276: Why Hiring a Tax Strategist Is The Best Investment You’ll Ever Make with Karlton Dennis
Thu Feb 05 2026
Believe it or not, income taxes can become the biggest expense for entrepreneurs. Yet most people approach tax planning reactively, missing powerful opportunities hiding in plain sight.
Today’s guest helps investors get ahead of the game by treating tax strategy not as compliance, but as one of the most important wealth-building tools available.
Karlton Dennis is one of the leading tax strategists in the country and the founder of Tax Alchemy. Through his work with high-earning entrepreneurs, he helps clients legally reduce taxes, increase cash flow, and reinvest capital intentionally rather than giving it away unnecessarily.
In our conversation, Karlton breaks down why proactive tax planning often delivers higher returns than any investment deal—and how understanding the tax code allows you to keep more money working for you, with more investment opportunities, year after year.
In this episode, you’ll learn:
✅ Why investing in world-class tax strategy can outperform real estate, private equity, and traditional investments.
✅ The most common tax preparation mistakes that cost business owners tens of thousands per year.
✅ Which tax strategies attract IRS scrutiny and how to use the tax code to your advantage without crossing red lines.
Show Notes: LifestyleInvestor.com/276
Tax Strategy Masterclass
If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax
Strategy Session
For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation
The Lifestyle Investor Insider
Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider
Rate & Review
If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.
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Believe it or not, income taxes can become the biggest expense for entrepreneurs. Yet most people approach tax planning reactively, missing powerful opportunities hiding in plain sight. Today’s guest helps investors get ahead of the game by treating tax strategy not as compliance, but as one of the most important wealth-building tools available. Karlton Dennis is one of the leading tax strategists in the country and the founder of Tax Alchemy. Through his work with high-earning entrepreneurs, he helps clients legally reduce taxes, increase cash flow, and reinvest capital intentionally rather than giving it away unnecessarily. In our conversation, Karlton breaks down why proactive tax planning often delivers higher returns than any investment deal—and how understanding the tax code allows you to keep more money working for you, with more investment opportunities, year after year. In this episode, you’ll learn: ✅ Why investing in world-class tax strategy can outperform real estate, private equity, and traditional investments. ✅ The most common tax preparation mistakes that cost business owners tens of thousands per year. ✅ Which tax strategies attract IRS scrutiny and how to use the tax code to your advantage without crossing red lines. Show Notes: LifestyleInvestor.com/276 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review. Connect with Justin Donald FacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.