He Didn’t File for Years—Then Owed Six Figures: What Self-Employed Pros Can Do Next

By / Legal Tips

He Didn’t File for Years—Then Owed Six Figures: What Self-Employed Pros Can Do Next You’re 1099, busy, and the years blurred. Now you’ve finally filed—and the balance is jaw-dropping. Take a breath. You have options with the IRS and the Massachusetts DOR. Here’s the practical path forward. First: Stabilize (Today–This Week) Open every notice. Deadlines …

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Common Legal Mistakes Nonprofits Make (And How Non Profit Lawyers Can Help)

By / Legal Tips

Common Legal Mistakes Nonprofits Make (And How Non Profit Lawyers Can Help) Running a nonprofit sounds noble, right? You have a mission, you have supporters, and you want to make a difference. But even the most well-intentioned organizations can land in serious legal trouble if they overlook key compliance steps. Could your nonprofit face fines, …

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Harvard in the News: Could Your Nonprofit Face the Same Risk?

By / Legal Tips

Harvard in the News: Could Your Nonprofit Face the Same Risk? Harvard is making headlines, and not for its academics. The university is now facing questions about whether it still qualifies as a nonprofit. Why? Because there’s growing concern it’s stepped outside the boundaries of its tax-exempt purpose.If Harvard can land in hot water, your …

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Can You Deduct Gambling Losses on Your Taxes? Here’s What the IRS—and Your State—Wants to See

By / Tax Propaganda

Can You Deduct Gambling Losses on Your Taxes? Here’s What the IRS—and Your State—Wants to See You hit the jackpot—or maybe you didn’t. Either way, if gambling played a role in your finances last year, the IRS wants a look. Yes, gambling winnings are taxable. Every dollar. But what about your losses? Can you deduct …

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Are Self-Employed Individuals’ Chances of Being Audited Higher?

By / Tax Propaganda

Are Self-Employed Individuals’ Chances of Being Audited Higher? The Fear of an Audit Nobody wants to receive that dreaded letter from the IRS. If you’re self-employed, you may have heard that your chances of being audited are higher. Is that true? Unfortunately, yes. The IRS tends to scrutinize self-employed individuals more closely. But why? And …

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Today’s Tax Propaganda: Suspension of Driver’s Licenses!

By / Tax Propaganda

Today’s Tax Propaganda: Suspension and Driver’s Licenses! “Did you know that the Massachusetts Department of Revenue suspends your driver’s license if you fail to file your tax returns or fail to pay your taxes? Then the state suspends your car registration – including the cars registered to you that your family members drive!” Don’t wait …

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