
Advertise on podcast: Perfect Game Retirement
Rating
4.9from
This podcast has
185 episodes
Language
EnglishPublisher
Ryan LeddenExplicit
No
Date created
2020/01/28
Latest episode
2026/04/23
Average duration
15 min.
Release period
7 days
Description
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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Check latest episodes from Perfect Game Retirement podcast
Why Spending in Retirement Is Harder Than It Sounds
2026/04/23
📅 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 retirement conversations are about saving enough, but Ryan flips the script and talks about what happens after you get there. Why is it so hard to actually spend the money you worked decades to build? This episode dives into the mindset shift, the emotional hurdles, and the role a real plan plays in giving you confidence. A good financial plan doesn’t just protect your future, it helps you actually enjoy it.
Here’s what we discuss in this episode:
🔄 Mindset Shift: Saving habits don’t just turn off
📉 Market Fear: Pullbacks make spending harder
📄 Written Plan: Clarity builds confidence
⚠️ Guilt Factor: Spending can feel uncomfortable
🤝 Coaching Matters: Consistency builds trust
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
Long-Term Care Insurance: Worth It or Waste of Money?
2026/04/16
Long-term care is one of the biggest financial risks in retirement, and one of the most uncomfortable topics to talk about. Most people know it’s important, but few have a clear plan for how they’ll actually handle the cost if care is needed. Today, Ryan provides practical tips on how to think through long-term care planning from multiple angles, and how to decide what makes sense based on your health, assets, and goals.
Here’s what we discuss in this episode:
💸 Self-Funding Reality: Setting aside assets can be a viable alternative to insurance
📉 Premium Challenges: Costs can rise quickly, and approval isn’t guaranteed
⏳ Age Factor: Waiting too long can make coverage expensive or unavailable
🧬 Health Matters: Medical history plays a major role in eligibility
🔄 Alternative Strategies: Hybrid life insurance options can provide flexibility
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
Put Off Social Security Or Start It Earlier?
2026/04/09
When should you take Social Security? It’s one of the biggest financial decisions you’ll make in retirement, and one of the easiest to get wrong. It’s not about finding “the best” age, it’s about making an educated decision based on your health, income needs, taxes, and long-term goals. Today, Ryan breaks down the key tradeoffs between claiming early, waiting until full retirement age, or delaying all the way to 70.
Here’s what we discuss in this episode:
🧮 Claiming Strategy Basics: Timing is an educated guess based on multiple factors
📉 Early Claim at 62: Roughly 30% lower benefit for life
⏳ Delaying for Bigger Benefits: About 8% increase per year after FRA
💼 Still Working & Social Security: Income can temporarily reduce benefits
🧠 Plan with Precision: Coordination can add significant lifetime value
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
Tax Mistakes New Retirees Make
2026/04/02
Nobody likes tax season, but for new retirees, the rules can feel completely different. Income changes, required withdrawals begin, and decisions that once lowered taxes can create bigger bills later. Ryan unpacks some of the most common retirement tax mistakes and how they show up in real life. A little forward planning can make a dramatic difference over the long run.
Here’s what we discuss in this episode:
💸 RMD Deadlines: Missing required distributions can trigger steep penalties
🔁 Roth Conversion Timing: Poor timing can push you into higher tax brackets
📊 Social Security Taxes: Benefits are often taxable sooner than expected
👫 Survivor Planning: Tax brackets can worsen for a surviving spouse
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
And the Oscar Goes To... Your Retirement Strategy
2026/03/26
The Oscars have passed, but we’re handing out a few awards of our own. Not for films, but for financial planning. Because when you think about it, a great retirement plan has a lot in common with a great movie: strong characters, a clear storyline, the right support, and a structure that holds up no matter what twists come your way. Ryan shares the key elements of an “award-winning” retirement strategy, one that’s not just impressive on paper, but actually works in real life.
Here’s what we discuss in this episode:
💰 Best Actor: Consistent saving and capturing employer retirement plan matches
🏆 Supporting role: Strategic tax planning to keep more of your money
📜 Best Screenplay: Coordinating income sources with your retirement goals
🎼 Best Score: Advisor guiding and aligning all moving parts
🎬 Best Picture: A simple, cohesive financial plan that ties everything together
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
Use Target-Date Funds or Customize Your Portfolio?
2026/03/19
Target-date funds are one of the most common investments inside retirement plans, largely because they’re simple and automatic. But are they really the best option for your long-term portfolio? In this episode, Ryan explains how these funds work, why they’ve become so popular, and where they may fall short for investors who want a strategy tailored to their situation.
Here’s what we discuss in this episode:
🎯 Target-Date Basics: Funds automatically adjust risk over time
⚠️ One-Size Limits: Age alone doesn’t define risk tolerance
🧩 Portfolio Customization: Personalized portfolios can better match goals
📊 Investment Transparency: Many investors don’t know what’s inside the fund
🤝 Advisor Guidance: Financial planning helps tailor investment 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
Max Out Retirement Accounts or Build Liquidity?
2026/03/12
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/
📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
It’s one of the most common investing questions: should you keep funneling money into retirement accounts or build accessible capital you can use anytime? Both paths can work and both have tradeoffs. Today, Ryan explores the strategic thinking behind each approach and why the right answer often depends less on age and more on flexibility, discipline, and long-term tax awareness.
Here’s what we discuss in this episode:
💰 Contribution Strategy – Retirement accounts vs liquid assets
🧾 Tax Benefits – Pre-tax savings and income reduction
🎯 Employer Match – Vesting schedules and forfeiture rules
📉 Capital Gains – Tax rates and withdrawal strategy
📊 Diversification – Asset location and account structure
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
Roth Conversion or Not? How to Know If It’s Right for You
2026/03/05
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/
📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
Roth conversions have gained serious attention over the past several years. With fewer income limitations and more flexibility in today’s tax code, many investors are asking the same question: Should I be converting my IRA to Roth?
Ryan explains how Roth conversions actually work and breaks down when — and if — they make sense for your situation. Before you convert a single dollar, make sure the strategy fits your broader retirement plan.
Here’s what we discuss in this episode:
🔄 How It Works: Paying taxes now for tax-free growth later
⚖️ Pros & Cons: Upfront tax cost vs long-term flexibility
📊 Tax Bracket Planning: When conversions make the most sense
🪣 Tax Diversification: Pre-tax, taxable, and Roth balance
💵 Practical Planning: Using tax software and CPA coordination
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
Reacting To Controversial Financial Takes
2026/02/26
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/
📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
Everyone’s got an opinion about money (especially the people with a book deal or a TV show). Some of that advice is useful. Some of it sounds better on a stage than it works in real life. Today, Ryan breaks it all down. Financial hot takes can be entertaining, motivating, and occasionally unhinged. The key is knowing which advice fits your life and circumstances and ignoring the irrelevant stuff.
Here’s what we discuss in this episode:
💰 Kiyosaki’s Risk Play: Entrepreneurship, gold, Bitcoin volatility
🏠 Real Estate & Leverage: Long-term value vs high-risk borrowing
📉 8% Withdrawal Rule: Too aggressive for most retirees
🧠 Behavior Beats Math: Discipline drives outcomes
🤖 AI Abundance Theory: Skepticism about retirement irrelevance
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
At 55, Is It Too Late for a Roth 401(k)?
2026/02/19
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/
📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
Many people assume Roth strategies are only for younger savers, but that belief might narrow your options later in life. In this episode, Ryan responds to a question that highlights how career changes and timing can reshape retirement decisions. The real issue isn’t age, it’s understanding your options when it matters most.
Here’s what we discuss in this episode:
⚖️ Roth vs. Traditional 401(k): How the tax treatment differs
💸 Tax Implications: Paying taxes now versus later
🔓 Income Flexibility: Why Roth 401(k)s don’t have income limits
🚀 Maximizing Contributions: Using catch-up rules and additional accounts
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
A Pension Tradeoff Too Many People Underestimate
2026/02/12
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/
📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
One of the biggest retirement decisions most people make has nothing to do with the stock market. It’s a choice buried deep in pension paperwork, and once it’s made, it’s usually permanent. In this episode, Ryan walks through a common pension tradeoff that many retirees underestimate until it’s too late. When you clearly understand the balance between income, longevity, and protection, the right decision often becomes much easier to see.
Here’s what we discuss in this episode:
📄 The Pension Tradeoff: Choosing between higher monthly income or long-term protection
⏳ Longevity Risk: How life expectancy quietly changes the math
💔 Surviving Spouse Planning: Why income needs don’t drop as much as people assume
💰 Income Sources: How Social Security, investments, and insurance factor in
🧠 Income vs. Peace of Mind: Deciding what kind of security matters most
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
10 Retirement Myths Too Many People Still Believe
2026/02/05
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/
📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
There’s no shortage of retirement advice, but not all of it holds up in real life. Many widely accepted beliefs sound reasonable on the surface yet quietly undermine long-term security when tested by market volatility, taxes, health changes, or longevity. Today, Ryan exposes ten retirement myths that continue to trip people up and gives tips for how to have fewer surprises and more confidence when making decisions.
Here’s what we discuss in this episode:
📜 Estate Planning Basics: Why a will alone often falls short
💸 Spousal Income Reality: Don’t expect expenses to drop in half
📊 Investment Strategy Shifts: Rethinking stocks, bonds, and timing
🏷️ Tax Bracket Myths: Why retirement taxes stay stubborn
⏳ Working Longer Assumptions: Why it’s a risky fallback
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
Pros & Cons of the New Trump Savings Accounts for Kids
2026/01/29
📅 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 new government-backed savings account for kids is coming, and on the surface, it sounds like a no-brainer. Ryan shares his take on what these new accounts really offer, and what you need to consider if you choose to utilize it. The money is real, but so are the limitations, and whether it’s worth it depends on your goals, your flexibility, and what you’re already doing.
Here’s what we discuss in this episode:
💵 The Free Money: Government contributions and why that part is appealing
⚖️ Hidden Trade-Offs: Taxes, withdrawal rules, and flexibility concerns
🧾 Paperwork & Complexity: Extra forms, administration, and logistics
🧠 Better Alternatives?: How Trump Accounts compare to 529s, custodial accounts, and other strategies
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
Do I Have Too Much Cash in the Bank?
2026/01/22
📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/
📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html
Having a large cash balance can feel reassuring, but it can also raise questions about missed opportunities. Ryan tackles a common concern: whether holding a significant amount of money in the bank is smart planning or unnecessary caution. Turns out, the answer depends on more than just the number in your account. Tune in to find out how cash fits into your overall plan.
Here’s what we discuss in this episode:
💵 Cash Balance – Evaluating how much liquidity you really need
🎯 Purpose of Cash – Emergency funds versus idle money
⚖️ Personal Factors – Job security, lifestyle, and stage of life
🧠 Planning Perspective – Aligning cash with long-term goals
🤝 Professional Insight – When outside guidance adds clarity
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
I’m 62: Should I File For Social Security Or Wait?
2026/01/15
📅 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 ready to make a move that could impact your finances for decades to come? Join Ryan as he reveals what really goes into deciding the best time to claim Social Security, especially as age 62 approaches. Discover why picking the right strategy, not just a date, can make all the difference in your retirement journey. Don’t let a quick decision today shape your tomorrow.
Here’s what we discuss in this episode:
🕒 Age 62 Decision: What really changes when filing becomes available
🤔 Why People File Early: Fear, cash flow needs, and peace of mind
⏳ Waiting Pays Off: How full retirement age can shift outcomes
📈 Early-Claim Strategies: Smart options if you don’t need the income
🧩 Planning Process: How decisions are tested at Black Oak Asset Management
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
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