When a Nonprofit Loses Tax-Exempt Status: What Happens Next?

When a Nonprofit Loses Tax-Exempt Status: What Happens Next? When a nonprofit loses tax-exempt status, it usually doesn’t start with a dramatic IRS raid. It starts with missed filings. A deadline comes and goes. Then another. Then another. And one day you find out: “The IRS automatically revoked your tax-exempt status… three years ago.” Now …

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Laura A. Brown Featured in Mass Lawyers Weekly on “Bombshell” Tax Court Ruling

Laura A. Brown Featured in Mass Lawyers Weekly on “Bombshell” Tax Court Ruling The Massachusetts Appeals Court recently handed down a significant decision in Welch v. Commissioner of Revenue, ruling that a former resident’s stock sale was subject to Massachusetts taxation. The decision signals a potential expansion of the Department of Revenue’s reach into non-resident …

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501(c)(3) vs. Private Foundation: What’s the Difference?

501(c)(3) vs. Private Foundation: What’s the Difference? If you’re starting or funding a nonprofit, “501(c)(3)” sounds simple… until someone asks: “Are we a public charity or a private foundation?” And suddenly you’re wondering: Does this change our tax rules? Can donors still deduct their gifts the way they expect? Are we accidentally setting ourselves up …

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

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)

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?

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

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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