Do you need receipts for all of these? I did some freelance work last year but was terrible about keeping records. Can I still claim some of these deductions?

You should ideally have documentation for all business expenses, but the level of documentation varies. For things like home office, you need to know the square footage. For mileage, you should have a log of business trips. For expenses like internet and phone, you can calculate the business percentage based on reasonable usage. If you don't have exact receipts but have bank or credit card statements showing the purchases, that can work too. The key is being able to show the expense was real and business-related if you ever get audited. For this year going forward, I recommend using a free app to track expenses or even just a simple spreadsheet. It makes tax time so much easier!

I used Direct Pay last year. When you go through the steps, you select "Form 1040" and then "Tax Return" or "Balance Due" as the payment type (I used Balance Due). Then select the right tax year. It was actually easier than I expected. Just make sure you keep the confirmation number they give you after the payment processes. I also took a screenshot of the confirmation page just to be safe.

Is this still true with all the recent changes to federal cannabis policy? I thought things were changing with banking and taxes.

Yes, it's absolutely still true. While there have been some banking improvements with the SAFE Banking provisions, Section 280E is still very much in effect and will remain so until cannabis is rescheduled or descheduled at the federal level. The recent policy changes have mainly affected banking access and research, but the tax code restrictions remain unchanged. Any legitimate PE firm in the cannabis space should be building their financial models with 280E limitations factored in, resulting in effective tax rates that can reach 50-70% depending on the operation's structure. Always ask to see their tax assumptions when reviewing projected returns.

Thanks for bringing this up - honestly I haven't done as much due diligence as I probably should. They did provide an investment memorandum but I haven't verified SEC registration or the actual farm ownership. Do you have suggestions for what specific documents I should be requesting or how to verify their legitimacy?

Absolutely. Request their Form D filing with the SEC (all private offerings should have this), check the backgrounds of all principals through FINRA BrokerCheck, and get proof of the actual cannabis licenses they hold or have applied for. Also ask for references from current investors, and ideally visit the actual operation if possible. Request their detailed tax strategy document specifically addressing 280E issues - legitimate operators will have this prepared. Finally, have an attorney experienced in cannabis review all documents before transferring any money. The extra $1-2k in legal fees could save you from a total loss on your investment.

Do you know if they offer any sort of discount or special features for seasonal businesses? Since tax prep has that huge Jan-April rush and then slower periods.

They don't have specific seasonal business features that I know of. But their transaction limits are fairly generous which handles the busy season well. During slower months, you can easily maintain the minimum balance to avoid fees since you're not drawing as much from the account. The mobile app is also really good for depositing client checks which saves tons of time during the busy season when you can't step away to visit a branch.

Square's great but their transaction fees add up. 2.9% + $0.30 per transaction means you're losing like $3-4 on each $100 payment. Better to encourage direct bank transfers or checks.

Thanks for mentioning this! I didn't even think to check if our employers offer early online access to W-2s. I'll definitely look into that right away. Is there any difference between the electronic version and the paper one that gets mailed out?

The electronic and paper W-2s contain exactly the same information - they're just delivered differently. The electronic version is official and can be used to file your taxes just like the paper copy. The advantage is you typically get access to it 1-2 weeks earlier than waiting for mail delivery. Just log into your company's HR portal or payroll system and look for a tax documents section. Some employers require you to specifically opt-in for electronic W-2 delivery, so check that setting too. If you can't find it, ask your HR department - they'll point you in the right direction.

Yep! Same with my company's fitness subsidy. They reimburse my gym membership but it counts as taxable income that only appears on W-2. Also, if you have company stock or RSUs that vested, those calculations can be super complex and often don't appear accurately on regular pay stubs.

23 Do you use any specific apps to track expenses? I've been just keeping physical receipts in a shoebox and I know there's got to be a better way lol.

19 I use QuickBooks Self-Employed and it's been a lifesaver. You can link your business accounts and credit cards, then just swipe right or left to categorize transactions as business or personal. It also has a mileage tracker that runs in the background on your phone. Another good option is Expensify if you don't need full accounting software. Wave is a free alternative that a lot of people like too. Anything is better than the shoebox method! I missed so many deductions my first year because receipts got lost or I forgot what expenses were for.

8 Do you know what the threshold is for when you need to make quarterly payments? Like is there a minimum amount you need to earn?