Dollars With Dennis

Dave Ramsey has built one of the most recognized brands in personal finance. Millions of people have followed his advice out of debt and into savings. But when it comes to how much you should pull from your retirement accounts each year, Ramsey takes a position that some financial professionals find hard to get behind. Today, we break it down: what Dave says, what the research says, and what Denni...

The right investment strategy isn't determined by your age alone, it's determined by where you are in life, what you're trying to accomplish, and how much uncertainty you're willing to accept along the way. Dennis explores how financial priorities evolve and why a successful plan requires balancing growth, protection, and flexibility through every stage of the journey.  Here’s...

Today we're trying something a little different. Dennis walks through a real retirement story in chapters — and as each new detail comes in, we're going to react to it the way a financial advisor would. Fran is 62, she figured a lot of this out on her own, and she's only now sitting down with a professional for the first time. Let's see what we find and what we might do differe...

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, they saved, they planned for decades, and then they second-guess a beach vacation. Today, Dennis talks about how travel fits into a real retirement plan and how to enjoy it without...

It's summer and nothing says summer quite like Tom Cruise as Maverick soaring across the sky in Top Gun. This year marks the 40th anniversary of the original film, and with Tom Cruise's birthday on July 3rd, Dennis figured it was the perfect excuse to revisit some of the most iconic quotes from the franchise and see what they have to say about your financial life. Because Maverick didn&a...

Step into Triple Crown season as Dennis uses the excitement of the Kentucky Derby to reveal what it really takes to build a winning retirement plan. He draws parallels between horse racing and financial planning, including how to avoid “long shot” bets with your nest egg. Grab your saddle and your fancy hat and join us at the starting gate as we race toward retirement. Here’s some of what we discu...

If you want unfiltered financial advice, don’t just read a book — scroll the comments. 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, Dennis’ son Parker is joining us and talking through the biggest young money mistakes. Most of these regrets don’t come from bad intentions. They come from small...

Delayed gratification is a difficult skill to master, and that’s just as true with financial matters as it is in other areas of your life. Let’s talk about some instances where you might be faced with a choice of being satisfied now or satisfied later. Today, we’ve got a special guest, Parker (Dennis’ son), joining the conversation to share his perspective on making smart money choices early on.  ...

Retirement often looks perfect on paper—travel, freedom, and finally enjoying life on your terms. But for many people, the reality doesn’t match the picture they had in mind. Dennis takes a closer look at the gap between expectation and reality in retirement and reveals how having a well-thought-out plan matters more than ever. Life is going to throw curveballs, but a plan unique to you will help...

Most people meet with their financial advisor once a year, but that meeting can either move your plan forward or waste your time. Dennis breaks down what separates a meaningful review from one that just feels like a presentation. It’s a chance to reset, ask better questions, and actually engage with your plan. The difference comes down to how you show up and what you expect from it. Here’s some of...

In honor of National Volunteer Week, this episode takes a different angle on retirement, one that has nothing to do with markets or returns. Retirement isn’t just about stepping away from work, it’s about stepping into something meaningful with the time and freedom you’ve earned. Dennis walks through how giving back can play a powerful role in shaping a more fulfilling next chapter. Because the im...

Today we’re talking about what to do when things go right, whether it’s a windfall, a surprise, or an unexpected financial event. Because good fortune without a plan can unravel faster than you'd expect. Dennis covers five situations that might look like pure luck from the outside but shows you exactly what needs to happen next to protect yourself. The people who make the most of good fortune...

For many retirees, the hardest part isn’t saving, it's learning how to spend the money they’ve worked so hard to accumulate. After decades of saving and living on a paycheck, the shift to spending can feel almost unnatural. In this episode, Dennis talks about why this happens, how it affects people’s retirement plans, and the strategies that can help people feel comfortable spending their ret...

A listener recently made a career move that looks great on paper, but it raised a real concern: can a retirement strategy actually keep up when income becomes unpredictable? Commission checks, bonuses, and variable pay structures introduce a level of uncertainty that can make saving feel inconsistent or even risky. Dennis shares how retirement savings can still thrive with variable income, but we...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ The closer you get to retirement, the more complicated decisions about life insurance become. Dennis walks through the key differences between each type of coverage and explains how your needs shift as you move through your 50s and beyond. The real question isn’t which policy is “best,...

AI is everywhere and for many people approaching retirement, it’s raising some serious questions. Today, Dennis goes through the top AI-related Google searches from people in their 50s and 60s and sharing his input. The search bar doesn't lie. People are nervous, curious, and trying to figure out what AI means for the life they've spent decades building. Most of the answers are less dram...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ AI headlines are everywhere right now: “jobs disappearing,” “work becoming optional,” and predictions that artificial intelligence will reshape the entire economy. Dennis steps back from emotional headlines and looks at what the actual data suggests about AI and the workforce. The real...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ For many business owners, retirement isn’t sitting in a 401(k), it’s tied up in the company itself. The big question is whether one sale can truly fund decades of living expenses. Dennis unpacks what “enough” really means and why relying on a single liquidity event can create unexpecte...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Some people enjoy thunderstorms, while others start boarding up windows at the first dark cloud. Investing works the same way. Dennis explores how personality, emotions, and long-term goals shape financial decisions, especially when markets feel uncertain. If your strategy only works w...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Everyone has an opinion about money, especially the people with microphones, book deals, and streaming specials. Some of that advice can be motivating. Some of it sounds great on stage but gets complicated in real life. Dennis weighs in on several well-known financial personalities and...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Winter can affect more than your mood. It can affect how you see risk, money, and the market. Today, Dennis is talking about why the “winter blues” can make financial decisions feel harder, and how to stay steady when emotions are running low. Winter doesn’t last forever. Neither do em...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ There’s no shortage of financial advice out there, and unfortunately, not all of it is good. Some of the most damaging retirement mistakes don’t come from reckless behavior, but from ideas that sound reasonable and get repeated often enough to feel true. Today, Dennis is busting some o...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/   A new government-backed savings account for kids is coming, and it’s already raising questions. On the surface, Trump Accounts sound appealing, but Dennis takes a closer look at how these accounts work and how they compare to other savings options families already use. Before decidin...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ After a year marked by volatility, uncertainty, and more than a few economic curveballs, it’s understandable if optimism doesn’t come easily. But at least one economist is arguing that the outlook for 2026 may be brighter than many people expect. Today’s video will provide our reaction...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ What’s new in 2026 for retirees and pre-retirees? This year brings several updates that could quietly affect your cash flow, taxes, and savings strategy. Dennis walks through what’s worth paying attention to as 2026 begins- because small changes can have noticeable impacts if ignored,...