Perfect Game Retirement

Hosted by Ryan Ledden

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210

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Oct 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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October 15, 2026Episode 21016 min

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 paperwork, accounts, taxes, property, creditors, and sometimes family dynamics, stretched out over months or even years. A lot of clients end up in this role without ever planning to, and we're often the first call they make. Today, Ryan talks through how he can help. He’s not an estate attorney, and he’s not trying to be. But when a client is staring down this role for the first time, having someone who can help them make sense of it makes a real difference. Here’s what we discuss in this episode: 🤝 Advisor Role: Provide financial guidance through transitions 📋 First Steps: Work through an executor checklist 🗂️ Documents: Locate important estate information early 👥 Beneficiaries: Keep account designations up to date 📝 Estate Tools: Coordinate wills, trusts, and directives 👨‍👩‍👧 Family Conflict: Clarify possessions before disputes arise 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

October 8, 2026Episode 20916 min

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 thinks are worth asking. None of these questions are really about money. That's kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely. Here’s what we discuss in this episode: 🧠 Beyond Math: Look past numbers alone 🕙 Tuesday Morning: Picture everyday retirement life 🧞 Money Problems: Identify your biggest financial concerns ❤️ Passions: Define what gives life purpose 🔙 Past Lessons: Learn from previous money mistakes 🪣 Bucket List: Put timelines around big goals 🧭 Lifestyle Planning: Build real life into the 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

October 1, 2026Episode 20815 min

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 Gleeson, and it follows a middle-aged man named Ray who spends his days listing everything he plans to do once he finally retires. Ryan uses the short as a jumping-off point for a bigger conversation about the expectations we build around retirement and the life we’re living right now. Here’s what we discuss in this episode: 💵 Pension Planning: Why understanding your retirement benefits matters before making permanent decisions ✈️ Travel Goals: Turning “I’ll travel more someday” into an actual financial plan ❤️ Giving Back: Using retirement assets strategically when charitable giving matters to you ⚖️ Life Balance: Saving for the future without sacrificing everything you could enjoy today 🕰️ More Time: Learning how to say yes—and no—when retirement gives you greater control of your schedule 🌅 Present Living: Why the film’s message about being “aggressively present” hits especially hard 📝 Your Own List: Using the short film as inspiration to think about what you want retirement to look like “Retirement Plan” (2026 Oscar Nominee) | The New Yorker - https://www.youtube.com/watch?v=2Mqa4zfJdx4 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

September 24, 2026Episode 2078 min

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 of an IRA simply out of fear may create new problems if it isn’t part of a larger strategy. He looks at the importance of understanding how one tax decision can affect the rest of your financial plan. Don’t guess where tax rates are headed, make intentional decisions with the options available today. Here’s what we discuss in this episode: ⚖️ Withdrawal Strategy: The difference between taking what you need and pulling out extra money 🔄 Roth Conversions: Why converting excess IRA dollars may be more efficient than simply withdrawing them 📈 Reinvesting Funds: What to consider if extra withdrawals are moved into a taxable brokerage account 🛍️ Spending Risk: How easier access to cash can make it more tempting to spend 📊 Tax Brackets: Why current deductions and tax thresholds matter when deciding how much to withdraw 🧩 Full Plan Impact: How one tax move can affect income, investments, and other planning decisions 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

September 17, 2026Episode 20611 min

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 listener question from a 56-year-old who wants to retire after 25 years with the same company but assumes the money is still off-limits. Before assuming you have to keep working for several more years, it’s worth finding out what options are actually available to you. Here’s what we discuss in this episode: 💰 Roth Contributions: Understanding what may be available early 📈 Brokerage Accounts: Building flexible non-retirement savings 🏠 Other Income: Using investments or real estate for flexibility 🧾 Tax Considerations: Understanding potential capital gains ⚠️ Limited Flexibility: Why withdrawal strategies need careful planning 🗺️ Early Retirement Plan: Coordinating the pieces before quitting 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

September 10, 2026Episode 20519 min

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 real-time meeting. Ron's 64, figured a lot of this out on his own, and this is his first time sitting down with a professional. Ron always figured he'd know when he was ready to retire. Turns out, sometimes retirement decides for you. The good news is his plan still has options (pickleball included). If your story feels like Ron's, that's exactly the conversation worth having. Here’s what we discuss in this episode: 🏓 New Routine: Discovering retirement may feel better than expected 🏥 Healthcare Gap: Bridging the years before Medicare 📆 Social Security: Weighing the impact of claiming decisions 💵 Withdrawal Shift: Moving from saving to spending 🧭 Earlier Preparation: Why planning in your 50s 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

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