Stop Overpaying the IRS. Start Building Wealth.
The first AI-powered tax strategist for small business owners and freelancers. We find the deductions your accountant misses—year-round, not just at tax time.
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What Is Taxpert Therapy?
Taxpert Therapy is a digital-first tax strategy platform designed for business owners, freelancers, and high-earning individuals who want clarity, confidence, and year-round tax savings—not just at filing time.
We provide:
  • 24/7 AI Tax Monitoring, Strategy, and Sleep
  • Personalized deduction and strategy recommendations
  • Optional CPA review for peace of mind
  • Real-time guidance as your financial situation evolves
Our Goal
Remove tax complexity and help people keep more of what they earn—compliantly, confidently, and proactively.
The System Is Rigged Against Entrepreneurs.
You’re likely overpaying by thousands every year. Why? Because the tax code is complex, traditional CPAs are reactive, and real strategy is usually locked behind a $5,000/year retainer.
Money Left on the Table
Unclaimed deductions are lost profit
The "Tax Time" Trap
Your CPA talks to you once a year—when it’s too late to save you money
Limited DIY Tools
DIY software only helps with filing, not strategic planning
Inaccessible Strategy
Real tax strategy is locked away unless you make $300K+
Taxpert Therapy solves this. We democratize expert tax strategy, making it accessible and affordable for every entrepreneur.
Fortune 500 Tax Strategy. Freelancer Price Tag
Judgment-Free Zone
No confusing jargon, no tax code mysteries, and zero judgment. We fix your messy finances with patience and clarity.
Proactive, Not Reactive
We tell you what to do before the year ends, so you actually save money.
Bank-Level Security
Your financial data is protected by 256-bit encryption.
Fast
AI-powered intelligence in minutes—not weeks. Get answers when you need them, not when tax season arrives.
How the Platform Works
01
Connect Your Data
Securely connect banking, payroll, or QuickBooks. Our AI analyzes patterns and opportunities instantly with bank-level encryption.
02
AI Finds Your Money
Our system instantly analyzes your spending to flag missed deductions and recommend entity structures (like S-Corp) that save you thousands.
03
Confirm with a Pro (Optional)
Want a human review? Our partner CPAs validate your strategy before you implement and/or file, giving you complete confidence.
Key Product Features
AI-Powered Tax Engine
Advanced algorithms analyze your finances to identify savings opportunities traditional methods miss.
Automated Deduction Finder
Never miss a write-off again. Our system scans every transaction for potential deductions.
Real-Time Insights
Get updated recommendations as your finances change throughout the year—stay proactive—navigate new IRC changes.
Tax Structure Analysis
Should you be an LLC, S-Corp, or C-Corp? We analyze and recommend the best structure.
Optional CPA Review
Licensed CPAs available to review and validate your strategy whenever you need human expertise.
Bank-Level Security
256-bit encryption and full data control. Your financial information is always protected and private.
Who It's Built For
Business Owners
Spot missed deductions, plan ahead strategically, and optimize your entity structure—without the $3K+ CPA bill. Get expert guidance at a price that makes sense.
Side Hustlers & Freelancers
Know exactly what you can write off, how much to set aside for taxes, and when to level up to an LLC. Turn your side hustle into smart savings.
High-Earning W-2 Employees
Use backdoor Roths, HSAs, and other advanced strategies to keep more of your hard-earned income. Maximize benefits most employees overlook.

Why Taxpert Therapy Exists
We believe that expert tax strategy should not be a luxury reserved for large corporations and the well-connected - it should be accessible to anyone who works hard and earns well. Every entrepreneur deserves the tools to succeed.
Meet the Founder
David Gillilan — Founder & CEO
Entrepreneurship runs deep in David’s life.
When his father—a U.S. Air Force officer and constant side-hustler—passed away at just 37, David witnessed the sudden loss of financial stability his immigrant mother faced. Through sheer grit, she rebuilt her barbershop business from the ground up, carving a path forward despite overwhelming adversity.
Watching her struggle without access to guidance or support left a lasting impact. David saw firsthand that business owners don’t fail from lack of effort—they suffer from lack of clarity, strategy, and trusted financial insight. That experience shaped his mission: to make expert tax strategy accessible to every hardworking entrepreneur.
20+ years in sales & strategic growth
Executive Education: Northwestern's Kellogg School of Management
Former Director of Business Development at a leading Texas CPA firm
Tax Strategist & Enrolled Agent Candidate

What Users Are Saying

Real Results from Our Founder's Efforts to Help Business Owners The trust and results David delivers through personal advisory work are the foundation of Taxpert Therapy. The platform is built to scale that same expertise—giving every user access to strategic guidance that has helped countless entrepreneurs keep more of what they earn. ⭐⭐⭐⭐⭐ Stephany "Working with David is an absolute game-changer! He explains everything in simple terms and finds deductions you never knew existed. My tax bill dropped significantly." ⭐⭐⭐⭐⭐ Mindy "David took me step-by-step through my financial mess. Very helpful, patient, and knowledgeable. I finally understand my taxes!" ⭐⭐⭐⭐⭐ Hudson "Spot on with communication and extremely well versed. Highly recommend to any business owner looking for real tax strategy."

Your Tax Therapy Starts Here
Stop stressing about the IRS and start keeping more of what you earn.
Taxpert Therapy
Expert tax strategy for the modern entrepreneur.
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Important Disclaimers:
Not Financial, Legal, or Investment Advice Taxpert Therapy, LLC. ("Taxpert Therapy") is a technology platform that provides tax strategy analysis and educational content. Taxpert Therapy is not a law firm, financial planning firm, wealth manager, or registered investment advisor. We do not provide legal advice, investment recommendations, or wealth management services. The information provided by our platform does not constitute a client-lawyer relationship.
Tax Strategy & Estimates All "savings" estimates, deduction flags, and entity structure recommendations are based on the data you provide and general tax principles. These are strictly for planning and educational purposes. Tax laws are subject to change and vary by jurisdiction. Actual tax liability depends on your specific financial situation.
Professional Review While our AI models are trained on current tax codes, Taxpert Therapy recommends that all tax strategies and filings be reviewed by a qualified CPA or Enrolled Agent before submission to the IRS. Services involving the review or filing of tax returns by licensed professionals are provided by independent third-party partners, not directly by Taxpert Therapy's software.
Security Taxpert Therapy utilizes 256-bit encryption and industry-standard security protocols to protect your data. We do not sell your personal data to third parties.
© 2025 Taxpert Therapy, Inc. All rights reserved. Made with ❤️ in Texas.