A Wiser Retirement®

About 70% of Americans feel confident about retiring, but most don’t actually have a plan. Confidence without clarity isn’t confidence at all, it’s hope. In this episode of the A Wiser Retirement® Podcast , we break down how to turn uncertainty into a structured, testable retirement plan, especially if you’re within five years of retiring. Related Podcast Episodes:  Ep 308. The Silent Tax: How Inf...

Passive income is one of the most talked-about wealth-building strategies today, but it’s also one of the most misunderstood. From rental properties to online side hustles, many income streams labeled “passive” actually require far more time, effort, and involvement than people expect. In this episode of the A Wiser Retirement® Podcast ,  we take a closer look at the reality behind passive income,...

Most people don’t actually have a financial plan, they have a scattered collection of accounts, insurance policies, and investments they’ve picked up over time. In this episode of A Wiser Retirement® Podcast , we break down what financial planning actually looks like behind the scenes, and why so many people are missing it entirely. Related Podcast Episodes:  Ep 327. What Tax Planning Strategies S...

Owning property with others, whether it’s a spouse, sibling, friend, or business partner, can seem like a smart financial move. It can reduce costs, create investment opportunities, and simplify certain aspects of ownership. But without proper planning, it can also lead to serious financial and legal complications. In this episode of the A Wiser Retirement® Podcast ,  Shawna Theriault, CFP®, CPA,...

There is a moment many families are not prepared for: when the roles begin to shift. One day, your parents are helping you make big financial decisions, and the next, you are wondering whether they need help managing their own money. It is emotional, uncomfortable, and deeply personal, but it is also one of the most important conversations a family can have. In this episode of A Wiser Retirement®...

Annuities are often marketed as the safe, guaranteed, no-risk answer for retirement income. For many retirees, that promise can sound incredibly appealing, especially during volatile markets or uncertain economic times. But the reality is far more complicated. In this episode of A Wiser Retirement® Podcast , we unpack the truth about annuities, why they are so commonly sold, and why many investors...

More than 70 million Americans receive Social Security benefits every month. For millions of retirees, disabled workers, and surviving family members, that monthly check is a crucial part of their financial stability. But what would actually happen if Social Security suddenly disappeared? In this episode of A Wiser Retirement® Podcast , we break down how Social Security works, why it matters so mu...

Housing affects nearly every part of life, whether you rent, own, invest, or you’re just trying to keep up with rising costs. In this episode of A Wiser Retirement® Podcast , we sit down with Tom Townsend, REALTOR® of Tom Townsend Realty Group to break down the housing trends shaping 2026. Related Podcast Episodes:  Ep 267. The 2025 Housing Market: Trends, Changes, and What to Expect Ep 198. Real...

Crypto is becoming a bigger part of retirement conversations, but how does it actually fit into a coordinated tax and estate strategy? In this episode of A Wiser Retirement® Podcast , we break down how to thoughtfully integrate crypto into a diversified retirement plan without derailing your long-term goals. Related Podcast Episodes:  Ep 326. Why Crypto Still Confuses Investors Ep 306. Crypto in Y...

A lot of entrepreneurs start a business for the same reason: freedom. Freedom to set their schedule, choose their clients, and build something meaningful. But for many owners, the reality flips suddenly the business can’t function without them, and the very thing they built to create flexibility becomes the reason they feel trapped. In this episode of A Wiser Retirement® Podcast , we sit down with...

In today’s world, much of our financial, personal, and sentimental lives live online. From bank accounts and crypto wallets to photos, emails, and social media profiles, your digital assets don’t disappear when you’re gone. If they’re not planned for, they can create confusion, stress, and even permanent loss for your loved ones. In this episode of the A Wiser Retirement® Podcast ,  Shawna Theriau...

Airline pilots love to debate (and sometimes complain about) unions, but do pilot unions actually make pilots “richer”? In this episode of A Wiser Retirement® Podcast , we break down what unions really change, what they don’t, and why the answer depends on how you define “richer.” Related Podcast Episodes:  Ep 259. What Pilots (& Others) Should Consider 5 Years Before Mandatory Retirement Ep 2...

As a new tax year begins, it brings important updates that can significantly impact your retirement and tax strategy. On this episode of the A Wiser Retirement® Podcast , we break down what’s changing in 2026, what’s staying the same, and how to make smarter decisions early in the year, before opportunities slip away. Related Podcast Episodes:  Ep 86. Important things to Know About Taxes Ep 262. O...

Crypto continues to be one of the most misunderstood areas of investing. In this episode of A Wiser Retirement® Podcast , we sit down with Robert Swarthout, Founder and CEO of Teton Crypto Capital , to unpack why crypto still feels confusing, what problems it’s actually trying to solve, and how regulation could shape its future. Related Podcast Episodes:  Ep 312. Is Crypto Right for You? Ep 306. C...

If someone called you today claiming your bank account was hacked, would you know exactly how to respond? In this episode of A Wiser Retirement® Podcast , we dive into the latest financial scams, how they work, and most importantly, how to protect yourself and your loved ones before real damage is done. Related Podcast Episodes:  95. ESG: Scam or Saving the World? Related Financial Education Video...

Families navigating a special needs diagnosis often find themselves overwhelmed, emotional, and unsure where to begin. In this episode of A Wiser Retirement® Podcast , Casey Smith sits down with Meaghan Timko, Founder of Parallel and COO of Gradual Behavioral Health , to unpack what thoughtful, proactive planning really looks like for families supporting children with special needs. Related Podcas...

In this episode of A Wiser Retirement® Podcast , we break down what really drove the market’s double-digit gains in 2025, from AI winners to international outperformance. We also explore what may or may not repeat in 2026 and what investors should be paying attention to now. Related Podcast Episodes:  Ep 201. 2023 Market Recap and 2024 Market Predictions Ep 261. 2025 Market Outlook: Navigating the...

It’s bonus season for airline pilots, and while profit-sharing payouts can be substantial, they can also disappear just as quickly without a plan. In this episode of A Wiser Retirement® Podcast , we break down how pilot bonus programs work and more importantly, how to turn those bonuses into long-term wealth instead of short-term spending. Related Podcast Episodes:  Ep 317. Pilots Start Here Ep 30...

It’s January 5th. Your financial app chirps, “You’re on the best financial track ever!” Do you believe it? Probably not, because we’ve all seen New Year’s momentum fade fast. On this episode of the A Wiser Retirement® Podcast , we lay out 10 practical financial resolutions that are designed to actually stick, ordered from quick wins to long-term payoffs. Related Podcast Episodes:  Ep 238. Is Insta...

A new year is a natural reset button and a perfect time to get intentional about money. On this episode of the A Wiser Retirement® Podcast , we share how most Americans enter the year with at least one financial priority. The biggest themes are consistent: reducing debt, saving for major purchases, and planning for retirement. But turning those priorities into real progress takes more than vague r...

Early retirement is a dream for a lot of people and it can be possible, but only if you plan for it the right way. On this episode of the A Wiser Retirement® Podcast , the conversation tackles what early retirement really means, why so many retirees run out of money, and what steps you can take now to retire sooner without sacrificing long-term security. Related Podcast Episodes:  Ep 273: How Earl...

If something unexpected happened tomorrow, who would make decisions for you? That’s the big question at the heart of this episode of the A Wiser Retirement® Podcast , where Shawna Theriault, CFP®, CPA, CDFA®, and Estate Planning Attorney Arun Gupta demystify what is a power of attorney and explain why nearly everyone needs them. Related Podcast Episodes:  Ep 279: What Should Parents of Children wi...

On this episode of the A Wiser Retirement® Podcast , Grace Kennedy interviews Casey Smith, president of Wiser Wealth Management and former airline pilot, on how aviators can prioritize, plan, and protect their money from day one through retirement. Related Podcast Episodes:  Ep 194: Delta, American & United: Who's Got the Best Pilot Retirement Offering? Ep 173: Making the Most of Your Air...

Whiskey gifting is an art and in 2025, it’s easier (and tastier) than ever to give the perfect bottle. On this special non-financial episode of the A Wiser Retirement® Podcast , host Casey Smith sits down with whiskey enthusiast Robert Swarthout to talk all things bourbon, barrel picks, and what makes this year’s selections so special. Prices are moderating, access is improving, and distillers are...

In this episode of A Wiser Retirement® Podcast , we discuss how $1 million has been the golden benchmark for retirement savings. But is this magic number still enough in today's economy? Related Podcast Episodes:  Ep 276: How to Make Sure You're Ready for Retirement Ep 217: What are the best and worst states to retire to? Related Financial Education Videos: Investing for Income vs Growth...