What’s It Like To Be From An Extremely Wealthy Family

How much is your family worth?

Around $500 million

Where does the family money come from?

My father made all of the money. It was more of a right place at the right time kind of situation. He joined a small firm 24 years ago and it has since grown to an international scale (management consulting).

He is an incredibly gritty guy and quickly became an expert in his field (retail). growing up he was rarely around the house, traveling at least four days a week and working far into the night every day. The churn rate at a firm like his is insane and shows his work ethic.

On top of this he has had many large investments return sizable growth over the years. Several of his friends from undergrad and business school started their own companies and have become very successful after my father invested.

He was not poor growing up but was lower middle class and so was my mom. The scale of our wealth as of recently has come from him sitting on the boards of many large and successful companies. He plans to retire soon but will work on the boards of these companies until he dies. He loves what he does and is an absolute family man.

Lastly and most importantly, we only spend money on the things we need, minus our fairly sizable house. Our style of living has not changed since I was a kid, always living comfortably but never flaunting wealth.

Our nicest car is an acura tlx and we never buy expensive clothes or anything. This unchanged lifestyle is the reason for this rapid accumulation of wealth. My dad always says, “you never know anyones financial situation. They might drive expensive cars, have a jet and a few beach houses and be deep in debt.” On the flip side we only own 3 sub-$50k cars and one home.

Have your parents ever claimed to be “middle class” or have you ever thought yourself that you “weren’t rich”?

Yes! My parents would always say we were upper middle class, and would downplay our wealth constantly. I think they did it to keep us humble and to not draw too much attention.

Did you attend private schools when you were younger?

I attended private school K through 12 and also think that it was one of the most valuable experiences I have ever been afforded. The resource gap between public and private is much larger than you would think

Do you have a job, and if so, do you have to have one, or if you wanted to just relax and enjoy life would your parents financially support you?

I have started 3 small companies all in the hardware tech scene. I was always told from childhood that regardless of what I wanted to do I would be supported. That meant I could be an artist, a teacher or any other lower paying profession without fear of financial stability. I appreciated it but it made me feel like a freeloader if I didn’t do something BIG.

They certainly would not support me if I was not actively working, in school, or doing something “productive” for society.

Did your family give you the initial money to start the companies?

My first company, yes. I needed $1,300 to make an LLC, set up my site, get equipment, and talk to lawyers. After that the business ran itself for 7 years and was a source of constant passive income.

About 11k later I invested back into myself and bought a 3d printer, new computer, and software licenses to start selling custom 3D printed airsoft parts, fidget spinners, and other novelty items locally and online.

After that I reinvested again and started selling custom bike parts. Lastly I raised 60k (from friends and family) to start a C corp developing high performance electric motorcycles. We had 11 employees, took on more investors and then pumped the brakes. Now I’m looking to sell it to a larger company and begin work as an automotive/hardware focused product developer.

What is the most unexpected thing that was normal for you, but highly unusual to most people?

Vacations. My family traveled a ton when I was a kid and I just assumed that everyone else did too. Every spring break, winter break, and summer we had elaborate trips planned (spain, galapagos, dominican republic, etc.) and I just assumed everyone else did too. Even more recently I was trying to plan a trip to go skiing and I didn’t realize how much the passes could cost. Or the gear. Or the hotels. Or flights…

What’s the most “expensive” piece of clothing you purchased, which made you go “this is expensive!”

I think my most expensive item of clothing is a $300 Lululemon rain jacket. To date it is the most money I have ever spent on an article of clothing and I do regret it. I have better $60 jackets that I feel less showy wearing around.

What’s your expensive hobbies?

PC building, robotics, wakeboarding and lacrosse. Besides that I also work on cars and bikes.

How is lacrosse expensive?

Pads, travel, tournament entry, club team dues, etc. It is one of the most expensive field sports out there

What work do you do on cars and bikes? Like upgrading them or what?

I build high powered electric motorcycles primarily. I’ve been working on it for over four years and it out performs anything on the street. I’ve also been developing other prototype motorcycles that use knowledge applied from school in robotics.

Do you ever come across people of similar wealth to you and they act like every bad stereotype of “the wealthy”? If so, how does that affect you or make you feel?

The short answer, YES. There are so many assholes out there that flaunt their wealth and have a total superiority complex. These people are actually pretty common. I’ve lived in Washington DC and California, and in both places you run into these people all the time. It honestly makes me feel a lot better about myself because I know I’m not nearly at their level of narcissism and vanity.

Do you have a lot of girls trying to hook up with you just because you come from money?

I never tell them I have money and they have no reason to suspect it, so it hasn’t been a problem. The only problem was in high school when they would see my house and realize something was up. My house is the only “showy” thing my family owns.

I’m not saying that my house gives away the scale of our wealth, but it definitely says that we’re “wealthy” to some degree. And personally it says it too much for me. Its only a 7 mill house but I still hate it.

That being said, I did date someone long-term who learned about our financial situation (she came from a very poor family) and it did negatively impact our relationship.

How so?

She was on a scholarship to her school and it got revoked during covid due to “changing budgets.” We supported her but later realized that she had lost her scholarship because of grades. This put strain on the relationship among other things like her weed consumption, therapy costs, and rent.

Do rich people really “know a guy” for everything?

Rich people DO know a guy for everything. This is not an understatement. My father had a brain tumor that otherwise would have cost us likely millions of dollars to deal with. It ended up being a $5 co-pay. My sister‘s horse suffered a tendon injury that otherwise would have definitely required it to be put down, but my family paid for it to receive stem cell injections. Any injury, any hurdle, any problem you face is almost always solvable through money.

What’s your opinion on inheritance? How high do you think it should be taxed?

I believe it should totally be taxed, but the reality is that the rich will always figure out ways around this, either through yearly “gifting” or through different types of insurance policies.

There are SO MANY LOOPHOLES. I know next to nothing about these, but I still feel like I know 1000 times more than the average person. I’d say about three or four times a year I sign some legal documents that I barely understand that my parents present as a way to transfer money to me to save money on taxes. It’s always completely legal and I trust that they’re doing it for the right reasons, but it definitely bypasses a lot of the taxes that a “normal” person would fall victim to.

What do you think has been the biggest obstacle in connecting with poorer people?

The biggest obstacle has always been my social anxiety paired with a lack of understanding. I have infinite compassion towards those that are less fortunate financially than myself, but however much I would like to, I will never understand their struggles.

Do you ever donate to charities like Red Cross etc?

My family actively donates millions every year to various causes (mainly cancer research and the bone marrow registry through gift of life). They also support my school for basic needs, clubs, and other organizations that we believe can use the funds for good.

I worked for the red cross through high school doing fundraising campaigns and attempting to modernize their fleet of emergency response vehicles.

Have you ever just randomly gave a stranger a large sum of money. Or like a large unexpected tip?

I have given and continue to give extremely large tips everywhere I go. This is something I’ve talked with my family about at length and we are all in agreement that if we can make a hardworking individual in the service industry’s day (or even week) we certainly will.

I routinely tip around 100% if not much more. The faces that they make and impact that it has is obviously worth every penny. When I pay for things in my daily life with my own personal money that I earned by working, I’m very conscious of price and am actively frugal with my money, but I make a point to carry around enough cash that came from my family (not me) to tip at these extreme levels for almost every expense.

That being said, we do not just give people money. This is one of the reasons that we still have a ton of money. If someone is in desperate need and we can make a difference we will, but we never just give large lump sums of money to people for no reason.

If you woke up tomorrow and it was all gone, what would scare you the most?

Medical expenses. I have narcolepsy and am prescribed modafinil for it. It is a controlled substance that is also commonly abused as a silicon valley smart drug for nerds on coding benders. I currently just have a $5 co-pay but would otherwise literally be paying about $600 a month minimum. On top of that I play sports and have physical therapy for my knee. I don’t even know how much it would cost to continue so I would have to quit sports. My mental health would be in the sh*tter as well because my therapist would cost thousands.

What is your relationship quality with your parents and family?

I am super blessed to have great parents who are very levelheaded and love me very much. Though my father was out of town for five days a week throughout my entire childhood, I am extremely close with him. They are my biggest role models and I tell them everything. When I say everything, I mean everything. From when I lost my virginity to the fact that I took shrooms in the desert with friends a few weeks ago. My relationship with them is extremely healthy and I couldn’t be more grateful.

Speaking on the behalf of many of my wealthy friends, most families are not like this. Most either get divorced or have unhealthy family dynamics that create a cycle of dysfunction in their children. I am so incredibly grateful this was not the case for me or my sister growing up.

It seems like you are really well grounded, do you ever think about saying fuck it and living a lavish lifestyle?

I know it sounds fucked up, but I simply don’t want to. I’m so much happier living the way I’ve been living and that might not be understandable from your perspective it’s clear as day for me.