I think we're missing something important here. The sharks aren't just passive investors - they're using their TV fame to promote these businesses. That's why they often talk about "opening doors" or using their "platform." Wouldn't the IRS consider that material participation? Like when Lori gets something on QVC or Robert promotes a fitness product on social media?

This is a fascinating discussion! One thing that might complicate the tax picture even more is that some of these Shark Tank deals involve multiple revenue streams. For example, a shark might get equity, royalties, AND licensing fees all from the same investment. The IRS would likely treat each income stream differently - the royalties as passive income on Schedule E, licensing fees potentially as active income if there's ongoing involvement, and equity distributions based on the material participation test we discussed earlier. Also, I think the promotional aspect @NebulaNinja mentioned is huge. When Mark Cuban tweets about a company or Lori gets a product on QVC, that's not just casual promotion - that's strategic business development that could easily qualify as material participation. The sharks are essentially using their personal brands as business assets, which makes the active vs passive classification even more complex. It would be interesting to know if they track their promotional activities and social media posts as "business hours" for tax purposes!

What investment platforms are you using? I've noticed that some brokerages are slower than others at reporting 1099 information to the IRS, which can cause delays in refund processing. Did you receive any CP01 notices or other IRS correspondence?

I had a similar situation last year with dividend income causing delays. The IRS transcript is definitely your best bet for getting detailed info before calling. If you do need to call, try the callback feature on 800-829-1040 - you can request they call you back instead of waiting on hold. I used it successfully last month and got called back within 3 hours instead of sitting on hold for over an hour. Just make sure you answer when they call back because they won't try again!

Has anyone considered the psychology of this? Even if it doesn't make financial sense (which everyone seems to agree it doesn't), there might be other valid reasons to quit a job. Mental health, family time, pursuing a passion, etc. Maybe reframe the question? If you really want to leave your job, perhaps focus on building that online selling business FIRST while still employed, then transition once it's generating enough income? Tax savings alone won't justify quitting, but if there are other benefits to you personally, those might tip the scales. Just something to consider.

I've been in a similar situation with multiple income streams, and I want to echo what others have said - the math almost never works out in favor of quitting for tax reasons alone. However, I'd suggest looking at some specific strategies that might help your situation without giving up that $115k: 1. Max out both your 401(k) contributions if your employers offer them - that's potentially $46,000 in pre-tax savings for 2024 ($23,000 each) 2. If either job offers HSA options, those are triple tax-advantaged 3. For your part-time work, make sure you're tracking ALL legitimate business expenses - home office, equipment, supplies, etc. The burnout you're experiencing is real and valid, but there might be other solutions. Could you negotiate remote work, flexible hours, or even a sabbatical at one of the jobs? Sometimes employers are willing to work with valuable employees to prevent turnover. If you do decide to build an online business, definitely start it as a side project first while keeping your current income. Once it's generating consistent revenue, then you can make an informed decision about transitioning away from traditional employment. Your financial security is worth more than the tax savings you'd get from a lower income bracket.

11 Has anyone actually received their 1099-K from Venmo yet for last year? I've sold way more than the $600 threshold but nothing has shown up in my account or email. Getting a bit nervous as I want to file my taxes soon.

Just wanted to share my experience for anyone still waiting on their 1099-K forms. I was in the same boat as the original poster - made about $850 through Venmo selling various items on Facebook Marketplace. I found my 1099-K in my Venmo account under Settings > Tax Documents about a week ago. It wasn't emailed to me automatically, so definitely check your account directly. The form lumps everything together as one gross amount, which initially freaked me out because I thought I'd owe taxes on money I made selling my old couch and textbooks at a loss. The key thing I learned is that the 1099-K is just an informational document - it doesn't mean you automatically owe taxes on that full amount. You'll need to determine on your own which transactions were actual taxable income versus personal property sales. Keep good records of what you originally paid for items you sold, especially if you sold them for less than you bought them for. For anyone still having trouble accessing their forms or getting through to customer service, the suggestions about third-party services in this thread seem legitimate based on other people's experiences. Tax season is stressful enough without fighting with payment app customer service!

One thing to consider - the American Opportunity Tax Credit your parents claimed might actually have been correct if they were supporting you. That credit can be claimed by whoever claims you as a dependent. But the taxable portion of scholarships above qualified education expenses is always taxable to the student, regardless of dependent status. A lot of students and parents don't realize these are separate issues. If I were you, I'd file the late return for 2023 and request first-time penalty abatement. The IRS is generally pretty understanding for first-time issues, especially with students who didn't understand the filing requirements.

Just wanted to add that the standard deduction for 2023 was $12,950 for single filers. So even if you had $14,700 in taxable scholarship income, your actual taxable income after the standard deduction would be around $1,750, putting your tax liability much lower than you're calculating. Also, don't forget that scholarships that go toward qualified education expenses (tuition, fees, books required for courses) aren't taxable. Only the portion that exceeds these expenses or goes toward room and board is taxable.