Perfect Game Retirement

Hosted by Ryan Ledden

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Episodes

192

Latest episode

Jun 2026

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About the show

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.

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60 recent

June 11, 2026Episode 19213 min

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 often become more emotional and permanent than people expect. A thoughtful retirement income strategy can make these choices much easier to navigate down to road, so start early. Here’s what we discuss in this episode: 💵 Pension Tradeoffs: Bigger income may increase future risk 🛡️ Longevity Risk: Survivor income matters long term 📈 Invest-The-Difference: Great in theory, harder in practice 💍 Spousal Protection: Survivor options create stability 📋 Permanent Decisions: Pension elections usually can’t be reversed Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

June 4, 2026Episode 19114 min

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 your mind, your version of this question is the one that matters most. And it probably has its own wrinkles, its own gaps, its own version of “almost ready”. That's exactly the kind of thing worth sitting down and figuring out together. Here’s what we discuss in this episode: 📉 Market Volatility: Cash reserves help reduce timing risk 🎯 Purpose in Retirement: Retiring to something matters 🏥 Healthcare Planning: Medicare gaps require a strategy 💼 Pension Decisions: Timing can change outcomes 📊 Personalized Planning: Generic retirement advice falls short Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

May 28, 2026Episode 19017 min

“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. The best time to learn any of these lessons was at 25. The second-best time is right now. If you're ready to stop leaving opportunity on the table, let's talk about what that looks like for you specifically. Here’s what we discuss in this episode: ⏳ Time Is Your Biggest Asset 💳 Credit Cards Compound Fast 📈 Inflation Punishes Cash 🎁 Free Money Gets Missed 🧭 Small Habits Create Big Results Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

May 21, 2026Episode 18914 min

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 you love are protected if life takes an unexpected turn. Ryan discusses the often-overlooked side of financial planning and shares how to navigate difficult family moments with clarity. Tune in to make sure you’re protecting what matters most. Here’s what we discuss in this episode: ❤️ Financial Planning Is Personal 🛡️ Life Insurance Still Matters 📄 Beneficiary Mistakes ⏳ Longevity Changes Everything 🤝 Trusted Guidance Matters Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

May 14, 2026Episode 18815 min

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 done a great job managing your money over the years, but retirement changes the game. Ryan looks at the decision many investors face: should you keep doing it yourself, or bring in a financial advisor? He walks through what actually changes in retirement, where costly mistakes tend to happen, and how to think about getting help without feeling like you’re giving up control. Here’s what we discuss in this episode: 🧾 Tax Efficiency: Withdrawal strategy matters ⚠️ Higher Stakes: Mistakes cost more now 🧩 More Complexity: Medicare, Social Security, RMDs 🔒 Fear of Losing Control: Remember that you still own your money 🤝 First Meeting: Low pressure, clarity-focused Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

May 7, 2026Episode 18713 min

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 actually comparing against, why that comparison can be misleading, and what really matters when evaluating performance. The right benchmark isn’t the market, it’s your plan. Here’s what we discuss in this episode: 📊 Wrong Benchmark: S&P 500 isn’t always the right comparison ⚖️ Consistency Matters: Stable returns beat big swings in retirement ⏳ 1-Year Noise: Short-term performance can mislead ⚠️ True Red Flags: Long-term lag + no adjustments 📉 Risk Alignment: Returns must match your comfort level Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

April 30, 2026Episode 18613 min

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 what’s being discussed, who it might impact, and how it fits into the bigger picture of Social Security’s future. The details may change, but the reality is this: something will eventually have to give. Understanding the possibilities now can help you make better decisions later. Here’s what we discuss in this episode: 💰 New Proposal: Cap benefits based on income 📉 Benefit Limits: $100K couples, $50K individuals 📊 Who’s Impacted: Higher earners are most affected ⚠️ System Pressure: Fewer workers supporting more retirees (clear warning) 📈 Plan Ahead: Model multiple Social Security scenarios Find out your benefits estimate: www.ssa.gov Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

April 23, 2026Episode 18515 min

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 retirement conversations are about saving enough, but Ryan flips the script and talks about what happens after you get there. Why is it so hard to actually spend the money you worked decades to build? This episode dives into the mindset shift, the emotional hurdles, and the role a real plan plays in giving you confidence. A good financial plan doesn’t just protect your future, it helps you actually enjoy it. Here’s what we discuss in this episode: 🔄 Mindset Shift: Saving habits don’t just turn off 📉 Market Fear: Pullbacks make spending harder 📄 Written Plan: Clarity builds confidence ⚠️ Guilt Factor: Spending can feel uncomfortable 🤝 Coaching Matters: Consistency builds trust Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

April 16, 2026Episode 18412 min

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, but few have a clear plan for how they’ll actually handle the cost if care is needed. Today, Ryan provides practical tips on how to think through long-term care planning from multiple angles, and how to decide what makes sense based on your health, assets, and goals. Here’s what we discuss in this episode: 💸 Self-Funding Reality: Setting aside assets can be a viable alternative to insurance 📉 Premium Challenges: Costs can rise quickly, and approval isn’t guaranteed ⏳ Age Factor: Waiting too long can make coverage expensive or unavailable 🧬 Health Matters: Medical history plays a major role in eligibility 🔄 Alternative Strategies: Hybrid life insurance options can provide flexibility Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI

April 9, 2026Episode 18313 min

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 about finding “the best” age, it’s about making an educated decision based on your health, income needs, taxes, and long-term goals. Today, Ryan breaks down the key tradeoffs between claiming early, waiting until full retirement age, or delaying all the way to 70. Here’s what we discuss in this episode: 🧮 Claiming Strategy Basics: Timing is an educated guess based on multiple factors 📉 Early Claim at 62: Roughly 30% lower benefit for life ⏳ Delaying for Bigger Benefits: About 8% increase per year after FRA 💼 Still Working & Social Security: Income can temporarily reduce benefits 🧠 Plan with Precision: Coordination can add significant lifetime value Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Schedule a call with Ryan: https://speakwithryan.com/ Get your tax-free retirement toolkit: https://bit.ly/3PMjKqc Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI