While him, he may not be a professional boxer but he has somehow background on it.
I believe deep inside, he's picking opponents that he has the advantage of and has the chance to easily win. What he may be after is if the opponent can fetch good amount of money. So he's looking at the figures and how much noise it will create from the boxing fans. Don't know how long he can continue exhibition fights but so far, it is still gaining buyers of tickets.
He knows what to do and makes a huge profit out of it.
Money always involves that's why a fight happens, against Jake Paul, he will surely get the bigger slice of the cake since he is the superstar and probably the one who choose whom he will negotiate to fight him.
https://www.sportingnews.com/us/boxing/news/jake-paul-tyron-woodley-purse-money/1h5jlr6xusvu5182dmpi9kn0d1
Woodley is guaranteed $500k ,so most probably Jake Paul makes at least 1 million in this fight.