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.
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 Dec 18, 2025
Warning Signs You Picked the Wrong Advisor
Thursday Dec 18, 2025
Thursday Dec 18, 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
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.
Hereās what we discuss in this episode:
š Overpromising Returns: unrealistic expectations and guarantees
š§¾ Tax Blind Spots: missing long-term tax coordination
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Outdated Plans: set-it-and-forget-it approach
š¤ Built Trust: strong relationships and transparency
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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/
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 Dec 11, 2025
How to Plan Together When You Keep Finances Separate
Thursday Dec 11, 2025
Thursday Dec 11, 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
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 youāve ever wondered how to āteam upā financially while keeping your money separate, this conversation gives you a blueprint.
Hereās what we discuss in this episode:
š Later-Life Remarriage: unique challenges couples face when they maintain separate assets
š Ground Rules & Transparency: sharing enough financial info to build a real plan
š Estate Planning Essentials: wills, trusts, prenups, and protecting blended families
š§ Advisor as Mediator: how a planner provides objectivity and reduces emotional friction
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 Dec 04, 2025
How to Give with Purpose & Meaning
Thursday Dec 04, 2025
Thursday Dec 04, 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
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.
Hereās what we discuss in this episode:
ā¤ļø The āWhyā Behind Giving: impact on your life, family, and community
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Timing Your Gifts: how year-round giving differs from seasonal giving
š§¾ Tax-Smart Strategies: deductions, planning, and getting more mileage from every dollar
šø Types of Giving: comparing cash gifts, QCDs, and donor-advised funds
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
Wednesday Nov 26, 2025
Smart Ways to Protect Your Finances in an Uncertain Economy with Bob Ginty
Wednesday Nov 26, 2025
Wednesday Nov 26, 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
Whatās 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 whatās going on around you.
Hereās what we discuss in this episode:
š° Emergency Funds & Investing: building a strong base before taking risks
š Debt & Budgeting Solutions: cutting costs and organizing a workable plan
š§© Budgeting Challenges: fixing the habits and hurdles that derail progress
š Income & Expense Shifts: adjusting where money flows as life changes
š¤ Accountability & Communication: staying consistent through honest conversations and support
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 Nov 20, 2025
Warning Signs That Financial Trouble Could Be Ahead?
Thursday Nov 20, 2025
Thursday Nov 20, 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
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 todayāfrom 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.
Hereās what we discuss in this episode:
š© Red Flags: common warning signs of a bad advisor relationship
š¬ Communication Gaps: what it means when you feel āin the darkā
š¤ Advisor Fit: the importance of trust and transparency
š Financial Coaching: how accountability builds long-term success
š§ Proactive Planning: why good advisors educate instead of sell
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Learn more about Financial Coach Bob Ginty: www.setfreefinancialcoaching.netĀ
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 Nov 13, 2025
Should You Have More Than One Financial Advisor?
Thursday Nov 13, 2025
Thursday Nov 13, 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
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, itās not about how many people manage your money, itās about how coordinated your strategy is.
Hereās what we discuss in this episode:
š« Hidden Challenges: How conflicting advice can cause confusion and mistakes
š¤ Trust Matters: Why credentials and personal connection should drive your choice
š One Team Approach: How a single advisory team provides internal diversification
šø Avoiding Overlap: Preventing duplicate investments and unnecessary fees
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 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
Ā
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









