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Rewatched the movie and I think we all missed a key line where Belfort talked about "ratholing" cash. In broker language, this means hiding money to avoid reporting it. So money in his US accounts was probably already not fully reported as income. Basically: 1. Make money through stock fraud 2. Some goes into official company accounts (reported) 3. Some goes into personal accounts but not reported as income to IRS 4. Move the unreported money offshore to hide it further 5. Bring it back as "loans" that aren't taxable The issue wasn't moving money between accounts - it was that the money wasn't properly reported as income in the first place, THEN moving it around to make it harder to trace. Classic layering in money laundering.
Oh this actually makes perfect sense! So he wasn't fully reporting income to begin with, then hiding that unreported income offshore to create another layer of protection from the IRS. And then the "loan" strategy to bring it back completed the whole scheme. I guess the movie doesn't spell this out clearly enough - it makes it seem like all the money was already in his normal accounts, but those accounts probably had a mix of reported and unreported funds. Thanks for clearing this up!
This thread has been incredibly helpful! I work in tax preparation and get questions like this all the time. The confusion about the Wolf of Wall Street scheme is super common because the movie simplifies the financial crimes for entertainment purposes. What most people don't realize is that having money in a US bank account doesn't automatically mean it's been properly reported as taxable income to the IRS. Banks report interest earned and certain transactions, but they don't tell the IRS "this deposit represents taxable income." That's the taxpayer's responsibility. In Belfort's case, he was likely using a combination of techniques: underreporting income on his tax returns while depositing the full amounts in US accounts, then moving the unreported portions offshore to create distance from the IRS. The cash smuggling violated currency reporting laws regardless of whether taxes were paid, and the Swiss accounts were used to eventually bring money back as "loans" to avoid taxation. The key lesson here is that tax evasion often involves multiple violations - not just avoiding income tax, but also violating currency reporting requirements, banking regulations, and money laundering statutes. It's never just about one simple scheme.
This is such a helpful thread! I'm dealing with a similar situation but with a twist - we lived in our house for 2 years, then moved out and rented it for 1.5 years, then moved BACK in for another year before converting it to a rental again for the past 2 years. From what I'm reading here, it sounds like only that first rental period (the 1.5 years before we moved back) would count as "non-qualified use" since it happened before our final period of primary residence use. The recent 2-year rental period after we moved out for good wouldn't count against the exemption. Does that sound right? This Publication 523 stuff is so confusing with all the back-and-forth living situations. I'm wondering if I should try one of those services mentioned here to get a proper analysis before I make any assumptions about my tax liability.
You've got it exactly right! Your understanding of the non-qualified use rules is spot on. Since you moved back into the property and used it as your primary residence after that first rental period, only that initial 1.5-year rental period would count as non-qualified use. The final 2-year rental period after you moved out for good gets the exemption under the "after last use as primary residence" rule. So you'd potentially have to pay capital gains on about 30% of your profit (1.5 years out of 5 total years), but the remaining 70% should qualify for the Section 121 exclusion assuming you meet the other requirements. Just make sure you have good documentation of when you lived there versus rented it out - lease agreements, utility bills, voter registration changes, etc. Given the complexity of your situation with multiple moves, getting a professional analysis like some others mentioned here might be worth it to make sure you're calculating everything correctly, especially if there's a substantial gain involved.
I'm a tax professional and want to clarify something important that's been mentioned but might get lost in all the discussion - you absolutely need to keep detailed records of your occupancy periods and rental periods. The IRS can and will ask for proof if they audit this exemption. Beyond just utility bills and lease agreements, consider keeping: property tax records showing homestead exemptions during primary residence periods, insurance changes from homeowner's to landlord policies, any correspondence with property management companies, bank statements showing rental income deposits, and maintenance records that distinguish between personal use improvements versus rental property expenses. Also, while everyone's focused on the non-qualified use rules (which are correctly explained here), don't forget about mixed-use periods. If you ever lived in part of the property while renting out another part (like a basement apartment), those calculations get even more complex and you'll want professional help. The Publication 523 confusion is real - I deal with CPAs who misunderstand these rules regularly. When in doubt, get a professional opinion before you file, especially if your gain is substantial. An audit on a six-figure gain exclusion is not something you want to wing.
This is incredibly helpful advice, especially about the documentation requirements! I've been so focused on understanding the rules that I hadn't really thought about what proof the IRS would want if they questioned my exemption claim. Quick question - for the homestead exemption records, would county assessor records showing when I filed for and removed homestead status be sufficient? I'm pretty sure I have those somewhere, and I remember having to re-file when we moved back into the property after that first rental period. Also, you mentioned mixed-use situations - thankfully mine is straightforward (whole house primary residence vs. whole house rental), but I can see how that would add another layer of complexity. Thanks for the professional perspective on this!
One important thing to consider that I haven't seen mentioned - as a W-2 employee, you get certain legal protections that 1099 contractors don't have. This includes workers' compensation if you're injured on the job, unemployment benefits if they let you go, and protection under labor laws. As a 1099, you're essentially running your own business, which means you need to handle your own liability insurance and you won't qualify for unemployment if the relationship ends. This is a big consideration beyond just the tax implications.
Great question! I went through this exact decision last year when I started doing real estate work. Here's what I learned: The math really depends on your total business expenses. As a 1099, yes you'll pay the full 15.3% self-employment tax, but you can deduct SO much more - mileage (huge for real estate!), home office, phone, internet, marketing materials, continuing education, even meals with clients. One thing that helped me decide: I calculated my expected annual income and business expenses, then ran the numbers both ways. For me, the deductions saved more than the extra 7.65% in self-employment tax cost me. But also consider the non-tax factors - as others mentioned, you lose unemployment protection and workers comp as a 1099. However, you gain flexibility in how you work and when you work, which is valuable in real estate where you might need to show properties at odd hours. My advice: start tracking ALL your potential business expenses now (even before you decide) for a month or two. That will give you real numbers to work with instead of guessing. If your monthly business expenses are significant, 1099 is probably better. If they're minimal, W-2 might be the safer choice. Either way, definitely consult with a tax professional who understands real estate before making the switch!
This is really helpful advice! I'm curious about the tracking expenses part - do you have any recommendations for apps or methods that work well for real estate? I'm terrible at keeping receipts and I know that's going to be crucial if I go the 1099 route. Also, when you say "consult with a tax professional," how do I find one who actually understands real estate? I've had bad experiences with general accountants who didn't really get the industry-specific stuff.
I had my verification appointment on February 12, 2024, and my refund was deposited on March 8, 2024 - exactly 25 days later. My transcript updated on March 1 showing the release of the verification hold. I brought my driver's license, passport, social security card, W-2, last year's tax return, and a utility bill. The agent said I was overprepared but that it made the process smoother. Check your transcript on April 15 and April 22 - those should be key update dates based on your Monday appointment timing.
The timeline really varies, but here's what I've learned from going through this process twice. After my verification appointment, it took about 3 weeks for my transcript to update with code 971/571 showing the identity hold was released. Then another 2 weeks for the actual refund to hit my account - so 5 weeks total. Key things that helped speed mine up: - Brought original documents (not copies) - Had my AGI from last year memorized - Asked the agent to notate my file that verification was successful The 9-week timeframe is their maximum, but most people I know got theirs between 3-6 weeks. Keep checking your transcript on Wednesdays - that's when most updates happen. And don't stress if WMR still shows "processing" - it's notoriously slow to update after verification appointments. Good luck with your appointment Monday! The plumbing gods will hopefully smile upon your refund timing š§
Anna Stewart
One big mistake I made with my business vehicle - I didn't take photos of the odometer on January 1st and December 31st each year! IRS auditor flagged this and I had a nightmare proving my mileage. Also get a good app to track trips - I use MileIQ and it's saved me tons of time.
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Layla Sanders
ā¢MileIQ is good but I switched to Everlance which seems to classify trips more accurately. Also stores receipts for gas/charging in the same place which is nice for actual expenses method.
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Anna Stewart
ā¢Thanks for the suggestion! I'll check out Everlance. My biggest hassle with MileIQ was having to manually correct a lot of the auto-classifications, especially for frequent trips that sometimes were business and sometimes personal.
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Liam Sullivan
Great discussion everyone! As someone who went through this exact decision last year with my Tesla Model Y for my consulting business, I wanted to add a few practical tips: 1. **Documentation is everything** - I use a simple spreadsheet with columns for date, starting odometer, ending odometer, destination, and business purpose. Takes 30 seconds per trip but saved me during a recent audit. 2. **The business use percentage calculation** - Don't just estimate! Track for a full month to get an accurate baseline, then use that to project your annual percentage. Mine ended up being 42% which was higher than I initially thought. 3. **Consider the long-term strategy** - I started with actual expenses method because the Tesla's depreciation in year 1 was substantial. But run the numbers both ways - sometimes standard mileage wins, especially in later years when depreciation decreases. 4. **Tesla-specific tip** - Keep all your Supercharging receipts if you go with actual expenses. The app makes this easy, and electricity costs add up faster than you'd think for business driving. Also want to echo what others said about state incentives - I got a $2,000 state rebate that I almost missed because I didn't research it until after purchase. Check your state's energy department website!
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Zoe Papadopoulos
ā¢This is incredibly helpful! I'm just starting my research on this and feeling pretty overwhelmed by all the different rules and requirements. Your point about tracking for a full month to get an accurate baseline is really smart - I was planning to just estimate but you're right that actual data would be much better. Quick question about the Tesla-specific Supercharging receipts - does the Tesla app automatically save these in a format that would work for tax purposes, or do you need to export them somehow? I'm trying to get all my documentation systems set up before I actually buy the car so I don't miss anything important from day one. Also, did you find any challenges with the IRS accepting electric vehicle charging costs as equivalent to gas expenses when you used the actual expenses method?
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