Why DIY Tax Software Is Costing You Thousands

Buy my book, The Art Of Legal Tax Avoidance ▶

Book a Professional Tax Assessment Call ▶

Cost Segregation Tax Savings Calculator ▶

Download the ShortTerm Rental Rule EBook! ▶

We earn commissions when you shop through the links below.

Get Help Setting up Your LLC, Now ▶

The Hard Truth about DIY Taxes pulls back the curtain on what really happens when individuals and business owners try to handle their taxes on their own. While DIY tax software promises simplicity and savings, the reality is often far more complex—and far more costly. This video explores why so many taxpayers unknowingly leave money on the table, miss critical deductions, or expose themselves to IRS issues, all while thinking they’re doing the “smart” thing.

In this video, tax expert Karlton Dennis explains why DIY taxes can quietly limit your financial growth, especially for entrepreneurs, high earners, and small business owners. He breaks down the mindset mistakes people make when they treat taxes as a once-a-year task instead of a year-round strategy—and why tax planning, not just tax filing, is where real savings are found.

If you’ve ever wondered whether TurboTax, H&R Block, or other DIY tax solutions are truly enough, this article will challenge your assumptions. Without giving everything away, it highlights the risks, missed opportunities, and long-term consequences of going it alone—and why understanding tax strategy, IRS rules, and proactive planning could be the difference between overpaying and keeping more of what you earn.

CHAPTERS:

*Disclaimer: I am not a financial advisor nor am I an attorney. This information is for entertainment purposes only. It is highly recommended that you speak with a tax professional or tax attorney before performing any of the strategies mentioned in this video. Thank you.

#taxfiling #taxstrategy #diytaxes