Source
BG2Pod with Brad Gerstner and Bill Gurley — AI Enterprise - Databricks & Glean | BG2 Guest Interview (December 23, 2025) ·
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When this applies
when adopting any new, rapidly-evolving technology across an organization
The takeaway
A high experimental failure rate in an emerging technology is evidence of adequate risk-taking, not of the technology failing.
Why it works
If most experiments with a new technology succeed, you aren't pushing into genuinely new territory; a high failure rate indicates teams are stretching to find real use cases rather than playing it safe.
One level up
Judge innovation programs by whether they are exploring the frontier, not by their raw success rate.
Where it stops holding
This stops working when failures stem from poor execution or lack of basic engineering discipline rather than genuine exploration, or when failure rates stay high for years without any conversion to success.
Detail
rule: Treat a ~95% failure rate in new-technology pilots as a sign of appropriate experimentation volume, not alarm.
threshold: 95% failure cited as acceptable/expected in year one of a new technology cycle
rationale: You want everyone in the industry eager to experiment; low failure rates would mean not trying enough.
In their words
You hear these 95% of projects fail, but, like, you know, like, that's actually what you want.