Perfect Game Retirement

Hosted by Ryan Ledden

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203

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Aug 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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September 3, 2026Episode 20412 min

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 giving the money and the goals of the person receiving it should both be part of the conversation. A generous gift can go much further when there’s a thoughtful plan behind it. Here’s what we discuss in this episode: 🧾 Gifting Rules: Annual exclusions can allow families to transfer significant amounts 🎓 College Funding: A 529 plan may provide flexibility for future education expenses 📈 Investment Options: Joint accounts and custodial accounts offer additional ways to invest 👨‍👩‍👧‍👦 Family Planning: Gifted money can support children, grandchildren, or broader family goals 💬 Open Communication: Families should discuss the purpose and expectations behind larger gifts 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

August 27, 2026Episode 20315 min

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 player has a game plan, but also the discipline to adjust it mid-match without losing their nerve. That's not a bad description of good financial planning either. Here’s what we discuss in this episode: 🎾 Singles vs. Doubles: Couples often have more planning flexibility than individuals 🏆 Specialization Matters: Different advisors may be better suited for different financial needs 🎯 Hold Serve: Focus on savings, debt, and other factors within your control 🚫 Unforced Errors: Emotional decisions can derail an otherwise solid plan ⏳ Long-Term Game: A bad month or year doesn’t define your retirement outcome 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

August 20, 2026Episode 20213 min

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, what goes, and where it all belongs. Nobody loves paperwork, but a little bit of organization now saves a lot of scrambling later for you and for whoever has to help sort it out someday. When in doubt, ask us before you shred it. Here’s what we discuss in this episode: 🗂️ Organizing Documents: A clear system makes important records easier to find 💼 Pay Stubs and Tax Forms: Keep what supports taxes or resolves discrepancies 📈 Investment Statements: Prioritize year-end records over monthly paperwork 📜 Estate Documents: Store current originals securely and permanently 🏦 Loan Paperwork: Keep records until the debt is fully resolved 🗑️ Document Disposal: Shred paperwork containing sensitive personal information 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

August 13, 2026Episode 20113 min

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 wrong call. Sometimes it's exactly right. The real question is whether it's a choice or a fallback. That's worth figuring out before you assume the answer. Here’s what we discuss in this episode: 👥 Extended Workforce Participation: People continue working for many different reasons 🤝 Social Interaction: Work can provide community, identity, and purpose 💵 Money Worries: Leaving a paycheck can create understandable anxiety 🏠 Change at Home: Retirement can reshape routines and relationships 🗺️ Planning Doubts: Uncertainty can make retirement feel too risky 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

August 6, 2026Episode 20015 min

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 retirement without at least one of these on their mind. The good news is that most of them have real answers. And all of them are worth talking about. If any of these hits close to home, that's exactly where our conversation should start. Here’s what we discuss in this episode: 💸 Running Out: Test whether retirement income can last 🧾 Tax Angst: Structure withdrawals for greater tax efficiency 🏥 Long-Term Care: Prepare for possible future care costs 💵 Leaving Paychecks: Replace workplace income with a plan 📉 Market Anxiety: Stress-test retirement against poor returns ✅ Start Talking: Address concerns before retirement begins 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

July 30, 2026Episode 19913 min

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 bad install are a little higher than a crooked backsplash. DIY has its place. But some projects are worth calling a professional, especially when the cost of getting it wrong follows you for the next thirty years. Here’s what we discuss in this episode: 🛠️ DIY Planning: Know when to stay in your lane ⚖️ Cost vs. Value: Decide what professional help is worth 🚨 Common Triggers: Life changes often prompt action 🧩 Planning Mistakes: Small oversights can create major consequences 🤝 First Meeting: Start with conversation, not commitment 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

July 23, 2026Episode 19816 min

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 either means it's a great framework or someone really wanted it to work out that way. In this episode, Ryan walks through the “5 D’s” of retirement planning and how each one plays a role in helping retirees build a plan that can hold up over time. Here’s what we discuss in this episode: 🌐 Diversification: Spread income, investments, and taxes ⏳ Duration: Make your savings last longer 🛡️ Downside Protection: Limit damage during market declines ✈️ Discretionary Income: Plan confidently for life’s enjoyment ⚓ Portfolio Drag: Reduce fees, taxes, and inefficiencies 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

July 16, 2026Episode 19713 min

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 it comes to how much you should pull from your retirement accounts each year, Ramsey takes a position that some financial professionals find hard to get behind. Today, we break it down: what Dave says, what the research says, and what Ryan thinks. Here’s what we discuss in this episode: 📉 Stock Market Risk: Understanding the volatility of an all-stock portfolio 📏 The Traditional Rule: Why 4% became a common retirement benchmark 🚨 The 8% Concern: How withdrawals can magnify losses during a downturn 🧾 Taxes Matter: Choosing which accounts to withdraw from strategically 🧩 Your Personal Number: Building an income plan around your unique needs Check out the article about this topic: https://finance.yahoo.com/news/ramsey-8-retirement-rule-sounds-170209842.html 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

July 9, 2026Episode 19614 min

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 some of the worst financial decisions we see come from people who did a ton of research first. Today, Ryan’s talking about why this happens and what good research actually looks like. Being informed is a good thing. Being confidently misinformed is a different thing entirely. Reach out and let’s have a frank conversation about your financial future. Here’s what we discuss in this episode: 🔍 Advice Sources: Not all voices are equal 🤖 AI Tools: Helpful but not foolproof 🧠 Algorithm Bias: Seeing only one side ⚖️ Research Balance: Avoid analysis paralysis 🤝 Trusted Guidance: Advice tailored to you 🛑 Decision Delays: Research can become a problem 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

July 2, 2026Episode 19516 min

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 conversation, not to tear it apart, but to react honestly. Does Ryan agree? Let's get into it: 3.7 million people watched this video for a reason. It touches something real. Retirement isn't just about what you've accumulated. Sometimes it's about what you're willing to let go of. Here’s what we discuss in this episode: 👨‍👩‍👧 Adult Children: Helping versus enabling 🚤 Expensive Toys: Assets or burdens? 🚗 Second Vehicle: Necessity or extra expense 🪪 Work Identity: Preparing for life's next chapter ⚖️ Personal Choices: No one-size-fits-all answer 🎯 Decision Framework: How to ask better questions Watch the video here: https://www.youtube.com/watch?v=IltvyKpy8Z4 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