss.

In this candid and wide-ranging conversation, Michael and Oren unpack the psychology of venture investing, why most partnerships create “negative feedback loops,” and why missing a great company is far worse than making a bad investment. Oren explains how he evaluates founders in a single meeting, what makes a company defensible in the age of AI, and why adaptability matters more than code.

They also go deep on the incredible story of Navan: from an accidental street encounter that sparked the investment, to existential battles with Delta Airlines, COVID reducing revenue to nearly zero overnight, near cash collapse during hypergrowth, and surviving one of the worst IPO receptions of 2025.

The conversation also explores:

Why AI is both destroying and strengthening moats
The mental model behind successful venture investing
Why proprietary data matters more than ever
Lessons from Chegg’s collapse in the ChatGPT era
Founder-led companies vs. corporate “dinosaurs”
Why venture capital is entering its greatest era
Israeli founders, resilience, and building global companies
The dangerous obsession with unsustainable hypergrowth

Oren Zeev is the founder of Zeev Ventures, a solo venture capital firm managing billions in assets and backing some of the most important technology companies of the last two decades. Prior to founding Zeev Ventures, Oren was a General Partner at Apax Partners. He has been repeatedly recognized as one of the world’s top venture investors and is known for his concentrated, high-conviction investing style.

If you want to understand venture capital, startup moats, AI disruption, founder psychology, and what it takes to build enduring category leaders, this episode is essential viewing.

Please rate this episode 5 stars wherever you stream your podcasts!

KEY TOPICS

00:00 – Intro

02:38 – Why Venture Partnerships Fail

04:42 – Missing 100x Companies Hurts More

07:00 – How Oren Decides in 24 Hours

10:04 – The Tiny Signal Behind Riverside

15:10 – Why AI Destroyed Chegg

18:27 – The New AI Moats

22:00 – Why Oren Is Bullish on Venture

25:04 – “Microsoft Will Kill It” Again

27:12 – The Accidental Navan Investment

31:08 – Delta Nearly Killed Navan

35:18 – COVID Sent Revenue to Zero

39:06 – Leadership Under Existential Pressure

44:18 – The Worst IPO of 2025

48:56 – Why Oren Still Believes Navan Wins

59:59 – The Dangerous “10x Growth” Obsession

RESOURCES

Follow Oren on Linkedin: https://www.linkedin.com/in/ozeev/

Subscribe to Invested: https://content.aleph.vc/invested

Learn more about Aleph: aleph.vc

Subscribe to Aleph’s YouTube channel: https://www.youtube.com/@aleph-vc/

Follow Michael on Twitter: twitter.com/mikeeisenberg

Follow Michael on LinkedIn: https://www.linkedin.com/in/mieisenberg/

Follow Aleph on Twitter: https://x.com/aleph?s=20

‍Follow Aleph on LinkedIn: https://www.linkedin.com/company/aleph-vc/

‍Follow Aleph on Instagram: https://www.instagram.com/aleph.vc/

CREDITS

Executive Producer: Erica Marom

Producer: Sofi Levak, Myron Shneider, Dalit Merenfeld

Video and Editing: Nadav Elovic

Music and Creative Direction: Uri Ar

Content and Editorial: Jackie Goldberg

Design: Nimrod Sapir