Tax Issues for Those Who Counsel Businesses


CLE Credits earned: 4 GENERAL (or 4 LAW & LEGAL for WA state)

This program is designed for attorneys who counsel businesses in helping them identify and work through tax issues. In my experience, there is a deficiency in the knowledge base of many who have business clients or who serve as general counsel. This is designed to be a broad overview of the tax issues that face many businesses in order to serve a guidepost for attorneys to provide better advice in the future or to know when to involve a tax attorney or another tax professional in a situation.

Key topics to be discussed:

•   How to use tax compliance to maximize profit within an organization
•   How to handle an IRS collections issue for businesses and how to protect the owners
•   How to handle a sales tax audit
•   How to handle a payroll tax audit

Date / Time: January 11, 2019

•   1:00 pm – 5:15 pm Eastern
•   12:00 pm – 4:15 pm Central
•   11:00 am – 3:15 pm Mountain
•   10:00 am – 2:15 pm Pacific

Choose a format:

•   Live Video Broadcast/Re-Broadcast: Watch Program “live” in real-time, must sign-in and watch program on date and time set above. May ask questions during presentation via chat box. Qualifies for “live” CLE credit.
•   On-Demand Video: Access CLE 24/7 via on-demand library and watch program anytime. Qualifies for self-study CLE credit. On-demand versions are made available 7 business days after the original recording date and are view-able for up to one year.

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Original Broadcast Date: January 11, 2019

Samuel D. Brotman, Esq. is a practicing attorney in San Diego and the founder of Brotman Law. His practice primarily centers on all aspects of tax litigation and criminal/civil tax controversies in front of the Internal Revenue Service, Franchise Tax Board, Employment Development Department, Board of Equalization, and various other state/local tax agencies. Although a strong proponent of early stage tax resolution, Sam’s practice is uniquely tailored to assist clients in all phases of their tax controversy from administrative resolution to suits in superior/district court. In addition, Sam frequently handles corporate/real estate/litigation matters related to small and mid-size businesses.

Prior to founding Brotman Law, Sam chaired the corporate law and corporate tax departments for a prominent boutique tax firm in San Diego while representing a variety of business owners, high net worth individuals, and regional conglomerates. Sam has assisted hundreds of clients in resolving their tax disputes and has amassed an excellent reputation along with a decorated record of success. As lead counsel, he prevented numerous businesses from being shut down by government agencies, saved his clients millions in taxes, and protected the livelihoods of several individuals and their families. In addition, he has defended clients against charges by the US Department of Justice and California Department of Justice and, in some cases, has negotiated resolutions to avoid prosecution entirely.

Sam also has an extensive corporate law background and track record of success in corporate matters. He served as lead counsel on several major transactions, navigated his clients through several multi-million dollar commercial debt workouts, and oversaw day-to-day legal operations for two large Southern California corporations. Sam has a broad business background in a variety of areas, including as an owner, and excels at breaking down legal decisions into a business framework. In addition to providing legal advice, Sam provides business operational advice and strategy to several established companies, startups, and sole-proprietorships. He is consulted frequently for advice for businesses looking to increase their revenue and those seeking stronger financial control systems. Prior to his licensure, Sam was formerly with Covington & Burling LLP in New York City. As a senior legal assistant there, he was a key representative on over twenty major corporate transactions and was assistant to special counsel for two of the largest bankruptcies in United States history.

Sam received his Juris Doctorate and his Masters of Laws in Taxation (LL.M.) from the University of San Diego. While in law school, he was professionally certified as a mediator and won numerous awards for oral and written advocacy. He was also a past president of the USD Vis Moot International Arbitrations team and led his team to the most accolades in school history. Sam also graduated with his Masters in Business Administration from San Diego State University with an emphasis in corporate finance and entrepreneurship. As part of his capstone work, Sam made recommendations implemented by the City of San Diego’s Economic Development Department and was commended by the city and the university for exemplary work in helping to create jobs and grow the city’s economy.

Prior to law school, he completed his undergraduate education at Wabash College (cum laude) with a dual B.A. in English and Religion. Additionally, he received “highest honors” standing from St. Catherine’s College at Oxford University in 2004. In 1999, Sam was one of twenty-six individuals selected by the American Field Service for a year-long course of study in Japan.

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I. Setting Yourself Up for Success

II. Understanding Tax Policy – Why the system works the way it does

III. Understanding the Tax Gap and How the IRS Works

IV. Your Tax and Financial “A” Team – Bookkeeper, CPA, Tax Attorney, CFO

VI. Planning

VII. The Goals of Proper Tax Planning

VIII. Structuring Your Business for the Greatest Tax Benefit

IX. Tax Tips

X. Think about your lifestyle as a business owner, plan accordingly

XI. Accelerate or Defer Cash Salaries, Bonuses, or Compensation

XII. Accelerate or Defer Charitable Contributions, Mortgage Interest, Investment Interest, Business Expenses

XIII. Business Owners – Timing of Income and Deductions

XIV. Business Equipment Purchases – Credit Card Purchases for Cash Basis Taxpayers are allowed expenses

XV. Don’t Forget to Expense Business Interest Expense

XVI. Avoiding the Penalty for Estimated Taxes

XVII. Understand How AMT Impacts You – Eisner Amper, 26 and 29

XVIII. Start Up Expenses and Organizational Costs –5k immediate deduction each, rest gets amortized over 180 months

XIX. Self-Employed Health Insurance Deduction

XX. Special considerations for S-Corporations

XXI. Qualified Small Business Stock Sales

XXII. Passive Losses – Convert Passive Losses into Active Losses (no limitation) or increase passive income activities

XXIII. Using installment sales

XXIV. Understanding the distinction between compensation for services and profit

XXV. Moving money between the corporate entity and ownership

XXVI. Non-income transactions between ownership and the corporate entity

XXVII. Protection

XXVIII. What happens when you file your tax return

XXIX. Income Tax Audits

XXX. The Audit Process and How to Handle an Audit

XXXI. IRS Collections

XXXII. What if I Can’t Pay in Full?

XXXIII. How the IRS conducts financial analysis

XXXIV. How to handle an IRS Collection Case for a business

XXXV. How to handle an IRS Collection Case for a high net worth individual

XXXVI. Payroll Taxes Collections

XXXVII. Payroll Tax Audits

XXXVIII. Sales Tax Audits

XXXIX. Sales Tax Collections

XL. Issues for Multi-state businesses