I'm really sorry this happened to you - missing the 83(b) election deadline is one of those gut-punch moments that so many startup employees experience. The 30-day window is unfortunately non-negotiable, and I've seen countless people in similar situations over the years. Since your shares had a $0.00 FMV at grant, you would have had essentially no tax liability if you'd filed the election on time. Now you'll be taxed as ordinary income on whatever the fair market value is at each vesting date. Given that it's been about 1.5 years since your grant, your company may have had one or more 409A revaluations that could significantly impact your tax bill. My advice: reach out to your HR or equity administration team immediately to get the current 409A valuation. This will help you estimate what you'll owe when your first 25% vests. If the valuation has stayed relatively flat, your tax impact might be minimal. But if your company has grown or raised funding, you need to start preparing financially. Consider setting aside 35-45% of the estimated vested share value for taxes (this covers federal, state if applicable, and payroll taxes for most brackets). Also ask about your company's policy on share sales - if they don't allow employees to sell shares to cover taxes, you'll need to pay out of pocket. The good news is there are no penalties for not filing the election, and your cost basis will be stepped up to the FMV at vesting, so you won't face double taxation on sale. It's not the end of the world, just requires more careful tax planning going forward.

I'm really sorry you're dealing with this - the missed 83(b) election is unfortunately a very common mistake that happens to so many startup employees. The 30-day deadline is absolute with no exceptions, so there's no way to retroactively file it now. Since your equity had a $0.00 fair market value when granted in January 2024, you would have owed virtually nothing in taxes if you had filed the election on time. Now you'll face ordinary income tax on the fair market value of your shares as they vest, which could be significant if your company's valuation has increased over the past 1.5 years. The most important thing now is to get ahead of the tax planning. I'd recommend immediately requesting the current 409A valuation from your company's finance or HR team so you can estimate what you'll owe when your first 25% vests. If your startup has raised funding or grown substantially, this could be a meaningful tax bill that you'll need to pay out of pocket (since most private companies don't allow share sales to cover taxes). Start setting aside cash now - generally 35-40% of the estimated vested share value should cover federal income tax, state taxes if applicable, and payroll taxes. Also consider whether you'll need to make quarterly estimated tax payments to avoid underpayment penalties. The silver lining is that there are no penalties for missing the election, and your cost basis will be stepped up to the FMV at each vesting date, so you won't be double-taxed when you eventually sell. It's definitely not ideal, but with proper planning, it's very manageable.

question - if I estimate now using FreeTaxUSA 2023 software and create an account, can I just log back in when I have my actual W-2 and 1099 forms and file from there? or would I need to start over?

Thanks for the heads up about the early release! I've been using FreeTaxUSA for the past few years and really appreciate being able to do tax planning before the rush. One tip I'd add - if you're estimating now, make sure to save different scenarios. I usually create versions with conservative estimates and then more optimistic projections to see the range of what I might owe or get back. Also worth noting that if you have any major life changes planned (marriage, new job, etc.), you can model those too to see how they'd impact your taxes. Really helps with financial planning for the year ahead.

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?

One aspect that hasn't been mentioned yet is the estate planning angle of this strategy. The "die" part of "buy, borrow, die" is actually crucial for making the whole thing work long-term. When someone dies, their heirs inherit assets with a "stepped-up basis" - meaning the cost basis resets to the fair market value at death. So if Musk bought Tesla stock at $10/share and it's worth $200/share when he dies, his heirs inherit it as if they bought it at $200/share. All those unrealized gains from $10 to $200 are never taxed. This is why the ultra-wealthy can keep rolling over loans indefinitely. They don't necessarily need to pay them back during their lifetime - the estate can sell inherited shares (with no capital gains tax due to stepped-up basis) to pay off any outstanding loans after death. It's a pretty remarkable feature of our tax code that essentially allows generational wealth to avoid capital gains taxes entirely. The heirs start fresh with a new basis, and the cycle can continue for generations.

For simple record-keeping, I'd recommend starting with a basic spreadsheet or even a notebook where you track every payment and expense as it happens. Create columns for date, amount, client/source, payment method (Zelle, etc.), and description. For expenses, note what it was for and keep photos of receipts on your phone. Many freelancers use apps like QuickBooks Self-Employed, FreshBooks, or even just a dedicated business bank account to keep everything separate from personal finances. The key is consistency - update your records weekly, not once a year when you're panicking about taxes. For deductions you might be missing: home office percentage (if you work from home), business use of your phone/internet, software subscriptions, equipment depreciation, professional development courses, business meals with clients, and even mileage if you travel to client meetings. Keep everything documented with dates and business purposes. The most important thing is to start NOW, even if your system isn't perfect. A simple but consistent approach beats a fancy system you never use. And definitely open a separate savings account for those tax payments - automate transferring 30% of each payment immediately so you're not tempted to spend it.

You definitely need to report that $6,500 as income on your tax return! The payment method doesn't change your tax obligations - whether you received payment through Zelle, cash, check, or any other method, income from your freelance graphic design work is taxable. Since you didn't receive 1099 forms, don't worry - individual clients aren't required to send them unless they paid you $600+ AND you're not incorporated. But the absence of a 1099 doesn't make your income tax-free. You'll need to report this on Schedule C as self-employment income, which means you'll owe both regular income tax AND self-employment tax (about 15.3% for Social Security and Medicare). I'd recommend setting aside 25-30% of future freelance payments for taxes. The good news is you can deduct legitimate business expenses like design software subscriptions, computer equipment, portion of your home internet used for work, etc. Make sure to keep receipts and records. Going forward, if you expect similar income levels, consider making quarterly estimated tax payments to avoid underpayment penalties. The IRS expects taxes to be paid throughout the year, not just at filing time. Don't stress too much - this is a very common situation for freelancers. Just make sure to report it properly and keep good records of both income and business expenses!

Hey Isabella! I was in the exact same boat last year with my Uber Eats and DoorDash income. The good news is you don't need to stress about separating tips from base pay - they're all treated as self-employment income on your taxes. Here's what I learned: Your entire 1099-K amount ($24,680) goes on Schedule C as gross receipts. The IRS doesn't care how much was tips versus base pay because you're an independent contractor, not an employee. What REALLY matters is tracking your business expenses to offset that income. I saved over $3,000 in taxes by properly deducting: - Mileage (this is huge - 67 cents per business mile for 2024) - Phone bill percentage used for work - Hot bags, car phone mounts, etc. - Car maintenance and repairs - Even a portion of car insurance For mileage, if you didn't track everything, try using your delivery history to estimate. Count your total deliveries and multiply by average miles per delivery (usually 3-5 miles depending on your area). TurboTax will walk you through Schedule C step by step when you select "self-employment income." Don't overthink the tip separation - focus on maximizing your legitimate business deductions instead!

Isabella, I totally get the panic about that 1099-K amount! I went through the same thing my first year doing gig work. Everyone here is right - you don't need to separate tips from base pay for tax purposes since you're an independent contractor. One thing that might help ease your mind: that $24,680 is your GROSS income, not what you'll actually pay taxes on. After you deduct business expenses on Schedule C, your taxable income will be much lower. Since you mentioned using TurboTax, here's a tip that saved me tons of time: When you get to the self-employment section, TurboTax will ask about your business expenses in plain English. It'll specifically ask about vehicle expenses, and you can choose between actual expenses or the standard mileage deduction (usually better for gig workers). Don't forget about smaller expenses that add up: insulated bags, phone chargers, even hand sanitizer you bought for deliveries. Keep receipts going forward, but for this year, try to estimate what you spent on delivery-related items. The key is being reasonable and honest about your deductions. The IRS expects gig workers to have these types of expenses, so don't be afraid to claim legitimate business costs that helped you earn that income!