Anomaly CPA
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Anomaly tailors tax & accounting services for businesses & real estate investors to grow.
05/29/2026
Self-employed and paying for health insurance out of pocket? You can deduct 100% of those premiums — for yourself, your spouse, and your dependents.
Most owners either don't know it exists or set it up wrong and lose the benefit entirely.
Here's what makes this one different: it comes off your AGI directly. Not as an itemized deduction. That means you get the benefit even if you take the standard deduction — and it lowers your adjusted gross income before most other calculations hit.
The setup has to follow an exact sequence. The company pays the premium, includes it in your W-2 wages, and you deduct it personally. One step out of order and the deduction disappears.
Layer an HSA on top and you have a second deduction built into the same health plan. Up to $4,150 for individuals or $8,300 for families — also fully deductible.
Two deductions. One health plan. Most owners are only claiming one — or neither.
DM us HEALTH and we'll audit your current setup in minutes.
Cost segregation without REPS status still works.
It just doesn't work the way most high earners need it to.
Here's the problem: if your spouse is making $600K–$800K a year in active income, passive losses from a cost seg study won't touch that.
They sit on your return and wait — indefinitely — until you have passive income to offset them against.
That's not a bad strategy. It's just an incomplete one.
REPS status is what makes those losses active.
And active losses against active income is where the real tax savings happen.
Comment COSTSEG and we'll walk you through whether your situation qualifies.
Most business owners don’t realize this until they’ve already overpaid in taxes for years:
A tax return is not tax strategy.
Traditional accounting is usually reactive:
• send documents
• file returns
• repeat next year
Real tax strategy happens before the year ends.
That means:
• proactive planning
• ongoing communication
• entity structure reviews
• quarterly tax strategy
• business decisions made with taxes in mind
The tax return should just be the report card — not the strategy itself.
Comment “STRATEGY” to learn more.
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Address
22 Boston Wharf Road
Boston, MA
02210
Opening Hours
| Monday | 8am - 5pm |
| Tuesday | 8am - 5pm |
| Wednesday | 8am - 5pm |
| Thursday | 8am - 5pm |
| Friday | 8am - 5pm |
