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.
I live paycheck to paycheck - I just don’t dwell on that fact as The Determening factor of the measure of my life
The biggest breakthrough I had is when I embraced my life for what it is and decided to enjoy it
I no longer live in the vicious cycle of berating myself for failure or not being rich enough to be worthy of praise and self esteem. I don’t conditionally give myself permission to be happy only once I am successful enough. I don’t measure myself by someone else’s standards about what I ought to be, or ought to do or ought to feel
Instead, I whistle while I work, when I worry and can’t go to sleep I count my blessings instead of sheep
If you don’t like making a decision between a phone service and (whatever else was supposed to go there) spare a thought for those among us who have to make that decision between medication and food. And show a little gratitude you don’t count yourself among those
I can tell you are bitter about your circumstances and that’s bad for you. Nobody else cares if you’re unhappy with your life or not. Not internet strangers, not motivational speakers
I offer you this as someone who was were you are and moved passed it. It might not be what you would like to hear but it is a view point that comes from a place of experience and sincerity
You do with that what you will
PS don’t fall into the trap of believing an ism will solve your problems. That’s a fool’s errand