Fall Money Fire Drill Episode #26

The 5 Questions I Ask Every New Client Before We Do Anything Else

Before I ever recommend an investment, I ask five questions. Not about stocks. Not about the market. Not about what your neighbor is buying. Because great retirement planning has very little to do with chasing returns—and everything to do with building a strategy around your actual life. In this episode, I walk through the five questions I ask every new client to uncover: * What “work optional” really looks like for them * Where their retirement income will actually come from * The tax risks hiding inside their current accounts * What happens if life doesn’t go according to plan * What they’re truly optimizing for: lifestyle, legacy, flexibility, or something else This episode pulls back the curtain on how I work, how real financial planning should feel, and why a portfolio alone is not a retirement plan. If you can’t clearly answer these five questions… you may be guessing more than you think.

The Tax Move Most W-2 Employees Are Missing in Their 40s and 50s

Most high-income W-2 employees are doing exactly what they were told to do: Max out the 401(k). Save aggressively. Keep building. The problem? Almost nobody is showing them what happens later. In this episode, I break down one of the most overlooked tax strategies I see with professionals in their 40s and 50s—and why waiting too long to address it can create a massive tax problem in retirement. We cover: * Why “tax deferred” doesn’t always mean “tax efficient” * The hidden future risk of large pre-tax retirement accounts * How backdoor Roth strategies work * Why Roth conversion planning matters before RMDs begin * The difference between tax preparation and actual tax planning If you’re building wealth but haven’t thought about what your tax bracket could look like at 70… this episode is for you. Because retirement planning isn’t just about growing your money. It’s about keeping more of it.

Why I Only Work With People Who Haven’t Retired Yet

You don’t mess up retirement at 65… You lock in the mistakes at 45. In this episode, I break down why I focus on the Retirement Red Zone—the 10–20 years before you retire—and why that’s where the biggest financial decisions actually get made.

Fall Money Fire Drill Episode #26

🔥 FALL MONEY FIRE DRILL: TIME TO UN-EFF YOUR FINANCES 🍁💸 It’s that time again — the leaves are falling, pumpkin spice is attacking everything, and your money might be feeling a little… crispy around the edges. So here’s your 5-step Fall Money Fire Drill to go from Hot Mess Express to Game Day Ready: 1️⃣ Cash-Flow Reset – Give your money a job. Bills. Buffer. Goals. (No freeloaders allowed.) 2️⃣ Subscription Sweep – Those “free trials” that grew into $14.99 zombies? Time to cancel ’em. 3️⃣ Debt & Rate Reality Check – Anything over 7% interest is your enemy. Choose your weapon: Avalanche or Snowball. 4️⃣ Safety Nets You’ll Actually Use – Beneficiaries, insurance, credit freeze, digital vault. Do it before Netflix asks if you’re still watching. 5️⃣ Tax Moves Now, Not December – 401(k) match, HSA, Roth check, and maybe a DAF play if you’re feeling generous and strategic. 💥 Run this checklist and your finances go from chaos to calm — no New Year’s resolutions required. 👇 Comment “CHECKLIST” and I’ll send you the full Un-Eff Your Finances: Fall Money Fire Drill guide.

Open Enrollment Pop Quiz – Episode 25

💼 Open Enrollment: The Annual Game of “Guess What These Benefits Actually Mean” Every fall, HR drops that mysterious email: “It’s time for open enrollment!” And suddenly, you’re scrolling through options that sound like they were written by a committee of lawyers and robots. ☠️ “High-Deductible Health Plan” sounds scary. 💰 “Health Savings Account” sounds like a trap. 💡 And “Flexible Spending Account”? Not flexible enough when you forget to use it by December. That’s where planning actually pays off. In this week’s video, I break down how to make smart benefit elections that fit your financial plan, not just your employer’s brochure. Because open enrollment shouldn’t feel like a pop quiz you didn’t study for.