One thing nobody has mentioned is that Missouri has some specific state-level considerations for S-corps that differ from some other states. I'm a MO agent too, and our state taxes S-corps a bit differently than sole props. Make sure whoever you work with is familiar with MO specifically. Also, did your CPA mention anything about how the 20% QBI deduction factors into this decision? That's another big piece of the S-corp vs LLC analysis that might affect your choice.

Great point about Missouri-specific considerations! The QBI deduction interaction is crucial and often overlooked. For S-corps, the QBI deduction applies to your business income MINUS the W-2 wages you pay yourself. So if you're paying yourself a high salary (like that 70% some CPAs recommend), you're reducing the income eligible for the 20% QBI deduction. This creates an interesting balance - you want your salary high enough to avoid IRS scrutiny but not so high that you lose significant QBI benefits. In many cases, this actually supports the 50-60% salary range that others have mentioned here. Missouri also doesn't conform to federal S-corp elections automatically, so you need to make a separate state election. Plus MO has that franchise tax for S-corps that LLCs don't pay. These state-level costs should definitely factor into your breakeven analysis. I'd recommend running the numbers with both federal AND Missouri tax implications included. The total picture might be different than just looking at federal savings alone.

@Liam McGuire - I just went through this exact decision process last month! The combination of student debt stress and stock grant confusion is rough, but you can definitely figure this out. Here's my practical approach: First, don't panic about the 30-day deadline - you still have time to get the right information. Email your HR team TODAY asking for: 1) The current 409A valuation per share, 2) Your exact number of shares, 3) Your exercise/strike price (if any), and 4) Whether this is an ISO, NSO, or RSU grant (the tax treatment differs slightly). While you're waiting for those numbers, think about your risk tolerance. Filing 83(b) is essentially making a bet that your company will grow significantly over the next 4 years. If you're at a very early-stage startup with lots of growth potential, it usually makes sense. If you're at a more mature company that's already highly valued, the benefits are smaller. Given your $42k in student loans, I'd suggest calculating what that immediate tax hit would mean for your monthly budget. If it's going to stress you out financially or delay your loan payments, that's a real cost to factor in too. Sometimes the peace of mind from better cash flow is worth more than potential tax savings. One last thing - if you decide to file, make sure you send it certified mail and keep copies. The IRS is strict about the 30-day deadline and proper filing procedures. Don't let a paperwork mistake invalidate your election!

@Liam McGuire - As someone who works in equity compensation at a tech company, I see employees struggle with this decision all the time. The good news is that your situation (early career, student debt, first stock grant) is actually pretty common and manageable. Here's what I tell everyone: the 83(b) decision comes down to three key factors - current valuation, growth expectations, and your personal cash flow. Since you mentioned this is part of a promotion package, I'm guessing your company values talent retention and likely has decent growth prospects. The student loan concern is totally valid, but remember that you're not committing to monthly payments - this would be a one-time tax event that you'd handle during your regular tax filing. If the current 409A valuation is low (which it often is for earlier-stage companies), your immediate tax hit might be surprisingly small - maybe $500-2000 depending on your grant size and company stage. My recommendation: Get those specific numbers from your finance team this week, then run a simple calculation. If the immediate tax cost is less than what you'd pay in student loan interest over 2-3 months, and you believe in your company's growth potential, filing 83(b) usually makes financial sense. Don't let fear of the unknown drive this decision - get the real numbers and then you can make an informed choice. You've got this!

A quick tip if you do take this job - I make a deduction worksheet for all 1099 work. Track mileage between work sites (not commuting), any supplies you buy, portion of phone/internet if you use them for work, professional subscriptions, software, etc. Keep ALL receipts, take photos of them with your phone right away (they fade!). Also track any home office space if you do some work from home.

Just wanted to add another perspective here - I was in almost the exact same situation last year (required to work in their office, set schedule, but given a W9). After doing some research, I decided to take the job but immediately started documenting everything that showed I was really an employee, not a contractor. Things like: emails about required work hours, office policies I had to follow, equipment they provided, training materials, etc. After 6 months, I filed Form SS-8 with the IRS to get an official determination on my classification. The IRS ruled I was misclassified as a contractor and should have been an employee. Long story short - I got a refund for the extra self-employment taxes I paid, and my employer had to reclassify me and pay their portion of payroll taxes going forward. It was a bit of a process but totally worth it financially. If you take this job, document everything that shows they control how, when, and where you work. It could save you thousands later if you need to challenge the classification.

This is such a common situation unfortunately! I went through something similar last year and learned the hard way that the IRS has very specific criteria for determining employee vs contractor status. The key factors are behavioral control (do they control HOW you work?), financial control (do they control the business aspects of your work?), and the type of relationship. Working in their office on a set schedule with their equipment strongly suggests you should be classified as a W-2 employee. The fact that they didn't mention this during interviews is concerning - legitimate contractor relationships are usually discussed upfront since they're fundamentally different from employment. At $27/hour for 20-30 hours weekly, you're looking at roughly $1,100-$3,500 in additional self-employment taxes annually compared to W-2 status. Plus you'll need to make quarterly estimated payments and handle your own benefits. I'd recommend having a direct conversation with them about proper classification before accepting. Most legitimate employers will appreciate you bringing this up professionally rather than discovering compliance issues later. If they refuse to consider W-2 status, that tells you something important about how they operate. Good luck with whatever you decide - trust your instincts on this one!

This is exactly why I always research employment classification before accepting any position! The IRS has a really helpful publication (Publication 15-A) that outlines the specific criteria for determining worker classification. One thing that hasn't been mentioned yet - if you do end up taking a contractor position, make sure you get everything in writing. A proper independent contractor agreement should specify deliverables, deadlines, and payment terms rather than hourly schedules and office requirements. Also, keep detailed records of everything work-related if you go the W-9 route. While commuting isn't deductible, you might be able to deduct things like a portion of your phone bill, office supplies you purchase, or professional development costs depending on the nature of the work. But honestly, based on what you've described (in-office work, set hours, their equipment), this really sounds like an employee relationship. The fact that multiple people here have successfully gotten reclassified suggests it's worth having that conversation. Don't let them take advantage of you just because you need the job!

Just a heads up on something that surprised us during our C to S conversion last year - the Accumulated Adjustments Account (AAA) tracking became really important. After conversion, you'll need to carefully track AAA which is basically the post-conversion retained earnings that have already been taxed at the shareholder level. When you eventually distribute proceeds from property sales, the ordering rules for distributions can get tricky between AAA, accumulated E&P from the C corp days, and other sources. Our accountant messed this up initially and it almost resulted in some distributions being incorrectly taxed as dividends when they should have been tax-free returns of already-taxed income.

One thing I haven't seen mentioned yet is the potential impact of state taxes on this strategy. While the federal tax benefits of converting from C corp to S corp are well-documented, some states don't recognize S corp elections or have their own built-in gains taxes that could significantly impact your overall tax savings. For example, some states will continue to tax the entity as a C corporation even after federal S election, which could eliminate much of the benefit you're hoping to achieve. Other states have their own recognition periods or different rules for built-in gains. Given that you're dealing with real estate, you'll also want to consider whether your state has any special provisions for real estate held in corporate entities. Some states have additional taxes or fees for corporations holding real property that could affect your cost-benefit analysis. I'd strongly recommend getting state-specific advice from a tax professional familiar with your jurisdiction before moving forward with the conversion. The federal tax savings could be completely offset by unexpected state tax consequences.