I understand and agree that these expenses are not considered personal expenses for tax purposes, but what about for our purposes?
There are several examples:
Charity
It makes total sense to donate from the business. If he transferred the money to himself first, it would be considered business and personal income, and he would have to pay business taxes on it first, and if he reached his limit for personal charity deduction, then he would have to pay personal taxes on it too.
But in reality, either way, he is giving this money that belongs to him away from his business or his personal money. He could for example choose not to give to charity at all, from his business or personal money. I'm not saying that he should, I'm merely pointing out that he is giving money away to charity through his business and not counting it as spending.
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Vacations
He takes vacations and pays for them on his business' dime, then doesn't count it in his spending. Two examples I remember were vacations to Hawaii and Seattle where he would attend a conference for financial bloggers.
Again, legitimate business expense, but it was his choice to go and spend the money. And again, i'm not saying he shouldn't have, I am just asking, isn't this really a personal expense?
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Experiments and other discretionary business expenses
He often pursues optional hobbies or conducts experiments in the name of his business, and doesn't count them as part of his personal spending. One example is when he decided to conduct an "experiment" of blowing $1,000 in a week to find out what it feels like and to blog about it. This apparently included buying drinks for a bunch of people at a bar for something like $150 and buying a $12 piece of pie at an expensive restaurant.
he could have imagined,or just observed without spending himself, or forgone this experiment, and at the end of the year have an extra $1,000 in business income. It is his money and he is free to do what he wants with it, and everyone splurges once in a while, but I am asking whether this and other expenses like these should be excluded from his spending?
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These things could at least be considered quantifiable benefits to his employment.
Just like having a Job that provides a car, or provides housing, or provides health insurance, these things could be considered like having a job "expense account" or a credit card provided by and paid for by your employer.
These types of benefits may or may not be considered income for taxable purposes, but come on. If you have a job that gives you a car and a credit card that you use to pay for the car's gas with, and you get to drive that car personally, you would consider it to have a quantifiable value.
Lots of people with their own businesses find ways to pay for things with their business to save on taxes. If you use your business to pay for vacations and charity and spending experiments and funding hobbies, shouldn't you count that as part of your annual spending for your own purposes (though not for tax purposes) ?