Ep 237: Ask the Professor: Legal Tax Hacks Your CPA Isn’t Talking About

💡 Episode Summary In this week’s Ask the Professor edition of The Weekly Wealth Podcast , host David Chudyk, CFP® , sits down with financial educator and colleague Justin Chastain (“The Professor”) to unpack key tax planning concepts that impact retirement, Social Security, and business owners. Justin—who teaches future CFP® professionals through Dalton Education—shares his trademark mix of deep insight and humor while explaining how proactive tax strategies can create real, lasting wealth. 🧩 Topics Covered 1️⃣ Social Security Taxation How benefits can be taxed at 0%, 50%, or 85% Why income thresholds haven’t changed since 1984 How to plan around working income and Social Security to minimize surprise tax bills 2️⃣ Retirement Accounts & Withdrawals The difference between Traditional IRAs (tax-deferred) and Roth IRAs (tax-free growth) Understanding Required Minimum Distributions (RMDs) When Roth conversions make sense and how to manage tax brackets efficiently 3️⃣ Marginal vs. Effective Tax Rates What your next dollar really gets taxed at How to use bracket management to stay tax-efficient Real examples showing why “being in the 32% bracket” doesn’t mean you’re paying 32% overall 4️⃣ Tax-Loss and Tax-Gain Harvesting Using market volatility to your advantage How to offset gains and manage investment income efficiently Strategies for gifting appreciated stock or donating directly to charities to avoid unnecessary taxes 5️⃣ Legacy & Estate Planning Why charitable giving can reduce both estate taxes and current tax burdens Qualified Charitable Distributions (QCDs) explained How retirees can use RMDs or life insurance to leave a legacy without overpaying Uncle Sam 6️⃣ Business Owner Tax Tips Turning legitimate expenses into deductions Building employee benefits and retirement plans to attract and retain top talent Using goodwill and benefits as part of your company’s long-term value 🎧 Notable Quotes “Money is just a tool to help us live better lives—nothing more, nothing less.” — David Chudyk “Ask your financial advisor: ‘Is tax planning part of your strategy?’ If not, find one who makes it a priority.” — Justin Chastain “It’s not about buying the next hot stock—it’s about knowing where your money is taking you.” — David Chudyk 🗓 Bonus Segment David closes the episode by reminding listeners to collaborate — just as he and Justin do. Partnerships can accelerate your personal and financial growth, whether in business or your financial life. 🔗 Connect with Us 📩 Contact Justin: justin@parallelfinancial.com 📩 Contact David: david@parallelfinancial.com 🌐 Learn more or book your free 10-Minute Vision Call: weeklywealthpodcast.com/vision 📱 Follow The Weekly Wealth Podcast Instagram: @WeeklyWealthPodcast YouTube: Weekly Wealth Podcast Channel Facebook: Weekly Wealth Podcast Community ⚠️ Disclaimer This episode is for educational purposes only and should not be construed as specific tax or investment advice. Always consult with your own financial advisor or CPA before implementing any strategies discussed