Shows / Perfect Game Retirement
Perfect Game Retirement
Welcome to Perfect Game Retirement, hosted by Ryan Ledden of Black Oak Asset Management. As a former pro ballplayer and CFP, Ryan combines his love of the game with financial expertise to guide you to a confident retirement. Securities and Advisory Services offered through Silver Oak Securities, Inc., Member FINRA/SIPC. Black Oak Asset Management and Silver Oak Securities, Inc. are not affiliated.
Episodes
- Perfect Game Retirement
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…
- Perfect Game Retirement
Why Retiring In 2026 Is Different Than It Used To Be
Retirement planning today doesn't look like it did even a decade ago, let alone the way it looked for our parents. On this episode, Ryan provides six realities…
- Perfect Game Retirement
So You've Been Named Executor — Now What?
Being named the executor of someone's will can feel like an honor. It can also feel like a lot of pressure. It's more than handing out inheritances. It's…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
Should You Withdraw More From Your IRA Before Tax Rates Rise?
Worrying about future tax rates can make retirees feel like they need to act before the rules change. In this episode, Ryan explains why taking extra money out…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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 advice out of debt and into savings. But when…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
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…
- Perfect Game Retirement
“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…
- Perfect Game Retirement
The Financial Side of Taking Care of the People You Love
Financial planning isn’t really about spreadsheets, rates of return, or chasing the perfect investment strategy. At its core, it’s about making sure the people…
- Perfect Game Retirement
You've Managed Your Own Money Successfully - Why Would You Need an Advisor Now?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html You’ve…
- Perfect Game Retirement
My Investments Underperformed the Market - Should I Fire My Advisor?
It’s a question a lot of people ask at some point: if your investments aren’t keeping up with “the market,” is it time to move on? Ryan breaks down what you’re…
- Perfect Game Retirement
A New Proposal Might Cap Your Social Security Payments
A new proposal out of Washington is adding a fresh angle to the Social Security conversation, and Ryan is breaking down what it could mean. He walks through…
- Perfect Game Retirement
Why Spending in Retirement Is Harder Than It Sounds
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Most…
- Perfect Game Retirement
Long-Term Care Insurance: Worth It or Waste of Money?
Long-term care is one of the biggest financial risks in retirement, and one of the most uncomfortable topics to talk about. Most people know it’s important…
- Perfect Game Retirement
Put Off Social Security Or Start It Earlier?
When should you take Social Security? It’s one of the biggest financial decisions you’ll make in retirement, and one of the easiest to get wrong. It’s not…
- Perfect Game Retirement
Tax Mistakes New Retirees Make
Nobody likes tax season, but for new retirees, the rules can feel completely different. Income changes, required withdrawals begin, and decisions that once…
- Perfect Game Retirement
And the Oscar Goes To... Your Retirement Strategy
The Oscars have passed, but we’re handing out a few awards of our own. Not for films, but for financial planning. Because when you think about it, a great…
- Perfect Game Retirement
Use Target-Date Funds or Customize Your Portfolio?
Target-date funds are one of the most common investments inside retirement plans, largely because they’re simple and automatic. But are they really the best…
- Perfect Game Retirement
Max Out Retirement Accounts or Build Liquidity?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html It’s…
- Perfect Game Retirement
Roth Conversion or Not? How to Know If It’s Right for You
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Roth…
- Perfect Game Retirement
Reacting To Controversial Financial Takes
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html…
- Perfect Game Retirement
At 55, Is It Too Late for a Roth 401(k)?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Many…
- Perfect Game Retirement
A Pension Tradeoff Too Many People Underestimate
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html One of…
- Perfect Game Retirement
10 Retirement Myths Too Many People Still Believe
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html There’s…
- Perfect Game Retirement
Pros & Cons of the New Trump Savings Accounts for Kids
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html A new…
- Perfect Game Retirement
Do I Have Too Much Cash in the Bank?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Having…
- Perfect Game Retirement
I’m 62: Should I File For Social Security Or Wait?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Are you…
- Perfect Game Retirement
Can I Retire With ‘Only’ $1M?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html These…
- Perfect Game Retirement
5 Major Events From 2025 That Impacted Retirement Plans
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html A lot…
- Perfect Game Retirement
How to Ask Better Questions About Retirement
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html You’ve…
- Perfect Game Retirement
Warning Signs You Picked the Wrong Advisor
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html How do…
- Perfect Game Retirement
How to Plan Together When You Keep Finances Separate
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html More…
- Perfect Game Retirement
How to Give with Purpose & Meaning
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Giving…
- Perfect Game Retirement
Smart Ways to Protect Your Finances in an Uncertain Economy with Bob Ginty
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html What’s…
- Perfect Game Retirement
Warning Signs That Financial Trouble Could Be Ahead?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Are you…
- Perfect Game Retirement
Should You Have More Than One Financial Advisor?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Some…
- Perfect Game Retirement
Do Your Feelings Belong in Your Financial Plan?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Most…
- Perfect Game Retirement
Retirement Health Care Costs Just Jumped Again (2025 Update)
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html…
- Perfect Game Retirement
Where Should Someone Invest $1 Million?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html What…
- Perfect Game Retirement
Pre-Tax vs After-Tax Contributions: Which One’s Right for You?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Pre-tax…
- Perfect Game Retirement
Retirement Mailbag: RVs, Roth 401(k)s, and Smarter Investing
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Ever…
- Perfect Game Retirement
Reacting To Unfiltered Retirement Takes from YouTube
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Forget…
- Perfect Game Retirement
What If You Fall Short of Your Retirement Savings Goal?
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html In this…
- Perfect Game Retirement
The Hidden Medicare Penalty You Might Be Paying
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html Think…
- Perfect Game Retirement
Fuzzy Math Could Be Sabotaging Your Financial Future
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/ 📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html You’ve…