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Plus, the 1099 myth, a contract you can send today, and Iron Man’s back taxes. ย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โย โ
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Happy Tuesday! Labor Day is a couple weeks out, which feels like the right time to talk about labor โ specifically, the kind you already did and haven’t been paid for.
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Let’s get to it.
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This weekโs lineup:
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๐ป What actually happens when a client stops paying you โ and you never signed anything
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๐ฃ You got a 1099 for your side gig. Congratulations, that’s not a contract.
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โ๏ธ The one-page contract every freelancer should have before the next “quick job”
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๐ฌ Robert Downey Jr. owed the IRS long before he owed anyone an โIron Manโ sequel
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Business & Gigs
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๐ป What actually happens when a client stops paying you โ and you never signed anything
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The Quick & Bristly:ย No signed contract doesn’t mean no rights. Emails, texts, and invoices can function as a contract if they show an agreement on scope and price. In New York City, New York State, and California, hiring parties are legally required to put freelance work over a set dollar threshold in writing โ and if they don’t, that failure works against them, not you. If a client stops paying: document everything, send a formal demand letter, then small claims court, which most states let you use without a lawyer.
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Every freelancer has lived some version of this: the invoice goes out, the client goes quiet, and the read receipt just sits there like evidence of a crime nobody’s investigating. The panic that follows usually comes from one specific thought โ nothing was ever signed, so there’s nothing to stand on. Right? Wrong.
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You probably have a contract and don’t know it. Contract law doesn’t require a signature on letterhead. It requires an offer, an acceptance, and an exchange of value โ and a thread of emails that says “here’s the project, here’s the rate, sounds good” can satisfy all three. Courts look at the full paper trail: your proposal, their reply, the invoice, the delivered work. None of it needs a notary.
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Some states don’t leave it to chance. New York City’s Freelance Isn’t Free Act, and the statewide version that followed it, require any hiring party retaining a freelancer for $800 or more to provide a written contract. Skip it, and the hiring party is the one who broke the law. California’s Freelance Worker Protection Act does the same at a $250 threshold, effective since Jan. 1, 2025. No written agreement in one of these places isn’t a gap in your case. It’s evidence.
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The paper trail is your defense. Gather the scope conversation, any approved changes, your invoice, and delivery confirmation (a sent email, a “looks great, thanks!” text). This is what turns “they didn’t pay me” into a claim someone else has to answer.
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The escalation ladder:
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A direct, firm follow-up referencing the invoice number and due date
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A formal demand letter with an amount owed and a deadline (this alone resolves a lot of these)
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Small claims court, usually without a lawyer, for a filing fee in the double digits or low hundreds
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Freelance work doesn’t come with a W-2’s guardrails. But it’s not the free-for-all it feels like when your client stops responding to your third โwhereโs my moneyโ email.
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ย ๐งฐย TAXSTACHE TOOLKIT
My client stopped paying โฆ now what?
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Type in your state and what you’re owed. Get the exact law protecting you and what your next move should be โ no legal research required.
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PRESENTED BY ALOHI
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The fastest way to make it official
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Emails and texts can hold up in court, but a real signed agreement holds up faster. Sign.Plus lets you send a contract, get it signed from any device, and track exactly when they open it โ no more guessing if they’re ignoring you or just slow. Send your first contract free.
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๐ Sign smarter, get paid faster
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Tax Strategies
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๐ฃ You got a 1099 for your side gig. Congratulations, that’s not a contract.
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The Quick & Bristly: A 1099 is a tax reporting form, not a legal agreement โ it tells the IRS what you were paid, not what you were promised. Starting with 2026 payments, the 1099-NEC/MISC threshold jumps from $600 to $2,000 under the One Big Beautiful Bill Act, and the 1099-K threshold reverts to $20,000 and 200 transactions. None of that changes what you owe โ every dollar of side-gig income is taxable whether or not a form shows up.
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A 1099 shows up and it feels like a small victory โ official paperwork, proof the gig was real. Freelancers treat it like a receipt for the whole relationship: this happened, we’re square. But it only documents one thing. It has nothing to say about everything else that usually goes wrong.
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A 1099 tells the IRS how much you got paid โ nothing about what you were supposed to deliver, when, who owns the work, or what happens if the client wants three rounds of revisions on a project quoted for one. That’s what a contract is for.
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The threshold just moved, and it matters for a different reason. As of payments made after Dec. 31, 2025, clients don’t have to send a 1099-NEC until they’ve paid you $2,000. More of your smaller clients simply won’t send anything. Fewer forms, same amount of income to report โ the tax obligation never had a form-based exception.
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No 1099 is not a green light to skip a contract. If anything, it’s the opposite: a client big enough to hit the new threshold is a client worth having real terms with in writing โ not because the IRS requires it, but because you’re the one with the most to lose.
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Treat the 1099 as what it is: a receipt for the tax authorities. The contract is what protects the job.
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ย ๐งฐย TAXSTACHE TOOLKIT
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Do I actually need this in writing?
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Two answers in five seconds: does this client legally owe you a contract, and will they owe you a 1099. Just plug in the numbers.
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The one office machine you can finally ditch
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The IRS still runs on fax for more than you’d think: EIN applications via Form SS-4, responses to a CP2000 notice, identity verification letters with a deadline attached. Fax.Plus sends and receives faxes online โ no machine, no landline โ straight from your computer, phone, or email. HIPAA and IRS-friendly, works from anywhere.
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๐ Fax your forms, skip the fax machine
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Every Thursday, we go to work.
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The TaxStache Business Edition is built for owners and operators. Quick hits on entity structure, quarterly deadlines, deduction strategy and the IRS rule changes that actually affect your bottom line. Plus a weekly download you can put to use the same afternoon.
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If you run a business (or you’re building one), Thursday is definitely your day.
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Would you like to receive our Thursday Business Edition?
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Wacky Tax Tales
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๐ฌ Robert Downey Jr. owed the IRS long before he owed anyone an โIron Manโ sequel
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Image by Andres M.
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The Quick and Bristly: Long before he was Tony Stark, Robert Downey Jr. spent the 1980s and ’90s cycling through addiction, multiple arrests, and jail time โ and by multiple accounts from that era, fell more than $2 million behind on state and federal income taxes along the way. He paid it off once his career and finances stabilized. A tax bill doesn’t go away because your life is in chaos. It just waits, with interest, for the day you’re ready to deal with it.
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Long before Marvel rebuilt his career, Robert Downey Jr. racked up two decades of mugshots, court dates, and rehab stints that tabloids covered breathlessly. What they mostly skipped were the other bills piling up in the background โ the ones from the IRS, which doesn’t care about a redemption arc until it’s actually been paid.
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Downey’s legal troubles are well documented: multiple drug arrests, a 1996 weapons charge, and stretches of incarceration covered by real news outlets at the time. The roughly $2 million tax debt is corroborated by a USA Today investigation that reviewed federal and state tax lien filings directly.
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The story still holds a real lesson. Back taxes don’t pause for a crisis. Whatever was happening in Downey’s life during those years โ and by his own account, a lot was โ the balance kept accruing in the background, waiting for a version of him with the stability to deal with it.
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None of that requires a comeback story to fix. A tax bill you can’t pay right now doesn’t disappear if you ignore it โ it grows, with interest and penalties stacking on top. The IRS has payment plans, offers in compromise, and hardship provisions for exactly this situation, and every one of them works better the earlier you engage.
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Everyone remembers the comeback โ fewer people notice the years of quietly paying down a tax bill it took to get there, which is the part actually worth learning from.
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The quick (and slightly prickly) stories we didnโt have time to get to:
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๐ Two taxpayers tried to block the IRS from issuing “lock-in letters” that force employers to max out their paycheck withholding โ a Texas judge said no, partly because neither of them had actually filed a tax return since 2022.
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๐ต โNo Tax on Tipsโ is a deduction, not a magic exemption โ tips still count as income, still get taxed for Social Security and Medicare, and only the first $25,000 is federally deductible.
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๐ฎย An IRS supervisor got fired for underreporting her own taxes and claiming her goddaughter as a dependent she wasn’t entitled to โ a federal appeals court just upheld it. Even the tax police don’t get a pass.
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๐ You wrote the contract. Now actually send it. Sign.Plus lets you fire off that one-pager for a signature before “quick job” turns into “unpaid job.” No printer, no scanner, no chasing someone down at a coffee shop. Just upload, send, done โ and it’s legally binding under ESIGN and UETA. Send your first contract free. (sponsored).
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If you made it this far, youโre our kind of nerd. Hit reply and tell us which story you want us to dive deeper into next week.
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