Thanks for this advice! I hadn't thought about keeping specific documentation of the tax year designation. Will Fidelity automatically generate a receipt showing the 2020 contribution, or should I request something special when I make the contribution?

When you make the contribution online, you'll receive a confirmation that should clearly indicate the tax year. Print this or save a PDF of it. Additionally, I'd recommend taking a screenshot of the contribution page where you select "2020" as the tax year. Fidelity will also generate a Form 5498-SA in May that officially documents your HSA contributions by tax year. This form is sent to both you and the IRS. While you don't need to include it with your tax return, definitely keep it with your tax records. If you want to be extra careful, you can also call Fidelity after making the contribution to confirm it was properly coded for 2020, and make a note of the date, time, and representative's name from that call.

Generally for online transactions, midnight in your time zone on the deadline day is acceptable. However, different HSA providers might have different cutoff times for processing transactions, especially if they require manual verification or processing. To be safe, I'd recommend making the contribution at least 2-3 business days before the deadline. I made this mistake last year trying to fund my HSA on April 15th at 9pm, and while my provider (not Fidelity) accepted it, they initially coded it for the wrong tax year and it was a hassle to get fixed.

Is there a minimum amount for business expenses to be worth tracking? Like, do I need to save receipts for $5 purchases or only bigger things?

There's no minimum threshold - technically even small expenses are deductible if they're legitimate business costs. I personally track everything because those small purchases add up quickly. A $5 expense every workday is over $1,200 annually! I recommend using a receipt-scanning app that links to your accounting software. I snap a pic of every receipt immediately, categorize it, and then I don't have to worry about keeping paper copies. The IRS accepts digital records as long as they contain all the relevant information. Better to track too much than miss deductions!

I went through an audit last year for my LLC. They specifically looked at my home office deduction. As long as you have good documentation (photos of the space, a diagram showing square footage, and records of your total rent/mortgage), you should be fine. Just make sure that space is EXCLUSIVELY for business. That's what they look for.

Thanks for the pricing insight. I was definitely worried about charging too much as a newcomer, but what you're saying about the perception of quality makes sense. Would you recommend gradually increasing prices as I gain more clients, or should I start higher right away?

I'd recommend starting closer to market rates right from the beginning. You can always offer an introductory discount to your first clients if you're concerned about the price, but explicitly frame it as a discount so they know the real value. Don't fall into the trap of having to raise prices significantly for existing clients later - that's much harder to do. Better to start near where you want to be. Focus your marketing on the specialized value you bring to Hispanic truckers - bilingual service, understanding their specific business challenges, and knowledge of all the deductions they're entitled to. Many will pay more for someone who truly understands their situation.

This is great advice. I do something similar but I also bring a one-page handout that shows common deductions for their industry with typical dollar amounts. Truckers can claim per diem, maintenance, phone costs, etc. Having something physical they can take with them helps too.

This is super helpful! Do you have any specific questions we should ask when interviewing a new CPA to determine if they're more of a #2 or #3?

Ask them: "Do you provide mid-year tax planning meetings?" and "Can you describe your process for identifying tax saving opportunities throughout the year, not just at filing time?" A good #3 tax planner will have clear answers about their proactive approach. Also ask: "What tax planning strategies have you implemented with clients in situations similar to mine?" They should be able to give specific examples without hesitation. Finally, inquire about their fee structure for planning services versus compliance work. True tax planners typically have separate engagement options for planning versus just tax preparation.

This matches my experience too. I switched from a solo CPA to a mid-size firm last year and the difference is night and day. They caught several things my previous guy missed including HSA contribution strategies.

How do you calculate the percentage for phone bills? I use my phone for personal stuff too, not just DoorDash.

I estimate what percentage of my phone usage is for gig work versus personal use. For me, it's about 60% for work since I'm constantly using it for the apps, navigation, contacting customers, etc. So if my monthly phone bill is $100, I deduct $60 as a business expense each month. Just make sure you can reasonably justify whatever percentage you claim if you're ever asked about it. Some people I know keep track of their screen time in different apps to calculate a more precise percentage, but that seemed too tedious for me.

Form 4852 is specifically a substitute for W-2 forms, not 1099s. For independent contractor income without a 1099, you just report it directly on Schedule C. There's no substitute form needed for missing 1099s - you just need to report the correct amount of income.