Perfect Game Retirement

My Investments Underperformed the Market - Should I Fire My Advisor?

It’s a question a lot of people ask at some point: if your investments aren’t keeping up with “the market,” is it time to move on? Ryan breaks down what you’re actually comparing against, why that comparison can be misleading, and what really matters when evaluating performance. The right benchmark isn’t the market, it’s your plan.
Here’s what we discuss in this episode:
📊 Wrong Benchmark: S&P 500 isn’t always the right comparison
⚖️ Consistency Matters: Stable returns beat big swings in retirement
⏳ 1-Year Noise: Short-term performance can mislead
⚠️ True Red Flags: Long-term lag + no adjustments
📉 Risk Alignment: Returns must match your comfort level
 
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

A New Proposal Might Cap Your Social Security Payments

A new proposal out of Washington is adding a fresh angle to the Social Security conversation, and Ryan is breaking down what it could mean. He walks through what’s being discussed, who it might impact, and how it fits into the bigger picture of Social Security’s future. The details may change, but the reality is this: something will eventually have to give. Understanding the possibilities now can help you make better decisions later.
Here’s what we discuss in this episode:
💰 New Proposal: Cap benefits based on income
📉 Benefit Limits: $100K couples, $50K individuals
📊 Who’s Impacted: Higher earners are most affected
⚠️ System Pressure: Fewer workers supporting more retirees (clear warning)
📈 Plan Ahead: Model multiple Social Security scenarios
 
Find out your benefits estimate: www.ssa.gov
 
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

Why Spending in Retirement Is Harder Than It Sounds

📅 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?

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?

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

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

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?

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?

📅 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

📅 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