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Matthew Sherman specializes in both civil and criminal tax controversies and serve as the Tax Workout Group firm’s practice group leader for all tax-bankruptcy matters. He handles both Federal and state tax matters involving individuals, corporations, partnerships, limited liability companies, and trusts and estates.

In the tax controversy arena, Mr. Sherman has considerable knowledge and insight handling complex civil tax examinations, administrative appeals, and tax collection matters. His tax practice includes a wide array of dispute types involving income taxes, sales and use taxes, employment taxes, excise taxes and property taxes. He thinks of himself as a tax controversy expert who aggressively represents taxpayers in all deficiency, refund and collection defense matters.

As the group leader of the tax bankruptcy practice group, Matthew ensures all tax-motivated bankruptcies achieve one goal - the elimination or favorable resolution of all tax claims in bankruptcy.

Tax Law

Business Taxes, Criminal Tax Litigation, Income Taxes, Payroll Taxes, Property Taxes, Sales Taxes, Tax Appeals, Tax Audits

Bankruptcy

Chapter 11 Bankruptcy, Chapter 13 Bankruptcy, Chapter 7 Bankruptcy, Debt Relief

• Tax Bankruptcy - focused on the discharge of tax claims in bankruptcy.
• Tax Controversy - focused on the resolution of tax claims.

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Florida

The Florida Bar

ID Number: 1038794

U.S. District Court, Middle District of Florida

U.S. District Court, Northern District of Florida

U.S. District Court, Southern District of Florida

U.S. Tax Court

Attorney

Tax Workout Group, P.A.

Current

Practice Group Leader - Tax Bankruptcy and Tax Controversy.

Accountant

Better Life Products Investment Group, Inc.

2016 - 2018

Worked within the accounting group performing accounting, tax and legal support related matters, administrative, and human resource functions for this growing company, including invoicing, product receipt, inventory control, vendor payment, account reconciliation, and other admin related tasks.

University of Florida

B.S. | Accounting

Nova Southeastern University

J.D. | Law

Honors: Magna Cum Laude. Dean’s List (Winter 2019, Fall 2019, Winter 2020, Fall 2020, Winter 2021)

Activities: Recipient CALI for Future Excellence Award, Income Tax

University of Florida Levin College of Law

LL.M. | Taxation

CALI Excellence for the Future Award, Income Tax

Shepard Broad Law Center, Nova Southeastern University

The Florida Bar  # 1038794

Attorney

Current

Can Trustee Avoid Federal Tax Lien Against Debtor’s Exempt Property in Bankruptcy?

Tax Workout Group

January 22, 2023

IRC section 6751(b) – A Sword and a Shield – Depending on Who You’re Asking

Tax Workout Group

January 5, 2023

Certified Public Accountant

Florida Board of Accountancy

Q. When hiring a CPA , who is responsibile for knowing the law?

May 17, 2023

A: Both. Yes.

Q. Can I convert a Chapter 13 to a Chapter 7 before the meeting of the creditors? I can’t make my first payment.

April 17, 2023

A: A debtor may convert a chapter 13 case to a chapter 7 liquidation case, at any time. The right to convert to chapter 7 is unqualified and may not be waived. However, a case cannot be converted to a chapter for which a debtor is ineligible. Therefore, a debtor converting from chapter 13 to chapter 7 by right may still be subject to the means-test formula if his or her current monthly income at the time of filing the chapter 13 exceeded he applicable state median income. For a debtor that legitimately is unable to carry out a confirmable chapter 13 plan, this hurdle should not be insurmountable. If after applying the means test a presumption of abuse arises, the debtor may rebut the presumption by showing special circumstances. Once a debtor files a notice of conversion, the conversion is automatic and immediate; it cannot be delayed by the court.

Q. How can I qualify for the 475 election as a day trader? Thanks

April 11, 2023

A: First, you must determine whether you can qualify as a trader for federal tax purposes. This determination is based on pertinent facts and circumstances. Special rules apply if you're a trader in securities, in the business of buying and selling securities for your own account. The law considers this to be a business, even though a trader doesn't maintain an inventory and doesn't have customers. To be engaged in business as a trader in securities, you must meet all of the following conditions: • You must seek to profit from daily market movements in the prices of securities and not from dividends, interest, or capital appreciation; • Your activity must be substantial; and • You must carry on the activity with continuity and regularity. The following facts and circumstances should be considered in determining if your activity is a securities trading business: • Typical holding periods for securities bought and sold; • The frequency and dollar amount of your trades during the year; • The extent to which you pursue the activity to produce income for a livelihood; and • The amount of time you devote to the activity. If the nature of your trading activities doesn't qualify as a business, you're considered an investor and not a trader. It doesn't matter whether you call yourself a trader or a day trader, you're an investor. A taxpayer may be a trader in some securities and may hold other securities for investment. The special rules for traders don't apply to those securities held for investment. A trader must keep detailed records to distinguish the securities held for investment from the securities in the trading business. The securities held for investment must be identified as such in the trader's records on the day he or she acquires them (for example, by holding them in a separate brokerage account). Traders can choose to use the mark-to-market rules, investors can't. If a trader doesn't make a valid mark-to-market election under section 475(f), then he or she must treat the gains and losses from sales of securities as capital gains and losses and report the sales on Schedule D (Form 1040), Capital Gains and Losses and on Form 8949, Sales and Other Dispositions of Capital Assets as appropriate. When reporting on Schedule D, both the limitations on capital losses and the wash sales rules continue to apply. However, if a trader makes a timely mark-to-market election, then he or she can treat the gains and losses from sales of securities as ordinary gains and losses (except for securities held for investment - see above) that must be reported on Part II of Form 4797, Sales of Business Property. Neither the limitations on capital losses nor the wash sale rules apply to traders using the mark-to-market method of accounting. A trader must make the mark-to-market election by the original due date (not including extensions) of the tax return for the year prior to the year for which the election becomes effective. You can make the election by attaching a statement either to your income tax return if filed without an extension or to a request for an extension of time to file your return. The statement should include the following information: 1) That you're making an election under section 475(f); 2) The first tax year for which the election is effective (that is, the tax year for which a timely election is being made); and 3) The trade or business for which you're making the election.