Why Should Billionaires Have All The Fun? - How to give away your money and have fun doing it!

Maybe I’m just a stubborn and idealistic dreamer with my head in the clouds hell-bent on clinging to a non-existent point. That is if bankruptcy doesn’t cling to me first.

Maybe I’m just a stubborn and idealistic dreamer with my head in the clouds hell-bent on clinging to a non-existent point. That is if bankruptcy doesn’t cling to me first.

Why In the face of financial stress, growing resentment from friends and colleagues, and my business on the ropes, why am I so cheerfully giving away one day of revenue a week?

The pursuit of happiness.

The metric I used my entire life to measure my happiness was for the most part based on the social and financial capital I accrued personally and in my businesses. The Keeping up of appearances was the daily goal I would strive for in order to maintain my pride and self esteem. To this end, wherever I thought I might be falling short, my strategy would be (to use a familiar term)… fake it until I made it. I may not have been as blatant about putting on airs as others, but as a lifetime entrepreneur, this is a strategy that I employed far more than your average Joe.

Yes, those who know me best would most likely describe me as a kind and giving person. I am always the first to ask if anyone needs help, I am always the one to stick up for those I think are being treated unfairly, and I have been told that I am better than your average listener. These are genuine traits that I’ve had all my life. Which is why in recent months, and directly as a result of the charitable initiatives that I have been retrofitting into Free Your Arms - I realized just how far from that ideal I really am.

The fear of not obtaining or losing my social or financial capital became a prison I built up over a lifetime.

I always knew that despite my cheerful demeanor, that I was at my core a highly driven and annoyingly (if not secretly) competitive person. Anyone that I deemed a threat to my financial or social status would knowingly or unknowingly get pulled into my competitive lair. This could be someone within my own social circles, or it could be someone I had no personal interaction with whatsoever. For example; One of my favorite head-games I would play with myself while driving, was randomly choosing another driver (usually someone who I thought was driving too aggressively) and silently engage them in a race to an imaginary finish line. This happened several times daily. Or maybe I would randomly select a social media influencer with lots of followers that I envy and challenge myself to surpass them one-day (not having allot of luck with that one as my tens of followers would indicate). These are the types of mental exercises that I found challenging, but over a lifetime helped nurture a cancer of resentment and envy within. Basically anyone invading my space that was not on my team I saw as a potential threat.

Over a lifetime this competitive bent built a deep well of jealousy and resentment that existed side by side with my more charitable demeanor.

In the past few months, I started to more clearly see the unhealthy effects of this competitive streak. This was a source of fear, anxiety and resentment that colored how I viewed the world. My fear of not obtaining (or of losing) my social or financial standing became a self-imposed prison that I built-up over a lifetime. It also allowed others to leverage these fears against me through withholding or removing these rewards. It wasn’t until a recent holiday trip to my parents home in Florida that I would unintentionally start down a path of growth that I find myself on today.


A little burnt out from working on Free Your Arms over the past 3 plus years, I took my annual thanksgiving trip to visit my folks in Spring Hill Florida (this is my go to destination to decompress). As I usually do when I’m down there, I try to start new and fun projects to help occupy my time. On this trip I would use my time to work on a business plan for a platform that I hoped would allow the younger members of the community to provide tasks to the older less tech savvy members of the community. It was like TaskRabbit but for the people who would not know how to use Taskrabbit. Also the taskers would come from close friends and relatives. (Most of my family and extended family transplanted from New York to Spring Hill Florida so I thought this might be a great testing ground).

After dozens of iterations I would eventually call this project The Shop (which eventually became the website you are reading this blog post on right now). As I was building this community based platform, I could see that my world view as it applied to my business started shifting from being monetarily driven to a more charitable outlook. This led to self-examination about my role as a founder. The more I iterated this business plan, the more I realized that I felt happier working on The Shop than on The Free Your Arms Website as it currently existed. At some point I decided to merge the two businesses under the The Free Your Arms banner, with the old business adopting the values I was weaving into the new.

Immediately I started to feel happier, less stressed, and less anxious. I realized just how much fake love and true hate I was reflexively putting out into the world. I had a new interpretation of “fake it until you make it” Instead of faking success I tried to fake loving my enemies until I actually started to feel less hate. I wouldn’t be screaming at drivers on the road (as much), I stopped being obsessed with rooting against my competitors, and people on social media who I viewed as “unworthy”. I even tried to stop hating President Trump. I’m still working on that one. Still several times a day (every day) I have to literally stop myself and say out loud “stop hating!”, or “you’re such a hater!”. Like an alcoholic this might be a lifetime battle, but as they say knowing is half the battle. Now instead of seeking external validation I will never find, I have shifted my gaze within to find the happiness I deserve.


If the past is prologue then I’m guessing at some point I’ll take this new outlook on life just a bit too far before I inevitably have to pull back. My friends and family think I’ve gone way past that point already. Here are a couple of traps I might want to avoid…

  1. How do I distinguish what I consider healthy impulses (the desire to connect, the need to express oneself, or the desire for my basic survival needs), from the unhealthy ones (The desire for social and financial capital as a validation of my happiness)?

  2. How do I avoid hurting the people I care about that might bear the brunt of my actions? Just because I’m finding less meaning in financial and social rewards this does not mean that everyone else will. And if my new measure of happiness, which includes seeing others gain the same freedoms and happiness I am experiencing. The truth is I won’t be totally happy if those around me aren’t as well.

The truth is I don’t know how I’ll navigate these challenges.


Yes that little detail. The challenge I get from most who disagree with my new approach usually takes some version of the statement below…

Being charitable is great, but why put my business at risk? Why not just be charitable in private? Why not wait until I’m in a better position to give? I lean on a passage of scripture as my retort…

if you want to be perfect, go, sell your possessions and give to the poor, and you will have treasure in heaven

Matthew 19:16-30

Even as a child growing up in a strict religious household I could grasp the message in this parable. (Spoiler alert - even the rich man in this parable knew better than to “sell his possessions). I believe that once you have fulfilled the basic needs portion of Maslow's Pyramid, that the only thing separating us from experiencing the type of happiness associated with giving is to give, give and give until it hurts (As my dad use to say).

In an ironic twist, the researchers found that there is one thing that decamillionaires can do to get even more happiness -- give it away.


As I see it now, as I transition away from my pursuit for material and social validation, I hope to be able to leapfrog the whole “getting rich and famous” part and right into the “give it away” part that make the super-rich so super-happy. Why should millionaires and billionaires have all the fun of being uber-charitable? I half-jokingly ask myself.

The truth is if I’m not promoting the same kind of growth I am experiencing personally in my company, then I feel like I may be missing an opportunity that I may never have a chance to experience again.


Here is a truth that I think proves I am not a crazy person.

Every entrepreneurial fiber of my body is revolting against this new direction (in particular Pay It Forward Friday) like an addict going through withdrawal.

I hope that on the other side of this pain I will find something that I haven’t discovered in myself before. The kind of growth that sometimes only can be achieved through real pain. In the few months that I have been on this path, I have experienced the type of growth I haven’t experienced since I abandoned my childhood religion in 1991. The result, a discovery of self that is a direct result from the pain of giving, and a new measure of happiness. To ignore this path or to promote anything less in my business would give life to the cancer of unhappiness and allow it to come out of remission.


Maybe I’m just a stubborn and idealistic dreamer with my head in the clouds hell-bent on clinging to a non-existent point. That is if bankruptcy doesn’t cling to me first.


Maybe I am in ironic pursuit of exactly the type of social and financial validation I am positioning myself against. Am I secretly hoping to become the next Accidental Billionaire? Would that really be so bad?

Whether I soar or I crash, I hope it is a journey worthy of the pain and humiliation I’m putting myself through by pulling back the curtains for you to see me, warts and all.





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Raised to date

Raised to date

PS: My cousin said

You know, you are kinda hazing yourself by doing this in public. You missed it in college but you are getting it now.

I lmao’d