Individual Strategies

“I’m going to get a pedicure later,” my wife said to me one Saturday morning. I quickly replied, “You should start an OnlyFans so you can deduct it.” (Everything has a tax angle when you’re married to a tax person.) “Is that really a thing?” she inquired. “Well…” I said, “It depends...” (Nothing is certain when you’re married to a tax person.) “...ordinarily I would say no, but in this case, it might be necessary.” (Everything is a tax pun when you’re married to a tax person.) In the “post” covid era, many taxpayers have turned to the gig economy. (Aside from the number of companies paying workers as contractors when they should actually be employees, but that’s a different topic for a different time.) Many of these gig workers are new to being self- employed and wonder what exactly they can “write off.”

"I knew he was a crook when I married him." Come again? And you still married him? That's what I said in my head as it took every muscle in my face to keep my forehead from scowling. But instead, I said, "What do you mean?" "We always had good money and nice things, but we never paid taxes. I always owed when I was single. But when we got married, I stopped working and we never owed." Let me take a moment to rewind and get you up to speed. This taxpayer, let's call her Mrs. Bonnie for the purposes of this story, reached out because she needed to file last year's tax return. She was recently widowed, and her husband typically handled the tax filing. So, she was already feeling overwhelmed and lost when it happened. She went to the mailbox and pulled out mail from the IRS. It was a CP3219A , notifying her that credits claimed on a previous tax return were being disallowed by the IRS. Not only did she owe taxes, but she also owed accuracy related penalties. She only had 90 days to respond if she disagreed and didn't know what to do. When she reached out to me, she inquired about whether I could review previous year returns. Mrs. Bonnie wanted to make sure that they were "done right". This isn't a strange request. I told her that I would review the prior year to have a baseline and if I saw anything fishy, I'd bring it to her attention and perhaps look at another year. I didn't even make it to the signatures before the fishiness leaped off the page. I set up a meeting with her via Zoom to review my findings. As I begin to ask about some of the credits claimed and her husband's business her answers did not match what was on the return. That's when she let me know that she knew her husband, Mr. Clyde, was a crook when she married him. Mrs. Bonnie didn't know much about taxes, but she did a bit of research. She read about something called Innocent Spouse Relief and thought she may be eligible. Let's look at what Innocent Spouse Relief is and why Mrs. Bonnie was not eligible, but your client may be.

Here are a few reminders on claiming losses from property transactions with a focus on an informal ruling the IRS issued in January 2023 to help explain losses from certain cryptocurrency transactions. This article focuses not only on what CCA 202302011 provides, but also what it doesn’t cover regarding possible losses from cryptocurrency and digital asset transactions. Click here to continue reading…

Beanie babies, Pokémon cards, POGs, and digital pictures of monkeys on the internet, one of these things is not like the others. All these are items that people may collect or at least have collected in the past. Maybe they were just collecting for fun, or perhaps they acquired in hopes of selling their items in the future for a profit. However, the IRS has highlighted only one of the items on this list as potentially being a collectible. A non-fungible token (NFT) “is a unique digital identifier that is recorded using distributed ledger technology and may be used to certify authenticity and ownership of an associated right or asset. Ownership of an NFT may provide the holder a right with respect to a digital file (such as a digital image).” NFTs run the gamut from bored apes (computer generated pictures of monkeys that sell for hundreds of thousands of dollars, not to be confused with board apes, which are monkey pictures on sandwich and surf boards and do not sell for hundreds of thousands of dollars) to Ruish Bronzelight (a DeFi Kingdoms online video game Warrior Wizard we met in “Tax Planning for DeFi Based Games”), and even event tickets (especially popular with crypto conferences). There is even at least one CPA who sells access to his tax practice via NFT. Click here to continue reading…

Every tax professional has at least one client that when asked about business mileage replies, “I don’t know; what did I have last year?” You may have read that last sentence and thought, “most of them.” Self-employed taxpayers generally know they must track their mileage, but it’s seldom done correctly, or at all. Vehicle deductions are an area frequently challenged by the IRS on examination as well as an area the taxpayer is unlikely to prevail without strong, contemporaneous documentation. That said, very few taxpayers keep perfect records, so what are the best practices for mileage deductions in the real world? Keep reading to find out!

“Timalyn, Alyssa and I filed for divorce, and we will finalize everything before Thanksgiving. Does this change things for our taxes?” “No! Can we wait until January 1?” were my initial thoughts. But then I realized that if this news blindsided me, the seemingly happy couple was probably also scrambling for answers. They were looking to me to be calm during an upcoming storm. To give you some context, I had helped this family lower their back taxes by $16,000 and get a payment plan that worked well with their cash flow. Then, by implementing a few strategies they had just saved an extra $20,000 on their last tax return. We were planning on saving them even more money in upcoming years. Then, that is when it happened. Divorce. I never saw this happening, so I never prepared for it. But if it happened to me, it will happen to you. Clients divorce. Some of the things we are going over today may seem obvious to you. But remember what is obvious to us as tax experts is not obvious to our clients, especially if they are going through a life-changing event such as divorce. Here are four things you need to inform your client about when it comes to their divorce and taxes...

Reilly’s Fourth Law of Tax: “Execution isn’t everything, but it’s a lot” might be amended when it comes to charitable deduction of property, because there you have an area where execution is almost everything. It is also an area that dramatically illustrates the Seventh Law: “Read the instructions.” In January, we received guidance from the IRS on the reporting requirements for charitable contributions of crypto currency . If you have followed IRS guidance on crypto and know something about charitable donation reporting requirements, the result shouldn’t surprise you , but maybe it will. The most disturbing part of the story is that the IRS may be asking for something we can’t provide...

Question: A spouse didn’t meet the residence test when the home sold because they weren’t legally married for two years on the date of the house sale. You indicated, however, the spouse is eligible for the home exclusion because by the end of the year they were married for two years Answer: If you want to understand how getting married impacts your ability to take tax-free profit, we must look at two issues and pass two tests. To take the full 121 exclusion deduction amount ($250,000/$500,000), first you have to determine filing status. If you were married or an RDP as of December 31, 2022, even if you did not live with your spouse/RDP at the end of 2022, your filing status is either Married Filing Joint or Married Filing Separate. Either way, the IRS considers you married for tax purposes. Now that you’ve determined that the client’s filing status is married, the potential gain exclusion is $500,000 under Section 121. But there are two important tests to apply to see whether you can exclude the maximum of $500,000 or whether it is going to be less. To learn about these tests, read on.