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Top 5 AI-Powered Tax Tools for Self-Employed Pros

July 03, 2025•2 min read

By Joe DiChiara, CPA | CPAi Business Builders

Ready to stop overpaying the IRS and start keeping more of what you earn? These tools are how smart solopreneurs do it—with less stress and zero spreadsheets.

🔧 1. Keeper Tax

What it does: Automatically scans your bank and credit card transactions to detect deductible expenses in real-time.

✅ Real-time write-off tracking
✅ Monthly tax reports
✅ IRS audit support included

Perfect For: Freelancers, consultants, coaches who hate paperwork.
👉 https://www.keepertax.com

💰 2. Gusto

What it does: Manages payroll for S Corps (and LLCs too). Helps you pay yourself a salary and avoid self-employment tax overload.

✅ Automates tax filings
✅ Direct deposit for owner’s salary
✅ Employee and contractor support

Perfect For: Anyone using or planning an S Corp election.
👉 https://www.gusto.com

🚗 3. MileIQ

What it does: Tracks your mileage automatically using GPS. Classify each trip with a swipe.

✅ Maximize your vehicle deduction
✅ IRS-compliant logs
✅ Auto-classify frequent trips

Perfect For: Real estate agents, mobile service providers, side hustlers.
👉 https://www.mileiq.com

📊 4. QuickBooks Online + Live Bookkeeping AI Plugins

What it does: Real-time income/expense tracking, invoicing, bank reconciliation, and with the right AI plugins—automated categorization and forecasting.

✅ Integrates with most banks and apps
✅ Live bookkeeping + AI classification
✅ Detailed tax reporting

Perfect For: Growth-minded entrepreneurs who want scalability.
👉 https://quickbooks.intuit.com

🤖 5. ChatGPT (Yes, seriously!)

What it does: Ask ChatGPT to explain tax strategies, write off rules, or simulate S Corp savings. It’s like having a CPA in your pocket—without the hourly rate.

✅ Research tool for deductions
✅ Write-off ideas by category
✅ Business planning assistant

Perfect For: DIYers and solopreneurs who want clarity fast.
👉 https://chat.openai.com

🔐 Bonus: Want My Full Tax Optimization System?

📅 Book a free strategy session with me
We'll plug these tools into a step-by-step system that reduces taxes, increases peace of mind, and automates the crap out of your back office.

💥 This is the new way to do business.

Ditch the paper. Slash your taxes. Use AI.

You’ve got this. And I’ve got your back.

— Joe DiChiara, CPA

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Joe DiChiara

Joe DiChiara, CPA/CAIS With over 40 years of experience as a Certified Public Accountant, Joe DiChiara specializes in helping small business owners succeed. As the founder of Bedrock Business Builders Corp, Joe provides a wide range of services, including tax resolution, tax preparation, payroll, entity setup, and CFO solutions. His expertise extends to solving complex tax problems and offering AI-powered marketing solutions through MarketingMaverick.ai, a division that empowers businesses to achieve a year's worth of marketing results in just 30 days. Joe has worked with thousands of businesses, focusing on self-employed individuals and companies with 0-50 employees in metropolitan areas. Known for his innovative approach and commitment to client success, Joe combines traditional accounting knowledge with modern tools to deliver transformative results.

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