Shows / A Wiser Retirement®
A Wiser Retirement®
Ready to take control of your financial future? A Wiser Retirement® Podcast breaks down the strategies, insights, and real-world lessons you need to build lasting wealth and retire with confidence.Each week, we cut through the noise to simplify complex financial topics, covering everything from smart investing and retirement strategies to practical financial planning you can actually use. You’ll hear real success stories and actionable tips designed to help you make informed decisions at every…
Episodes
- A Wiser Retirement®
355. What Are the Best Tax Strategies for High-Income Couples?
Making more money does not automatically mean keeping more of it. For high-income couples, taxes often become more complicated as compensation rises…
- A Wiser Retirement®
354. What Would I Do if the Stock Market Fell 30% Tomorrow?
A 30% stock market decline gets attention quickly. Account balances fall, headlines become more alarming, and investors may feel pressure to make an immediate…
- A Wiser Retirement®
353. Is $2 Million Enough to Retire? What about $3 Million?
Reaching a retirement portfolio of $2 million or $3 million may feel like crossing a definitive finish line. However, an account balance alone does not…
- A Wiser Retirement®
352. Do You Even Need a Budget If You're Already Saving Enough?
The word “budget” often brings to mind complicated spreadsheets, spending guilt, and tracking every coffee purchase. While that level of detail can be helpful…
- A Wiser Retirement®
351. How to Gift Money to Your Kids Without Tax Problems
Giving money to your children can be an incredibly meaningful way to support them while you are still here to see the impact. You may want to help with a home…
- A Wiser Retirement®
350. Can a Pilot Retire at 55? Running the Real Numbers
Many people dream of becoming an airline pilot, while many pilots eventually dream of retiring early. Retiring at 55 offers more time for family, travel…
- A Wiser Retirement®
349. Inheriting Money: What to Do First?
Over the next two decades, an estimated $124 trillion is expected to pass from one generation to the next. For many people, receiving an inheritance can feel…
- A Wiser Retirement®
348. How Do You Build Generational Wealth?
When people hear the phrase “generational wealth,” they often picture trust funds, family empires, and names like Rockefeller or Kennedy. Real generational…
- A Wiser Retirement®
347. If Time Were Money, Would You Be Broke?
Most people track their spending, monitor their investments, and think carefully about where their money goes. But how often do they apply the same level of…
- A Wiser Retirement®
346. Estate Planning Coordination: How Your Attorney, CPA, & Financial Advisor Work Together
For an estate plan to work in real life, your legal documents, account titles, beneficiary designations, tax strategy, and broader financial plan all need to…
- A Wiser Retirement®
345. Are You Reacting to the Headlines or Sticking to the Plan?
You weren't worried about your portfolio at breakfast. Then you check your phone and see recession warnings, tariff headlines, Federal Reserve predictions, and…
- A Wiser Retirement®
344. What Are the Real Uses for Crypto?
Crypto is often associated with speculation, volatility, and investors trying to pick the next big token. However, the digital asset space continues to evolve…
- A Wiser Retirement®
343. 5 Investment Pitfalls High Earners Should Avoid
Earning a high income can create opportunities, but it does not automatically translate into long-term wealth. Many professionals, executives, and business…
- A Wiser Retirement®
342. What Financial Mistakes Don’t You See Coming? (Confidence Traps to Avoid)
Confidence is often viewed as a strength, especially when it comes to building a career, running a business, or making investment decisions. But when it comes…
- A Wiser Retirement®
341. What Happens Next? A Financial Guide After Death
Losing a loved one is emotional enough without having to navigate legal paperwork, financial accounts, and estate settlement decisions at the same time. Yet…
- A Wiser Retirement®
340. 25 Years Of Wiser Wealth Management
Celebrating 25 years in business offers a rare perspective, one shaped by market booms, financial crises, industry shifts, and, most importantly, real client…
- A Wiser Retirement®
339. How To Know If You Can Retire In Five Years? Without Guessing!
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…
- A Wiser Retirement®
338. Real Passive Income: What's Legit and What's Not
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…
- A Wiser Retirement®
337. What Should Be Included in a Financial Plan?
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…
- A Wiser Retirement®
336. Owning Together: What Could Go Wrong?
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…
- A Wiser Retirement®
335. When Should You Take Over Your Parents' Finances?
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…
- A Wiser Retirement®
334. What is a Better Alternative to an Annuity?
Annuities are often marketed as the safe, guaranteed, no-risk answer for retirement income. For many retirees, that promise can sound incredibly appealing…
- A Wiser Retirement®
333. What If Social Security Disappeared?
More than 70 million Americans receive Social Security benefits every month. For millions of retirees, disabled workers, and surviving family members, that…
- A Wiser Retirement®
332. The 2026 Housing Market: Trends, Changes, and What to Expect
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…
- A Wiser Retirement®
331. Crypto, Retirement, and Taxes: What’s the Strategy?
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…
- A Wiser Retirement®
330. How to Build a Business That Funds Your Life, Not Consumes It
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…
- A Wiser Retirement®
329. Digital Estate Planning: What Happens to Your Online Life?
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…
- A Wiser Retirement®
328. Do Pilot Unions Really Make You Richer? The Economics of Collective Bargaining
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®…
- A Wiser Retirement®
327. What Tax Planning Strategies Should You Implement for 2026?
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…
- A Wiser Retirement®
326. Why Crypto Still Confuses Investors
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…
- A Wiser Retirement®
325. What Are The Biggest Financial Scams Right Now?
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…
- A Wiser Retirement®
324. How Can We Build a Strong Future for Our Special Needs Child?
Families navigating a special needs diagnosis often find themselves overwhelmed, emotional, and unsure where to begin. In this episode of A Wiser Retirement®…
- A Wiser Retirement®
323. 2025 Market Recap & 2026 Outlook: What’s Ahead for Investors
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…
- A Wiser Retirement®
322. How Airline Pilots Can Make the Most of Their Profit-Sharing Bonus
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…
- A Wiser Retirement®
321. 10 Financial Resolutions to Kick Off the New Year Right
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…
- A Wiser Retirement®
320. How to Set Smarter Financial Goals for the New Year
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…
- A Wiser Retirement®
319. How to Retire Early Without Running Out of Money
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®…
- A Wiser Retirement®
318. What Is a Power of Attorney and Why Does Everyone Need One?
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®…
- A Wiser Retirement®
317. Pilots Start Here
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…
- A Wiser Retirement®
316. The Best Whiskeys to Gift in 2025
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…
- A Wiser Retirement®
315. Is $1 Million Enough to Retire? Let’s Run the Numbers
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…
- A Wiser Retirement®
314. The Simple Estate Planning Error That Could Hurt Your Family
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…
- A Wiser Retirement®
313. How Can You Help Your Parents Plan Financially for The Future?
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…
- A Wiser Retirement®
312. Is Crypto Right for You?
In this episode of A Wiser Retirement® Podcast, Casey Smith sat down with Robert Swarthout, Founder & CEO of Teton Crypto Capital, to revisit the…
- A Wiser Retirement®
311. Smart Charitable Giving Before December 31st
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…
- A Wiser Retirement®
310. How Can You Travel the World in Retirement?
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…
- A Wiser Retirement®
309. Financial Planning Tools for Pilots, By a Former Airline Pilot
In this episode of A Wiser Retirement® Podcast, Casey Smith, President of Wiser Wealth Management and former airline pilot is with Grace Kennedy, Financial…
- A Wiser Retirement®
308. The Silent Tax: How Inflation Erodes Your Retirement
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…
- A Wiser Retirement®
307. Unlocking the Power of Trusts: 10 Different Trusts & How to Use Them
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…
- A Wiser Retirement®
306. Crypto in Your 401(k)? The Future of Retirement Investing
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…
- A Wiser Retirement®
305. Just Moved to a New State? Here’s Your Financial To-Do List
In this episode of A Wiser Retirement® Podcast, Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA® is joined by Financial Advisor William Medcalf…
- A Wiser Retirement®
304. Under the Radar: Wealth Strategies for the Quietly Rich
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…
- A Wiser Retirement®
303. Pilot’s Guide to Financial Turbulence: Planning for Medical Disabilities
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…
- A Wiser Retirement®
302. What should I do five years before I retire?
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…
- A Wiser Retirement®
301. Crypto Update: Clarity Act, GENIUS Act, and Stablecoins
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…
- A Wiser Retirement®
300. Built to Last: The History and Future of Wiser Wealth Management
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…
- A Wiser Retirement®
299. Financial Conversations Every Couple Should Have Before Saying 'I Do'
In this episode of A Wiser Retirement® Podcast, Shawna Theriault, CFP®, CPA, CDFA® and Financial Advisor Michaela Dowdy dive into the essential financial…
- A Wiser Retirement®
298. America's Balance Sheet: A Financial Advisor's Deep Dive into National Debt
In this episode of A Wiser Retirement® Podcast, Casey Smith, Andrew Pratt, CFA, CBDA, and Shawna Theriault, CFP®, CPA, CDFA®, dive deep into the state of…
- A Wiser Retirement®
297. The Stay-at-Home Equation: Financial Aspects of Leaving the Workforce
In this episode of the A Wiser Retirement® Podcast, we explore the financial and emotional realities of stepping away from the workforce to become a…
- A Wiser Retirement®
296. Crypto Update: Big Beautiful Bill, GENIUS Act, & Crypto Company IPOs
In this episode of A Wiser Retirement® Podcast, Casey Smith sits down with Robert Swarthout, founder and CEO of Teton Crypto Capital, to unpack how recent…