Parasite or legitimate business investment?

Her name (at least by the mechanics of a fresh save...) is Bess Sterling. I believe it can be a little hit and miss but many is the time when my Sims have given her about seven to nine times (i.e. 7000 to 9000) and then she calls back offering money on your investment.

Oh hey, I've done a thread on community closeness events!

When you first give them money, you'll establish a special relationship with them, allowing them to call your sim back. It is kind of a chain event.

When they do, two things can happen:

• They'll ask you more Simoleons. You also have a third option here: calling them out for never paying your sim back. If you do it, they'll just give your sim 2,000 Simoleons and never call you back. The other options keep the chain going, allowing them to call you back.
  
• They'll say that they got business going off thanks to your sim and offers to give your sim half of their earnings. You can accept it, gaining 25,000 Simoleons, or try to reject it, gaining relationship with them and giving you 2,500 Simoleons. The calls stop there too.

So yeah, they should eventually get the business going (or never if you're unlucky). The chain may go for long, but if you're patient, you'll eventually end up with 25,000 Simoleons.

Remember, while sims with Entrepreneur special Eco NPC trait calls you (which by default is Bess Sterling), after the first call, the special hidden relationship bit makes sure that that same sim will keep calling you.

Thank you both! Am constantly plagued IRL by money request calls/texts (usually politicians) which earns them a quick block caller and a quicker delete. Tend to be suspicious even in game as a result. Whether I have the patience in this context is another thing.