What Estimated Tax Payments Are and Why the IRS Requires Them
If you earn income that does not have taxes automatically withheld, you have probably heard of estimated tax payments. These payments are not optional, and failing to understand how they work can lead to penalties even if you pay your full tax bill by April. Estimated payments are the IRS’s way of collecting taxes throughout […]
Chicago Lease Tax Explained and What Your Business Needs to Know
If your business leases equipment, furniture, or software that is used in the City of Chicago, there is a local tax you need to be aware of, and as of 2025, it just became more expensive. The Chicago Personal Property Lease Transaction Tax increased to 11 percent starting January 1, 2025. Many businesses are unaware […]
Illinois Use Tax Explained and When You Owe It
If you live in Illinois and buy items online or from out of state sellers, you may owe a tax you have never heard of: Illinois Use Tax. It is not new, it is not optional, and ignoring it, even unintentionally, can put both individuals and businesses at risk. Illinois Use Tax is one of […]
Tokenized Stocks and Taxes: What Every Investor Needs to Know
A New Kind of Investment. A New Kind of Tax Headache. It’s 11:47 p.m. on a Tuesday and you just bought a fractional share of Tesla—on a decentralized crypto exchange. You didn’t use a brokerage, didn’t sign a W-9, and you’re pretty sure there’s no 1099-B coming in the mail. Congratulations. You just bought a […]