Confessions From A Spoiled Rich Kid

Flying Over San Francisco

Flying Over San Francisco For Fun

The following is a guest post from long-time reader, Samurai Marco.

When Sam first mentioned that he was accepting guest posts from his readers, it made me wonder what, from my financial journey, I could share. After all, you’re already all a bunch of financial samurai’s yourselves, right? Is my journey interesting enough? At 43 years old, have I made enough mistakes?

I grew up a spoiled rich kid in Cupertino, California, about an hour south of San Francisco. My father was a one of those, and I hate to use this term, “Serial entrepreneurs.” He started a lot of technology companies, a couple went public, some were acquired and, of course, a few failed. I remember my Dad, back in the early 80’s, bringing home the first prototypes of the Macintosh and Compaq computers and even the first cell phones.

His summer parties were filled with the “who’s who” of Silicon Valley. I remember, in particular, one Christmas party in 1997, Gil Amelio and Steve Jobs made the deal for Apple to buy NEXT that night at my Dad’s house. The Forbes reporter, who was there, leaked it the next day I’ve gone flying with my Dad and Larry Ellison. I’ve talked stocks in the swimming pool with Eric Schmidt. So yes, I was surrounded by a lot of money and power and got a lot of attention for being my father’s child.

To say I grew up spoiled really is an understatement It’s taken me a long time to realize how “out of touch” my reality was back then. We flew first class to Italy every summer, sometimes twice a year, to visit family. We lived in a big house with a swimming pool in a “safe” neighborhood. My parents bought us whatever we wanted.


My first car was a brand new convertible BMW and I was just seventeen years old. We were members of the tennis club and I took as many lessons as I wanted, whenever I wanted. By the time I was 21, I had a pilot’s license and my own single engine airplane stationed at Santa Ana airport. My dad paid for everything, all my housing and education including a BA in Sociology from UC Irvine and an MBA from Santa Clara University. I never worked in college and, in fact, my dad was giving me a hefty monthly allowance, for as long as I can remember, even after college.

When I left for college in 1988, it was a reality blow. Growing up in a rich kid in Silicon Valley, I realized that not everyone was living as comfortably as I was. People were talking about “debt” and having to “work” one or two jobs, while they were in school. I could not believe that people, in addition to studying for classes and preparing for exams, had to work too?! What kind of life was this!?

My parents were divorced by now. My dad was on his third major company that would add even more millions to his treasure chest. So I did what a rich spoiled college kid does when in college. . . .PARTY!!! I made friends, joined a fraternity, flew around in my plane, drove around in my BMW, experimented with alcohol and drugs and really just had a blast. I got my BA in four years graduating with a 3.35 . .not bad for a spoiled rich kid, huh?


My first two years out of college had nothing to do with working. In fact, I had never really planned to actually work. Instead, I lived in Lake Tahoe for a year in my parent’s house, skiing and studying classical guitar. The second year I backpacked through Europe with a girlfriend. I bet you’re asking, “Your parents just let you do this?” and the answer is yes, I could pretty much do whatever I wanted. Maybe they didn’t know any better or it was their way of showing me love. I really don’t know. Anyway, at the time it was fine with me and yet, looking back, confusing as hell.

In 1994, after studying music in Tahoe and traveling, I moved into my dad’s mansion in Los Gatos and started my MBA. I lived there, rent free, in the maid’s quarters and was paid a fat allowance. I ended up living here for about five years, getting my MBA and eventually getting a job, through a friend of my Dad’s, at a tech PR firm in Redwood City.

In 1995, I took control of my trust fund.  I had no idea what to do with the modest amount of money, as my only experience had been spending it!  Eventually, through the advice of another family member, I started investing in stocks like AOL, Dell and Microsoft.  By April of 2000, five years later, the original amount had multiplied by almost 15 times! The technology bull run had made me a millionaire on paper!  About a month later, that same family member told me the markets were getting sketchy and too volatile and advised me to sell.  Sound familiar?  I hesitated and eventually followed his advice and sold everything.  I took some of the money and bought the condo I still own in San Francisco.

A year later the dot com crash happened and I was the only one my age I knew, other than my brother, with any money. I was thrilled, totally confused, and didn’t know what to do with my life. I fell into a bit of a depression. I was totally burned out. I quit my PR job, left my girlfriend and for the next couple years I was just hanging around SF going to therapy, reading self help books, practicing guitar, playing tennis, and spending time with my brother and his family. I felt unworthy of the money and the extravagant lifestyle I had been living for the past several years.


Fast forward to 2014, and not that much has changed. I’m still bouncing around! I spent the rest of my thirties and early forties trying to figure out what I wanted to do and who I wanted to be. I’ve been experimenting, working for a few years as a tennis instructor and musician for Club Med, almost four years as a live music venue owner in San Francisco, again in tech PR in in Los Angeles, and, most recently, as a restaurant owner in the Dominican Republic.

Would I have ended up like this if I had been raised differently with stricter parents? Probably not and, frankly, we’ll never know, so who cares?! Today, I try to view work more as a form of play. Looking for things that are challenging and push me toward my higher self. Maybe it’s been easier because there’s always been money around . .maybe it’s my personality. Probably a bit of both.

Even so, my forties have been a big slap in the face. All of a sudden you’re not really “young” anymore. You can still occasionally act like an idiot, even though people expect a certain level of maturity from you. This has been hard for me. My whole life, I’ve been able to do whatever I want. Turn on a dime and go in any direction. I’m still trying!

As of today, I’m living in Montreal with my lovely and loving girlfriend of three years, in the process of selling a Punta Cana condo I bought in early 2013, trying to sell a Punta Cana restaurant I bought in late 2013, looking for some kind of stable work, and choosing to have gratitude for how this crazy journey that keeps unfolding before me.

What keeps making me want to work, Sam asks?  Why do I still have some ambition, even though I could probably get by, fairly comfortably, without ever having a job again?  I’m not sure what it is.  Sometimes I think I have too much energy for my own good and just like staying busy.  Maybe I’m trying to outdo my Dad?  I’ve always seen my personal life and business as two sides of the same coin, so whatever I’m doing, if there’s an opportunity to make a buck and secure my future that much more, why not?  It’s also nice to know that I can leave some money and assets behind to the people and causes I love.


1) Get therapy quick!

Seriously, if you’re a narcissist, as I was and still am a bit, fix that as soon as possible. As soon as I “let go” and forgave my past, especially issues with my parents not being there as much as I would have liked them to be, opportunities stared knocking again. If you’re stuck in a “poor me” attitude, whether you’re poor or a billionaire, you’re going to be unhappy and unlucky. I went through a lot of therapy, read a lot of psychology and self help books and began writing daily in a journal. This has saved my life, for sure.

2) Spoil your kids with love, not money. 

I don’t know if it was a generation thing or just my particular experience. For most of my life, I thought that money grew on trees and I could have as much as I wanted whenever I wanted. I had to read and learn so many things for myself. Parents, please teach your kids the value of money and work and, please, place love and nurturing ahead of money. Lead by example by being loving and present with your kids. If you set aside a trust fund, make sure they don’t get it until they are in their 30’s or later. In fact, maybe skip the trust fund!

3) Take a break!

Burn out is normal and, if you don’t take breaks, you will probably not succeed at anything. For some of us, a weekend is enough of a break. For me, sometimes I need a month or a year to let things sink in and start on a new path. Know yourself, your situation, and the amount of time you need before your next big burst of energy.

4) Continuously manage your relationships. 

Geez, this one is so cliche and so important. Money comes from people, not from some robot cash dispenser. If you have a network of people you trust and trust you and your skills, you will be OK. If you go at it alone for too long, you’re going to be in trouble down the road. I’m a bit in this situation right now, as I’ve moved around so much, it’s been hard to nurture relationships, both professional and personal. So, please big shot VC … get back to me!

5) Try not to look back. 

You have to believe that there is exponentially more opportunity in the present moment than there ever has been in your past. Even those big moments you think you missed. . that’s your mind playing tricks on you. Your past, like the present, really is an illusion. Even this post, it’s based on images from my past that I’m choosing to remember and write about. Take a snap shot of your financial situation right now and see if you can make some decisions without letting the past OR the future blind you. I struggle with this every day.

6) Be OK with starting over. 

Could I have had done better financially considering my background, early start and education? Hell yes! You can always have done better. That kind of thinking is a waste of time and energy. There’s always a chance to start again. Remember, the present moment is always 100% pure potential and you can make a decision at any moment that can turn your world around.

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Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship.

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  1. Mike H says

    Great story and thanks for sharing. You sound like you have got your head on straight.

    I’ve never been a fan of therapy though, I think you can sort things out yourself with the proper level of introspection. Getting away to do this is not a bad idea, whether by doing a long day or multi-day hike, or psychedelic drugs in the desert you will eventually find the answers you are looking for from inside.

    Your story reminds me of a Buddhist quote that even rich people go through their own type of suffering and it is not worthwhile to envy anyone else, it is better to feel compassion for others.

    I hope your journey continues to be productive, your philosophy is in alignment with personal growth. As is said, when the student is ready the teacher arrives.


  2. says

    Very cool story!

    My plans for my kids are to help them as much as possible by teaching them how to make money have a great attitude. I don’t think that can be done by buying them cars and giving them as much money as they want. I was not bought any fancy cars or given a monthly stipend in college, but my parents did pay for tuition and room and board at a state college. I worked during the summers and had part time jobs during school for spending money. I also racked up as much credit card debt as I could. Lol.

    After college I couldn’t find a finance degree so I started working for my dad in real estate. That provided enough money to buy a modest house, but I never saved any money trying to follow his system. Then I started making goals and creating my own niche in the market and things took off.

    I really think people need goals and things to shoot for to be successful. Maybe if samurai Marco set some very specific and difficult goals it would help him create some direction and a sense if purpose. I think if you follow some one else’s plan or path, or just drift along without having your own dreams its hard to see a point or be challenged. One reason why I think the corporate world makes it tough to get A head. Your are always chasing and working for someone else’s dream.

  3. says

    What an interesting story. At least you know that you were spoiled and can recognize now how different your upbringing was. Many people don’t! Your life seems so much different than mine, but an adventure nonetheless! I think it’s easy for parents to spoil kids with money instead of love (if they have it) because they think it’s a replacement for time. But it’s not. I can also vouch for therapy — it can do wonders!

  4. Shyla says

    Wow, what a story! Thanks for sharing, Marco. It is really interesting to get a glimpse into this kind of life. Growing up the way you did, do you feel that it was harder to find your life’s purpose? Did your father ever serve as a mentor to you and help shape your path? From your story it sounds like he was really busy and you were off on your own a lot with little life guidance.

    From your story it also sounded like you had access to an abundance of successful people, including your father. Are there any questions you wish you asked them about life when you were in your 20s? Do you still keep in touch with people from your childhood?

    • Marco says

      Hi Shyla – Thanks for reading and asking these questions.

      “Growing up the way you did, do you feel that it was harder to find your life’s purpose?”

      Yes, I would say growing up as spoiled as I was, finding a life purpose or even a stable career has probably been harder than someone with a stricter upbringing. It’s like a dog.. if you don’t train them, they’re all over the place, hard to control, anxious and unable to focus. For many years I was mad at my folks for being so uninvolved in my life. At some point, I accepted the positives and negatives of my upbringing, forgave myself and my parents and began living my life. Now I see my purpose as being loving and grateful, sharing my knowledge, skills and experiences through teaching and ENJOYING life as much as possible.

      “Did your father ever serve as a mentor to you and help shape your path?”

      This is weird because my dad was so successful in the external world of money and power and, at the same time, he was almost invisible at home. It was like he was hiding from the world. Looking back, I think my dad was depressed and never really recovered from the break up with my mom. I feel like, at times, he did try to guide me and for some reason it just didn’t stick. Maybe because our relationship wasn’t strong enough and I didn’t feel like he really cared that much. And I know this sounds like I’m playing victim and I’m absolutely not. I’m just saying that to be a mentor to someone, you have to really take the time and nurture the relationship. My dad wasn’t really around as a “Dad” so I guess it makes sense that he wasn’t really much of a mentor either.

      “From your story it also sounded like you had access to an abundance of successful people, including your father. Are there any questions you wish you asked them about life when you were in your 20s? Do you still keep in touch with people from your childhood?”

      When I was in my 20’s I didn’t really have many questions. I was a nervous dog running around doing what I thought I should be doing. As far as questions I wished I’d asked them back in my 20’s, I really don’t know. I guess I’d ask them more philosophical questions like “What makes you do what you do?” “What’s your definition of success?” “Is your family happy?”

    • says

      Some people take a lifetime to find their life’s purpose.

      I’m not sure what mine is other than to be helpful and do the best I can with what I have. Do you know what yours is?

      • Marco says

        As Tolle recommends, I’ve turned my life purpose inward .. to remain present as much as possible. When you do that, everything tends to take care of itself.

  5. says

    I forgot to add, great point about letting go of the past. Too Perfect is an awesome book about obsessive compulsive behavior and letting go of the past. When we learn to use the past as a learning tool and not regret it is awesome.

  6. Rob says

    Great story… I had a nice lump sum in the nineties as well but like you made sure to get the education (BS,MBA) as a backup. The journal you mention is the single most important therapy you can have IMO. Skip the therapists and minimize the books. We have what we need in our head just dedicate the time. I figured that out in my teens thankfully. I don’t think the money is a problem it really is bring present in your kids lives. I give my kids everything and that includes my time, love, and energy most of all. I don’t force them to be hyper-competitive but instead be true to themselves, us, and others creatively, artistically, technically, critically, and respectfully. Work is necessary but not all-encompassing and certainly not something I would EVER define a life through. It’s just one aspect and in the 5-10 range of priorities. Nurture your relationships #1.

    • Marco says

      Cool Rob – Good to hear from another avid journal keeper. Sometimes I feel guilty because I’ve stopped writing it by hand and now send myself daily “Soul Notes” via email. It’s easier to just write something in the moment and send it to myself than waiting to have my pen and pad ready.

      And yes, totally agree that you cannot, and should not, define yourself through work. After all, what is the definition of work really? Aren’t we always kinda working on something anyway? Sometimes you’re getting paid and sometimes your not. One of my goals, lately, has been, a la Samurai style, to get paid big money for work that I love doing, whenever I want and as often as I want. Right now I’m teaching tennis part time and it has all the qualifications I mention above . .just need to figure out how to raise my hourly rate from $16/hr to $300 .. any ideas anyone?!?

      • says

        You know, I wonder if writing this blog is my form of therapy much akin to your journal writing? It must be quite similar no?

        I’ve been able to get through sorry, disappointment, and fear through writing. I’ve got many posts unpublished, but just being able to write them has helped me tremendously stay level.

        • Marco says

          You’re lucky because your therapy is a part of your livelihood. More and more, that’s the kind of work I’m looking for.

  7. Jon says

    Thanks for sharing your story, Marco. It’s one very few of us are familiar with from personal experience.

    How do you think your life would be different if you had grown up in a $50k a year household?

    • Marco says

      Oh, $50k per year household. Dear lord, it would have been so different I can’t even answer that question. Maybe my parents would have never left Sicily in the first place and never gotten divorced? That would have changed everything, as my Dad, perhaps, wouldn’t have become so obsessed with work to numb the pain and make up for his failed marriage. And maybe, he would have been more present with my brother and I, and taken more time to show us the things that took me fifteen to twenty years longer to learn. Again, I’m not blaming my dad for anything anymore. He did his best with the situation he had and, at least, he killed it financially and all the family benefitted in some way from this.

      I’m pretty sure I would probably have had a more stable and consistent career path. Perhaps I would have stayed in tech PR for the long run and, by today, I’d be a VP of Communications at some agency or corporation pulling in at least $200k. Would I be happier. . I have no idea. Also, I’d probably would have gotten married and had children, as I didn’t see family life, up until recently, as a positive thing.

      I don’t regret it anyway. Your life happens the way it happens for a reason.

  8. says

    Thanks for sharing. When come to terms with your mistakes is when you can actually move on. I grew up with rich successful parents who never gave the appearance of wealth. They brought my brothers and I as if we were poor. Emphasis was on work, values and skills. I got what I needed vs. what I wanted! I received a good formal and informal education and passed it on to my children. I did not value my parent’s strict upbringing at the time, but I turned out okay. I could never get enough of my parent’s time because they were always so busy 24/7. Balance is key in bringing up children. I was successful in my own right and achieved financial freedom (38 years old) without any financial help. I spent a great deal of time developing a relationship with my children. They turned out to be successful adults.

    • Marco says

      Wow, being raised by busy rich parents who taught you the value of money and somehow made you feel loved in the process. That must have been an amazing experience. Lucky you and lucky your children!

      • greg says

        Sometimes I wonder about nature vs. nurture. While I had a lot of privileges (not crazy wealth, but eventually good parental income), to this day I always save and invest more than my parents and have a completely different outlook.

        While I didn’t really get much and had to live for a while on a tiny allowance in Manhattan, I’ve been naturally frugal and constantly evolving. I can trace those tendencies WAY back into my childhood without any apparent cause …

        • says

          Nature or nurture is not an either or statement! I think both contribute to who we become. I was always interested in business and money, but I was always around my entrepreneur parents. I worked for them (reluctantly) from as early as 5 years old every weekend. If my parents were something else, would I have the skills and interest to do something else? Who knows!

  9. says

    Thanks for sharing. I really appreciate you being willing to talk about getting therapy. Two different times in my life I’ve gone to a few therapy sessions, and found that an outsider can really help put things in perspective. I recommend it to anyone struggling with ANYTHING.

    Also, I think you had two really really good pieces of advice. 1. Forgiving myself and my past were critical to my current happiness, so I can relate to you there. 2. Accepting that you need to start over is huge. Too many people I know cling to what they had, instead of accepting that things have changed and they need to move on.

    Again, great story and thanks for sharing

    • Marco says

      Thanks Brian. A big part of why I went into therapy was I was driving family members crazy with my anxiety and insecurities about everything. I noticed when I had someone else to talk with, I was able to be more present with them and focus more on their problems instead of mine.

  10. says

    Thank you for sharing your story that can be the toughest part of writing just putting yourself out there.

    I’m going to skip over the this is how I lived like a Kardashian reality piece that covers 3/4 of the post. I lost interest after getting through this, the part where you purchased a restaurant or a condo and are working on selling it would have been interesting, but studying guitar while living in the maid’s quarters or Dad’s mansion lost me again. This was the best I could do at being positive, I think I have a Napoleon’s complex for rich kids, does that exist?

    • Marco says

      Rich kids, poor kids, whatever. . we were all just kids at some point and all we really needed was our parents love and guidance. Spoiled acting kids drive me nuts and, for some reason, there is always a clueless arrogant parent nearby to put fuel in the flames.

      • Ralph says

        Marco, you really nailed it with this comment. What impresses me about you is your humility despite coming from a privileged background.

        • says

          I agree. I’ve blocked a couple pretty nasty comments. Not sure why people want to hate on someone who made a confession. Confessions are all about listening, accepting, forgiving, learning, and moving on.

          We all have our flaws. It’s what we do with them that matters.

  11. says

    Thank goodness for the advice of your family member and thank goodness you listened!

    You also give some really great tips that aren’t usually on personal finance blogs – getting therapy is the one that stands out the most. I’ve done therapy years ago but it might be time to admit some if my financial issues are tied up in very emotional matters.

    • Marco says

      I agree. Any financial issue you have is almost always traceable back to an emotional issue.

      Suze Orman is big on this and I’ve learned a lot listening to her podcasts.

  12. amory says

    I’ve long found this blog to be an interesting read for practical advice on managing and accumulating money. This story, while interesting, is misplaced here. Advice from the super wealthy I want? how to develop a relationship with a person who can help time the market. Advice I don’t want? How to raise my kids and get therapy.

  13. Austin says

    I’ve spent a lot of time thinking about things like this; my sister would call it “trustifarian”. When money is less of a concern you begin to look for a deeper meaning and drive. This often results in some kind of existential crises. My personal value system is very different and I just can’t empathize with someone who is overeducated, has the ability/funds/connections but lacks the drive. I would always be out there trying and doing. Even if I fail time after time. But, that’s just me. I know plenty of people like you and it just doesn’t compute for me.

    • says

      We all grow up in different ways. If all you knew was growing up rich around fellow rich people, would you really feel that rich? I doubt it.

      It’s very hard to motivate yourself sometimes when you don’t have to do a thing.

  14. JasonM11 says

    Sorry but this seems to be a sad tale of a wasted life so far.
    Living off others, even if they are family, for so long could not be very fulfilling.
    A spoiled rich kid is not funny…just spoiled.

    • says

      Not sure that this post was meant to be funny, but a confession of the way things were and Marco’s introspection and guidance for others who might be in his same situation. Takes courage to put yourself out there.

      If you’d like to give it a go, let me know.

    • Sundeep says

      I would agree that I hate spoiled rich kids, and part of that is probably some jealousy mixed in, but I think with Marco, that he’s seen that he was that way and is trying to live his life in a more fulfilling way is admirable.

      I agree with Sam and some others in that if you’ve only know the “rich” life, how can we condemn that person if they truly have never seen the struggle most of us face…it’s all perspective I guess.

      A lot of folks are commenting that Marco “wasted” his life which comes across as a little petty/jealous, but I also wonder how his life was wasted if he got a degree in college, and MBA, made some money in the stock market, dabbled in real estate and restaurants, learned how to fly a plane, learned and is teaching tennis, and become a decent guitar player? I was reading those thinking I’d like to do some of those things when I become FI…? Am I missing something? I think the tone in which Marco wrote his story as a guy trying to figure stuff out, comes across like he wasted his life, when if you look at the things he has done to date, it’s not so bad. He’s only in his 40’s as well, still a lot of life to life yet.

      Thanks Sam and Marco for sharing this story…

      • Marco says

        Thanks Sundeep. My intention was to show people that growing up as a spoiled rich kid, as fun as it can be at times, is not necessarily that fulfilling. And, in fact, it’s not growing up rich that’s the problem, it’s the spoiled part.

        As for a “wasted life”, I don’t know what that means. I’d just be careful if you’re muttering those words, as I’m a big believer in the “spot it, got it” philosophy.

  15. says

    Each human condition has is own disadvantages and advantages.
    But what is good, is that there are alwasys lessons to learn and steps to take to improve.
    Thank you for sharing your story, Samurai Marco.

  16. says

    Marco, thanks for sharing your story – it takes courage to get out there and share everything like you did. I love how open and honest you were about your situation. It was very interesting to hear you talk about how weird it was to see others who had to work hard and struggle with money and debt.

    To me, one of my biggest fascinations is why some people are born into money and others not. Is there something predestined about it or not? I really appreciate you sharing your story. I’m learning from people like you and Sam. I’ve made great strides in my money, but have a long ways to go.

    I grew up comfortable – always had a house, food, most of the basics covered. That trend continues on to this day and I’m thankful for it. Thanks again for sharing.

    • Marco says

      Thanks for the encouraging words Jeremy. I don’t know why some people are born into money and some are not. Like most things in life, it’s all a mystery. We all come from such different backgrounds, upbringings and genetic predispositions. I shared my story to reveal one, unique situation and because I enjoy writing. I’m sure that your story and anyone else’s on this blog can be just as interesting. It all depends on the point of view.

  17. says

    Thanks for sharing! It’s always interesting to hear the stories of people with very different backgrounds than most of us grew up with. I agree that rich parents should try to avoid showering their kids with money. It’s a shame to see kids with all the resources and opportunities they could want in life lose any drive or motivation because their parents always handed them anything they wanted.

  18. Money Beagle says

    One of the first shows I ever started watching with my now-wife was (don’t judge me), The OC. And, i would always watch it wondering just how these people didn’t see at all how the ‘rest of the world’ lived and was it for real. Your post kind of answered that. You know what you know, I guess.

    Thanks for sharing. Very interesting perspectives and it’s always thought provoking to get different world views.

  19. BH says

    Great story. Thanks for sharing. It’s nice to hear you learned to focus on what matters most – relationships! I have the opposite situation – my parents did well (but not nearly as well as yours) – paid for school and grad school, but that was the end of it. Now they even expect me to buy whenever we eat out, even though they are in a much better position to pick up the check.

  20. says

    Hi Marco,

    Thanks again for sharing your story. I’m just wondering several things:

    * If you grew up poor, and then your parents became as rich as they were, do you think you would be happier and appreciate your wealth more? It’s my belief that if all you do is go on vacation, vacation no longer becomes as fun. Work and progress makes us appreciate our vacations more, for example.

    * I’m assuming despite it all, you are still very wealthy with your trust fund intact no? If this is the case, what gets you motivated to work hard if you don’t really have to?

    * If you have kids, how would you tell them about their trust fund if ever?

    * At what income level do you think you need to make in the Bay Area where happiness goes no further? My theory is $200,000 per person, and I’d love to hear yours!



    • Marco says

      Hi Sam!

      Thanks for the questions.

      If I’d grown up poor and my parents became rich later in life, I’m sure my financial situation would be much different. Perhaps, due to a better work ethic, I’d probably have a more stable income, a more stable career and who knows what my net worth would be. In that situation, whatever wealth I would have accumulated, I’d probably appreciate it more, due to the fact that I would have really worked my ass off to get there and probably without a lot of help from my folks. Not saying that I don’t appreciate what I have today as, in my own way, I have worked my ass off by educating myself, minimizing my spending and maximizing my passive rental and stock/bond income. And yet, like you said, there’s nothing more satisfying than earning active income. I make $16 an hour teaching tennis right now and I’m still giddy when I get my checks!

      Yes, I would still consider myself relatively wealthy, considering I own my SF condo in the clear and still have a good amount of liquid stocks/bond/cash on hand. However, in San Francisco terms, I wouldn’t say I’m that rich. That’s why I don’t live there anymore. I’m trying to make what I have work for me in a lower priced area with a good quality of life. I pay $1300 Canadian a month for rent in Montreal that would cost probably around $3500+ in SF.

      What motivates me to work hard?
      Enjoying it. It has to be fun and fulfilling or, at some point, I will lose interest, not matter how much it pays. Maybe that’s the spoiled kid in me? Is that so bad?

      I don’t have kids and I don’t think I’d leave them a trust fund. It’s too weird for me now. I’d leave them property in their name or give them some lump sum while I was alive, assuming they were already working and not insane drug addicts.

      Ideal income in SF? Even at $200,000 with rent and lifestyle prices where they are right now, I’m not sure all these techies are saving as much as we think. Given that, I agree that, if you’re smart about it, $200,000 should be more than enough to live comfortably in any major U.S. city. In the end, I don’t think your salary is that important. It’s way more about your attitude, social skills, flexibility and your saving and spending habits.

      • Ricky says

        In no way am I projecting pity but I find it a little troublesome to believe that you started out with sky’s the limit and now must budget – to an extent?

        You kind of skipped over the part where you made so much money in the late 90’s through successful stock trades and bought the condo and now are worth what sounds like pennies on the dollar compared to what could of been had you managed it all. Did the extensive breaks drain you that fast?

        I’m only curious since I just can’t fathom the lack of inquisition from yourself as a 20 something.

        • Marco says

          I’ve never been “the skies the limit” rich and even if I was, I’d still budget.

          Lack of inquisition as a 20 something sounds about right.

  21. G says

    Too much or too little of everything is always a problem. It is about balance and sounds like you struggled alot seeking that. Thank you for sharing your experience, and your suggestions.

  22. Frank says

    Hi Marco,
    Thanks for sharing.
    It is quite insightful. Yes, this is a blog for the super frual.
    It doesn’t chance the fact that yes, some people do in fact “make it”, and it’s interesting to think of what happens when that does happen.

    I’ve always wondered how one should handle the situation of being wealthy, especially since I’m not particularly materialistic.

    I don’t see any point in dying with millions of dollars in the bank.
    I also don’t think it’s healthy to just unload millions of dollars on your kids.
    Would they know how to handle that, or blow it like some lottery winners?
    However I also don’t think it’s necessarily good to buy millions of dollars of stuff and raise your kids in that sort of ‘abnormal’ environment.

    So how should wealth be handled?

    I wonder, given your experiences, how you personally would handle wealth?
    Or, taking the same question a different way, how would you have preferred your parents handle their wealth?

    For example, would you have preferred (in the long run) not having an allowance?
    Or just a signifigantly smaller once, so you at least have to consider what’s ‘worth it’ or not? Or would it have angered you that your parents had so much money, and aren’t sharing it?
    I don’t think it’s realistic for your parents to try to hide/pretend they aren’t wealthy – I think it’s normal for rich people to at least spend a small portion of their wealth.

    – Frank

    • says

      Frank, do you really see this as a “super frugal” blog? If so, I’d love to get some examples of posts that have that point of view.

      I’m always curious to understand how others view this site, and whether it jives with how I view my site. thx

      • Ricky says

        Some of your posts are borderline frugal. Especially the 10% car rule. I much prefer when you stick to posts like “Avg Net Worth for Above Avg Person”. In fact that’s the post that brought me to your blog.

    • Marco says

      I would not have changed anything about how I grew up financially. I just wish my parents had taught me the value of money and hard work earlier in life. Perhaps they didn’t because they didn’t have those values either. After all, my dad arrived in Silicon Valley in the 70’s and partook in the largest bull run mankind has ever seen. Maybe money ended up being too easy for him as well?

  23. JayCeezy says

    Marco, really appreciate your honest self-awareness, and telling your story. fwiw, please don’t be so hard on yourself. While your life may have been different from most, everybody has the same struggles with finding meaning, embracing responsibility, and the impermanence of relationships.

    One thought on self-discovery through talk-therapy and books…they can have great value, but sometimes people take refuge in ‘seeking a reason’, and, in doing so, mistake the ‘seeking’ for ‘action.’ Not saying this is your case, but some people continue to read books instead of acting to change, and this continues a form of narcissism. I admire anyone who desires to change and improve, and wish you continued success on your journey.

  24. says

    This is such a fascinating story. Teaching kids to work at a young age makes a huge difference! I remember going to school with some rich kids who never had to work through college, and once graduation came around – they had absolutely no idea what to do with themselves.

  25. Allen says

    Hi Sam,

    I absolutely love your blog…and thoroughly enjoyed this post.

    On a separate topic, I’m wondering if you’ve written about life insurance policies in the past. If not, I’d love to see a post on the topic, and how it plays into responsible personal finance.


  26. Ralph says

    Marco, I have a question. What is your relationship with your parents like now? Are they people that you’d go to for advice on anything?

    • Marco says

      Hi Ralph – Thanks for the question. I don’t go much to my parents for advice anymore. In fact, for some things, like investing, I will often do the opposite of what they would do. I know it sounds harsh and it’s actually nothing against their judgement. Perhaps it’s a generation thing. I just find that many baby boomers still make financial decisions based on fear and greed. I’m trying to make decisions that are more in line with my personal values, such as simplicity, freedom, joy and love.

  27. says


    I spend much of my typical day observing my reactions to people and events, and trying not to judge them based on my values.

    That said, I feel sorry for the writer. It sounds like a nice life on the surface – all the money you could want, not having to work, bouncing around without too many responsibilities – but then I think about the moments wasted, the opportunities lost, and it just makes me sad. I admit I’m projecting my values on someone else, and presumably the author is happy with his life, but I have to say, I’m glad to be living mine instead, even with, or perhaps because of, the various difficulties I’ve faced and overcome.

    • says

      I think if you ask most people, they would say they’d much rather be living their own lives instead. Don’t feel sorry for Marco, as I’m sure he’s not feeling sorry for himself.

    • Ricky says

      We are all humans. At the end of the day it doesn’t really matter how we live our day to day lives as long as we are happy during those days. Happiness doesn’t come in one shade.

      I kind of sense you’re trying to justify your own values by saying you feel sorry for him. In no way would I feel sorry for him or anyone else for their financial situation. We’re all human and we all have our own struggles, big or small. Even small struggles to some are big to others. “Meaningless” struggles Marco might have would probably be frivolous to you. It doesn’t mean they aren’t profound and impactful to him. And vice versa.

  28. says

    Very interesting read and nice to hear the perspective coming from a privileged background. My first reaction is that we would have nothing in common. On the other hand, you have humbled yourself in your writing that I think we could have a meaningful conversation. I’d love to know if you have any plans for philanthropy in the future.

  29. JW says

    You bought a restaurant in late 2013 and in mid 2014 you’re trying to sell it? Why not try to make it work?

    You mentioned “maybe you were trying to out-do your dad” but it seems like you don’t stick to something long enough to find success in it. Obviously I don’t know anything more than what you’ve shared, it sounds like your dad was very, very productive but may he was focused on the business thing.

    Do you think if you didn’t have the money you’d be more prone to focus in on on or a few things or would you still have the tendency to go whatever way the wind was blowing you?

    If I had the kind of money you seem to have and was single I’d be a flight risk. I’d just roam around the world, modestly, almost backpacking. To me that would be ultimate freedom…and having a my pretty lady with me would make it paradise every day.

    Sounds like you’ve had a fun life, cheers to making it a long one…for all of us!

  30. says

    I enjoyed reading your story. How fascinating how life unfolds in so many different ways. I can imagine wishing you could have spent more time with your parents growing up. Very successful business people tend to work a lot of hours and get absorbed into projects that require a lot of focus.

    But I think everyone wishes things were different in their childhood, nothing can ever be perfect. And what’s more important is focusing on now, letting go of “what ifs” and grudges, and making the most of our lives.

    Thanks for sharing your story with us!

  31. franklinb says

    Thanks for writing this up and sharing your experience. Sounds like you had a great time, and decided to make some different choices. Thank goodness your mentor stepped in and provided some critical guidance at the right time. (that was your “Moonlight Graham moment). We all can look back a few times and wished we had not wasted valuable time on trivial things. I sure can’t fathom the thought of wasting 40 years of my life as in your case.

    You have an unfinished life and plenty of time to create a lasting legacy and contribution through other people that cash cannot fund. Cash and toys are commodities, Time on this planet is not.

  32. DIMA says

    I really don’t understand these confessions and never will. Kudos of course for realizing whatever you realized but if I had kids and family and was a millionaire-billionaire, I wouldn’t teach them about any of that. What’s the point? Killing yourself by barely making ends meet? What the hell is the value of money anyways? Its all in your mind and in fact it has no value so there is nothing really to teach. If you have millions or billions, just spend it all away! You only live once, life is futile anyways and its a pointless zero-sum game.

    Your kids would do whatever they want with the money you left them (as much as possible, and not the scraps billionaires are planning to leave their progeny) and all this talk about love, social skills, flexibility, bla bla is just that – TALK. Verbal diarrhea that has nothing to do with the real world.

    Over the billions of years life had been on this little planet, we had absolutely ZERO effect on anything in the universe so what hubris it is to assume that suddenly all of these microscopic life journeys on a little rock that formed accidentally from star-dust would in any way matter at all whether they’re poor or rich.

    If you’re extremely wealthy, just spend it all and let your kids enjoy life to the max without having to work a single day for it. What is work after all? Its slavery and how is slavery perpetuated? Daily through births and capitalism.

    Stop bringing kids into this mad world. Let’s just end the human race and this futile pursuit of greed, power and syrupy confessions. No offence.

    • jay says

      Wow, really? You sound like you have no hope on humanity.

      cheer up, and look at things in a positive way, instead of everything doom and gloom.

  33. Jason says

    Sam, I must say I’m disappointed in this choice of article. It seems that you just posted it with no other purpose than to be inflammatory and sensationalist.

    • says

      I’m open to new perspectives Jason. And id love to have yours too on money. You think you can share an article about your learnings with me so I can publish here?

      This is one of the best ways to get through disappointment. To show others how things are supposed to be with your writing.

  34. Jay says

    Hi Marco,
    Thanks for sharing your story.

    You mentioned that you have a brother, I wonder if your brother went through the same thing as you? I asked because I wonder if own personality has anything to do with the things you do in life, even if brought up the same way.

    Rich or poor, everyone has their own struggles in life.

    • Marco says

      Hi Jay – This is a good question and my brother and I have talked about it. We definitely ended up living different lives. He met his current wife when he was fifteen and is now married with two amazing children, with a solid job, living in Marin in a nice home. The turmoil of my parent’s divorce when we were very young affected us differently. In a way, it caused him to settle down with one person very early in his life. It had the opposite effect on me, where I’ve been single almost my whole life, bouncing around, and just recently have gotten into a long term relationship. As for the money part, we’re also very different. I think I ended up more conservative than him. He’s always been financially very savvy and amazing with numbers.

  35. JLewis says

    I hate rich kids. No, that’s not right. I hate poor kids. No, that’s not it either. What I really hate is ignorant adults. No, I try to love people even if I don’t like them or feel sorry for their limitations. Does a rich kid any more elect to be rich, than a poor kid elects to be poor? Do those herein who’ve expressed not being able to relate to the “rich” have a patent on the inability to relate to those they’ve never been alike. Those who have written on this post as “normal” or “poor” kids, are all considered arrogant, wealthy Americans by the majority in this world. How does that feel? Can we change it? Would you give up what you have? I’d love to know your thoughts considering your certainty about so much. Please share something thoughtful. Just not liking someone unlike yourself. Isn’t that being spoiled in and of itself, too? Love and listen – genuinely. Then, we will have something to add to the world. Be able to listen, it is how we all learn about those unlike ourselves and avoid repeating history. Love, me

  36. Young Werther says

    After reading the comments to this post, I felt like I had read a different story. This guy is a rich kid by birth. His narcissistic tendencies are seeking approval of others by posting about his new found love of tough work such as selling a condo and restaurant he bought with trust fund money. He still is frat boy, albeit with a tenuous grasp of the reality that for most people it is just plain hard to pay for college, while he had a plane and played hard his whole life.

  37. steve varga says

    Why work? A sense of purpose. I remember thinking those multimillion Nigerian scam emails were actually true but didn’t reply. Now got that it was a scam. Even though it was in my mind real I said I have to work I can’t just take the easy way out, would be boring, and deadly. Was making a $4.25 an hour at that point cleaning bathrooms. Doing a bit better now 20 years later.

  38. says

    Wow, first world problem. :) It sounds like you’re doing quite well and are happy with life in general so that’s great. It’s good to know the rich have their struggles too.

    Anyway, thanks for sharing your story. Everyone has to find their own happiness. It’s not easy for rich people either. Money makes things easier, but happiness is still elusive and you need to work at it.

    • Marco says

      Thanks Joe. Yes, it’s true that everyone has their struggles, regardless of their financial situation. If you don’t have money, you’re trying to get some. If you have money, you’re trying to figure out what to do with it. Either way, it seems we all tend to get a bit too caught up in it. I was happy to see your comment, as I really enjoy reading your blog.

      • says

        Marco are you still in Montreal? I would like to connect with you re a possible opportunity in your field of expertise – tech PR. Someone had asked me to keep an eye out for senior folks in Montreal. Are you up for a call?

  39. says

    I love your post for your honesty. I grew up in a $45k household with a single mom trying to feed three kids and make ends meet. She literally never had any money in the bank when we were children. For me and my siblings, the age we were when our parents divorced also had a lasting impact on us, as our different personal natures did. How my mom made little luxuries and family traditions so special to us, and celebrated our childhoods, also had a lasting impact on us. How much money we didn’t have growing up was actually pretty irrelevant. We never talk about growing up poor or think of our lives or childhoods in that way because she made sure that we never wanted for anything. She is a super frugal miracle worker. I have two degrees because of a fierce expectation she set on me around the importance of getting an education, especially as a woman (she has no formal education). I’m working on getting my financial head on straight but I think it’s connected more to my nature and susceptibility to our consumerist culture…I struggle to make the daily sacrifices that she made. Of course money is important, but it you stripped that out of your story, as you pointed out in the end, it’s all of the other things that matter more. Thank you for sharing your story.

  40. says

    Its hard to find a truthfully personal post like this one. The story is a bit on the sad side, but the ending points really express great advice for anyone facing life issues. I feel many people are struggling with, a finding yourself mentality now a days. I believe our society plays a role in this, and our ability to learn or grow as well. Thanks for the story Marco best of luck.

  41. JR says

    Hi Marco,
    thanks very much for your post. It was very instructive and illuminating. Also welcome in our nice city of Montreal from a lifelong MTLer. I had my son’s 4th birthday this week-end and because of a recent divorce we only had his cousin come over and played in a park and sang him happy birthday and ate cake. That’s compared to the all out party of the last two years. Now I’m feeling ok about doing it low key like that. Thanks to you.

  42. ISneed says

    Marco, Thank you for such an insightful and honest post!. I appreciate your journey and your willingness to share with us your life’s lessons. Your experience was certainly not my experience, but I can relate to the points about trying to find yourself and your purpose upon this Earth. In this society of dog eat dog type behaviors, materialism and greed; it’s often a challenge to stay focused enough to carve out your own little niche/path. I struggle with this daily, as well as, forgiving myself for past mistakes ( financial & otherwise) so it helps to see there are others out there who can relate.. Keep your head up, Do You & let the haters do what they do best…HATE ( lol) & continue your evolution. Be Blessed!

  43. says

    I know this sounds cliche, but I think this post helps reiterate the notion that true fulfillment comes from having less, not more. When you have to earn every break, or bonus, or opportunity, you wind up looking forward with relish to whatever you are treating yourself to. The smallest things can bring the greatest joy if your life is well balanced. From the middle class point of view, that ten days you spend in Paris after three years of saving up is magic, as opposed to just ordinary if you can go whenever you want. Paying for flying lessons after saving for five years is a much grander reward than being able to take lessons because you have an itch and follow it up with owning your own airplane. I have nothing against wealth or the so-called one percent – these riches are what keep us ambitious and without ambition our society dies. But having unobstructed access to whatever you want will reduce your life to trivialities. Conflict and challenge are essential to bring the stark relief we need to experience joy and contentment.

  44. Fratboy says

    Great story Marco. Although my Dad wasn’t as well off and I had fewer toys, it feels very familiar to me. I had a private school life followed by years at college partying while driving a company car and having a salary by Dad’s company. Today I wrestle with several decisions I wish I made – law school, career – and strive to move on. Currently I am also re-starting and this article was a great reality check and therapeutic.

    PS – welcome to Canada

  45. Gala says

    Wow, you nerds think 45,000 yearly income is chump change huh? Whoa, stop the presses. I’m over 50, worked my entire life BY CHOICE, had many good careers in different areas and loved every job I ever had. I never made over 100,000 annual income, but I had something money can’t buy, true friends, a supportive and loving family, true happiness and faith and I’ve always loved people and life and always will. Here’s the deal kiddies, one can and does live WELL on 45,000 annual income, you just gotta do it right. Oh and please remember in the 21st century, we don’t all need huge homes either. Big spaces are not where its at, it’s being HAPPY with the space you have and making the most of it. Peace out people. Universal love for our planet and all the life on it is where it’s at -go EARN that with money, but that’s not how that works either. Money is superficial and so are many of you. I feel sorry for some of you people too. Get your head and your spirituality in check before you leave this world.

    • says

      Don’t think wanting to earn more is a bad thing.

      If you have a choice, why not shoot for a higher income than a lower income?

      I’ve found only the poor or super rich say money doesn’t buy happiness. Funny isn’t it?

  46. Anonymous says

    I grew up in a home which struggled a lot financially. I would give anything to have been born rich. You’re very lucky.

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