Is my aunt using me?

I have a very wealthy aunt who is in the top 1% of the top 1%. I see her every couple of weeks, when she invites me down to accompany her out to dinner or perform work around the house for her. Long story short, I’m an entrepreneur launching a very exciting and possibly *extremely* profitable business online.

In this process my biggest problem is more cash for expansion. I honestly work very, very hard and am dedicated 110%, but so much advancement could be made overnight had I been blessed with the cash to do so.

Anyway, one day I was driving my aunt to the airport (I am basically her personal assistant when she summons me to be), and she told me how nice money is to have because you therefore never have to worry about it. Without thinking, she blurted out that she donates about $150,000 a year to various and always changing organizations. Upon saying this, I saw her face immediately switch to a bright red “WHOOPS” expression.

Now I know I have absolutely zero claim to her money at all, but am I wrong to feel somewhat unloved by her now that I realize she’s pumping mind-blowing amounts of money into a multitude of other directions and rejecting mine – all the while acting like my best friend, biggest ally, and cheerleader?

Also let me just mention that when I do work around her house she will throw me $20 – $40 bucks or so, but when I subtract the gasoline I spend traveling 40 minutes each way to her house, is not as great as it first appears.

I don’t want to seem selfish or entitled – I’ve been maintaining being a good nephew and just smiling and helping her in every way she asks – but at the same time I can’t help but realize that a very minuscule percent of the money/lifeblood she is constantly spreading elsewhere, to complete strangers, would vastly advance my business, and ultimately the quality of my entire life in exponential proportions.

Deep down I feel like she might simply be using me to be her little helper when needed, and doesn’t actually want to see me succeed because then she’d lose me as such – and that’s why she doesn’t actually help financially. This is the only reason I can find for her decision not to donate to my business because she gives so much away to others. Could she be putting up a front that she is “rooting for me” and “wants to see me succeed” but really just wants to keep me where I am and benefit from my younger ignorance and desire to be a good nephew? Am I playing the fool right into her hands and advantage? Could I be experiencing a form of “all talk and no walk” by her? I really hope you answer this Rabbi and Susan as this has been a mind ripping situation for me. I sure could use your wisdom!


Dear Drew,

We found your question quite intriguing, partially because you show great maturity by recognizing that you are not entitled to your aunt’s wealth but that, since she is an older member of the family, you actually have a responsibility towards her.

At the same time, you are struggling to build a business and see how effortlessly she could solve what you see as your greatest problem. That makes you suspect that she actually doesn’t want you to succeed and leaves you with hurt feelings. You now see her as “throwing” money at you when you help her, but we’re willing to bet that she politely hands it to you and the word throw reflects your incipient resentment rather than her actions. 

We, of course, do not know your aunt nor do we know you.  However, we did pick up certain clues in your letter (which we needed to shorten but we retained both the meaning and the flavor). It seems to us that you have not yet developed a full understanding of business. This is imperative in order for you to succeed.

You explained that you could think of only one reason for your aunt’s decision not to donate to your business.

We are struck by your use of the word donate. One donates to charity but one invests in a business. Your aunt seems to be a very charitable woman. She may or may not be a savvy businesswoman and she may or may not invest her money in start-ups. Either way, it seems to us that you would like her to invest in you or help you, not to give you charity.

This means that you need to approach her as a businessman, not as a nephew, though obviously your relationship gives you the opening. If she does evaluate investments, she may have valuable feedback for you. If she is indeed in the top one-hundredth of the top 1% she most definitely employs the professional services of financial advisors and money managers. 

We’d advise you to ask your aunt if she’d be willing to ask her advisors to look over your business plan. If you do not yet have a formal, professional business plan you might want to approach your aunt and ask if she will help you (now we are talking about a donation or gift) take classes or hire a professional to guide you on how to turn an idea into a viable business. Very few new businesses succeed and she would be doing you a greater kindness by helping you get off on the right foot (or realize that your idea, as is, is not viable) than by blindly giving you money.

We don’t want to discourage you from being a good nephew, but it is possible that being at her beck and call makes your aunt think of you as an aimless boy rather than as a busy man ready to embark on a seriously successful business career. Even your description of the money she gives you being used up in buying gas suggests that you are thinking in a smaller way than a successful businessman must.

You might want to show her a more proactive face and initiate contact instead of waiting to be summoned. Let her know that you have a tightly scheduled month coming up because you are working so hard but want to be available if she needs you so could you and she please plan out your schedules in advance. Call her just to say hi and see how she is rather than waiting for her to call you.

Investors seldom put their money into enterprises run by those they see as their “little helper” as you put it.  Once you see yourself in a different and more serious light, your aunt will most likely also start seeing you differently.

You cannot dictate your aunt’s actions but you can control your own. We encourage you to think, act and present yourself as a business professional and we are sure that this will help move you onto the path of becoming one. We do want to bring our books, Thou Shall Prosper: The Ten Commandments for Making Money and Business Secrets from the Bible: Spiritual Success Strategies for Financial Abundance to your attention as we think the practical guidance they give could be helpful in reshaping your vision of yourself. 

Wishing you a prosperous and family-friendly future,

Rabbi Daniel and Susan Lapin


33 thoughts on “Is my aunt using me?”

  1. Drew here. Rabbi Lapin, thank you for the amazing reply. You made some excellent points and I’ve reflected and observed some things about myself and the situation with my aunt at large. Before I expand on that though, I’d just like to touch on the mystique of my use of the word “throwing” that’s gained so much attention in the comments. It is native slang in the NY/NJ area (where I live), for example after the valet driver brings me my car I might “throw him a five.” It’s not meant to sound aggressive but I can absolutely see how it would sound that way. And for the record she does politely hand me the $20 – $40 as Rabbi Lapin suggested. That out of the way, I’ve really reflected on her interactions with me over a long timeline. And I am pretty certain she is indeed showing me love by not throwing money blindly at me. “Tough love” I think they call it. Sometimes it does a kid more good to let him scrape his knees when learning to ride a bike than continuing with the training wheels. We did have another not-too-distant family member who was spoiled with easy money from his parents and it did not serve him at all in the long run. Perhaps her decades of life experience over mine have bestowed a form of wisdom on her that I am just beginning to grasp. Another thing Rabbi Lapin touched on was that she may view me as an aimless boy instead of a busy man ready to embark on a seriously successful business career. You certainly nailed this one right on the head. This is entirely my fault – for some reason I always tip toe around her and never reveal an entirely different side of myself that exists, which is indeed a much more mature and leading persona. I think because I wanted to appease her with gentleness and maintain that same playful dynamic she and I had since my younger years. It’s funny how some relationships can stick like this. Even my friends from high school can bring a younger version of myself up to the surface after being submerged for quite some time. I am going to continue contemplating over this and reflecting on the notes I’ve taken from your answer Rabbi Lapin. You and Susan are great, and I really appreciate your guidance.

    1. Clare Koesters

      You sound like a very level-headed and driven person – I am sure you will become a great success. (Thank you for the clarification on language – we often are unaware of regional variations!)

  2. I find this to be good advice too, however, I would also remind him that even if she chooses not to help, God knows his heart and will bless him. Also, he should pray that if it be within the Lord’s will, the aunt to be lead to help him.

  3. Your advice, as always was excellent. I’d add that perhaps his Aunt is waiting for him to act decisevly and professionally. She may be doing so not out of anything but love. And perhaps she will never give or invest a dime, preferring that their relationship be based on love, family ties, and respect. She may also want him to make it on his own, for which he will be grateful one day. Treat your rich relatives as you would all relatives, with love, respect, and kindness, not as a potential source if cash. Would you treat her differently if she was penniless? While I will never be rich, I can empathize with some one who is and their never knowing if they are loved for who they are or for their money.

    1. You are making excellent points, Carolyn. We knew a young woman who came from a very wealthy family who kept her last name and background a complete secret for exactly the reason you state. Her now-husband was convinced that she worked for the CIA because of how little she shared of her life.

  4. Susan Pistorio

    Oh, my goodness, Rabbi Lapin and Susan! I feel so smart! The word “donate” leaped out at me, and my immediate response was the same as yours. Everything you said to this young man was spot on. I gave similar counsel to my own son, years ago, when he began to see that his rock band should be at least self-supporting. As he had been through the US GIC system, and was attending a university (thankfully, not an expensive one) he was very ambivalent about charging money for the band’s “merch,” and thought of asking the fans for donations. “No, no, no, no!” I would say, and etc about how they had something of value to offer, that for a reasonable price would be an item to treasure for their followers.
    These years hence, he has outgrown this confusion, and in fact recognizes his worth in an e-commerce operation, and continually lobbies the powers that be for appropriate compensation for the value he provides!
    His degree in philosophy hasn’t done him a lot of good, but he is wise enough to listen to his mother, who is wise enough to listen to Rabbi and Susan Lapin every chance she gets. 🙂

    1. How fortunate you and your son both are that he has a wise mother and listens to her! It is one of many sad comments on our educational system that working for and making money are seen as negative activities and causes for embarrassment.

  5. hello,

    such a good question and such a great reply !! wise man you are Rabbi Lapin !! so impressed with your reply , just wow!


  6. Thoughtful wisdom, excellent answer.

    There is one thing I could add, maybe. Have you ever seen the movie “Greedy” with Michael J. Fox? Spoiler alert, if you haven’t.

    It is possible that the aunt has to deal with people who like her or claim to love her but really just want her money. She might be asking, “Who really loves me?” in her head all the time. “Would they love me and take care of me if I had no money?” The nephew seems to, and let’s hope that’s true.

    I have a desire to make it (or not) on my own. Maybe I’m too independent, but it seems that a lot of times money given has a lot of strings attached. Plus the downside problems if you use it and fail. If the business is a good one and managed well it will succeed. Perhaps a little slower, but also perhaps stronger. If family groups or even communities (church or synagogue) really followed Torah, wit love and the Spirit, then there wouldn’t be any downside.

    I find it fascinating that God said there wouldn’t be any poor people in Israel if they really followed what He said.


    1. Rabbi Daniel Lapin

      Dear Bruce-
      We appreciate you writing. Do you recommend we see Greedy? Some movies are worth the investment of time. Regarding your observation (Deut 15) about rich and poor, a few verses away it also states that there will always be poor among us. How do we reconcile seemingly contradictory statements?
      I explain this contradiction in my book, Thou Shall Prosper. Rich and poor have specific meaning in the Bible and do not define anyone’s essence. Unlike animals, humans are touched by the finger of God and can grow. Animals have only a present. Unlike anteaters and zebras, we have a past and a future as well. Was the pitiful tycoon, Howard Hughes, living a lonely and paranoid existence really rich? Is the young and underpaid medical resident working 12 hour shifts and sharing a tiny apartment with three other doctors-in-training, really poor?
      A goldfish without enough food can be thought of as poor. A mouse living in a grain warehouse can be considered rich. But those terms do not apply to humans. For humans those terms are relative. No matter your finances, you can easily find someone with far less than you as you can find someone with far more. Look one way and you can feel rich, while a glance in the other direction can make you feel poor.

      1. Yes, I think Greedy is a decent movie. You would probably enjoy it. Interesting character studies. Not exactly G rated, but not bad. The first time I watched it I had some difficulty making it all the way through. Once I got to the ending, though, it was worth it and could watch it again. Look past some of the stupid stuff and there are some very good themes.

        With Deuteronomy 15 there is a seeming paradox. Verse 4 “there will be no poor among you,” and verse 11 “there will never cease to be poor.” Jesus also says “you always have the poor with you” (Matthew 26:11, Mark 14:7, John 12:8) but “you do not always have me.” My resolve for the apparent paradox is in Deuteronomy 15:5 “if only you will strictly obey the voice of the Lord your God, being careful to do all this commandment that I command you today.”

        The simple truth is we don’t do what He says. Therefore we “always have the poor.”

        The church has backed away from much of God’s Words, substituting tradition and philosophies of men. If you’ll forgive me, so has the synagogue and for much the same reasons. Except the synagogue I think does a better job practicing community, even to the point of setting up some of their members in business with loans.

        I like your analogies. A mouse in a grain warehouse might be rich, but is still fearful and cannot enjoy it much except for being able to eat regular. He can only be momentarily content. If I have God, I am rich and can share those riches with others. There is no end to my wealth. Howard Hughes was indeed poor, because all he had (apparently) was stuff that would burn. I will carry my wealth into the next world. Howie will be a pauper there. The medical resident has the promise of eventual wealth or ego-feeding driving him (or her) so his wealth is deferred but it is still ephemeral.

        If the nephew and the aunt were both following Torah, I think the answer to the dilemma would be self-evident. What causes us problems is when we are doing our own thing rather than His. Selfishness can only take us so far and our inherent self-destructive tendencies take over.

        I’ll have to pick up a copy of Thou Shall Prosper, if only to share with my wife the advice to never retire. She’s freaking out a little now that we’ve hit the ’60’s and I keep telling her I don’t want to retire!


  7. Wow! I’m blown away by your patience and tact. When I first read Drew’s letter I had to turn off my computer and seek a diversion to prevent me from dashing off an email that I surely would have later regretted. Just some of the “buzz words” that set me off were his wanting her to “donate” to his “business,””Biggest problem is more cash for expansion, “Maintaining being a good nephew and just smiling,” “Vastly advance my business” to mention just a few.

    When I calmed down and came back to my computer, I then read your response and I once again realized that you not only have wisdom but tact as well. I especially appreciated the part where you mentioned how she could solve “what you see as your greatest problem!!” Exclamation marks added by me. If only that were our biggest problem in business?!

    My advice is that perhaps Drew’s aunt is truly his biggest fan and she probably is really rooting for him to succeed. I’m personally grateful that I wasn’t born with the proverbial spoon in my mouth. Those so afflicted may never know if they could have made it on their own!

    Thanks for your work.

    1. Rabbi Daniel Lapin

      Dear Rich–
      One of the advantages of writing a response over responding in a conversation is that it affords you opportunity to ‘cool down’ and allows you to read and reread your answer, edit and modify until you’re satisfied. We always hope those to whom we respond come back with updates as to how things are going. Perhaps Drew will eventually let us know how this all turned out. Meanwhile, talking of responding in conversation, tonight I am hosting a Q & A conference call at which I will respond to questions on money and marriage. Here are details:–Live-Q-A-with-Rabbi-Lapin—Thursday–6-7.html?soid=1113800665814&aid=6jaaWhHzpBk

    2. Clare Koesters

      I would add “Throwing $20-$40 at me,” to your list. He seems to be taking it as an insult rather than a kindness that his aunt is willing to have him work for him. Also, doesn’t he realize tons of successful people started by mowing lawns, delivering pizzas, etc.?

    3. Clare Koesters

      I was also thinking that she’s his biggest cheerleader and probably has scruples about giving money to relatives.

    4. Rich feel free to tell me how you really feel! I don’t know how else I can relay as perfectly precise a communication to Rabbi Lapin without using the words I did. The English language only has so many options. I never knew “buzz words” could trigger someone so drastically and for that I do apologize! Also, omitted from the question was that “my biggest problem” is a new computer because I work in the 3D graphics field, and some 3D rendering can take me many hours (sometimes overnight) that would otherwise take literally a few minute on a new high end computer. That is what the money would be used for. Anyway, I appreciate your feedback and I do agree with you in regards to my aunts sentiments (check the larger reply I wrote Rabbi Lapin below).

      P.s I would like to hear more about your loathing of “buzz words.” What’s wrong with a very intentional and precise use of language?

    1. Rabbi Daniel Lapin

      Thank you Mees,
      we take no credit other than by trying to be faithful transmitters of ancient Jewish wisdom

    1. Rabbi Daniel Lapin

      Thanks Dan–
      See response to Mees nearby and let me also mention that my wife Susan is every bit as involved in resolving these tough questions as I am.

  8. I know you mentioned Drew’s aunt being a “charitable women” (and lets hope her giving is heart-based).

    But often many wealthy people will give to charity as a means to gain tax credits, or for the accolades or attention that such giving gives — or for other reasons other than wanting to help others.

    (I had been hired many years as a vendor for a very large, world-wide non-profit humanitarian aid group [which l shall not name], and saw many wealthy couples who gave huge amounts each year just so they could rise up within the ranks of the organization.)

    Let’s hope and pray that Drew’s aunt is a much more heart-felt person. But it also is a message to Drew, as well.

    Giving to others is always helpful to the recipient (regardless of the reason it was given)– and Drew should not view those who receive such funds from the Aunt as somehow being unworthy to get such help, or to see such folk as ‘competition’ with the needs of an up-and-coming business venture.
    Both could be blessed by the aunt’s giving — but Drew’s mindset may have to soften or change towards such giving.

    G-d may desire Drew to be more loving towards others (aunt included) before he is able to move on into a business. Because once the business takes off, it will require Drew to interact with the bigger world (other people). And a more giving, loving personality and attitude will always be successful.

    1. Rabbi Daniel Lapin

      Dear Holly–
      It is a very commonly held but mistaken view that a gift given from a loving heart is somehow better than one given thoughtlessly. Through God’s eyes, maybe; we don’t really know. However, from the point of view of the recipient, what is better? $10,000 given by someone who is going to get an equivalent tax benefit or $100 given by a loving and compassionate donor? Whatever is in the heart of his aunt, her giving is charitable and praiseworthy. God alone reserves the right to peer into people’s hearts. He allows us to judge others but only on their actions not on what we think or perceive to be in their hearts. (For this reason, years ago I loudly and insistently criticized the then-pending ‘hate-crime’ legislation. To punish two people differently for the same crime on account of what we believe to have been in their hearts is thoroughly immoral.
      I couldn’t agree more with your final paragraph.

      1. Clare Koesters

        Dear Rabbi Lapin,

        Thank you, thank you, THANK YOU for voicing your view on the irrelevance of the mindset of a giver of charity. I always feel I’m in the minority on this point. Do people think that a homeless person won’t appreciate a warm meal unless the person buying it for them is pure of heart? No – they will still be hungry regardless!

        Best wishes,

  9. This seems like excellent advice in so many ways. You are a very wise man, Rabbi Lapin.

    1. Rabbi Daniel Lapin

      Dear David,
      My wife, Susan, and I are blessed to be the recipients of much ancient Jewish wisdom from some remarkable teachers over the years and this is the source of all we teach.

  10. Carmine Pescatore

    The advice I give younger people is to seek out mentors for advice. It is nice to know which doors are worth opening and which ones to avoid. You gave great advice to him when you mentioned that he should ask his aunt to have her advisors look over his business plan. A win-win plan. He gets impartial advice and she becomes aware of his business plans. Whether or not she invests is her decision. If not then he can ask if he can contact her friends who might be interested. I doubt she has poor friends.

    1. Rabbi Daniel Lapin

      Thanks for writing Carmine-
      But why would you have phrased your last sentence the way you did? I am nonplussed. Why wouldn’t you have said, “I’m sure she has many affluent friends”? The way you wrote it sounds mildly resentful and perhaps a bit churlish. None of us mix socially only with people in our precise economic bracket. I can’t imagine why she wouldn’t have some friends with a lot less than she. Furthermore, the entire point you make is not that she has no poor friends, but that she is bound to know other potential investors. Perhaps I misunderstood you.

  11. Once again, your thoughtful response to the complicated issues of family and money were spot on.

  12. One is immediately struck by your (pl.!) wise advice to allow the aunt in question to develop two separate personas for her nephew: one of (1) nephew and another (2) of businessman. And so I wholeheartedly agree that the likes of Drew need to present to their demanding elder relatives a crash course in ‘Hey Auntie, I am a grown-up businessman, too!’ Also, I am reminded of the behavior of one demanding and CONTROLLING mother I have observed, who always picked on her eldest son, the one with the most crushing family responsibilities. She always picked on him to perform her lawn maintenance or home repairs or errands, and blah blah blah… Sometimes younger relatives can be too good. Too compliant. This eldest son needed to wax assertive and say: ‘Hey Mom, I have a whole family to care for. Why don’t you ask my two younger brothers who have far less responsibility and much more time?’ Self-assertion is another valuable skill to deflect the demands of controlling relatives, to enhance one’s self-preservation and to set boundaries. And surprisingly, often they understand, just had never thought about it in such terms before.

    Then again, as I age, I am also painfully struck by the realization how my parents and some of my parents’ siblings will always-but-always see me as that little boy with soiled diapers, even when I am fifty years old. Even more painfully, I am conscious of how (at times) I myself fail to acknowledge that my own children are grown and have every right to craft and steer their own futures. So with advancing age I am more apt to forgive my elder relatives for the same shortcoming I must now face in myself.

    1. Rabbi Daniel Lapin

      What a charming and interesting letter, James,
      and don’t think we missed the (pl!) in there. We watch you like an eagle.
      We could only nod knowingly as we read your words.

    1. Rabbi Daniel Lapin

      Thanks Sinnie
      and let’s hope that it helps Drew progress towards becoming a mature and successful nephew and entrepreneur.

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