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

January 8, 2026 12 mins

📅 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 days, retiring with $1 million might feel like falling short, especially when everyone around you seems to have more. In this episode, Ryan tackles a listener question that gets to the heart of retirement anxiety: is $1 million actually enough to retire? Are you worried you’...

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📅 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 happened in 2025: political swings, stubborn inflation, new tax rules, and even a historic government shutdown. But headlines alone don’t determine your retirement outcome; how you respond to them does. In this episode, Ryan reflects on the five biggest financial events of t...

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📅 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 heard the phrase, “There’s no such thing as a bad question.” But in retirement planning, the quality of your questions often determines the quality of your outcome. Today Ryan reframes common retirement questions, and shares how clearer question lead to better strategies, a...

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December 18, 2025 11 mins

📅 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 you know if your financial advisor is actually a good fit, or quietly working against your best interests? In this episode, Ryan walks us through common red flags that signal an advisor may not be serving you well. From cookie-cutter plans to poor communication, they explai...

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📅 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 couples are entering marriage later in life with established careers, children from previous relationships, and financial lives they prefer to keep separate. Ryan breaks down how couples can still build a unified retirement plan without combining accounts. If you’ve ever wond...

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December 4, 2025 14 mins

📅 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 Tuesday and year-end donations always spark generosity, but the real impact comes when giving is intentional, not rushed or emotional. Ryan breaks down how to align your generosity with your financial plan so your giving feels meaningful and works smarter behind the scenes....

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📅 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 the fastest way to regain control when your finances feel chaotic? This week, Ryan talks with Ramsey-Preferred Financial Coach Bob Ginty about practical ways to stabilize your finances, even when the economy feels unpredictable. They explore key areas that can help you crea...

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📅 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 missing the warning signs in your financial life? In this episode, Ryan and Ramsey-Preferred Financial Coach Bob Genty discuss the biggest money challenges families are facing today—from overspending and debt stress to a lack of clear financial direction. They break down t...

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📅 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 investors believe having more than one advisor means more ideas, more diversification, and more protection. But in reality, it often creates more confusion than clarity. Ryan breaks down the pros and cons of working with multiple advisors, when it might make sense, and why a ...

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📅 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 people think financial planning is about calculators, spreadsheets, and strategies. But that’s only half the story. The truth is your feelings about money can have just as much impact on your retirement as the numbers do. Today, Ryan explores the human side of money and how...

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📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/

📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html

Fidelity just released their 2025 Retiree Health Care Cost Estimate, and the number is staggering: $172,500 for a 65-year-old retiring today. The bigger problem? One in five Americans hasn’t even thought about health care costs in retirement. Ryan breaks down what this means, why ...

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October 23, 2025 13 mins

📅 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 should a financial advisor do if a client comes in with $1 million in cash to invest? That was the question posed to three financial advisors in a recent article, and their answers sparked a lively debate. Ryan reacts to each of their investment strategies and then shares his...

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📅 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 or after-tax? That is the question. There’s no Life 101 class that talks you through these choices, and one wrong move could impact how much of your retirement savings you get to keep. Ryan breaks down the key differences between Traditional and Roth IRAs, explaining how e...

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📅 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 thought about buying an RV in retirement, but not sure if it makes sense financially? Or maybe you’ve built up a big nest egg but don’t feel confident about how to actually invest or withdraw it. And what about those new Roth 401(k) options showing up at work, are they worth ...

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📅 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 polished advice. If you want the real story on retirement, head to the YouTube comments. That’s where people speak their minds, sharing fears about running out of money, frustrations with the system, and creative strategies they’ve tried themselves. In this episode, Ryan di...

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📅 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 episode, Ryan tackles a listener question about falling short of your retirement savings goal. Beverly’s goal was to reach $1 million in her 401(k), but she’s currently at $850,000 and unsure if she can retire comfortably in just one more year. Ryan shares how the “magic n...

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📅 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 Medicare is free once you hit 65? Not quite. Many retirees are surprised by IRMAA—the Income-Related Monthly Adjustment Amount. This hidden surcharge can quietly increase your Medicare Part B and Part D premiums, shrinking your Social Security check by thousands each year. T...

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📅 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 probably said it before: “I ran the numbers, and I should be fine.” But what if the math you’re relying on isn’t telling the whole story? In this episode, Ryan unpacks some of the most common examples of fuzzy retirement math and how they can quietly derail your financial f...

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📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/

📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html

If your parents passed away relatively young, it’s only natural to wonder whether you’ll follow the same path. And from a financial standpoint, does that change how you should approach things like retirement planning and when to draw Social Security benefits? In this episode, Ryan...

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📅 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 people don’t feel wealthy. But what if your day-to-day habits are quietly building serious financial strength? A recent article from Kiplinger outlined five surprising signs that you might be richer than you think. And none of them involve yachts or private jets. Today, Ryan ...

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