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Have you considered declaring bankruptcy? I know it sounds extreme, but if your debt is really that bad, it might be better than draining your retirement. Credit card debt can be discharged in bankruptcy, but you get to keep your retirement accounts (with some limits). Your credit will take a hit for several years, but you might come out ahead financially compared to losing a huge chunk of your retirement to taxes and penalties.
I've thought about bankruptcy, but I'm worried about how it would affect my new business. Since I'm just getting started, I need to be able to get business credit, possibly lease equipment, etc. From what I understand, bankruptcy would make that nearly impossible for several years, right? Also, there's some personal pride involved - I want to pay what I owe if possible.
Bankruptcy might actually be less harmful to your new business than you think. Chapter 13 allows you to reorganize your debts rather than liquidate, which could protect your ability to operate. Many entrepreneurs have successfully started businesses after bankruptcy - it's not the death sentence it used to be. As for business credit, you'd likely need to rely on business revenue rather than credit for a while, but there are specialized lenders who work with post-bankruptcy entrepreneurs. The pride aspect is understandable, but from a pure financial perspective, protecting your retirement might be the wiser long-term choice.
Has anyone tried using one of those debt settlement companies? I see ads for them all the time promising to cut credit card debt by 50% or more. Would that be better than touching the 401k?
Those debt settlement companies can be REALLY sketchy. They typically tell you to stop paying your credit cards entirely while they "negotiate" with your creditors. Meanwhile, your credit score tanks, you rack up late fees, and often get sued by the credit card companies. They also charge hefty fees - usually 15-25% of your enrolled debt. I work in financial counseling and have seen more people get burned by those companies than helped. If you want legitimate help with debt, look into nonprofit credit counseling agencies instead - they offer Debt Management Plans that can lower interest rates without the risks of debt settlement.
You need to file Form 3115 to change accounting methods if you want to switch from standard mileage to actual expenses. I learned this the hard way and got hit with penalties. Make sure your accountant knows what they're doing!
But doesn't the business vs personal use percentage still apply even if you use standard mileage rate? Like if the car was 70% business and 30% personal, wouldn't that affect how the gain/loss is calculated when selling?
Yes, the business/personal percentage absolutely still applies. With standard mileage, you're only claiming deductions on the business portion anyway (your business miles). When you sell the car, you need to allocate any gain or loss based on that same business use percentage. So in your example with 70% business use, only 70% of any gain or loss would be business-related. But remember, the standard mileage deduction you've taken over time has already reduced your basis for the business portion of the car, which is why many people end up with a gain instead of a loss when they sell, even if they sell for less than they paid.
Just went through this last year. I sold my delivery car for $5,000 after buying it for $17,000 four years earlier. My tax guy initially tried to claim an $8,000 loss on my Schedule C but then realized I'd already claimed about $13,000 in depreciation through the standard mileage rate over the years. Ended up having to report a $1,000 GAIN instead. So annoying.
One thing that hasn't been mentioned is a potential restructuring of your agreement with your business partner. If you're consistently taking distributions beyond your 5% ownership, maybe your ownership percentage doesn't actually reflect your value to the company. Consider renegotiating your equity stake to better align with the economic reality of the business. This would solve the distribution problem long-term because your K-1 would better reflect what you're actually taking from the business. Another approach is to look at compensation strategies beyond just salary and distributions. Could part of your compensation be structured as guaranteed payments? Unlike distributions, these ARE deductible by the S-Corp before profits are allocated via K-1s.
The idea of renegotiating my equity stake is interesting. My partner and I have been operating this way for years without really thinking about the tax consequences. Do guaranteed payments still incur self-employment tax like salary would?
Yes, guaranteed payments do incur self-employment tax similar to salary. That's the downside compared to distributions. However, unlike regular salary which needs to meet "reasonable compensation" standards, guaranteed payments can be tied to specific services or capital you provide to the business. They're especially useful when partners contribute unequally in ways not reflected by ownership percentages. For the equity restructuring, you might consider a gradual approach where your percentage increases over time based on predefined performance metrics. This could help align your tax situation with the economic reality without creating a sudden shift in the business relationship.
Has anyone here actually tried using a loan structure instead of distributions? Our S-Corp (I'm a 30% owner) established a shareholder loan program where we can take advances beyond our distribution percentages, and then either repay them or have them forgiven as future distributions when our basis is sufficient. Seems cleaner than just taking distributions beyond ownership percentage, but I'm not sure if there are downsides.
Have you considered structuring the purchase differently? Maybe instead of buying the book of business outright, you could set up an arrangement where you pay the retiring agent a percentage of the business you actually retain each year? This would essentially give you a current deduction for what you pay rather than having to amortize it. I did something similar when buying a small law practice. We structured it as a 5-year earn-out based on client retention, which allowed me to deduct the payments as they were made instead of dealing with the 15-year amortization. Worked out much better for cash flow.
That's an interesting approach. Did you have any issues with the IRS viewing it as a disguised purchase of goodwill? Did you need to structure it in a specific way to make sure it worked?
We were careful to structure it as true contingent payments based on future performance, not just an installment sale. The payments were directly tied to retained clients and their actual revenue each year, with no minimum guarantees. My tax attorney said the key is making sure it's genuinely contingent on future performance and not just spreading payments for a fixed asset. We documented everything thoroughly to show the payments were earned as the benefit was realized. It's been 4 years and we've had no issues with the IRS.
One option nobody's mentioned - consider allocating some of the purchase price to a consulting agreement with the retiring agent. If they're willing to be available for occasional client questions or transition issues, you can pay them a consulting fee over a shorter period (like 3-5 years) which would be fully deductible as a business expense. We did this when buying a dental practice. Instead of putting the entire purchase toward goodwill, about 25% went to a consulting agreement. It was legitimate since the retiring dentist did provide occasional consultation on complex patient cases, but it also gave us more immediate tax deductions.
CosmicCaptain
Another option nobody mentioned is pulling your credit report. I've had situations where income was misreported under my SSN, and reviewing all accounts on my credit report helped me identify where the error might have come from. Sometimes it's a company you forgot about or an account that was opened fraudulently.
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Yuki Tanaka
ā¢Would a credit report really show income though? I thought it just showed credit accounts and payment history, not actual income reporting. Did you find specific income information there?
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CosmicCaptain
ā¢You're right that the credit report itself doesn't show income directly. What I meant was that reviewing your credit report can remind you of accounts you may have forgotten about (old bank accounts, investments, etc.) that might have generated income. For example, in my case, I saw an old investment account on my credit report that I had forgotten about, which led me to contact that company, and sure enough, they had issued a 1099 for a small amount of dividend income. The credit report was just a starting point to jog my memory about possible income sources I might have overlooked.
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Giovanni Rossi
If you filed with tax software like TurboTax or H&R Block, sometimes they offer audit support or tax notice assistance. Check if your filing package included this - they might help you figure out the discrepancy without additional cost.
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Fatima Al-Maktoum
ā¢This! I used TurboTax last year and they had a "MAX" package that included audit support. When I got a similar notice, their tax pros helped identify the issue and even handled some of the communication with the IRS. Definitely worth checking if you already paid for this with your filing.
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