We all want to support the people we care about, but when money enters the equation, even the best intentions can lead to tension. In this episode, Sean unpacks the emotional and financial complexities of lending to family and friends. He offers real-world guidance to help you handle these situations with clarity and care, without putting your own finances at risk.

You’ll also learn why retirees especially need to be cautious when offering help. Plus, Sean shares thoughtful alternatives to lending money that can still make a meaningful difference. If you’ve ever felt torn between helping and protecting your finances, this episode is for you!

Here’s what we discuss in this episode:

💵 The importance of setting clear terms and expectations

🧾 How contracts can protect both finances and relationships

🚫 Don’t lend what you can’t afford to lose

🧠 Consider creative, non-cash ways to help loved ones

0:00 – Intro

0:51 – Trip to Cooperstown, NY

2:29 – Understand how it impacts your relationship

5:01 – Don’t lend money you don’t have

6:38 – Don’t forget about the IRS

7:24 – Get it in writing

8:25 – Offer other ways to help

Looking Back From The Mountaintop