Your Smart Tax Assistant

The deductions you keep missing — found, sorted, filing-ready.

A smart tax co-pilot that captures everything you earn and spend, explains what each deduction means, and hands you a clean packet — for your CPA or to file yourself.

14 days of Pro — free. Cancel anytime.

$3,000–$5,000 in missed deductions a year for the self-employed* Bank-level 256-bit encryption
Read-only bank access
IRS-compliant deduction categories
Receipt OCR built-in
14-day free trial
By the numbers

The deduction gap is real.

IRS audit data tells a consistent story: self-employed income is the least-verified category in the U.S. tax system — and inadequate recordkeeping is the primary driver of the gap.

$539B

In taxes understated on filed returns, per year

The IRS projects a $696 billion gross tax gap for tax year 2022. Underreporting on timely filed returns accounts for $539 billion of that — more than three-quarters — with business income as the primary source.

IRS Tax Gap Projections for Tax Year 2022 (Pub. 5869), released October 2024

55%

Noncompliance rate for sole proprietors

For W-2 wage earners, the IRS estimates roughly 1% noncompliance. For Schedule C proprietorship income — with no employer withholding and no third-party reporting — that figure reaches 55%.

U.S. Dept. of the Treasury, "The Case for a Robust Attack on the Tax Gap" (2021); IRS National Research Program audit data

>50%

Of the individual gap flows from small-business income

About half of the individual income tax gap accrues to proprietorships, partnerships, and S-corps — income sources where there is little or no third-party data for the IRS to verify what was filed.

U.S. Dept. of the Treasury, citing IRS Tax Gap Studies

For a typical self-employed worker, this translates to an estimated $3,000–$5,000 in missed deductions annually — a direct reduction to your tax bill.

Source: 2019 analysis of 1099 tax returns cross-referenced with IRS SOI Nonfarm Sole Proprietorship Statistics

A note from the founder

I'm a firefighter who picked up side income to support my family — a small business and a rental on top of the day job. I never had time for the tax side, so each spring I'd dump a year's paperwork on my CPA, hope for a good return, and move on — with no real understanding, and plenty of missed opportunities.

So I started using AI tools to actually learn the system, built myself an assistant that tracked my expenses and taught me as it went. When friends saw it, they all asked the same thing: could they use it too?

That's how DeductSam was born.

How it works

Three steps. Then we stay out of your way.

Connect in 60 seconds

Securely link your bank and upload receipts. Read-only bank access — Sam never moves money.

Sam reads every transaction

Our AI categorizes each charge, surfaces missed write-offs, and flags receipts that need a photo.

Ready for your CPA or your own return

Export a clean Schedule C or share it straight with your CPA. The self-employed leave an estimated $3,000–$5,000 in deductions unclaimed each year.*

Pricing

Two weeks free. Then less than one missed deduction.

Every signup starts with a full 14-day Pro trial — pick any plan when you subscribe. Cancel from the app in two taps.

Monthly Annual Save up to 27%
Starter
For freelancers & side hustles
$9.99 / month
  • AI expense categorization (Sam)
  • Receipt upload with OCR auto-extraction
  • Tax Health score & analysis
  • Tax Opportunities finder
  • Year-End Packet & Schedule C export
  • 1 business + 1 personal account
  • Sam AI Chat Assistant
  • Payroll & 1099 tracking
  • Income & expense dashboard
  • Manual income tracking
Pro
Multiple businesses or teams
$39.99 / month
  • Everything in Core
  • Unlimited business accounts
  • Unlimited team members and accountants
  • Full P&L dashboard with projections
  • CPA read-only access
  • Square revenue sync (coming soon)

Every signup starts with a full 14-day Pro trial. Add a card to start — cancel anytime before day 14 and pay nothing.

Free to try · Cancel anytime

Stop leaving money with the IRS.

Two weeks free. If Sam doesn't surface deductions you'd have missed, delete the account — you won't pay a cent.

* Results vary based on business type and expenses.