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Perfect Game Retirement

Author: Ryan Ledden

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The Perfect Game Retirement Podcast is brought to you by Black Oak Asset Management, serving the greater Atlanta area with offices in Alpharetta, Cartersville and Macon. Former professional baseball player and now financial coach, Ryan Ledden, is your host. This is the show that’ll help you make the right decisions, so you can pitch a ”perfect game” in 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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📅 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’re falling behind? This episode offers clarity about what really determines retirement success. Here’s what we discuss in this episode: 🧠 Comparison Trap: Why savings comparisons destroy confidence 🔄 Reframing Goals: Moving from “my number” to your plan 🧩 What Shapes Outcomes: Lifestyle, debt, benefits, and timing 🚀 Catch-Up Strategies: Practical ways to strengthen retirement readiness   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
📅 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 the year and what actually mattered for long-term planning. The noise will change in 2026, but the strategy that creates confidence stays the same. Here’s what we discuss in this episode: 🌍 Tariffs: Market reactions and volatility 📈 Inflation: Why prices still feel high 🏦 High-Yield Savings: Making cash work harder 🚨 Government Shutdown: Why emergency funds matter 🏢 Federal Resources: Support for government employees   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  
📅 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, and more confidence about the future. The smartest investors don’t just look for answers. They learn to ask better questions. Here’s what we discuss in this episode: 💰 Income Clarity: What you need vs. what you’ve saved 🏥 Long-Term Care: Exploring real options 🧾 Tax Strategy: Planning ahead, not just this year but beyond 🛑 Social Security: Smarter claiming decisions, not guesswork 💳 Debt Management: Reducing pressure in retirement 📉 Market Volatility: Adjusting portfolios thoughtfully   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
📅 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 explain what to watch for before small issues become costly mistakes. A great advisor builds trust, listens well, and never leaves you feeling in the dark. Here’s what we discuss in this episode: 📈 Overpromising Returns: unrealistic expectations and guarantees 🧾 Tax Blind Spots: missing long-term tax coordination 📅 Outdated Plans: set-it-and-forget-it approach 🤝 Built Trust: strong relationships and transparency   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
📅 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 wondered how to “team up” financially while keeping your money separate, this conversation gives you a blueprint. Here’s what we discuss in this episode: 💍 Later-Life Remarriage: unique challenges couples face when they maintain separate assets 📖 Ground Rules & Transparency: sharing enough financial info to build a real plan 📜 Estate Planning Essentials: wills, trusts, prenups, and protecting blended families 🧭 Advisor as Mediator: how a planner provides objectivity and reduces emotional friction   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
📅 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. The goal is to support causes you care about while staying thoughtful about timing, taxes, and long-term strategy. Here’s what we discuss in this episode: ❤️ The “Why” Behind Giving: impact on your life, family, and community 📅 Timing Your Gifts: how year-round giving differs from seasonal giving 🧾 Tax-Smart Strategies: deductions, planning, and getting more mileage from every dollar 💸 Types of Giving: comparing cash gifts, QCDs, and donor-advised funds   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
📅 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 create a stronger financial foundation no matter what’s going on around you. Here’s what we discuss in this episode: 💰 Emergency Funds & Investing: building a strong base before taking risks 📉 Debt & Budgeting Solutions: cutting costs and organizing a workable plan 🧩 Budgeting Challenges: fixing the habits and hurdles that derail progress 🔄 Income & Expense Shifts: adjusting where money flows as life changes 🤝 Accountability & Communication: staying consistent through honest conversations and support   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
📅 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 the habits and decisions that quietly sabotage progress and share practical ways to get back on track. Here’s what we discuss in this episode: 🚩 Red Flags: common warning signs of a bad advisor relationship 💬 Communication Gaps: what it means when you feel “in the dark” 🤝 Advisor Fit: the importance of trust and transparency 📊 Financial Coaching: how accountability builds long-term success 🧭 Proactive Planning: why good advisors educate instead of sell   Learn more about Financial Coach Bob Ginty: www.setfreefinancialcoaching.net  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
📅 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 unified plan often leads to better results. At the end of the day, it’s not about how many people manage your money, it’s about how coordinated your strategy is. Here’s what we discuss in this episode: 🚫 Hidden Challenges: How conflicting advice can cause confusion and mistakes 🤝 Trust Matters: Why credentials and personal connection should drive your choice 📊 One Team Approach: How a single advisory team provides internal diversification 💸 Avoiding Overlap: Preventing duplicate investments and unnecessary fees   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
📅 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 your feelings about home, debt, giving, and family can quietly shape your entire financial plan. At the end of the day, numbers give us the framework, but your feelings help define the plan that truly fits you. Here’s what we discuss in this episode: 🏠 Where You Live: how emotional ties influence retirement location decisions 📊 Investment Preferences: balancing detail-oriented and big-picture mindsets 💳 Debt Decisions: finding peace between logic and emotion 📉 Market Emotions: staying grounded when volatility strikes 🎁 Giving & Legacy: weaving generosity and purpose into your financial plan   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
📅 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 it matters, and how to prepare before medical costs derail your plan. Health care is one of retirement’s biggest wildcards, but with the right strategy, you can make it just another budget item, not a financial shock. Here’s what we discuss in this episode: 💊 The Inflation Effect: health costs have more than doubled since 2002 🏥 Medicare Myths: it’s not free and doesn’t cover everything 🧓 Gen X Wake-Up Call: 1 in 4 haven’t planned for health care costs 💰 HSA Power: use the triple tax advantage to grow medical savings 🧠 Don’t Panic, Plan: turn the wildcard of health care into a checklist item   Fidelity Investments® Releases 2025 Retiree Health Care Cost Estimate: https://newsroom.fidelity.com/pressreleases/fidelity-investments--releases-2025-retiree-health-care-cost-estimate--a-timely-reminder-for-all-gen/s/3c62e988-12e2-4dc8-afb4-f44b06c6d52e    Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI
📅 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 process for helping clients determine where to invest. It’s interesting to hear what other pros recommend, but the reality is that every million-dollar plan is unique. Age, goals, family, and even your sleep-at-night factor matter more than an allocation pie chart. Here’s what we discuss in this episode: 🧮 Diversification Basics: Balancing stocks, bonds, and alternatives ⚙️ Risk Tolerance: Matching your comfort level to your strategy 📊 Age Factor: How strategies shift from 40s to 70s 💡 Tax Planning: Placing assets in the right accounts 🤝 Comprehensive Planning: Investments are just one piece of the puzzle   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
📅 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 each impacts your taxes, contributions, and withdrawals. Tune in for practical tips to help you maximize your retirement savings and choose the best approach for your financial goals. Here’s what we discuss in this episode: 💵 Pre-Tax Basics: How Traditional IRAs reduce today’s tax bill 🧾 Roth Advantage: Tax-free growth and withdrawals explained ⚖️ Pay Now or Later: The trade-off that defines both accounts 🧮 Contribution Limits: What you can put in for 2025 🕰️ Age Factor: How timing impacts your long-term tax picture 🔁 Conversions: When to roll pre-tax money into a Roth   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
📅 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 it? In this episode, Ryan answers real listener questions about these exact scenarios, breaking down the tax traps, planning strategies, and smarter ways to make decisions that fit your retirement lifestyle. Here’s what we discuss in this episode: 🚐 Should retirees buy, rent, or finance an RV? 💸 The tax hit of pulling from an IRA 📉 Why debt sometimes beats a lump-sum withdrawal 🧑‍🏫 How hiring a financial advisor can help in the decumulation phase 🎯 Target date funds: pros and limitations 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
📅 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 digs into those unfiltered takes and separates what’s solid from what can steer you wrong. Here’s what we discuss in this episode: 💵 Does taking Social Security early make sense? 🏥 Budgeting for healthcare before Medicare 🧠 Overcoming the fear of spending in retirement 👤 Unique estate and tax challenges for singles   Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI
📅 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 number” varies for everyone and the importance of flexibility in your retirement plan. Here’s what we discuss in this episode: 🏦 How much do you really need for retirement? 💡 Flexibility is key in creating an income plan 📉 The importance of planning for lifestyle expenses 🔄 Adjusting your plan based on market fluctuations   Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI
📅 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. The frustrating part? It’s tied to your income from two years prior, so you might trigger higher premiums without even realizing it. Here’s what we discuss in this episode: 🧾 What IRMAA is and who it will impact 💵 IRMAA Triggers: RMDs, capital gains, pensions, and stock sales 🎯 Tips to avoid IRMAA 🧠 Smart tax planning helps reduce or avoid costly surcharges   Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI
📅 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 future. Don’t let fuzzy math sabotage your future, learn how to spot it before it’s too late. Here’s what we discuss in this episode: 📊 Why a “7% average return” doesn’t guarantee future results 🏦 How dividend investing can backfire despite steady payouts 🛍️ Why retirees often spend just as much—just differently 💰 The danger of assuming lower tax brackets in retirement 🛑 Why counting on part-time work is risky at best   Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI
📅 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 answers a listener’s question on this exact topic. Here’s what we discuss in this episode: ⏳ Claiming at 62 locks in lower benefits for life 📈 Holding off on SS can grow your payout by 8% a year 💑 Spousal benefits and legacy goals change the equation 🛠️ Planning tools can show which claiming age improves your long-term success   Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI
📅 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 analyzes the habits that signal real, lasting wealth and what to do if you are (or aren’t) on the right track. Here’s what we discuss in this episode: 🏦 Emergency funds = hidden wealth 📉 Living below your means pays off 📊 Smart investing builds long-term security 💻 Side hustles & passive income streams matter 📆 Long-term focus beats short-term noise   Visit us online: https://blackoakam.com/ Phone: (470) 508-0508 Get in touch with the Black Oak team: https://blackoakam.com/contact-us/ Get more financial education on our YouTube Channel: https://bit.ly/45kJlwI
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