[selfhoster11]

Bob can remain lucky for longer than you can keep your credibility intact (aka "markets can stay irrational for longer than you can remain solvent"). Ultimately, that stance gambles on Bob's luck running out and his lack of skill being exposed in time for you to profit from it.

[vineyardmike]

Or realistically, bob looking good racking up tech debt and quitting before anyone needs to pay it off