Podcast Episodes

SpaceX's IPO, Estate Planning Without Kids & Tax Gain Harvesting Strategies (6/6/2026)

What happens to your money, your assets, and even your digital life if you don't have children to step in?

Jeremiah Bates and Alex Lundgren spend the…

3 months, 2 weeks ago

The Retirement Calculator Problem (Plus RSUs, Stock Options & Company Stock Tax Surprises) (5/30/2026)

Can you really know if you're ready to retire?

Jeremiah and Alex spend much of this episode unpacking one of the most commonly misunderstood tools in…

3 months, 3 weeks ago

When the Paycheck Stops, Then What?

For decades, most people focus on one side of retirement planning: Saving money, building investments, and growing retirement accounts.

But eventuall…

3 months, 3 weeks ago

AI Scams, 401(k) Tax Mistakes, & Expensive Financial Missteps to Avoid (5/16/2026)

Financial problems don't always come from bad decisions—they often come from not understanding the rules. Jeremiah Bates and Nic Daniels break down t…

4 months ago

I'd Retire Tomorrow… If It Weren't for Health Insurance

"I'd retire tomorrow… if it weren't for health insurance." It's one of the most common concerns we hear from people approaching retirement, especiall…

4 months, 1 week ago

Medicaid Myths, IRMAA, & Proper Long-Term Care Preparedness (5/9/2026)

Jeremiah Bates and Alex Lundgren spent Mother's Day weekend tackling one of the biggest financial issues many families avoid until it's too late: lon…

4 months, 1 week ago

Micron's 600% Surge: Why Large Gains Don't Solve Cash Flow (5/2/2026)

What happens when your 401(k) suddenly surges and your lifestyle starts rising with it?

This week, Brian and Jeremiah uses a real example of Micron s…

4 months, 2 weeks ago

Taking Money Out of Retirement Isn't So Simple

Taking money out of your accounts sounds simple… but it's usually not as simple as it seems.

In this episode, Nic walks through why withdrawals are m…

4 months, 3 weeks ago

Self-Employment Tax Shock, Social Security Insolvency, & A Widow's Retirement Plan (4/25/2026)

A simple tax question turns into a bigger realization: even if you don't owe income tax, you can still owe thousands in self-employment tax. Brian an…

4 months, 3 weeks ago

Estate Planning Failures, HSA Tax Strategies, & When DIY Backfires (4/18/2026)

Most people don't have a money problem—they have a follow-through problem. Brian Wiley and Jeremiah Bates use real-life case studies, including a m…

5 months ago