The Black Oak Podcast
Check Out Our Latest Episode
Playing It Too Safe: The Risk Nobody Warns You About
We spend a lot of time talking about the danger of taking too much risk. Today Ryan’s flipping it around. For a lot of retirees, the bigger threat isn’t losing money in a market drop. It’s slowly coming up short...
More Episodes
How Do You Know When It's "Safe" to Retire?
"When can I retire?" might be the question we get asked more than any other. A lot of people anchor retirement to a certain age or a certain account balance, but neither one tells the whole story. What really matters...
Why Retiring In 2026 Is Different Than It Used To Be
Retirement in 2026 isn't what it was for your parents. Here are six changes to plan for: staying active, easing out of work gradually, fewer pensions, Social Security's role, caring for parents and kids at once, and inflation. Retirement planning...
So You've Been Named Executor — Now What?
Just been named executor of a will? Here are the common first steps, from getting death certificates and locating the will to updating beneficiaries, and where a financial advisor can help. Being named the executor of someone's will can feel...
Questions Worth Asking About Your Financial Future
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...
When I Retire, I Will... A Financial and Life Planning Conversation
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...
Can You Retire Before 59½?
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...
Ron's Story: He Planned to Retire at 67. Then He Lost His Job at 64.
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...
My Parents Are Gifting Us Money. What Should We Do With It?
Receiving a financial gift from your parents can create a great opportunity, but also plenty of questions about what to do next. Ryan walks through several ways families might use gifted money and explains why the intentions of the person...
Holding Serve: Tennis Lessons for Your Money
The 146th US Open tennis tournament gets underway at the end of August, so Ryan figured it was a good excuse to see what tennis can teach us about financial planning. Turns out, more than you'd think. Every great tennis...
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,...
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...
