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

July 03, 20252 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

Top-5-Ai

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.

Top-5-Ai

✅ 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

Top-5-Ai

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.

Top-5-Ai

✅ 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.

Top-5-Ai

✅ 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



Join our CPAi FaceBook group for the Latest and Greatest Ai news, tools and resources for business and personal use! Incorporate Ai NOW or get Eaten by it! https://www.facebook.com/groups/bedrockbusinessbuilders

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.

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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