Confessions Of The Son Of A Billionaire

August 21, 2018 | No Comments » | Topics: Life Experiences

How much is your father worth?

My father is worth just shy of $2 Billion liquid, and he’s on a rapid trajectory be worth significantly more.

What do you do for a living?

As for my current job, I work a generic IT position with a standard salary – nothing that will produce the kind of fortune my father’s work has.

What kind of car do you drive?

A 2014 Subaru Outback. Prior to that, a very-used ’98 Outback. Probably not the answer you were expecting!

As for my parents, the primary cars at each property are a Mercedes GLS and SL Roadster; they have lots of others, but nothing too fancy. Mostly old Chevy and Ford cars primarily driven by the various employees they have.

What do you do for work and why did you go into that field?

I’m a computer systems adminsitrator for a small company because it’s what I enjoy and it doesn’t require a large amount of non-immediate work. I didn’t inherit my dad’s strong ambition and drive, unfortunately.

Do you think having the trust fund played a role in your lack of ambition and drive?

The truth is that I didn’t know about the trust fund until I got married, so it had little influence over my upbringing. I knew that my parents were well-off and perhaps assumed that that would come to us someday, but nothing was explicitly stated about it as a kid. So if it did affect my ambition and drive, it was more subconscious. It’s certainly possible, though it didn’t affect my siblings. I’m more inclined to think of it being how I’m neurologically wired, just as my dad is wired to be a workaholic but less emotionally engaging. But it’s hard to say. I certainly do blame myself for my lack of sustained ambition, most of the time.

Do your nearest and dearest know your worth, potential or otherwise?

Well obviously my wife knows! We have one pair of friends who at least know my parents are very wealthy, since they’ve stayed with us at one of their properties. Everyone else (hopefully) assumes we have little more than the middle-class lifestyle that we provide for ourselves.

Wait so does your father not share his wealth with you?

We enjoy their material assets, get awesome gifts for Christmas, and each have a trust fund of $28K/year. But to have a comfortable life and income, we have to have our own jobs. For now, at least.

Did your father insist on a prenup for your wife to sign before marriage? 

They suggested a prenup, but it didn’t happen. My wife hates their wealth and wants no part in it so I’m not concerned about her trying to run away with it.

How is your relationship with your parents?

My relationship with them is complicated. I appreciate what they’ve provided, but the emotional connection has been poor. I wish I could feel closer to them, but I just don’t think they’re wired for that kind of relationship. Dad’s a workaholic, Mom’s a socialite, I’m the kid who didn’t do everything perfectly and felt like the pariah for a decade. Things are better now, but conversations are rarely more than business and small talk.

What kind of schools did you go to? Were your peers wealthy?

I went to a private school for grade school, a boarding school for high school, and then private university which I eventually dropped out of. Since the familial wealth grew as I did, the peer group evolved over time; but I never understood the extent of their or our worth until recently. My perspective was more than a bit off growing up.

At what point in your life did you realize that your parents are very, very rich?

Far later than I probably should have. I didn’t really realize just how out of touch I was until around 23 or 24. Granted, we were worth significantly less when I was younger, but still, many things that I took for granted were definitely not common.

Do you think you grew up in a bubble, so to speak, unaware of things those of more modest wealth take for granted? Any funny or embarrassing moments?

I think so. Generally I was more naïve than anything. I can’t think of any specifically funny moments, but there are a lot of things that I roll my eyes about where I was much more flippant about the price of things. I was just a kid who was excited by certain things, but I didn’t realize that talking about them so much was likely very awkward for others who were adults and yet had experienced far less. I remember asking the person who maintains some of our land what his favorite place to travel to was, and when he told me that he had never flown on a plane in his life, I suddenly realized that there was a very big difference in how we grew up. I felt quite awkward and guilty about that one.

Do your parents pressure you to want more? Make more money?

Well I do think that my anxiety comes from my dad wanting me to do better, in part. As I mentioned elsewhere, I dropped out of college; I did terribly in school – had high overall intelligence and tested well but just failed to put in the necessary sustained effort. I’ve recently been diagnosed with ADHD and the difference since starting treatment has been profound, but I wouldn’t dare tell my father that because a) he’s convinced that it’s a fake condition, and b) I doubt the diagnosis myself because it just feels like too convenient of an excuse. I’ve been taught that there’s no excuse for not succeeding other than not working hard enough, and by that metric, I’ve largely been a failure. My dad’s success and his hope for my success has been an enormous burden, but I think at this point he’s generally “given up” on me having the same drive as him.

Do you have other siblings?

I have siblings, and I get the feeling that they’ve been better-supported financially because they’ve lived their life much more in line with how my parents had planned.

What’s that -one thing- you never got as a kid?

A gaming console. Or as my dad affectionately referred to it, the “Super No-friend-o”. Somehow computer games didn’t fall into that purview though, so I had a top-end desktop and laptop anyway. Didn’t stop me from being obsessed with gaming; the PS2 was the first purchase I made when I started getting my own paycheck.

Seems like even though you had connections to wealth, it wasn’t used as a magic wand to get you shiny things all the time. Did you learn the value of money and earning, over just “having” money?

Sort of. We (my siblings and I) certainly didn’t have carte blanche, and I’m self-sufficient currently outside of a growing and accessible trust fund; but they have a “what’s mine is yours” mentality when it comes to enjoying their homes and possessions, which are plentiful. As we speak, my wife and I are staying in one of their massive homes for a stress-free weekend, and everything from the cars to the cook is at our disposal. These days I’ve never asked for something that they’ve said “no” to, but I’ve never tried to push the limits.

Are the other homes always “staffed” even if your family isn’t there, or is it a more “on-call” situation?

Some of the properties are quite large and require constant upkeep. One is on a farm and has a family living on the property – the husband and wife handle the land and home maintenance, respectively. Some of the properties are in city high-rises and have building staff to take care of them. Then they have their main guy (I have no idea what his official title is but he’s effectively a modern butler valet) who almost always travels with them and handles arrangements to keep their flow as uninterrupted as possible. He also lives in a home provided by my family, right next to one of their “hub” properties.

Do you have any “regular” friends now? What’s a Friday night like for you?

My wife and I are shut-ins and will spend most evenings just watching shows and playing video games together. When we meet up with friends, we meet at the pub or go to one of each others’ houses. A couple times we have taken some friends up to one of my parents’ properties, but only after we’ve come to know them quite well.

But generally, unless I’m with my parents at the time, I live a very standard middle-class lifestyle.

Thoughts on economics and/or politics? Libertarian free market, radical socialism, social democracy, liberal welfare state?

I generally lean conservative/libertarian on fiscal issues, which probably isn’t surprising.

Do you travel a lot ?

I did as a kid, less so now that I have my own income and my own job schedule. Starting around 12 or so, each spring break was spent on another Caribbean island and each summer was spent visiting another country or series of countries. My dad would increasingly joke that our hotels were picked by my mom Googling “Most expensive hotel in ____”; and those trips usually consisted of a private tour guide who would take us everywhere, get us behind velvet ropes at various museums, etc.

I didn’t appreciate how special those trips were as a kid, though I certainly did love them.

What games do you play?

We play special billionaire-only games that you wouldn’t have heard about.

Kidding. We just wrapped up Dishonored 2 and are currently replaying the Bioshock trilogy.

What type of hobbies do you have? 

Technology, media, games. I have an awesome home theater which is my biggest piece of personal extravagance.

Please elaborate

Well we squeezed it into our relatively normal house, but it’s a 150″ screen with a 4K projector, seating for eight, Atmos 7.2.4 sound, and a whole lot of soundproofing to keep it contained 😉

I was so close to convincing my dad to put an amazing theater into his newest home, but regrettably he decided that a massive wine cellar was the more prudent option. But at least I get to say that I have a better home theater than him 🙂 Not much that I can beat out the billionaire in, so I’ll take what I can get!

What’s your favorite pop tarts flavor?

Nothing beats brown sugar!

Do you actually eat pop tarts? I don’t just mean pop tarts either. Like, when I imagine rich people eating, I always think of private chefs, or at very least having someone else cook for them in some way. Do you ever just open up the panty and grab something like a box of cereal, or pop tarts, or ramen noodles? Or do you always have other people prepare food for you?

Well at the house where I’m staying at right now, there’s a pantry with Tostitos and Skippy peanut butter, a freezer with Eggos, and there are always a half-dozen Oscar Meyer wieners available for cooking. Of course there are other fancy snacks as well and our freezer is actually mostly full of the meat from a cow and pig we won at a rodeo auction last year, but sometimes you need a quick breakfast or midday snack and it’s not worth having a professional always handling it. Depends on the circumstances.

What’s a problem that billionaires have that we plebians do not?

Child-of-a-billionaire problems include rock-bottom self-esteem and endless guilt.

As for my parents, their problems are a lack of time and a loss of perspective. Worst has probably been their focus on maintaining a social appearance which has come at a significant cost in regards to their relationship with me and my siblings. They spend so much time these days trying to make our family seem perfect that they forget to do the actual things that keep a relationship strong.

Is this more keeping up with the Jones’s or just being scheduled too much to make time? Running an empire is hard work, I don’t envy then the drudgery.

My dad lives to work. He knows he doesn’t need any more money, but it’s when he’s working hard that he’s having the most fun. So for him, it’s just keeping busy. My mom, on the other hand, took our class status as an opportunity to become a major socialite. I participated in literally over a half-dozen debutante events. I felt like a trophy being paraded around, the illusion of our familial excellence masking the superficial relationships we had underneath.

Things are a bit better now since I confronted them on all of this a couple years ago, but still, our relationship is so-so at best and I expect the wealth was a catalyst in that.

You mention that you live a middle class life now and work in a normal job. Are you content with this or do you have plans to get independently wealthy?

I’m not a strong worker. There are things that I’d love to excel at, but I lack the patience and focus to accomplish them. There are many causes and industries which I look forward to financially supporting once I am afforded that lifestyle, but I would be content to just live out my life as I currently do (with more perks, of course) and leave the ambitions to those who are cut out for it.

Why do you work, particularly in mid-range IT? You could be doing anything. Does working feel like waste of time?

The trust is only $28,000/year for the time being. That’s the maximum non-taxable amount and is enough to provide a nice boost without letting us get away comfortably with doing nothing. That will change in the future, but for now, my parents strongly encourage a good work ethic and the value of earning your self-sufficiency. Not to scoff at how valuable that $28,000 has been, of course.

Are you any less miserable than we are?

I have emotional problems like everyone else. But I don’t have to worry about my paycheck, I don’t have to worry about my retirement, I don’t have to worry about supporting my child financially, I don’t have to worry about a medical crisis ruining our family… There are so many burdens that I simply won’t know. I wouldn’t dare make a claim to the same sadness and difficulties that many people deal with.

What are your thoughts on whether money can (or can’t) buy happiness? 

I once read that money can’t buy happiness but that it’s a good “unhappiness repellant”, and that seemed like a good way to describe it. There are a lot of things that can cause unhappiness that can be prevented with money: financial issues obviously, health-related crises, and lots of little things. Being able to skip the major airports and take a private jet instead bypasses a major headache!

But money can cause problems too. Especially extreme wealth.

Being given such an extreme amount of wealth creates the burden of managing that wealth properly. You don’t want to be the generation that loses what prior ones have worked so hard to provide. But you also want to do as much good as you can for the world while you have the opportunity.

Most importantly, I’m terrified about raising my kids well. I don’t want to raise spoiled brats, but I have no idea how to both acknowledge our extreme privilege and simultaneously impose a modest lifestyle. There are so many bad examples out there, and we only get one chance to raise them right.

What’s the best thing money can buy?

That’s a profound question to answer which can delve into the philosophical, so I’m just going to modify the question to “what’s your favorite thing your parents have bought?” to keep it simple and light. And to that, it’s almost impossible not to say the private jet. Not because of how comfortable it is, but because of the convenience and time-saving.

We don’t need to show up at the airport 90 minutes early, check our bags, wait in the security line, put our liquids in special containers within containers, then sprint to the gate desperately trying to reach it before the door closes. Instead, we literally drive the car onto the tarmac, let a crewmember carry in the luggage while we take a seat, and are in the air within 10 minutes. The crew is employed by us and is ready to go the moment we pull up. And our dog gets to sit in the leather seat next to us. Usually a meal is provided: shrimp caesar salads, a charcuterie board, a glass of wine, even a steak dinner if we request far enough in advance. And when we land, someone pulls our car around and meets us at on the runway, they put our luggage into the car, and we’re on the road – often much closer to the final destination than a larger airport is.

It is absolutely extravagant, but the reduction in stress and time is so significant that it’s one of their expenses that I absolutely think was worth it.