Dollars & Common Sense

This episode focuses on one of the most challenging transitions in retirement: moving from steady paychecks to generating income from savings. It explores why the loss of a predictable paycheck creates stress even for retirees with substantial assets, and how that stress is often rooted in uncertainty rather than investment performance alone. The conversation breaks down key risks such as sequence of returns, emotional reactions to market volatility, and the mindset shift required to move from saving to spending. Listeners are guided through building reliable income layers using Social Security, pensions, and sustainable portfolio withdrawals to create structure and predictability. The show also emphasizes flexibility as a built in safety valve, highlighting how thoughtful income planning can reduce anxiety, increase confidence, and replace paychecks without replacing peace of mind.

In this episode, we define the Retirement Red Zone—the five years before and after retirement—when financial decisions become larger, more permanent, and far less forgiving. We walk through the five critical choices that can make or break retirement: when to claim Social Security, how to turn savings into reliable income, managing taxes and RMDs, preparing for healthcare and longevity risk, and ensuring control and continuity if life interrupts the plan. The central message is clear: retirement success is driven less by chasing performance and more by coordination across income, taxes, healthcare, and family decisions. If you’re approaching retirement—or already there—this episode offers a structured framework to avoid costly missteps and replace uncertainty with clarity and confidence.

Most DIY investors don’t have an investing problem—they have a behavior problem, and this episode proves it with hard numbers: over the last 10 years, the average investor trailed the S&P 500 by about 3.3% per year, and even over 20 years they lagged by roughly 1.1% per year. We break down the 10 most common mistakes—from panic-selling and market timing to performance chasing, poor diversification, and treating investing like entertainment. Then we lay out an “advisor-like” improvement plan you can implement immediately: a one-page investing rulebook, automation, and a simple rebalancing system designed to keep emotions from hijacking results. We wrap with practical guidance for listeners who decide they want professional help, including what to look for in a fiduciary CFP® at a Registered Investment Advisor.

Kick off the new year with a simple game plan that can make the rest of 2026 feel calmer, clearer, and more in control. In this episode, we break down practical “do-it-this-week” moves—tightening up cash flow, building an emergency cushion, and setting your retirement savings on autopilot—without the jargon or technicalities. We’ll also share a quick 2025 market performance recap (including small-cap, international, and emerging markets) and highlight key 2026 updates like retirement contribution limits and important tax changes to know. If you’ve been waiting for a fresh start, this is it: small steps now can create big momentum all year long.

Get your money ready for the new year with this special year-end checklist episode. We’ll walk through the key moves to think about before December 31—like tidying up your investments, checking on taxes, and making smart retirement contributions. You’ll also hear ideas for reviewing benefits, insurance, and your “big picture” plan so you start 2026 on solid footing. And since it’s the holidays, we’ll talk about thoughtful gifting and simple family money conversations that can bring everyone onto the same page.

As the year wraps up, Kevin walks through a checklist of smart money moves to consider before December 31st. He talks about checking your investment gains and losses, making any required IRA withdrawals, and deciding whether to add more to your retirement accounts before the deadline. The show also highlights chances to use HSAs and flexible spending accounts, and to double-check 529 college savings and other big upcoming expenses. Kevin touches on insurance and healthcare items that reset in the new year, so you don’t leave benefits on the table.

This episode explores how to give meaningfully and strategically—whether to loved ones or charitable causes. It breaks down the full spectrum of gifting options, from cash and collectibles to donor-advised funds and charitable trusts, while explaining the powerful tax benefits of thoughtful giving. Listeners will learn how to maximize their impact, avoid common pitfalls, and align their generosity with their personal values. It’s a practical, feel-good guide to making every dollar you give this season count—for both you and the people or causes you care about most.

This episode explores how to enjoy your money guilt-free while still achieving long-term financial freedom. It covers why people often overspend or underplan for travel and hobbies, and how to shift toward intentional, values-based spending that maximizes joy. Listeners will learn practical ways to allocate funds, use dedicated accounts, and balance flexibility with discipline. Real-life examples show how thoughtful planning turns money into a tool for meaningful experiences—without sacrificing security or peace of mind.

This episode explores why even high earners often struggle to build wealth as their income rises. It explains how lifestyle upgrades—bigger homes, newer cars, and pricier vacations—quietly erode savings and financial security. Through relatable examples and data, the discussion uncovers the psychology behind lifestyle creep and its long-term costs. Listeners will learn how to spot warning signs in their own finances and adopt simple, practical strategies to stay grounded, save more, and achieve lasting financial freedom.

Reverse mortgages have come a long way since their inception in the 1960's. Today, they represent a flexible financial planning tool to help manage cashflow and get liquidity from an otherwise illiquid asset.

It seems anyone with a smart phone and a TikTok account can dispense financial advice these days. Unfortunately, a lot of what you hear online is wrong. In this episode, we expose common types of financial misinformation, why it's harmful, and how you can spot dubious claims.

A continuation of the July 22nd show relating to the proper use of insurance in financial planning. We discuss the correct purpose of insurance, the different types that are prudent for a family to carry, and ways you can lower your premium while still having solid coverage.

Insurance premiums are one of the largest household expenses after taxes. In this episode, we discuss the correct purpose of insurance, the different types that are prudent for a family to carry, and ways you can lower your premium while still having rock-solid coverage.

This episode explores the softer side of retirement planning that many people don't fully consider. Transitioning from daily work to retirement can bring changes to one's identity and purpose, social connections, mental and emotional health, lifestyle and routine, and spousal relationship dynamics. We discuss many of the benefits -- and pitfalls -- we've learned through professional experience.

An estate plan is not something you do for yourself. It's something you do for your loved ones. But a well-crafted estate plan is an important component of a comprehensive financial plan. This is an easy to understand discussion of wills, trusts, and powers of attorney that make up the estate plan, as well as the purpose and role of the executor, grantor, trustee, and beneficiary.

Financial scams through the ages. How they have evolved, ways you can protect yourself, and where to report fraud when they occur.

A discussion of the deep psychological feelings and emotions that money evokes. This includes strategies and applications to help overcome negative biases and take advantage of the positive vibes.

Financial conflict is often sited as one of the main reasons for divorce in the United States. In this show, we tackle the highly sensitive topic of combining finances during marriage. We discuss the best way to set up bank accounts, how to develop a shared budget, how to treat income/debt disparities, how to plan long-term goals together, and more.

What is behind one of the fastest and sharpest drops of the US stock market, putting the decline in historical context, and investment actions you should take now.

Most people who work with a financial advisor don't have a comprehensive list of specific financial goals. That's ok. A good financial advisor will help draw those goals out of you and incorporate them into the planning process. Here, we discuss many of those common financial goals to help stimulate your thoughts and give you some ideas you can use.