So on a point-by-point basis:
On how easy this guy's life is? Yes, I disagree. It's certainly easier than someone who lives in abject poverty or dying of famine but life is not easy. Not for anyone. Life is difficult. I disagree that this person's pain of loss or loneliness is easier than anyone else's because he has money to buy distractions. IMO that makes it different but not easier. Pain is pain and loss is loss and loneliness is loneliness whether you think you can buy your way out of it or not they remain an absolute
On how dreams don’t put food on the table? I do disagree. I am living my dream and putting food on the table. I have met others who told me the same. I have heard other (like this guy) speak of it
Or about the benefits of “living without regrets?” I have certainly discovered the benefits as a first-hand experience so yes I disagree
Or perhaps the motive that these rich people tell us poor people to live under the guise of ‘money can’t buy happiness?’ What exactly is their motive? I don't follow what your point is supposed to be. That all rich people are banded together in one, homogeneous cabal conspiring to delude you into thinking positively and striving to succeed because that is how they continue to enslave you? Well... that's a little out there, wouldn't you agree? Especially since you clearly don't "buy it" yet you are still "enslaved", not so?
I made my point absolutely clear and yet you strawmanned me.
He became a motivational speaker so he can lay his head down at night and say “I did good.”
Life is easy when you’re worth as much as he is. Loss and loneliness? Much easier to deal with when you can afford to miss work.
You are incredibly lucky to live your dream, but you are an outlier, not an average.
It is easy to live without regrets when, again, you’re rich enough to be able to do such a thing.
I think we’re just living two different lives here. You are somehow able to afford living a life this guy wants you to live so you think his message is genuine. I am living paycheck to paycheck and literally can’t afford to do anything he wants me to do, because he doesn’t know how it feels to choose between phone service. So to me, his message is callous and tone deaf.
Smug motivational speakers, in their insipid speeches, urge rich and poor alike to sleep on the finest silks, to hire only the most beautiful, and to leave nothing behind for would-be scavengers. Don't let it get to you. When the revolution comes, bourgeois jerks like this will be lined up against a wall and shot.