“Billionaire Executive, 56, Dates 22-Year-Old Woman.” So What?



This is decidedly a “non-story.”

So why did I publish it?

To make yet another in an eternally long string of identical points, that wealthy older men who date much younger women are simply leveraging assets the way everyone does at every stage of life.

Young men leverage youth, beauty and the prospect of future success while older men leverage success, maturity and appreciation, among others.

It’s all asset management, consciously or otherwise, but usually consciously.

Then, and only then does everything else matter.

It’s no different than everything else in life.

We leverage what we have at our disposal and for those who come up short, you see comments like the following:

“I hope she gets half the money”

“Oh god, lol! What a joke!”

“I’ll date ya, man. I’m not a female, but for the amount of cash you are willing to throw around, a little experimentation is ok.”

“It’s good to be rich…..It’s then you only see that ALL women have a price tag !”

“Rich men can be the biggest fools when it comes to women. They might have loads of cash but fail to own mirrors.”

If everyone could afford their fantasies, they wouldn’t blink.

Now you know a little more about the people commenting, both men and women.

4 Nannies + 2 Twins = How Money Evens the Playing Field


Rolling Stones guitarist Ronnie Wood, 69, and his wife Sally, 38, tend to their newborns, Gracie Jane and Alice Rose. 



In days gone by [lots of them], a man of 69 was, for the most part, on his death bed.

The very last thing he was doing was having children with a woman 30 years his junior.

Then something happened [a lot, actually], and this same man is now clean and sober [for the most part, I assume], propped up by the miracles of medical science, and thus, living like there’s no tomorrow.

This is what fame and fortune [fame + money = relevance] does for most men.

It’s like a blood transfusion that just keeps giving and giving.

You’ll note that many of the comments under the article are dismissive of him and his “relationship.”

People simply can’t resist the temptation to criticize his motives, and hers.

Nothing is real. It’s all one big endless past time for a man who has nothing left to do with the time he’s not touring.

Well let’s get real.

No one in their right mind has kids at 69 without the ability to afford nannies…lots of them.

It’s not that he doesn’t want to be a part of their lives, just not all of it.

As for his young wife, she’ll do her part, with lots of help, while her husband does what he does when he wants to do it, because like he’s Ronnie Wood and the scales have to balance somewhere.

Wealthy older men have reached a point in their lives where they just don’t give a crap what other people think about them and their lifestyles.

For one thing, they don’t have to. Nothing rides on their reputations in the office.

This is the beauty of success. No one can fault you for it no matter how you choose to live out your years.

It’s like a golden wrapper, a force field that follows you around wherever you go.

You walk into a restaurant, hotel, resort property – even local liquor store – and there’s a kind of parting of the waves.

It’s something you get used to, which is one reason men who find themselves suddenly without it blow their brains out.

The story here is really about what it’s like to feel validated for everything you ever dreamed of as a little boy.

For young men there is tremendous pressure to amount to something, to achieve.

And as we age we gauge our success by those around us, hoping that we’re still close to the front of the line, relevant, valid.

All older men validate themselves on their achievements whether they admit it or not.

They subconsciously sum up everything to a series of equations and derive a number that determines their relative worth.

And while some men do not base their lives solely on financial success, I don’t know any.

While vicariously living through one’s children is a fallback position, it really sucks to rely on their financial support.

The moral of this story is that life is a food chain no matter how you dice it.

You have to fight for every scrap, and then live to tell a very tall tale that you and people around you can easily quantify.

It is unforgiving, savage, and brutally objective.

This is why reality television focusing on the super rich is so popular, while anxiety disorders are the most common mental illness in the U.S., affecting 40 million adults…and counting.

Now you know why people beat up on Ronny Wood…and why Daily Mail published it in the first place.

Concluding Remarks and Data Points

  • 1% (2 out of 233) became wealthy before the age of 40
  • 3% (6 out of 233) became wealthy between age 40 and 55
  • 16% (38 out of 233) became wealthy between age 46 and 50
  • 28% (66 out of 233) became wealthy between age 51 and 55
  • 31% (73 out of 233) became wealthy between age 56 and 60
  • 21% (48 out of 233) became wealthy after the age of 60

So yes, Ronnie was one lucky SOB.

Inter-Generational Relationships Are Challenging Like All Other Relationships […with a few exceptions]


So let’s say you’re an attractive 30-year-old woman who’s fallen for a man of 60.

While it may provide shelter from the storm of corporate climbing and adolescent pack animals, it’s not all roses.

There are inherent risks, difficulties, and pitfalls that may prove impossible to overcome.

But most women I know who find themselves in such relationships know exactly what they’re getting themselves into, and won’t leave without a severance package or SWAT standoff.

Generational Divide

An older man may find himself in the position of surrogate parent if the younger woman is substantially younger, or the man is more traditional and/or less fluid in his approach to life.

If, for example, he spent his entire career surrounded by corporate types, adhering to stodgy cultural norms, his ability to communicate with a creative Millennial, for example, may prove impossible.

On the other hand, if he’s lead guitarist for a major rock group or an A-list actor, she’ll assume the role of surrogate parent.

Strong, Powerful Men Didn’t Get to Where They Are by Accident

Older men may have mellowed somewhat with age and maturity, but this mild-mannered guy is only a cover for a ruthless and aggressive nature that got them to where they are in life. In other words, the nice house didn’t happen without a fight.

This usually means that as long as everything is going well, you get the cool older guy. But the moment the shit hits the skids, you get a first hand look at human predation from the perspective of prey. Men will defend and protect their financial interests and prosperity over all else in their lives, including you.

Of course, gorillas do the same damn thing, so it’s not exactly news.

Taming and Older Man is a Ludicrous Pursuit

Why women like to fix older men is beyond me. I can understand trying to get a 25-year-old guy to get out of bed in the mornings, and to get a life. But older men have been there, and at this stage of the game don’t give a shit what anyone thinks about their lifestyle habits.

He’s already self-sufficient. He doesn’t need you to pave the way forward. You can’t cut him off from his friends, or interests, or in any way undermine his life. It’s already worked for him. His entire psychological framework is built around decades of experience. Give it up.

If You’re Seeing a Married Man, Love Isn’t Enough to Shake the Tree

The married guys I know with “women-on-the-side” like the no-strings-attached erotic sex, even the fantasy that love plays a major role in all of it. But understand that it’s still fantasy. All of it. Your best bet is to find a recently divorced older man of affluence, or just go the married route in exchange for college tuition and be done with it. Graduate programs run 50k. Get real.

The Sexual Equation

No matter how successful and older man is he cannot reverse the aging process. Understand that as you turn a year older he turns 7 years older [after a certain point in life]. So if you want to build a long-lasting relationship with him, you better make damn sure your sexual rhythms and desires are on the same page.

While adventure and passion are still very much on the table, things will eventually change.

Of course, it’s also important to keep in mind that a young man will eventually get bored with you, especially after he’s achieved success in his 40’s, and will often replace you with someone half your age that he won’t be bored with. It’s a cycle that tends to repeat itself a few go-rounds in life.

Parental Issues

In my case, the woman in my life’s parents refused to speak to me for the first 3 years of our relationships, assuming that I was buying her love, and at the same time, stealing her youth and opportunity.

Thankfully, it passed and we now have a wonderful relationship. But it was awkward. Be prepared for that.

Completely Different Entertainment Preferences

In many cases, taste in music is a major marker of significant age differences. In my own relationship, though, our tastes were identical.  In fact, she had more Zeppelin albums than I did. Another ironic twist of fate was that I was the one going out every night of the week, while she preferred evenings at home watching TV, painting or video editing.

I could argue that she made me grow up, and that all had to do was provide financial stability, love and commitment in exchange for a more adult lifestyle. It was a small price to pay, and probably paid for itself given my wayward leanings.


Affluent older men do NOT choose women unless they’re prostitutes. It’s the other way around. This is one of life’s biggest misconceptions about the older man/younger woman paradigm.

This being the case, she will decide whether or not she can handle the difference in age, the disparity between their respective success and power, his intransigence, the sex and whether or not he knows – or gives a crap about – Taylor Swift.



Affluent 50 to 60-Something Men Still Choose Beauty First


“…all older women hear (and thus believe) that older men are only looking for much younger women. OK, many of them are. But are they getting them? Not really, unless they’re wealthy and powerful. (And I have always believed that it’s good to identify those men and remove them from the 50-something dating pool ASAP; I’m not interested in men like that so move along, men, and good luck!”). Vicki Larson, journalist

I hate to tell you people this, but a simple fact can save you a lot of heartache:

Reasonably attractive, healthy and successful older men have lots of choices when it comes to choosing partners.

Too many, in most cases, which is why so many of them are single or serial monogamists, the emphasis on serial.


When it gets down to it, money and power are the great equalizers.

Conversely, youth and beauty are also commodities openly traded on the human stock exchange.

Whether you’re young or old, you have different assets to barter, but something is always for sale.

Most of the older successful guys I know have an exacting set of standards they apply to the acquired women in their lives.

These are the very same standards, by the way, they applied to their ex-wives before they divorced them 20 years later.

The fact is successful men prefer to date younger women is because THEY CAN.

Generally speaking, women over the age of 17 are not attracted to youth.

They’re attracted to confidence and power.

Therefore when a beautiful woman in her 20s or 30s meets a man who is in his 50s, with the world in the palm of his hands, it’s sexy and alluring to her.

His age becomes irrelevant.

Walk into any upscale restaurant or bar and what you will see are drop-dead gorgeous women accompanying successful older men.

These women were not forced at gunpoint, believe me.

To many men I know, it’s almost irrelevant whether these women are truly in love with them or merely out to make better lives for themselves.

It matters that they are in the company of a beautiful, intelligent and uncomplicated young woman.

The rest they leave to a suspension of disbelief.

She is everything their wives once were before time took its pound of flesh and soul.

No wonder so many middle aged women without much to leverage scream and yell about all of this.

But put them in the position to do what these young women are doing and you wouldn’t hear a peep.

The fact is average men and women receive average returns, and exceptional beauty and youth will always win out where successful older men are concerned.

Is it fair?


But pretending that “real men” don’t want younger women is delusion. That they want an equal is naive at best, disastrous at worst.

According to one NYC matchmaker, this is the normal course of things:

“I recently had a 78-year-old client who wouldn’t even consider a woman older than 50. If you are 25 years old as you are reading this, let me put this in perspective: That would be like dating a 55-year-old.

That brings me to why I can’t take on women as clients; and no, misogyny has nothing to do with it. In this tough singles market, if a man pays top dollar for a matchmaker, he expects nothing less than a 29-year-old model.  As a result, I cannot find a husband for a 47-year-old schoolteacher with two kids and three mortgages.”

So where do relatively pretty, average 40-plus women find men of means?

They don’t.

What they can and do find are men of equal value, which is not a particularly palatable prospect for most.

My recommendation to such women:

1] Join a book club.

2] Enroll in a continuing education class at a local college.

3] Attend art openings.

4] Get out of the house – maximize exposure.

5] Go back to therapy.

Nature is neither kind nor compassionate, but the good news is that there are exceptions to every rule.

Just not very many.