What it feels like to have $100 million in the bank


There’s a common marital fight in the Hy Household.

It’s not about the dishwasher. It’s not about the merits of Tiger-styled Parenting.

It involves travelling. Economy Plus, to be specific.

This question leaves us a house divided:

When does the trip begin?

Is it the moment you leave your house?

Or the moment you land at your destination?

Now, if you plot our net worth on this Scale of Wealth, the answer becomes a paltry:

It doesn’t matter, you’re still at Level 2.

Money: The ultimate measuring stick

The rational brain likes 2 things.

Money. And ordered lists.

Here’s Slack’s founder, Stewart Butterfield, with his 3-tiered approach to wealth:

But the voyeur in me was curious. What do all these lists look like when you assign a real number to each level?

Welcome to the Big Leagues

I went down a rabbit hole looking for someone who could add some meat to these bones.

And I struck gold (with my search, not my business) with a Reddit thread detailing What do insanely wealthy people buy, that ordinary people know nothing about?

Here’s how the numbers came out:

  • Rookie: $10 -$30 million
  • Pro: $100 – $1 billion
  • All Star: $1 billion +

With a major disclaimer at the end (so make sure you read on).

Rookie: $10 mm to $30 mm

This represents roughly 1.6% of the US population. While this redditor is anonymous, the level of detail (and my own interactions with the uber-wealthy) lead some credence to their perspective.

The main benefits of the rookie level of wealth are:

  • Flying private
  • Staying in 5 star hotels
  • Buying any car you want
  • Owning multiple residences
  • Socializing with congressmen and senators

The interesting thing to me is that this category seems to “monetize their wealth” through travel and material purchases. The post adds:

You can travel ANYWHERE in any style. You can buy pretty much anything that normal people think of as ‘rich people stuff’

Pro: $100 mm to $1 bn

Some back-of-the-envelope Internet Math says that 8,000 people in the US fall in this category. And this is a tough one, because despite being a wide range, the poster says:

Life doesn’t change much when you go from being worth $200mm-$900mm.

Your multiple residences have more staff.

You socialize with movie stars/politicians/rock stars/corporate elite/aristocracy.

You run out of things to buy, so you “start buying art.”

Why is this level so attractive from a media perspective? Women. The post continues:

Because at this level, they are all over the place. Every event, most parties. The polo club. Ultra-hot, world class, smart women. Power and money are an aphrodisiac and you have it in spades. Anything thing you want from women at this point you will find a willing and beautiful partner. You might not emotionally connect, but damn, she’s hot.

One thing missing from this level:

Friends and family that love you for who you are. They exist, but it is pretty damn hard to know which ones they are.

All-Star: A billion plus

The prior level showed us that with the exception of art, you’ve already run out of physical things to buy.

Per the post, this is the category of access, influence, time and experiences.


  • You can get any billionaire on the phone
  • You can get your party’s senator on the phone
  • You can “occasionally” have a real conversation with a head-of-state

Which all leads to…


You can have a private lunch with your governor or the Secretary of Health. According to the post, “you have many ways to shape public policy and the public debate, and you use them.”


  • You pick your tee times
  • The best table at any restaurant is always waiting for you
  • You’re whisked (via velvet rope) to any major event (Super Bowl, Grammys)

(I was surprised that you had to be a billionaire for these things)


This part does sound pretty cool. You can basically buy yourself any experience with a billion dollars. The only limit? What your mind can dream up.

Want to play tennis with Pete Sampras (not him in particular, but that type of star)? Call his people. For a donation of $100k+ to his charity, you could probably play a match with him. Like Blink182? There is a price where they would simply come play at your private party. Love art? Your people could arrange for the curator of the Louvre to show you around and even show you masterpieces that have not been exhibited in years. Love Nascar? How about racing the top driver on a closed track? Love science? Have a dinner with Bill Nye and Neil dGT. Love politics? have Hillary Clinton come speak at a dinner for you and your friends, just pay her speaking fee.

Once again, love becomes problematic. Apparently, when you have all of this at your fingertips, “normal relationships” are hard:

It is hard to sacrifice for another person when you are never asked to sacrifice ANYTHING. Money can solve all problems for someone, so you offer it, because there is so much else to do. Your time is SOOOO valuable that you ration it. And that makes you lose connections with people.

Have you lost the plot?

You’re probably wondering why I dedicated 800 words to the lives of billionaires. After all, isn’t the point of RadReads to re-examine your relationship with money and ambition?

And you’re right. I was reading this to answer two questions:

  • Am I really missing out on anything?
  • What are things that money can’t buy?

I learned from this post that if you’re not looking for outsized influence (both good or bad), money displays extreme diminishing returns.

I mean, you run out of shit to buy, so you end up buying art? No thanks.

Sure, attending the Super Bowl or skiing at a private mountain is pretty dope. I’ll give you that. But to dedicate 30 years of your life grinding for those experiences? Not for me.

So what are things that money can’t buy?

Money can’t buy genuine relationships. The ability to be loved. And the ability to love others.

Money can help you get fit and stay healthy. It can help you extend your life via access to treatments – yet can’t prevent the big kahuna (i.e. death).

And back to the original Reddit Post, a final word of warning. Every life has the same emotional degree of difficulty:

Seeing all of this doesn’t make me want to get into the top tier. Different lives have the same emotional degree of difficulty: I met Sylvester Stallone at a party a few months back for the first time. Great guy. Has a beautiful, smart wife and a great career. He had a special needs son who died young. Nobody has it all. Nobody.


Should we work together?

If you’re reading this, you’re probably not in any of these categories. Neither am I.

But you still want to see how money can help you find a fulfilling career without stressing about money (and controlling your time). If that’s you, sign up to our Group Coaching programs.

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