Ok — hear me out.

This was an idea drunkenly shared at a party among friends that I thought would be hilarious as a really “scammy”, but seemingly legal way of avoiding taxes. First and foremost, I’m relatively successful and have a lot of things I’m blessed with in my life so if that’s going to bother you, I’d suggest moving on :). This post is intended for fun and is an attempt to explore the intricacies of creating a charity, what qualifies as a donation, and where I fall ethically and morally on the subject. Anyways, let’s get started.

So, let’s start with Men’s Mental Health. A term that some hate in this day and age, but a real problem when analyzed <link>. The term to me refers to the large and growing portion of the population of men who struggle with mental health. As someone who has admittedly dealt with these struggles at different points of my life; I’ve drawn the conclusion to what the root of the problem is for me. It’s loneliness. Throughout the low points in my life, I’ve felt alone. Lacking closeness and companionship to my fellow human, community, etc. When I would see others with a lot of people in their life I would think “how lucky are they to have such a great set of people around them?”. it would often come in the form of being on the beach, at a party, at the bar, or some event having a great time. So where am I going with all of this? We can solve a ton of men’s mental health issues by curing loneliness. Curing loneliness could come in the form of an event at a beach, a party, night at the bar, or some type of event! You can see where I’m going with this.

I don’t want to sound like the next “Men’s Mental Health Influencer”, but this idea gets interesting in terms of how far you can blend the lines of writing off your drunken bachelor expenditures and what constitutes a Men’s Mental Health “Charity”. It also poses the obvious question of “Is this the guise men’s mental health influencers operate under?” even more so “Is this the guise most *influencers* operate under?”. Write. Off. Everything. I suspect there’s some truth to that. However, most of those influencers still had to earn their income and savings from the ground up around their business or personality. Meaning, the things they write off are actual business expenses. The situation I’m describing is a little different and much more legally, ethically, and morally grey.

I’m asking: What are the legal, moral, and ethical lines of creating a charity? Within that framework: What are the boundaries when donating your own assets intending to maximize your usage of them in a way that is acceptable? Put simply, I want to donate my yacht and cars to my own charity and use it for Men’s Mental Health parties and events, while writing off the donation from my taxable W2 income. If I haven’t lost you by now with how pompous this post is and how absurd it is, welcome to Words of Will and I appreciate you taking the time to read through this!

So what would the Charity need to be called? For Men’s Health? Sounds a little too direct. Maybe something more subtle that could sound like a cool club or something. FMH could do — I’m a partying bachelor, I want to share this lifestyle with people but not draw too much attention to it as it will likely receive scrutiny. Right off the bat there is the first conundrum. Although there is no legal requirement for a charity to advertise or make a well known brand as far as my research takes me, I will give a quick piece of advice for anyone thinking of doing this. If you’re asking these types of questions, it’s likely some form of fraud 🙂 so don’t do any of this. But let’s say you really felt passionately about this societal issue and wanted to do this. Is a charity required to advertise, from a moral and ethical point of view?

Let’s continue with FMH. I’ve founded my charity, I’ve donated my supercars and yacht to it, I’ve written off those as donations to charity claiming back my juicy 37% of their value, and I’m ready to host my first event. Well, FMH believes that partying and bonding is the best way to avoid loneliness and therefore improving Men’s Mental Health for those involved. That means a large party or event is the way to go! Why not use my yacht to host? That means the yacht fuel, crew, maintenance, and most importantly booze and food are all write offs in addition to donating the cars and yacht I’ve donated already! Of course, these events would be something I would host anyway since I’m living this lifestyle every day. This would simply be a way to save a significant portion of that in taxes back!

Is a charity a charity because you believe you are doing good for your cause? Or is a charity a charity because society believes it’s valid from a social contract perspective? Does an individual doing these things need a charity and the tax benefits? Who am I to judge the validity of a charity? If I can’t, why should someone else? I’m certain I can find a lot of charities that are not doing actual charity and are purely in existence for tax purposes.

Any who. Those are the questions I’ve been pondering on this subject. Let me know what you all think!