I hadn't even thought about checking my credit report. That's a really good point. Do you know if business debts always show up on personal credit reports? And if I do find something, should I dispute it the same way as the tax debt?

Business debts can absolutely show up on your personal credit report, especially if the business was a sole proprietorship or if your father used your personal information to guarantee any loans. Even with corporations or LLCs, lenders often require personal guarantees from owners for small businesses. If you find unauthorized accounts or loans, you would dispute them differently than tax debt. For credit report issues, you'd file disputes directly with the credit bureaus using their fraud departments. You may also need to file a police report for identity theft, which some creditors require before removing fraudulent accounts. This is separate from the IRS process, but equally important for your financial health.

Intent doesn't really matter when you're talking about $105K in tax debt that could follow this person for life. Even if the father meant well (which seems doubtful), he's essentially saddled his child with a massive financial burden without consent. That's not something you do to someone you care about, regardless of intention.

Isn't that kind of playing with fire though? I thought the IRS looks closely at businesses that don't make much profit and might consider them hobbies instead of actual businesses?

You're absolutely right to be concerned about the hobby loss rules. The key is having a genuine profit motive and running it like a real business. Keep separate bank accounts, maintain good records, and ideally make a profit in at least 3 of 5 consecutive years. My photography business actually became profitable in year 2, which helped establish it as a legitimate business. If you're just creating a "business" solely to deduct personal expenses with no real intention of making a profit, that's when you're asking for trouble with the IRS. But if you genuinely start a side business related to your expertise where you can legitimately use the equipment, it can work.

I've definitely thought about this approach, but I'm worried about coming across as difficult or not being a "team player." The company culture is very much about "making it work" even when resources are limited. But you're right - maybe I need to be more direct about how this impacts my ability to do the job they're paying me for.

Yeah, there was a letter but it wasn't very clear on the tax part. It explained I was getting reimbursed because the school didn't deliver the education I paid for, but nothing specific about taxes. I'm going to try contacting the Department directly to get clarification. Sounds like I should get this figured out before tax time so I don't have any surprises.

This is super important! And don't forget that if you claimed education credits in previous years based on those expenses, you might need to "recapture" those credits now that you're getting reimbursed. Tax software often misses this.

Couldn't this approach create headaches later when you switch to actual bookkeeping software? I imagine there's a lot of manual data entry and potential for errors when migrating from spreadsheets.

You make a valid point about potential migration headaches, but most early startups have such low transaction volume that it's not a major issue. When I migrated from spreadsheets to Wave, I only had about 200 transactions to deal with. It took one afternoon to set everything up properly. The bigger risk actually comes from overcomplicating things early on. I've seen founders spend thousands on comprehensive accounting systems they don't need yet, which diverts precious capital from growth. The spreadsheet approach forces you to understand your finances intimately before you delegate or automate. When you do upgrade, you'll make better decisions about what you actually need versus what's nice to have.

I used Bench for about a year. They're good if you want hands-off bookkeeping and don't have super complex needs. The main limitation I found was with customized reporting - sometimes I needed specific breakdowns for investors that their standard reports didn't provide. Their tax prep add-on was pretty solid though.

It's not ideal but you ARE receiving a benefit - free insurance coverage that would otherwise cost you money to purchase. The government views the premium payment as compensation, which makes sense if you think about it. Insurance has value even if you don't file a claim.