Posts tagged with "sole proprietor"



Business · June 05, 2026
How to Pay Up to $5,250 of Your Adult Child's College Tuition Through Your Business
Helping your child through college often feels like a personal expense. For some business owners, it may be hiding in the wrong place entirely. A little-known IRS strategy could allow a family business to pay up to $5,250 of an adult child's qualified education expenses tax-free, but only if the structure, employment status, and paperwork are handled correctly. The opportunity is not the benefit itself. It's knowing the rules before an innocent shortcut turns a tax-saving strategy into an expens
Business · May 22, 2026
Before You Load the Car: What Your Business Needs Before You Leave for Summer Vacation
That moment right before vacation feels like relief. The bags are packed, the calendar is cleared, and for a second, you finally exhale. Then a quieter thought slips in: what happens to the business if you cannot come back next week? Not emails. Not meetings. Real authority. Payroll. Contracts. Client work. Most business owners have an out-of-office message, but no actual business incapacity plan. And the difference between those two things only matters when it suddenly matters most.
Business · May 15, 2026
Your Mid-Year Business Check-In: 5 Things to Review Before Summer (and One Deadline You Cannot Miss)
Business feels good right now. Revenue is moving, summer is coming, and the pressure finally feels lighter. That is usually when business owners stop looking closely. Estimated tax deadlines get missed. Contractors start functioning like employees. Old operating agreements no longer match the company you are actually running. Growth can create a dangerous kind of confidence, because problems rarely show up while things are slowing down. They show up after you assumed everything was fine.