I'm going against the grain here, but I think most early-stage founders overthink bookkeeping. Unless you've raised capital or have complex revenue, a simple spreadsheet with income and expenses categorized is often sufficient for the first 6-12 months. I started with a Google Sheet tracking everything manually, then moved to Wave when we hit about $5k in monthly revenue, and finally QuickBooks when we raised our seed round. You don't need fancy systems when you're just getting started - you need clarity on cash flow and basic expense tracking. The most important things early on: 1. Separate business and personal finances completely 2. Keep receipts for EVERYTHING 3. Pay yourself a consistent amount (even if small) 4. Track founder expenses separately

Has anyone tried Bench? My co-founder and I are debating between hiring them or just DIYing with QuickBooks.

One thing nobody has mentioned yet about Section 83(b): if your shares are already fully vested when granted, you DON'T need to file this! I wasted so much time panicking about this before my accountant told me it only applies to shares with vesting restrictions. Also, make sure you understand the difference between restricted stock and stock options - they're treated completely differently for tax purposes. Section 83(b) elections only apply to restricted stock, not to stock options. I got confused because my company grant included both types and I almost filed unnecessarily for the options portion.

Something super important that nobody mentioned: When you file Section 83(b), you need THREE copies! One for the IRS, one for your employer, and one to attach to your tax return for that year. I almost messed this up. Also, make sure you're using the right address for your IRS service center - it differs based on where you live. And don't forget you need proof of mailing (certified mail with return receipt) to prove you sent it within the 30-day window.

Am I the only one who thinks it's completely ridiculous that we get taxed on something we don't even receive?? This is just another example of the government finding ways to take more of our money. If I'm not getting any actual benefit until I'm DEAD, how is that income?!?!

Check your husband's actual paystub for the amount of imputed income. The tax impact is usually pretty small. For example, I'm 42 and have $150,000 in coverage (so $100,000 above the threshold). The monthly imputed income on my paycheck is only about $8, which means the actual tax I pay is just a couple dollars per paycheck. Might not be worth reducing your coverage just to save such a small amount.

Did your reimbursement checks come with any kind of letter or explanation? Usually there's some paperwork that explains what the payment is for specifically, which would help determine if it's taxable. When my cousin got a similar reimbursement after her beauty school closed down, there was a whole packet explaining the tax implications.

If you received Form 1098-T from your school before it closed, make sure you keep that for your records too. It shows what you paid for qualified education expenses and will help determine if these reimbursements are taxable or not.

Just so everyone knows, not all second look services are created equal. I paid $400 for one last year and they literally just ran my numbers through a different tax software and found nothing. Make sure you ask exactly what their process involves before paying. Ask if they specialize in your industry and what their success rate is for businesses similar to yours. Also ask if they've worked with businesses in your specific state, as state tax opportunities vary widely.

Speaking as someone who handles small business accounting, there's another benefit to second looks that nobody's mentioned yet - they sometimes catch ERRORS that could lead to audits. Last year I had 3 clients get second looks and for one of them, we actually discovered their previous accountant had improperly classified some expenses that could have raised red flags with the IRS. The second look saved them from potential audit headaches, not just money.