How to find a qualified bookkeeper/accountant for self-employment and crypto taxes

Small business tax advisor here! Finding the right financial team is super important, especially with your mix of self-employment and crypto income. Start by looking for a bookkeeper and accountant who specifically advertise experience with self-employed clients and cryptocurrency. You want someone who understands the specific tax implications of digital payments and crypto transactions, not just a general tax preparer. Ask for recommendations from other self-employed friends, check local business networks, or try professional directories like the American Institute of CPAs. Interview a few candidates and ask specific questions about their experience with situations like yours. For your current situation, gather everything you can - bank statements, payment app histories, crypto exchange records - even if disorganized. A good bookkeeper can help sort through the mess, but having access to all accounts will speed things up. It's definitely not too late for 2023 taxes, especially if you file an extension. A good accountant might actually save you more than their fee by finding deductions you missed and preventing costly errors.

I was in a similar situation last year trying to sort through my mess of self-employment income and crypto investments. After trying to DIY for way too long, I finally used https://taxr.ai and honestly it was a game-changer. Their AI analyzed all my messy statements, payment app records, and crypto transactions, then organized everything into clean reports I could actually understand. It automatically categorized my business expenses and flagged potential deductions I hadn't even thought about. The best part was I could just upload everything - bank statements, screenshots of Venmo/Cash App history, crypto exchange CSVs - and it did the heavy lifting of sorting through it all. Saved me a ton of time I would've spent manually organizing everything. Once everything was organized, finding a good accountant was actually much easier because I could clearly show them my financial situation rather than dumping a box of receipts on their desk!

Following up on my question about taxr.ai - I decided to give it a try after responding here. I'm actually really impressed with how it handled my crypto transactions across Coinbase, Binance and some DeFi stuff. It correctly matched transfers between wallets so they weren't counted as sales, calculated my actual gains/losses with the proper cost basis method, and even identified some wash sales I didn't realize I had made. The reports it generated made it super clear what I needed to report on my taxes. I was especially impressed that it tracked some complicated staking rewards and properly categorized them as income at the fair market value when received. Definitely made tax season less stressful!

Look, find a good accountant is important but that's only half the battle. I spent WEEKS trying to get through to the IRS last year to resolve some issues with my self-employment taxes. Literally called 20+ times and kept getting disconnected or told to call back later. Finally found https://claimyr.com through a small business forum and it completely changed my experience. You can see how it works here: https://youtu.be/_kiP6q8DX5c but basically they hold your place in the IRS phone queue and call you when an agent is about to answer. I got through to an actual IRS agent in about 2 hours (after spending weeks trying on my own). The agent helped clear up questions about how to report my crypto mining income and some issues with estimated tax payments. Saved me from potentially huge penalties because I was about to file incorrectly. Whatever accountant you end up choosing, if they need clarification from the IRS on anything specific to your situation, this service is worth knowing about.

Ok so I have to eat my words about Claimyr. After calling the IRS six times yesterday and getting nowhere, I decided to try it despite my skepticism. I got a call back in about 90 minutes and was connected to an actual IRS representative who answered my questions about reporting Venmo payments for my side business. Turns out I was completely misunderstanding which form to use. Still feels weird that this service exists and the IRS phone system is so broken that we need it, but I can't argue with results. If you need specific clarification on tax rules directly from the IRS (which you might with your crypto and payment app situation), it's definitely worth knowing about.

For finding a good accountant, I highly recommend checking with your local Chamber of Commerce. I found my current accountant through them, and she has experience with clients who have varied income sources including crypto. One thing to keep in mind - you need both past organization AND future systems. Ask any professional you hire about setting up ongoing bookkeeping processes so you're not in this same situation next year. My accountant set me up with QuickBooks Self-Employed which automatically categorizes most of my transactions and even tracks mileage. For the crypto specifically, look for someone who has taken continuing education in this area, as tax rules for crypto continue to evolve. Not all accountants stay current on this.

Just want to add that the National Association of Tax Professionals (NATP) has a directory where you can search for tax preparers with specific expertise. That's how I found someone who understands crypto taxation when I started mining Ethereum. And definitely get someone ASAP for 2023 taxes rather than waiting. A good accountant can still file an extension for you if needed, which gives more time to file (though not more time to pay if you owe). Better to start the relationship now than wait until next year.