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205. Why Congress Provided for Monetized Installment Sales

204. Here's How to Do a Financial Analysis of the Probability-weighted Benefit and Tax Risk with M453

203. If a Seller Uses a Monetized Installment Sale (M453), Can the Resale Be an Installment Sale, Too?

202. Solve the Double-Tax Problem for Earnings of C Corporations with a Long-Term Installment Sale Coupled with a Monetization Loan

201. When You Can, and When You Canít, Change a Deal after the Fact, for Better Tax Treatment

199. Are We Really Able to Hear Each Other? Or Are We Locked in by What We're Sure We Know?

198. C453 is Presented in Meeting of Professionals, Principals and Advisors Connecticut

197. An Insured Can Defer the Tax on Sale of a Life Insurance Policy, But Partly on One Ground, and Partly on Another.

196. Liquidate a ďCĒ Corporation with Minimal Tax Cost, with C453

195. Hereís a Strategy for Your Benefit if Your LLC Partners Donít Need Tax Deferral when Your LLC Sells

194. With C453, Help Yourself and Your Favorite College, University or Other Charity, Too

193. The Doctor, the Tardis, Time Travel and Taxes

192. Find Out Whether a 1031 Exchange or a C453 with a Monetization Loan is the Better Choice for You

191. U.S. Bankruptcy Court Approves C453 for Sale of High-Value, Low-Basis Asset

190. With Higher Tax Rates, Our Business Enjoys a Substantial Uptick, Both Overall and in Deal Size

189. Can C453 Be Used for Sale of a Business to an ESOP?

188. "Who Gots It Don't Want It": 1099-MISC Income and Schedule D Income

187. Defer Tax on Commission Income, and Increase Your Disposable Cash Flow

186. IRS Chief Counsel Blesses Tax Deferral through an Installment Sale Coupled with a Monetizing Loan

185. Can a Residential-subdivision Developer Obtain Capital-Gain Treatment on Lot Sales? And Defer the Tax, Too?

184. A 1031 Exchange Scandal: Who Cares about the Taxpayer?

183. Can C453 Repeatedly Achieve Tax Deferral for the Same Money, As in Hopscotch?

182. Business-Normal Practice to Know Your Counterparty: Coherence, Reasonableness, Verifiability and Understandability

181. Keep Your Romance Alive, with Some Help from C453

180. C453 Can Avoid a Tax Hit on Disposition of Assets on Divorce, and Simplify Division as Well

179. Liquidate U.S. Investments and Invest the Gross Proceeds Internationally, without Having to Pay U.S. Taxes First

178. Sell Capital Assets without Current Tax Cost; Make Tax-deductible Gifts to Charity; Reduce Tax as Well as Defer; and Substantially Increase Cash Available for Other Uses

177. An Occasion for Sadness: When Advisers Let 1031 Exchanges Fail, or Cause Them to Fail

176. Does an Installment Sale Defer the Tax on Recapture of Accelerated Depreciation? No. Can the Tax on Recapture of Accelerated Depreciation Nevertheless Be Deferred When an Installment Sale Occurs? Yes.

175. Should You Choose a 1031 Exchange, or a Collateralized Installment Sale?

174. When to Use a Collateralized Installment Sale (C453) with, or in Place of, a Charitable Remainder Trust (CRT)

173. Hear about Collateralized Installment Sales on Smart Money Talk Radio Nationally on Monday, January 28

170. Will the New 3.8% Investment Tax and the Higher Capital-Gains Tax Actually Increase the Government's Revenues?

168. The New 3.8% Medicare Tax Can Be Deferred in Installment Sale Transactions.

167. Four CPE Credits for CPAs, January 15

166. Twelve Days of Christmas Tax Readings

165. How an Installment Sale Reduces Estate-Tax Liability

164. With Tax Deferral, You Needn't Rush to Sell Before the Tax Increase on January 1

163. Not in Good Health, a Taxpayer Finds a Solution to the Dramatic Increase in the Estate Tax Coming on January 1.

162. Transfer a Family Business to the Next Generation During the Parent's Lifetime, Retain an Asset for Income, Give the Transferee a Stepped-up Basis, Defer the Gain on Sale, Support the Parent with Deductible Rent, and Finance the Transaction, Too

161. Use C453 to Eliminate Estate Tax and, with Life Insurance, to Transfer Assets and Cash to the Next Generation

160. The Price of Economic Uncertainty: 1% to 2% Higher Unemployment

159. A New Reason Why S.Crow Collateral Corp. Isn't Just Another Intermediary: Standing Advance Loan Commitments and Credit Enhancement for Our Sellers and Potential Sellers

158. How Markets Differ from Gambling and Pyramid Schemes

157. Here's a New Way to Achieve the Equivalent of Tax Deferral.

156. Don't Fence Me In: When Government Makes an Entrepreneur Feel Claustrophobic

155. Action Now Can Help You Cope with the "Tax Cliff" at the End of This Year.

154. A Case Study: Deferring the Debt-Over-Basis Tax (and Tax on Other Gain) when Encumbered Property Is Sold

153. Would You Like to Move to a Low-Tax State, without Paying an Exit Tax?

152. Here's a Better Solution for the Tax System and the Economy: A Graduated Retail Sales and Services Tax

151. Thinking Dangerously: When Docile Taxpayers and Their Advisers Give Away Legal Rights

150. For Doctors Who Sell Their Practices to Hospitals: Watch for Hidden Risks, Costs and Traps

149. An IRS Ruling and Collateralized Installment Sales

148. New Scientific Research Looks at How the Human Brain Deals with Taxes

147. The "Jevons Paradox", "Sustainability", Gasoline Prices, and Opting for Growth Rather than Decline

146. Why Our Sellers Want to Say to Us, "Please, please, don't pay, or at least don't pay now!"

145. How Does a Collateralized Installment Differ from a Deferred Sales Trust?

144. The IRS Has Issued Detailed Guidance on "Economic Substance". Let's Learn It and Use It.

143. Why Lenders Like to Lend to Those Who Sell to S.Crow Collateral Corp.

142. About Tax Advisers Who Think Installment Sales Equal Cash Sales. Sure, and I-95 Equals I-90.

141. Let's End the Confusion about the Tax Treatment of "Real" Transactions.

140. New Information, New Understanding and New Tools, Available Now, Avoid Regrets Later

139. Does Your Tax Adviser Read the Law, or Merely Read or Hear What Others Say the Law Is?

138. Avoid Tax at the Entity Level on Sale of a Business, Regardless of the Legal Form of the Entity

137. When Your Company Moves up in the Marketplace, the "Lake Erie" Criteria Help the Shareholders Select the Company's Board Members.

136. What Can Be Done for Tenant-in-Common Investors in Commercial Property Facing Foreclosure?

135. Can the Tax on Depreciation Recapture on the Sale of Equipment Be Avoided or Deferred?

134. Say It Isn't So: Political Risk Is Affecting American Business and Americans' Freedoms

133. No Dollar Limit Applies to Tax Deferral on Installment Sales of Agricultural Properties or Rights

132. How a Business Owner's Creative Thinking Led This Week to a Solution for Sale of His Business

131. CPI Rises to 3.9%, and Treasury Sees the Heaviest Bidding in 13 Years for TIPS; Maybe There's a Connection?

130. Today's Producer Price Index Report: Inflation Hits 0.8% in September (a 10% Annualized Rate)

129. For a Better Understanding of the Tax Code, Try Looking First at the Forest, Before Looking at Each Tree

128. Will the Now-Fainting 1031 Tax-Deferred Exchange Industry Ever Come Back?

127. The Flavor of the Week, Based on Customer Requests, Is the Looming Tax Cost of Commercial-Property Foreclosure.

126. Try to Be Calm about This News, But the Tax Problem on the Sale of a Business Is Solved.

125. The Federal Reserve Succeeds in Its Fight Against Deflation--But Inflation Rises.

124. Alert! Defer the Tax on Your Sales Commission Income, with DEFCOMM.

123. So, How Is That Advice That You Gave in 2007 Working Out?

122. Today's Market Rout, and When You Have Assets Which You Could Sell, But Not at a Price Anyone Is Willing to Pay

121. Selling Property at Auction Can Trigger Tax, Even if You Don't Net Any Cash--unless You Combine the Auction with a Collateralized Installment Sale.

120. Just the Facts, Ma'am: How to Minimize Tax-audit Fear.

119. How Can One Shelter Interest Income from Tax? Or Convert It to Capital Gain?

118. Follow These Practical Guidelines to Preserve Tax Deferral for Your Installment Sale, If You Borrow Money at the Same Time

117. The Government Has Painted Itself into a Corner Because of Debt, and Can Do Very Little to Help the Economy. The Private Sector Has Some Options Left, However.

116. Did You Hear about the 3.6% Tax Increase Just Now Quietly Announced? Or about the Further Tax Increase Coming Next Month?

115. How an Average Person Can Tell Effective Economic Stimulus from Ineffective Stimulus

114. Here's the Silliest Argument Yet, in Favor of Raising Taxes--and It Was Made With a Straight Face.

113. So, You Have a Property That's about to be Foreclosed. How Can You Save Your Credit, and How Can You Avoid Tax on the Excess Debt?

112. A Nationally Prominent CPA Joins in Conversation about Tax Deferral and Collateralized Installment Sales

111. Are There Hidden Costs Associated with a Collateralized Installment Sale? With Other Tax-Deferral Methods? What Is the Real Cost?

110. Will an Investment Adviser Prefer That a Client Sell in a Collateralized Installment Sale ("C453"), or in Some Other Way?

109. Will a Real Estate Broker Make More Money, or Less, with a Collateralized Installment Sale?

108. The "Economic Substance" Doctrine Is a Safe Harbor for the Tax Treatment of Your Transactions, So Use It.

107. Professionals Who Wing It, and Give Distorted Tax Advice

106. You Can Easily Avoid Tax on Relief of Debt. Here's How.

105. Set Sail Now--and Get Set to Sell Now--with Our Flagship

104. How Do You Feel--or What Do You Think--about the Whole Idea of Tax Deferral? Is It a Wholesome Activity?

103. A Done Deal: Seller Sells a Capital Asset and Defers Tax for 30 Years, But Has Equivalent Cash. How Can This Be?

102. "Wave of Frantic Consolidation in the Health Industry" Calls for Tax, Estate and Investment Planning, Now

101. Plan for Long-term Care, While Preserving Your Wealth with a Collateralized Installment Sale

100. How Do Pigeons, Innovation and Freedom of Contract Relate to One Another?

99. The Golden Egg: Create Your Own Investment Fund with MoneyThat Otherwise Would Be Required for Taxes

98. Subtle Deconstructionism Affects Legal and Tax Advisers, and You, Your Pocketbook and Your Freedoms

97. #2 in a Series: Announcement: You Participate in Loan Fees, And Everyone Benefits

94. #1 in a Series: Announcing: Tax Deferral with Complete Liquidity

93. Thank Heaven for Little URLs: One That Circumvents Tax-Deferred Exchange Problems

92. How Can the Seller Sell at 2007 Prices, While the Buyer Buys at 2010/11 Prices?

91. Buying a Property? Want to Reduce the Tax on the Lease Income after You Buy?

90. A Key to Growing Your Business: Use Your Knowledge of Yourself (Your Theme) As a Lens to See Opportunity

89. Better than an IRA: Pre-tax Money Buys "Underwater" Homes at Market or Less and Produces Income Not Taxable to You. Then You Finish by Deferring the Tax on Resale.

88. A Conversation about Saving a Particular "Underwater" Home Loan

87. Put Your Defense in Place Now, against the Estate Tax Beginning January 1

86. At Last: A Private-Sector Solution Shows up, for Underwater Home Mortgages

85. Are We There Yet? --Not Now, Not Later, if "There" Means Paying the Capital Gains Tax

84. A New Philosophy of Tax Benefits: How to Obtain Happiness and Tax Benefits, Too

82. Minimizing the Tax on Marcellus Shale Mineral Rights Income

81. "That's the way it's always been done."--How Government and Business Really View Innovation

80. Selling into a Down Market: Why Sellers and Buyers Should Stop the Waiting

79. "If only I'd Known Then What I Know Now": Q&A about Commercial Loan Portfolios, While There's Still Time.

77. Defer the Tax on the Sale of Your Business, and Pay the Tax Later in Cheaper Dollars

75. S.Crow Collateral Corp. in Business Week

76. How Can Your Bank Profitably Reduce Its Exposure to Commercial Real Estate?

74. Avoid the Power Trip: Don't Get Above Yourself

73. Two Moves Ahead: Playing Dynamically to Win in Today's Economy

72. Take a Number, for Bank-owned Commercial Properties: How the Bank Can Sell High, and You Can Buy Low

71. Reading the Warning Signs: Is Is Worth Trying to Do Business with a Narcissist?

70. On Being #1: A Largely Unobserved Incoherence about Innovation and Leadership, in American Business

69. Part 5: Is It a Gimmick, or Is It Worthy of My Time to Hear? It's *Not* Whom You Know

68. Part 4: Is It a Gimmick, or Is It Worthy of My Time to Hear? About Loopholes vs. Substance

67. Part 3: Is It a Gimmick, or Is It Worthy of My Time to Hear? About Black Swans, and Surprises

66. Part 2: Is It a Gimmick, or Is It Worthy of My Time to Hear? How Excited Is the Proponent?

65. Part 1: Is It a Gimmick, or Is It Worthy of My Time to Hear? The Role of a Stated Economics Rationale

64. In a Short Sale of Your Commercial Property, Why Not Pay Your Loan in Full?

63. We Can't Cause Market Values to Rise, But We Can Increase Your Equity Immediately

62. Let's Opt Out of a Decade of Stagnation in Commercial Real Estate Prices

61. It's a Roller Coaster around Here, As We Work with Those Who Are at the Top, and Those Who Were at the Top

60. A Rescue for TIC Investors in Troubled Properties or Who Just Want Out without Being Taxed to Get Out

59. The Ever-Present Logical "Fallacy of Division" in Public Discourse Makes a Dumb Argument Sound Good

58. I Sang for My Father: For Optimism in Opportunity

57. Red Flag #2 about DSTs: Invitation to a Conflict of Interest

56. About Clamor at Parties, to Learn about Tax Deferral or Resolving Troubled Commercial Loans

55. How Does a Collateralized Installment Sale Differ from a Sale to What Is Called a Deferred Sales Trust?

54. 1. Dealburt Retires. 2. "Regulatory-Risk" Aversion Will Reduce Economic Growth.

53. Ready for Prime Time: Our Criteria for Resolving Troubled Commercial Loans

52. What's the Easiest Way to Minimize Your Risk of Investment Loss? Postpone the Tax on the Previous Investment.

51. One Size Fits One: Because Every Situation Is Unique, Every Transaction Should Be Unique, Not a Formula

50. The Creative Process, Categorical Reasoning, and Tax Minimization

48. New: A Perpetual Collateralized Installment Sale: Permanent Tax Deferral in Unlimited Amounts

The Latest Installment

Are We Really Able to Hear Each Other? Or Are We Locked in by What We're Sure We Know?

January 8, 2015

       All right, it’s time that we talked this matter out:  a real heart-to-heart conversation in which each of us hears—really hears—what the other is saying.

      As I understand it, what you’re saying to me is that you are the attorney for the owner of a $100 million commercial building.  The owner has a tax basis of $20 million.  He wants to sell, and he doesn’t want to do a 1031 tax-deferred exchange; he’s done lots of those already, and now he wants an exit strategy—not just another trade, not just another property to manage, but a real exit without having to pay the capital gains tax now.

      When I say to you that your client should consider an installment sale coupled with a monetization loan (as the Internal Revenue Service calls it) as a tax-deferred exit strategy, you sort of blow me off.  (Pardon me for putting it so bluntly.)  You say that of course a $100 million installment sale won’t do the trick, because of the requirement in Internal Revenue Code Section 453A that the seller pay interest to the IRS on the deferred tax if the installment sale price exceeds $5 million per owner (unless it’s agricultural or personal-use property).

      I reply:  Here’s where it gets really interesting, but it’s also where it gets really difficult and requires some patience to hear me out.  What I’m saying is that the transaction components—although they are difficult—can indeed be put together in such a way that what would otherwise be a $100 million commercial-property sale can be done without the seller’s being required to pay interest to the IRS on the deferred gain.  Doing this requires the execution and performance of a set of transactions, each of which:

·       has substantial economic substance in its own right, quite apart from tax effects;

·       makes financial sense for each party, for that transaction alone and for the set of transactions taken together;

·       is undertaken for substantial business purposes and not just, or even primarily, for the intended tax benefits;

·       complies with applicable statutes, regulations and tax doctrines;

·       avoids original-issue-discount (OID) concerns; and

·       permits full tax deferral (including for depreciation recapture) for up to 30 years.

     Moreover, these transactions may well result in tax reduction for the seller, not just tax deferral.

     When you hear all of this, it may surprise you to learn that tax deferral is not even what drives all of this.  Yes, from your seller-client’s point of view, tax deferral may loom very large in his thinking, but what drives this is that these transactions—the installment sale coupled with a monetization loan—materially increase the risk-adjusted return for the lender with which S.Crow Collateral Corp. works (the lender which offers a monetization loan to our seller).  If you can really take this on board—that taxes aren’t everything, and that not everything you have always understood about lending is really the way things must always be—then a whole new vista of opportunity can be brought to your client.

     I emphasize again, though, that this is not easy.  It is difficult.  It is hardYou have to be willing to set aside what you know you know, and you must be willing to re-think.  If that’s not for you, let’s stop right now.  On the other hand, if you’re the one in 100 who is willing to re-think what you know, let’s continue the conversation.—Stan Crow

 

Photo credit:  http://www.flickr.com/photos/kdavidclark/4533381951/in/photostream/, Creative Commons Attribution 2.0 Generic License.  No changes were made.


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Stanley Crow, our Editor

The Latest Installment addresses situations, questions and issues which are brought to us in the course of the consideration, negotiation or execution of transactions. We don't use the real names of parties to transactions, and we may edit the statement of the question to try to tell the story better. Please feel free to comment, or to take issue, or to raise your own question or situation. If you do the latter, please do not relate any confidential information.

The Latest Installment blog is edited by Stanley D. Crow, who is president of S.Crow Collateral Corp.

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