As a rule of thumb, the more aligned incentives are, the better. When you're dealing with someone whose incentives are aligned with yours, you can usually trust that they'll do you good.

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The Encyclopedia of Mathematics:

Imagine you are a guest in a TV game show. The host, a certain Mr. Monty Hall, shows you three large doors and tells you that behind one of the doors there is a car while behind the other two there are goats. You want to win the car. He asks you to choose a door. After you have made your choice, he opens another door, revealing a goat. He then asks you whether you want to stay with your initial choice, or switch to the remaining closed door. Would you switch or stay?

This is a fascinating paradox. For a good explanation of the solution, see montyhallproblem.com.

On the 14th of April 2019, the Jordan B. Peterson Podcast starred Akira the Don. It's a fascinating conversation that covers a range of topics.

I've found Akira the Don's music very helpful, especially his album The Path with Jocko Willink. (Willink is a man you don't want to let down.)