Uploaded June 2026 | Updated September 2026, 1 day ago
In the AI era, one of the most common startup moats has basically disappeared. Oren Zeev — solo VC managing $3B, backer of Navan, Tipalti, Audible, and Chegg — watched Chegg go from a $14.7B market cap to near zero when ChatGPT arrived. The lesson: if your only defensibility is your code, you're exposed.
But Oren isn't bearish on moats — he's rethinking what they look like. Proprietary data isn't just a moat anymore; it's more valuable in the age of AI than it was before. Deep integrations with legacy, archaic systems — the kind that aren't available via open APIs — are nearly impossible to replicate. Regulatory licenses and compliance (it took Tipalti four years and millions of dollars just in licenses) create real, durable barriers. And for mission-critical software where there's zero tolerance for mistakes, brand trust is everything.
The companies most at risk? Those that adapted too slowly. The ones best positioned? Founder-led companies at 50 to 1,000 people who can move fast — a massive structural advantage over 30,000-person legacy organizations.
Oren explains exactly how he's thinking about defensibility in every investment he makes today.
Watch the full conversation with Oren Zeev on Invested: bit.ly/4dlPbEp
In the AI era, one of the most common startup moats has basically disappeared. Oren Zeev — solo VC managing $3B, backer of Navan, Tipalti, Audible, and Chegg — watched Chegg go from a $14.7B market cap to near zero when ChatGPT arrived. The lesson: if your only defensibility is your code, you're exposed.
But Oren isn't bearish on moats — he's rethinking what they look like. Proprietary data isn't just a moat anymore; it's more valuable in the age of AI than it was before. Deep integrations with legacy, archaic systems — the kind that aren't available via open APIs — are nearly impossible to replicate. Regulatory licenses and compliance (it took Tipalti four years and millions of dollars just in licenses) create real, durable barriers. And for mission-critical software where there's zero tolerance for mistakes, brand trust is everything.
The companies most at risk? Those that adapted too slowly. The ones best positioned? Founder-led companies at 50 to 1,000 people who can move fast — a massive structural advantage over 30,000-person legacy organizations.
Oren explains exactly how he's thinking about defensibility in every investment he makes today.
Watch the full conversation with Oren Zeev on Invested: bit.ly/4dlPbEp
