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
Thursday Nov 06, 2025
Do Your Feelings Belong in Your Financial Plan?
Thursday Nov 06, 2025
Thursday Nov 06, 2025
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Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
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Most people think financial planning is about calculators, spreadsheets, and strategies. But thatās 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.
Hereās what we discuss in this episode:
š Where You Live: how emotional ties influence retirement location decisions
š Investment Preferences: balancing detail-oriented and big-picture mindsets
š³ Debt Decisions: finding peace between logic and emotion
š Market Emotions: staying grounded when volatility strikes
š Giving & Legacy: weaving generosity and purpose into your financial plan
Ā
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
Thursday Oct 30, 2025
Retirement Health Care Costs Just Jumped Again (2025 Update)
Thursday Oct 30, 2025
Thursday Oct 30, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ 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 hasnāt 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 retirementās biggest wildcards, but with the right strategy, you can make it just another budget item, not a financial shock.
Hereās what we discuss in this episode:
š The Inflation Effect: health costs have more than doubled since 2002
š„ Medicare Myths: itās not free and doesnāt cover everything
š§ Gen X Wake-Up Call: 1 in 4 havenāt planned for health care costs
š° HSA Power: use the triple tax advantage to grow medical savings
š§ Donāt Panic, Plan: turn the wildcard of health care into a checklist item
Ā
Fidelity InvestmentsĀ® 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-f44b06c6d52eĀ
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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
Thursday Oct 23, 2025
Where Should Someone Invest $1 Million?
Thursday Oct 23, 2025
Thursday Oct 23, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ 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. Itās 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.
Hereās what we discuss in this episode:
š§® Diversification Basics: Balancing stocks, bonds, and alternatives
āļø Risk Tolerance: Matching your comfort level to your strategy
š Age Factor: How strategies shift from 40s to 70s
š” Tax Planning: Placing assets in the right accounts
š¤ Comprehensive Planning: Investments are just one piece of the puzzle
Ā
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
Thursday Oct 16, 2025
Pre-Tax vs After-Tax Contributions: Which Oneās Right for You?
Thursday Oct 16, 2025
Thursday Oct 16, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
Pre-tax or after-tax? That is the question. Thereās 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.
Hereās what we discuss in this episode:
šµ Pre-Tax Basics: How Traditional IRAs reduce todayās tax bill
š§¾ Roth Advantage: Tax-free growth and withdrawals explained
āļø Pay Now or Later: The trade-off that defines both accounts
š§® Contribution Limits: What you can put in for 2025
š°ļø Age Factor: How timing impacts your long-term tax picture
š Conversions: When to roll pre-tax money into a Roth
Ā
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
Thursday Oct 09, 2025
Retirement Mailbag: RVs, Roth 401(k)s, and Smarter Investing
Thursday Oct 09, 2025
Thursday Oct 09, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ 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 youāve built up a big nest egg but donāt 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.
Hereās what we discuss in this episode:
š Should retirees buy, rent, or finance an RV?
šø The tax hit of pulling from an IRA
š Why debt sometimes beats a lump-sum withdrawal
š§āš« How hiring a financial advisor can help in the decumulation phase
šÆ 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
Thursday Oct 02, 2025
Reacting To Unfiltered Retirement Takes from YouTube
Thursday Oct 02, 2025
Thursday Oct 02, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ 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. Thatās where people speak their minds, sharing fears about running out of money, frustrations with the system, and creative strategies theyāve tried themselves. In this episode, Ryan digs into those unfiltered takes and separates whatās solid from what can steer you wrong.
Hereās what we discuss in this episode:
šµ Does taking Social Security early make sense?
š„ Budgeting for healthcare before Medicare
š§ Overcoming the fear of spending in retirement
š¤ Unique estate and tax challenges for singles
Ā
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
Thursday Sep 25, 2025
What If You Fall Short of Your Retirement Savings Goal?
Thursday Sep 25, 2025
Thursday Sep 25, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ 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. Beverlyās goal was to reach $1 million in her 401(k), but sheās currently at $850,000 and unsure if she can retire comfortably in just one more year. Ryan shares how the āmagic numberā varies for everyone and the importance of flexibility in your retirement plan.
Hereās what we discuss in this episode:
š¦ How much do you really need for retirement?
š” Flexibility is key in creating an income plan
š The importance of planning for lifestyle expenses
š Adjusting your plan based on market fluctuations
Ā
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
Thursday Sep 18, 2025
The Hidden Medicare Penalty You Might Be Paying
Thursday Sep 18, 2025
Thursday Sep 18, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ 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 IRMAAāthe 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? Itās tied to your income from two years prior, so you might trigger higher premiums without even realizing it.
Hereās what we discuss in this episode:
š§¾ What IRMAA is and who it will impact
šµ IRMAA Triggers: RMDs, capital gains, pensions, and stock sales
šÆ Tips to avoid IRMAA
š§ Smart tax planning helps reduce or avoid costly surcharges
Ā
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
Thursday Sep 11, 2025
Fuzzy Math Could Be Sabotaging Your Financial Future
Thursday Sep 11, 2025
Thursday Sep 11, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
Youāve probably said it before: āI ran the numbers, and I should be fine.ā But what if the math youāre relying on isnāt 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. Donāt let fuzzy math sabotage your future, learn how to spot it before itās too late.
Hereās what we discuss in this episode:
š Why a ā7% average returnā doesnāt guarantee future results
š¦ How dividend investing can backfire despite steady payouts
šļø Why retirees often spend just as muchājust differently
š° The danger of assuming lower tax brackets in retirement
š Why counting on part-time work is risky at best
Ā
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
Thursday Sep 04, 2025
If I Wonāt Live to 90, Should I Claim Social Security Early?
Thursday Sep 04, 2025
Thursday Sep 04, 2025
š
Book a 1-on-1 with Ryan: https://speakwithryan.com/
š¦ Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
If your parents passed away relatively young, itās only natural to wonder whether youāll 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 listenerās question on this exact topic.
Hereās what we discuss in this episode:
ā³ Claiming at 62 locks in lower benefits for life
š Holding off on SS can grow your payout by 8% a year
š Spousal benefits and legacy goals change the equation
š ļø Planning tools can show which claiming age improves your long-term success
Ā
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









