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Tax strategist Karlton Dennis teams up with School of Hard Knocks at his home in Orange County, California, to break down the essential steps entrepreneurs and high-income earners can take to legally reduce or eliminate their tax burden. Karlton opens up about how he paid $0 in federal income taxes on $7 million in earnings by leveraging real estate investments, paper losses, and smart tax planning. Together, they uncover how proper education and strategy are key to escaping the cycle of overpaying taxes.
The conversation dives deep into practical tactics like using short-term rentals and cost segregation studies to generate paper losses, understanding S-Corp and LLC entity structures, and taking advantage of lesser-known codes like the Augusta Rule. They also explore the difference in mindset between the middle class and the wealthy when it comes to speed and confidence in financial decision-making. Karlton emphasizes that the tax code is a government playbook meant to be used — not feared — if you understand the rules.
Beyond taxes, they touch on core business strategies for scaling income, accessing capital, and using good debt to build wealth. From buying vehicles like G-Wagons for bonus depreciation to reinvesting tax savings into cash-flowing properties, this video is packed with insights on how to grow smarter and keep more of what you earn. Whether you’re just hitting six figures or scaling to eight, this conversation is loaded with real-world tax hacks and entrepreneurial gems you won’t learn in any school.
CHAPTERS:
0:00 Intro
1:34 How Karlton Dennis Makes His Money
4:44 How Karlton Dennis Pays Almost No Income Taxes
7:49 Tax Advice for New Entrepreneurs
10:27 Middle Class vs Wealthy Approaches to Taxes
13:38 Are Luxury Cars Really Depreciating Assets?
16:48 Good Debt vs Bad Debt
21:09 The Best Type of Real Estate to Reduce Taxes
23:28 The Worst Financial Decision I’ve Ever Made
24:55 EXAMPLE: Pay No Taxes on $100k in Income
27:24 Hire Slow, Fire Fast
28:27 Real Estate Tax Hack: The Augusta Rule
30:01 Outro
*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.
#taxplanning #karltondennis #schoolofhardknocks
