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The average middle class individual earns an income, pays taxes on that income and then they spend what is left. In our perfect-world financial model, they would use the eroded scraps to buy assets.
The rich on the other hand, earn an income, spend out of that income and then pay taxes on what is left over, quite the opposite situation. This gives them a higher disposable income to buy and build assets which in turn leads to greater wealth accumulation and an early exit into retirement if they so choose. The way they do this is through a business.
A business earns an income, spends and is then taxed on what is left over. Thus, your strategy is as follows. Start a small business, perhaps by upgrading a hobby into a small business, and then convert as many personal expenses as legally possible into business expenses. Your chart would thus look like this:

In one sense, it appears that you would still be taxed before the expenses slide over. But this is not the case. The expenses are subtracting from your business income and as you will see later, a business loss can be applied to your normal income for a limited amount of years.
Ultimately, you should apply your newly found savings towards purchasing cash generating assets. The ultimate goal is to purchase enough passive income generating assets to cover your expenses. Once you have obtained this goal, you can kick back and retire. With expenses of $2000 a month and passive income of $2000 a month, your chart would thus look like this:




Because of this status:
•100% on the road expenses are deductible (hotel, dry cleaning, tips)
•100% travel expenses (airfare, car rental)
•50% on the road expenses (applies to food)
To audit proof your travel, document the following:
1.) The amount that you spend daily for such things as transportation, meals and lodging.
2.) The dates of your departure and return home from each trip and the days spent on business while away from home.
3.) Where you traveled, describe the name of the city, town or similar destination.
4.) Why you traveled, including the business reason for your travel or the business benefit derived or expected to be gained (as specific as possible).
5.) Preexisting business intent: correspondence sent to prospects, documented phone calls, appointments in advance, etc.
Home Office
According to Soliman vs. the US Supreme Court – the leading precedence on home office business deductions, anyone who truly works out of his or her home and performs his or her most important functions at home can take the home office deduction. This would include network marketing, freelance writers, musicians who do most of their practicing out of their homes and consultants who do most of their important work out of their homes.
First and foremost, you office must be used solely for business purposes. You cannot have a guest bed, a book shelf containing books not related to your business a treadmill or a box of the kids’ toys. The IRS is pretty stringent about this and yes, it is possible that they will check and disallow your deduction if you do not meet the requirement.
There are three methods that you can use to figure out how much you can deduct.
• Method One: the amount of office square feet divided by the total usable square footage of the house.
• Method Two: the number of rooms the office occupies divided by the total rooms in the house.
• Method Three: Net square footage method (similar to method one except you subtract out the common areas such as hallways, entranceways, landings and stairways.)
Run the numbers and use the approach that leads to the biggest deduction for your situation. You might want to consult your accountant on the home office business deduction since you run into home depreciation recapture complications when you go to sell your home if you take this deduction.
Also, don’t forget you can deduct more rudimentary things such as office supplies, computer DSL, broadband, phone used for business and of course the cell phone bill used for business. In my opinion, these are more of your straightforward, typical business deductions and should not be subject to intense securitization. Still, keep those receipts.
Audit Proofing, Recapping and of course, Ralph
Just to restate the initial premise of why you should turn your hobby into a small business, the rich are getting richer through legal, justifiable tax breaks via their businesses and now, after reading this piece you can do the same. By aggressively shifting as much of your personal expenses into legitimate business, tax deductible expenses, you can take advantage of a plethora of tax breaks allowing you to retain more income in order to acquire assets that will provide you the ability to exit the rat race at an early age.
By taking action on the information detailed above you can deduct meals and entertainment, associated entertainment, charity events, home entertainment, vacations and your home office. If you are considering starting a small business, these tactics alone will give you an immediate initial leg up in your venture – you will already be employing a money making strategy off the bat or at least, a money saving strategy. If you are looking to increase your net worth or cash flow, this strategy of starting a small business will allow you to keep more of your income in order to build your assets.
Audit Proofing
In real estate the most overused, expert advice catch phrase is “location, location, location.” In small business tax deduction strategy, it should be “documentation, documentation, documentation.” If you are going to be aggressive about your tax deductions (and you should be) then you need to ensure you can sleep well at night by having ample documentation to backup your deductions.
Documentation requirements:
• Keep All Receipts
Although you are only required to keep receipts for expenses over $75, keep them all. I actually like to keep all receipts, personal and business, noting on the receipt whether it is personal or business and then what category it falls under. According to Robert Allen in “Multiple Streams of Income,” by doing this, in addition to verifying that the receipt is accurate, you can save tons of money over the years.
• Log Your Time
Keep a business journal denoting what date you worked on your business, how much time you spent and what activity you performed. The whole key here, along with creating a business plan and financial projections, is that you want to prove you are running your business as a business. One of the biggest tactics of the IRS is to classify your business as a hobby thus disqualifying most, if not all of your deductions. You want to insure against this by documenting the time you spend in your business – and don’t backdate a journal at the end of the year. Log it as you go along.
Also, it is better to work an average number of healthy hours per week, say 15 to 20, rather than cramming in 40 hours all at once at the end of the month. The first communicates that the individual is putting steady time into growing their legitimate business. The second communicates that person might not actually be tracking their time and is instead bulk loading it at the end of the month thus a red flag. Don’t do this.
• Audit Sheet for Expenses
As I said earlier, there are 5 questions you need to answer for deducting business meal and entertainment expenses. Again, these are:
1) Who was entertained and what is the business relationship? Id the person or persons, name, occupation, official title and other corroborative info to establish the business relationship.
2) Where did it take place? - get a receipt. The nature and place must also be described.
3) When did the entertainment take place? Note the date and time in a tax diary.
4) Why did the entertainment take place? Note the business purpose – state the exact nature of the business discussion or activity. “Talked about using my services – consulting on property investment.” Be brief but be very specific.
5) How much did it cost? A receipt will cover this.
Also, you should track travel details including hotels and overnight expenses. For a really great log sheet product, visit Sandy Botkin’s website at http://www.taxreductioninstitute.com/. This site has a tax log product that will help you document the 5 questions for meals and entertainment as well as travel expenses.
• Mileage Log
Make sure you track business mileage in any standard mileage log book you can get at any of your local office supply warehouse.
• Documentation for Travel
Again, with business travel, make sure you capture supporting evidence proving business intent for the trip; business appointment e-mails, business cards from the trip, MLS listings, room rate cards, etc.
• Show a profit 3 out of 5 years
You can lose money and apply the loss to your regular income but you must show a profit for 3 out of 5 years to prove profit intent. If you run it at a loss for many years it will prove to be just that, a tax write off and your deductions will be disqualified.
•Intention to Make a Profit
Through documents such as a business plan a financial plan showing growth and eventual profit, you need to prove that your intentions are to make an eventual profit. These supporting documents would serve as the proof in the pudding.
Books and Resources
•Lower Your Taxes - Big Time! 2007-2008 Edition (Lower Your Taxes Big Time) – Sandy Botkin
Next Steps
• Find an accountant – tell him or her what you are up to and that you plan to use him at the end of the year. See how he responds when you tell him the types of deductions you want to take. If he’s favorable or favorable but somewhat cautious, then he is probably a good candidate. If he has no clue as to the tax deductions you are talking about, move on to the next person.
• Read up on starting a small business and what applicable tax deductions you can take.
• Open a business checking account. Remember you need a federal EIN number if you are not a sole proprietorship or a single owner LLC. In those cases a social security number will suffice.
• Write a business plan. This along with financial projections, is great audit proofing documentation. It shows business and profit intent. There are reams of books on this subject.
• Get on a budget – find your monthly expenses and figure out how much passive income you need to become financially independent. Set a goal for when you will be out of the rat race. Do not count on your employer to take care of your finances. It is up to you.
• Take Ralph to TGI Friday's, tax deductible of course.

I always thought it was a bit too simplistic to say that "greed" was one of the major causes of the massive, subprime financial failure, but the more I read about it ... it is apparent that greedy folk are abound on this planet. (And I don't mean greed as it applies to achievement. To me these are diametrically opposite beasts.) One article I read details the speech of a banker admitting that free checking is a "tax on poor people" because they, the bank's, counted on collecting fees through overdrafts and add-ons.
The sub-prime mortgage market allowed investors to tap into the largest asset base in the states, the home, and although one of the supposed key tenets was to allow home-owners to tap into cheaper interest money, it was like handing a loaded gun to a four-year old.
And then you enter the genius and stupidity of Wall Street. The genius side of the coin (which could arguably still be placed on the stupid side of the coin) came from the folks who invented the subprime mortgage tranches, credit default swaps and the "geniuses" at Goldman Sachs who came up with the CDOs. My understanding is that the tranches and CDOs were ways to hide the junk, B- mortgages mixed in with the not so blatantly, festering junk. The bond tranches were set up like a parking garage (house of cards or stack of dominoes, your pick) with the riskier, substandard loans on the bottom and the better ones on top. The folks on the bottom received the highest interest rates but got wiped out first. Yayyy.
Enter the Genius of Goldman Sachs.
To further mask just how crappy these bonds were, Goldman Sachs started using the CDO or collateralized debt obligation which is essentially subprime bond towers (tranches) within a tower ... or in other words and even bigger house of cards.(stack of dominoe’s etc.)
At this point I would argue that the financial world might not have been devastated by a nuclear bomb had things stopped here but ...
Enter the Genius of Those Who Caught On ...
At this point if you were privy enough to realize just how big the subprime market was ...
“Thirty billion dollars was a big year for subprime lending in the mid 1990s. In 2000 there had been $130 billion in subprime mortgage lending and 55 billion dollars’ worth of those loans had been repackaged as mortgage bonds. In 2005 there would be $625 billion in subprime mortgage loans, $507 bilion of which found its way into mortgage bonds. Half a trillion dollars in subprime mortgage - backed bonds in a single year.” - Lewis, p 23.
And where it was headed, you might just start betting against the subprime mortgage market.
Enter the Credit Default Swap
A credit default swap is essentially insurance on a mortgage bond, insuring against default. The trick is, banks weren't buying them, they were selling them! The individual holding the default swap stood to gain massively if the subprime mortgage market imploded in on itself. Selling a default swap just meant extra income via the insurance premium to the seller.
Enter the Stupidity of AIG
AIG, through the wrangling and tactics of Golman Sachs began selling these things by the bucketfuls and by bucketfuls I mean billion dollar buckets. AIG was taking the other side of the bet and as long as the bank that held the original bond did not collapse, the person who bought credit default swaps stood to gain massively.
I would argue that a few key individuals truly turned a financial crisis into a global thermal nuclear financial meltdown. Had the credit default swap market not have taken off (e.g. those that wanted to buy essentially built the market by talking the banks into building and selling credit default swaps) and the insurers (AIG) not been so blind as to sell these things, I doubt we would still be experiencing the implosion of the housing market today.
In keeping with Malcolm Gladwell's proposition of the "Law of the Few" in which "the success of any kind of social epidemic is heavily dependent on the involvement of people with a particular and rare set of social gifts,"1 as detailed in The Tipping Point, I would argue that the exacerbation of the financial crisis was caused by a few key individuals.
1.Gladwell, p 33.
“A capacity, a taste for reading, gives access to whatever has already been discovered by others. It is the key, to the already solved problems. And not only so. It gives a relish, a facility, for succesfully pursuing the (yet) unsolved ones.”
- Abraham Lincoln, Address before the Wisconsin State Agricultural Society, Milwaukee, Wisconsin, September 30 1859
Apples to Apples
A duplex cash flowing at $5,000 a year on top of a $50,000 investment is providing a 10% rate of return (by the way, rate of return and return on investment are the same damn thing), a superior investment compared to a duplex cash flowing at $7,000 a year on top of a $100,000 investment for a 7% return.
A stock consistently delivering an average 20% return on equity, in Warren Buffet’s opinion, is in essence delivering a 20% rate of return. He claims this return as his. (more on this later.) A dividend stock paying an annual yield of $.70 with an average price of $10 a share is delivering a 7% rate of return. A business with $20,000 in earnings for the year and an initial investment of $100,000 is yielding 20%.
In the world of small business and investing, rate of return (return on investment, same thing) reigns supreme.
Investing From the Business Perspective
To further illustrate rate of return and how it applies across investments including small business, let us step into the shoes of a rental property investor. A true rental property investor evaluates property based on cash flow and the rate of return. The following table details a cash flow analysis of three sample rental properties, a triplex, fourplex and duplex respectively. The combination of a down payment, closing costs and repairs equal the total down payment needed to invest in each of the three properties. These are culled from real deals folks, so don’t accuse me of making up some hokey numbers.
| | 1625 Flanigan | 1717 O'Shea | 1714 O’Brian |
| Number of Units | 3 | 4 | 2 |
| Purchase Price | $ 100,000 | $ 128,304 | $ 97,200 |
| Cash Put In Property | | | |
| Down Payment | $ 20,000 | $ 25,661 | $ 19,440 |
| Closing Costs | $ 200 | $ 500 | $ 500 |
| Repairs | $ 550 | $ 500 | $ 200 |
| Total Cash Put Into Property | $ 20,750 | $ 26,661 | $ 20,140 |
| | | | |
| Monthly CF Analysis | | | |
| Monthly Gross Rental Income | $ 1,275 | $ 1,980 | $ 1,350 |
| Minus Vacancy Loss of 8% | $ 102 | $ 158 | $ 108 |
| Total Income | $ 1,173 | $ 1,822 | $ 1,242 |
| | | | |
| Mo Expenses | | | |
| Property Mgt Fee of 10% | $ 117 | $ 182 | $ 124 |
| Accounting | $ 10 | $ 15 | $ 5 |
| Insurance (hazard) | $ 50 | $ 54 | $ 50 |
| Yard work | $ 15 | $ 20 | $ 15 |
| Repairs and Maintenance | $ 90 | $ 120 | $ 90 |
| Misc. | $ 10 | $ 15 | $ 10 |
| Reserves | $ 20 | $ 20 | $ 15 |
| Taxes (Property) | $ 100 | $ 139 | $ 95 |
| Total Expenses | $ 412 | $ 565 | $ 404 |
| NOI | $ 761 | $ 1,257 | $ 838 |
| Loan Pmt | $ 675 | $ 866 | $ 656 |
| | | | |
| Cash Flow | $ 86 | $ 391 | $ 182 |
| | | | |
| Rate of Return | 5% | 18% | 11% |
Table 1-1
