I recently read that Elon actually did pay the largest individual tax bill in US history - something like $11 billion in 2021 when he exercised a bunch of Tesla options that were about to expire. So the "never pay taxes" strategy isn't entirely accurate. What I think happens is that these billionaires try to time when they realize income. They can defer for years using loans, but eventually they do have to realize some income and pay some taxes - they just try to do it in the most advantageous way possible. From what I understand, the ultra-wealthy also use charitable donations strategically. They donate appreciated stock directly to charities, getting a deduction for the full market value without having to pay capital gains tax on the appreciation.

Has anyone here actually tried implementing a smaller version of this strategy? I have about $200k in company stock that's appreciated a lot, and I'm considering taking out a loan against it to renovate my house instead of selling the shares and triggering capital gains. Not exactly Elon Musk level, but I'm wondering if the "buy, borrow" part of the strategy makes sense for regular-ish people too? What interest rates are banks offering on these securities-backed loans for non-billionaires?

Another thing to consider is whether your employer reported this correctly. My company did something similar but after talking to our benefits dept, we realized some of the courses should have been classified as job-required training (non-taxable) rather than graduate education. If any of your courses directly relate to your current position and maintain (not improve) your skills, you might be able to get HR to recategorize them.

I'm dealing with a similar situation right now as a federal employee taking graduate courses. One thing that helped me was requesting a detailed breakdown from HR showing exactly how they calculated the taxable portion. In my case, they had mistakenly included some fees that should have been excluded (like student activity fees and parking passes) which reduced my taxable benefit by about $800. Also, make sure they applied the $5,250 annual exclusion correctly - some payroll departments mess this up if you have courses spanning multiple calendar years. You might also want to keep detailed records of any out-of-pocket expenses you paid (books, supplies, etc.) since these could qualify for education credits even if the tuition itself was employer-paid. The IRS allows you to claim credits on qualified expenses even when the tuition was covered by your employer's taxable benefit. Don't panic too much - yes, you'll owe taxes on that amount, but it's not like you have to come up with $27k in cash. It just gets added to your regular income and taxed at your marginal rate.

I'm dealing with similar GBTC reporting issues on my E-Trade 1099-B! What's really frustrating is that some of my transactions show completely different basis amounts than what I actually paid, and others are missing basis information entirely. I've been keeping detailed records in a spreadsheet since I started investing in crypto-related assets, so I know exactly what I paid for each purchase. But seeing these discrepancies on the official 1099-B form is making me second-guess everything. Has anyone had success contacting E-Trade directly about these reporting errors? I'm wondering if they can issue corrected forms or if I just need to override everything manually when filing. The last thing I want is to overpay on taxes because of their incomplete reporting, but I also don't want to do anything that might cause issues with the IRS later. Thanks for starting this thread - it's reassuring to know I'm not the only one dealing with this mess!

I'm going through the exact same headache with my E-Trade 1099-B and GBTC! It's such a relief to find this thread because I was starting to think I was doing something fundamentally wrong with my record-keeping. My situation sounds almost identical to yours - some transactions showing "basis not reported to IRS" and others with cost basis amounts that are completely different from what I actually paid. I've been tracking everything meticulously in Excel since I started buying GBTC two years ago, so I know my numbers are right. What's particularly confusing me is that some of my earlier GBTC purchases from 2023 are showing correct basis information, but my 2024 purchases are all messed up. I'm wondering if this has something to do with the trust-to-ETF conversion that happened or if E-Trade just changed how they handle crypto-adjacent reporting. Based on what everyone's saying here, it sounds like I should just override the imported numbers in TurboTax with my actual purchase records and not worry too much about the discrepancies. Has anyone who's done this already filed their return? I'm curious if there were any follow-up questions or issues from the IRS. Thanks for posting this - definitely going to check out some of the tools people mentioned to double-check my work!

Has anyone considered the QBI deduction (Section 199A) impact when deciding between S Corp vs. sole proprietor? I've heard that having too high of a salary in an S Corp can reduce your QBI deduction.

Great discussion everyone! As someone who made the S Corp election two years ago in a similar situation, I wanted to share some real-world experience. My consulting business was pulling in about $280k, and I set my reasonable salary at $160k (just under the OASDI limit at the time). Even with that salary level, I still saved roughly $3,500 annually on Medicare taxes from the distributions. One thing I learned the hard way - make sure you factor in the quarterly estimated tax payments on your distributions. Unlike salary where taxes are withheld automatically, you're responsible for making those payments yourself. I got hit with underpayment penalties my first year because I didn't adjust my estimates properly. Also, the administrative burden is real. Beyond the extra tax filings, you need to run actual payroll (even if it's just for yourself), maintain corporate minutes, and keep business and personal finances completely separate. It's definitely more work than being a sole proprietor, but the tax savings and liability protection have been worth it for my situation. The key is running the numbers for YOUR specific circumstances - income level, state taxes, industry standards for reasonable compensation, and your tolerance for additional paperwork and compliance requirements.

I'm dealing with a similar situation with my restaurant's ERC claim. Paid 28% to a firm that promised "specialized expertise" but it turned out they just had me fill out basic forms and submit payroll records. The whole process took them maybe 3 hours total for a $45,000 claim. What's really frustrating is that I later discovered my CPA could have handled the entire filing for a flat $2,500 fee, but the ERC company made it sound like it required some kind of specialized tax law knowledge that only they possessed. I'm definitely interested in exploring legal options, especially after reading about the class action mentioned here. Has anyone found success getting partial refunds from these companies outside of lawsuits? I'm wondering if it's worth trying to negotiate directly with them first before going the legal route.

I'm in a very similar boat with my accounting practice - I've been helping several clients navigate the aftermath of working with these ERC mills. What I've seen consistently is that legitimate ERC claims typically require 8-15 hours of work when done properly, including eligibility analysis, documentation review, and form preparation. The problem is many of these contingency firms were essentially running claim factories, processing hundreds of applications with minimal individual attention. A 25% fee on a properly vetted claim might be reasonable, but not when they're just plugging numbers into software and hoping for the best. One thing I'd strongly recommend is getting a second opinion on your claim's legitimacy before your refund comes through. With the IRS crackdown, they're auditing a significant percentage of ERC claims now, and if your original firm cut corners on documentation, you could face penalties that far exceed any contingency fee dispute. I've been referring clients to services like taxr.ai for post-submission reviews to make sure everything is properly documented. Better to identify potential issues now than during an audit later.