The Perfect Game Retirement Podcast is brought to you by Black Oak Asset Management, serving the greater Atlanta area with offices in Alpharetta, Cartersville and Macon. Former professional baseball player and now financial coach, Ryan Ledden, is your host. This is the show that'll help you make the right decisions, so you can pitch a "perfect game" in retirement.

Financial planning isn't really about spreadsheets, rates of return, or chasing the perfect investment strategy. At its core, it's about making sure the people you love are protected if life takes an unexpected turn. Ryan discusses the often-overlooked side of financial planning and shares how to navigate difficult family moments with clarity. Tune in to make sure you're protecting what matters most. Here's what we discuss in this episode: ❤️ Financial Planning Is Personal


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:

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:

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:

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:

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:

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:

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 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 autopilot? In this episode, Ryan explains how target-date funds work, why they've become so popular, and the hidden pitfalls that many investors miss. Here's what we discuss in this episode:

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:

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:

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 market swings. Here's what we discuss in this episode: