Re: the technical diligence guidance, the advice was when engaging with a technical expert a VC assigns to diligence the tech, don’t try to make it a proving match with the expert. But try to invite the expert to be on your side. Use subtle flattery and set the tone to make them tie their ego to your success.
Technical experts often are engaged or based their sense of worth in being analytical / tearing things down. So if you make it a proving match where their ego gets involved and they disagree with your approach etc they can work against you.
Instead try to frame the diligence conversation differently by setting the tone upfront.
eg say “I know we had this meeting set up as a technical diligence review for Lead VC but I looked over your background and really am impressed with your experience with XXX and so it would be a missed opportunity if I didn’t also make this a bit of a working session to get your advice on some key issues we are navigating. So I am happy to answer any questions but I would also love to get your input on some key issues we are also figuring out”