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The Plug [Newsletter]

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 👇 Also on YouTube at PlugAccountingandTax!

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Can You Put that Income in a S-Corp?

Two hockey players for the Minnesota North Stars ran their NHL contracts through their own corporations and beat the IRS in the 1980s. A financial advisor did the same thing in the 2010s with his commissions and got assessed $41,563 in self-employment tax. Same structure, same idea, opposite outcomes. The difference had nothing to do with the entity type, the election, or the bookkeeping. It came down to whose name was on the contract with the people writing the checks. This is a terrifying...

There is no lack of bad advice from tax gurus with (a) no real experience, and (b) no real skin in the game. And one of their favorite "loopholes" is paying your kids to save thousands in taxes. Which sucks because it's given this strategy a stigma where a lot of taxpayers write it off as tax fraud without understanding how it can be done legitimately. Today we'll do just that. Here's the real way to pay your kids, how much tax it saves, and what to avoid. The exemption lives in the entity,...

Psych - that's crazy talk. I'm a CPA and went to a lake house with my family. No way I'm going to deduct any of that. But what are the rules here? How do people actually do this? Let's jam 👇 It comes down to a day count The IRS settles this with one question. Was the trip primarily business or primarily personal? Domestic travel is all or nothing on the flight. Primarily business, and the entire airfare is deductible even though you spent Saturday on a boat. Primarily personal, and the...

Years ago, one of the largest owners of real estate in Houston came to our firm with a new-fangled tax structure they were about a week away from executing. Looked great on paper and hit their pain points. But in reality it would have handed the IRS a gift tax bill in the millions, and nobody in the room had any idea. Here is what they were trying to do - something not uncommon: The parents were in their sixties. They owned all this commercial real estate, and for historical reasons it sat...

It's that time of the quarter: the check-in on whether your operating agreement will survive tax scrutiny. Today I want to show you the section I check first on every agreement. 👉 Liquidating Distributions 👈 What this section does When the partnership sells and winds down, this section decides who gets the money. Most read the same way: creditors first, then partner loans, then the partners. The middle can get nuanced. The ending can't. The final split has to match the real economics of the...

Calls with prospective clients often turn into "show me what you got" contests. But tax strategy doesn't work like that... It's a multi-phase process of decision making. Before we name a single strategy, we have to answer three questions about you. The answers decide which moves are on the table and which are noise. And this process compounds with time - as we learn your tendencies, goals, and risk appetite. And with our selling season picking up steam, I wanted to share how we think about...

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 👇 When a Distribution is Taxable If 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...

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. 👇 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." 😱 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....