Episode 64: Winning the Financial Triple Crown: Strategies from Kentucky Derby

June 4, 2026

Step into Triple Crown season as Dennis uses the excitement of the Kentucky Derby to reveal what it really takes to build a winning retirement plan. He draws parallels between horse racing and financial planning, including how to avoid “long shot” bets with your nest egg. Grab your saddle and your fancy hat and join us at the starting gate as we race toward retirement.

Here’s some of what we discuss in this episode:

- Team Approach: Advisors, CPAs, and attorneys matter

- Protection Planning: Insurance reduces financial roadblocks

- Investment Risks: Long shots rarely win consistently

- Customized Strategies: Every retirement plan is unique, just like the hats at the Kentucky Derby

- Ongoing Adjustments: Retirement plans need regular updates

Go Inside the Episode:

0:00 – Intro

1:09 – The Power of Compound Interest

2:31 – Tension: Savings vs Spending

4:03 – Credit Cards

6:35 – Ignoring the 401k Match