Dollars With Dennis

Some of the most important retirement questions have very little to do with money. What will an ordinary Tuesday look like? What worries would you erase if you could? What would you do if money were no longer a concern? In this episode, Ryan walks through five questions designed to uncover purpose, priorities, regrets, and bucket-list goals so the financial plan can be built around the life someon...

This episode tackles one of the biggest retirement questions: “When can I actually retire?” Dennis explains why the answer depends on far more than reaching a certain age or account balance, with healthcare costs, spending needs, Social Security timing, income sources, and even the emotional transition away from a paycheck all playing a role. Here’s some of what we discuss in this episode: 📅 No M...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Retirement in 2026 comes with some realities that previous generations didn’t face in quite the same way. In this episode, Dennis breaks down five major factors that can reshape a retirement plan, from longer lifespans and rising healthcare costs to inflation, active lifestyles, and fi...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/   Somewhere in a drawer, a filing cabinet, or a shoebox in the closet, most of us are holding onto financial paperwork we don't actually need. And we’re probably missing a few things we do need. Ryan sorts out what stays, what goes, and where it all belongs. Nobody loves paperwork...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/   More people in their 60s and 70s are staying on the job than ever before, and it's not always about the money. Ryan digs into the real reasons retirees keep showing up to work. Working longer isn't automatically the wrong call. Sometimes it's exactly right. The real qu...

Today, Dennis walks through a potential retirement story in chapters. As each new detail comes in, we're going to react to it the way a financial advisor would in a real-time meeting. Ron's 64, figured a lot of this out on his own, and this is his first time sitting down with a professional. Let's see what we find and what we might do differently from here. Ron always figured he&apo...

Many people plan to retire around 65, but new research shows a large percentage are leaving the workforce several years earlier and often not by choice. Health problems, job loss, and rising healthcare expenses can suddenly force a retirement timeline to change. In this episode, Dennis explains why those extra few years matter so much and how better planning can make an unexpected early retirement...

Discover the hidden pain points that can quietly undermine your retirement confidence. Join guest host Ryan Hoover as he explores the emotional roadblocks that often surface during the transition and explains why they can be just as important as the numbers. Stay tuned to see which of these concerns might be holding you back, and what you can do about them before they become bigger problems. Here’...

Your finances touch nearly every part of your life: your family, your goals, your fears, your values. So finding an advisor isn't just about finding someone who knows the most about finances. It's about finding someone you actually trust. Today, Dennis talks about what that looks like in practice. These are the real signs that an advisor relationship is working. If that's not what y...

According to a recent Kiplinger article, there are five keys to a retirement plan that hold up over time. They all happen to start with the same letter — which either means it's a great framework or someone really wanted it to work out that way. In this episode, advisor guest host Ryan Hoover joins the show to walk through the “5 D’s” of retirement planning and how each one plays a role in he...

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,...