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Crypto tax after 1099-DA: proceeds ≠ basis
Form 1099-DA is expanding what brokers report to you and the IRS. That helps — and it also creates a trap: gross proceeds are not taxable gain, and incomplete basis is still the taxpayer’s problem.
The IRS can match proceeds. Underreported gains are low-hanging enforcement fruit.
What 1099-DA changes: more visibility on dispositions through reporting brokers. What it does not automatically fix: perfect lot-level basis — especially wallets, transfers, and older history that never reconciled.
Practical moves before filing season:
• Reconcile exchange + wallet history now, not in March
• Don’t copy 1099 proceeds onto Schedule D as “gain”
• Track cost basis and holding periods yourself (or with software you actually review)
• Keep transfer logs — “unknown basis” is a filing choice with consequences
1099 compliance still includes classic contractor 1099s too: W-9s before first payment, year-round payee tracking in QBO (or your cloud books), and a December dry run so January isn’t archaeology.
Sophie Master, CPA & IRS Enrolled Agent — sophiecpa.com
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IRS compliance for business owners — without the panic
Most expensive IRS problems aren't exotic. They're late deposits, mismatched 1099s/W-2s, thin substantiation, and estimated taxes that never got updated after a good quarter.
What the IRS matches well:
• W-2 and 1099 totals vs what you reported
• Payroll deposits vs Form 941
• Broker / digital-asset gross proceeds
• Outside data that contradicts your return
If books say one thing and third-party forms say another, assume they'll notice. "Mostly ties" is not a strategy.
Practical rhythm that actually helps:
• Refresh estimates after Q2/Q3 when the year is ahead of plan
• Collect W-9s before the first payment — January contractor archaeology breeds penalties
• Never treat withheld payroll taxes as operating cash (trust-fund rules = personal exposure)
• Capture receipts the day of the expense
• When a notice arrives: read the year, form, deadline — respond with docs, don't ghost it
Monthly close. Quarterly estimate check. December 1099 dry run. Document retention that survives staff turnover.
I'm Sophie Master, CPA & IRS Enrolled Agent. More at sophiecpa.com
Bookkeeping Ledger Cleanup (Before & After)
This project demonstrates how I approach cleaning up disorganized financial records. Starting from a "before" dataset with inconsistent date formats, vague or typo'd transaction descriptions, and no categorization — a common state for small business books — I rebuilt it into a professional, audit-ready ledger. Each transaction was standardized, correctly categorized (e.g., Office Supplies, Sales Revenue, Rent Expense), and linked to a formula-driven running balance that recalculates automatically as entries are added. This is the kind of cleanup work I'd do for a client whose books have fallen behind or were kept inconsistently, turning scattered data into something an accountant, tax preparer, or business owner can actually rely on.
"Zahid has successfully delivered and deployed HCM within our company."
That's from the client review that landed on my profile this week, for OneHub — the payroll and people-operations platform I built for TechFoundry. Monthly payroll with fiscal-year tax withholding, payslips and tax certificates on demand, expense reports read line by line by Claude, and one reporting layer so the dashboard, the payslip and the certificate always agree.
The word I care about in that review is "deployed". Delivered means the code works. Deployed means payroll runs on it every month, people are paid the right amount, and nobody has to call me.
The thing I'd do differently: the tax rules started out hard-coded. Fine for one country, one fiscal year — until it wasn't. We later pulled them out into a rules engine so the same payroll runs across countries without touching the code. Next time that's day one, not a refactor.
It's also a Contra-verified project — the work was paid through Contra, so the review and the case study are tied to the same engagement. Case study: https://contra.com/p/Y3EgrEUc-payroll-and-people-operations-platform
