Keeper AI Tax Assistant for Individual Freelancers
Automate 1099 deductions and eliminate tax bill surprises with a tax-law trained LLM assistant.
Deep Context
Keeper AI is a specialized tax filing and expense tracking platform built for the 1099 economy.
Executive Summary
It utilizes a tax-law trained LLM to automatically scan financial transactions, identify IRS-compliant deductions, and provide real-time tax liability forecasting for self-employed individuals.
Perfect For
- Independent contractors (1099-NEC)
- Solo freelancers and creative professionals
- Gig economy workers (Uber, DoorDash, Upwork)
- Consultants with high transaction volumes
Not Recommended For
- W-2 exclusive employees
- C-Corporations with complex payroll
- International entities without US tax nexus
The AI Differentiation:
The Tax-Law Oracle Engine
Unlike generic OCR tools, Keeper's LLM is trained on the Internal Revenue Code and Treasury Regulations. It autonomously maps bank transaction metadata to specific Schedule C categories, predicting tax bills by calculating effective self-employment tax rates against real-time income streams.
Enterprise-Grade Features
Automated Expense Discovery
Scans linked bank accounts to instantly flag deductible business expenses specific to freelance niches.
Real-Time Tax Liability Tracker
Provides a live estimate of federal and state taxes owed, including self-employment tax, to prevent quarterly penalties.
Smart 1040 Filing
Integrated tax filing service that exports found deductions directly into federal and state returns.
Audit Protection Logic
AI-driven classification documentation that provides a defensive trail for every claimed business expense.
Personal/Business Splitter
Intelligently identifies 'mixed-use' expenses like cell phone bills or home office utilities for partial deduction.
Pricing & Logistics
Professional Integrity
Core Strengths
- Industry-leading deduction accuracy for 1099s
- Eliminates manual bookkeeping and receipt hoarding
- Seamless mobile app experience
Known Constraints
- Requires linking bank accounts for full utility
- Annual tax filing may require a separate fee depending on tier
Industry Alternatives
QuickBooks Solopreneur
Offers integrated invoicing and broader accounting features.
TurboTax Self-Employed
Market-leading brand recognition and robust filing-only support.
FreshBooks
Stronger emphasis on client project management and time tracking.
Expert Verdict
The premier choice for 1099 contractors who prioritize automated savings over manual ledger entry.