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.

Recommendation To Build & MAINTAIN Wealth

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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. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

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  1. Job Aya says

    Hey Samurai Marco,

    I think I can help you find answers about life. Also I got questions for you about culture.
    hit me up. Like most people said above, nice post. I agree burn outs are normal, people need to know this. Also, as an adult having to limit our silly you can be can be a bit annoying, but its needed to properly parent children and conduct business.

    • Job Aya says

      correction: “Also, as an adult having to limit our silliness can be a bit annoying, but its need to properly parent children and conduct business.”

  2. Jay says

    I’m 25 and in a similar boat…wealthy but can’t keep a long-term project. A lot of bouncing around could reflect borderline ADHD. Since your dad was a serial entrepreneur, you may have inherited this ADHD trait. Google “Explorer’s gene.” Essentially our brains have to move on to something new (innovation) or else we get bored. The downside is we can’t hold down one project. I have found satisfaction in becoming a full-time investor…love to find new companies to invest in. Finally, you need to find your natural talents at an organization like JOCRF. If you use all your natural-born talents, you are more likely to enjoy whatever project you partake.

    • Marco says

      Hi Jay – thanks for the comment. I agree with you that it’s all about finding and using our natural born talents. I like to call these our “gifts” and we all have them. It’s part of being human. Lately, I’ve been exploring my gifts via a life coach and I’m discovering some amazing things. My calling is to be open and free and to share my creativity with the world. You’re right about my “explorer” tendencies, as that theme continuously comes up as well. Good for you that you’ve found your calling through investing. Any hot tips!? I have a company I’m preparing to present to the angel community. Let me know if you’re interested. Sam, you too!

  3. Ann says

    Wow…That was a DEEP story. Thanks for sharing. I actually found this site because I wanted to search for elite kids of San Francisco and maybe find things in the City that I would be able to have my kids experience. It’s really rare to be brought up in such luxury.

    I had my time in my early 20s when I felt I had so much money, I just didn’t know what to do with it. I treated friends out, parents out, Myself out, bought all the material things I wanted and gave to my parents as well but still felt a sense of emptiness…

    Later, I lost it ALL…and I really just took it all for granted.

    Fast Forward…I started over again and started saving money…I felt I was doing everything right—-volunteering, had a great steady job, started traveling, basically what I thought was success…Modesty aside, It also was not hard for me to get dates.

    I didn’t know what I was doing wrong or why I was feeling empty STILL…

    This may sound so CLICHE….So I did something that I would have not thought I’d do….’

    I PRAYED for God to come into my life and mind you—I usually base everything on logic and science…But I decided one day, Let me dedicate myself and read the bible just for a month (just myself in the privacy of my own room) and in return maybe I’ll find what it is that every God believing person seemed to find—Happiness.

    I KID YOU NOT….In one month—So much has happened that changed my life in positive ways…I was also and still am a reader of inspirational and self help books, but nothing has changed my life until God came into it.

    Maybe the same can be done for you.

  4. Yerdanos Asmelash says

    Hey Marco,

    Your post is surprisingly interesting, just because we are on totally opposite ends of the spectrum. I often try to understand the point of views a lot of people similar to you have because they are intriguing.

    Let me tell you a bit about myself:

    Despite the fact that I came from a low-income home, eating ramen noodles and drinking tap water,

    I am in college now. and thankfully, I am pretty caught up… I’m working my ass off to become a doctor…caring and serving others is my dream…the sense of happiness I got from encouraging an illiterate patient to learn how to use the computer to go for that desk job she always dreamed of…to making fun of myself to a visitor of how embarrassing it is that I kept getting lost when directing him to his daughter that just got out of surgery, just to relieve his stress (his daughter was beaten) is what I strive to do through medicine.

    but it seems that all odds are against me to make it happen. I’m not even sure I can even imagine some of the luxuries you described in your post if they are not similar to what I see on television. Flying to Italy is a dream I will soon make happen while on a studying abroad opportunity that I am working on funding. :)

    What led me to this post was actually an encounter I had as a new volunteer at a local hospital this morning.

    I frequently got asked why I was volunteering and if it was for a credit. A lot of the volunteers are old with nothing to do – so they like to volunteer and all. But surprisingly I met a young boy my age who was also working to be a doctor. He had similar experiences as you (I wouldn’t say to your extent but you get the point..). Just by conversation I can tell everything came easy for him. His grandmother looks for and applies for all of his scholarships to pay off his tuition while he gives her essays he’d like her to include, his mother owns a huge company that refurbishes/renovates buildings, his uncle is the chief of surgery at a hospital I one day dream of working at, and so on… This blew my mind because I search 2+ hours a day and come up with nothing for scholarships to ensure my place to live and food to eat, my family is poor so it’s extremely hard for me to network (I have to pretty much chase down every employer for an opportunity hahaha), and not to mention, I’m crazy in debt already…

    You can imagine all he really has left to do though is study and apply to medical school. Which is a bit aggravating but…

    The worst part is that he is the most non genuine person I’ve ever met as far as caring about the needs of others…which is contradicting to the profession he wants. But one thing is for sure-he will definitely reach his goals…But it hurts to think about my passion of relieving the pain of others may not be fulfilled through the practice of medicine, just because I am poor with many obstacles to face, despite my amazing ability to think.

    I appreciate being able to read your confessions, it was really insightful and I wish more people rose and spoke up about their life styles. I can imagine you may have received hate from those who aren’t so lucky with money but I’ve wanted to learn more through actual contact with those like you. There’s a free flowing, positive, life-loving nature that I appreciate within people of higher classes. Most of all, I’ve always wanted a mentor of higher class…I feel like you are one of many who’s side I have yet to learn from. :)

    if you ever want something to do, give back, not through charities, but through one on one relationships.. The feeling of gratitude a person feels when receiving opportunity because of you will damn near make you cry. & That might be where your passion lies.

    -Signed, Yerdanos, 20 yrs old.

    I’m sorry this was so long, but hopefully it was an interesting read!

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