Dollars With Dennis

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,...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Turning 62 unlocks Social Security, but deciding when to file is one of the biggest income decisions you’ll make in retirement. Find out why some people claim early, why others wait, and how fear, health, and lifestyle goals often shape the decision more than math alone. If you want a...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Nothing will mess with your financial confidence faster than comparing your savings to someone else’s highlight reel. Whether it’s a sibling, a coworker, or a YouTuber who claims they retired at 35, comparison can make even solid savers feel behind. Today, Dennis shares what really mat...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ A lot happened in 2025: big political swings, stubborn inflation, new tax rules, and even a historic government shutdown. But headlines alone don’t determine your retirement outcomes. In this episode, Dennis reveals the biggest financial events of the year and explains what actually ma...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ You’ve heard of Baby’s First Christmas, but what about Retiree’s First Christmas? Your first holiday season after leaving the workforce is a milestone all on its own. The schedule, the spending, the traditions… everything feels a little different. In this episode, Dennis talks about wh...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ The smartest retirees all have one thing in common… they know how to ask better questions. In this episode, Dennis breaks down how the wording, focus, and intent behind your questions can completely change the quality of your retirement decisions. We reveal the usual questions people a...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ How do you know when a financial advisor just isn’t the right fit? In this episode, we break down five of the biggest red flags people overlook when choosing or evaluating an advisor. Dennis explains why advisor stability matters, the dangers of “one-size-fits-all” planning, and how a...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Getting married later in life means you’re combining lives but not necessarily combining finances. How do you build a retirement plan together when you’ve both already built your own?  Dennis answers a listener’s question about navigating financial and emotional security in later-life...

Giving Tuesday (Dec 2, 2025) and year-end donations are right around the corner. But before you hit that “donate” button, let’s talk about how to give with both your heart and your head, because generosity feels even better when it’s part of a plan. Dennis breaks down the “why, when, how much, and what” of charitable giving and how to make your generosity meaningful, strategic, and tax-efficient....

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Is having more than one financial advisor a smart move or a recipe for confusion? Today, Dennis breaks down the motivations behind splitting assets between multiple experts and highlights the common pitfalls of this approach. You’ll also hear about why consolidating with one trusted ad...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Fidelity just released their 2025 Retiree Health Care Cost Estimate, and the number is staggering: $172,500 for a 65-year-old retiring today. The bigger problem? One in five Americans haven’t even thought about health care costs in retirement. Dennis breaks down what this means, why it...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ According to recent surveys, the emotional and financial burden of paying for college often exceeds expectations. In this episode, Dennis unpacks the tough trade-offs parents face when trying to help their kids through school without sacrificing their own future. College is a huge inve...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ After years of being overlooked, bonds are back in the spotlight, and investors want to know if now’s the time to buy. Dennis breaks down how bonds really work, what’s driving today’s yields, and why they might deserve a bigger role in your portfolio. Bonds can provide income, balance,...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ According to recent surveys, the emotional and financial burden of paying for college often exceeds expectations. In this episode, Dennis unpacks the tough trade-offs parents face when trying to help their kids through school without sacrificing their own future. He also shares practic...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Well, you’re retired. Now what? Some people subscribe to the “first year rule,” which says that the majority of your best retirement months will take place in the first year. So how can you be strategic during that time and set the tone in the right way, both emotionally and financiall...

Get your customized planning started today by connecting with Dennis 👉 https://www.faith401kmgmt.com/contact_us/ Downsizing may seem like a quick way to cut costs and simplify life, but rising property taxes, insurance rates, and HOA fees can quickly erase any savings. Is downsizing truly the answer, or does it just bring more complications? Today, we’ll go beyond the financials to explore the em...