Perfect Game Retirement

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The kids might be heading back to school, but today it’s your turn to take a pop quiz—on retirement planning. In this episode, Ryan puts us to the test on five essential financial questions every retiree and pre-retiree should know. So, let’s test your knowledge with a quick finan...

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Just because something used to be true doesn’t mean it still is, especially in retirement planning. In 2025, rising interest rates, tax uncertainty, and longer retirements mean it’s time to rethink some of the old advice. These seven assumptions sound smart at first… but they cou...

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Cue the mixtape of Nirvana, Madonna, and Prince… Gen X, it’s your turn to get ready for retirement. And the stakes are high. You were the first 401(k) generation, hit by two major market crashes, and now you’re entering retirement with more financial uncertainty than the Boomers ...

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Big tax law changes always bring big rumors. But before you assume Social Security is now tax-free or that you’re getting a $40K deduction just for breathing, let’s set the record straight on what this new bill didn’t actually do. In this episode, Ryan sets the record straight on...

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A new tax bill has officially passed (you’ve probably heard it mentioned as the “Big Beautiful Bill”). And while most headlines are focused on politics, we’re focused on what it means for your retirement. The choices you make in the next year or two could have a significant impac...

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Markets crash. Taxes shift. Congress waffles on Social Security. You can’t control any of that. And stressing over it won’t help. What will? Focusing on the four things that actually move the needle in retirement. In this episode, Ryan breaks down the key areas where retirees act...

📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/

📦 Grab your FREE Tax-Free Retirement Toolkit:  https://toolkit.blackoakam.com/podcast-toolkit.html 

You’ve worked hard, saved well, and now you’re thinking about giving back—maybe to your kids, your grandkids, or a cause you care about. But should you wait and pass that wealth on later, or give while you’re still around to enjoy the impact? Let’s talk about how to make that de...

📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/

📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html 

The 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just anot...

Target-date funds just passed $4 trillion in assets. They’re now the default investment in many 401(k)s, and millions of Americans are using them without really understanding how they work. So, are they a smart choice… or just the easiest one? These funds promise convenience and automatic adjustments, but with so much riding on a one-size-fits-all solution, it’s worth asking—are they really helping you, or just keeping you on autop...

Graduation season is an exciting milestone, not just for the grads, but for parents and grandparents who have supported them along the way. Today, Ryan wants to share practical ways you can help your graduate make smart financial decisions early, along with actions that could have a lasting impact on their future. Join us as we discuss ways families can pass on more than just good wishes.

Here’s what we discuss in this episode:

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A little hope is good for the soul, but when it comes to retirement planning, wishful thinking can lead to serious financial mistakes. Today, Ryan walks through five common examples of wishful thinking that can quietly damage your retirement and how you can build a plan that protects your future instead of relying on luck.

Here’s what we discuss in this episode:

🏦 The myth of living off interest alone

📉 Why future tax rates might...

Today we’re talking about Type A personalities. If you’re driven, competitive, and goal-oriented, then you’re part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, and fix the problem. But in investing, that instinct can sometimes backfire. In this episode, Ryan explores how Type A investors can unintentionally sabotage their own success by overreacting to...

Most people believe financial success comes down to numbers, but the truth is your emotions and mindset may play an even bigger role than any spreadsheet ever could. In this episode, Ryan unpacks key lessons from Morgan Housel’s best-selling book The Psychology of Money, revealing how behavior, beliefs, and background shape our financial choices.

Here’s what we discuss in this episode:

🧠 Why no one’s crazy when it comes to money

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Ever wonder what other people talk about with their financial advisors? A new survey of nearly 400 experienced advisors reveals the biggest concerns, challenges, and financial goals their clients are facing today. From retirement planning to working longer than expected, Ryan’s breaking down the key takeaways and how they compare to what he sees in his own client conversations. We’ll also uncover the #1 concern advisors have, a sur...

Got an old 401(k) collecting dust after a job change? You're not alone, and what you do with that account might have a big impact on your long-term financial health. In this episode, Ryan answers a listener’s question about whether it’s okay to leave your 401(k) where it is, or if you’re better off rolling it over. Spoiler alert: the answer isn’t one-size-fits-all, but there are some key pros and cons you need to know.

Here’s what ...

When it comes to retirement planning, it's often the threats you don't see coming that do the most damage. In this episode, Ryan uncovers five silent "assassins" that can quietly erode your financial future, including market crashes, inflation and some surprises along the way! More importantly, he explains how proper planning can defend your wealth against these hidden risks.

Here’s what we discuss in this episode:

📉 How market cr...

The headlines are loud, the markets are messy, and your gut might be telling you to do something - anything -right now. But what should you actually do when your portfolio takes a hit? In this episode, Ryan walks through the four key questions every investor should ask during a downturn, offering clear and practical steps to block out the noise and get some clarity on today’s market situation. 

Here’s what we discuss in this epis...

The Masters is a beautiful reminder of just how much strategy, patience, and long-term focus goes into a great round of golf. Turns out, retirement works a lot like the game. Today, Ryan is teeing up a few key lessons from the course and how they translate into smarter planning for your financial future.

Here’s what we discuss in this episode:

⛳ Why chasing a “hole-in-one” rarely pays off

📆 Why timing matters more than you think i...

Tax season is here, but filing your 2024 return is just one piece of the puzzle. Now is also the perfect time to take advantage of new tax rules for 2025 before the year gets away from you. With higher standard deductions, increased retirement contribution limits, and updated HSA rules, there are plenty of opportunities to potentially lower your tax bill and boost your savings. In this episode, we’ll break down the key changes and ...