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never offer money first. money should only be offered in the following scenario:

  1. it's dire, meaning that if they don't get a small amount of money something tragic will happen like they'll not get a heart transplant, their kid will die from something, they're being held hostage by somali pirates, etc. this does not mean that they could potentially fail at a business venture. if my brother started a company and called on me to make ends meet one quarter, I'd politely tell him to look up quotes by Wilbur Ross. ditto for getting behind on bills. sorry, I'm not helping you with your mortgage, you got yourself in this mess, now you live with the consequences.

  2. it's nonrecurring. I'd happily front my brother money for a surgery, but if you think I'm going to assist him with living expenses while he pays off his student loans for 3 degrees (not true, hyperbole to illustrate the point) that he's not using you're high. you having real difficulty? move to a smaller place, spend less money, and work two jobs.

  3. they've exhausted ALL other sources. aside from a loan shark, they should pursue every avenue. are their bank accounts at $0? have they tried taking money from their 401k either via a loan or a hardship withdrawal? have they looked at a personal loan from sofi?

I think this goes into the category of "just say no." most people who ask for financial assistance really just ask you because they don't want to pursue other avenues (too lazy, don't want to pay interest, don't want to pay the money back), and that's bullshit.

since you've already extended support, this will be tough, but I would personally make a clean break. say something along the lines of "I've been thinking about the help I've given you, and I've come to the decision I'm going to do that anymore. I am happy to help you get back on your feet, assist with job search, interview prep, and so on, but that last bit of money you got from me will be the last time it happens outside the holidays"

the problem is also you. you've built up the expectation that you're willing to help by actually offering to help, stifling the need for them to be independent. you cut that off, he will bitch at first, but if you stay strong, he will find a way to make it on his own. my mantra is always to offer advice first, and only under very limited circumstances do I offer financial assistance.

 
"HighlyLeveredCat" Question to people here with adult siblings. How do you make sure that your little brother/sister don't become complete parasite who are dependent on your income?

You're a student. This is an incredibly vain hypothetical.

Focus on not being a "loser" yourself first.

Commercial Real Estate Developer
 

Lead by example. Show them how to make the most of their interests/passions the same way you might have. Don't tell them what to do or how to live. No one likes that. Unless you have that type of relationship where they truly look up to you for guidance and advice. Even in that position, you'd want to teach them how to get good at things on their own. Just help them be the best version of themselves. My brother is a gearhead who lives and breaths cars. I thought it would go nowhere, but I have to let him live. Very different from my background. But I've shown him to he'd have to go about raising capital, starting something of his own, etc. and have even put together some basic projections and a pitchbook for him. But I won't give him money unless something well-thought out and somewhat advanced is in place. Gotta let him bootstrap it a bit, albeit with some guidance. Someone that's motivated enough to improve their situation is capable of getting it done with some mentoring.

 

I've been trying to get him to follow his passion by enabling him to get any resources to research and pursue his interest(Aerospace engineering). Sent him to engineering camp, paid for all the courses and he still spends most of his energy with his little gaming clan doing god knows what. Every time I show him something new like AI, machine learning, data science that would enhance his skill set, the kid just brushes it off as my attempt to get him into finance.

Cash and cash equivalents: $138,311 Financial instruments and other inventory positions owned: $448,166
 

It sounds like you are patronizing. Patronizing will always make the recipient feel less confident, less independent, and less likely to feel they can achieve something with their life. You should look at your "loser" sibling and ask yourself if you are part of the "problem".

A long time ago my sister projected her fears of my life choices onto me. I told her those were her fears and she should not influence me with her weakness. Many times, we might think we are doing a great service by stepping in and "saving" our siblings, better to just be excited and encouraging of what you can genuinely be excited and encouraging about.

 

stop what you're doing. you can lead a horse to water, but you cannot make it drink. a good friend of mine (maybe me, maybe not), had a similar situation. brother was on the couch for several years after college, no motivation, living with mom, studying useless crap and just generally lacking direction. eventually, something will click, but maybe it won't.

you've extended enough of yourself, your job from here on out is to just stay in touch, offer advice (not unsolicited, ask him if he needs help with anything he's working on), but otherwise move on with your own life

 
"HighlyLeveredCat" I've been trying to get him to follow his passion by enabling him to get any resources to research and pursue his interest(Aerospace engineering). Sent him to engineering camp, paid for all the courses and he still spends most of his energy with his little gaming clan doing god knows what. Every time I show him something new like AI, machine learning, data science that would enhance his skill set, the kid just brushes it off as my attempt to get him into finance.
Maybe you are trying too much, just let him live his own life. I mean he doesn't even think about what efforts you make to help him.
 

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