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Why I Don’t Offer Hourly Services

Why I Don’t Offer Hourly Services

"I'd gladly pay you $150 or $200 per hour for a few hours of your time. I'm curious why you don't work hourly?"

Why I Don’t Offer Hourly Financial Planning

Why I Don’t Offer Hourly Financial Planning

"I'd gladly pay you $150 or $200 per hour for a few hours of your time. I'm curious why you don't work hourly?"

The Retiree’s Financial Decathlon

The Retiree’s Financial Decathlon

What are the 10 most important aspects of a financially sound retirement, and how do we start preparing for that future today?

Your Retirement Withdrawal Order of Operations

Your Retirement Withdrawal Order of Operations

A deep (and I mean *DEEP*) dive into optimizing your retirement withdrawal order of operations to make your money last.

11 Ways Retirees Damage Their Retirement Success

11 Ways Retirees Damage Their Retirement Success

Want a successful retirement? Let's use the principal of inversion. We'll identify the common mistakes, and then NOT do those things!

Scar Tissue

Scar Tissue

We make daily financial decisions as a function of long-held beliefs. Some logical and well-thoughts beliefs. Others as a function of pure trauma.

“Asset-Liability Matching” Aligns Your Money to Your Future

“Asset-Liability Matching” Aligns Your Money to Your Future

I see some people thinking about their portfolios incorrectly, and a concept called "asset-liability matching" can help.

Stocks, Rock, and Two Blasting Speakers

Stocks, Rock, and Two Blasting Speakers

Growing up, our neighbor was erratic. He was an unwell man, and it manifested in many ways. Today, we learn from him.

You Win or You Die…or You Just Have a Normal Retirement

You Win or You Die…or You Just Have a Normal Retirement

On perfectionism, theory of mind, and finding a "good enough" path to get through retirement with flexibility.

Are Dividends and Income Part of My Retirement Withdrawal Rate?

Are Dividends and Income Part of My Retirement Withdrawal Rate?

If dividends and investment income are supporting your lifestyle, does that matter for "safe withdrawal rate" retirement math?


Podcast Feed

Scrimping, Splurging, and Other Crazy Spending Stories - E109

Scrimping, Splurging, and Other Crazy Spending Stories - E109

Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, J…

Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108

Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108

Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for h…

19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107

19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107

Today, Jesse is joined by Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-re…

Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106

Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106

Jesse explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning int…

It’s Not Too Late: Smart Money Moves After 50 | Bill Yount - E105

It’s Not Too Late: Smart Money Moves After 50 | Bill Yount - E105

Jesse explores the financial journey of late starters with guest Bill Yount, co-host of Catching Up to FI. In the opening monologue, Jesse shares his…

Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode

Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode

Today, Jesse critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while pr…

"Tax-Free Retirement" - Smart Strategy or Overhyped Gimmick? And Other Listener Questions | AMA #6 - E104

"Tax-Free Retirement" - Smart Strategy or Overhyped Gimmick? And Other Listener Questions | AMA #6 …

Jesse answers listener questions on financial planning, investment management, and retirement. He discusses the challenges of rising homeowner’s insu…

Life-Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103

Life-Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103

Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discus…

Life Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103

Life Expectancy, Caregiving Costs, & Retirement Planning | Christine Benz - E103

Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discus…

The Truth About the U.S. National Debt (And How It Impacts You Personally) - E102

The Truth About the U.S. National Debt (And How It Impacts You Personally) - E102

Today we take a look at the U.S. national debt, distinguishing it from household debt and analyzing its impact on individuals and investors. Jesse tr…


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