Tag: small business taxes
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Taxes for Less: A 2026 Founder Playbook
Buy equipment before year-end to lower your taxes. That advice can leave you with a smaller tax bill and too little money to make payroll. I'd rather you keep a useful cash cushion than buy a machine you don't need for a deduction you can't use yet. I treat taxes for less as a runway…
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Business Tax Planning: A Chicago Founder’s Guide
You're probably in one of two spots right now. Either you just made your first real money and you're feeling good, until you remember the IRS and Illinois are about to put their hands out. Or you're still early, maybe pre-product, maybe first customers, and you want to avoid the classic founder mistake of treating…
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