As someone who's been running a successful pet influencer business for about 18 months, I can confirm that this is absolutely doable - but you need to be strategic about it from the start. The most important thing I learned is that the IRS looks for a clear separation between personal pet ownership costs and legitimate business expenses. My golden retriever would need food, toys, and vet care regardless of his Instagram account, so those basic expenses stay personal. However, the specialized equipment I bought specifically for content creation (ring lights, backdrop stands, special treats only used for training during shoots) are legitimate business deductions. I've found success by treating this exactly like any other small business. I registered an LLC, opened a business bank account, and maintain meticulous records. Every business expense gets logged with a photo, receipt, and description of how it contributed to content creation or revenue generation. One tip that's been invaluable: I created a "content calendar" that shows planned posts and associated expenses. This helps demonstrate to the IRS (and myself) that purchases were made with specific business purposes in mind, not just impulse buys I'm trying to write off later. The profit requirement is real though - you need to show you're genuinely trying to make money, not just subsidizing pet ownership through tax deductions. Focus on building multiple revenue streams early: sponsored posts, affiliate marketing, maybe even merchandise featuring your pet.

This thread has been incredibly insightful! I'm just getting started with my rabbit's Instagram account and had no idea about the complexity involved in legitimate business deductions. One thing I'm curious about that hasn't been mentioned yet - what about equipment depreciation? If I invest in a good camera or lighting setup specifically for my pet content, can I depreciate that over time like other business equipment? And does the equipment need to be used exclusively for the pet business, or can I use it for other purposes too? Also, I'm wondering about the timing of when to start treating this as a business. Should I wait until I have some income before making business-related purchases, or is it okay to invest upfront in equipment and setup costs before generating revenue? I don't want to put the cart before the horse, but I also want to create quality content from the beginning to attract potential sponsors. The advice about maintaining separate accounts and detailed documentation is definitely noted - it seems like the key is being able to prove legitimate business intent from day one rather than trying to justify personal expenses after the fact.

Based on all the helpful responses here, it sounds like your broker is correct and you just missed the mark by one day. The "more than one year" rule is really strict - it has to be the day after the anniversary of your purchase date. For future reference, I've found it helpful to set calendar reminders a few days before the one-year mark so I don't accidentally sell too early. Even though it seems like 365 days should be enough, that extra day makes all the difference for tax purposes. Since your broker already reported it as short-term on the 1099, you'll need to report it that way on your return to avoid any IRS matching issues. It's frustrating when you're off by just one day, but at least now you know the exact rule for next time!

This is such a common mistake that catches so many investors off guard! I learned this the hard way a few years ago with some Apple stock I thought I'd held long enough. One thing that might help going forward is to think of it as needing to hold until the day AFTER the anniversary of your purchase date. So if you buy on November 15th, you need to hold until at least November 16th of the following year to qualify for long-term treatment. The tax difference can be significant too - short-term gains are taxed as ordinary income (potentially up to 37% for high earners), while long-term rates max out at 20% for most assets. That one extra day of holding could have saved you quite a bit depending on your tax bracket. Unfortunately, since your broker has already issued the 1099 reporting it as short-term, you'll need to report it that way on your return. But definitely keep this rule in mind for future trades!

Just so you know, you might want to look at alternatives to TurboTax too. I used H&R Block Premium last year for a very similar situation (3 rental properties, side business, backdoor Roth) and found it handled everything well for a lower price than TurboTax Self-Employed.

Based on your complex tax situation, you definitely need TurboTax Self-Employed. Here's why: Your rental properties in multiple states require multi-state tax filing capabilities that only Premier/Self-Employed versions handle well. The Self-Employed version is better for this since you also have 1099 consulting income. For your Canadian accounts ($80k CAD retirement + $35k CAD checking/savings = $115k CAD total), you'll need to file FBAR (FinCEN Form 114) since you exceed the $10,000 USD threshold. Self-Employed includes guidance for these foreign account reporting requirements. The backdoor Roth IRAs (both regular and mega) require careful Form 8606 reporting to avoid double taxation, and Self-Employed has better guidance for these transactions. Your Airbnb STR situation using the 14-day rule needs proper reporting to avoid audit flags - Self-Employed handles short-term rental income better than lower tiers. The consulting work from home likely qualifies for home office deductions, which Self-Employed specializes in calculating correctly. Given all these moving parts (multiple income streams, multi-state rentals, foreign accounts, complex retirement contributions), the Self-Employed version will save you more in properly claimed deductions than the extra cost over Premier. The specialized guidance alone is worth it for your situation.

I used Marcus to pay my taxes through TurboTax last year and had a similar experience to what others have mentioned - it took about 4-5 days to process, which was nerve-wracking at first. The payment did go through successfully, but I learned a few things that might help you. First, make sure you have sufficient funds in your account with a little buffer, as Marcus sometimes puts a temporary hold on the full amount while processing. Second, I noticed that Marcus sends email notifications for large transfers like tax payments, so keep an eye on your email for any alerts. If you're really worried about it, you might want to call Marcus customer service and give them a heads up about the upcoming tax payment. When I did this, they noted it on my account which seemed to help with the processing. Their customer service is actually pretty good compared to other online banks. The Electronic Funds Withdrawal option that Zara mentioned is definitely worth considering for next year - I've heard good things about it being more reliable with online banks.

I actually used Marcus through TurboTax for my federal taxes this year and it went smoothly, but I did have one hiccup that might be helpful for you to know about. The payment initially showed as "pending" for about 6 days, which had me pretty worried since most of my other bank transfers with Marcus usually clear in 1-2 days. What I discovered by calling Marcus was that they have additional fraud protection protocols specifically for government payments over certain amounts. If your tax payment is substantial (they didn't give me the exact threshold, but mine was around $3,500), they automatically flag it for manual review which adds a few extra days to processing. The good news is that once it cleared, everything went perfectly and I got confirmation from both TurboTax and the IRS that the payment was received on time. Marcus customer service was actually really helpful when I called - they could see the payment in their system and assured me it would go through, just needed the extra verification time. My advice would be to not panic if you see it sitting in "pending" status for longer than usual. But definitely keep an eye on it and don't hesitate to call Marcus if it's been more than a week with no movement.

Just a tip - if your husband's ESPP is a qualified plan, there are special holding period rules that affect taxation. If he held the shares for at least 1 year from purchase AND 2 years from the offering date, any discount might qualify for better tax treatment.

I went through this exact same situation last year with my ESPP shares! The "non covered security" designation was so confusing at first. Here's what I learned that might help: Your husband will need to contact his company's stock plan administrator (usually listed on the 1099-B or his employee benefits portal) to get the original purchase details. They should be able to provide a statement showing the purchase date, number of shares bought, purchase price per share, and the fair market value on that date. For the cost basis calculation, it's typically the actual amount paid for the shares (the discounted price). So if he bought shares at a 15% discount, his cost basis would be that discounted purchase price multiplied by the number of shares. One thing to watch out for - depending on how long he held the shares, part of the discount might need to be reported as ordinary income on your tax return, separate from the capital gains/loss calculation. TurboTax Premier does handle this well, but make sure you have all the purchase documentation first. The good news is once you gather the paperwork, it's actually straightforward to enter into tax software. The hardest part is just getting the original purchase information from the company!