The Black Oak Podcast
Check Out Our Latest Episode
Keep It or Toss It? A Financial Document Checklist
Somewhere in a drawer, a filing cabinet, or a shoebox in the closet, most of us are holding onto financial paperwork we don't actually need. And we’re probably missing a few things we do need. Ryan sorts out what stays,...
More Episodes
Why People Keep Working In Their Retirement Years
More people in their 60s and 70s are staying on the job than ever before, and it's not always about the money. Today, Ryan digs into the real reasons retirees keep showing up to work. Working longer isn't automatically the...
The Most Common Financial Pain Points
When it comes to financial planning, everybody has something that bothers them. Today, Ryan’s walking through some of the most common pain points we see and the real conversations that happen around them. Nobody walks into retire-ment without at least...
The DIY Retirement Plan — Where It Works and Where It Gets Expensive
There's an entire television network dedicated to doing things yourself — home renovation, landscaping, interior design, all of it. And the DIY mentality is genuinely admirable. But when it comes to retirement planning, Ryan says that the stakes of a...
The 5 D's of Retirement Planning
According to a recent Kiplinger article, there are five keys to a retirement plan that hold up over time. They all happen to start with the same letter, which either means it's a great framework or someone really wanted it...
The 4% Rule vs. the 8% Rule: What's the Right Withdrawal Rate for You?
Dave Ramsey has built one of the most recognized brands in personal finance. Millions of people have followed his ad-vice out of debt and into savings. But when it comes to how much you should pull from your retirement accounts...
The Problem With Financial Research Today
Financial information has never been more available — TV, podcasts, YouTube, Reddit, and now AI that will answer any question in about three seconds. And yet some of the worst financial decisions we see come from people who did a...
3.7 Million People Watched This Retirement Video — Here's What We Think
Over the past year, one retirement video on YouTube pulled in 3.7 million views. The title: "Sell These 5 Things Before You Retire." We thought it was worth a conversation, not to tear it apart, but to react honestly. Does...
What Does Smart Risk Actually Look Like At Your Age?
Risk is unavoidable. The only question is whether the risk you're taking actually makes sense for where you are in life. Today, Ryan looks at three stages of the financial journey, and at each one, we've got three types of...
How to Spend on Travel Without Derailing Your Retirement
Summer's here. And somewhere between the excitement of planning a big trip and the anxiety of what it costs, a lot of retirees end up doing something that surprises us… they feel guilty about it. They worked hard, saved, planned...
Should You Sacrifice Pension Income for Spousal Protection?
When retirement is around the corner, some of the biggest decisions aren’t about when to retire, they’re about how income continues if one spouse is gone. Ryan walks through a listener question about pension survivor options and why these decisions...
Three Questions From People Thinking About Retiring In 2026
Ryan’s doing something a little different today. Three listeners wrote in with variations of the same question, “Am I ready to retire in 2026?” Same question, three very different situations, three very different answers. If retiring in 2026 is on...
“I Wish I Knew This at 25” — Young Adult Money Mistakes
Spend five minutes on Reddit or YouTube and you’ll find people being brutally honest about what they wish they had done differently with money. Today, Ryan’s pulling from some of those real conversations and breaking down the lessons behind them....
