A Wiser Retirement®

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...

In this episode of the A Wiser Retirement® Podcast , Shawna Theriault, CFP®, CPA, CDFA®, and Estate Planning Attorney Arun Gupta discuss a real-life story that shows how one overlooked detail can lead to heartbreaking consequences for a family. Related Podcast Episodes:  Ep 295: What Happens If You Die Without a Will? The Legal Nightmare Ep 279: What Should Parents of Children with Disabilities Kn...

In this episode of A Wiser Retirement® Podcast , we are tackling the tough, but essential topic of helping your parents plan financially for the years ahead. As more Americans find themselves supporting both their children and their parents, it’s never been more important to plan ahead, start the right conversations, and protect your family’s financial future. Related Podcast Episodes:  Ep 189: Ta...

In this episode of A Wiser Retirement® Podcast , Casey Smith sat down with Robert Swarthout, Founder & CEO of Teton Crypto Capital , to revisit the cryptocurrency questions they first tackled in 2020 and how the answers have evolved over time. Their answers are here to help you find out, does crypto belong in your portfolio? Related Podcast Episodes:  Ep 14. Are Digital Currencies Right For Yo...

In this episode of the A Wiser Retirement® Podcast , Shawna Theriault, CFP®, CPA, CDFA®, and William Medcalf, CFP® discuss how year-end is the perfect time to be strategic with charitable giving. They explore smarter ways to give, instead of just writing a check, to reduce your tax burden.  Related Podcast Episodes:  Ep 307: Unlocking the Power of Trusts: 10 Different Trusts & How to Use Them...

In this episode of A Wiser Retirement® Podcast , Casey Smith and Travel Advisor Amy Rambo with Blue Pineapple Travel cover how to build a travel line item into your retirement plan, stretch your budget with timing and seat strategies, stay protected with insurance, and tailor trips to your pace and mobility. Related Podcast Episodes:  Ep 294: How Smart Financial Planning Led to Living on a Catamar...

In this episode of A Wiser Retirement® Podcast, Casey Smith, President of Wiser Wealth Management and former airline pilot is with Grace Kennedy, Financial Planning Associate to discuss the unique financial needs of pilots and the smartest financial planning path for them.  Airline pilots face a unique mix of high-but-variable income, mandatory retirement at 65, stringent medical requirements, and...

In this episode of A Wiser Retirement® Podcast , Casey Smith, and Financial Advisor Michaela Dowdy dive into how retirement planning isn’t just about matching today’s income with today’s expenses. It’s about preparing for the future value of money. Related Podcast Episodes: Ep 245. Strategies for Early Retirement and Long-Term Security Ep 212. Medical Costs During Retirement and Preparing for the...

In this episode of the A Wiser Retirement® Podcast , Estate Planning Attorney Arun Gupta joins Shawna Theriault, CFP®, CPA, CDFA® to demystify trusts, what they are, who they’re for, and how 10 common trust types work in real life. Related Podcast Episodes:  Ep 295: What Happens If You Die Without a Will? The Legal Nightmare Ep 279: What Should Parents of Children with Disabilities Know About Esta...

In this episode of A Wiser Retirement® Podcast , Casey Smith is joined by Robert Swarthout, CEO and Portfolio Manager of Teton Crypto Capital . Together, they dive into the latest crypto news, from the launch of new ETFs to the growing influence of stablecoins in U.S. Treasuries. The conversation explores how these developments could impact retirement planning and whether crypto deserves a place i...

In this episode of A Wiser Retirement® Podcast , Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®  is joined by Financial Advisor William Medcalf, CFP® to discuss the financial implications of moving across state lines, and how a change in location can also mean major changes to your financial life. Related Podcast Episodes: - Ep 77: Tips for Moving to Lower Tax States - Ep 274: Buying...

In this episode of A Wiser Retirement® Podcast , Casey Smith and William Medcalf, CFP® dive into what it really means to be “quietly rich” and how smart habits, not flashy spending lay the foundation for financial independence. Related Podcast Episodes: - Ep 73: Leave a Legacy of Generosity - Ep 260: 10 Financial Habits That Lead to Long Term Success Related YouTube Videos: - Pitfalls of Living Ri...

In this episode of A Wiser Retirement® Podcast , we discuss the importance of commercial airline pilot medical disability planning and why it’s often overlooked compared to life insurance. We explain how airline disability benefits work, the differences between short-term and long-term coverage, and why “own occupation” policies are essential. The conversation also covers supplemental insurance op...

Retirement isn’t just a finish line, it’s a brand new chapter. In this episode of A Wiser Retirement® Podcast , Casey Smith and Financial Advisor Michaela Dowdy outline eight key things you should focus on starting five years before retirement. While more time is always better, the 3–5 year mark is when many people get serious. Here's how to make the most of it. Related Podcast Episodes: - Ep...

In this episode of the A Wiser Retirement® Podcast , Casey Smith sits down with Robert Swarthout, founder and CEO of Teton Crypto Capital , to discuss how fast cryptocurrency is evolving and how banks are getting involved. - Ep 296: Crypto Update: Big Beautiful Bill, GENIUS Act, & Crypto Company IPOs - Ep 286: How can I evaluate crypto as a potential investment? Learn More: Founded in 2001, Wi...

In this episode of  A Wiser Retirement® Podcast , we celebrate hitting a major milestone, 300 episodes! In this special episode, President Casey Smith and Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®, reflect on the history of Wiser Wealth Management, the growth of the podcast, and the firm’s mission to provide real, relationship-driven financial planning. Related Podcast Episodes:...

In this episode of  A Wiser Retirement® Podcast , Shawna Theriault, CFP®, CPA, CDFA® and Financial Advisor Michaela Dowdy dive into the essential financial conversations couples should have before saying “I do.” From discussing mindsets and money habits to navigating joint goals and future planning, they offer guidance on how to build a healthy financial foundation for marriage. Related Podcast Ep...