Does this billionaire kid need to be humbled?

I came across a Jubilee video today that got me thinking:

I’m the Son of a Billionaire. Ask Me Anything.

(These videos are a guilty pleasure of mine. I hate that I enjoy them, but welp, I do.)

The titular Billionaire’s Son was exactly what you’d expect, as one of the top comments said:

“I came into this video expecting to see a guy who is sheltered, not humble and unaware of his privilege. Shockingly, I was completely right.”

His identity is his riches and his privilege, as every second of hearing him talk shows us. He doesn’t tip because he “isn’t made of money”. He acts calm and collected around most of the interviewers, until another billionaire’s kid shows up and he gets all bro-y with him.  And everything he says about wanting to make an impact in the world is word salad to my ears.

It’s easy to hate a guy who acts like this, critique him, and imagine what he’d be like if life humbled him and he got more empathy for lower-class and middle-class people’s struggles.

That’s not what I thought watching him.

I like him.

And I don’t think he needs to change as a person nor do anything different with his wealth.

I’ll admit I was judgy at first, but what he said at 7:06 stood out to me.

“I consider myself a villain, but it’s a necessary evil in life. Without it, there isn’t the good guys.”

Yeah, Bobby here isn’t objectively a good or altruistic person. I mean, if you had billions of dollars, wouldn’t you be doing something charitable with them? But as usual when you read people, subcommunication is everything.

He understands his place in the world. And doesn’t try to be anything he isn’t.

He’s an arrogant, spoiled kid at heart who defines himself by his material situation, and HE OWNS IT.

He won’t ever relate to someone who grew up poor, nor to someone who grew up working-class or middle-class, and that’s that. HE OWNS IT. I like how authentically entitled and out-of-touch-with-the-peasants this guy was, as much as I who grew up middle-class can’t relate to him.

He’s not a bad person for being a product of his wealthy upbringing. He is who he is. He lives the super-rich, blowing 30k with no problem, “lemme tell you about the time I fucked Lindsay Lohan” never (I assume) working a normie job in his life type of lifestyle with no shame about it.

You can learn a thing or two from Bobby, if you have an open heart.

Whoever you ARE, you need to own it or be miserable. You will never be anyone but yourself.

He has his place in the world, and you have yours. Let’s assume he’d try to “humble” himself and live a modest lifestyle, define his identity by NOT being a spoiled rich kid, or work a more “normie” career. Hah. NO THE FUCK HE WON’T. Even if he did, it’d come from a place of incongruency and FORCING his life and growth to happen.

He doesn’t force his life to go a certain way. That’s why I like him.


You need to internalize this lesson, or be shite at reading people forever:

People who speak honestly about their shortcomings are good people, even if they’re arrogant or self-unaware about it. You can trust them.

People who put up a “good guy/good girl” persona that’s misaligned with their heart… Who can’t be open and vulnerable about their rough edges, except when it’s to get attention… Watch out for them. These are the people who’ll betray you, burn you, and turn out to be snakes behind the scenes.

Whether it’s the girl on Twitter whose persona is a good, modest girl all about love, healthy relationships, and traditional marriage, but turns out to be toxic and manipulative in her personal life…

The dedicated, productive professional who lives for power trip after power trip…

The guy who just wants to find a good girl with good values in the sea of broken whores… Then dates broken whore after broken whore…

Or whoever talks shit about having good values and righteous goals, but doesn’t fucking act like it…

See these people with your heart, not with your eyes. Or else they will manipulate you and burn you. They prey on good people who are scared to be the bad guy.

So stop being scared to be the bad guy. But we talked about that in the last email.

Anyhoo, this LARPing isn’t solely about good values vs bad values.

A lot of people seek to CHANGE who they are and their place in the world, instead of improving it.

In my case, I spent many years attempting to be a normie party boy who fit in with that whole college lifestyle, and ended up successfully holding up that persona for a long while…

But my persona broke in the end, and I never reclaimed it no matter how hard I tried. It was incongruent with who I am at my core – a guy who’s positively weird, polarizing, and goes his own way in life.

So who are you?

Who are YOU?

So many dating coaches talk about learning game, getting your preselection right, and building up your lifestyle. This stuff works and you shouldn’t neglect it, but too many guys in the dating scene neglect another fundamental truth:

WHO YOU ARE is equally, if not much more vital in attraction.

You may not end up dating rich models or trad church girls or geeky cosplay girls or whoever you logically think you SHOULD want to be with…

But you will end up dating SOME girls. Girls who are aligned with YOU.

I had a client ask me a bunch of questions about Andrew Tate not too long a while back. How can he get the girls Andrew Tate would date? What does he have to change about himself and his life to get such girls?

So I told him:

“Kyle, you won’t ever get the girls who want Andrew Tate. You’ll get the girls who want Kyle.” (name changed for privacy)

Nor should he try to. My client “Kyle” will get the girls HE gets, once he gets in touch with what HE truly, deeply values, not with what Andrew Tate deeply values.

That right there is one of my primary philosophies in coaching.

I won’t force you to become a club player like Justin Marc, nor get the girls he gets, if that’s not who you desire to be. I won’t force you to date introverted, shy girls if you’re not an introverted, shy guy yourself. I won’t force you to be an intellectual, refined guy who gets intellectual, refined girls. I won’t force you to be like me, nor to get the girls I would get. I won’t tell you you need to date wealthy models to consider yourself an attractive guy.

I will help you become aware of YOUR strengths, YOUR core values, and WHO YOU ARE deeply, and to date the girls whose holistic selves align with your holistic self.

The ladies are as diverse as we gents are. So devaluing your holistic self, trying to change yourself instead of improving yourself, may get you temporary, superficial results in the dating world if you learn to play your persona well…

But who you are at your core, and as a product of your life so far WILL NEVER CHANGE. Best case scenario, you’ll become like me in my douchey party boy days, able to vibe and game with those normie party girls, but you won’t feel a real connection with them. Your persona will always crack and show your true self in the end.

So don’t hide yourself away. Don’t be someone you’re not. Be like the Billionaire’s Son Bobby and own your place in the world instead of shaming yourself for it.

If you’re having a hard time doing exactly that…

If no one ever taught you how women work, nor to view your own masculinity and personhood in a holistic, integrated way…

See me in coaching, and become my next client success story.

I look forward to working with you. 🙂

– Ben

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