Small Business Tax Savings Podcast

Are you worried a tax strategy could land you in trouble with the IRS? In this episode, Mike Jesowshek sits down with tax attorney Ed Lyon to break down what tax risk actually means. They explain why most business owners do not get in trouble for smart tax planning, where the lin ...  Show more

You’ve hired your first employee… Now what? Hiring your first employee introduces a new layer of tax responsibility, compliance, and systems that many business owners are not prepared for. You are now managing payroll taxes, filings, labor laws, and deadlines that carry real pena ...  Show more

Filing a tax extension feels stressful for many business owners. Missing numbers, unfinished bookkeeping, and uncertainty about the tax bill can make tax season overwhelming. But filing an extension (in many cases) can be the smartest move you can make.A tax extension gives you m ...  Show more

Charitable giving rules are changing in 2026, and many business owners have no idea their tax deductions could quietly shrink.The One Big Beautiful Bill Act introduced new limits, floors, and deduction caps that change how charitable donations work depending on your income level ...  Show more

Imagine breaking even at the casino and still owing taxes.Beginning in 2026, Congress approved a new rule that limits gambling loss deductions to 90%. That means if you win $10,000 and lose $10,000, you could still owe taxes on $1,000 of phantom income.Today, we're breaking down ...  Show more