Great question! I've been navigating similar territory with my small C-corp (2 employees including myself). One thing I learned that might help is that the IRS has specific safe harbors for certain fringe benefits that make them less likely to be challenged. For example, de minimis benefits (small value items like occasional meals, coffee, office snacks) have a $75 per item threshold and don't require complex documentation. Working condition fringe benefits (like business cell phones, professional subscriptions, work-related education) are also relatively safe if you can demonstrate they're primarily for business use. The key insight my tax advisor shared is that the IRS is more concerned with the overall compensation package being reasonable than with individual fringe benefits. So if your total compensation (salary + benefits) is within industry norms for your role and experience, you're in much safer territory. One practical tip: consider establishing a formal employee handbook that outlines your company's fringe benefit policies, even if you're the only employee. It demonstrates that you're operating as a legitimate business entity rather than just trying to convert personal expenses into business deductions. Have you considered what your total compensation strategy will look like? That might help determine which fringe benefits make the most sense for your situation.

This is exactly the type of question I had when I first incorporated my small business as a C-corp! The good news is that size generally doesn't matter for most fringe benefits - even a one-person C-corp can take advantage of these tax exclusions. However, there are some key compliance considerations you'll want to be aware of: **Business Purpose Requirement**: Benefits like meals need to serve a legitimate business purpose and generally be provided on business premises. You can't just deduct personal grocery bills by running them through the corporation. **Reasonable Compensation**: The IRS scrutinizes small C-corps to ensure that total compensation (salary + benefits) is reasonable for the services provided. They don't want you avoiding payroll taxes by disguising compensation as tax-free benefits. **Documentation**: Keep detailed records showing the business purpose for each benefit. Corporate resolutions establishing benefit policies before implementation can be crucial if you're ever audited. **Non-discrimination Rules**: While these are more relaxed for very small companies, you still can't structure benefits to unfairly favor owner-employees over regular staff. Some of the safest fringe benefits for small C-corps include: health insurance premiums, educational assistance up to $5,250 annually, de minimis benefits under $75 per item, and working condition fringe benefits like business cell phones. The key is treating your C-corp as a legitimate business entity with proper corporate governance, not just a vehicle for personal tax savings. Have you considered consulting with a tax professional who specializes in small business structures? They can help you set up compliant benefit programs from the start.

Does anyone know if there's a minimum salary requirement for S Corps? My CPA told me I need to pay myself at least $40k, but a buddy with an S Corp says he only pays himself $30k on $90k of revenue. I'm confused by all the different advice.

This is such a common struggle for new S Corp owners! I went through the exact same thing when I converted my consulting business two years ago. Based on my research and discussions with my CPA, here's what I learned: The IRS doesn't have a magic formula, but they do look at several factors - what you'd pay someone else to do your work, your geographic location, your experience level, and the time you spend on the business. For a web developer in the Midwest making $120k net profit, I'd lean toward the higher end of reasonable compensation - probably around $70-80k salary. Since you're doing ALL the work (coding, design, client meetings), you can't really argue that a significant portion of the profit comes from business assets or other employees. One thing that helped me was looking at actual job postings for senior web developers in my area and calculating what a full-time equivalent would make, then adjusting slightly for the entrepreneurial risk/reward factor. I kept screenshots of those job postings as documentation. Also, don't forget that paying yourself a higher salary isn't necessarily "bad" from a tax perspective - yes, you'll pay more in employment taxes, but you'll also build up more Social Security credits and potentially qualify for higher unemployment benefits if needed. The key is finding the sweet spot that's defensible to the IRS while still providing S Corp tax benefits.

Anyone know if it makes a difference whether you set up the campaign for yourself vs for someone else? Like if I create it for my brother but use my account, does that make me responsible for taxes?

Great question! I went through something similar when helping my neighbor after a house fire. The key thing to remember is that donations for personal hardships like legal fees are generally treated as gifts, not taxable income to the recipient. However, there are a few important considerations: First, keep detailed records of all donations and how the money is used - this documentation will be crucial if there are ever any questions. Second, be very clear in your campaign description that the funds are for personal legal expenses, not for any business purpose or in exchange for goods/services. Regarding who sets it up - it doesn't fundamentally change the tax treatment, but having your cousin create it directly might be simpler administratively. If you set it up and the money flows through your account first, you'll technically be making a gift to him when you transfer the funds (though this usually doesn't create tax issues either). One heads up: if the campaign raises over certain thresholds (typically $20,000+ with 200+ transactions), the platform may issue a 1099-K form. Don't panic if this happens - it doesn't automatically make the money taxable. You just need to properly document on the tax return that these were non-taxable gifts for personal expenses. Consider consulting with a tax professional if you end up raising a substantial amount, just to make sure everything is handled correctly.

Couple things to add from my experience with NSOs: 1) Consider the risk! You're putting real money into a private company that might never go public or get acquired. I exercised options at a startup that later failed - lost $15k and still had to pay taxes on phantom income. 2) If you wait till after IPO, there's usually a 180-day lockup period where you can't sell shares even though they're public. Market could tank during that time. 3) Ask if your company offers early exercise with 83(b) election - lets you exercise unvested options and starts your capital gains clock earlier. 4) Don't forget state taxes! California especially kills you on this stuff. 5) Some companies have programs to help with exercise costs or cashless exercises. Worth asking about.

This is exactly the kind of situation where having all the right information upfront makes a huge difference. Based on your numbers (7,250 total options with those strike prices vs $5.93 FMV), you're looking at roughly $36k in taxable income if you exercise everything at once - that's a significant tax bill to plan for. A few practical considerations for your timeline: 1) Get clarity on your vesting schedule and any acceleration clauses that might trigger at IPO. Sometimes unvested options accelerate when companies go public. 2) Find out your company's IPO timeline. If it's 6+ months away, you might have time to exercise in stages across tax years to manage the tax hit. 3) Ask your company about any employee programs they offer - stock loan programs, cashless exercise options, or even tax gross-up assistance (some companies help cover the tax burden). 4) Consider your personal financial situation. Can you afford both the exercise cost (~$4,600 total) AND the tax bill on ~$36k of ordinary income? Don't put yourself in financial hardship for equity that's still speculative. The fact that your current tax advisor seems out of their depth is concerning. This really calls for someone with specific equity compensation experience, whether that's a specialized CPA or getting direct guidance from the IRS on proper reporting requirements.

did you check if you have any freezes or holds? sometimes they dont show up obvious on the transcript but theyre there

A negative balance definitely means the IRS owes you money! With your tax liability at $0 and that negative balance, you likely received refundable credits like the Child Tax Credit or Earned Income Credit that created the overpayment. The delay could be due to identity verification, income verification, or just processing backlogs. I'd recommend calling the IRS refund hotline at 1-800-829-1954 to check if there are any issues holding up your refund. You can also try calling early morning (7-8am) for better chances of getting through!