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For someone in your situation with $475K from a business sale, I'd strongly recommend "The Tax and Legal Playbook" by Mark Kohler. He's both a CPA and attorney, so he covers both the tax optimization and asset protection angles really well. The book specifically addresses how to structure things after a liquidity event like yours. Another excellent resource is "Loopholes of Real Estate" by Garrett Sutton - even if you're not planning to invest in real estate, it explains how different entity structures work for asset protection in ways that apply to any type of wealth. One thing I learned the hard way: don't rush into setting up complex structures just because you can. Start with understanding what you're actually trying to protect against and what your ongoing tax situation will look like. Sometimes a simple LLC is perfect, other times you might need a more sophisticated setup with trusts or multiple entities. Also, make sure whatever accountant you work with has experience with business sales and the resulting tax implications. The person who did your personal returns might not be the best fit for post-sale planning.
This is exactly the kind of practical advice I was hoping for! I hadn't considered that my regular accountant might not be the best fit for this level of planning. The Kohler book sounds perfect since it addresses both the tax and legal sides - that's exactly what I'm trying to wrap my head around. Quick question: when you mention not rushing into complex structures, how do you know when you actually need something more sophisticated than a basic LLC? Is it based on the amount of assets, the type of risks you're facing, or something else? I'm definitely guilty of getting excited about all the possibilities without really thinking through what problems I'm actually trying to solve. Thanks for the reality check!
Great question! The complexity you need really depends on three main factors: 1) Your risk exposure (are you in a lawsuit-prone profession or industry?), 2) The types of assets you have (real estate, securities, business interests each have different considerations), and 3) Your state's laws (some states like Nevada and Delaware offer better asset protection than others). For someone with $475K mostly in cash/securities, a single-member LLC might be perfect if you're just looking for basic liability protection and some tax flexibility. But if you're planning to buy rental properties, start another business, or you're in a high-risk profession, you might need multiple LLCs or even domestic asset protection trusts. The Kohler book actually has a great flowchart that helps you assess your specific situation. I'd start there before meeting with professionals - it'll help you ask the right questions and avoid getting sold structures you don't actually need. And you're absolutely right to think through the problems first! I see too many people set up elaborate structures and then realize they're paying thousands in annual maintenance fees for protection they didn't really need.
Coming from a similar situation (sold my tech consulting business last year), I can't recommend "The Entrepreneur's Guide to Business Law" by Bagley and Dauchy highly enough. It's more comprehensive than most single-topic books and covers everything from entity selection to exit strategies. For the asset protection side specifically, "Asset Protection for Everyone" by Robert Mintz is written in plain English and doesn't assume you have a law degree. He explains when simple structures work versus when you need more sophisticated planning. One practical tip: before diving deep into books, spend a weekend mapping out your current financial situation, future income expectations, and what specific risks you're trying to protect against. This will help you focus on the most relevant sections of whatever books you choose. Also, since you mentioned feeling lost with your accountant - consider interviewing 2-3 different CPAs who specialize in business owners and wealth management. The right professional relationship will be worth more than any book, and they can recommend additional reading tailored to your specific situation.
This is really solid advice! I especially like the idea of mapping out my situation before diving into the books - it would definitely help me focus on what's actually relevant rather than getting overwhelmed by all the different strategies out there. The point about interviewing multiple CPAs is something I hadn't really considered. I've just been working with the same guy who did my business taxes, but you're right that this is a completely different level of planning. Do you have any specific questions I should ask when interviewing potential CPAs to make sure they're experienced with post-sale planning? Also, how did you handle the timing of setting up your structures after your sale? I keep going back and forth on whether I should get everything in place quickly or take my time to really understand the options first.
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This thread has been incredibly helpful! I'm a newer tax preparer and just encountered this exact issue with a farming partnership that has both general and limited partners. The gross nonfarm income was flowing to all partners in my software and I couldn't figure out why. After reading through all the comments here, I checked the partner designation codes in Box I of each K-1 and found that was the issue - I had everyone coded as "GP" by default. Once I changed the limited partners to "LP", the software automatically stopped flowing the Box 14c amounts to them. One follow-up question though: our farming partnership also has some rental income from land they lease out to other farmers. Based on what Andre mentioned about rental income not being subject to SE tax, should that rental income also be excluded from Box 14c for the general partners, or does it depend on whether the rental activity is considered part of the farming business? Thanks to everyone who contributed to this discussion - saved me from filing incorrect returns!
Great question about the rental income! For farming partnerships, the treatment of rental income in Box 14c depends on whether the rental activity is considered part of the active farming business or a separate passive rental activity. If the partnership is actively engaged in farming operations and the land rental is incidental to the farming business (like renting out excess land while still farming the majority of their property), then the rental income might be considered part of the farming business and subject to SE tax for general partners. However, if the land rental is truly a separate passive activity where they're just collecting rent without active farming involvement, then it would typically not be subject to SE tax even for general partners and shouldn't flow to Box 14c. The key factors are: 1) Is the rental activity integrated with the active farming operations? 2) Does the partnership provide substantial services to the tenant farmers? 3) Is the rental on a crop-share basis where they participate in farming decisions? I'd recommend reviewing the partnership's activities carefully and possibly consulting the Section 1402(a)(1) regulations for farming partnerships to make sure you're treating this correctly.
This is such a common issue that catches a lot of people off guard! I ran into the exact same problem last year when preparing my first partnership return with mixed partner types. What really helped me was creating a simple checklist to verify the partner classifications are correct: 1. Check Box I on each K-1 - make sure "GP" is only used for general partners and "LP" for limited partners 2. Verify Box 14c (gross nonfarm income) only appears on general partners' K-1s 3. Double-check that any guaranteed payments for services are properly reported in Box 4, regardless of partner type 4. Review boxes 14a and 14b as well since these are also SE tax related Most tax software will handle the allocations correctly once you've got the partner designations set up properly. The tricky part is just knowing where to find those settings in your specific software. It sounds like you've already solved the main issue, but I'd definitely recommend spot-checking a few other SE tax related boxes just to be safe before you finalize everything.
This checklist is exactly what I needed! As someone new to partnership taxation, I've been feeling overwhelmed by all the different allocation rules. Your step-by-step approach makes it much more manageable. I'm curious about step 3 - when you mention guaranteed payments in Box 4, does this apply even if the limited partner is providing minimal services? For example, if a limited partner receives $1,200 annually just for attending quarterly partnership meetings and reviewing financials, would that still need to go in Box 4 and be subject to SE tax, or is there a de minimis threshold? Also, are there any other common boxes that get misallocated between general and limited partners that should be on this checklist? I want to make sure I'm not missing anything obvious. Thanks for sharing your experience - it's really helpful to hear from someone who's been through this learning curve!
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Slightly off topic but does anyone know if I need to report crypto transactions the same way as stock transactions on 1099B? I sold some bitcoin and ethereum last year but I didn't get any tax forms from the exchange. Do I need to report each individual crypto sale or can I just report the total gains? The tax treatment for Capital Gains / Capital Loss reporting is so confusing with crypto.
Crypto transactions are treated similar to Capital Gains / Capital Loss, but they don't come on a 1099B form unless your exchange has started issuing them (most have started for 2024). You absolutely need to report all crypto sales, but you can group them similarly to stocks - by short-term and long-term. The challenge with crypto is that you need to have tracked your cost basis yourself if your exchange doesn't provide it. Look for the "Virtual Currency" section in TaxAct rather than entering them as 1099B transactions. You'll still report the same information (date acquired, date sold, proceeds, cost basis), but the reporting format is slightly different.
I've been dealing with this exact same issue for the past few years. One thing I discovered that might help - if you're using TaxAct, there's actually a "bulk entry" feature for Capital Gains that's kind of hidden in the interface. When you get to the 1099-B section, instead of clicking "Add Transaction" repeatedly, look for a link that says something like "Enter multiple similar transactions" or "Batch entry mode." This lets you enter summary totals for transactions that have the same characteristics (same term length and basis reporting status). The key is making sure you have all your transactions properly categorized first - short-term vs long-term, and covered vs uncovered securities. You'll still need to enter them as separate summary entries for each category, but it's way faster than individual transaction entry. Just make sure to keep a detailed backup spreadsheet with all individual transactions in case the IRS ever asks for supporting documentation. I learned this the hard way when I got a CP2000 notice one year and had to reconstruct everything from my brokerage statements.
This is super helpful! I had no idea TaxAct had a bulk entry feature - I've been manually entering each transaction like a sucker for years. Do you know if this bulk entry option also handles situations where you have the same stock but purchased at different times? I have a lot of Apple shares that I bought over multiple years and sold portions of throughout 2024. I'm worried about getting the cost basis calculations wrong if I try to group them together.
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Another thing to consider when comparing income: health insurance costs! When self-employed, you can deduct your entire premium on Schedule 1, but as a W2 employee, you typically pay your portion with pre-tax dollars if it's an employer plan. Run the numbers both ways - sometimes the self-employment health insurance deduction is more valuable than you'd think, especially if you're in a higher tax bracket.
That's really helpful! Do retirement contributions work similarly between the two? With self-employment I've been using a SEP IRA, but I know W2 jobs often have 401ks with matching.
Retirement contributions have some important differences. With self-employment, SEP IRAs let you contribute up to 25% of your net earnings, potentially much more than the employee contribution limits for a 401(k). However, employer matching on 401(k)s is essentially free money that you don't get when self-employed. Even a modest 3-5% match can be worth thousands annually. Plus, some employers offer additional profit sharing that can greatly increase total retirement savings. I'd pay special attention to the vesting schedule for any potential employer match - some companies require several years of employment before the match is fully yours.
I was in your exact situation 2 years ago! One thing those calculators almost never account for properly: state taxes and how they interact with federal deductions. Make sure to run state-specific calculations too, especially if you're considering jobs in different states. Some states don't tax certain types of income or have weird rules about W2 vs self-employment.
Good point! I live in Texas (no state income tax) but was considering a remote position for a California company. Do you know if that means I'd have to pay CA state taxes even though I don't live there?
Scarlett Forster
Anyone know if there's a minimum threshold for reporting? Like if someone paid me with just one gold coin worth about $2,200, do I still have to report it? Or is there some minimum amount before the IRS cares?
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Arnav Bengali
•There's no minimum threshold for reporting income, regardless of what form it comes in. If you receive payment for services - whether it's cash, gold, crypto, or goods - it's taxable income and legally must be reported. The IRS definitely "cares" about all income.
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Ayla Kumar
This is a great question that comes up more often than you'd think! I dealt with a similar situation when I received some American Gold Eagles as payment for freelance work. The key thing to understand is that the IRS treats this as a barter transaction, and you absolutely must report the fair market value, not the face value. For your $20 Liberty coins, you'll need to determine their current market value based on gold content plus any numismatic (collector) premium. Check recent sales on reputable dealer sites or get quotes from local coin dealers. Document this valuation process - save screenshots of prices or get written quotes, because you'll want backup if the IRS ever questions your reported value. One thing to be careful about: don't just use the "melt value" (pure gold content value). Liberty coins, especially if they're in good condition, often trade for more than their gold content due to their collectible nature. Make sure you're capturing the full fair market value that someone would actually pay for those specific coins in their current condition. Also remember that this establishes your cost basis in the coins for when you eventually sell them - another reason to document the valuation carefully now!
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Carmen Vega
•This is really helpful advice! I'm curious though - when you say to document the valuation process, how detailed does that documentation need to be? Like if I get quotes from three different coin dealers, is that sufficient, or should I also be taking photos of the coins' condition and getting some kind of formal appraisal? I want to make sure I'm covering all my bases in case the IRS decides to take a closer look at this later.
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Emma Davis
•For documentation, you don't necessarily need a formal appraisal unless the coins are particularly rare or valuable beyond their gold content. Three dealer quotes would be excellent documentation - that shows you made a good faith effort to determine fair market value. I'd also recommend taking clear photos of both sides of each coin showing their condition, and noting the date you received the quotes since precious metals prices fluctuate daily. If the coins are common dates in typical circulated condition, dealer quotes plus photos should be more than sufficient. However, if you have key dates, mint errors, or coins in exceptional condition that might have significant numismatic premiums, then a formal appraisal from a certified coin appraiser might be worth the cost for that extra protection. The IRS generally accepts reasonable valuation methods as long as you can show you made a legitimate effort to determine fair market value. Your approach of getting multiple dealer opinions sounds very reasonable!
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