The Black Oak Podcast

The Perfect Game Retirement podcast covers retirement planning, investment fundamentals, tax considerations, Social Security decisions, and the behavioral side of managing money. Hosted by Ryan Ledden, each episode is built around education first, helping you understand your options so you can make more informed decisions.

More Episodes

Questions Worth Asking About Your Financial Future

10/08/2026

Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Ryan goes over a few today that he thinks are worth asking. None of these questions are really about...

Questions Worth Asking About Your Financial Future

When I Retire, I Will... A Financial and Life Planning Conversation

10/01/2026

There's a 7-minute animated short that got nominated for an Oscar this year called Retirement Plan. It's free on YouTube, narrated by Irish actor Domhnall Gleeson, and it follows a middle-aged man named Ray who spends his days listing eve-rything...

When I Retire, I Will... A Financial and Life Planning Conversation

Can You Retire Before 59½?

09/17/2026

If you’re ready to leave your career but think your retirement accounts are keeping you trapped, you may have more options than you realize. Ryan answers a listener question from a 56-year-old who wants to retire after 25 years with...

Can You Retire Before 59½?

Ron's Story: He Planned to Retire at 67. Then He Lost His Job at 64.

09/10/2026

Today, Ryan walks through a potential retirement story in chapters. As each new detail comes in, he’ll react to it the way a financial advisor would in a real-time meeting. Ron's 64, figured a lot of this out on his...

Ron's Story: He Planned to Retire at 67. Then He Lost His Job at 64.

Let’s Meet.

We’re educators first. Coaches second. And Advisors third. In that order. Let’s answer your questions first and figure out where to go from there.