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I met with a young business owner this week - one of his questions is the most common ones I get asked all the time. "I took out $150,000 from my business, so I'm going to have to pay tax on that right?" The answer in his case was, "you already have." He stared blankly back at me and we ran through this concept π When a Distribution is TaxableIf you own a "pass-through" business (you get a K1, or are a sole proprietor) then you get taxed income of the business whether you take out a distribution or not. In his case, he'd already paid tax on that income in 2025 so there was no tax due on distributing "already taxed" money. But not every distribution is like this. Here are a few types of distributions that could trigger tax:
You already know - let's dig into each one in plain English. π Preferred Returns as Guaranteed PaymentsThese usually happen in "different classes of equity" - very popular in real estate. Investors are promised a preferred return on their capital invested - call it 8% - and then after that 8% is achieved, the sponsor (GP) receives rights to larger distributions (called a promote). The part that many tax pros miss is the tax treatment of that preferred return. If the operating agreement indicates it is accrued and payable regardless of entity income or profits, then that's treated more like an interest payment to them (like they're a bank). Those payments then go on a different line on the K1 (Box 4) and are taxable to that partner. Distributions in Excess of BasisThis is where "type of entity" really matters. βοΈ Partnerships are great for distributions that are financed with debt. S-Corps are terrible for this kind of distribution. Partnerships give investors and owners "debt basis" - so even if your "capital" is negative, if you have liability allocated to your K1, you don't pay tax on that distribution. (This gets tricky quickly, so be wary of the nuance) S-Corps definitely don't work like that, if you take out a distribution and have no "capital" or "equity" - meaning all or a part of that distribution was financed with that debt - then that distribution is taxable. Disguised SalesSaved the best for last. π₯Έ Years ago, there was a popular tax court case for the sale of the Cubs. The seller worked with the buyer to try to shield some of the sales price via a leveraged partnership distribution. The surprising part of the case wasn't that some of the payout was taxable - it was that a substantial part of it was held as not taxable (deferred). Disguised sales happen when property is contributed to a partnership with another investor and then soon after a distribution is taken by the partner that contributed property (2 years). The Cubs sale took advantage of a caveat to that rule - when the distribution is from legitimate debt. But I see this happen many times for people sitting on old valuable land - thinking they can just drop into a JV and take cash out immediately. It does not work like that. The TakeawayIf you're still staring blankly at the screen - know that we can help. Because whether you owe tax on the distribution you just took or received can be nerve-wracking. Happy 4th of July πΊπΈ π¦ π½ π«‘ New episode of Today in Tax Court just dropped this week - going into the history of HOW we got the income tax. From Articles of Confederation to Civil War to Constitutional Amendment. If you like history, it's a great look back at our country's history and where it all went wrong π€£
Group Chat Worthy Posts π₯π²
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I've been a CPA for nearly 20 years - serving private small business and real estate the entire time. I take the lessons learned in serving and now running a small business and share them here. For business owners, investors, and advisors looking to lower their cost of capital, subscribe for delivery straight to your inbox π Also on YouTube at PlugAccountingandTax!
The best attorneys are specialists - ideally at keeping you out of trouble. This specialization mostly comes in the form of transaction structuring, risk identification, or legal procedures. A few of them have taken a wrong turn and wound up as tax attorneys. But of those few, even fewer have ever filed a tax return or allocated income and loss on K1s. Which is a shame because that's an experience that is sorely needed when drawing up operating agreements. I've been reviewing operating...
3 years. Now on to the memes. π Only kidding. Obviously there's a lot of nuance to this question I get several times a year (albeit less often with the real estate market being where it is now). Let's look at the factors that impact to Cost Seg or not to Cost Seg: Covering the Obvious - Recapture The primary argument against cost segregation studies is "depreciation recapture." π± Most of my readers are likely real estate literate and understand the concept, but just quickly for those...
Most buyers treat accounting as the cost of keeping score. You close on a business or a property, you hand the books to a bookkeeper, and you check back at tax time. The accounting department becomes a compliance expense. A necessary evil. Overhead. That framing costs you real money. Done right, the accounting function in a newly acquired business or property is one of the highest-ROI investments you'll make in the first year of ownership. It finds revenue you're entitled to but never billed....