Federal Income Tax – Page 2 – DougFreemanCPA.com

A refresher on the trust fund recovery penalty for business owners and executives

One might assume the term “trust fund recovery penalty” has something to do with estate planning. It’s important for business owners and executives to know better. In point of fact, the trust fund recovery penalty relates to payroll taxes. The IRS uses it to hold accountable “responsible persons” who willfully withhold income and payroll taxes […]

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What types of expenses can’t be written off by your business?

Business Deductions, Federal Income Tax, Federal Tax Deductions, Internal Revenue Service (IRS), Small Business Tax Tips, Small Business Tips, Tax Deduction / Douglas Freeman

If you read the Internal Revenue Code (and you probably don’t want to!), you may be surprised to find that most business deductions aren’t specifically listed. For example, the tax law doesn’t explicitly state that you can deduct office supplies and certain other expenses. Some expenses are detailed in the tax code, but the general

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What are the tax implications of winning money or valuable prizes?

Federal Income Tax, Federal Tax Deductions, Gambling Taxation, Itemized Deduction, Tax Record Retention / Debbie Davis

If you gamble or buy lottery tickets and you’re lucky enough to win, congratulations! After you celebrate, be aware that there are tax consequences attached to your good fortune. Winning at gambling. For tax purposes, it doesn’t matter if you win at the casino, a bingo hall or elsewhere. You must report 100% of your

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It’s important to understand how taxes factor into M&A transactions

Assets, C Corporation, Federal Income Tax, LLC, Merger & Acquisition, Partnerships, Past-Through Entities, S Corporation, Small Business, Small Business Owners, Small Business Stock, Small Business Tax Tips, Stocks, Tax Considerations for Selling Your Business / Douglas Freeman

In recent years, merger and acquisition activity has been strong in many industries. If your business is considering merging with or acquiring another business, it’s important to understand how the transaction will be taxed under current law. Stocks vs. assets. From a tax standpoint, a transaction can basically be structured in two ways: 1. Stock

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Spouse-run businesses face special tax issues

Federal Income Tax, Partnerships, Self Employment Tax, Social Security & Medicare (FICA) taxes / Douglas Freeman

Do you and your spouse together operate a profitable unincorporated small business? If so, you face some challenging tax issues. The partnership issue. An unincorporated business with your spouse is classified as a partnership for federal income tax purposes unless you can avoid that treatment. Otherwise, you must file an annual partnership return, on Form

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The advantages of using an LLC for your small business

Federal Income Tax, Limited Liability Company, LLC, Partnerships, S Corporation, Shareholder, Small Business, Small Business Tax Tips / Douglas Freeman

If you operate your small business as a sole proprietorship, you may have thought about forming a limited liability company (LLC) to protect your assets. Or maybe you’re launching a new business and want to know your options for setting it up. Here are the basics of operating as an LLC and why it might

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A tax-smart way to develop and sell appreciated land

(NIIT) Net Investment Income Tax, Captial Gains, Federal Income Tax, Land Owners, Ordinary Income Tax, Real Estate, S Corporation / Douglas Freeman

Let’s say you own highly appreciated land that’s now ripe for development. If you subdivide it, develop the resulting parcels and sell them off for a hefty profit, it could trigger a large tax bill. In this scenario, the tax rules generally treat you as a real estate dealer. That means your entire profit —

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Benefits of a living trust for your estate

Assets, Estate Planning, Federal Estate Tax, Federal Income Tax, Living Trust / Douglas Freeman

You may think you don’t need to make any estate planning moves because of the generous federal estate tax exemption of $12.92 million for 2023 (effectively $25.84 million if you’re married). However, if you have significant assets, you should consider establishing a living trust to avoid probate. Probate is a court-supervised legal process intended to

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The IRS clarifies what counts as qualified medical expenses

AGI (Adjustable Gross Income), Federal Income Tax, FSA, HSA, Itemized Deduction, Medical Deductions, Medical Expenses, Qualified Medical Expenses / Douglas Freeman

If you itemize deductions on your tax return, you may wonder: What medical expenses can I include? The IRS recently issued some frequently asked questions addressing when certain costs are qualified medical expenses for federal income tax purposes. Basic rules and IRS clarifications. You can claim an itemized deduction for qualified medical expenses that exceed

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The tax advantages of hiring your child this summer

Business Income Tax, Federal Income Tax, Federal Income Tax Filing, Federal Unemployment (FUTA Tax, Income Tax, Small Business Tax Tips, Social Security & Medicare (FICA) taxes, Summer Employees / Douglas Freeman

Summer is around the corner so you may be thinking about hiring young people at your small business. At the same time, you may have children looking to earn extra spending money. You can save family income and payroll taxes by putting your child on the payroll. It’s a win-win! Here are four tax advantages.

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