Originally Posted by Rob.Singer View Post
Alan, I've got a little time so I'll give you more info on how I didn't need to pay taxes on any of my wiining as a professional gambler for the 11 years I did it. Of course, it's a different scenario since retiring from filing schedule C in each of those years, but I still pay zero taxes on my modest net winnings.

You're familiar with filing as a business. I was in business for myself as an author/writer, gambling advisor, and as a professional vp player. And as a filier of this status, I deducted a portion of my house in Phx., my home in Hawaii, and my apt. in Phx. Why & how? Because I lived, ate, slept and breathed vp during those years, and aside from my renting a car every day of the year each year that I deducted, along with all the gas and some insurance, whenever I was at a home I'd deduct travel there, food, dinners out even if I brought up gambling for an instant or for hours, etc. etc. etc. Take my wife to dinner and discuss my upcoming schedule for my travel to Nevada for the next week? Deductible. Buy groceries that helped keep me going all those endless hours at the computer writing? Deductible. I had some people I trained over to my house in Phx., and I liked to entertain them at the pool & spa while we talked "business". Bottom line, much of the expenses in my life were deductable legally, and my audits supported that. Outsiders may see this as a stretch, but they are all loophole-safe. My son-in-law also works for the IRS as a manager/Agent, and I made sure I followed the guidelines as required, as far along the edge as some of my deductions may have been.
You've got me scratching my head over a lot of these "deductions" Rob. I have a business and I discuss business and do business over dinner and while eating and while in my car but I must say I am not as "loose" about what I claim as a deductible expense.

Frankly, I have an office in my home and I don't deduct it. Why? Because my office in my home is not exclusive to my business. I sometimes conduct business in my home, via email and writing scripts, while eating at my desk. Do I deduct the cost of the food I am eating at my desk while writing a script or planning a show? No, I don't.

I discuss my upcoming TV shooting schedule when I am out to dinner with a friend or my wife and problems I have with a client and mentioning that I have a new client and I might ask "what do you think about this product?" Does that make it a "business meal" and worthy of a deduction? I don't think so.

When I am shooting an Infomercial and we drive 240 miles in a day going from location to location, yes, we deduct those miles. But my car is also used for personal use and so my car is not a business expense. The business miles are a business expense.

I write an article here about changes I saw at Rincon. Does that make the trip to Rincon a deductible expense? In your eyes, perhaps. Not to me.