Perfect Game Retirement

Financial information has never been more available — TV, podcasts, YouTube, Reddit, and now AI that will answer any question in about three seconds. And yet some of the worst financial decisions we see come from people who did a ton of research first. Today, Ryan’s talking about why this happens and what good research actually looks like. Being informed is a good thing. Being confidently misinfor...

Over the past year, one retirement video on YouTube pulled in 3.7 million views. The title: "Sell These 5 Things Before You Retire." We thought it was worth a conversation, not to tear it apart, but to react honestly. Does Ryan agree? Let's get into it: 3.7 million people watched this video for a reason. It touches something real. Retirement isn't just about what you've accumulated. Sometimes it's...

Risk is unavoidable. The only question is whether the risk you're taking actually makes sense for where you are in life. Today, Ryan looks at three stages of the financial journey, and at each one, we've got three types of people with three very different approaches. Whether you're decades away from retirement or already living it, this conversation will help you think differently about risk and o...

Summer's here. And somewhere between the excitement of planning a big trip and the anxiety of what it costs, a lot of retirees end up doing something that surprises us… they feel guilty about it. They worked hard, saved, planned for decades, and then second-guessed a beach vacation. Today, Ryan talks about how travel fits into a real retirement plan and how to enjoy it without guilt. You didn't sa...

When retirement is around the corner, some of the biggest decisions aren’t about when to retire, they’re about how income continues if one spouse is gone. Ryan walks through a listener question about pension survivor options and why these decisions often become more emotional and permanent than people expect. A thoughtful retirement income strategy can make these choices much easier to navigate do...

Ryan’s doing something a little different today. Three listeners wrote in with variations of the same question, “Am I ready to retire in 2026?” Same question, three very different situations, three very different answers. If retiring in 2026 is on your mind, your version of this question is the one that matters most. And it probably has its own wrinkles, its own gaps, its own version of “almost re...

Spend five minutes on Reddit or YouTube and you’ll find people being brutally honest about what they wish they had done differently with money. Today, Ryan’s pulling from some of those real conversations and breaking down the lessons behind them. The best time to learn any of these lessons was at 25. The second-best time is right now. If you're ready to stop leaving opportunity on the table, let's...

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 mo...

📅 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 done a great job managing your money over the years, but retirement changes the game. Ryan looks at the decision many investors face: should you keep doing it yourself, or bring in a financial advisor? He walks through what actually chan...

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&...

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...

📅 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 shif...

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 he...

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...

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 t...

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 str...

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 thi...

📅 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 be...

📅 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...

📅 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...

📅 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....

📅 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 tra...

📅 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 l...

📅 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 rea...

📅 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...