Keep more of what you earn. Keeper is the year-round tax platform for freelancers, contractors & solopreneurs to uncover tax savings & file with confidence.
San Francisco, CA
Joined November 2018
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Talking business for 5 minutes does not magically turn your $300 dinner into a tax write-off 💀
So when can you actually deduct a business meal?
Scott Levy, CPA and Keeper Tax Expert with 15+ years of experience, breaks down the IRS rules.
For most self-employed people, freelancers, and 1099 workers:
✅ A qualifying meal with a current or potential client, customer, consultant, or similar business contact may be deductible
✅ The expense needs to be ordinary and necessary for your business
✅ You or an employee generally need to be present
✅ The meal cannot be lavish or extravagant under the circumstances
✅ Qualifying business meals are generally only 50% deductible, not 100%
✅ Keep records of what you spent and the business purpose
And NO, eating lunch by yourself while you work does not automatically make it a business expense 👀
Original clip: #therealtaxguy
Is it fair to ask your partner to make you work optional?
Tell us below because Couples Therapy's Michal and Michael, went to war over that exact question and never landed on an answer.
So we had Keeper tax expert Scott Levy, a CPA who's spent 15+ years filing thousands of tax returns and working 1-on-1 with couples just like this do the math on what it takes to make your partner work optional.
Original clip: #CouplesTherapy, @Showtime
Here’s the fine print on a few:
🏢 An S-corp splits your income into salary and distributions, and distributions skip the 15.3% self-employment tax. At $150K profit with an $80K salary, that’s roughly $9K a year saved. Under about $80K in profit, payroll costs and an extra return eat the savings.
👧 Hiring your kids is real. Sole proprietors can pay their kids under 18 for real work, those wages skip Social Security and Medicare tax, and the first ~$16K is federal income tax free. Keep records. The IRS loves flagging this one.
🏠 The Augusta rule lets your business rent your home for up to 14 days a year. The business deducts the rent, and you pay zero tax on the income. But it needs an S-corp or partnership paying you fair market rent, with real documentation. Without one, it basically doesn’t work.
📄 An LLC by itself changes nothing about your taxes. It’s liability protection, not a tax strategy.
🚙 A car is only deductible for its business-use share, and the big first-year write-offs need 50%+ business use, a 6,000 lb vehicle, and a mileage log. Buying one just for the deduction still means spending a dollar to save around 30 cents.
⚠️ You don’t have to guess which of these apply to you. Keeper’s free tax analyzer looks at your actual income and work, then shows you which strategies fit your specific situation.
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🔗 Use Keeper’s free tax analyzer tool to uncover tax saving moves that actually apply to you: tinyurl.com/45vuuf2y
Educational only, not personal tax advice.
Which tax moves are actually worth it?
We ranked 12 of the tax strategies self-employed people get pitched, by what they really save vs. what they cost.
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1 in 3 Americans now side hustle, and it’s not for fun money. It’s to afford cost of living expenses
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Now here’s the part nobody explains to new side hustlers:
🧾 Side hustle income is taxed differently than a paycheck. No employer withholds anything, and you owe regular income tax PLUS self-employment tax (15.3%, which covers Social Security and Medicare) on your profit.
🧾 That kicks in fast: just $400 of net earnings in a year means you owe self-employment tax.
🧾 Write-offs are how you fight back. They’re work expenses the IRS lets you subtract from your income before your taxes are calculated. Lower taxable profit means lower income tax AND lower self-employment tax.
🧾 They’re not coupons. A $100 write-off doesn’t take $100 off your bill. It shrinks the income your bill is based on, and that adds up fast when you claim everything you’re entitled to.
🧾 Every job has its own list. Delivery drivers can claim miles, a hot bag, part of a phone bill. Resellers claim supplies and shipping. If you use it to earn, there’s a good chance some of it counts.
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That's EXACTLY why we built Keeper.
It scans your bank for hundreds of eligible write-offs based on your specific 1099 job.
Try it for free to see how much you could save: tinyurl.com/2dcsh3b2
Educational only, not personal tax advice.
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Every freelancer has fantasized about moving somewhere with no income tax. 9 states actually offer it, but 4 of them have a catch 👀
⏰ Q2 estimated taxes are due June 15.
You might owe if you made 1099, freelance, rental, investment, or other income without enough tax withheld.
Don’t guess and risk an IRS underpayment penalty. Check if you owe and how much with Keeper’s free quarterly tax calculator: shorturl.at/RWME0
Keeper retweeted
The IRS has officially started accepting returns this year, and I’m seeing #TaxStrike2026 trending.
And honestly, I get it. I talk to frustrated taxpayers daily. I understand the anger. The system is broken. But honestly, this advice is dangerous.
Here's why the math behind it could bankrupt you 👇
People are saying:
1. Don't pay taxes.
2. Stick the money in a HYSA earning 4.5% APY.
3. Pay the IRS fine later with the interest earned.
But the IRS Failure-to-File penalty is 5% PER MONTH.
You’re chasing a 4% annual return while taking a 60% annualized hit from the Feds. 🧵 [1/3]
Stop guessing. Start saving. Taxes confusing?
🎉 Introducing Tax Pro Consultations by Keeper.
✅ Keeper now analyzes your specific tax complexity
✅ Matches you with an expert based on your situation
✅ Lets you talk 1:1 to discuss personalized strategies
🔗 Link in bio!
🎉 Tax filing is officially open in Keeper!
How to get a head start:
1. Upload your tax forms
2. Uncover missed tax savings
3. Ask questions, get expert-backed answers
4. File with total confidence year after year
Link in bio.
3. Remember key dates to avoid IRS penalties 🗓️
Jan 26, 2026: IRS starts accepting/processing returns
Apr 15, 2026: deadline to file + pay (or file an extension)
Oct 15, 2026: final deadline if you extended