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 stage of life.Whether you’re just getting started or fine-tuning your retirement plan, this podcast is your roadmap to financial freedom.A Wiser Retir...
364. How to Travel More Without Spending More
Your credit card earns points every month, but are they getting you anywhere? A growing rewards balance can feel valuable until you try to turn it into a trip you actually want to take. The opportunity lies in matching your everyday spending with the right rewards, then knowing when a redemption is worth the points, fees, and effort.
In this episode of A Wiser Retirement® Podcast, we discuss how to travel more without spending more. Host Casey Smith welcomes Colin Stroud, Founder of Go Somewhere, to explore credit card rewards, the tradeoffs between points and cash back, a...
363. How Much Should Airline Pilots Have Saved by Age 40, 50, and 60?
You know how many years remain until your final flight. But do you know whether your savings can support what comes next? For airline pilots approaching 40, 50, or 60, a bigger paycheck or a growing 401(k) balance tells only part of the story. Your retirement target depends on what you plan to spend, the income available to cover it, and whether your plan leaves room for flying to end earlier than expected.
In this episode of A Wiser Retirement® Podcast, we discuss how much airline pilots should have saved by ages 40, 50, and 60. Host Casey Smith and Financial Planning Associate G...
362. The Generational Wealth Blueprint: Passing Down Wealth Without Passing Down Problems
“Leave everything equally to the kids” sounds straightforward until the inheritance includes a vacation home nobody agrees on, retirement accounts with tax consequences, or years of financial help that one sibling receives and another does not. The dollar amounts are only part of the decision. How assets pass, who manages them, and what beneficiaries understand can matter just as much.
In this episode of A Wiser Retirement® Podcast, discuss how to pass down wealth without passing down problems. Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®, joins Estate Planning Attorney Arun Gupta to explore the family dynamics, benefic...
361. How Does ChatGPT Manage Investments?
ChatGPT can explain what is in a portfolio, spot funds that overlap, and help you ask better questions about investment costs. But what happens when you ask it specifically about what to do with your retirement savings?
In this episode of A Wiser Retirement® Podcast, Casey Smith and Financial Advisor William Medcalf, CFP®, CBDA discuss how ChatGPT handles an investment question, what changes when it receives more details, and where its analysis still needs human judgment.
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360. What If One Spouse Wants to Retire, and the Other Doesn't?
Retirement does not always happen on the same timeline for both spouses. One person may feel burned out and ready to leave a demanding career, while the other still enjoys working. That difference affects more than a retirement date, it can reshape household cash flow, healthcare coverage, taxes, Social Security decisions, and the way a couple imagines life together.
In this episode of A Wiser Retirement® Podcast, we discuss what happens when one spouse wants to retire while the other continues working. Casey Smith and Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®, explore both the financial cal...
359. Estate Planning for Blended Families: What Most People Get Wrong
Estate planning for a blended family is rarely as simple as deciding who receives each asset. The harder questions involve timing, control, changing relationships, and what happens after one spouse dies. A plan may look complete on paper while leaving room for outcomes no one intended.
In this episode of A Wiser Retirement® Podcast, Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®, and Estate Planning Attorney Arun Gupta, discuss estate planning for blended families. They explore how family dynamics, asset ownership, beneficiary designations, trusts, and financial powers of attorney can affect whether an estate plan works as int...
358. No CLARITY Act, No Crypto?
Crypto regulation in the United States has been caught in a gray area for years. The industry continues to grow, financial institutions are showing more interest, and blockchain technology is finding new uses, but companies still face basic questions about who regulates what and which rules apply. The CLARITY Act is designed to address some of those uncertainties, but its failure would not necessarily mean the end of crypto.
In this episode of A Wiser Retirement® Podcast, Casey Smith is joined by Robert Swarthout, founder and CEO of Teton Crypto Capital, to discuss what could happen if t...
357. Is Long-Term Care Part of Your Retirement Plan?
Long-term care can shift from a distant concern to an immediate financial decision faster than many families expect. It can begin with a few hours of help at home and progress to assisted living, memory care, skilled nursing, or around-the-clock support. Each stage brings different costs, care needs, and family decisions.
In this episode of A Wiser Retirement® Podcast, Casey Smith and Grace Pavel break down what long-term care can actually look like and how families can prepare for it.
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356. Does Debt Build Wealth? Understanding Good Debt vs. Bad Debt
Debt tends to get treated as either a financial tool or a financial trap. The reality is more complicated. Borrowing can help someone buy a home, expand a business, or acquire an income-producing asset, but the same leverage can become a burden when the payment strains cash flow. The important distinction is not simply whether debt exists. It is whether the debt improves your financial position without exposing you to more risk than you can reasonably manage.
In this episode of A Wiser Retirement® Podcast, Casey Smith and Financial Advisor Michaela Dowdy, CFP®, go over the difference be...
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, investment income grows, employer benefits expand, and multiple tax rules begin interacting at the same time. The challenge is not finding a loophole that makes taxes disappear. It is understanding which planning decisions are available and how those decisions fit into a household’s broader financial picture.
In this episode of A Wiser Retirement® Podcast, Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®, and Financial Advisor William Medcalf, CFP®, CBDA, break down practical tax-planning strategies high-i...
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 change. But a market downturn does not automatically mean your long-term financial strategy needs to change. In many cases, the more important question is whether anything about your personal financial situation has changed.
In this episode of A Wiser Retirement® Podcast, we discuss how instead of reacting to the market itself, investors can focus on the elements they can control: liquidity, diversification, portfolio allocation, taxes, contributions, and their long-term financial plan.
R...
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 determine whether someone is financially prepared to retire.
In this episode of A Wiser Retirement® Podcast, we discuss how two households can enter retirement with the same amount of savings and experience very different outcomes. Retirement age, annual spending, taxes, healthcare costs, debt, income sources, and account types all influence how long a portfolio may last.
The more useful question is not simply, “How much have I saved?” It is, “How much does my...
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 for some households, it may become unnecessary once saving, debt management, and cash flow are consistently under control.
In this episode of A Wiser Retirement® Podcast, we discuss how to determine whether a traditional budget still serves a purpose in your financial life.
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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 purchase, pay for college, support a growing family, or begin transferring wealth before it eventually passes through your estate.
However, the biggest risk is not always giving too much. Problems often arise when parents give the wrong asset, at the wrong time, without the right documentation or legal structure.
In this episode of A Wiser Retirement® Podcast, Senior Financial Advisor Shawna Theriault, CFP®, CPA, CD...
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, hobbies, or a new chapter outside aviation, but it is not simply an age decision. It is a financial and lifestyle decision.
In this episode of A Wiser Retirement® Podcast, we discuss what pilots need to consider before leaving the cockpit 10 years before mandatory retirement.
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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 overwhelming. The first challenge usually is not deciding how to invest the money. It is knowing what to do next.
In this episode of A Wiser Retirement® Podcast, we discuss the first steps to take after receiving an inheritance, the common mistakes to avoid, and why it is important to pause before making major financial decisions. An inheritance often comes during a difficult season of grief, family responsibility, and emotional decision-making, w...
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 wealth is not just about leaving behind a large account balance. It is about passing down values, habits, opportunities, work ethic, and a clear understanding of how money can support a meaningful life.
In this episode of A Wiser Retirement® Podcast, we discuss what it really takes to build generational wealth. The conversation goes beyond dollars and investments, focusing instead on how families can prepare the next generation to handle money responsibly, pursue their own goals...
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 attention to their time?
In this episode of A Wiser Retirement® Podcast, Casey Smith sits down with time management expert Megan Sumrell, Founder and CEO of The Pink Bee, to discuss why so many people feel overwhelmed and what they can do to take back control of their time.
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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 align. That is why coordination between your estate planning attorney, CPA, and financial advisor matters.
In this episode of the A Wiser Retirement® Podcast, Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA® sits down with Estate Planning Attorney Arun Gupta of AG Law, and Jordan Gary, CPA of Jones & Kolb to talk about why estate planning isn't a solo effort, and what happens when your professional team actually works together.
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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 market experts declaring that "this time is different."
In this episode of A Wiser Retirement® Podcast, we discuss why reacting to headlines can lead investors away from their long-term financial goals. Drawing on decades of experience through events like the 2008 Financial Crisis, the COVID-19 market downturn, and the inflation-driven volatility of 2022, we explain why discipline, planning, and perspective often matter more than predictions.
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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 beyond that narrative.
In this episode of A Wiser Retirement® Podcast, Casey Smith speaks with Robert Swarthout, owner and founder of Teton Crypto Capital, about how blockchain technology, digital assets, and crypto-related companies are being used in real-world applications today.
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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 owners fall into financial habits that quietly limit their ability to build lasting financial independence.
In this episode of A Wiser Retirement® Podcast, we discuss five common investment pitfalls high earners should avoid and how intentional planning can create more flexibility and clarity for the future.
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<...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 to retirement planning and long-term wealth management, overconfidence can create blind spots that lead to costly financial mistakes.
In this episode of A Wiser Retirement® Podcast, we explore the mindset traps that often affect high earners and successful professionals, and how those assumptions can quietly influence long-term financial outcomes.
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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 for many families, those responsibilities begin almost immediately after a death occurs, often without clear guidance or preparation.
In this episode of the A Wiser Retirement® Podcast, Shawna Theriault, CFP®, CPA, CDFA®, and Estate Planning Attorney Arun Gupta, discuss what really happens after someone dies, common estate planning mistakes, and how families can avoid unnecessary stress, delays, and expenses.
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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 experiences. In this episode of A Wiser Retirement® Podcast, founder Casey Smith reflects on the journey from a startup firm to a comprehensive financial planning team, sharing the lessons learned and what the future holds.
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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 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.
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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 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, breaking down the myths, the misconceptions, and what it actually takes to build income that works for you.
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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 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.
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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 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, CDFA®, and Estate Planning Attorney Arun Gupta break down the most common pitfalls of joint ownership and how to avoid them.
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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 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® Podcast, we unpack one of the hardest financial questions families face: when should you take over your parents’ finances?
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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, 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 may be better served by a simpler, lower-cost strategy.
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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 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 much, and why its disappearance would have massive economic and social consequences.
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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 Retirement® Podcast, we sit down with Tom Townsend, REALTOR® of Tom Townsend Realty Group to break down the housing trends shaping 2026.
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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 Wiser Retirement® Podcast, we break down how to thoughtfully integrate crypto into a diversified retirement plan without derailing your long-term goals.
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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 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 Marty Paradise, Certified Business Coach of Paradise Business Coaching to unpack a tough question: If your business can’t run without you, do you truly own a business or does the business own you?<...
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 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 Theriault, CFP®, CPA, CDFA®, and Estate Planning Attorney Arun Gupta unpack what digital estate planning really means, and how you can take action in under an hour.
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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® Podcast, we break down what unions really change, what they don’t, and why the answer depends on how you define “richer.”
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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 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.
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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, 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.
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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 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.
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