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Matthew J. Sherman

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Tax Bankruptcy and Tax Controversy Attorney
  • Tax Law, Bankruptcy
  • Florida
Review This Lawyer
Lawyer Rating and Reviews
Legal Knowledge
5.0/5.0
Legal Analysis
5.0/5.0
Communication Skills
5.0/5.0
Ethics and Professionalism
5.0/5.0
Spencer Strom
Spencer Strom April 3, 2023
Rating: 10 Lawyer Rating - 10 out of 10
Matthew was the hardest working classmate I had in law school and continues to have the same qualities in his legal career.
Client Reviews
J. M. April 18, 2023
Complex Tax Help Matthew and team provided stellar help with a complex tax case. Matt took the time to understand my needs and swiftly came up with a plan of action. He is an expert in legal matters related to tax and I will recommend him. Thanks for all your help this past couple of weeks.
Jonathan O. March 20, 2023
Professional and Responsive Tax Attorney Mr. Sherman is an excellent tax advisor who was there every step of the way. He was very professional and responsive. I would highly recommend him for any / all tax needs. I am very grateful for his diligence and attentiveness in the matters that he handled for me as he made the process a lot easier and less stressful than I expected.
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Biography

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.

Practice Areas
    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
Additional Practice Areas
  • Tax Bankruptcy - focused on the discharge of tax claims in bankruptcy.
  • Tax Controversy - focused on the resolution of tax claims.
Video Conferencing
  • Skype
  • Zoom
  • GoToMeeting
  • Microsoft Teams
  • RingCentral
  • WhatsApp
Fees
  • Free Consultation
Jurisdictions Admitted to Practice
Florida
The Florida Bar
ID Number: 1038794
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U.S. District Court, Middle District of Florida
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U.S. District Court, Northern District of Florida
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U.S. District Court, Southern District of Florida
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U.S. Tax Court
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Languages
  • English
  • Spanish
Professional Experience
Attorney
Tax Workout Group, P.A.
Current
Practice Group Leader - Tax Bankruptcy and Tax Controversy.
Accountant
Better Life Products Investment Group, Inc.
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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.
Education
University of Florida
B.S. | Accounting
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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
Nova Southeastern University Logo
University of Florida Levin College of Law
LL.M. | Taxation
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Awards
CALI Excellence for the Future Award, Income Tax
Shepard Broad Law Center, Nova Southeastern University
Professional Associations
The Florida Bar  # 1038794
Attorney
Current
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Certifications
Certified Public Accountant
Florida Board of Accountancy
Websites & Blogs
Website
Blog
Tax Workout Group Blog
Legal Answers
5 Questions Answered
Q. When hiring a CPA , who is responsibile for knowing the law?
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.
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
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.
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Contact & Map
Tax Workout Group
Boca Raton Office
150 East Palmetto Park Road, Suite 800
Boca Raton, FL 33432
Toll-Free: (866) 282-9333
Telephone: (561) 571-2004
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
Tax Workout Group
Miami Office
2915 Biscayne Boulevard
Suite 300
Miami, FL 33137
Toll-Free: (866) 282-9333
Telephone: (305) 203-1563
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
Tax Workout Group
Jacksonville Office
50 N. Laura Street
Suite 2500
Jacksonville, FL 32202
Toll-Free: (866) 282-9333
Telephone: (904) 544-3778
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
Tax Workout Group
Tallahassee Office
113 South Monroe Street
First Floor
Tallahassee, FL 32301
Toll-Free: (866) 282-9333
Telephone: (850) 299-0962
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
Tax Workout Group
Tampa Office
100 S Ashley Drive
Suite 600
Tampa, FL 33602
Toll-Free: (866) 282-9333
Telephone: (813) 720-8320
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
Tax Workout Group
Orlando Office
121 S. Orange Avenue
Suite 1500
Orlando, FL 32801
Toll-Free: (866) 282-9333
Telephone: (321) 430-1045
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
Tax Workout Group
West Palm Beach Office
1645 Palm Beach Lakes
Suite 1200
West Palm Beach, FL 33401
Telephone: (561) 861-0926
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
Tax Workout Group
Fort Lauderdale Office
1 East Broward Boulevard,
Suite 700
Fort Lauderdale, FL 33301
Toll-Free: (866) 282-9333
Telephone: (954) 355-7137
Fax: (866) 511-2384
Monday: 8 AM - 8 PM
Tuesday: 8 AM - 8 PM (Today)
Wednesday: 8 AM - 8 PM
Thursday: 8 AM - 8 PM
Friday: 8 AM - 8 PM
Saturday: 10 AM - 6 PM
Sunday: Closed
Notice: We operate virtually to the greatest extent possible and as a result, offer access to a wide range of prominent tax and bankruptcy attorneys with the experience, relationships, expertise, and collective resources to deliver high-level client satisfaction.
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