Better Safe Than Sorry vs. Nothing Ventured, Nothing Gained
“Better safe than sorry.”
“Nothing ventured, nothing gained.”
Why They Conflict
One protects the downside. The other points out that the downside was the only thing on offer.
When the First May Be Useful
The potential loss exceeds the potential gain, or the gain would not meaningfully change your situation.
When the Second May Be Useful
The loss is affordable, the gain is not otherwise available, and regret has a longer shelf life than failure.
Official Ruling
Official ruling: Venture what you can afford to lose. Insure the rest. Cite the relevant saying at the hearing.