Anthony McCann1 360x1000
Margaret Fuller3 360x1000
Thomas Piketty3 360x1000
2theleastofus
1jesusandjohnwayne
3paradise
1lookingforthegoodwar
Margaret Fuller 360x1000
4confidencegames
3defense
2defense
Margaret Fuller 2 360x1000
499
2albion
Office of Chief Counsel 360x1000
George F Wil...360x1000
299
1trap
2lookingforthegoodwar
2jesusandjohnwayne
Margaret Fuller4 360x1000
11632
1madoff
2confidencegames
Mark V Holmes 360x1000
12albion
10abion
Susie King Taylor2 360x1000
lifeinmiddlemarch2
2trap
1lafayette
storyparadox2
Brendan Beehan 360x1000
2gucci
Thomas Piketty2 360x1000
AlexRosenberg
Gilgamesh 360x1000
1albion
2lafayette
14albion
George M Cohan and Lerarned Hand 360x1000
Margaret Fuller2 360x1000
Spottswood William Robinson 360x1000
Tad Friend 360x1000
1falsewitness
1defense
Susie King Taylor 360x1000
2falsewitness
Richard Posner 360x1000
Anthony McCann2 360x1000
Margaret Fuller5 360x1000
Lafayette and Jefferson 360x1000
9albion
3theleastofus
Maria Popova 360x1000
Stormy Daniels 360x1000
1gucci
5albion
11albion
Ruth Bader Ginsburg 360x1000
Thomas Piketty1 360x1000
8albion'
1transcendentalist
LillianFaderman
5confidencegames
1lauber
Betty Friedan 360x1000
7confidencegames
3albion
1confidencegames
1theleasofus
6albion
Margaret Fuller1 360x1000
7albion
Edmund Burke 360x1000
13albion
Maurice B Foley 360x1000
1empireofpain
Storyparadox1
Samuel Johnson 360x1000
lifeinmiddlemarch1
James Gould Cozzens 360x1000
2paradise
1paradide
Mary Ann Evans 360x1000
3confidencegames
6confidencegames
199
Learned Hand 360x1000
storyparadox3
Adam Gopnik 360x1000
4albion
2transadentilist
399
Originally Published on forbes.com on July 17th, 2011
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I’m not one for keeping the names of actors straight, so the name John Ratzenberger doesn’t really stick in my mind.  Cliff Clavin, the postal employee, is of course another matter.  Everybody knows his name and that of his best friend Norm Peterson, who at one time was an accountant.  When David Aliotomet Mr.  Ratzenberger, they came up with a business plan that could plausibly have been the result of a brainstorming session of the Cheers regulars:
The business concept was to use celebrities, such as Mr. Ratzenberger, and create media which would then be sold to corporations to advertise on the Internet. Mr. Alioto testified that a business plan named Big Rent Tent (BRT) was developed, which included multiple celebrities. Mr. Alioto became CEO of BRT around September 2000.
I don’t know, maybe it wasn’t such a bad idea.  Execution on the other hand was definitely not good.  Mr. Alioto advanced $103,150 to the BRT.  When he found out that nobody else was committed to putting in any money, he abandoned the project.  That was in 2001.  He made no attempt to recover the money from anyone.  In 2005, Mr. Alioto went through personal bankruptcy.  Included in his assets was a claim against BRT and Mr. Ratzenberger in theamount of $313,363.  The bankruptcy trustee did not attempt to recover anything on that “asset”.
Sometime in 2005, Mr. Alioto received an e-mail from Mr. Ratzenberger’s financial manager indicating that Mr. Ratzenberger was not going to reimburse him.  Sadly we don’t have the text, because Mr. Alioto could not produce a copy of the e-mail for the tax court decision, that gave us this story.  Based on the e-mail, Mr. Alioto claimed a theft loss deduction for 2005, which carried over to 2006 and 2007.
Mr. Alioto lost in Tax Court.   Most of the evidence indicated that he knew that he was not going to recover anything from BRT as early as 2001.  Further the Court went to great length to indicate that no aspersions should be cast on Cliff, I mean Mr. Ratzenberger:
There is nothing in the record that would prove that Mr. Ratzenberger committed any wrongdoing. Mr. Alioto did not present any evidence demonstrating that Mr. Ratzenberger or his agents did anything illegal and failed to show any specific promises or agreements made by Mr. Ratzenberger and his agents. Mr. Alioto never contacted the police, the Securities and Exchange Commission, or any State licensing division, never filed suit against Mr. Ratzenberger, and never had any written contract between himself and Mr. Ratzenberger. At trial Mr. Alioto claimed that a formal agreement did exist between himself and Mr. Ratzenberger but that he had left it at home and did not want to share it with anyone.
The Tax Court did cut Mr. Alioto a little bit of a break.  They did not sustain penalties:
We believe that Mr. Alioto did in fact make a good faith effort on the basis of his knowledge of the facts and understanding of the law. Mr. Alioto is not a tax expert, nor has he any background in tax law. Respondent does not dispute that Mr. Alioto incurred $103,150 of expenses. Neither does respondent dispute that Mr. Alioto was involved in a complicated business transaction. Mr. Alioto sincerely believed he was shorted $103,150 in this business transaction, and he genuinely believed he was entitled to some income tax relief. Thus, given these difficult circumstances, we find that the claims of losses were made with reasonable cause and in good faith. Accordingly, we do not sustain respondent’s imposition of accuracy-related penalties for tax years 2005, 2006, and 2007.
There are two tax lessons here.  The first is that if you are going to use documents to support your position you have to hang on to them and be willing to show them to people, like IRS agents and the Tax Court.  The other is that losses need to be claimed at the earliest reasonable time to avoid being whipsawed by the IRS.  The business lesson is a new evaluation technique.  When you have an idea, mentally run it by the crowd at Cheers.  If you think they would be enthusiastic about it, pass.